Product thinking

Product sense (also sometimes called Product intuition) often feels inscrutable. “I’ll know a good product when I see it.” To the outsider, it looks like magic, as if some people see the world differently and are more in tune with design. But how does that work?

Intuition is the subconscious process of making predictions, developing expectations, spotting relevant cues, deciding what’s important, and applying or inventing solutions. For more on developing these skills, see the sample chapter How to improve your product intuition

I draw a distinction between intuition and product taste. Intuition drives your output, but taste informs it. Taste also shapes what you take in. Taste combines empathy for the user, domain knowledge of the situation, and your creative ability. Your creative ability is how skilled you are at inventing, identifying, and remixing existing solutions to solve problems. I’m borrowing this definition from Shreya Doshi’s How to improve your product sense.

Are some people born with better taste, more skill, and greater vision for what’s possible? Possibly, but it can be trained. You can intentionally improve your product intuition and cultivate your taste.

Product management

Product management—the only one of the three you can get as a job title—is about deciding what gets built and why.

Product managers have to be aware of customer desires and collect and absorb feedback. They read between the lines and understand what’s going on in customers’ heads. The only way to know what’s important is to have good taste. The only way to understand your users is to have empathy for them.

Then, they must understand stakeholder goals. Most commonly, the stakeholder is the business, organization, or client signing your paychecks. If you’re building a product for yourself, then the stakeholder is you. They will have multiple goals around monetization & growth, which vary based on their industry, monetization model, how they’re financed, and where they are in the product lifecycle.

To get anything done requires engineering capacity. Engineering capacity is made up of the resources you have available, how fast you can build, and what constraints you have from tech debt, governments, and the laws of physics. It’s why we can’t give customers and stakeholders everything they ever wanted. If you could, this wouldn’t be any fun.

Product practice

Intuition and taste are great, but only if they change the output of your work. Product managers can write a tome of roadmaps, user stories, and business cases, but none of it matters if those artifacts aren’t well-informed and actionable.

Building a better product isn’t something you can sit down and do, any more than eating healthier is a task you can check off your to-do list and be done. It’s a new way of seeing the world. A different way of practicing your craft. You bring it to bear in the hundreds of tiny decisions you make every day. How you pay attention to detail and what you do about it.

It permeates every part of the product experience. How it’s built. How it works. The words used to describe it.

There’s no such thing as a solo creative process. All design is collaborative, even if it’s between a creator and a single user. We have to bring this to how we work with others. Within an organization, the only way to be effective is to bring this to your output and build trust and influence. You need to communicate effectively, persuade, and push back on your teammates.

Everything is a product. The software you build, the documents you create, the dinner parties you throw. Hopefully, this framework can help you do that a little bit better.

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1 - Break Inertia

The hardest part is getting started, so make getting started dead simple. If you are stuck in a doom loop, move. Physically move. Stand up. Flap your arms. Anything to get you physically moving. Not starting a project? Do anything. Sketch a note. Archive an email. Create an empty file. Anything! It’s all about pattern breaking.

2 - Just Push Buttons

Don’t know how to get started? Start. Action produces information. You will learn more by doing than by theorizing. I’m reminded of a quote from Ricki Heicklen about their quantitative trading school:

“You need sufficient knowledge to get started” is a self-limiting belief. Getting started is how you know what to do next.

3 - Ask an AI

If you have no idea where to get started, an LLM can get the juices flowing. But to the first point, be wary of planning disguised as procrastination.

I wouldn’t take any plan at face value, but if you don’t know what to do next, brain dump whatever facts, wants, desires, and constraints you have, then prompt your model of choice(if you don’t have a model of choice it’a Opus 4.6) with something like:

Tweak as needed, then go through the exercise. Don’t give the AI solutions. Give it problems, and see where it goes. Even if the plan is bad, the questions could get your brain moving and spark other ideas. You’re exploring, not handing agency over to a flanker.

4 - Moments over Systems

As James Clear says, “You don’t rise to the level of your goals, you fall to the level of your systems.” While there’s truth to this, it can nerd snipe people into believing “you need a system to get started.” You don’t. System or not, you can make decisions and seize good moments.

Systems help with long-term change. But they hurt when you dodge short-term wins because you’re fixated on some bigger fix you’ll put into place “one day.”

You can pass on that glass of wine with dinner. You can order the grilled entree instead of the fried one. You can make one good decision in a single moment. You don’t need a diet plan, a nutritionist, or an app with macros and charts. You can be good without being perfect.

And besides, what is a system but a way to make the good choices more consistently?

5 - Spontaneous Deep Work Sprints

Ive read many productivity and management books, and one of the most consistent pieces of advice I see is this: the secret to getting a lot done is long, uninterrupted time blocks. They suggest you book appointments with yourself and put them on your calendar. Start the blocks like you’re going to the movies: use the bathroom and grab a snack before you lock in.

I’ve tried this several times, and it never sticks. Some productivity tricks work for some people, but personally, I have never been able to take “an appointment with myself” seriously. Hard as I try, I never stick to the work block. The other challenge is distractions: I’m on the manager schedule, and things come up needing immediate attention. Other times it’s slow, where I’m monitoring and on-call, ready to hop in where needed.

What works for me is grabbing time blocks when I can get them. I don’t schedule them, but when I have a deep work task, and I spot open time on the horizon, I decide then and there to lock in for 30, 45, or 60 minutes. The shorter timeframes are a catalyst: How much can I knock out in a sprint? I don’t think knowledge workers sprint enough, going as hard as they can for a short burst.

“Sprint” has lost its meaning in tech. You cannot sprint for 2 weeks. A sprint should feel fast, feel hard, feel uncomfortable. You should take a break after a sprint. Consider a working HIIT session.

It’s ‘moments over systems’ in practice. I can’t reliably block off time, but I can be opportunistic about the time presented to me.

Conclusion

Putting these together, I realize struggling to get started is being trapped by the Nirvana fallacy: You don’t start today because there could be better conditions tomorrow. When in fact, these are lies we tell ourselves, mental labor we bear. If we were to look at it, we would see that it is pointless. We can throw it away. We can walk lighter, freer.

You don’t need motivation to start; you need to start to build motivation. You don’t need a system or a plan to take action; you need to take action before you have a system. You don’t need to make an appointment with your future self; you just need to move.

The 4 types of advisory work

Coaching

Coaching is people-oriented. The primary goal of coaching is to help people grow and achieve their goals. To coach effectively, you need to listen actively and ask good questions. A good coach will get you to give an answer to a question that surprises even yourself.

Consulting

Consulting is solutions-oriented. The goal is to deliver information, expertise, and strategy. When consulting, you need to identify root causes and be able to give advice in a way people will hear. After a good consultation, you’ll feel you have a strategy and know exactly why you’re implementing it.

Managing

Managing is project-oriented. The goal is to close loops, move needles, and track performance. The most valuable management traits are the willingness to have uncomfortable conversations, make decisions, and take ownership. A good manager sets a high-quality bar, holds you to it, and brings out your best performance.

Mentoring

Mentoring is expertise-oriented. The goal is to share specific examples and lessons that help someone build knowledge and expertise. The most valuable mentoring skills are contextualizing expertise and showing, not telling. Your Miyagis, your Yodas, your Professors Xavier.

What happens when you apply the wrong skill

Know your role and shut your mouth

When I was a freelance web developer, I wanted to position myself as a ‘strategic partner’ for two reasons: the work was more interesting, and I could charge a higher hourly rate. I rubbed some clients the wrong way when I tried to contribute to the overall vision.

Once at a local bar, I ordered a whiskey bramble. “Are you sure?“ the server replied, “It’s a fruity and sugary drink.” I felt judged. I knew what I was doing; I was not looking for a more “masculine” order. If I want to put blackberry liqueur and lemon juice in my booze until it tastes like Dimetapp, that’s my business and mine alone. I understood how some of my clients must have felt.

You can’t coach those who don’t want to change, or consult those who don’t want advice. At best, you waste your time. At worst, you damage relationships. Unsolicited coaching or consulting is the professional equivalent of mansplaining.

When to help people, and when to let them struggle

When mentoring, your goal is to give answers. When coaching, your goal is to ask questions and help the coachee discover answers within themselves. The challenge is knowing when to help and when to step back and let people figure it out. It’s tempting to jump in and offer solutions when you see someone struggling. Growth requires discomfort; there is value in wrestling with a thorny challenge.

A heuristic: frustration is ok, confusion is not. People can grind on hard problems, but when they have zero idea what to try next, nudge them in the right direction.

Using the model

How would you rate yourself on each of these, on a scale of 1 to 10? If you broke your week down into a pie chart of the four types, what would it look like? When you think through the four models, you can pinpoint where to focus when skilling up.

“Are they asking for expertise, or do they just want a pair of hands?” “Does this person need help, or do I need to set expectations and hold them to it?” The four models help you pick the right tool for the job. This is why I think it’s important to draw these distinctions. If you can recognize when to apply each skill, you can be a more effective leader.

Initial feedback was tepid

In the initial beta, players explored a fantasy/fairytale setting. You played as Edson, assisted by his pet dog Dinger. This two-character system expanded on the Donkey/Diddy duality of DKC.

Then, Project Dream ran into two problems that forced a pivot. First, the technological landscape shifted. The SNES was riding into the sunset to make way for the Nintendo 64. The game became a 3D project, as was the style at the time. They built a new rendering system for the new hardware.

Second, playtests delivered bad news. The setting was too cliche, too bland, and didn't engage players. They moved to a "harder-edged piratey theme." But changing the environment wasn't enough. The game still felt generic and lacked a hook. So they started experimenting with character designs. One of them: a sword-wielding bear named Banjo.

They pressed on, and got some good news and some bad news. The bad news? Their new rendering system was so deep and complex that the game would take far too long to finish. The good news? Everybody loves the bear.

The project got scrapped. Started again. Now the bear is the main character, his sidekick a bird named Kazooie who lives in his backpack. It wasn’t until the fourth restart of the project that Rare struck gold again.

The final result

Then Mario 64 launched and redefined the platforming genre, dragging it into the 3D era. Banjo felt archaic. The game evolved into a 3D platformer, closer to Mario again. Banjo Kazooie went on to be a smash success, and ranks among the best 3D platformers of its erano.2 on Metacritic for pre-2000 3D platformers.

If you've ever wondered how game companies come up with ideas like "Bear and his bird friend rescue his sister from a wicked witch," now you know. Banjo-Kazooie could have never started as Banjo-Kazooie. Traces of the original iterations survived. The main villain, Gruntilda “Grunty” the Witch, is a wicked witch fairy tale trope. Levels like Treasure Trove Cove harken back to the project’s pirate era. The end result required its circuitous journey.

What we can learn from this

Here's the thing about Rare: they cared about the core idea, and were willing to torch everything else to chase it. They dropped characters, settings, themes, rendering engines, and entire prototypes. It was never about fantasy, or pirates, or bears. It's about friends exploring a fascinating world.

Watch on YouTube

This is an excerpt from my upcoming book on product thinking for engineers, Own the Outcome. Sign up to be notified when it is available for purchase.

1 - The art of agentic agent design

Context is everything

Context is the information you give the LLM to work with. The value you can get out of AI is directly proportional to how much of your work you can put in plain text.

When starting, build a capture spot: a place to easily capture data throughout your day. It could be a folder, an Obsidian vault, anything. It’s a reversible decision, don’t overthink it. You don’t want to think about where you put stuff.

Then, document processes. Start noticing repetitive tasks, and how you might automate them, in all or in part. The more structured and repeatable the process, the more effective the tool will be. Remember the rule: if you do the same thing three times, write it down.

Think in building blocks

In building blocks of agentic agents, I inventoried the individual units of a system. A skill, a standard operating procedure, a file, a folder—these can all be blocks. In software development, blocks are "modules" or "units of code." When working with these systems, it helps to think in building blocks.

There are three software development heuristics I’ve found useful with modules and building blocks alike:

1. The Single Responsibility Principle - A block should only have one job or responsibility.

2. Loose coupling - A block should depend on other blocks as little as possible.

3. High cohesion - The elements of a block should belong together.

You shouldn't try to build one skill that does everything. Even a single process could have several sub-processes. Let's say you want to build your system to help you better handle meetings. That may include:

1. A skill that reviews your notes and helps you prep for meetings

2. A skill that integrates with your calendar to schedule meetings

3. A 3rd-party tool that transcribes meetings and adds them to your capture spot

4. A skill that processes meeting transcriptions and pulls out relevant information

hink about building each part of the system individually. You don’t have to solve everything. Solving one piece can be a win.

It requires practice to figure out the right level of abstraction for ‘block.’ From above, I could in theory have a different skill for each type of meeting. It may be valuable, it may be overkill. How similar are the meetings? That’s where cohesion comes into play.

If you can’t describe what a block does without using the word “and” twice, it should be split up.

When you want to modify or swap out a block, you want to do so with as little friction and side effects as possible. Building self-contained single purpose tooling speeds up iteration.

Check out Anthropic’s collection of official plugins. Imagine if you had to install all of them just to use one feature. Instead, they split their tooling into a few dozen different blocks, so you can pick and choose what to bring into your system.

Single responsibility applies to chats as well. LLMs get dumber the longer they run. They keep every message in context. The further you are from your initial instructions, the more likely they are to drift. Mistakes and misunderstandings accumulate“Lost in the Middle: How Language Models Use Long Contexts” by Liu et al. (2023) from Stanford/Berkeley. https://arxiv.org/abs/2307.03172. Better to clear out the chat and start a new one every time you switch tasks. Even if you are doing the same kind of task many times over, it can be useful to start fresh regularly.

Define your primitives

When starting, think about the primitives of your work and how to model them in plain text. A primitive is any core object you want in your system. Here are some examples from mine:

• projects

• tasks

• people

• teams

• meetings

What's fun is coming up with features that map to your idiosyncrasies, that you don't find in many other projects. I added the monkey primitive, inspired by the HBR piece "Management Time: Who's got the Monkey?" I can track when I'm waiting on a response or feedback from someone (monkey on their back) or someone is waiting on something from me (monkey on my back).

Iteration is (also) everything

Fighter pilot John Boyd gave us the OODA loop: observe, orient, decide, act. Read the situation, pick your move, execute, repeat. You don’t have time to strategize in the middle of a dogfight. You have to act fast and stay in the flow.

AI enables OODA looping at a quicker tempo. You can build, test, and iterate faster than ever before. Experimentation is fast and cheap. Don’t be afraid to try something, and throw it away if it doesn’t work. There will be throwaway work. This isn’t waste; this is part of the process. In creative work there is a cycle of expansion and compression.

That’s why you want well-designed modules. Faster to iterate on small, well-contained subsystems than a sprawling mess.

The difference between a good product and a great one is the number of iteration loops. Quality in creative work comes from labor, not genius. Author John McPhee wrote the book “Draft No. 4.” You don’t have to read it—the title alone can make you a better author if you’ve never considered starting a draft over for the fourth time.

Don’t try to get things perfect on the first shot. Make something, examine what went wrong, adjust your system, and try again.

Use LLMs for design & ideation

Whenever I start a non-trivial piece of work, I go through this "spec-driven development" process:

1. Sketch out a plan of what you want to achieve. Provide as much context as you can. Let’s call this doc spec.md

2. Here’s the important step many skip: Go to Claude with this prompt: study spec.md. interview me and ask me questions so you can improve the spec and then write an implementation plan.

3. After you answer the questions, ask it to write an implementation plan.

4. Start a new chat and ask it to start on the next phase of the implementation plan. (Planning and building are two different tasks, so we clear the memory.)

You can even take it a step before that, and ask the LLM to figure out how you could use the LLM. A tweet from my former coworker Kris Puckett:

Work in these kinds of loops. Get comfortable with them. I can’t emphasize this enough. More iterations get you to where you want to be faster.

2 - A mental shift in how you work

Try working chat-first

The best way to figure out what LLMs can do is to start working chat-first. Whatever you want to do, start with a prompt. If you are already comfortable working in text, this shouldn’t be a large shift for you.

The Dual Loop Framework

When I’m cooking, I have two Claude terminals open in parallel. I call these, borrowing terminology from The E-Myth Revisited: the “working on the business” loop and the “working in the business” loop. The “on the business” loop is the system working on itself. I notice a problem, and I deal with it there. The “in the business” loop is getting the work done. These are separate enough that they can work together without running into one another.

That’s why you want well-designed modules. Easier to parallelize work with small, well-contained subsystems than with a sprawling mess.

The out-to-lunch task

Occasionally, there will be tasks that take a while for the LLM to complete. Something that has helped me: kick these off when you leave at the end of the day, or go to lunch. The agent can chug away while you’re away, and you can review the output when you return.

3 - Avoid getting lost in the sauce

Years ago, I spent too much time playing the game Cookie ClickerI put this link in the footer instead of inline, so you can give it a good think before you click it and go back to that place: Cookie Clicker. This is an idle game where you click a cookie. It taught us all that number-go-up is fun in and of itself—you don’t need the game itself to be fun. There was something hypnotic about building up the cookie clicker system and letting it farm points in the background.

If you’ve been sniped by similar dopamine-hijacking games, watch yourself when working with an LLM. They are a Skinner box, a slot machine where the jackpot is that it does your job for you. They can be hypnotic, even addictive.

There may come a time when you’ve heard of vibe coding, you are tired of typing in a chat box, and so you decide to build a piece of software to support your system. That’s awesome, and you can make a powerful tool. Just maintain focus, and don’t get too distracted building the system instead of building with the system.

I justify this meta-work to myself because I see the value as two-fold: It’s not just a productivity system, it’s a skunkworks project to test new LLM-powered coding techniques. Still, there are diminishing returns on that as well.

If you go down this route, a few words of caution:

Think hard about the architecture, languages, and data storage tools you use to build your system. These will be the hardest to reverse. If you have no idea, I recommend building it as a web app you run locally, with NextJS, TypeScript, SQLite, and a UI framework of your choosing.

Make sure your system has back pressure. Add testing and typechecking early and keep them up to date.

4 - Where do we go from here?

It’s nice to have a system that can automate some tasks for me, and take random unstructured data and help keep it organized. A big part of management is making sure everyone has the information they need, knows who to ask, and is empowered to make decisions.

A question I’ve asked myself during my recent career transition: Which job is more AI-proof, an engineering manager or an engineer? After using LLMs for both, I feel confident that both are safe. LLMs cannot replace the systems design skills needed to engineer software that scales and has a long lifespan. LLMs cannot provide the human connection, empathy, and support that a good manager, mentor, or coach can.

A bin of building blocks

When I was a kid, I loved Lego. What kid didn't? Most of the time, I had a bin, a menagerie of simple colors and cubic pieces. Christmas was the only time I got a set, with themed pieces and instructions. A medieval castle is a medieval castle set, but a bin? It can be anything! It could even be a castle!

The joy of personalized software is that it can be anything, built by you, for you. Instead of giving you instrcutions, I’m giving you a bin. You can study the list, and think about how you can connect these together to build not just any system, but your system.

An example

I have projects and tasks stored in Obsidian files. Then I added a prioritizer agent with a rubric for prioritizing tasks, and a /plan-day command that fetches my agenda from Google Calendar via the gog skill and uses that to rough out a plan for the day. Then it creates a daily journal note for me, with the agenda at the top.

Each bolded word is one Lego in the system. Now to break down what each Lego looks like and how they fit together.

1 - Basic Tools

Claude

Claude, built by Anthropic, is the tool I’m most bullish on. I have a theory that the first follower into a market ends up winning. The Sega Saturn crashed, the Sony Playstation thrived. N*Sync had bigger hits than the Backstreet Boys. ChatGPT is the default, but I find Anthropic’s tooling more useful, so I’ll focus on it.

Four ways to interact with Claude:

1. Standard - I’m lumping the web browser and mobile apps together here. It’s fine if you just want to ask a question, but there is little room to systemize.

2. Installed app - the chat, but a little more featured. You can manage integrations and connect to your file system.

3. Cowork - a research preview behind the paywall, Claude Cowork is Anthropic’s response to latent demand for agentic personal assistants. I haven’t tried this one yet because my preferred method is...

4. Claude Code - a command-line tool that leverages Anthropic’s LLMs. My personal favorite. The command line is the most powerful way to use the computer and the one I’m most used to as a programmer. The terminal can be intimidating, but if you’re moving your work towards text files and automation, it’s a useful skill to have, and not as hard as it looks.

Think of the command line like cooking: it’s as complicated and skill-based as you want it to be. Some people are master chefs who know a litany of techniques. Some, like me, are more utilitarian. I can roast a vegetable, fry an egg, pop a tart. You don’t have to be an expert. A few skills go a long way.

A demo of cowork:

Watch on YouTube

Obsidian

Obsidian is a note-taking tool. The perfect mix of simplicity, utility, and power. You write notes stored as plain-text files. You can link files with wikilinks like [[this]]. Thousands of plugins are available to extend functionality. You can add graphs (Excalidraw), queries (Dataview), or task management (Tasks). If you're interested in an Obsidian + Claude Code setup, there's a plugin that brings a terminal directly into your notes. Plain text is the easiest way to feed an LLM. It gives you permanent storage that is readable and writable by man and machine alike.

Optional: IDE (Cursor or VSCode)

If you’re getting into managing code as part of this exercise, you may want a tool for editing it. These super-powered text editors are called IDEs (Integrated Development Environments). The two best options: VSCode, Microsoft’s editor and the standard choice in the biz, and Cursor, an AI-powered fork. You can use AI via Cursor directly, but if you’re using Claude Code it may not be necessaryFor further reading, check out The Complete Guide: Setting up Claude Code with WSL and Cursor on Windows.

Extending Claude Code

Assume any LLM-based tool is 60% ready-to-go out of the box. You have to put in some effort to get it working how you want. It doesn’t know you, your goals, or your processes. The better you are at getting context out of your head and into Markdown files, the more effective you’ll be. Claude offers a variety of structures to customize and amplify its abilities:

Claude.md

If you’re getting started, put your rules and general logic into Claude.md. Think of this as an initial prompt Claude has at the start of every conversation. You can tell it how you want it to behave, your goals, boundaries, and constraints. Here’s an example (credit to Alex Hillman for this one) to set a communication style:

## Communication Style
- Never end sentences with ellipses (...) - it comes across as passive aggressive
- Ask questions one at a time
- Acknowledge requests neutrally without enthusiasm inflation
- Skip validation language ("great idea!", "perfect!", "excellent!", "amazing!", "kick ass!")
- Skip affirmations ("you're right!", "exactly!", "absolutely!")
- Use neutral confirmations: "Got it", "On it", "Understood", "Starting now"
- Focus on execution over commentary

💡 Pro-tip: Claude loves structured information. Headers and bulleted lists are easier for it to parse.

Slash commands

Slash commands are reusable commands you call while typing into the terminal. Claude has many built in by default, like /clear to empty its memory and /model to select the model. You can also write custom commands for repeatable processes.

If you aren’t sure how to write a slash command (and this will be a recurring theme), ask Claude to write one for you. LLMs are adept at writing text that LLMs can read. You can ask Claude to make modifications later, or go in and make more surgical edits yourself.

Example: have a /fetch-calendar command that gets your daily agenda, or a /line-edit command that does an editing pass on your article.

Agents

If you do this for a while, your Claude.md file will get large. You’ll realize a lot of the rules only matter in certain contexts. When that happens, break it down into agent files. Claude has a slash command, /agents, to help you write them.

Example: I have a frontend-engineer agent that knows how to write code according to my guidelines and style. I have an appointment-maker that knows my meeting preferences and how it integrates with Google Calendar (more on integrations in a bit).

MCPs

MCPs, short for Model Context Protocol, bridge Claude and third-party systems. Think: wrapper for an API. Claude has a list of common MCPs people integrate with.

Example: Two that I find useful, that you can install with a single command, are Notion and Playwright. If you use Notion for work, this gives your system an easy way to read and write files. Playwright, and this is a fun one, gives Claude the ability to open and use a web browser. You can add it with a single command:

claude mcp add playwright npx ‘@playwright/mcp@latest’

In theory, Playwright is the only MCP you need to integrate with every website on the planet. It’s slower and less reliable than direct integrations, though. If you’re worried about handling credentials, what I do is say: “If you run into a login or account verification page, show it to me and I’ll log in.” Then the system won’t have access to your credentials.

Unlike agents and slash commands, I never write custom MCPs. Some are useful, but I find skills and scripted integrations more effective. Still, I can’t deny a one-line command for web access is powerful. If you want to dive deeper on why MCPs may not be the best choice, highly recommend: Your MCP doesn’t need 30 tools, it needs code.

Skills

Skills add extended capabilities to Claude’s toolkit. They contain three key parts: a SKILL.md file explaining what it is, what it does, and how; scripts, code the skill can execute; and examples, which the skill uses to inform its work. Skills can be used by you, or by an agent.

(As a rule, Claude loves patterns and examples. Show, don’t tell, if you want consistency).

When starting with skills, shop the shelf. Anthropic offers skills you can download: Anthropic skills library. A few that might interest you:

• skill-creator - always install this one. You’ll want it when you start creating custom skills.

• The ones that allow Claude to read and write other file types: pdf, pptx, docx, xlsx.

Another source worth checking: Clawdbot. Clawdbot is an open-source, out-of-the-box agent framework. You could start using it as a base, but be warned, it can get expensive. Anthropic has two billing models: Monthly (a set amount of usage each month) and API billing (charges per use). Clawdbot runs exclusively on API billing, which can get pricey. I have run up $25 bills in a couple hours of usage.

BUT, Clawdbot is open source, which means you can browse its internal skill library and copy some into your project. Here are a few I’ve been experimenting with:

• gog - integration with Google Drive and Google Calendar.

• obsidian - for creating Obsidian bases.

• things-mac - integrate with my personal todo list app.

• apple-reminders - programmatically set reminders for myself.

There are many ways to manage context in Claude Code. For a deeper dive, I recommend Understanding Skills, Agents, Subagents, and MCP in Claude Code: When to Use What

2 - Data structures

How will you store and manage the data you’re working with? As stated earlier, plain text is king. Plain text integrates with everything. Free forever. Lasts forever. Start with plain text files. Two syntaxes in particular:

Markdown

Markdown is the lingua franca of plain-text formatting. You can apply simple syntax: bolding, headers, links, lists. No, you cannot change the font or colors. Yes, this is a feature. Everything I write, I draft in Markdown first.

Example

# Markdown

This is a paragraph in markdown. Some text is *bold* and some is _italic_. You can have a

## Hierarchy

### Of Headings

#### To give your document structure

You can even
* make
* a
* list.

• Frontmatter - Frontmatter is a flavor of YAML (which stands for “YAML Ain’t a Markup Language”... yes, it’s a corny recursive acronym). All you need to know: it lets you add structured data to a Markdown file. In Obsidian, these are called “properties.”

Example:

---
title: Building blocks of agentic systems
publish_date: 2026-01-26
section: Root Nodes
blogchain: Prompt Protocols
---

JSON

The next step up: JSON files, which stands for “JavaScript Object Notation.” JSON is a file of nested structured objects. Common use case: config files. Once you start a Claude project, you’ll see ./claude/settings.json as an example.

{
  title: "Building blocks of agentic systems",
  publishDate: "2026-01-26",
  section: "Root Nodes",
  blogchain: "Prompt Protocols"
}

SQLite

SQLite is a dead simple database that lives in a single file. Useful when you have several types of data and want to map relationships between them. SQLite helps when you need to aggregate records or create relations between them. If you’re an accountant who’s put 600 transactions in Markdown files, it might be time to consider SQLite.

3 - Computing

LLMs are cool and advanced, but as we’ve seen with plain text, the most powerful tooling combines them with simple computing practices that have been around for decades.

You may have seen the GPT ‘gotcha’ where many LLMs could not correctly count the number of ‘R’s in the word ‘Strawberry’

A brief explanation of why this happens (hat tip to Zhu Liang):

LLMs break text into smaller chunks for processing through a process called tokenization. Then they catalog them with token IDs. When an LLM “sees” the word “strawberry,” what it gets is a series of token IDs {496, 675, 15717} that map to certain tokens {”str”,”aw”,”berry”}. It sees 2 tokens with an ‘R’, so it thinks there are two ‘R’s.

Now, let’s compare that to Python code that does the same thing.

word = "Strawberry"
word.count('r')

None of that tokenizing and indexing. Your computer doesn’t have to send a prompt to a model in a data center and wait for a response. It just. Counts. the. letters.

What I’m saying: there’s a lot of work that doesn’t require intelligence. If a process is repeatable and doesn’t require judgment or abstract reasoning, you’re better off having code do the job than an LLM.

Scripts

But hasn’t this always been possible? Code to automate tasks is nothing new. What’s new is how easy it is to have an LLM write simple scripts for you and run them. This is what made the command line interface such a powerful pattern: LLMs run on text. Command lines are built on a philosophy of text in, text out. Combine them and you can build powerful systems.

A script is a single-file, single-purpose computer program. Typically written in Bash, Python, or JavaScript. Sometimes the model writes, executes, and deletes a script behind the scenes.

Web based UIs

Some tasks are arduous to work in via text. Maybe you want to add some pizazz to your work. One option: ask Claude to build a small web page or app that runs on your local computer.

It will not get it right the first time. There will be bugs. You’ll need to iterate.

Be wary: this is an easy rabbit hole. If you aren’t careful, iterating and maintaining your UI system becomes a job of its own and a distraction from your original goals.

I prefer Next.js for these. You also don’t need great design skills: several free off-the-shelf design systems exist. Here’s a list. Pick one that matches your vibe:

• Retro UI

• AI SDK Agents

• Cult UI

• Tailark

• Kokonut UI

• Magic UI

• Eldora UI

• Aceternity UI

• shadcn/ui

• Kibo UI

• Mantine

• Naive UI

• Ionic Framework

• Shoelace

• daisyUI

• Paper CSS

Cron

Cron jobs let you run scripts or commands at regular intervals. Maybe you wrote a “check-inbox” command that you run manually to sync with your inbox. With a cron, you could have it run every hour. Crons let you trigger scripts at different parts of the day.

Version control (Git)

I don’t know how other document-based knowledge workers survive without a version control system like Git. Git lets you keep a changelog of all committed changesets to your pile of files. Typically it’s used for code, but nothing stops you from using it for Markdown files. You can also create branches, like a temporary copy, and try something. If it works, you merge changes into your main copy. If it doesn’t, throw the branch away, no harm done, no permanent changes made.

Version control lets you iterate fearlessly. You can also use tools like GitHub to back up your work online, and even share it publicly.

A good rule of thumb: add a directive to your Claude.md to make a git commit when it finishes a unit of work.

4 - Integrations

Lastly, think about what tools you use in your day-to-day work. Apps your job provides, or tools you use personally to be more productive. Common culprits: Email, Google Drive, Notion, Slack, task trackers, and calendar apps.

Can you think of ways you might want your system to interact with them? To fetch data, write to them, or take actions? See if they have a publicly available MCP or API. Maybe you can find a Claude Code skill on GitHub or another marketplace. Between all of this, there are ways to create new slash commands, skills, or documents that help you do your job more effectively.

What comes next

Building these systems takes time and several rounds of iteration. In the next and final part, I’ll go through my notes and process for building my agentic assistant over the past few weeks.

Update: Part 3 is live:

Mistakes I Made Building My AI Assistant (And What I Learned)

A different kind of unicorn…

Alex hit on something in his video: no project management system or CRM ever fits quite right. Work is idiosyncratic. Everyone has unique contexts, motivations, strengths, and foibles. Ashe Magalhaes has a wholesome system with a compliments workflow, birthday reminders, a custom friend social feed, and gratitude journaling.

Vaughn Tan hits on this in Boring Tiny Tools: “Generative AI coding tools now enable high-utility, highly customised, but narrowly scoped software.”

A new genre of software is emerging. Maybe “Unicorn” will no longer refer to a billion-dollar company, but to rare, one-of-a-kind precision software, tailor-made just for you.

…if you can build them

But don’t expect a magic silver bullet. Despite what people selling AI courses tell you, I don’t know that Claude Code is for “everyone.” I’m not gatekeeping or acting superior, only setting expectations for what raising your rat looks like.

Do you have systems? Can you get them out of your head, breaking them into components with clear instructions, constraints, and success criteria? Sure, you can get a system up in a couple of hours, but larger gains take many, many rounds of iteration. Alex keeps a dev log of his assistant (or at least he did; this prompt implies his agent is now self-blogging). He’s at 96 days and counting.

I was already taking notes to a near-unhealthy degree and tracking tasks in markdown files. It helps that I have 15 years of experience as an engineer. Turning fuzzy business requirements into code is kinda my jam.

Could this eventually be a job I have? Acting as a translator and transcriber for people who can’t cross the brain-to-LLM bridge? Vaughn Tan thinks so. Again from Boring Tiny Tools:

Could I build a system like this for someone else? Technically, yes, but I’m not convinced it would be good. It would be better to teach or collaborate with people and let them figure out what to build and how to get there. You have to cook with your rat.

This piece attempts to teach Claude Code for the non-engineer. If you’re the target reader, I’d love to hear if you found it valuable, or if it’s all still mind-boggling.

If you want someone to riff with on this stuff, shoot me an email or DM.

But for now, I’m off to do another few rounds of iteration on my agentic agent, whom I’ve christened Agentic Agent, because I hate anthropomorphizing AI. Next week, I’ll go into more detail about how I built my initial prototype.

Update: Read parts 2 and 3 here:

Building Blocks of Agentic Agents

Mistakes I Made Building My AI Assistant (And What I Learned)

1 - Needy programs

There has been a shift in how technology interacts with users. I sensed this for a long time, but couldn’t articulate it. That is, until Niki Tonsky captured it with the term “needy programs.”

Need programs get in the user’s way, and put the wants of the software provider over the needs of the person using it.

Accounts

I hate it when I buy something from an online store, a niche gift from a place I don’t plan on returning to, and now I have an account with them. To paraphrase Mitch Hedberg, I give you money, you send me a package. There is no need to bring email subscriptions into this. I not 15% off of my next purchase, I want you to get off of my back about a next purchase.

Updates

A man shopping for a washing machine sees on the label that it has Wi-Fi capabilities. He approaches a floor person. “Why does a washing machine need internet access?”

“So the manufacturer can install security updates,” responds the employee.

“Why does a washing machine need security updates?”

“Because it’s connected to the internet!”

I once sat down to play a game on my Playstation 5 and was greeted with a barrage of pop-ups. The game needed updates. The console needed updates. The freaking television? Updates.[1]. I’m showing my age, but I miss when you could plug a cartridge into a system, turn it on, and it would just go.

Notifications

We are bombarded by notifications. Product teams know we cannot resist the siren’s call of the red numbered dot. We sit there popping these pimples on our smartphones, hoping they don’t come back. Notifying the user is fine in some cases but should be used sparingly. Notifications are a to-do list the user didn’t sign up for.

Login Modal Ambushes

I don’t need to know about your new feature the moment I log in. I logged in to do a task, and these in-app advertisements are getting in my way.

Bloat

I purchased a smart TV and, to my surprise, the home screen lagged the first time I turned it on. Response time was slow and the interface was difficult to use. The home screen had ads, pre-installed garbage apps, home connect features, and background processes running for speech control, AI features, and metrics collection. I had to find a tutorial online and spend 20 minutes in the settings getting the television to a usable state. I considered setting up an LG developer account so I could enable developer mode and disable even more stuff., I should not have to do this level of tech support on a brand new product. Lord help me if my in-laws ever buy an LG TV.

2 - Removing decisions

You should make decisions as easy as possible for users. But be wary, simpler isn’t always better.

We want software to be easy. Ideally, it makes decisions as easy as possible for us. But at times, this can go to far: simplification can steal choice away from the user. It’s the difference between a Prix Fixe menu and an airline that doesn’t let you choose your seat.

Overly simplifying interfaces

Consider touch screens in modern cars. It’s a cleaner look, replacing a swath of dials and buttons with a sleek screen. When I was growing up, we didn’t have radio buttons in forms, only buttons on the car stereo.

This simplicity comes with a cost. You no longer get the satisfying thonk sound when you switch stations. And a study by a Swedish car magazine shows that drivers take four times longer to complete a task on a touch screen compared to analog controls. This isn’t an inconvenience, it’s dangerous. The simplified design removed affordances. Drivers can no longer feel their way around the controls. drivers have to navigate menus to find the settings they’re looking for.

Greedy defaults

Smart defaults make selections for the user to reduce cognitive load. Greedy defaults exploit the shortcuts the user’s brain takes to get them to act against their own self-interest. A common example: a checkbox for “subscribe for updates” in a store checkout page that’s already set to yes. Many applications have tracking and other behaviors that benefit only the company turned on by default.

Hijacking the user’s machine

Only steal the user’s focus when it’s helpful to them, not to force their hand. Users own their machines and should decide what to do with them.

Respect the machine’s default behavior. Don’t override basic functionality within your application, or behaviors expected within an element. Examples: removing the ability to right-click on items, disabling the esc key, or having a video with no way to stop or scrub playback.

Holding the user hostage

Some applications force users to stay within a process, or worse, in a subscription, without their consent. If they can quit, they make it difficult. Give users opportunities to cancel out of any process. Let them stop a process and come back to it later. Users should be free to come and go as they please. It’s an app, not a cult.

This goes for their data too. Your application should let users export their data and take it elsewhere. Part of the genius of the Unix philosophy is that every program takes plain text as input and returns plain text as output. Use common file formats and sensible structures. Be more like Unix.

Don’t implement cancellation flows that are intentionally confusing, long-winded, or hidden. If someone can sign up for a product online, they should be able to cancel online, without picking up the telephone.

Case study: Algorithmic feeds

This is a whole other article, but I believe Google killing their Reader product contributed to the global rise of far-right fascist movements. Between 2013-2016, the way users consumed information via the internet changed. All major social media applications switched to algorithmic feeds. At the same time, Google killed their RSS reader to push people toward their own algorithmic feed product, Google+. Creators started making content for the algorithm instead of building more natural ways of connecting and sharing information. It wasn’t apparent at the time, but in retrospect it was a foundational shift from people searching out content to having content pushed at them. From pull to push.

Researchers have defined what they call attentional agency. Imagine a tug-of-war with the agent (user) on one side, the advocate (person controlling the algorithms) on the other, and the platform as the battlefield. Advocates give you options to select from based on what they think will increase engagement, not what best matches what you asked for. Chronological feeds contain 50% less hateful content and 3x the amount of links to news sources on average. Algorithmic feeds have more tabloids and mainstream news; chronological feeds have more local sources.

Users spend 73% more time on and engage nearly 20x as much with an algorithmic feed vs. a chronological one. Users also experience a palpable increase in anger (0.47 SD), anxiety (0.23 SD), sadness (0.22 SD), and a 21% increase in hostility toward out-groups.

The metrics the business cares about went up, with a real cost for the user. We feel worse, we have less control, and the platforms profit.

3 - Defrauding the user

Sometimes using the internet, it feels like everything is a little bit of a grift. If it isn’t in your face, it’s behind your back.

Deceptive pricing practices

As of 2023, Google Workspace offered two pricing tiers: Business Plus and the more expensive Business Starter. Starter was not available during signup. The only way to get it was to sign up for the more expensive plan, then downgrade. Users should be informed about how much they will pay, what they will receive, and whether it’s one-time or recurring.

Fake Urgency & Social Proof

Every time I see a store with “only 2 left!” there always seem to be only 2 left. Like the general store in O Brother Where Art Thou, these places are a goddamn anomaly. Authentic urgency is fine, but creating imaginary scarcity is fraud.

Public by default

Applications with a social component tend to default to everything being public. While this is useful for catching senators with questionable Venmo transactions, it’s harmful to users at scale. Users should opt-in to behavior that could pose a risk, and sharing things online poses a risk.

Pricing page traps

Ever click on a feature and instead of getting it, you get an upsell to the paid option? Actions should do what the user expects.

4 - Emotional Manipulation

This is the big one. Many “growth hackers” and product people don’t understand the difference between persuasion and manipulation. There’s nothing wrong with being aware of emotion in design (if you want to explore that topic, I recommend Aaron Walter’s Designing for Emotion). The problem arises when you use these techniques to make people act out of fear instead of from a place of agency.

Confirmshaming

Opt-out buttons worded in a belittling or derogatory manner, making users feel bad about declining. A chilling example, care of Deceptive Design (who coined the term):

The eCommerce website mimedic.com sells first aid packs and medical supplies. They used the following pop-up when asking for permission to send website notifications:

The copy "no, I don't want to stay alive" is troubling, given the context of serving people who have been exposed to trauma and death in their work.

Gamification & Gambling Mechanics

Gamification adds game mechanics to systems with the element of play stripped away. Leaderboards, quests, achievements, unlocks, and XP to drive behavior. It is psychologically manipulative. Uber rolled out a “quest” feature for drivers, offering bonus cash for hitting milestones. But as drivers got close to their goal, Uber fed them lower-paying rides, keeping them behind the wheel longer. They’re out driving, eyes burning, concentration fraying. Uber isn’t helping drivers have fun; it’s putting them and others at risk to increase profits.

Gamification can have positive effects too. I used to go to a CrossFit gym, fully aware that CrossFit is just gamified workouts. But it worked: it kept me coming back and got me in better shape.

Duolingo exemplifies the duality of gamification. On the paid plan, they use it to encourage language learning. On the free plan, they use it to encourage upgrading to the paid plan.

When you see gamified systems, ask: What behaviors is the system pushing? Who benefits most?

Engagement at any cost

The state of social media makes sense once you see how the numbers work. The algorithms are not trying to show you what you want to see; they’re trying to show you what will keep you engaged. Engagement can come from interest and curiosity, but it can also come from outrage, hatred, shock, anxiety, and fear. The latter is much easier and more effective.

You are the last line of defense

As software engineers, we are responsible for the work we put out into the world. Technology is powerful and has real impacts on society. I am reminded of an interview with Bo Burnham on the attention economy:

Watch on YouTube

I understand that pushing back against these asks is not easy. But I am reminded of another quote, this time from Jerry Garcia:

Case study: Unix Core Library

The Unix core library epitomizes many elements of agentic user design. A suite of 100ish single-purpose command-line tools, built at the foundational level of the OS, empowers the user to do whatever they want with text files. find to look for files, grep to search their contents, awk to process them, rm to remove them.

In the 1970s, Bell Labs had a tool-based culture. Engineers were encouraged to build tooling to solve their own problems. If others found them useful, they would roll the tools up into the Unix operating system. These tools were built around the three-pronged Unix design philosophy:

1. Do one thing and do it well.

2. Write programs that work together.

3. Everything is a file.

This way, instead of building products to solve every problem, they could build utilities people could apply to single fixes. They were building screwdrivers and gears so that other people could build specialized machinery. This philosophy led to the creation of agency-friendly software:

Setting and achieving goals: Users can compose tools together with pipes to create complex workflows for any text-based goal. If everything is a file, then anything is achievable.

Doing tasks because you decide to: The tool never suggests or manipulates. No “recommended workflows,” no attempts to influence your choices. It sits idle until you give it explicit commands.

Figureoutable: I won’t pretend using the Unix tooling is easy. It requires skill to wield. But the tools follow consistent conventions: flags with - or --, stdin/stdout patterns, and exit codes. Every tool has man pages and --help flags. Documentation is comprehensive and built in. Users can discover capabilities and see examples. Learn one tool’s patterns, and you’ve learned them all.

Empowered to make decisions: Tools don’t make hidden decisions on your behalf. You choose verbosity levels, output formats, error handling, and behavior. Every option is exposed as a flag. The tool does what you tell it.

No surprises: Every tool does its one job, no more, no less. grep always searches, sort always sorts. Tools are deterministic and transparent.

Useful feedback: Clear separation of stdout (results) and stderr (errors). Exit codes signal success (0) or failure (non-zero). Feedback is a file (everything is a file), parseable, so you can build on it.

The Unix CLI embodies “here’s what you can do” rather than “here’s what the product does.”

What lessons can we take from this and apply to building products?

Build software that is both simple and powerful

Products should be simple enough for novices and powerful for experts. Examples of power user features:

1. Hotkeys: I hope to one day be the kind of person who never touches the mouse. Hotkeys help people move faster when they’re willing to learn them.

2. Command palettes: A cousin of hotkeys, command palettes let users complete tasks via text instead of clicking and dragging.

3. Macros: Excel lets users script macros in VBA.

4. Advanced configuration: Give users more customization for those who want it. (Warning: these can create maintenance debt if you’re not careful.)

Anticipate the user getting stuck, and toss them a rope

Users will get stuck. Anticipate what bogs them down and be there when they need you most:

1. Confused. Make first-time use as simple as possible. Affordances and consistency clarify what to do next.

2. Stuck. Offer help, tips, or support docs to help them figure out the next step.

3. Unmotivated. Show progress, offer wins along the way, and connect the current task to their ultimate goal.

4. Distracted. Remove irrelevant elements from the view.

5. The task is hard and there’s nothing you can do about it. Acknowledge it. As Jake the Dog said in Adventure Time: “Dude, suckin’ at something is the first step to being sorta good at something.”

Robots & Iron Man Suits

There are two patterns technology can take when doing a task: It does it for you, or it makes you better. I call these robots and Iron Man suits. A robot handles something for the user. An Iron Man suit amplifies their abilities. GitHub Actions are robots. VSCode is an Iron Man suit. Everyone thinks ChatGPT is a robot, but it’s an Iron Man suit. Both can either enhance or take away agency.

Robots

With robots, the user hands off the task. For example, autopay for bills, CI/CD pipelines, and email filters. These patterns work best when:

• The task is repetitive and boring

• Success criteria are clear and measurable

• It’s recurring and predictable

Robots increase agency when they let you complete a task you otherwise couldn’t, or remove a task you don’t want to do from your plate entirely. Automated bill pay means you never have to think about when to pay your bill.

If you’ve watched any Sci-fi, you can imagine how this type of automation could start working against the user’s best interest. When software starts making decisions, it may do so against the user’s interests. Pod bay doors are all well and good until they won’t open. A bed that warms to the perfect temperature is nice until an AWS outage contorts it into an unusable position. They can become a black box that removes a user’s understanding and ability to decide. They can be difficult or impossible to modify.

Aim to take work off the user’s plate only when you can preserve their ability to decide and receive feedback.

Iron Man suits

Iron Man suits enhance the user’s abilities. Examples: feature-rich IDEs and design tools like Figma. Consider this approach when:

• The task requires subjective judgment and creativity

• The user needs to understand what’s happening

• The user is practicing a skill they can improve

Iron Man suits increase agency by giving you more power to complete tasks. I’m no designer, but tools like Figma and Canva enable me to communicate more visually. They enable me to complete a task I otherwise couldn’t.

The opposite happens when the Iron Man suit becomes a burden, adding to your workload instead of lightening it. Salesforce is configurable, but it’s so configurable that configuring it becomes a full-time job. Ticket trackers like Jira can streamline project management, but can also become a job unto themselves. Digital notebooks like Obsidian and OneNote can help you manage knowledge better, but can also become a burden instead of fuel for creative work.

Simplify decisions

Decision fatigue is real. If users feel it in your product, they may leave and never return. Make decisions few and easy, while preserving agency.

Keep choices to a minimum. Hick’s law: the time to make a decision increases with the number of choices. If you can’t reduce the number of choices, group them or give users ways to sort and filter (autocomplete, for example).

Give them smart defaults. A smart default is a choice that’s right most of the time. Make the right thing easy and the wrong thing hard.

Defer choices. If a choice doesn’t need to be made now, let the user make it later.

Agentic User Patterns

From looking at what agency is, how people attack it, and how others have put it into practice, we can form some patterns to guide us: We give users as few decisions as they need, but no fewer. We offer all the information and feedback they need to decide, but no more. We build products that do what they promise, when they promise, and nothing else.

Remember your place

Software is a tool for the user. The user is not a tool for your product. Design for agency: empower users to decide, feel confident, feel safe, and get shit done.

Thank you for reading. This post is part 1 of a 2-part series. The following post will explore this one’s shadow, anti-agentic dark patterns.

How to write a strategy

The word ‘Strategy’ conjures images of McKinsey consultants billing $600/hr to create slide decks. Decks with lots of charts. Charts that will do more harm than good. Strategy need not be highfalutin, and unlike McKinsey consultants, can deliver real value and change. Here’s a dead-simple summary of what I mean by strategy, riffing on the ‘kernel’ idea from ‘Good Strategy / Bad Strategy.’ A strategy has four parts:

1. Goal - What do you want to accomplish?

2. Diagnosis - What’s wrong?

3. Guiding policy - Your approach, what to do, what not to do.

4. Coherent Actions - How can you put this into practice?

That’s it. It doesn’t need to be a huge document or grandiose idea. It could be a paragraph. It could be a sentence. WWJD is a complete strategy.

(Tech bros made that weird, too, by the way)

An example

At the start of the year, I declared 2025 my 'year of actionable thinking', and I crafted the 'Leeroy Jenkins Strategy':

1. Goal - Spend less time overthinking, more time on execution

2. Diagnosis - Too much time spent on planning and infotainment.

3. General policies - Be intentional about planning and research. All information should be actionable. Favor taking small next actions and focus on progress over perfection.

4. Coherent Actions - See Jenkins Strategems, Just Push Buttons

At the beginning of the year, I was also moving from IC to engineering manager. I didn’t know what the job would entail. But having a strategy meant I could apply my original goal to novel areas. I could learn what questions to ask in meetings to drive decisions and keep us out of a planning bog.

An anti-example

My stated goal of publishing 10 posts in December. I had a goal, but lacked a diagnosis. I hadn’t considered the amount of holiday planning and activities, the ‘get it in by Q4’ work push, the general crud, the persistent cough all parents of young children have in winter. The sun, despite all the negative feedback, continues to set at 4:47pm. How can I be expected to hustle when the sun can barely put in a full day’s work?

3 ways to keep yourself honest

Once you have a strategy, you have to ensure you put it into action. Wisdom is realizing this video is sincere:

Watch on YouTube

What helped me:

Regular check-ins - If you take away one thing from this post, let it be this: If you want to focus on a goal for the long term, set up a system to bring your attention to it regularly. Add a recurring task to your to-do list. Slap a sticky note on your bathroom mirror. Wear a charm or bracelet.

Strategy-driven preparation - What can you do today to enact your strategy in the future? Strategy can help you in the moment, but also beforehand, in planning and preparation. Map your route before you leave.

The Focusing Question - I’m a stan for Gary Keller’s The One Thing. Though I’ll admit you can get 90% of the value by asking yourself the “Focusing Question”, both regularly and when you don’t know what to do next: “What’s the one thing I can do such that by doing it everything else will be easier or unnecessary?”

What do you want to accomplish next year? How could you write a strategy to achieve it?

Maybe I should make a WWSLaBD bracelet 🤔

What is product taste?

Product taste is hard to define. The most useful model I’ve found comes from Shreya Doshi’s “How to Improve Your Product Sense.“Product sense” and “product taste” are interchangeable.” She decomposes it into three parts, stated here as “The Product Taste Equation:”

Empathy: Caring about the needs of the user and how they feel when they use your product. Defining problems and recognizing opportunities.

Domain knowledge: Knowledge about the space you can bring to bear on the problem; the set of tools you have at your disposal to solve that problem.

Creativity: Your capability to invent, identify, combine, and remix solutions to solve problems.

Taste is used to make subjective value judgements in your work. You apply all of these factors, together, to inform and improve both the inputs and outputs of your work.

Taste requires coherence

Taste is about fitting all three values together in a way that makes sense. A product made with good taste meets all of the goals, values, and preferences of the users and the creator.

Taste isn’t about deciding what’s “good” or what’s “bad.” It’s about deciding what is coherent and what isn’t. In his 1964 work Notes on the Synthesis of Form, Christopher Alexander describes a system of relationships he calls the “ensemble” of form, context, and fitness between them. Form is the shape and structure of a product. Context is the environment in which the product is used. Fitness describes how the product matches the intended function within its context.

Good taste is about deciding what works in context. Coherence is fitness. Good taste is being able to recognize a good fit. Taste brings clarity.

Taste as filter

When you can see what is coherent, you can begin to emphasize what matters most, and downplay or eliminate what doesn’t. These decisions happen at every part of the creative process:

When looking at data and analytics: Data can inform value judgements, but it cannot replace them. When we listen to numbers, we still decide which numbers are worth listening to and how much weight to give them. Taste is applied when people believe they are being purely objective. Leaning on “But the numbers say” without further justification is a cop-out.

When collecting qualitative customer data: Your taste dictates what questions you ask, and where you dig deeper and ask follow-ups. Like data, it helps you decide which feedback to listen to and which to ignore.

Prioritization: What do you solve first? Is a problem worth solving at all? Which strength should you play towards? All of these are ultimately questions of taste.

Taste is attention to detail

You can tell when someone has put in the effort to pay attention to every little detail of an application. You see it in intentionally designed loading states, in thoughtful, useful error messages. When you hit a weird edge case and the product is one step ahead of you, handling it gracefully. And you think, “Wow, they thought about everything.”

Details compound.

I was once sitting at a cocktail lounge on a business trip to SF, and I overheard a bartender teaching a new hire how to make a mojito. He talked about the order of the ingredients and how many ice cubes. How many mint leaves to put into the drink, and how to arrange them. He talked about how these details affected the drink's flavor and presentation. He mentioned that the person can see you making the drink, so the performance of making it is part of the service.

Did you know Spotify’s shuffle isn’t truly random? It avoids playing the same artist twice in five songs. Those are the kinds of details that separate good products from great ones. When you’ve put your empathy for the user over what is ‘technically correct.’

Taste in software engineering

What does taste look like when applied to writing code? At a foundational level, you may have ideas on what type of code you prefer to write. Do you write lots of small, single-purpose components, or larger, more utilitarian ones? How do you feel about TailwindCSS?For those who aren’t frontend developers, TailwindCSS is a design framework based on ‘utility CSS.’ It’s a divisive pattern. Some people love using it, others can’t stand it.

Another form of taste shows in early systems design: realizing what’s changeable and what isn’t. Certain database decisions and interfaces will be difficult to change in the future, while others are more malleable. Some things are one-way doors, and some decisions reverse easily. The trick is knowing which one is which.

Software taste is about writing code that best fits your context. Coding with coherence. If you write software for a company with coding standards, you stick to those standards over your own.

It’s important to remember that in-code interfaces are a product. They are made with a purpose, for an audience (other engineers).

Taste is idiosyncratic

Everyone’s taste is different. Every company and every product exists in a different context. That’s what makes developing your taste worth investing in. Doing so will help you live a life that’s more coherent with both what you want and what you like. It is also specific to certain skillsets and proclivities.

For example, I feel I have a decent sense of what makes a good product or process. I’m smarter than the average bear when it comes to non-fiction business writing, else we wouldn’t be here together right now. I will never share my Spotify playlists, lest you see the cringy 00s nu-metal of my youth that I still listen to today.

The product taste equation includes your domain expertise. You can’t be an expert at everything. If you aren’t sure where to start developing your taste, start with what you’re best at.

How do you tell the difference between product taste, subjective preference, and bullshit?

You might be thinking, If taste is subjective and personal, why should anyone else listen or believe you? Why should you listen to anyone else?

One aspect of believability is a consistent track record of wins. Has the person had successes before? Do they seem to be right more often than not? Why do people let Rick Rubin produce albums? Because he got the best out of Jay-Z, Lana Del Rey, Adele, Weezer, Slipknot, Slayer, Black Sabbath, Johnny Cash, The Mars Volta, Macy Gray, and Tom Petty. If he’s producing your album, chances are he can get the best out of you to.

Watch on YouTube

For subjective decisions, you can still be more objective on what you and others are applying that judgment to. Are you trying to decide what’s best for the user or for you? Are you trying to justify your pitch, or are you seeking the truth? Are you applying taste, or stroking your ego?

You can typically tell when someone knows what they talk about or cares about others. I once heard a product manager say in a meeting, “Here are the actions we want the user to take.” Which, to me, is at least a yellow flag. What does it say when they are more focused on driving the user towards what they want, instead of trying to empower the user to do what they want to do?

The best way to detect bullshit is to watch for inconsistencies and a lack of ability to explain why they are making a decision, from any logical, emotional, or aesthetic endpoint.

There will never be a complete answer. How do you decide who to listen to and who to ignore? Are you ahead of me this time? That’s right, it’s applying your taste.

This is an excerpt from my upcoming book on product thinking for engineers. Sign up to be notified when it is available for purchase.

Number go up is stupidly, infuriatingly effective

It’s been a while since I challenged myself like this, and even longer since I succeeded at one. Apparently, the secret was to set up a spreadsheet, share it with a few friends, and track my progress.

I suspect it was the accountability in particular. I don’t know if they looked, but I knew that they could.

I kind of hate how effective this was on me. I am well aware of how companies use gamification to manipulate you: I am on day 87 of my Duolingo streak and I don’t even quiero aprendar Español anymore. I didn’t think it would work if I did it to myself.

But it comes with a cost

The metric was a tradeoff: I hit the goal. I have a lot of wet clay to work with. But I also spent a lot of time in ‘shitty first draft’ mode. I hesitated to edit because editing means fewer words, especially towards the end when it was down to the wire.

But in exchange, I have content to work with, I’ve built new writing skills, and I have more confidence that I can take on large self-directed projects. Worth it.

Being Consistent-ish

I needed to hit 778 words per day on average to reach my goal. But if I knocked out 2,000 in a day, I could take a day off and still be on track. I liked that the structure was consistent-ish. I wasn’t beholden to perfect daily consistency, awkwardly explaining to my in-laws why I’m furtively typing during Thanksgiving dinner.

There’s an apocryphal quote from Jerry Seinfeld about forming an unbreakable chain:

Later, in an interview with Oliver Burkeman, Seinfeld revealed he never meant this to be taken so literally:

Perfect streaks can be counterproductive. Chain systems can become a restraint instead of a motivator. If my Duolingo streak ever gets reset to 1, I promise you there will not be another 2.

We all have off days. Why punish yourself for being human?

Strengthening my words-per-session muscle

Before he founded Kit, Nathan Barry kept a writing streak of 1,000 words per day. He cited the “Seinfeld Strategy” as inspiration. He did this for 80 days and published The App Design Handbook. When I first heard about this, it sounded impossible. 1,000 words? That’s so many! How do you have that much to say, and so consistently?

Now, I’ve put in reps. 1,000 words feels easier now. That doesn’t mean I plan to bloviate and pump up my word count. What I do have now is ways to go deeper and make the material actionable: finding case studies to illustrate and adding exercises to put into practice. It’s not about using more words; it’s about having more of value to say using as few words as possibleLanguage should be simple, too, though I cannot resist the temptation to occasionally toss in a college word like ‘bloviate.’.

I have no interest in writing a book on product theory. Knowledge is useless without strategies to put it into action. So, I lifted techniques from Diataxis, a framework for writing actionable documentation. It gave me more ways to think and talk about topics.

For example, The Big List of Product Heuristics is reference, Trust Over Titles: The Engineer’s Guide to Workplace Influence is a how-to guide, How to Improve Your Product Intuition is explanation.

What comes next

I’ve spent enough time in monk mode, typing away mostly to myself. My next steps are to socialize the work, collect feedback, and keep iterating. I’m doing this in two ways:

1. Another challenge - I’m setting a goal to publish 10 posts on Substack in December. A TenPoWriMo, if you will. Some, but not all, will be content from November edited into blog-shaped objects fit for human consumption. I’m excited to share thoughts on product taste and designing for agency soon.

2. Another beta book - I’m putting together a 20-30 page beta book from samples, and sending it out to readers for another round of feedback.

It’s been so long. It feels like I’ve done so much, and I’m just getting started. Beyond the mountains, more mountains.

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1 - Needy programs, Niki Tonsky

Programs used to center what you need. Now software is all about what it wants from you. Requiring an account when you don’t need one, constant updating, notifications, pop-up windows announcing features you didn’t ask for. I appreciate that Niki coined a phrase for something I’ve observed all over the place.

2 - Collaboration sucks, Charles Cook

Don’t waste time in meetings and “collaboration” that doesn’t improve the product or lead to decisions. Instead, be a driver. Ship things yourself.

3 - Seeing like a software company, Sean Goedecke

This article brought clarity to = everything I’ve puzzled over about annual planning processes. Engineers love efficiency, legibility runs counter to efficiency, but legibility delivers utility when planning, making tradeoffs, and securing long-term enterprise deals. Seeing through the lens of legibility clarifies decisions up the ladder.

4 - A list of every interaction concept, Anthony Hobday

As a hoarding digital goblin, I gotta respect a quality collection like this one. A superb resource for thinking about how users think about interaction design. Props to Anthony for putting it together.

5 - If your product is great, it doesn’t need to be good, Paul Buchheit

A classic from the engineer who built the prototypes for Gmail and Adsense. An antidote to “more features = better” thinking. Instead, pick three key attributes or features, nail those things, then forget everything else. If you knock the core feature out of the park, users will overlook and forgive more than you’d expect. By focusing, you’re forced to find the true essence and value of your product.

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Got a recommendation for something I should read? Drop it in the comments!

Attention

Banner blindness - People ignore elements similar to a common pattern if they’re not interested in that type of content, even if they aren’t sure what that content is.

Color - Stand-out colors grab people’s attention.

Doherty Threshold - People’s attention and productivity increase when interaction response is within 400 milliseconds.

Focus - Interfaces should contain the information needed and nothing more.

F-Pattern - Users scan web content in an F-shaped pattern, reading the first lines fully, then scanning down the left side.

Inattentional blindness - People might not see something they’re not looking for.

Jakob’s Law - People spend most of their time using digital products other than yours.

Novelty bias - People pay attention to new things.

Scanning - People look for information quickly. Information and interfaces can be designed to make scanning easier.

Visual weight - Attention is drawn to items with the most visual weight.

Z-Pattern - On pages with less text, eye movement follows a Z-pattern from top-left to top-right, then diagonally down and across.

Communication

Anticipation - Products should communicate with knowledge of what comes next.

Context-specific communication - Communication style should suit the context people are using the software in (for example, Mailchimp stops being jovial when there are problems or error messages).

Denotative color - Colors are assigned a specific meaning, either culturally or by the design.

Empty states - Empty states should communicate well with the user.

Preview changes - Show users previews of changes in real time and how the action will affect something as they consider options.

Status visibility - The product should keep users informed about what is going on.

Useful animation - Animation can help the user understand how the interface works.

Complexity

Bloat - Bloat is a function of too many features for too little cognitive space.

Combinatorics - If two or more sets of elements can be combined, then you have to account for X * Y total potential outcomes.

Discoverability - There should be ways for users to explore and discover how the software application works on their own.

Four methods of simplification - Remove, organize, hide, displace.

Halstead complexity measures. The higher the number of inputs, the amount and depth of nested elements, the types of actions available, the higher the complexity, the potential branching logic paths, the higher the complexity. The previous sentence would score quite high.

Law of Prägnanz - People interpret groups of complex and ambiguous shapes in the simplest form possible.

Operational simplicity vs perceived simplicity - Working simple vs. looking simple. These can be at odds.

Simple & powerful - Products should be simple enough for novices and powerful for experts.

Tesler’s Law - A system’s complexity cannot be simplified beyond its condition to function. Simple interfaces require complex code.

Context

Affordances - The design of a thing should tell you how to use it. For example, a form field for postal code should only be long enough for 5-9 characters.

External consistency - Things should behave similar to examples outside of your design.

Familiarity - The design should speak the users’ language and follow real-world conventions.

Internal Consistency - Words, actions, and other affordances should have consistent meaning.

Pre-attentive processing - People unconsciously take in information about their environment before they take it in consciously.

Copywriting

Document - Build a product that doesn’t require documentation, then document it anyway.

Grouping - Group similar items or action under group titles.

Inverted Pyramid - Present the most important information first, followed by supporting details.

People don’t read - Assume people don’t read the text in software.

Readability - Use typography that ensures your text is readable in your interface.

Specific actions - Actions should be specific so the user knows what will happen.

Decisions

Choice overload - Too many options hurt users’ decision-making ability. How they feel about the experience as a whole can be impacted as a result.

Deferred choices - If actions aren’t required now, they should be possible to leave until later.

Hick’s law - The time it takes to make a decision increases as the number of choices increases.

Smart defaults - Make the right thing easy and the wrong thing hard.

Errors

Emergency exits - Users can quickly correct mistakes or backtrack on choices.

Error prevention - Prevent errors where you can and provide clear feedback when you can’t.

Error recovery - Error messages should provide a solution.

Graceful degradation - When errors or failures occur, the system should continue to function in a reduced capacity rather than failing completely.

Worst-case design - Interfaces should be designed to cover the worst-case scenario.

Forms

In-line errors over global errors - Better to show errors in proximity to where they happened.

Labels over placeholders - Placeholders disappear, are not accessible.

Mark optional or required fields - You don’t have to mark them all but mark one or the other.

Radio buttons vs. Checkboxes - Radio buttons are single select, checkboxes are multi-select

Validation - Include logic to check that a field has been filled out correctly.

Interaction

Buttons vs Links - Buttons take actions, links go places

Confidence - The user should have confidence that performing an action will have the outcome they expect.

Control redundancy - It can be good to have multiple ways to perform an action - i.e. a keyboard shortcut, a button, a menu item.

Fitt’s Law - The time it takes to click a target based on the target’s size, distance, and position.

Keyboard-only interaction - Some people interact with software with their keyboard only, either for accessibility or power-user reasons.

Object permanence - Objects should not appear and disappear as if by magic, it should be made clear why they did through animation, layout, or some other tool.

Postel’s Law - Be liberal in what input you accept from the user, and limited in what you ask of them.

Principle of Least Astonishment - Systems should behave in the way users expect; surprising behavior should be avoided.

Simulated physical interaction - Items moving with momentum can help communicate how the application works.

Layout

Cause-and-effect - It should be clear what changes an action caused to happen.

Conditional elements - Hide elements if they are not relevant to the user.

Control proximity - Controls should be near what they affect.

Law of common region - When elements are positioned together within a region or boundary, the user perceives those elements as belonging together.

Law of connectedness - We assume elements connected by color, lines, frames, or arrows are part of a related group.

Law of Continuity - The eye follows lines, curves, and sequences of elements.

Law of Proximity - Similar items should be closer, unrelated items should be further apart.

Law of similarity - Elements that look similar will be perceived as being a related group.

Memory

Miller’s Law - People hold an average of seven things in their working memory they can identify.

Negativity bias - People remember bad experiences more than the good. The bad feelings of losing $20 is stronger than the good feelings of winning $20.

Recognition over recall - The machine is the user’s memory, not the other way around. A GUI lets you recognize commands, a CLI requires you to remember them.

Serial position effect - Users are most likely to remember the first and last items in a sequence.

Spatial memory - People remember elements by their position.

The Von Restorff Effect - One visually unique object will be remembered among a group of visually similar objects.

Zeigarnik Effect - Uncompleted or interrupted tasks stick in people’s memories more than completed tasks. Give users ways to track incomplete tasks in-app so they don’t have to do it in memory.

Speed

Doherty Threshold - Productivity soars when a computer and its users interact at a pace (<400ms) that ensures that neither has to wait on the other.

Immediate Feedback - Systems should respond immediately to user actions to maintain flow and confidence.

Latency - People assume a system is lower quality if interactions take more than 100ms.

Parkinson’s Law - A task expands to fill the time allotted for its completion. Design tasks to take as little time as possible. Give users estimates on how long things will take.

Task Flows

Communicate progress - Provide users with clear progress or task status visibility to keep them motivated.

Escape hatches - Provide the user with a way to abandon what they are doing.

Goal-Gradient Effect - The closer a user gets to a goal the more motivated they are, and the faster they move to complete it.

Incremental construction - A person might need to start on something now, add to it later, work on it over time, etc.

Midstream task change - Sometimes people change what they want to do in the middle of doing it.

Minimize clicks - Reduce the number of clicks & actions a user needs to complete a task.

Progressive disclosure - Display things in stages instead of all at once.

Remove steps - Steps the user shouldn’t have to take should be removed.

Save progress - Provide the user a way to save and come back to a task in case they get detoured.

Streamlined repetition - If something needs to be repeated it should be possible to repeat it endlessly.

Quality

Aesthetic-Usability Effect - People are more tolerant of minor usability problems when an interface has an aesthetically pleasing design.

Paper cuts - Lots of small usability issues add up to a negative experience.

Peak-End Rule - People judge experiences mainly on how they end.

Sturgeon’s Law - 90% of everything is crap.

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Sources

1. Nielsen’s 10 Usability Heuristics for User Interface Design

2. Every Interaction Design Concept

3. Laws of UX

Good recommendation game

There’s an art to making good recommendations. If you want people to appreciate what you’re giving them, you need good recommendation game. You make recommendations valuable by making them specific and unique. Recommendations are something of a homework assignment. You owe it to the recipient to put in some effort on your end.

A recommendation is more likely to land if you:

• Explain why you’re recommending this thing in this context

• Summarize the value and explain why it’s worth their time

• Call out a specific feature or pull an excerpt of what you’re recommending

• Recommend one onboarding piece instead of an artist’s catalog or YouTube channel,

• Share a list of 3-5 items. Telling me you have “60 AI tools I should add to my dev workflow” tells me nothing

• Give them a ‘hook’ that explains how your recommendation connects to their interests or work

• Give a comment that helps the OP explore their original idea further, or asks an interesting question of them.

A couple of threads worth reading on recommendation game: 1, 2

Be a tour guide

We are smothered by infinite content. People are hungry for guidance on what’s worthy of attention. They want help finding the top 1% among the slop.

You can be a tour guide by sharing your best finds. You can help others navigate. Recommendations are a public service. Doesn’t have to be a comment or convo, can be a post, that helps people without you even realizing it.

The Call to Action

Send me your reading lists! Your playlists! Your books, articles, podcasts, songs, and videos that had a profound impact on you. The ones that changed rewired your brain. Made you feel alive.

Tell me why. Practice writing an impactful recommendation in the comments. 👇

The story so far

My goal was to create a ‘beta book ': a 20-30 page version of the book that I could send to a few beta readers for feedback. After a lot of writing, I ended up with 60 pages of content.

Roadblock 1: Initial beta doom loop. Working on something that large, for that long, and showing it to someone in a messy, unfinished state is terrifying. I spiral between “it’s not good enough” and “this isn’t fast enough.”

Eventually, I printed out the book, went over the whole thing with a red pen, and worked it into something I was comfortable showing people. The physical book set a good boundary. Editing in paper is more taxing than dragging and dropping digital blocks. Whatever came out of this phase, I decided that was the beta book.

The feedback

I was able to find some wonderful people who were willing to take the time to provide honest feedback. (You know who you are, much love ❤️).

Beta reading was painful and indispensable. Design is a collaborative process, and writing a useful non-fiction book is a design problem.

Key points:

1. More case studies, more examples, more exercises. I need to do a better job of painting a picture and putting the principles into action

2. Some topics were underexplored, such as taste and social responsibility.

3. I need to spend more time explaining and clarifying complex ideas, like the recognition-primed decision-making model

sticking point 2: The pile of grist? Grist is the raw material from wheat that is processed into flour and other useful commodities. I am sitting here with 60 pages, 133 notes, comments, and an ever-growing pile of articles, papers, books, and videos to sift through for research. I am buried in grist.

How in the world am I going to get from here to a polished 150-250 pages, which is my goal? I feel like I signed up for a marathon and just hit a wall on mile six. It has felt overwhelming thinking about how much further I have to go.

The plan

Stop overthinking, start anywhere. Same monster I’ve fought all. year. I’ll start cleaning up small mistakes, adding new information as I discover it, and applying the feedback I’ve received so far.

Focus

I am going to double down on the sections that are working and cut on the ones that aren’t. I’ll dive deeper into building product intuition and collaborating with others. I’ll cut back or reduce the focus on things like prioritization and estimation. That content might end up as content on this site.

Interviews

I am going to reach out and interview product-focused engineers, product managers, and designers across a variety of companies. This will help me collect more case studies and cover blind spots.

Read the canon

I heard (obviously false but truthy) that if you read the 4 books on the canon of a subject, you’re more knowledgeable about that subject than 98% of people. So, figure I need to start by digging into the most often recommended books on my subject:

• The Design of Everyday Things

• The Mom Test: How to talk to customers & learn if your business is a good idea when everyone is lying to you

• Inspired: How to Create Tech Products Customers Love

• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days

• The Lean Startup

Collect

I love hoarding examples and frameworks like a little digital goblinLook, I already made one, a small but mighty reading list of the product thinking canon!. As I go, I want to build reference materials on product thinking models, usability heuristics. Like when Anthony Hobday made a list of every interaction concept.

Want to help?

DM or email me if you’re interested in being a future beta reader. Or if you know any product-focused engineers who have a story to tell, I’d love an intro :)

Also, if you want to have a conversation about product thinking, taste, why engineers should care about this, or the obligations engineers have to their impact on society and the world writ large, reach out via DM or email, I’d love to have an interesting conversation!

The more interesting conversations I have, the better the book will be in the end. Hell, having an excuse to kick off interesting conversations is one of the reasons I started this project.

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Where we are today

The biggest day-to-day change has been in *how* coding gets done. My workflow is entirely different now. I use CLI coding agents, primarily Claude Code. It writes code, runs scripts, and manages my version control. It’s a plain-text search engine of the codebase and its git history.

There’s also a shift in the wind of how companies are thinking about AI as a skill set. Zapier released an AI fluency matrix, and I think you’ll see more companies using rubrics like this.

The changes I’m seeing

1. The skill economics are shifting

The value of writing code is decreasing. The value of reviewing code, writing specs, system design, and defining processes is going up. Invest accordingly.

There’s also AI fluency as a job skill. If you’re on the job market, you need something on your resume about your LLM expertise.

2. It will only get tougher to break into the industry as a junior

It’s already tough out there for junior developers. LLMs are raising the bar on what’s expected. Whether LLMs affect productivity is irrelevant here. It’s whether people in charge of headcount budgets *believe* it can increase their value-per-developer-dollar. Companies will expect more from juniors for less, and I think they’re in for a rough decade. The industry could also face a shockwave of an expertise gap in 5-10 years because of this.

I could see a world where the job of a junior developer is to act as a mini-conductor, babysitting coding agents. The ones out there figuring out how to leverage new tooling will be in a great position.

3. It’s going to get harder to climb the ladder as an engineer

Even if you find a job, getting promoted isn’t going to get any easier. Previously, you could climb upwards by increasing either the complexity or the scope of your tasks. You moved from thinking at the ticket level to the feature level, and then to the multi-person project level. But with code being devalued, engineering skills are no longer enough to climb the ladder.

4. LLMs will improve the code quality of large codebases

LLMs reward good engineering practices: Well-organized code, automated tests, comprehensive tech specs, documentation, smaller, coherent files, and choosing standard technologies over shiny new toys. All of these will make using LLMs more effective in your project. Turns out when you make your codebase dead-simple to work with, you can get a lot out of a dead-stupid computer. LLMs can compound tech debt just like they compound productivity.

5. The quality of software will barbell

Creating slop is so fast and cheap now. Slop is not an AI-exclusive phenomenon. Slop means you didn’t try. People can tell when you don’t try. Now, not trying can produce more than ever before. I see this in writing already. Skilled writers can research more quickly and produce high-quality work faster.

There will be more crap. A lot of it. But there will also be people who understand the tooling and use it to create products at a quality that wasn’t possible before. LLMs will enable the best and worst of software.

6. We gotta stop saying ‘vibe coding’

‘Vibe coders’ are an evolution of ‘Code Monkeys, ’ a derogatory term for people churning out work with little thought to quality or craftsmanshipHelluva Jonathan Coulton song though.. There is a distinction between “vibe coding” by people who don’t know what a “tech stack” is and people who are implementing LLM-based practices into their software engineering jobs. Simon Willison tried to call that Vibe engineering. Great article, despite replacing the wrong word. This graphsource: Vibe code is legacy code from Maggie Appleton sums it up nicely:

This is not to disparage vibe coders. It’s a lot of fun! I can’t hate a technology that enables more people to express themselves and make more things.

7. It’s gonna get weirder

Now that code is cheaper, and the tooling thrives on smaller projects, and more people can create more things, we’re gonna get weirder shit. Everyone can build a todo list how they like it. Everyone can make a game that caters to their taste. People with strongly attuned taste will build products they’ve always wanted. Companies will spin up internal tooling to solve their domain-specific problems.

These programs live behind VPNs and on people’s hard drives. A million dark matter applications.

Excited to see what happens next

I’ll check in with y’all in 2027, see how I did. Till next time 👋

1 - Seeing yourself

That’s the question by ‘Autotranslucence’ in Becoming a magician. They talk about “magicians:” people who are operating at a level that they cannot fathom. At first they were boggled by these people’s existence, then they realize they could become more like them. Someone different. That is, if they were willing to make the change.

It sounds like an empowering question. But if you’re like me, it also sounds frightening. Becoming someone else means, in some sense, the death of the current you. Habits, stories we tell ourselves, even relationships might disappear when we accomplish a metamorphosis. Butterflies have to leave their caterpillar form behind. There are new stories and friends on the other side. The butterflies are okay. But it’s hard to see that far ahead.

Being yourself is hard work

When I was a middle school outcast, I incessantly heard the refrain “just be myself.”

Terrible advice.

The implication was that I was perfectly fine as I was, and if people didn’t like it, that was their problem. “Myself” was the default state. Why should I have to put in effort to “fit in?” It was told with good intentions, but all I internalized is “why do I have to be myself if I hate how that feels?”

Later I discovered that “Being yourself” is hard work. It requires asking yourself hard questions. Curating your taste. Shaping your voice. Learning to enjoy your company. Living in accordance with your values. To be yourself you have to build yourself. Being yourself is a choice, a chore, a burden, a gift.

Understanding who you could be and who you are today are the same question. It’s Current You who wants to be New You. Why do you want it?

I feel slightly sorry for people who have never had the opportunity of a mental health crisis. Depression teaches that you are not your thoughts. Addiction teaches that you are not your desires. There’s no better way to learn that you can change who you are than by being in a situation where not doing so means your untimely death.

But once you’ve decided you want to move in a new direction, how are you going to take the next step?

2 - Exploring all possible options

I’ve really been enjoying Cate Hall’s recent work about agency on her Substack Useful Fictions. It started with her first post, How to be More Agentic, but the one I found most useful, and her top post, is Maybe you’re not actually trying.

Cate posits that we bring unequal amounts of rigor to different parts of our lives. Imagine a staff engineer who has a robust issue tracking system at work, but then when they go home to cook dinner, it’s chaos. They get hungry and have to make yet another DoorDash order, because after three trips to the store they still lack all the ingredients to make dinner. What if you applied maximum resourcefulness to every aspect of your life?

Think deeply about every option you have available. Ask yourself and others questions.

Making change means expanding our collection of all possible options. Expanding our possible options means expanding our definition of our own capability.

I’ll use myself as an example: I have written online since 2008. I have never managed to maintain a consistent content calendar. I could say it’s because I have a 9-to-5, a family, and an aging body to take care of. But have I explored every option? I could schedule and stick to more writing blocks. I could write and maintain a backlog. I could offer to donate $50 to a cause I hate if I don’t have at least one new post a week. I could lock myself in a cabin and not leave until I had a three-month backlog. I could schedule a draft post to go out and then it’ll ship whether I’m done or not. There are more strategies I’m sure. I could ask other writers how they do it. I could do more research on strategies that have worked for others.

Truth is, either consciously or not, I don’t want to.

If you don’t know what to do next, then you have to take a step back and realize that you can do something about that. Start anywhere, or do some light strategizing.

I guarantee whatever problem you’re facing, you have more options than you realize. Is it possible you committed to one option too early and wrote off other options? Things you’re allowed to do is a fun list to scroll through for inspo. Sometimes we need a reminder that we’re allowed to ask for help or throw money at the problem.

3 - Overcoming resistance

In The War of Art, Steven Pressfield describes the internal battle taking place inside all creatives between the Muse and the Resistance. The Muse pushes you to create, to grow, to venture into new frontiers. But the Resistance tries to stop, scare, over analyze,distract,deflect, and demoralize.

The more you take on, the more Resistance you find. This is the challenge of agency. It’s often less about “taking more intentional action” and more about “getting out of your own way.”

The trick is to learn to fight through the resistance, no matter how difficult it feels. Like a video game, the fights get harder the further you progress. I try tp develop a taste for battling Resistance. It’s a sign I’m moving in the right direction.

If you’re not careful, you can fall prey to Resistance Psychosis and start confusing Resistance’s words for your internal monologue.

These aren’t your thoughts and they are not valid.

If you hear any of these in your head, attack them and question their validity. Resistance dies in daylight.

• I can’t do this.

• I shouldn’t do this.

• I don’t have permission to do this.

• I don’t deserve to do this.

• I’m not the kind of person who does this.

• This is too risky.

• This isn’t my fault.

• This isn’t my responsibility.

• I have to do something else instead.

• I don’t have the {time, money, energy} for this.

• I’m not {good, smart, rich} enough for this.

• I’m scared I’ll never achieve this.

• I’m scared of what would happen if I did achieve this.

Obviously, You cannot and should not do anything. There are physical limitations and moral codes. But when you run into a limiting belief, it’s worth examining. What’s stopping you here?

One way to tackle these objections is to act as if the opposite were true. Looking at the problem differently can unstick you.

• What if you can do this?

• What if you are the kind of person that does this?

• What if you did have the time, the money, the resources?

• What if you made time for this?

• What if it’s worth the risk?

• What if you got started right now?

• What if it’s actually easy?

• What if it was your responsibility?

• What if you’re already enough?

But sometimes it doesn’t feel like a fight. Instead it feels like being stuck in a bog. In So you wanna de-bog yourself, Adam Mastroianni lists out several anti-patterns of feeling “stuck.” A quick summary:

You shouldn’t have to work on this problem anyways. It’s not your fault. Or it’s too big to handle. And even if you want to tackle the problem...

You can’t get started because you haven’t found the perfect solution. Or you don’t understand the problem enough yet. You’re waiting for the day you tap into that magical well of discipline you’re sure you’ve stowed away somewhere. And even if you did know what to do...

You have enough obligations on your plate already. Or you’re too concerned with the state of the world. (Solutions, in this economy?) Or it’s too scary to get started.

All of this comes from your ego’s survival instincts. If you change, it dies. Resistance is that lesser part of you, having an extinction burst. It’s doing everything it can to prevent you from acting different and becoming someone else. Resistance is the part of us that would rather stay as we are than be who we want.

4 - Taking action

Introspection is fun, but useless if you don’t put it into action.

There’s a distinction between exercising agency and biasing towards action. Agency is about effecting change, which means taking actions that get results. “You can just do things” does not mean “go do anything.”

It’s not a bias towards action, it’s a bias towards results.

Agency compounds

Action is key. Action produces information. Pay close attention while you’re doing the work. The work will teach you about yourself, about who you want to be. It’ll open more options, build your confidence, and help you get unstuck.

The more you do this, the stronger you become, and the easier it gets. You will gain more capabilities, more self-knowledge, and more confidence, and move closer to the next iteration of you.

And now, a moment of Zen

Just beyond yourself
It’s where you need to be
Half a step into self-forgetting and the rest restored by what you’ll meet
There is a road always beckoning
When you see the two sides of it closing together at that far horizon and deep in the foundations of your own heart at exactly the same time,
That’s how you know it’s the road you have to follow
That’s how you know it’s where you have to go
That’s how you know you have to go
That’s how you know
Just beyond yourself, it’s where you need to be
— David Whyte

Bibliography

• Becoming a Magician - Autotranslucence

• Stanford encyclopedia of Philosophy entry on agency

• Musings on teaching agency - Chana Messinger

• Thread: High Agency Questions - Chana Messinger

• How to be more Agentic - Cate Hall

• Are you even really trying? - Cate Hall

• Things you’re allowed to do - Milan Cvitkovic

• So you Wanna De-Bog Yourself - Adam Mastroianni

Writing increases your luck surface area

Writing is a social practice

On social practice, DMs are always open to other writers who want a second set of eyes on a draft, or just want to riff on ideas.

Writing can generate interesting conversations, create new connections, and strengthen existing friendships.

Writing can be an act of service. Write things that help others. Write for an audience of one, then send them something via DM.

Writing is a long-term game

When looking for jobs, or thinking about a new product, or anything else, you always wish you had written more. This isn’t something you can do just-in-time; you need to do it before it’s time. It’s a game with short-term risk and long-term payoff.

Writing pieces are assets. They can and have led to landing clients, getting speaking gigs, and getting jobs.

Intrinsic benefits of writing

Writing codifies your ideas, then you can communicate them more clearly. Everyone else is out there talking in first drafts.

Writing helps you develop a voice, a tone, a style.

Writing is a form of learning. The best way to learn something is to explain it to others.

Writing is an infinite craft. You can stop improving your writing in the same way a pro golfer can hit an 18. In a fast-moving world of technology, writing is an evergreen practice. I will write until I’m no longer able.

Writing is an exercise in getting thought plaque out of your head. It’s good for your mental health.

On writing prolifically

Further Reading

• Good X thread: If you have a technical blog, and it’s brought you some positives (job-related, social, etc.), and you don’t mind your tweet being screenshotted, I’d love to hear about them.

• Tom Critchlow - Small-b blogging

• Henrik Karlsson - A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox

Use LLMs to inform, not decide

Don't ask "What should my next career move be?" Instead, ask "Give me examples of career strategies for people in my scenario." LLMs gather information, humans make the call.

One big source of alpha: CLI-based tools like Claude Code and Codex as plain text code search engines. Customer support asks, "Do we have a setting to disable the transaction email with {subject line}?" I work for a company whose backend is written in Haskell, a unique language with a steep learning curve. A curve I've never bothered climbing. Now I have a much easier time understanding how things work.

Use LLMs to edit, not interpret

LLMs excel at data transformation. LLMs are great at turning text from format A to B. Haskell to English. Code to customer support. I've used it to generate plain English summaries of JSON objects. You can take a screenshot of anything and turn it into text or a CSV.

Now that I'm in a more managerial role and writing on the side, I find this kind of 'text scripting' incredibly useful. These are cases where judgment calls aren't needed. When it is, I find a way to stay on top of the process.

I don't trust LLMs to write; they lack voiceUnless it’s writing some TPS-report corpo-content, where removing voice is a feature, not a bug.. Instead, when writing this piece, I will have an agent copy a draft, then make edits based on a style guide. Afterwards, I diff both pieces and put together a final version. Fewer mistakes, more humanity.

However, I would be wary of using it for summarization. Some text processing is sneakily a value judgement: You are deciding what to include and what to omit. What to emphasize and what to downplay. You are also making decisions about structures and prioritization. These are the kinds of writing work I wouldn't outsource to an LLM.

LLMs don’t always write good code, but code doesn’t always have to be good

Tell me if this resonates: You see the hype around AI delivering developer productivity gains. You see the takes on social media calling it bullshit. You try it at work. The result? A tool that ignores instructions, reimplements existing code, churns out slop. You spend more time writing prompts and reviewing than coding. You've hit the paradox of automation.

The faster code can be written, the more crucial human judgment becomes. Real savings come from code that requires less judgment.

Day job code requires working with a large codebase and trying to achieve a specific result. It requires subjective judgment on which parts of the codebase are important, and what the output should look like.

Sometimes code doesn't matter much. Prototypes. Command line utilities. Utility scripts cost nothing now. CLI-based LLM tools write and run them. Contrast coding at work with "vibe coding," an app, where you care less if the final outcome is a little different than what you were expecting. It's all jazz, baby.

LLMs drastically changes the math on automation.

I think I could whip up any single-purpose script in 30 minutes or less. Automation costs roughly a pizza.

The biggest gains aren't in optimizing existing workflows. They're expanding what's possible. With a tool that writes & executes scripts, what wasn't worth doing before?

Product engineers and designers can now open PRs to production. Should companies encourage this? Why or why not?

You get out what you put in

From Taste is the new intelligence: "what you consume, what you engage with, what you amplify—becomes a reflection of how you think."

Curation is a part of self-expression. Part of being yourself is curating your taste, which requires being intentional in what you read & watch, and reflecting on what resonates with you and why. What you consume shapes how you think. Output is a function of input.

Less junk

Remove as many ads as possible.

It's worth upgrading streaming services. Judiciously unsubscribe from email spam. Set up ad blockers or a Pi-Hole. You choose what you consume, not corporations. Gentle reminder that advertising works on everyone, especially people who think it doesn't work on them.

Keep your follows small and high quality.

You should avoid social media, but when using it, keep the number of accounts you follow small and high-quality. Don't let noise fill up your feed. You choose what you consume, not influencers. They are called influencers for a reason.

Have an outcome-focused approach to content

If you want to be entertained, watch entertainment. If you want to learn, study. Don't half-assedly listen to a podcast while you're doing dishes and tell yourself you're "learning." The whole genre of "infotainment" exists for the smart person who likes the feeling of learning, regardless if they retain any useful information. No judgment, liking that kind of stuff, I do, but I'm honest with myself that it's for entertainment purposes only.

More nutrients

Prefer Lindy content

If you had to guess, what percent of content you consumed today is less than one year old? Less than one month? Prefer content that has a long shelf life and took a long time to make. Books and essays over tweets and vertical videos.

Prefer uncommon content

Forage for cult-classics and hidden gems. More obscure sources lead to more original thinking. Hideo Kojima got ideas for the tone of Death Stranding from an album he found in an Icelandic record store. He hired the band to work on the soundtrack. Breakout videogame of 2025, Clair Obscur: Expedition 33, is heavily inspired by a French sci-fi novel that didn't sell enough copies to warrant an English translation.

There is nothing wrong with consuming mainstream content; it's popular for a reason. But you'll be less inspired if that's all you ever see.

Recommendations over algorithms

Ask friends for recommendations, or read books that your favorite authors reference. My reading list for the last decade has been:

1. I see a recommendation for an interesting article or book

2. If I like it, I dig deeper into articles and books recommended in the piece.

3. GOTO 1

Don't let a few algorithms decide what you're going to consume. And be part of the solution! Share more about what you love! Support small-time creators! The world needs more recommendations, fewer algorithms.

Take time to process

Take time to reflect and integrate what you've learned, instead of jumping from one thing to the next. Instead of starting the next chapter of an audiobook on an evening walk, give yourself the space to think. It's overwhelming out there. We get exhausted if we don't give ourselves space to process all that we've seen.

Motivations matter

To create a quality product experience, you must be attuned to your user. You need to be able to understand and feel their mental and emotional context, even if you can’t articulate it.

Your motivations show in your work. People can tell when a page was designed to help them, and when it was designed to manipulate them. AI has led to a proliferation of more and different kinds of slop, but slop has always existed. The question isn’t if something is AI-generated or not, the question is whether or the person who created it tried. People can tell if you tried.

Every product decision doesn't need to move a needle. Making users' lives easier, building trust with them, or making them smile at a delightful surprise is enough. If you can't do this, metrics approach zero because no one will want to do business with you.

Metrics are useful, but they are not a replacement for taste, effort, or care.

Don’t serve spreadsheets, serve people

How people feel when using an application cannot be quantified. It can be ruined by putting numbers over people.

People slack on social media, and feel guilty. They read rage bait and raise their blood pressure. The iSkinner Box of random red circles feeds an undercurrent of anxiety. No one feels good after a doomscroll. Our feeds fill with vertical videos created to serve the algorithm, not the audience. They lock their phone, curse the time wasted, and do it again. Tech companies have won the numbers game, but the people have lost a piece of their hearts and minds.

Why does this happen?

People hate uncertainty and love legibility. Our lizard brains interpret uncertainty as risk and trigger unhelpful threat responses. We become less rational, more reactive. What threatens us? The consequences of being wrong. We reach for numbers to give us certainty.

The nice thing about data is its friend: plausible deniability. If you make a decision based on perception, taste, or expertise, you own the outcome. If you point to a graph, you can pass the buck. You were doing what the data drove you to do.

We like legibility because it’s simple. It's difficult to compare two versions of a product UI and know which users will prefer. However, we can ask people on a scale of 1 to 10: Would you recommend this to a friend? Then it isn't a value judgment, it's a simple comparison. A much easier question to answer.

Taste, qualitative data, are all illegible, messy, and worth it.

Metrics are signal, not strategy

I'm not anti-metrics, I am anti-metric myopia. Some things can and should be boiled down to numbers. System performance can be quantified and changes measured.

Metrics can provide insight and help identify leaks in your product and opportunities we would otherwise miss. They are one lens through which to see the world.

Problems arise when you assign numbers to things where they don't belong, or you push less measurable aspects aside because they don't fit the equation you've devised for setting priorities.

Metrics are useful, but they are not a replacement for taste, empathy, and giving a damn.

AI and skill issues

Elden Ring introduced many players to the Soulslike genre, a notoriously difficult type of video game. When newcomers complain about unfair bosses and punishing mechanics, they may be told to 'git gud.' or simply 'skill issue.' - gamer slang meaning "the problem isn't the game, it's you."

The first boss lampshades this, reminding the player after defeat they aren't yet ready for what lies ahead. New players, myself included, heard this phrase over and over and over again.

At least, they aren't ready yet.

Some people take offense at being told "skill issue." But truth is, its empowering. You can't change the game, only l how you play.

Same with LLMs.  People say they don’t get the same results others rave about, and think its baseless hype.[^1] Unlike Elden Ring, it's harder to tell what is skill and what isn't. Elden Ring is difficult, predictable, and fair. LLMs are a non-deterministic blackbox. The same prompt can give different answers, and it can be unclear why. I still don't know how to tell the difference between user error and model strangeness.

Skill issue on my part I suppose.

Defining AI fluency

If some people are better at using LLMs, what skills set them apart? What does it mean to be “good at AI”?

This internal AI fluency framework from Zapier has been making the rounds. I don’t know if I agree with all of it, but it’s a decent starting point.

Part of fluency is knowing what’s available, what tools can and can’t do, and matching the right model to the right task. Skilled operators write stronger prompts, and they also pick the best model for the problem. That’s the difference between someone typing two sentences into a free ChatGPT window, and someone who studies the different elements of what goes into a prompt. See intimidating chart:

But ultimately, I think the deeper skill is being able to figure it out. By the time the charts are made they’re already outdated. Instead of diving into byzatine documents, you have to have to just push buttons, evaluate the results, and adjust your approach.

Many AI adoption strategies fail, but not for the reason you think

I’ve seen this headline thrown around a lot: "MIT report: 95% of generative AI pilots at companies are failing"

Some people read that as “don’t run a GenAI pilot.”(AI is hype!) Others see it as “figure out how to be in the 5%.”(I gotta git gud!)

Pro tip: When people cite a "studies show X" headline, go find the study and read it your self. In today's infinite content environment, this is a superpower.

Go ahead, give it a shot: The GenAI Divide: State of AI in Business in 2025, tell me your biggest takeaway after reading it.

My take: it’s more "enterprise companies struggle to adapt to new technologies" and less "AI fails to deliver."

Losing companies are:

• Overspend on sales & marketing, underinvest in back of house automation.

• Buying expensive, tailored, inflexible GPT over generics like ChatGPT and Cursor

• Try to roll their own internal AI systems.

• Have complex enterprise processes and refuse to change them.

Winning companies are:

• Solving for learning, memory, and workflow adaptation.

• Build systems that learn from feedback and retain context/

• Invent new, high-leverage processes that leverage AI's strengths.

What stuck with me: the big wins aren’t coming from making current workflows faster, but instead creating entirely new ones.

A better question than "how can we go faster?" is "What can we do with LLMs that wasn't possible before? "

Core elements of a menagerie game

1. A varied pool of interlocking game pieces. Cards, weapons, items, anything. You draw from a random subset each game.

2. Interlocking mechanics that influence one another and generate emergent interactions and strategies

3. Combos and nonbos. Some pieces are synergistic, others antagonistic.

4. Infinite extensibility. There's always room to add new pieces and mechanics.

Being dealt a pile of random pieces and figuring out how to put them together is the core hook. The mix of puzzle-solving and discovery keeps me coming back. The randomness adds to the addiction; each run is a fresh puzzle to solve. A new space to explore.

Menagerie archetypes: roguelikes and deck-builders

Two genres of games fit into this: roguelikes and deck-builders.

Roguelikes are games inspired by the 1980s video game Rogue. In Rogue, you navigate a labyrinth of randomly generated dungeons, with random item and monster placement. While other fantasy games are 30-60 hour epics, Roguelikes are built around 30-60 minute runs. One life, you either finish the dungeon or start over with a new one.

Deck-builders are what they say on the tin. You have a deck of cards you can modify, either before or during the game. You are drawing from a random pile, but you get to have agency in the design of the pile.

Roguelikes give you a lot of different game pieces to randomize: dungeons, monsters, player stats, equipment, and consumables. Deck-builders have cards, an endlessly extendable game piece.

The three menagerie games I've had an obsession with, in chronological order, are Magic: The Gathering (the OG deck-builder), The Binding of Isaac (An absurdly funny and grotesquely horrifying roguelike), and finally Balatro (a deck-builder and a roguelike, drool).

To Magic: The Gathering, and Beyond

As of this writing, there are 30,367 unique Magic: The Gathering cards. Magic has been releasing new cards for 32 years. It doesn't get more extensible than that.

Magic cards have always represented a variety of concepts: spells, places, things, magical devices, weapons, battles, vehicles, and even reuniting with a long-lost old friend.

Magic wove extensibility into the lore. Magic takes place in a 'multiverse' with an infinite number of alternate universes called planes. This way each set can explore a new theme. Over the past 30 years they have had planes inspired by, but not limited to:

• Greek mythology

• Japanese mythology

• Indian mythology

• Fairy Tales

• Tolkien-inspired worlds

• Hell

• A world with a 600-year-long day/night cycle

• A 15th-century ecumenopolis

• A plane Gothic + Lovecraftian horror

• A plane of campy 80s campy horror

• A return to that Japanese mythology world but it's 2000 years later and now it's all cyberpunk

• Pirate dinosaur worldYes, one line, this is not a typo. There are also mermaids and vampires.

• Cowboy world. Yee-haw!

Executives at Hasbro recently had a very profitable realization: Magic's system could support not just any world, but also any IP. They could play the same game as Lego and Fortnite. Why make a Tolkien-inspired set when you can just print the Lord of the Rings set? Magic released a Final Fantasy set, and it's their biggest seller ever. making more money than many other video games and movie releases this year. $200 million. If it were a movie, it would be tied for no.8 at the box office beside Captain America: Brave New World

They are seriously trying to become the everything trading card game. The Amazon of sci-fi fantasy. 30 years and 30,000 cards later, their rate of producing new cards is actually increasing.

The Binding (and duality) of Issac

Edmund McMillen gained notoriety with his breakout hit Super Meat Boy: a platformer that dared to ask the question: "What if Super Mario Bros. was batshit insane?" His follow-up, The Binding of Issac, a top-down roguelike that dared to ask the question: "What if The Legend of ZeldaThe Binding of Isaac and The Legend of Zelda having the same meter is no coincidence. was batshit insane?"

The loop is simple: Like Legend of Zelda, there are dungeons, each with an item and a boss. But instead of an overworld, you move from dungeon to dungeon.

The lore is a little more complicated. It's an allegory to Genesis 22. The one where God asks Abraham to sacrifice his son Issac, then at the last minute says 'jk' and merks a ram instead. In the game, Issac's mother believes a televangelist ordered her to kill her son. Isaac flees to the basement, which happens to be a cascade of procedurally generated dungeons.

Power-ups are all over the place. McMillien includes references to anything and everything, including:

• in-game lore

• His previous games (Super Meat Boy, Time FcukAlso not a typo.)

• His favorite games (Magic: The Gathering)

• The Bible

• His dead cat (RIP Guppy)

It's whiplash. The game swings from funny to tear-jerking. Horrifying yet goofy. While playing, you reflect on how Christian upbringings can fill children with a deep sense of guilt and shame, then collect a power-up that's a fart.

Balatro, the genius of Joker Poker

In Balatro, you play sets of poker hands and must hit a minimum score to advance to the next round. Every round, the minimum increases. Between rounds, you earn money and visit a shop where you can spend money to acquire jokers (permanent modifiers), one-shot items, new cards for your deck, or planet cards that increase the point value of specific hands.

Watch on YouTube

Just like in poker, hand strength matters, but it's a small factor. Balatro's randomly generated dungeons are not the rounds; it's the shop. The shop gives you a limited number of options and 5 joker slots, which is your primary way of building your strategy and increasing your score.

Then there's also the deck-building. You start with a standard 52-card deck, then add, remove, and modify cards in it. If you have a joker that rewards hearts and another that rewards flushes, you can bias your deck towards hearts. If you have a joker that punishes face cards, you cut as many of them as you can. One of the most optimal decks is often 40 enhancement-packed kings of a single suit.

Building my menagerie game

In my last post, I mentionwed how another Substack post inspired me to build my own roguelike. Menagerie games are ideal learning projects. There are always new mechanics and pieces you can invent.

Add weapons. Then add elemental damage. Then status effects. Then triggers tied to player actions. Each layer asks new questions of me and of the game.

This creates an addictive, multi-tiered iteration loop:

1. I iterate on the game, adding new items, tweaking and balancing.

2. Then, I iterate on the engine. Adding new mechanics, refactoring code as the system grows.

3. Finally, I iterate on my build process. How can I leverage Claude Code to build more interesting gameplay faster?

I don't know when I'll stop iterating on this game. There's plenty else I want to build, but it's nice to have an evergreen playground that can be anything and everything. Just like Magic keeps adding expansions, there is always another weapon, monster, or mechanic to toss into the pot.

Devil's Den on Github

Playing game design with my son

I've co-designed a board game with my son, titled Dinosaur BreakoverHis name. I have no idea what a ‘breakover’ but he loved it.. At the start, you pick which of four dinos you think will win a drag race. Then, players take turns drawing cards from a deck until one dino crosses the finish line. Former college drunks like myself might recognize this as a family-friendly riff on the drinking+gambling game Horserace.

What it lacks in complexity, it makes up for in how much watching my son draw his new card idea warms my heart. The deck contains various references that I put in and his ideas.

As he grows, maybe we can extend the lore and the mechanics. Make our own expansion packs.

One time, we sat down to play, and he asked:

Great question, big guy. What if it did?

Diving headfirst into Claude Code

At first it felt daunting. What project should I build? Which model? What belongs in my local CLAUDE.md file? How will I verify correctness? How do I prompt it? I’d stall there. I even keep a note with twenty “LLM Project Ideas,” yet when I sat down, I didn’t know where to start. After the episode, I figured, “start anywhere!”

I had a few changes I wanted to my personal homepage. I use Claude Code and it was able to get the job done! I wanted to try something bigger. Then, I stumbled across this post: “The 7-Day Roguelike That Took Six Minutes.” Perfect! I love roguelikes, and this is a decent sized greenfield project.

It took hours, not minutes. When I got stuck, I read docs and searched for answers. I kept a running list of open questions and filled them in as I went. I wasn’t “studying for someday” anymore—the mythical day when I’ll “have time.” As a parent, the only thing more fantastical than a dungeon of skeletons and orcs is the idea that time will appear out of nowhere. I was looking for specific information to remove specific roadblocks, so I could get back to work.

The next week at work, I shipped more pull requests than I had in the previous month—thanks to tricks, tactics, and prompts I picked up while experimenting. The best way to vibe code is to vibe code. You just gotta push buttons.

Pushing buttons in fast-moving fields

Someone asked me for AI course recommendations. I said I’m skeptical of books or courses. because the field is moving fast, and LLMs are an always morphing black box. What worked last week may not work this week. By the time anything that long gets published, it’s dated. You have to get comfortable taking the path less traveled, ordering off-menu, going off-book.

There’s plenty of alpha out there if you’re willing to just push buttons.

Note taking without intent.

Your work and goals should shape what you consume and collect. Information is only useful when it’s actionable.

If I didn’t write, I wouldn’t keep an Obsidian vault. Once I asked what my notes were for, it changed what I saved and what I ignored. I started keeping more data, quotes, and personal stories—the kind of raw material that strengthens an essay.

Deciding what to keep is an exercise in taste.

It clicked when I created a separate notebook just for work. Having a notebook with a singular focus made it clear what belonged and what didn’t. Now opening that vault helps me switch into manager mode, and I don’t get distracted by unrelated information.

I reach for notes after outlining an article. I open my work vault every day and use meetings & project notes to set my intention for the day. I know what notes to save because I have a clear sense of when I’ll use it and how.

Digital hoarding

Collecting notes without intent is just digital hoarding. A quote from ‘I Deleted My Second Brain’:

You don’t need to capture everything. Some ideas are better left forgotten.

Good notekeeping includes pruning. There is a point of diminishing returns. When a note is no longer actionable, let it goI resent that I found some helpful notes from three years ago while working on an upcoming draft. Like that one time a friend asked me for a MagSafe charger in 2023, buying my box of wires gave it a new lease on life..

Lost in the system sauce

Note-taking systems are a great opportunity to do some deck chair moves and pretend you’re being productive.

I’ve tried PARAProject, Area, Resource, Archive. Another Forte-ism., I’ve tried no folders, and I’ve tried dozens of folders. It waxes and wanes, and ultimately, it doesn’t matter. As long as the notes are helpful to you, that’s all that mattersCounterpoint: I am currently using a variation on this system for my work vault: The CTO’s hidden notebook..

Modern note-taking apps are cursed by their inspiration. Tools like Roam and Obsidian were inspired by Sönke Ahrens’ book, “How to Take Smart Notes,” and his “Zettelkasten” — a note-taking system that revolves around paper cards and a numeric indexing system connecting them. This system easily translates to hyperlinks, but it misses the point. We have search bars.

Don’t get trapped by taxonomies. You don’t need a complex set of tags, folders, data-views, and two-way wikilinks. All you need to do is include keywords so you can find what you need when you need it.

Tricking yourself into thinking note-taking is writing.

I’ll admit, I’m guilty of this one. This is the exact kind of behavior I am trying to rid myself of when I set my New Year’s resolution. Notetaking is a means, not an end. It’s easy to get lost collecting, organizing, and refining notes—without ever shipping anything.

Work isn’t useful until it helps someone else. Writing in your notebook does not count.

Treating notes like work instead of play

Note-taking becomes more fun when you treat it like play. Don’t take it too seriously. Mess around. Give notes weird titles. Be like the kid in school who used seven different marker colors. Doodle, draw, diagram. Use your notebook to think, not just to record.

Notes as weight, not fuel

Ever opened your notes and felt dread? You keep telling yourself you’ll organize them one day. But every new entry adds to the pile.

Now imagine this: you’ve just spent a couple of hours cleaning your house. It’s immaculate. You feel proud and relieved. You feel lighter, calmer. Notes can feel that way too.

When I’m feeling down and burnt out, I have found that cleaning and organizing a physical space makes me feel better. Similarly, when I’m feeling stuck, going through notes, rearranging them, removing clutter, and finding new patterns can help me get unstuck. Your digital gardening should leave you feeling energized, not drained.

When I’m feeling burnt out, organizing physical space helps. Notes work the same when I’m feeling stuck. Rearranging them, tossing old ones, spotting patterns—it’s like clearing a mental fog. Digital gardening should energize you, not drain you.

Replacing your primary brain

One quote from 'I deleted my second brain’ stuck with me:

Writing things down can short-circuit the experience of living them. But this cuts both ways: The ‘Zeigarnik effect’, happens when holding thoughts in our short-term memory causes increased stress. Whenever I feel like I have a lot of tasks on my plate, sketching out a quick to-do list helps. Leverage your notes to clear your head for deeper thinking, then use that space.

On the other hand, we can use notes to bring back the feeling we had before, and reignite inspiration. I’ll leave you with a quote from Kendrick Lamar, about how he sees his notebook:

Take it home, Kendrick

Writing disposable software

ChatGPT sometimes gives the perfect example of disposable software: you give it a task, it writes Python code, executes it, gives you the answer. You can cajole it in this direction by explicitly saying “use python code” to solve this. ChatGPT intends for code that is only ran once. But it’s cheap and fast enough to product that it’s okay.

AI Coding shifts the answer to the “is it worth the time?” test. More often now, the answer is “yes.”

I wanted to build out a tool for writing my product thinking book: at this stage of editing I am constantly adding, removing, and rearranging entire sections. I wanted to keep each in a markdown file, and then assemble an ebook based on a table of contents file. Claude code was able to whip this up for me in about 15 minutes. Otherwise, I’d have slogged through a verrrry long Google Doc.

I could see a lot of my writing projects looking like this in the future: repositories that are a mix of markdown files and Python scripts that help with formatting, data viz, etc.

Disposable software sidestep’s AI codings biggest flaw: the code is often ass. Keurig coffee will never beat a hand-pulled espresso. But here, quality is irrelevant, only results matter. It’s like the hotel room coffee on a business trip, the one you make in your Keurig. The on you drink to muster the energy to venture into sunlight in search of a decent espresso.

Disposability is a feature, not a bug

Trying to make disposable software production ready is a trap. Someone tried to make Vibe Coding Enterprise Edition and it did not work. This is why I like this method for prototyping. Another trap I saw back in my coding days was someone taking a weekend prototype, and then trying to evolve it into a real app, instead of starting from scratch.

Putting it into practice

As you go about your day, take note of rote tasks you could automate. Jot down small product ideas. When writing prompts, consider your options. You could ask ChatGPT “hey solve this for me” or you could say “write a python script that solves this for me.” Maybe it’s even something temporary, like an application to help you manage your Christmas shopping.

Then depending on the scale, you can later try to one-shot them, or go through a full vibe coding cycle of spec → write → review until you have something workable. It’s cheap to try. If it fails, you can always throw it away.

(This piece is part 8 of the Prompt Protocols blogchain)

So what is play?

Huizinga defined play as free, unstructured activity that exists apart from ordinary life and creates its own order. He also introduced the idea of “the magic circle”—a specific space and time where the game exists which dissolves when the game ends.

For example, when I play pretend with my son, Magna-Tiles become houses, cars, and sushi restaurants. When we stop, they go back to being colorful connectable polygons in a bin.

The forms of play

Huizinga observed that play manifests in many forms:

1. Joking & jesting - Humor bends expectations and opens up shared space.

2. Child’s play: What Maria Montessori called “the work of the child.” Also observed in animals.

3. Competition: such as sporting events and board games.

4. Pretend play: Improv, acting, & mimicry.

5. Rhythmic play: dance, music, poetry.

6. Imaginiation: Mythmaking & storytelling.

The benefits of play

Huizinga viewed play as foundational to the human experience. It gives us so much:

Play builds community

Play isn’t a part of a culture — it creates it. Take professional sports for example: teams compete for a win, but also for the right to be celebrated. Fans join in too, sharing in joy or heartbreak with friends and strangers alike. (Fun fact: “praise” and “prize” share the same latin root.)

Play increases flexible thinking and problem solving.

As Visakan Veerasamy points out, people often come up with their cleverest ideas when they’re joking around.

Play teaches emotional regulation and perseverance.

Setbacks don’t sting as much when you have a lighthearted approach. And when you’re enjoying what you’re doing, you’re more likely to stick to it.

Play increases engagement

When you approach things as play, it’s easier to stay engaged, bringing more attention and energy to your craft.

Weaponized Play

Play is powerful, so obviosuly people will twist it for profit—and the results aren’t always good.

One common example is making work more “gamelike.” But play and games aren’t the same thing. Games are just one form of play—they have rules, goals, and structure. Sometimes game-like ideas are useful, like when we “level up” our skills or follow a “skill tree” to build knowledge. But they can also be harmful.

Gamification considered harmful

Gamification is adding game mechanics to systems with the element of play stripped away. Think leaderboards, quests, achievements, unlocks, and XP to drive behavior. It is psychologically manipulative. Uber rolled out a “quest” feature for drivers, offering bonus cash for hitting milestones. But as drivers got close to their goal, Uber would feed them lower-paying rides, keeping them behind the wheel longer. They are out driving, eyes burning, concentration fraying. Uber is helping driver’s have fun it’s putting them and others at risk to increase profits.

Gamification can have positive effects too. I used to go to a CrossFit gym, fully aware that CrossFit is just gamified workouts. But it worked: it kept me coming back and got me in better shape.

When you see gamified systems, you should stop and ask: What behaviors is the system pushing? Who benefits most from them?

Why gambling breaks some people

Gambling is another example of play gone awry. It’s subject to the overjustification effect—when external rewards crowd out internal enjoyment.

Gambling can be fun, but when done compulsively it can be destructive. Playing for stakes removes the intrinstic joy of the game, makign it worklike. In college I paid rent “playing” online poker for two years. It was miserable. It turned an activity I used to enjoy with my friends around a table into four-suited Excel hell.

Mandatory fun

At my first job, I received an email (remember those?) inviting me to the company picnic on Columbus day. It informed us that attendence was “mandatory and fun”.

Play cannot be a top-down directive. You cannot force your reports to play and have fun. Play, by definition, is free. As soon as it is put on your calendar with an objective of team building or building trust, it’s no longer play. It’s a a meeting with an above-average level of cringe.

So, How to we achieve this?

We must do what Johan called “Embodying the spirit of play”. It has to come from within. It’s about choosing to bring an attitude of play and lightness to everything to do.

Because Play in the human engine of creation. **From it, we create culture, poetry, jokes, stories our communites . Being playful brings our own best, most creative, most. engaged, more powerful selves to the world. That’s why joking about the outcomes you want, bringing the character of play, enables you to be authentic, open to new possibilities, “yes and” reality, and meme your dreams into existence.

Infrastructure isn’t free

Social media offered reach—but at the price of rising ad fees. Coding assistants like Cursor are making coding faster, but also more expensive. They are currently charging $50/mo, but those prices won't last. I’ve been thinking a lot about this quote from Geoff Huntley’s recent article:

What happens when AI prices indie devs out? The gap between what a major corporations and small teams can produce will only grow.

And there’s the creeping dependency, almost an addiction. I’m shifting from anxiety about AI writing code for me… to realizing I might not be able to work without it.

Wake up babe! New psychosis just dropped!

AI will mess with our brains in new and inventive ways. It’s a well-studied phenomenon that constant social media connection increases depression, anxiety, and loneliness in teenagers. Optimized-for-obsession algorithms bewitch us into scroll trances, draining our time and attention.

Users who use character-based chatbots also show an increase in depression, anxiety, and also increased delusion. Our caveman brains aren’t ready for voice bots that are indistinguishable from humans.

New terms are emerging—“prompt compulsion,” “hallucination anxiety.”One guy made an AI employee for his startup and then wanted to fuck it. Wonder what we're going to name that one?

Announcing DictatorGPT o4-mini-high coming this winter

AI is a dream tool for authoritarianism. he more we rely on chatbot summaries instead of exploring the web ourselves, the more centralized information becomes, and the easier we are to manipulate and control.

Social media was already powerful weapon. Algorithms took tiny impulses and magnified them into extremism. Social media made men lonelier, then build a lonely male → Manosphere → alt-right radicalism pipeline for them.

Pop-quiz hot shot!

Here’s a quick 1-question test to determine where you stand in this pipeline:

• Level 0: You have never seen this video

• Level 1: You have seen this video

• Level 2: You know other people have been politically radicalized by this video

• Level 3: You are politically radicalized by this video

Watch on YouTube

Authoritarian regimes rely on centralized media. Imagine if a chat bot was your primary source of truth. A recent hack of Grok led the bot to constantly rant about South African conspiracies. What happens when people start doing this more subtly, and on purpose?

Slop is the Fascismcore aesthetic

AI was baked into Trump’s 2024 campaign aesthetic. his Truth Social account posted AI-generated images of Taylor Swift fans and that bizarre “Trump Gaza” video.

Watch on YouTube

Any tool that empowers creators will be co-opted by extremists. We’ve seen the decline of the United States as a global super power and it looks like slop.

So what’s next?

And don’t worry—soon we’ll have AI friends on Meta, so we can enjoy the worst of both worlds.

The question of AI’s impact isn’t if, and it’s not when anymore. It’s: what the hell is this thing going to do to us?

That’s what this book is about.

It’s for engineers who want to do better work—not just cleaner code, but better products. The book I wish someone would have gifted me earlier in my career.

I’m not interested in blame, I’m interested in responsiblity. The way to make software better for everyone is for more engineers to internalize that We are responsible for outcomes, not just implementations.

The best engineers I’ve worked with weren’t always the most technically-skilled or the fastest. They were the ones who understood the whole experience. They understood that every decision had a user on the other side.

What we build matters

Every software product changes someone’s life, even if it’s only a little, even just two minutes a day. That still counts. Time and attention are finite.

Are you respecting that?

Yes, we have to balance this with clean code, and scalable systems. But those are just part of the equation. What does using our software feel like? Does it help someone solve a real problem?

We’ve all done it, so we all know it: It sucks to ship garbage. Maybe there was looming end-of-sprint deadline. Maybe we could only justify “good enough.” But it's more fulfilling to ship quality. There are few things more human than helping others by thoughtfully creating something useful.

Doing more of this kind of work is possible, and it starts with a mindset shift.

Product thinking is a learnable skill

Taste is not an innate gift. It’s a muscle you can train. You don’t have to be a product manager or a designer to learn how to recognize good work, empathize with users, and develop a sense for what works and what doesn’t.

And it’s a skill that’s only going to appreciate over time.

In the vibe coding era, taste wins.

If anyone can spin up CRUD app with AI, what makes your work stand out? What you choose to build and how well you build it becomes the differentiator. That’s not a thought experiment. This is happening now.

The engineers who will thrive now and in the future are the ones who can build with care, precision, and a commitment to clarity and usefulness.

What’s in the book

Here’s what I intend to cover:

1. Building your product sense and intuition

2. Indentifying customer pain points, and solve them

3. Designing features that remove roadblocks and create delight

4. Gaining business fluency and understand how to align your work to business goals

5. Thinking through and making technical/product/business tradeoffs

6. Gaining influence at work without playing office politics

7. Communicating clearly and effectively with non-engineers

8. Taking ownership without overreaching

9. Prioritizing what matters, and letting go of what doesn’t

10. Leveraging product thinking to shape your career

Let’s build something better

If this resonates — If you’re one of the engineers who gives a damn, subscribe. If you do, you’ll get:

• Early access to chapters

• Behind-the-scenes looks at the process

• Subscriber-only invites to give feedback and shape the book

We can’t fix the whole industry. But we can raise the bar, one button, one bug fix at a time.

Want a preview?

Here’s some sample content that’s already available:

How to improve your product intuition (sample chapter)

Trust Over Titles: The Engineer's Guide to Workplace Influence

Questions, comments, concerns?

Leave them in the comment section below, or DM me if it’s private. You can also find me on LinkedIn and Bluesky.

You, Inc.

I am a company of one with a whale client responsible for 100% of my revenue.

Here’s what that mindset looks like in practice:

You work for yourself first

Of course you want to deliver great service and results for your client. But you do it because it boosts your revenue, strengthens your reputation, and builds proof of work like case studies. Selfish motives don’t make for sustainable businesses, and companies that don't take care of their customers or employees won't last.

You have a defined strategy, vision, and definition of success

This is the biggest difference between a 'You, Inc.' and a big corporation: You are not bound by shareholder doctrine. Increasing revenue is great but it can't be the ultimate aim.

You hunt for opportunities instead of waiting to be picked

You actively seek opportunities that align with your strategy. You don't say, "That's not in my job description." You work for yourself, you wrote your job description. You find work that moves you closer your goals. You craft your job in a way that plays to your strengths.

You gotta sell

No way around it: Selling is mandatory.

If you build it they will not come; They are too busy with their own work, wants, problems, and algorithmic feeds. You have to make yourself visible. You need to clearly and persuasively present your ideas. You have to push through that awkward feeling, straighten your shoulders, and toot your own horn. Learning to write & speak pays huge dividends in any knowledge workFor more on this idea I strongly recommend reading the transcript from Richard Hamming’s talk, You and Your Research.

Beyond reframing what I do, I also reframe why I do it. It’s about more than a paycheck.

Building career capital

If we’re all capitalists, then even employment is a game of building capital, not just earning income.

I define career capital as any non-monetary value you add to your balance sheet.

Examples of career capital:

• Skills & expertise - what are you good at, and how well can you deliver?

• Specific knowledge- What secrets and insights have you gained that can't be found in any book?

• Network - How many people know you and what you offer?

• Reputation - Do people view you as someone that is trustworthy, reliable, and can get the job done?

• Proof of work - What evidence can you point to of what you've done?

• Side projects - What have you created that you own?

What ways have you acquired career capital, and how did it pay off?

The most important aspect of career capital is liquidity. Prefer to build capital that you can take with you. The days of working 40 years for a pension and a gold watch are over. I’m not advocating constant job-hopping (though in early tech careers it can be strategic), but all jobs are finite. Plan accordingly.

If you take away one idea, it’s this: expand your investment mindset beyond index funds and retirement accounts. Start thinking about all the other forms of capital you can build.

Collaborating with your client

I worry this attitude may be seen as antagonistic to your employer. In reality its the opposite.

When your customer/employer succeeds, you succeed. You want to be in a position where helping your employer aligns with your goals—and where it’s in their best interest to invest in you because you’re a safe bet with strong ROI.

But like recognizing the finitude of employment, it’s also important to understand the true nature of the relationship. Your employer, from an economic standpoint, is exploiting your labor. Their goal is to extract maximum value from your work. In exchange, you receive steady pay, benefits, and (hopefully) healthcare. For many, this is a fair deal.

Keeping this in mind reminds me that the relationship is symbiotic, transactional, and devoid of loyalty from either side.

I once worked at a company that, after an Amazon policy change, laid off a third of its staff overnight. I watched good colleagues—who’d done nothing wrong—get called into the office, return quietly to pack boxes, and walk out the door. It was a cold reminder: employment is never guaranteed.

Don’t live in fear, but have a Plan B.

You don't get ahead working hard for others. You get ahead working hard for yourself

I’m grateful I spent my early years self-employed. I didn’t earn as much as I could have in a salaried role, but I gained specific knowledge that’s paid bigger dividends. Mainly, it taught me that it was up to me to decide what I wanted, and what work I’d do to get it.

It taught me that in today's environment, I'd always be an entrepreneur, whether I like it or not.

Most decisions are satisficing decisions

I recently had to decide which projects my team would tackle over the next two months. We had several good options, but how could we know which was the right bet? We had informed guesses, but design needed enough runway—so we had to choose quickly.

Pretty much any option would have worked. We could have thrown darts and been okay. We listed our best guesses on impact and feasibility, and picked our next three projects.

Most questions don’t have a correct answer, but all questions have a best answer — subjective and based on context. The best choice is simply the best one you can make in the moment.

Selection sort all the things

I learned this from a beta copy of a book my friend Swizec is working on. Humans are terrible at comparing a lot of options, but we’re good at comparing two at a time. When you’re unsure what to pick or prioritize, make a list and selection sort it.

Watch on YouTube

(God these videos are so satisfying)

Draw blurry pictures

There are two JPEGs compression algorithms: baseline and progressive. Here’s how they render:

Baseline JPEG

Progressive JPEG

Be a progressive JPEG. When you're working on something, start with a minimal but complete version. Better to have all the pieces, regardless of how flawed they are, than an unfinished piece.

There are several benefits to this approach:

1. It informs the work —the middle oftens informs the end, and the end informs the beginning.

2. You’ll likely hit “good enough” sooner than expected.

3. Complete rough drafts are easier to share and get feedback on.

4. It gets you to the revision phase faster. Quality comes from the edits. The trick to delivering high-quality work is a willingness to do more rounds of revisions than most people.

What’s a 10-minute thing you can do right now?

I love this list of high-agency questions from Chana Messinger. The whole thread is gold, but I want to highlight this one in particular:

There’s usually a smaller step you can take to move things forward or a simpler version of what you want to do. When stuck writing an article, I’ll ask myself “can I write a 250-word version of this idea?” That’s enough to get started.

This pairs well with the blurry picture approach. My new favorite way to finish a piece is to set a series of timersThis comes from David Perell’s Write of Passage course, a technique he calls “CrossFit for Writing.” A summary of the technique in this thread.

• Can I make in outline in 10-minutes?

• Can I flesh it out and order it in another 10?

• Can I get together a complete shitty first draft in 30 minutes?

In under an hour, I’ve gone from an idea to something I can work withThis isn’t just for posts on Substack. I use the same approach when writing internal reports and documentation..

Finally, have some fun with it

Thanks to work travel and other internal writing projects, I haven’t posted on here in nearly a month. I felt overwhelmed trying to get back into it, especially with the growing list of articles I feel I “should” finish. Shouldn’t I focus on the most important, biggest ideas first?

I carved a section of this Substack out specifically for informal, off-the-cuff writing. But I felt I “shouldn’t” write one of those, because I had “more important” pieces I should work on instead.

The problem is, that makes this feel like work. I already have work from 9-to-5 and it’s plenty. I start avoiding this text editor entirely. The whole attitude is silly if I think about it. No one is forcing me to write here, or meet any kind of editorial guidelines or deadlines except the ones I set for myself.

Writing is generative, and sometimes fun is what gets you unstuck.

Sometimes the best way to be productive is to spend 20–30 minutes on something frivolous. It reminds me why I enjoy this in the first place. The bigger stuff can wait. they’re easier to write after I gave myself a little time to do a small stakes writing sesh.

Maybe it’s productive procrastination. But — it builds momentum. This resolution isn’t about optimizing productivity or getting more done.

It’s about getting and staying unstuck.

Passion is built, not discovered

Effort and deliberate practice increases your enjoyment and connection with an activity. As Magness and Stulberg point out in their book The Passion Paradox, being connected and intentional doesn’t drain you, it fuels you.

I don’t know why it took me so long to realize this. Besides guitarm I’ve put effort into other hobbies: I’ve run a half marathon. I’ve defeated Malenia. I enjoyed them, despite it being hard. Maybe it’s because after a stressful day, it’s harder to pick these hobbies up. We do only have so much energy in a day, after all.

Life is a marathon, not a sprint. Hell, as I approach my 39th birthday, some days are a marathon. We have to leave something in the tank so we can bring the best of ourselves to what matters. It’s an investment, and it’s worth it.

That said, as soon as I finish this draft manuscript of System is as System DoesI’m taking a break and not looking at the damn thing for a week.

I’m not a boss, I’m a talent wrangler.

On film sets, talent wranglers manage schedules, handle logistics, and keep actors focused while coordinating between production crews and studios. Their job is to get the best performance out of my actors given the role they are playing in the movie they’re making.

Similarly, my job is to get engineers to perform at their best. I manage schedules, handle projects, maximize reports’ focus time, while coordinating between product, design, and stakeholders.

What does that look like day-to-day?

Many people misunderstand managers' roles, assuming we don't contribute much. When asked, managers throwing out vagaries like “unblock” and “liason” doesn’t exactly help.

To help answer this, I started keeping an inventory of the tasks I was doing from day-to-day:

• Project management: - Creating tickets and project plans, and assigning tasks. Running kickoffs, retros, and syncs.

• Switchboarding: - communicating across multiple slack channels and DMs, maintaining and index of resources so I can the right information to the right person at the right time.

• Hiring: - writing job descriptions, conducting interviews, and coordinating with recruiting and finance to get resources.

• 1-on-1s: With my team, with my manager, and EPDEngineering, Product, and Design peers, with my manager.

• Performance management: Developing and enacting growth plans. identifying opportunities that align with team members’ goals. Asking other people “What would you say they do around here?”

• Writing: PRDsProduct requirement document, SOPsStandard operating procedure, agenda, TPS reportsOffice Space reference, miniature manager manifestos. Especially working remote, written communication is a huge part of the job.

To summarize, my job is to do all the context-switching so that engineers don’t have to.

But don’t you miss writing code?

This is the second most frequent question. “Building is so fun! Why would you trade that for [shudders] meetings?”

There is still some “IC work” involved, at least for now. When I do I focus on work that unblocks and empowers my team: Reviewing tech specs and pull requests, taking care of the occasional urgent bug so my engineers aren’t interrupted.

Also, I get to do a more abstract, more fascinating kind of engineering. I am still working on a system. The system is made up of values, processes, goals, and plans. We are constantly designing, refining, and refactoring it. Instead of writing code for computers to execute, I write ideas for people to implement.

DO: Use AI for research

ChatGPT Deep research is the new Wikipedia page. A starting point, not an answer. They are tapas menus of resources to pick and choose from. A great first stop when you delve into a new topic.

DON’T: Use AI for summarization

Summarizing isn’t just condensing information—it’s deciding what matters, how to structure it, and how to reframe it. Summarization is how you build retention and understanding. It’s a creative, intentional act. Delegating summarization is like sending an android to your CrossFit class.

DO: Use AI as reference

Writers have always relied on tools—there’s no shame in using them to improve your work. When I’m stuck on a word choice, I’ll ask ChatGPT or Claude to give me 5 options to fill in the blank. Sometimes it’s faster than reaching for the dead tree tool a whole 15 feet away.

Don’t: Let AI strip your writing of personality

Don’t shove text through the AI mill and uncrtically publish what comes out the other side. Instead, use AI for suggestions. Pick the ones that work best or use them as inspiration to go in another direction. AI gives you options, you provide perspective and taste.

Do: use AI as a line editor

AI won’t make creative word choices, but it can suggest clearer alternatives, like replacing “talk about things” with “communicate.” Here’s a prompt I’ve been experimenting with to do this:

Act as an experienced writer with a focus on improving the clarity and readability of text. You are responsible for reviewing a piece of text. Break down the sentences into simpler forms without losing the original meaning or nuance. Implement appropriate punctuation, streamline the language, and remove any unnecessary jargon or filler words. Ensure that the content adheres to a consistent style guide and retains its original purpose while becoming easier to read and comprehend.

Go section by section, and give me the original version, the revised version, and a list of changes made

Don’t: Rely on AI as proofreader

AI cannot replace human feedback. It can fix a sentence, but it can’t tell you if it’ll resonate with someone. Writing is still for readers, and we need readers to help us figure out what’s interesting and what’s dull. What’s mind blowing and what’s confusing.

AI is an assistant, not a replacement

AI cannot replicate personality, perspective or taste. It cannot build human connection or express a deeply held belief. It can only help humans do so. It can replace my thesaurus, but it can’t replace my mind or my soul.

To wit, if your paycheck is contingent on pumping out thoughtless, soulless content, then yeah, I’d be concerned.

Battling the Resistance

In his book 'The War of Art,' Steven Pressfield identified this phenomenon as 'the Resistance.' The Resistance is the antithesis of the Muse. Instead of inspiring you to create, Resistance tries to stop you.

Creativity requires doing something others won’t do, to an audience that might not materialize, without a guaranteed reward. It requires vulnerability. The feeling of resistance is normal and unavoidable.

Understanding that resistance is normal and expected should help prevent it from stopping you. Being creative is supposed to be uncomfortable. It’s like going to the gym — discomfort signals growth.

What’s the point of publishing online? Is it worth the time?

I can promise you it is.

You have value worth sharing. Helping even one person justifies the effort. If you frequently get the same questions, Publishing an answer saves you time and helps others more efficiently.

Writing also crystallizes your thinking. While our minds are fuzzy, unreliable webs of thought, writing is concrete and linear. The page stares back at us. It begs for examination. And knowing that other people will see it now encourages us to raise the bar on the effort and quality of our thinking.

Publishing can spark meaningful conversations. I’ve reconnected with old friends (Hi Cory and Jeremy!) through writing. I didn’t anticipate that, but I’m grateful for it. Sharing your ideas has a way of attracting like-minded people. You’ll also be a more engaging conversationalist since you’ve refined your thinking and opinions more than most.

Writing online can create opportunities. The right person reading one of your pieces at the right time can open doors. Based on my articles, I’ve received job offers, invitations to give talks, and opportunities to lead initiatives at work. The internet is an infinite leverage machine.

Finally, humans are built to create, not just consume. I want to see more people putting their ideas out into the world. I’ve read articles and essays that have permanently altered the way I think, and changed my career path for the better. What if you could make that happen for someone else?

Okay, I see the value in publishing. Do I have to go build a whole website now?

This is a common sticking point, especially for engineers. They want a personal website to pull double duty as a platform to share work, and a playground to mess around with shiny new technologies. Do not turn your personal blog into an engineering project at the start. Single responsibility principle applies here.

If you can’t spin up a new website in four hours or less, you’re doing it wrong. Making a website is easier than it’s ever been. Use SquareSpace or WordPress or Ghost. It doesn’t even have to be a website! You could use newsletter-based publishing tools like Substack or Beehiiv.

Okay, I have a site, but I don’t want to be a “blogger”

You don't need to build an audience, commit to a schedule, or maintain a content calendar. Forget about creating a "personal brand," crafting a "positioning statement," or developing a "content strategy." Resistance is trying to make the problem sound bigger than it is.

What I am advocating for is an entirely different game. Tom Critchlow calls this ‘Small-b blogging.’ You aren’t writing for a massive audience. You are writing for your network.

Don’t write just to hit some frequency some hustle blogger said you should, or to maximize pageviews. Instead, strive for writing that has specific appeal, at a comfortable pace, aiming for meaningful engagement over empty metrics.

Don’t borrow trouble from future articles no one is forcing you to write. Focus on what’s interesting now. Who can you help, and what can you publish today?

I don’t know enough

You have more expertise than you realize. Years of experience becomes so familiar we take it for granted — like water to a fish. Ideas that are obvious to you could be a revelation for someone else.

Here’s a secret: experts don’t write because they have expertise. They have expertise because they write.

Writing is a method for building expertise more than sharing it. The root of the word "essay" means "to attempt." You ask yourself a question and attempt to answer it, going on an intellectual journey and bringing others with you.

There’s an episode of the Simpsons(Spelling as Fast as I can) where Marge is trying to figure out how they are going to pay to send Lisa to college. They have this exchange:

There’s real value in being one lesson ahead of the kid. Your recent time in the trenches gives you an accurate memory and shared context with the reader. The fresh perspective of someone who just learned something enables you to communicate in a more relatable, high-fidelity way.

To discover what you know, you have to get it out of your head. Jot down a rough outline of supporting points for your idea. Try doing a 10-minute free write on the topic. You can try to fill it in with other notes, ideas, and links. You might surprise yourself with how much you come up with.

From there, targeted research can fill any remaining gaps.

An idea I value is intellectual activism: The art of taking existing information and making it more accessible, understandable, useful, or enjoyable to others.

Finding information in books, papers or online videos, or threads and distilling and sharing it in a way that’s accessible to others is a public service. Curating and combining resources generates new value from existing material. You can draw from multi-disciplinary knowledge. Warren Buffet says he learned about how markets evolve by reading The Origin of the Species.

This is why I take notes compulsively and collect information and links like Pokemon: When I sit down to write I don’t face a blank page. Instead, I can draw from my bank of ideas and evidence.

I have nothing original or interesting to say

Isn’t that cheating though? How is building off of others' work not plagiarism?

The concept of “originality” in writing is a myth. Can you name a writer that is truly “original”? Everything is a remix — we all build on existing ideas. The image of an author pulling inspiration from the ether is fantasy. It's all old hats through new lenses.

No one is original, but everyone is unique. Your personal perspective matters and is worth sharing. Anyone can share facts or links. Combining them with your experiences, skills, context, and stories creates something worthwhile.

Uniqueness is combinatronic. For every experience, memory, skill, and story you have, there are intersections between them all. These give you even more unique places to draw inspiration.

Your network is also unique to you. If you share something with someone, they will see something that otherwise wouldn’t have. Don’t feel bad because it isn’t original “enough.”

Once you have an outline, you can add color to it by adding bits only you can: your stories, experiences, memories, observations, and perspectives. Consider how these elements intersect with each other and with your topic.

This piece was inspired by other books and articles I’ve linked to. They all have one thing in common: All these authors have had much more writing success than me. I had to get over Resistance telling me I didn’t “deserve” to write this. I’m betting there is some value in someone saying, “Look, I don’t have impressive subscriber numbers to show you. My readership is tiny. I still think it’s worth showing up and putting my ideas out there.” Maybe you will too.

You can also remix your own work. Every piece does not need to be 100% brand new. Previous notes, comments, conversations, or documents might have material that can be reused. I call this stuff “grist” material that is ready to be refined into something useful.

By using the existing grist, you can craft version 2s and version 10s of your ideas. These are bound to be better than the original. Venkatesh Rao calls this The Calculus of Grit. If I had written it first, I probably would have called it “The Calculus of Grist.”

The idea that you aren’t smart enough or original enough is also a myth. It can be safely ignored. Take the path of least resistance. There is an abundance of work out there from yourself and others, ready to be refined, referenced, and remixed.

The twin anxieties of readership

People can have opposite reactions to the same stimulus. Some people lose their appetite when they get stressed. Others reach straight for the fries and Girl Scout cookies.

As you approach hitting “publish,” Resistance gets stronger. His final move manifests in one of two opposing fears: Either you are afraid that no one will read what you write, or are you afraid they will.

I’m afraid no one will read what I write

Even if no one reads your piece, there is still inherent value in writing and publishing. You refined ideas and have more material for next time. You have an asset that may pay off later. You have one more rep hitting publish. Maybe you needed to write this piece so it could tell you what you should write next.

Everybody can benefit from the result. You get to benefit from the process.

If you want readers, be proactive. Put your link out on all your socials. Sure, that’s table stakes. But also, if you wrote a piece that you think could help someone you know, send it to them directly.

Here’s an offer: If you’re scared you can use me to practice. Send me your published piece or even a draft in Google Docs. I promise I’ll read it and share some feedback. You are guaranteed to have at least one reader.

I’m afraid someone will read what I write

What if the end result isn’t “good enough?” What if we’re misunderstood or misrepresented? This is a classic move of the resistance. It’ll never turn out exactly how you pictured it. Vision is ahead of execution, as it should be. Just remember that so long as you try, whatever you were able to put out was, in that moment, your best work. That’s all anyone can ask of you.

You can’t be perfect but you shouldn’t be sloppy. It takes practice to find the correct amount of effort to put into a piece before hitting publish. In my experience, the quality of a piece is a function of the number of revisions, not some spark of genius.

What about negative feedback? If you ever have an article that gets any traction, you will get some haters. This is a good thing. It means someone thinks your piece is worth engaging with. Some are trolls that can be ignored. Others will give you the precious gift of feedback.

This is a valuable part of the process. You can only refine your ideas and perspective so much internally. The real magic is in when you use them to interact with others. Feedback counts as grist.

Internet writing remains malleable—you can always edit or delete content. The internet has a goldfish memory, and it remembers successes more than failures.

Anything you publish is a UI for the reader who wants to be entertained or informed. They want the piece to be good. They are rooting for you. Everyone is on the same side; The relationship between reader and writer is ultimately positive.

Godspeed

Don’t be afraid. Countless others have published blog posts and lived to tell the tale. In a world overrun by vertical videos and AI slop, online writing is one of the best asymmetric bets opportunities for knowledge workers. You can create a lasting, high leverage asset in a few hours, for free. By writing and publishing, you refine your thinking, create a shareable asset you own, and expand your luck surface area. How many other activities offer this much upside with such minimal investment?

All you have to do is get over capital-R Resistance and do some small-b blogging. I’m excited to see what you come up with!

Why people gamble more when they can’t “afford” it

Walters started from meager beginnings and spent his early years in a cycle of hustle and self-destruction. Have the biggest quarter of any car salesmen in the region, then blow it all on booze and playing pool.

Keeping money in the bank when you aren’t bringing much in is tough. You could spend March, April, and May scraping together a few extra bucks, only for your in-window AC unit to die in June. Your savings are gone; you’re sweating from the sun and your next car payment. And it’s not just about the money. It’s about the habits.

It’s rational for people in that situation to put a few bucks towards lottery tickets, not just for daydream equity, but because a 1-in-11,688,053.52 chance of escaping poverty is better than zero.

There’s a strong connection between growing up in poverty and having a gambler’s spirit. “gamb00l,” as we called it back in the online poker boom of the early 00s. You see people with steady incomes getting nowhere. When you can’t afford to fund a ROTH IRA and your employer does not provide a 401k, saving is not seen as a path to wealth.

The lucky few find opportunities to channel this gamb00l into variant-income careers like sales, finance, and entrepreneurship. Maybe they get started waiting tables. The difference between success and failure is whether or not you can break old habits and build new ones.

Betting like a businessman

When Billy watches one of their friends die in his 40s, it’s a wake-up call. He stops smoking, drinking, and going to casinos(though he continues to bet on sports). He starts saving his money.

Eventually, he partners with a group of quants called ‘The Computer Group’ and manages to build a sustainable, winning sports betting operation. Walters claims to bring in $50 to $60 million in winnings in a good year.

When he starts “wagering as a business,” he uses mathematical modeling to create lines and bet the deltas between his lines and the sportsbooks. Model shows the Bengals as a +4.5 favorite and the sportsbook has them at +2? Put some money down and pray Joe Burrow pulls through for you.

Funnily enough, this book made a lightbulb go off with me about investing. Value investors do this with stock pricing—betting on your models vs. the market.

Investing lessons from a gambler

1: Bankroll management — Have a bankroll(a pile of money dedicated solely to your betting). You have to be comfortable losing 100% of this money. Don’t put more than 3% on a single bet. And when you’re ahead, take some money off the table.

2: Every percentage point matters — The house edge on most casino games is 3-5%, but that’s enough for casinos to rake in $8.3 billion last year. The slimmest edges can make the difference between winning and losing.

I’m reminded of a quote from Roger Federer’s commencement address at Dartmouth:

3: Find the best price — Pay attention to fees and taxes. Use multiple accounts, and when you’re ready to make a play, ensure you’re paying as little as possible.

4: Different horses for different courses — There is no universal strategy. Understand the context you’re in, and adjust accordingly.

The Gambler’s journey

I want to say Billy had an unconventional path out of poverty, but that feels weird to say because there isn’t a conventional one. Some standard advice still applies: If you’re not born lucky, you must work hard, have discipline, and still get lucky at some point.

I’m reminded of the time in college I spent two years making a living playing online poker: People imagine gambler as these rogue mavericks who put it all on the line. In reality, the successful ones are stoic, risk-averse, nerdy number crunchers.

And they had a couple of lucky breaks early on, which seeded their bankroll and their self-confidence.

1 - James Sinegal, Founder of Costco

Sinegal runs one of the most successful retail operations in the company. Does so selling products nearly at cost. Pushes suppliers to make packaging with less waste. Has a company minimum wage of $19.50. One threatened to kill a man over hot dog pricing.

2- Mike Illitch, founder of Little Caesars Pizza

He ran a local youth hockey league. Founded the Little Ceasar's Love Kitchen, a food-truck-based charity that provides free hot n' fresh pizza to the homeless and people in disaster areas. Paid Rosa Park's rent for a decade and didn't tell anyone. He knows he could charge you more than $5 for a pizza, but he chooses not to ensure low-income families always have access to a hot meal.

3 - “Trader” Joe Coulombe

Paid will above market wages. Invented almond butter. Includes a treasure hunt game in every store to keep your kids entertained. Makes it so you can grocery shop and still not have to cook.

The common thread

Besides lacking the dead eyes you see in many other CEOs, what do their business have in common?

They all pay their employees above-average wages. They all have a keystone value item. Because of these three men I can have a dinner of a hot dog, coke, pizza, and wine for $8.50. Hockey stick growth for my cholesterol for under ten bucks.

But what’s most interesting is that each of them competed on price without sacrificing quality. Costco does it on volume and a no-frills shopping experience. Little Caesar’s does it by keeping the menu lean. Joe achieves this by sourcing non-traditional products and packaging them under his brand.

Value for your customers. Generosity for your workers. Focusing on the essential.

That’s the kind of place I’d want to run.

The not-so-subtle art of giving a f*ck

I despise the “vulgar self-help wave,” but I couldn’t help myself

Earlier this year, I committed to putting more effort into increasing both the quantity and quality of my writing. There were several motivating factors:

I realized you should put effort into your passions.

I read Angela Duckworth’s Grit. My main takeaway: Interests are built, not found.

Interests become more fulfilling when you invest in them. This was counterintuitive to me. I always figured hobbies should be casual. I assumed they would stop being fun when they started getting hard. It turns out it’s the opposite. I’ve always said I enjoyed writing but never took it seriously. What happens when I do? Let’s find out!

I decided to write a book

For the better part of a year, I’ve had an idea for a book designed to help engineers increase their product thinking skills so they can deliver better outcomes and have more agency in their work. I hemmed and hawed on whether it was worth it to pursue this idea.

Then, when flying cross country ATL → SFO, I read Write Useful Books. With a new framework in hand, I decided to give it a shot.

Writing a book isn’t just writing a book, it’s writing the promotional copy, the drafts, the pitches, the supplementary marketing material. If I’m going to pull this off, I have to step up my game.

I became an engineering manager

At the start of 2025, I transitioned from software engineer to engineering manager. I view a large part of engineering management as content strategy — Agendas. Specs. Documentation. Slack Messages. Curating information from around the company and distilling it into a digestible format for my team.

Writing is an essential skill for effective management. When you work for a remote company, doubly so.

Examples of generative writing I’ve witnessed

Content blossoming into more content blossoming into even more

I shared a draft table of contents for the book idea with some friends (Great idea from Write Useful Books). I had a tertiary section about “improving your product intuition.” It was the one everyone was most interested in, so it became a sample chapter. Since publishing that, there are a couple of other sections that people found interesting. I can blow those out into entire chapters or larger sectionsHow do engineers balance craftsmanship with outcomes? How can they ask better questions when collaborating cross-functionally?.

Essay ideas while writing this very piece

Part of my writing practice is posting a short, informal post about whatever is on my mind weekly (At the Edges). When working on this update, I had two other ideas, then realized they probably have enough meat on the bone to be more fully fledged essays.What are the practical benefits of magical thinking?How the “imagination premium” explains the seemingly irrational market behavior of meme stocks

Writing creates opportunities

I can’t share too much publicly, but since sharing some sample work from the book, I’ve had some interesting conversations with people I wouldn’t have expected and some exciting opportunities in the “product thinking for engineers” space on the horizon. Those conversations pointed me toward the next part of the book project I should focus on.In broad strokes, more on cross-functional collaboration: Articulating your value, executive translation, and how to ask better questions.

The combination of writing and sharing is powerful. I’m excited to see where this next part of the journey takes me.

I am also terrified. People have bought in and started supporting this “write a book” idea. Now I’m gonna have to sit down and actually finish this damn thing.

Influence is earned, not given

When studying for my new engineering management positionFound in HBR's 10 Must Reads for New Managers, a resource that was a lot more useful than the listicle title would lead you to believe., I stumbled across this quote:

New managers think that just because they have a fancy new title, people are going to listen to them. As a recent engineer turned manager, I can assure you that’s not always true. There are ICs in the company that have more clout than me or most managers. It bears repeating, a better title does not by default give you more influence.

Trust starts with credibility. You can’t bullshit your way into credibility. You have to earn it by displaying competence and reliability. How?

You deliver. The right thing. When you said you would. Repeatedly.

Displaying credibility in your day-to-day work

There is unspoken power in being the person who delivers the final product to the user. You likely have more say in your day-to-day to make an impact than you realize. Here are some ways you can have more impact and start to build credibility at work:

1. Prioritize high-impact work over low-hanging fruit

Given a list of tickets, I might ask myself: “Which of these will have the biggest impact on the user?” “Are there any quick wins or low-hanging fruit I can tackle?” Sometimes, I do an easy little ticket in the morning as a treatIt is an effective way to fight back against burnout, especially if you have been stuck on a slow-moving slog with little progress to show for it.. As long as everything else is moving along, no one has ever complained about people making quality-of-life improvements of their own volition.

2. Prioritize quality

You can decide how much time you want to dedicate to quality. For example, I once built a new spending summary component for a debit card page. The designs didn’t call for animations, but I noticed the transitions felt clunky without them, so I took extra time to add them. The UI was higher quality because I decided it would be.

Everyone makes tradeoffs about time vs. qualityIt’s more of haste vs. quality. The “fast, cheap, good” triangle has been debunked. Shipping faster leads to higher quality over time. But that’s a tangent for another day.. Most people default to shipping faster. You can make yourself an outlier by moving in the other direction, even just a little bit. You must prefer visible product quality over invisible code quality, and you can’t go too far. No one wants to work with a slowpoke.

3. Write

If you take one action after reading this article, it should be to write and share a document at work.

Writing standards docs. By writing a resource about accessibility guidelines and common patterns, I helped indirectly increase how accessible our application was, not just in my department but company-wide. So few engineers are willing to take the time to write quality documentation, policy, and standards. Being the one to do it is a superpower.

Building trust & strengthening relationships

Competence is essential, but it isn’t the whole game. Many developers are good at writing code but only good at writing code. They don’t understand why they are limited in their career. Software is a team sportAnd the bigger the company you work for, the more essential these skills become. You have to build trust with others.

Building trust takes time—one person at a time, one conversation after another. The only way to build a cathedral is brick by brick.

Be honest, even in shortcomings, especially in your shortcomings. Managers hate surprises. If you’re going to miss a deadline, let them know upfront. The sooner, the better.

Getting along with people isn’t required, but it sure helps. Pedro Pascal sums up the attitude nicely:

Take a human interest in people. Know the name of every dog, cat, and child your coworkers are responsible for.

Be genuinely likable. I’m pretty mid at coding. Most of my career success comes from being charismatic and funny. If people don’t like working with you, you’ll be included in fewer conversations. Thus, fewer relationships, therefore less power. Few of us are truly “changing the world” and could afford to be more playful at work.

Wielding influence

You’ll have opportunities to use your influence as you become more trusted. Start small. 1-on-1 conversations over big pitches.

Favor asking good questions over offering specific advice. As Micheal Bungay Stringer says in The Coaching Habit: Tell less and ask more. Your advice is not as good as you think it is. Questions are more valuable than many realize.

Pick your battles. You can’t win everything.

Share your influence generously. You can help others gain influence. You can give a voice to the voiceless. You can shine a light on people that deserve it.

And remember to use this influence for good. It gives you a unique opportunity to help your company, customers, and coworkers.

And y’know, make your product better and get a raise and a promotion. You don’t have to do all this for free ;)

Consulting models

While driving to the gym, I was listening to Peter Block's book Flawless Consulting: A Guide to Getting Your Expertise Used. In it, he talks about three models of consulting:

1. Consultant as line worker. They want you to do the work.

2. Consultant as collaborator. They want you to work together on figuring out what to do.

3. Consultant as expert. They want you to tell them what to do.

Consultant failure modes

I realized when an engagement didn't go so well, it was one of two failure modes:

1. I thought I was the expert; they thought I was a line worker. Could you imagine going to Subway, ordering a meatball sub, and the sandwich artist looking at you and saying, "What's the real problem here?" There's a mismatch of expectations, and that conversation isn't going to go well. I realized this is what happened with a lot of my clients. I wanted to be an expert. I wanted to try to solve the big thorny problems, and they wanted a Coder. I ended up writing the code, but we had some awkward meetings, and I wasn't thrilled about it.

2. I was a line worker tasked with an ineffective plan. Who do you think they're going to blame? The internal stakeholder or the outside contractor? Sometimes, it even felt like I was hired strictly as a fall guy to work on a project that they didn't want to do, but deep down, they knew it wouldn’t pan out.

So why now?

So why am I listening to this book now? I haven't done contracting or consulting since 2016, when one of my clients hired me on for a full-time position(I guess that engagement went pretty well.)

The reason is that coaching and consulting aren't titles. They're skills. As I'm getting into engineering management. I see how these types of engagements show up internally, informally, all the time.

When the stakeholders want a report on potential courses of action and the tradeoffs between each, I’m consulting. When I'm helping my reports grow their engineering skills, I'm coaching.

I've realized that management isn't a single skill; It’s a collection of multiple skills. And right now, these are the skills I want to improve.

Building single function apps with AI

Check out this detailed workflow an engineering manager shared. The tl,dr is:

1. Use ChatGPTIt doesn’t have to be ChatGPT. Use whatever service you like best. Recently, I’ve been impressed, curious, and mildly terrified about DeepSeek. to help you write a small product spec

2. Use Vite as a framework, put the spec file in a repo, and use Cursor to bootstrap the product

3. Use tinier specs to iterate on smaller facets of the project.

4. Final mile work: manually make minor updates and fixes and add polish.

5. Use the composer to write out GitHub Actions.

6. Ship it!

Using spec files with Cursor is a neat trick. You now have a tool that can read your spec, write your code, and even write a changelog about its process if you ask it to.

It is something I will be trying in the future, no doubt. Not sure what yet, maybe I’ll ask an AI about that to.

Prompts as Scripts

Besides writing scripts, I’ve started thinking of prompts as scripts. Writing a prompt is not a few sentences you throw together once. It can be something you put effort into so that you can use it again and again. I’m moving my prompts into a GitHub repo so I can document them and track changes. I am taking prompt engineering seriously as a disciplineClaude has official prompt engineering guidance, a solid place to start: Prompt engineering overview..

A simple prompt framework

• Here’s a rubric I’ve been using when writing prompts. A good prompt includes:

• An action to take

• Steps to perform the action

• A persona to emulate

• Examples of inputs and/or outputs

• Context about the action and situation

• Constraints and what not to do

• A template or desired format for the output

It’s not much, but it’s a start. If you have no idea where to begin, I hope that helps.

Information Architecture

While working on refactoring some internal documentation, I gave How to Make Sense of Any Mess another read. You can read the book online for free at that URL. I wish I could make everyone read this book.

Content isn’t just about the content we create. How we index it, order it, and organize it matters. The organization gives information context and meaning. It tells people what’s important and what isn’t.

Information architecture requires human intent to take content & data and arrange it in a way that makes it understandable. It involves taste and opinion. You cannot offload information architecture to machines.

Search engines treat all content equally. AI is an attempt to outsource understanding, but it's prone to omissions and hallucinations.

So, what am I saying with the new organization of my writing? The purpose of the book project is to encourage developers to take more initiative and ownership when it comes to the work they share with the world.

The theme of this site has trendedI’m realizing more and more themes and “personal brands” are forged not discovered. I didn’t start with these themes in mind, but looking back at following my curiosities, that’s where it’s been. towards encouraging people to take more initiative and ownership in their careers, their finances, and living under a kleptocracy.

My purpose with writing has been to help others overcome resistance. To get out of their own way. To have more agency in doing work that can be proud of in service of getting what they want and helping who they love.

At the end of the day, it’s all one goal; it’s all important to me, so now it’s all one site.

What is product thinking?

“Product thinking”’s definition is nebulous. Putting it into practice is inscrutable, yet it’s a fundamental building block of being a higher-level software developer.

“product thinking” is the art and science of balancing business strategy, customer experience, and engineering robustness. It’s about thinking about software from the perspective of how it behaves instead of how it works.

Another way of thinking about it is balancing the user's needs with the business's capabilities.

Feature-driven vs. product-driven development

The opposite of product-driven development is feature-driven development. This might sound weird at first. What is a product if not a collection of features? But there is a world of difference focusing on the collective rather than individual features. One sees the forest; one can’t see from the trees.

Feature-driven developers are:

1. Tech-centric

2. Solution-focused

3. Narrow-minded

4. Disconnected from stakeholders

5. Siloed

6. Focused on inputs

7. Robotic

Product-driven developers are:

1. User-centric

2. Problem-focused

3. Holistic

4. Aligned with business goals

5. Cross-functional

6. Focused on outputs

7. Empathetic

Feature-driven developers close tickets, fix bugs, and ship features. Product-centric developers solve problems, deliver value, and help people.

The only way we’ll improve software is to move more software engineers from the left side of the graph to the right. The reason I suspect engineers struggle with this is two-fold:

1. Product thinking is more abstract. The lack of ambiguity is the flame that draws a lot of engineers into the craft.

2. It’s a tacit skill - there is no leetcode for product thinking. It’s more of a way of thinking about your work than something you can practice deliberately.

Good product thinking requires developing your product intuition.

But can intuition be developed? People talk about trusting their gut, but don’t talk about how to train said gut to make better decisions. It turns out you can, and one psychologist figured out how:

How intuition works

Delving further into tacit skills, we can use Gary Klien’s Recognition-primed decision-making model, which describes how people make decisions in complex situations, to further examine what’s going on in a product thinker’s mind when building:

1. Developing expectancies - Using hindsight to figure out how the codebase got to this state and forecasting where it might go in the future.

2. Spotting relevant cues - Determining which information you should pay attention to and which you can ignore.

3. Prioritizing & Triage - Deciding what work needs to be done now, and what you can set aside.

4. Apply or create scripts - The mind seeks established patterns to follow in familiar situations. For novel scenarios, it develops new approaches.

Here’s a more in-depth look at the modelI find Klein’s work fascinating; I may do a deeper dive into his work in a future post.:

Like a language model, you can train your intuition for better results. You can use three tools: heuristics, patterns, and application.

1 - Heuristics

A heuristic is a practical rule of thumb or mental shortcut that helps you make decisions or solve problems quickly. They are more guidelines than a rigorous formula. They are generally but not always accurate. Some examples: “Keep code DRY: don’t repeat yourself,” “Premature optimization is the root of all evil,” and “If you have to explain a joke, it’s not funny.”

The gold standard: Nielsen’s Heuristics for User Interface Design

If you read only one other article on Heuristics, it should be 10 Usability Heuristics for User Interface Design from the Neilsen Norman Group, a research-based user experience consultancy. Putting these into practice will put you ahead of 90% of other engineers. A summary:

1. Status visibility: The product should always keep users informed about what is going on

2. Familiarity: The design should speak the users' language and follow real-world conventions.

3. Emergency exits: Users can quickly correct mistakes or backtrack on choices.

4. Consistency: Words, actions, and other affordances should have consistent meaning

5. Error prevention: Prevent errors where you can and provide clear feedback when you can’t.

6. Recognition over recall: The machine is the user’s memory, not the other way around

7. Simple & powerful: products should be plainly simple enough for novices and subtly powerful for experts

8. Focus: Interfaces should contain the information needed and nothing more

9. Error recovery: Error messages should provide a solution

10. Document: Build a product that doesn’t require documentation, then document it anyway

Other useful heuristics

There’s a handful of other adages out there that can serve as heuristics. Here is a collection of the ones I’ve found most helpful:

1. Jakob’s Law - People spend most of their time using digital products other than yours.

2. Law of Prägnanz - people will interpret groups of complex and ambiguous shapes in the simplest form possible.

3. Miller’s Law - People hold an average of seven things in their working memory they can accurately identify.

4. Aesthetic-Usability Effect - People are more tolerant of minor usability problems when an interface has an aesthetically pleasing design.

5. Fitt’s Law - The time it takes to click a target based on the target's size, distance, and position.

6. The Von Restorff Effect - One visually unique object will be remembered among a group of visually similar objects.

7. Teslers's Law - Demonstrates that a system's complexity cannot be simplified beyond its condition to function. Simple interfaces require complex code.

8. Peak-End Rule - People judge experiences mainly on how they end.

9. The Doherty Threshold - People's attention and productivity increase when the interaction response is within 400 milliseconds.

10. Sturgeon’s Law - 90% of everything is crapSee also Dan Luu’s 95%-ile isn’t that good

When building expertise and intuition, first, you learn the rules. Then, you learn which rule to apply and when. Then, you learn when there are exceptions to the rules. Then, you know how to break them.

2 - Patterns

While heuristics give you rules, patterns give you tactics. The more patterns you’re familiar with, the easier it is to devise a plan of action in different contexts. Patterns will even teach you tactics when you don’t realize it.

Studies have shown that we can learn to discriminate different objects and automatically form categorizations from exposure to instances of things. The more features you build and the more you see, the more likely you’ll “just know” a solution to a problem when one comes up in a meeting, even if you don’t know how you came to that conclusion.

Look for similar problems

Whatever problem you’re working on, chances are you aren’t the first person to face it. How have other people solved similar issues in the past? For example, you must build a form to capture a user’s address. Plenty of people have done this before, and if you look, you can find common patternsThe US Government has a published guide for address form best practices.

• Using an autocomplete powered by Google Maps to fill in the address for you

• Calling them ‘postal code’ instead of ‘zip code’ if you are supporting non-US customers

• Using input masks or placeholders to show people the format you expect for postal codes and, if you’re collecting them, phone numbers.

You may also check yourself to ensure you don’t believe one of the many falsehoods programmers believe about addresses.

I’m not saying implement these patterns verbatim, though you might. What I am suggesting is looking for similar solutions for inspiration. As a bonus, these can be easier to pitch to stakeholders. No one gets fired for copying Apple.

Search your memory banks for previous patterns

You might remember seeing a product solution either as an implementer or a consumer. For example, when I got a job at a financial services company, I had never worked in that industry before, but I paid a credit card online. I can relate to the customer’s expectations, needs, and frustrations.

This is what starts to happen subconsciously more and more as you practice. Let’s look at Klien’s decision-making model again:

1. When you look at a problem, you form expectations of the effect of different solutions based on previous patterns.

2. Also, based on previous patterns, you get a sense of what’s essential and what isn’t.

3. You understand what a reasonable outcome is, which helps you pick your next course of action.

4. You may recognize previous courses of action, which helps you triage and prioritize.

With existing work, you only get to see the outcome. Looking at your previous work, you see both the outcome and the process. Similarly, we can also study others' methods.

Learn patterns from case studies and observing others

One good thing about engineers is that they love to blog. Another way you can improve your expertise is by reading stories of how other people solved problems. Watching videos of people's work is a less explored but powerful way to improve your skills.

I once heard a story about someone who was learning to draw. They read books; they drew dozens of pictures to practice. Then they watched another artist on YouTube, and within minutes, they had a breakthrough:

They weren’t holding the pencil correctly.

None of the books taught him how to hold a pencil. It’s an oft-ignored detail of the drawing process. Watching others in action can teach you some of the ‘hold to hold the pencil’ type of tiny details that can make a big difference in your problem-solving. Some reading I would recommend for some case studies on solving technical problems:

• Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs

• The Mythical Man-Month: Essays on Software Engineering

• Ryan Singer shares a lot about his process on his blog Felt Presence

Pattern identification as background process

You don’t have to look for a particular pattern to notice a potentially useful one. Try to pay more attention to times when a product or a piece of code makes you say, “Wow! That’s quality.” Ask yourself what you like about it. What makes it quality?

As prolific blogger and poster Visakan Veerasamy likes to say, focus on what you want to see more of. The more you pay attention to quality software, the more quality software you’ll build.

3 - Practice

It’s been theory so far: how intuition works and how you can supplement it with heuristics and train it with patterns. But none of this is helpful if you can’t put it into practice. Here are some actionable next steps:

Look through a product-focused lens

If you’re coding every day, you are faced with small decisions about product quality. Everything we create is a product, even if it isn’t customer-facing. Some other ‘products’ of your work

• Your code is a product for other engineers on your team. The UX of code is experienced when other developers have to modify or fix it.

• Bug tickets, pull requests, and code reviews are also products for your teammates.

• Status reports, tech specs, and other documentation about your work are products for managers and stakeholders.

Books are products. Podcasts are products. A cookout you throw for your friends is a product.

Try to shift your perspective from “how it works” to “what it achieves.” Think about how others feel and react when interacting with your work.

Ask yourself questions to hack your brain

When Klein developed the Recognition-primed decision-making model, he realized he could get people to surface some of their intuition into cognitive thought by interviewing them while they were working.

He would ask subjects questions like:

1. What cues did you notice first?

2. In this particular situation, what did you expect to happen next?

3. What are your priorities right now?

4. What courses of action immediately sprang to mind?

Try this exercise on yourself. It can help you examine and better understand your problem-solving process.

Pair with designers & stakeholders

Ask your designers or product owners if there are any meetings where you can be a fly on the wall. You’ll pick up tacit knowledge by watching other people think though and discuss problems. Another opportunity to see how others “hold the pencil.”

Ask questions and provide constructive ideas. Contribute, but don’t interfere. This will give you feedback on your product thinking.

Make microdesign decisions

Rarely does a design or tech spec come through with every edge case and permutation covered. Filling in these gaps is up to the engineer who is implementing them. I call these microdesign decisions.

One model you can use to help identify these is the rules UI Stack. The UI Stack is a concept from founder & designer Scott Hruff. In his model, each interface has 5 “personalities:” Blank, Loading, Partial, Error, and Ideal.

These are common blind spots. For pages representing collections of data, I also include a sixth “full” state. Imagine if your list had 10x the number of entries you would consider normal. What does it look like? Can it load quickly? Does it still function?

Wrapping up

Being more product-focused, in my opinion, leads to a more fulfilling programming career. On average, you’ll build better things, be more proud of your work, and get along better with your designers, managers, and stakeholders. However, where programming is logical and well-defined, “building a better product” is a more obtuse skill and requires a different approach to improvement. The three primary ways we examined were:

1. Heuristics - rules of thumb you can use to help you think differently and make better decisions. I think Heuristics is a smart default — they will serve you well 70% of the time, and when they don’t, that tells you something, too.

2. Patterns - raising your awareness of quality design, seeking it out, and internalizing what makes it quality.

3. Practice - Finding small ways to practice your product thinking in the real world. Questions, comments, and conversations are valuable, even if they don’t impact the final product.

We’ve all used software that felt thoughtless. Irritating software. Software that makes you do something manually that a computer could have done in a microsecond. It might just feel “off,” but you can’t put your finger on why.

Silicon Valley types love to talk about “changing the world.” but that cuts both ways—annoyance scales like value. Careless software makes the world just a little bit worse for everyone who uses it.

You have a responsibility to the people who use what you build.

As a software engineer, you are the last line of defense when it comes to stopping bad software from getting out in the world.

Every little thing you can do to make it better helps.

1

Work-life balance is off-balance. What people mean when they say “work-life balance” what they want is work-life boundaries.

You don’t want to be answering emails at 7 pm. You don’t want to hear screaming kids or yapping dogs when you’re trying to debug a PR. That’s fair.

It’s a challenge when working remotely, and you can’t escape to the office (or vice versa)

You can build boundaries around time or space to help. Have a dedicated office space; Let your family know when your focus hours are. In my office I have a ‘do not disturb’ door hanger, hotel-style. It lets my wife and kid know when I am heads down or on a Zoom call. I Walk the dog around the block at the start and end of every work day - a “commute” between work mode and life mode. He is still struggling to respect the door hanger.

But boundaries aren’t the only way.

2

Why must work be decoupled from life? What if work was something that enhanced your life rather than take away from it?

Hayao Miyazaki made The Boy and the Heron when he was in his 80s. He didn’t do it because he needed the money.

There’s work that interests you, that you are uniquely skilled to do, that you find compelling and enriching. Paul Millerd explores this idea in his book Good Work. There are ways to find work-life integration.

Or maybe it could mean separating vocation (work you do because you are compelled by the inscrutable exhortations of your soul) and occupation (work you do to pay the bills). This path is the most logical and fruitful for most I suspect, as it allows you to keep your art “pure” and your career optimized towards supporting you and your work.

I recognize that I do not contribute to world peace or solving hunger working in the financial services industry. I won’t pretend I enjoy it every day. But I find ways to make it work for me. I remind myself that our product helps people run their businesses with less friction. I find purpose in mentoring and coaching less experienced employees. My mandate also includes building and writing things that I’m proud of.I recently heard of a practice called job crafting, the art of tweaking your job better to suit your strengths, interests, and purspose.

3

What about the life half of the equation? What an oversimplification of our strange and beautiful existence. It can be broken down further with work-life decomposition.

Instead of a binary, many others have thought of life as a collection of several facets. Models include:

• John Maxwell’s Daily DozenAttitude, priorities, health, family, thinking, commitment, finances, faith, relationships, generosity, values, growth

• Zig Ziglar’s Wheel of LifeMental, spiritual, physical, family, financial, personal, career

• Tony Robbins’ 6 human needsCertainty, variety, significance, connection, growth, contribution

• Martin Seligman’s PERMA modelPositive emotion, engagement, relationships, meaning, accomplishment

• The 5 Fs FrameworkFaith, Family, Friends, Finances, Fitness

Take your pick or roll your own. Instead of balancing two things, these all frame life as a prism of physical health, personal relationships, financial security, spiritual fulfillment, emotional well-being, personal growth, making an impact, and sparking joy.

4

You can’t draw clear lines between the different facets. Each segment feeds to the others. I’ll, for consistency’s sake, call this work-life interdependence .

Career impacts money. Health increases productivity. Your passion for your job directly influences how fun you are to hang out with after work.

The separation only comes when you want to zoom in on one to make optimizations or improvements. But even then, you can’t do so without considering how it would impact the others.

Wrapping up

There are so many more interesting ways to frame how you prioritize your time and energy, set your intentions, and live your life. Thinking about “work-life” balance is limiting and guaranteed to make you off balance and bored.

We can't control the games, only how we play them

Some win conditions may change, while others are immutable. Strong bonds with family, friends and community are always a solid play strategy. Before it may have been about thriving, and now it may be pivoting to surviving or merely existing.

## Adapting with OODA Loops

Strategies have to change. Military strategist and former Air Force colonel John Boyd came up with the OODA loop model for making high-stakes decisions under duress: Observe, orient, decide, then act.

The faster you can complete these loops, the better your chances of success.

1. Observe: collect data. Get the best information you can and try to get to the most accurate interpretation of it. Understand the rules, constraints, and contours of the situation.

2. Orient: understand your position. Where are you at in all of this? What options are available to you?

3. Decide: form a new strategy. A hypothesis on how you can move towards your win conditions. What gives you the best chance of success?

4. Act: Test your strategy by taking action. Action provides information, usually the best information for you in your current situation and orientation. Observe. Now we're back to the beginning.

Sometimes OODA loops are small, sometimes they are large. They take the form of annual reflections, quarterly business reviews, or split-second decisions in a match of a Street Fighter 3 tournament.

It’s your move. Move forward

When the rules change, it's time to scrap or adjust old ideas. You may be frustrated or terrified into paralysis.

But that is never a winning strategy.

When the rules change, you may not like the new system but you may not have a choice in whether or not you play.

In these cases, the only was forward is to observe, orient, decide, act.​​​​​​​​​​​​​​​​

Especially act.

Checked in a large suitcase:

• Pack and Play—We have a basic Graco pack and play, and it has served us well. It assembles quickly and provides a clean, safe sleep space at night. I know a lot of folks recommend getting one from the place you’re staying or possibly renting one when you get there, BUT I cannot tell you the peace of mind I had knowing that he had a place to sleep and containment area during the day. I also packed a sheet for the mattress that comes with the PnP.

• Slumberpod— I thought I was being extra when I ordered this. Who needs a tent in a tent? But let me tell you, we did. We have used this for every trip since it arrived and it is a game changer when you are room sharing with your baby/toddler who is used to their own space. It allows me to move around hotel rooms and go to bed after baby.

• Sleep gear— We got a travel white noise machine, the baby monitor, though we couldn’t use it in our yurt, sleep sacks, and PJs. We also took everything we normally use for our bedtime routine—soaps, lotions, etc. We tried to make it as familiar as we could for him.

• Extra Food— He was nursing and eating several meals a day, but we weren’t sure we could always order something for him so we made sure to pack extra pouches and crackers.

• Extra diapers— After figuring out our average number of diapers, I packed those plus 50% more and man did they take up a lot of room.

Second large suitcase:

• Clothes for me and baby.

  • Packed a onesie for each day and then added 50% again. Onesies are the best- it’s a shirt, a sleeper, or a whole outfit if needed. Something is going to happen- food, poop or dirt, and it was wonderful having easy back ups.

  • Adventure specific items: we were hiking so I packed some sun shirts. And I always take a bathing suit! (Just a life rule)

  • PJs- packed a sleeper for every night- we ended up not using these due to the weather and relied on the onesies but it was good to have the option if it had been cold

Car Seat:

We purchased a second seat that was FAA-compliant. Even though we opted to travel with him in our laps, we wanted a seat that we could strap into a plane when the time came. It’s lightweight, seems to be comfortable, AND is super easy to install! We also bought a backpack carrying bag for the airport since we opted to gate check it on the way to our destination. You can rent a car seat, but for the cost of the rental, we now own a second seat for our cars, AND we know it’s clean and never been in an accident.

NOTE: we fully checked the car seat on the way home. We had a seat installed in the car at the airport at home so IF it didn’t make it back, we would be ok. However, I didn’t want to take any chances on the way to vacation.

Baby Carrier

Little man loves being in the carrier, and we tested his limits on this trip! This was amazing for getting around the airport and around town. We use the Ergo Baby Omni Breeze, which helped with getting on and off the plane as well!  Since we only have a large stroller, we didn’t bring it, but will be trying a travel stroller on our next adventure!

Carry on # 1, under the seat: The diaper bag:

This was stuffed to the brim with extras. What if we got delayed??? So I had too many diapers AND overnight diapers. We had a 4-and-a-half-hour flight, so along with boarding and deplaning we would be on the plane a little over 5 hours. I decided to change baby into an overnight diaper for the trip. We had no leaks and no solids, so we didn’t have to change on the plane!

TOYS: We packed some easy-to-reach toys and books for him that we could access when needed.

Snacks and water- we packed him a water bottle and tons of puffs and crackers to help keep him happy.

Carry on #2, overhead:

We packed additional toys and snacks in here. I wanted enough with us that IF the checked bag didn’t make it, or we were super delayed we could make it through at least double the meals we were missing. In hindsight, this was excessive. There are tons of options to purchase fruits and cheese at the airport. But for a first-time flight it did give me a sense of security.

On arrival

Yes, we were that family at baggage claim, two large suitcases, one small, one car seat, two backpacks, AND a baby strapped to us.

BUT, we also were the family that hiked Zion, slept in the yurt, and had an amazing family trip with a 10-month-old baby.

We had to bail on one dinner, but we knew we were pushing his limits as naps were thrown off, but that’s ok. I took him back to the yurt and watched the sun set over the mountains with a glass of wine.

Want to hear more from Kim? Let her know in the comments!

1. The Uncertainty Mindset : Innovation Insights from the Frontiers of Food

By Vaughn Tan

3 key takeaways

1. Innovation and efficiency are at odds with one another. Innovation requires experimentation and making mistakes, while efficiency requires removing these in favor of efficiency.

2. People conflate uncertainty and risk, but they are two different things. Risk always has an unknown element, but just because something is uncertain does not mean it is risky.

3. If organizations want to encourage innovative behavior, they should give people open-ended job titles and roles

2. Developer Hegemony: The Future of Labor

By Erik Dietrich

3 key takeaways

1. You get ahead not by working for other companies but by working for yourself. Even if you are employed and happy, you should invest resources in building your body of work and your network and be looking for new opportunities.

2. Even though it’s lucrative labor, writing code for a living is still labor. There is no leverage in slinging code for someone else.

3. Eventually, you should strongly consider moving away from development work in your career, into something higher leverage.

3. Four Thousand Weeks: Time Management for Mortals

By Oliver Burkeman

3 key takeaways

1. Time just happens— You don't own it, you don't have it, and you aren't really spending it, wasting it, or losing it. Enjoy the ride. If you are always future-focused and trying to instrumentalize time, you are never truly living.

2. Work is infinite; you are finite — There will always be more to do than you have time and energy to do. There is no moment of completion to race towards. There is no point where you will feel you "have it all together and figured out."

3. Serialization — Tackle fewer things simultaneously, and instead, start ordering your projects. If you can't do everything, doing fewer things to completion is better than having several half-assed, half-finished projects.

4. Die With Zero : Getting All You Can from Your Money and Your Life

By Bill Perkins

3 key takeaways

1. Think about the whole game — It's possible to guesstimate when you will die. Insurance companies do it all the time. Doing this, along with looking at the seasons, helps you think about your life more holistically. It also enables you to make the most of your time when you realize how much you have left.

2. Decumulation — at some point, the net worth number has to go down instead of up. Typically between the ages of 45 and 60. Huge psychological shift

3. Seasons of life —Your life has different seasons, and some experiences are enjoyed more during certain seasons. Some experiences are locked out of specific seasons. Big life choices like marriage, parenthood, and retirement also define seasons.

5. Working Identity: Unconventional Strategies for Reinventing Your Career

By Herminia Ibarra

3 key takeaways

1. Your working identity is something that does not reside internally. Instead, you have multiple possible future selves. The only way to discover these selves is by performing experiments that involve interaction with others.

2. At first, you will have several small possibilities. As some of them grow, they will begin to push out other identities. This includes your current self.

3. Act your way into a new way of thinking and being. You cannot discover yourself by introspection.

6. Tempo: timing, tactics and strategy in narrative-driven decision-making

By Venkatesh Rao

1. Tempo — Has three elements: rhythm, emotion, and energy. It’s not about conveying speed. It’s about conveying emotion.

2. Rhythm — Decision-making, business development, and life all have different rhythms. Changing these tempos takes energy. Staying at one tempo for too long can lead to boredom.

3. Narrative rationality — every decision is telling part of your life story. Your life will have rising and falling action and liminal passages. Make the choices that tell the most interesting story.

If you have any other books on similar themes, I’d love to hear about them in the comments below. I have a big flight coming up, and I need to load up my Kindle.

AI is already changing coding

I use AI every day. It needs to be carefully prompted, questioned, and reviewed, but it’s a productivity increase. I’d estimate it’s a 15-20% improvement. Does this mean that a company could cut headcount by 15% at scale without sacrificing velocity? Depends on the developers.

Here’s why it won’t put developers out of work

Technological advancement doesn’t destroy jobs; it mutates them. We’re adding more abstraction. If you are an engineer and want to keep it that way, start cultivating skills at a higher level of abstraction, like product skills.

Here’s what Gorman got right:

Product thinking skills are valuable now and will appreciate with time.

I’ve always believed in product thinking skills.

Instead of fretting about AI, spend that energy learning about usability, research, and business.

Knowing how to identify problems, clarify them, and develop solutions is an evergreen that will always be in demand.

P.S. If you’re a dev who wants to level up their product skills, hit me up here, on LinkedIn, X, or email. I’m working on something you might be interested in. 😉

Why is travel hacking possible?

Taken at face value, travel hacking seems too good to be true. Why would airlines just give flights away? Aren’t they losing money? What about credit cards offering $500 signup bonuses to customers who never carry a balance or pay interest?

Airlines and hotels are in a unique position where they have liabilities on their books (empty seats and rooms) they can position as assets for the consumer (free vacation woohoo!). They dole these out via points based on frequency of travel.

I used to think credit card companies made most of their money on interest and fees. Turns out they make more on the interchange(the percentage cut they take on every transaction, typically around 3%). High spenders are where they make their money, even if they don’t carry a balance.

They attract these high spenders by offering them a cut of the interchange, either in the form of cashback or points.

Credit cards also make money on partnership deals with other merchants. Put all of this together, and you get credit cards programs with travel portals where you can book travel, and transfer partners where you can exchange credit card points for points at airline and hotel points.

If you want to read more about how all this works, I strongly recommend Patrick MacKenzie’s piece Anatomy of a credit cards rewards program.

However, I would recommend not thinking too hard about the fact that these companies are still making money off of you, even when you’re travelling for “free.” Travel hacking is more fun from an iconoclastic mindset, and believing that you putting one over on major banks and airlines. I’m still sticking it to the man while I drink my piña colada on the beach, right? right?

In short, that’s the game here: pick a credit card, pick a preferred airline, pick a preferred hotel chain. Rack up the optimal amount of points on each, then exchange them to reduce the cost of trips you want to take.

Preferred credit card vendor: Chase

Many credit cards offer a signup bonus in the form of “if you spend X dollars in the Y months, we will give you some points.” These offers are your primary source of accuing value.

My current primary card is the Chase Sapphire ReserveAll Chase links are referral links (more hacks let’s gooo) card, though I use multiple cards in the Chase ecosystem. It has an annual fee of $550/year + $75 per authorized user, and it's well worth the cost. Signup bonus: 60,000 points have a rought “value” of for $4,000 of purchases in the first three months. Chase points are worth 1 centI’m anchoring the value here on cash back. You can trade 10,000 points for a $100 statement credit. But ultimately points are worth what you exchange for., so you could think of it as a $600 signup bonus.

Every year, you get a $300 travel credit and a 1.5x multiplier on points exchanged for travel(so that $600 bonus could be worth $750), among other benefits, such as access to airport lounges via Priority Pass. I will leave the valuation of free time-unbounded airport beer and mid food as an exercise for the reader.

Many people balk at the high annual fee, but if you’re using all the benefits, it pays for itself.

Other types of Chase cards will also earn ultimate rewards points and have a $0 annual fee.

1. Chase Freedom Unlimited - $0 Fee and 0% APR for 15 months. Useful if you want a card with no fee to earn ultimate rewards points. Chase actually two kinds of points, and you want to avoid the much less value Amazon rewards points.

2. Chase Sapphire Preferred—$95 fee, 1.25x travel multiplier. Also offers 60,000 points for $4,000 spending in the first 3 months. This is a cheaper alternative to the preferred with fewer rewards, but you can use both bonuses if you like (within Chase’s limitations; see below).

3. Chase Ink (business unlimited or business cash) —$0 fee, 75,000 points if you spend $6,000 in the first 6 months. Unlike other cards, there is no rule against holding multiple Chase Ink cards, and they don’t count against your 5/24 limit. They are for "business," but you can use an SSN and get one as a "sole proprietor.” One new card every quarter seems to be the safe spot.Untested by me, but that seems to be the consensus on Reddit.

You can transfer points between cards and between household members, but you will need to call customer support to do the latter. You can get the 1.5x multiplier on all Ultimate rewards points, regardless of which card earned you the points. If you get 2 Chase cards, that's 150,000 points. With the Sapphire reserve multiplier and travel credit, that’s $2,550 in free travel bucks right there.

The biggest controllable factors for points accquisition is the number of signup bonuses you're willing to churn through and how frequently you’re willing to go update all of your payment settings.

How many credit cards can you open?

It depends. You should be aware of the 5/24 rule—if you open more than 5 personal credit cards from any issuer in 24 months, Chase will not let you open new cards. Opening 2 cards in a 30-day period could also get you flagged. Generally, one credit card every 4-5 months is safe.

These rules apply to individuals, not households. You and your spouse can double-dip and even send each other referral links.

Tips for managing multiple credit cards

1. Keep a spreadsheet of when you open every rewards card and when they expire. Set reminders to cancel credit cards with annual fees you don’t want to keep. I try to only have one annual fee active at a time.

2. Make a spreadsheet of every recurring bill you have and every online merchant you frequent, with links to their payment pages. This will make it easier to switch cards.

Games you can play with cash flow

1. This should go without saying, but don’t spend extra “for the points.” That’s how you lose this game.

2. If you have a large ($2,000+) purchase coming up, that’s a good time to open up a new card so you can get through the bonus quickly. You probably aren’t paying for 100% of your travel this way, so booking a trip can be a quick way to jump-start this process.

3. Time spending with opening new cards. Hold off on optional purchases for a few weeks, then make them all at once when you open a new card.

4. If you are approaching the end of a bonus’s time limit, buy gift cards for recurring spending you would make anyway, such as groceries and gas.

Preferred Airline: Southwest

Two free checked bags, CrowdStrike immunity, what’s not to love?

Southwest is a travel rewards partner with Chase, so you can transfer points 1:1 from Chase to Southwest.

I will say airlines are the place I’m the least picky. I will happily fly Delta or AmericanFuck Spirit if it means one less layover or a more convenient departure times. Another part of travel hacking is deciding how you want to balance quality of the journey vs. price.

Flight booking tips

1. I use the ITA Matrix search to compare flights.

2. Always have a frequent flyer number with every airline you fly with. Use it with business travel if your company allows.

3. If you have a child, be sure to set up an email address and frequent flyer number for them as well.

4. Always check the point cost of booking through Southwest direct and the Chase travel portal. You never know which one will be cheaper.

5. Do not buy points from Southwest. They have one of the worst rates, charging you 2-3 cents per point, and redeeming them at 1.

Preferred Hotel Chain: Hyatt

Hyatt has decent coverage, is a travel partner with Chase, and is the key to getting maximum value for your points.

Firstly, Hyatt values points at roughly 2 cents compared to Chase’s 1 cent, but you can transfer them 1:1.

Secondly, unlike airlines, which use an inscrutable calculus to determine point values for flights, Hyatt has a fixed system.

Here’s an example: As of this writing, I found a room at the Andaz Maui at Wailea Resort for $871 dollars/night, or 40,000 points. That means if you followed the Chase steps outlined above, you could have 3 nights in a Hawaiian resort for free.

• 40,000 points exchanged for cashback = $400, 1 cent per point

• 40,000 points spent in travel portal = $600, 1.5 cents per point

• 40,000 points on Hyatt resort = $871, 2.1 cents per point

If that sounds interesting, Hyatt also has its own rewards cards, which are good for another 60,000 Hyatt pointsIt's worth noting that hotel and airline points are less flexible than credit card points. You can transfer Chase points to Hyatt, but not the other way around..

Booking hotel tips

1. I like TripAdvisor or the native Hyatt app for finding hotels, but I always book through Chase Travel (if spending points) or through Hyatt directly (if spending cash).

2. Hyatt will sell you points for 2.4 cents each. It might make sense to buy them if you trying to book a higher-end resort.

3. I like resorts, so I try to refrain from cashing in points on regular hotel stays and save them for nicer places.

What if I prefer staying in AirBnBs or short-term rentals?

Pay cash, sorry.

Preferred tertiary travel booking: Costco

Costco travel is legit, y’all.

There are no points games to be played here, but you can find good rates on hotels, vacation properties, and sometimes flights, especially if you get a package deal. If you have an executive membership, you’ll earn 2% cashback on bookings. Many will include a gift card as well, so it still feels travel-hacky.

Take the package below; it costs $3,197, but once you factor in the gift card and the 2% back, it’s effectively $3,021You could take this a step further and factor in 1% points earnings and say it’s really $2,989, but I digress..

If you have an executive membership, I’d give it a look when exploring trip ideas.

Other things I don’t do that are also probably pretty good

There are only two credit card companies that are competitive with travel rewards, the other one being American Express. I haven’t messed with them, but they did just build the biggest Centurion lounge in Atlanta, so maybe I’ll try them in the future.

Hilton has a similar fixed point system to Hyatt, along with their own rewards cards.

Based on your nearby airlines and travel preferences, maybe those are interesting to you. But I haven’t tried them, so I can’t describe how well they work. However, the same general strategies outlined above should still apply.

Summary

In short, you find credit cards you like, chrun some offers, get some points, move ‘em around, save a few thousand bucks. Pretend you put one over on multiple mega corporations even though they made their money on interchange and in-flight beverages. Have fun! If this was helpful, I’d love to hear about it. tell me about your trip!

Falsehoods investors believe about the efficient market hypotheses

There are two big false assumptions from the “VSTAX and relax” crowd about investing in the stock market for the long term, and those are:

1. You have to invest in the stock market

2. It has to be long-term.

There are other places to put money to work, and it doesn’t have to be long-term. There’s nothing wrong with locking in a quick win every now and then. A strategy isn’t worthless because it won’t work consistently for 30 years. Really, what do strategies in life do? The job I have now didn’t exist 30 years ago and likely won’t exist 30 years from now. (I give it 3-5 years, tops).

Finding one-off exploits is a worthwhile pursuit. Any system that behaves this erratically has to have exploits.

That’s one of the neat parts about being a human being. We are finite creatures in a system designed for infinite growth. We don’t have to compound our investments forever, just long enough to get us to the end and set the next generation up for success.

A more sincere disclaimer about index funds

I feel I should point out that I have most of my assets in low-cost index funds. I am not trying to pretend that I am someone from /r/wallstreetbets who makes ridiculous options bets. Index funds are boring than they work. I am in my late 30s, I have a kid, I have to regulate may moonshots and gambles to a few points of the overall portfolio. But I take some inspiration from Nassim Taleb’s barbell investing: I have a majority of my money in conservative bets, but I am always willing to put 5-10% on more aggressive plays.

Common Sense only works if you want to make a common amount of cents

The Common Sense Book of Investing was written before we shifted away from an information economy and towards an attention economy. If you can get enough people to pay attention to something, that’s worth something. GME is not a bet. It’s a story. Dogecoin is buying a joke that is worth more, and people are laughing at it. It’s a derivative of Matt Levine’s Elon Markets hypothesis.

Thriving in the new rules is greatly understudied and undertheorized, in my opinion. Plenty of alpha out there to dig up.

There is no invisible hand. There is only human behavior. The market is a mirror collectively facing us. When we look at it, what do we see?

What does it say about what we’ve become?

And most interestingly, how can we at least profit from it?

The constraints of indie and the liberties of the rat race

I was surprised that while I gave up some freedoms, I gained others. When I worked independently, there was no such thing as paid time off. When I wanted to take a vacation, I had to talk to clients first. It usually involved doing extra work before and after the trip. But now I was part of a team. I could leave for a week, and things just… got done? The wheels kept spinning.

When you bill hourly, some weird psychological effects change how you perceive time. Every hour you aren’t billing is, in theory, one you could be. Leisure feels expensive. You tell yourself that if you double your hourly rate, you could work half the time. But the opposite happens: free time now feels twice as expensive, and you are even more disincentivized to take it. With a salaried position, it was much easier to leave work at work.

Justin Jackson has some thoughts on how a full-time job can be more “freeing” than bootstrapping a business, especially if you have children.

https://twitter.com/mijustin/status/1464702720456073216

Charlie Munger took a similar approach with his law practice. Even though he was part owner in the firm, he saw it as a foundation for other pursuits. From Poor Charlie’s Almanack:

I realized that freedom is not binary. Freedom is categorical. No matter what kind of work or lifestyle you take on, you are trading some kind of freedom for another. In this essay, I want to examine the multifaceted uses of freedom in work, life, and craft. How would different ways of making money affect the types of freedom I have in various parts of me life? An initial attempt at mapping them out:

Different income streams in their freedoms

1. Full-time employment: It has low ownership and responsibility. Consistent paychecks and healthcare provide a nice foundation for other pursuits. However, I have little say in what I work on, when, and who I do it with.

2. Freelancing: More freedom in what I do and who I work with, but you’re still beholden to the client’s whims and timelines. On less consistent financial grounds. Free time feels like free.

3. Selling a product, book, or course provides the highest amount of ‘freedom in work,’ but you are beholden to consistently marketing your product. Your income is only “passive” as long as you stay on the content hamster wheelHowever, after reading Write Useful Books, I realized there may be ways around this. It sounds good to build a flywheel of referrals and word-of-mouth, but that’s a whole undertaking in addition to creating a prescriptive non-fiction piece of work.. Without a boss or a client, you are 100% responsible for managing the work and product.

4. Owning a rental property: This is the only option where generating equity and cash flow is fully divorced from your laborAssuming you’re working with a property management company and contractors. You could rent a place in your area and handle everything yourself.. However, now you have a financial burden of ownership. If your property is vacant or the HVAC system dies, you’re on the hook. You’ll need more cash in an emergency fund for such events, so you are less free to use that money elsewhere. If you’re handling things yourself and need to stay local, you have more restrictions on where you can live and travel.

5. Running a software product: Customers’ 99% uptime expectations mean you are either on the hook for hiring someone to babysit your servers or can’t truly relax during vacation until you do. In exchange, you get the highest financial upside of the options presented.

From here, what different flavors of freedom can I suss out?

7 Flavors of freedom

1. Freedom from work: This is what FIRE people are chasing: not being required to work 40+ hours a week to exist.

2. Freedom in work: How much say you have in what you do when you do it and whom you do it with.

3. Financial Freedom: I’m distinguishing here between freedom from work because, as we’ve seen, a steady paycheck that covers your needs is its own kind of freedom.

4. Freedom of time(amount): How much leisure time do you have in your life?

5. Freedom in time(flexibility): Hours of free time are not created equal. If all of your friends work 9-to-5, does it matter that you don’t? Social relationships are dependent on the people involved having leisure time that’s in sync.

6. Freedom of location: Are you working remotely or from home? Are you able to take advantage of your remoteness? Does your work enable you to travel how you want? Does it require more travel than you would prefer?

7. Freedom from responsibility: When you are a team member at a full-time job, you can go away for a week, and the gears will keep turning while you are away. If you are a solopreneur, you either have to have contractors and systems in place or do double work before vacation and never fully relax during it.

I’m still riffing on this idea. It doesn’t feel complete, but it does feel more useful than that “free as in speech / free as in beer” model.

What do you think?

Are there other flavors of freedom I’m missing?

Which ones are most important to you?

Which ones are you willing to sacrifice for others?

This post is part of a series on money and agency. Read the other parts here:

Financial Independence as Philosophical Suicide

Creative fire, destructive fire

Other writing

In addition to the newsletter, I’ve added notes to my digital garden: my public notebook of random thoughts and collections. This month, I’ve been thinking about using data effectively, asset allocation, and writing as a social practice.

Also, inspired by a conversation at a local dev group, I put together a small collection of resources for developers who want to start learning about design on GitHub. Stars, PRs, and comments are appreciated.

Choice reads

🎮 Scrubs and Scrub Behavior - “A scrub is a player handicapped by self-imposed rules that the game knows nothing about. A scrub does not play to win.” I” 've been thinking a lot about what kind of scrub behavior I’ve observed in myself and others and what I can do to eliminate it.

🤑 Fools and their Money Metaphors - I’ve been on a big Venkatesh Rao kick and reading old Ribbonfarm essays. This one felt apt for including what I’ve been talking about recently: our psychological relationship with money.

✍️ **On Opening Essays, Conference Talks, and Jam Jars—**This is a big level up that I’ve applied to everything I’ve written on this Substack this season. Writing interesting openings not only helps me engage the reader but also compels me to write a more compelling piece to fulfill the opening’s promise.

👩🏻‍💼 Allea’s thread on business agency - Using capital is a skill, and it’s one that you don’t pick up from books. People who grow up in more privileged situations are privileged because they have access to mentorship and coaching that you can’t buy. As someone who has lived through it, I am always hungry for more. I “grew up poor, made some class jumps, now I feel lost, confused & alone” content. Whatever genre that is, I am here for it.

Two quick anecdotes

I’ll leave you with two little stories, each exemplifying fire as master and fire as servant.

1. I talked to one friend who was a prolific writer online, typically in service of the products he’s selling. I asked him if we would still write if he had fuck you money. “I would write SO MUCH MORE if I were truly FIRE,” he exclaimed.

2. Someone mentioned they had a friend who achieved FIRE. A few after he announced that, his friends invited him to dinner at a Mexican restaurant. “I’m not paying for restaurants anymore,” he responded.

Camus, Suicide, and the Absurd

In The Myth of Sisyphus, Camus describes the concept of “philosophical suicide.” This term refers to accepting beliefs or a system of thought that provides absolute, ready-made answers to life's fundamental questions. These systems ultimately deprive the individual of freedom and responsibility for their existence.

To Camus, life is absurdly meaningless. The best way to tackle that absurdity is to face it, accept it, live authentically, and build meaning.

Philosophical suicide is turning your head away from the absurdity and denying its existence. Accepting a rigid belief system gives you an excuse to check out.

Never think for yourself,

Never figure out who you are.

Never truly live.

That’s what FIRE is—a set of answers that are ultimately not about money but about life.

What do you do for work? It doesn’t matter if it provides enough money to help you retire. Work cannot bring joy; it’s a burden to be discarded. What do you do with your money? Index funds, mega backdoor ROTHs, VSTAX, and relax. Everything else is a sin.

It’s a philosophy of non-doing. It rejects late-stage capitalism while being obsessed with money.

An escape mechanism.

FIRE promises freedom, but not in the way people think

While FIRE promises independence and freedom (whatever that means, we’ll get to that in a bit) in the future, it provides a type of freedom today. Saving is easy, but leveraging capital to live a more authentic life is hard. FIRE frees you from the anxiety of deciding how to spend your money.

If you focus on retirement, you can kick the can on investigating what you want out of life. You can avoid finding or making meaning in work. Why get anything out of life now that every day could feel like a weekend in 2050?

Here’s a fun question to ask yourself:

If you received a windfall of $100,000, free and clear of taxes. What would you do with it? One caveat: you cannot use it to invest in the stock marketThis includes workarounds like spending it on your mortgage and re-investing the payment..

Your answer must be specific. “Travel” is insufficient.

It’s a surprisingly difficult question. Asking yourself what you want out of life requires self-knowledge and exploration.

Saving is easy. Figuring out what you want out of life is hard.

When the FIRE burns out

I’ve seen the outcomes of this on Reddit. People get their number, can retire, and then what? Some people get depressed and don’t know how to fill their days. Others go back to work. Others still decide the number needs to be higher, and they aren’t at the end yet. Some choice quotes:

• “I regret my whole life. I had an unhealthy fixation with money but wouldn’t spend it.”

• “I didn’t take any risks in life. I did not experiment socially with dating, networking, or travel.”

• “Saving was easy because I didn’t do anything.”

They pushed all the living and figuring out who they are to the end, and now they don’t know how to handle it once they are there. Once you’ve committed philosophical suicide, it’s hard to come back.

If you want to hear what this sounds like, check out this episode of I Will Teach You To Be Rich: We achieved FIRE with $4.3M. Why can’t we enjoy it?There is a downside to blogging about trying to get financially independent. When the blog makes enough money to get you to your number, what the hell do you write about next? Imagine having 4 million dollars in the bank and booking a flight with a 4-hour layover to save twenty bucks. That isn’t frugality; It’s insanity.

Passing a milestone in the bank will not change who you are. While there is some truth to “you can’t beat the market,” and there’s nothing wrong with investing in index funds regularly, it’s still a lazy way to think about moneyI want to write a whole other piece on this, but in short, even if you can’t beat the market, there are plenty of other ways to gain leverage outside of it..

Work can be a drag, obviously. There is no denying that most jobs are meaningless and absurd. But it can be a craft and have a purpose if you let it. At some level, you must participate in your survival, which means providing value to others.

FIRE is an ultimately selfish philosophy, another reason it leaves people feeling unfulfilled. The spreadsheet will never love you back. People would be better served finding ways to make meaning from work instead of trying to forgo it altogether. Even if the only meaning you find out of your 9-to-5 is “This is what I do to bankroll the things I am passionate about.” that’s a start.

What we can learn from FIRE

I want to be clear that there are some worthy lessons to be taken from this. FIRE is a lot of people’s introduction to financial literacy. Having decent savings rates and putting money into tax-advantaged savings accounts is a profitable strategy and perfectly cromulent smart default.

I went through a Mr. Money MustacheThe original writer, Peter Adeney, no longer maintains this blog. He sold it. I suppose that’s one exit strategy for indie finance bloggers. (one of the most prominent FIRE bloggers) phase, and stories about $20 swims made me think twice before making large purchases. He also showed me that there is no 1:1 mapping between dollars spent and happiness gained or utility earned. Walks with my family are free. The biggest wealth is your physical and mental health.

All of these are a fine financial foundation. My critique is when these beliefs become an obsession, a limiting belief, or a copy for your shitty job.

You do whatever you like. Live!

LIVE!

At the end of the day, if you are searching for external solutions to internal problems, then you’re looking in the wrong place. No number in a savings account will ever change your relationship with money, time, work, or death.

Ask yourself questions to determine what you can get out of time now.

Out of work now.

Out of your money now.

• How can I find joy in my craft?

• Looking back at the past year, when did I feel most alive?

• Looking back at the past year, what am I most proud of?

• If I hit my “number” today, what would I be doing in three months? What’s a version of that that I could be doing now?

• How can I leverage money and work to make meaning in this absurd existence?

Feel free to post your answers in the comments below 👇

(Not financial advice, obviously.)

Where did all these people go?

These jobs were “destroyed,” so what happened to the people who had them? They went to one of three places:

1. outside the platform - Agencies move to other services, such as content, SEO, and managing ad spend.

2. inside the platform - Building plugins, themes, and apps that leverage these new platforms at a greater scale.

3. above the platform - Engineers move on to solving bigger problems. Building web and mobile applications replace some websites.

When jobs die, more take their place. Technology has replaced jobs several times over.

AI Isn’t going to ruin me financially. But I am confident that in 2-4 years, I won’t have my current job because it won’t exist in its current form.

AI isn’t going to change software development — it already has

I had a lightbulb moment with AI. I was about to assign a ticket to a junior developer when I realized that “Oh, ChatGPT could write the function that does this.” I still gave it to them, but that’s when I realized that ChatGPT has a place in my workflow.

If you can break a piece of work into a small function that requires limited context, there’s a good chance ChatGPT can write it for you and write it faster than you can.

Post by Swizec Teller writing a book you’ll wanna read (@Swizec)

Knowing the tools

There is a skill to using these tools in work. I think the term “prompt engineering” is a little cringe, but it is a skill. Tech-savvy millennials have long known their biggest superpower was being better at Googling than 90% of people. Now we need to be better at prompting than 90% of people.

Bonus points: if you write a good prompt for a function, you’ve also written the documentation for it.

Final mile work

Why do companies still employ so many web developers when so many tools & open-source modules exist? The two reasons are context and stitching. Yes, there is a plugin that can make an input form easily handle credit card numbers and add commas to large dollar amounts, but how does that fit into a larger-scale financial application? There are plenty of off-the-shelf solutions, but they either need to be tweaked, modified, or extended for particular use cases.

The more greenfield your work, the more useful AI is at coding it. Right now, it’s great for piecing together demos and simple greenfield projects. The bigger your current application, the more difficult integrating ChatGPT into your workflow.

I, for one, welcome our robot overlords.

ChatGPT isn’t always perfect. The generated code still needs to be tested, refined, and fit into a larger context. Sometimes it takes a few iterations with ChatGPT to get a workable solution. This isn’t a knock against it - so do humans.

Sometimes the code will have bugs in it. So does code written by humans. Some people online are resistant to generative AI, putting all of their efforts into laughing at how stupid it can be and zero effort into thinking about how they prompt or what they say at all. A revolutionary tool comes out, and all you can do is be negative. Why?

The only explanation I can come up with is that being negative is simply easier.

Personally, I’m excited to see what my work looks like in two years. And besides, if machines are doing all the boring work, we have no choice but to get more weird.

A disturbing chart

yeesh.

And finally, a moment of gratitude

Post by Visakan Veerasamy (@visakanv)

So… now what?

Technology is an infinite game. Unicorns come, and unicorns go. I’m excited to see what the future holds as the next generation of talent phases in.

For me personally, I’ll see where I fit into the new tech scene or if I leave to go sell pickles at a farmers market or start a dad rock band or buy a jet ski.

Top score

Post by Glenn Stovall - statetransition.substack.com (@GSto)

I’ve written so many threads met with silence. Clearly, my time on Twitter would be better spent coming up with quips in the replies.

A quality slideshow on TikTok

A friend sent me this TikTok about the “dark arts” of office politics and said it reminded him of my piece on ethical office politics. I loved this take and would highly recommend giving it a watch. Also, we’re doing slideshows on TikTok now? I don’t understand the new social medias.

You can also read it on Substack, which I assume is an app where you’re comfortable consuming content.

A moment of gratitude

Thank you to Elon Musk and others for asking for a 6-month pause on AI development. They must of have heard my plea last week and are giving us all some time to catch up. Otherwise, fuck that guy though.

Developers, sometimes you try to jump into a technological window

There’s a space when being an early adopter of new technology can be a huge boon. Look at the first iOS developers building the first apps. They made a mint. AI could be the same thing. Or it could be just a productivity tool, or it’s going to kill us all. Who’s to say?

How many times in one career do you get to be one of the first in an app store?

Remember DeFi summer? Remember web3? Remember the metaverse?

Technology windows are like meme stocks, once you know they’re going to succeed you’re already too late. So you have to make bets and hope it works out. I had a lot of freelancing success being one of the first Angular developers in my community, as an early adopter of modern web application frameworks. I also wasted a summer learning Adobe Flex. Ever heard of adobe flex? Exactly. The iOS guys were better than me at identifying the Flash killer.

So what am I, as a senior software engineer / not-a-journalist-but-I-play-one-online? I feel behind as soon as I start.

When looking at a potential technological window, where does one begin? here are the questions I am trying to answer:

• what are ways I can use AI to increase productivity today?

• what are useful tips/tricks/prompts I should be aware of?

• what opportunities exist for developers in the current ecosystem?

• how might AI change the work I’m doing currently?

• how can I keep up with the rapid rate of change?

• how much of my time and energy should I dedicate to this?

• what are the risks of using AI in my work?

• what are the societal and existential risks of AI?

one strategy could be to try and follow people who are high signal and trust their curation. I’ve been cribbing from Swyx mostly, author of the Latent Space substack. He has a collection of AI notes and a high-signal Twitter list. At least it’s a start.

Probably time to start building something. I don’t know what. But I can’t shake the feeling that is going to change something.

I’m reminded of a line from the Ribbonfarm post about premium mediocre:

Now the boundaries are moving. You’re either above the LLM or below the LLM

A good tweet

Post by Laura Wendel (@Lauramaywendel)

Creativity - you can’t know the destination until you get started

Writing got easier when I realized I wasn’t supposed to know how an article would go until I started writing it. “plan, then execute” is not the pattern most creative processes follow. Instead, execution and discovery are tangled in a way that makes this impossible. When you don’t know enough to plan, the best option is to get started.  The software industry started to see the contours of this with Agile:  One of the values is “Responding to change over following a plan.” Agile has many failings, but at least it acknowledges that the creative process requires uncertainty and disorder.

Your creative vision is always a little bit ahead of your execution, as it should be. You can’t know what you will create until it’s done. And each piece informs the next - the goal of most work turns out to be research & development for the small percentage of your work that is truly great.

I want to draw a distinction between creativity and innovation here. Creativity is the act of creating something where that was nothing. Innovation is navigating uncharted territory. Writing, painting, coding, cooking, and entrepreneurship are all creative acts. It’s about putting your soul into the output of the world. Innovation is doing something new. While they are different, they are often tightly coupled, so it’s no surprise that disorder also plays a role in innovation.

Innovation is required for novelty and style

Innovation makes your work distinctive. It gives you a competitive edge. What would your work look like without it?

This kind of uncertainty is particularly challenging for large companies. Companies gain an appetite for process, metrics, and standardization as they grow. Weapons they plan to use to keep Disorder at bay.

Uncertainty is more advantageous at startups and less desirable the larger and more established a company gets. Companies have more to lose, they get risk avoidant.

This philosophy holds at the personal level. The less you lose, the easier it is to embrace Disorder. This is why it’s harder to start a startup after getting a well-paying job than when you are young and broke.

Being comfortable with uncertainty is a competitive advantage

We’re all working with the same outdated firmware. Learning to outthink your caveman OS is something most people can’t or won’t do. If you can, you have a competitive advantage.

In fact, research shows that people will avoid financial upside if uncertainty is involved, even if they know it is advantageous to do so:

"Despite it being the more rational option, only 37% of the participants opted to wait on every single trial. The rest were willing to take a financial hit to avoid the anxious waiting state of uncertainty."

In prospect theory, this is called The certainty effect: people are drawn to sure things over probabilities, even when the probability is a better choice.

Avoid uncertainty can lead to making the wrong decision

Imagine you are surfing waves in the ocean. You cannot decide when to catch a wave or how big it will be. The ocean has the final say. There's no arguing with her. You have to work with it instead of trying to timebox it into your schedule.

You have the best chance of success by working with forces outside of your control instead of against them. By watching the waves instead of trying to control them, you can see the ocean more honestly for what she is.

Some fields require precision, like astrophysics and flying plane. Other fields, including any that involve the vagueries of human emotion and bias, are seas of uncertainty. You can't change human nature; only learn to navigate it.

When you learn to accept uncertainty, you can evaluate some decisions under a new framing: Am I doing this because it reduces uncertainty, and do I need to be doing that here? To summarize a previous post, sometimes trying to reduce uncertainty increases it.

Preparation over prediction

This doesn’t mean throwing caution to the wind. There is still real risk in the world. What I am suggesting is that you stop trying to control what you cannot. Focus on preparation over prediction. I love aggressive gambles, but I have an emergency fund and a life insurance policy. Having sufficient preparation in place is required to take some chances.

That’s why emergency funds are common: No one knows exactly what the emergency will be when it happens or its intensity. But we recognize that given a long enough time horizon, "unexpected" emergencies are guaranteed.

To reject uncertainty is to accept death

What is death but the absence of change? If accepting uncertainty is required for growth and change,  then rejecting it in favor of comfort is accepting stasis and, eventually, death.

As companies grow, they desire to standardize. More people get larger and unwieldy. They do this via standardization. Companies have more to lose; they get risk adverse. But as a trade-off, standardization leads to a decline in innovation and creativity.

As I am writing this, $GOOGL is down 8% after a disappointing showing of AI. They standardized on being an ad-based business. They had an internal process that rewarded new projects but not supporting them. The end result is a company that can no longer ship new products.

Vaughn Tan nails it in The Uncertainty Mindset:

This is why, in my opinion, planning and OKRs are overrated. The world is too random and unpredictable for 2-year roadmaps. The better strategy is learning to improvise and to adapt to environmental conditions. To get comfortable with uncertainty.

To accept uncertainty is to be more alive

The fact that most people can’t conquer their lizard brains makes being someone who can be superhuman. You’ll be more perceptive, more adaptive, more creative, more innovative, and more resilient.

And it’s a hell of a lot more fun, I promise.

5 unproductive responses to uncertainty

1. Inflated estimates of threat cost and probability -  overestimating the risk and cost of taking or not taking action

2. Increased threat attention and hypervigilance - Running through increasingly unlikely “what if?” scenarios, exaggerating the intensity of every threat signal.

3. Deficient safety learning - Ignoring signs that you are safe or signals the threat has passed.

4. Behavior and cognitive avoidance-  Running away from problems instead of facing them head-on.

5. Heightened reactivity about threat uncertainty - Letting problems get to you. The uncertainty caused increased feelings of anxiety or depression.

How responses feed the tailspin

These responses cause a negative feedback cycle.

1. Avoiding low-downside, high-upside risks due to not recognizing how low-risk they are.

2. Over-indexing on threat signals and under-index on safety signals causes the perception of more threats, real and imagined.

3. Avoiding problems, allowing them to fester.

4. Wasting time and energy worrying about potential outcomes instead of preparing for them.

Some examples:

1. A person grows up poor with little exposure to investing. They view the stock market as ‘too complicated,’ ‘risky,’ and ‘basically gambling.’ When they find themselves with a little extra money, they don’t invest it, leading to less money and, therefore, more financial stress in the long run.

2. Someone sees a small lump but fears seeing a doctor about it. A treatable condition gets worse because it was ignored.

3. Unsatisfied at their job, a person doesn’t apply anywhere else because they think the time to interview and the pain of getting rejected, in exchange for an opportunity to improve their salary and quality of life, is “not worth it.”

What are some examples of people reacting to uncertainty or risk that caused them to experience even more?

What to do instead

Tailspins can be avoided or clawed out of one by simply doing the opposite of the extreme reactions in the UAMA model:

1. Accurate cost, risk, and probability estimations - or at least as accurate as possible.

2. Responsible attention to threat signal - Be aware, but don’t be myopic.

3. Observe safety signals - are there signs you are ok? Can you trust them?

4. Face problems head-on - If you can take action, then do so.

5. Manage emotions - Don’t let uncertainty get to you. Approach it was a calm, rational demeanor.

Facing uncertainty doesn’t mean you have to be uncomfortable.

In fact, Learning to be okay with uncertainty is the first step to understanding how it can be a tool:

A source of discovery, wonder, and innovation.

Risk vs. variance

Risk is the possibility of losing something. Variance is the spread of possibilities of an outcome. Variant outcomes are more uncertain but not always riskier. For example, if you get a free raffle ticket, you have an investment in a highly variant outcome (the raffle) with zero risk.

Another example of high variance and low risk is publishing. You can write or build something to share on the internet. Most of the time, no one will notice. But the times they do, it can open up huge opportunities.

Sometimes, trying to reduce variance can increase risk

I was once an active poster on online poker forums where people would discuss strategy. Once, someone asked, “how can I reduce risk in my game?” They wanted fewer swings in wins & losses, even if it meant a lower average win rate. After some discussion, an experienced player pointed out that the player was looking to reduce variance, not risk.

They could play it safe and reduce their average wins and losses, reducing variance. However, by reducing their average winning rate, they were reducing their long-term success and would increase the amount of risk they would face. A lower win rate increases the chances of eventually going broke.

Uncertainty vs. the unknown

If something is unknown, you aren’t aware of it. If it’s uncertain, it means it cannot be known. Many people’s first introduction to these distinctions comes from Donald Rumsfeld’s response to a question during a 2002 news briefing (emphasis mine):

I would argue there is a fifth category, can’t know. I’ll go back to the publishing example. There is no way to know what will be a hit in the market until you put something out there. It takes a combination of timing, fit, and luck.

Miles Davis, one of the greatest jazz musicians who ever lived, said he had to write 88 songs to write one hit.

Dealing with the unknown is easier and can often be tackled by research or experimentation. Uncertainty is more difficult and existentially threatening - we can only accept that it exists and learn to accept it.

On complexity, illegibility, and randomness

Everything so far describes outcomes; now, let’s look at a few ways to describe the workings of systems and events that cause said outcomes.

Randomness defines a lack of pattern or predictability. Complexity is defined by the number of rules, variables, parts, and the relationships between those parts in a system. Illegibility is about the definition and understandability of a system.

The stock market is complex, but I wouldn’t call it random. It’s a group of people making decisions based on their best predictions. But since there are so many actors and factors, it being non-random does not make it any more predictable.

Complexity tends to add uncertainty. More parts, relations, and second-order effects make it harder to predict what a system will do.

Complexity also tends to add risk. The more moving parts, the more that can go wrong. Conversely, the more guardrails and backups you can have.

Complex systems also tend to be illegible.

Systems that are too vast to hold in our hands or are difficult to measure. Sometimes they seem more understandable on the surface until you get into the details. Did you know we don’t know the length of the California coastline?

(Illegibility is at the heart of why every software estimate is wrong, but that’s an article for another day.)

To surmise:

The glossary of disorder

Complexity

The number of relationships and dynamics within a system. The more complex a system gets, the more illegible it tends to get. The more expansive and interconnected the system, the more events cause unexpected second-order effects, which ripple through the system. Complexity increases uncertainty. It may increase risk.

Illegibility

Illegibility refers to a system lacking definition. It's complex and filled with ambiguities and irregularities. Social dynamics are illegible. Changing a system to make it more legible can increase risk or reduce its value.

Risk

The chance of losing something. The possibility of losing everything is called the risk of ruin. The opposite of risk is reward.

Uncertainty

not knowing what is going to happen next. There's a distinction between uncertainty and not knowing. No knowing is incomplete for perfect knowledge. Someone out there knows it, but it's not you. Who is going to win the super bowl in 2035? That's uncertain. Will there be a super bowl in 2035? Less uncertain than the previous question, but the future is not guaranteed.

Unknown

different than uncertainty because it can be known. Unknowingness comes from incomplete information (in poker, we don't see other players’ cards). or imperfect information (when talking to customers, we don't know what they need, only what they tell us they need).

Randomness

Randomness is a characteristic of an unpredictable system. A genuinely random process will have high variance, but a process with high variance does not necessarily mean it is random.

Variance

Variance is the measure of the spread between outcomes. A 20-sided die has more variance than a 6-sided one. Just because something has more variance does not mean it is higher risk. Risk is the chance of loss or harm, variance is the spread of the range of possibilities. The opposite of variance is stability.

Every significant move in my career I made by playing up:

• Noob to small-town agency hack: First, I got a job at an agency when I barely knew about web development.

• Small-town agency hack to government contractor: Then, I moved into a larger corporation and eventually led a small team with zero management experience (don't all managers start managing with zero experience at some point?).

• Government contractor to indie freelancer: After that, I went out on my own as a freelancer, even though I knew nothing about running my own business.

• Indie freelancer owner to senior unicorn tender: Today, I work for a unicorn that requires a pristine design that I can only deliver by being at the absolute top of the frontend game, even though I was a 7/10 at best beforehand.

But playing up doesn't come without risk and takes a lot of work. It's only for the ambitious and those who won't have an appetite for keeping work interesting.

How academia has teaching exactly backward

Academia teaches you to build a foundation of knowledge in the basics and build up skills from there. This method isn't effective. How much does what you do in your day-to-day work line up with what you were taught in school? Have you ever studied technology but felt it didn't "click" until you used it in a production-ready app?

Instead of studying for the test, you put yourself at the end. Work backward and leverage those stressors to adapt to your new situation. We are an adaptive species, after all. If you want to be a baker, get in the kitchen.

So THAT’S how Steve got that job in product management

Have you ever worked with someone and thought, "how did they get this job? They don't seem qualified at all!" That could be you! Dream big!

Here's how you can pull it off. But first, some clarification:

What Playing up is and isn’t

Playing up is not overcoming impostor syndrome (but it will help)

Impostor syndrome is a pattern of doubting your talents and abilities. It manifests as an irrational fear of being "found out."  That you shouldn't be where you are. Playing up is knowingly putting yourself in a spot where doubt is rational. Playing up is putting yourself where you deserve to be, eventually.

Impostor syndrome pervades the tech industry. We don't have a formal education and accreditation system like other industries. We don't have a rite of passage to tell us we've made it other than landing a job.

One way to manage impostor syndrome is by talking to your peers about your experiences. Chances are, you have been underrating yourself. You are not an impostor. You are exactly where you need to be.

In fact, playing up can be an antidote to impostor syndrome. You surprise yourself by doing something you thought you couldn't, proving to yourself you are qualified.

Playing up is not "faking it until you make it"

Faking it works for mindsets and perspectives. You can't fake your way into competence that takes deliberate practice. But, you can fake yourself into a position where more competence is required.

Faking it is a strategy that rewires your internal framing. For example, you can fake confidence, optimism, and even happiness, which generates more authentic versions of those feelings. "Faking it" isn't fake at all. Instead, it's a flipping of the script: instead of letting your emotions influence your actions, you are using your efforts to influence your emotions.

Developing skills requires deliberate, consistent, intentional practice.

Get into situations where you aren't quite competent. Then get yourself to that level. Of course, it will require some faking to get there, but that's only the first part of the story.

Watch on YouTube

Why playing up works

One of the fastest ways to level up your skills is by watching masters in action. Playing up allows you to learn from others more skilled than you. You can't get this at home. With online courses, you only see manicured, curated simulacrum of expertise.

When you are on a team, people have a vested interest in your success. Coworkers and bosses will help you.

You also learn more quickly when you play for stakes. Playing for stakes means working in an environment that rewards for success and involves risk if you fail.

Moving up before you are ready lets you move faster.

The downsides

You might lose your job

Worst case, you're fired. This happens when you play up but don't get good. Depending on your skill set, this may not be as catastrophic as you think. If you work in tech, there are plenty of remote job opportunities at various companies. All you have to do to find work is start applying to places besides the ten companies everyone else is applying to.

Honestly, I think that if you don't get fired at least once, you aren't playing the career game aggressively enough.

It requires hard work

You should know going into it that playing up takes work. Playing up is playing on hard mode, with all the benefits and costs. If you are someone who always wants to leave work and work and not think about it outside of 9 to 5, then this strategy isn't for you. Even with on-the-job learning, you'll likely need to invest extra time and resources into skilling up.

Post by Steph Smith (@stephsmithio)

But if this is a challenge you want to take on, how can you get started?

Quickstart guide: playing up

Start by applying for jobs (even if you like the one you have)

The fastest way to get started is to apply for jobs one degree higher than where you are. Job interviews aren't just a way to get hired for a new position. They are a tool you can use strategically for career growth. Don't feel guilty applying for jobs even with no intention of taking them. You can use these to test your mettle for new opportunities.

You probably can't move from a mid-level frontend engineer at an agency to a CTO of a unicorn startup. Instead, think about moving just enough to get uncomfortable in one of these directions:

1. job title

2. job role

3. team size

4. company size

5. project impact

Applying for jobs way outside your comfort zone will not yield results, but I believe in erring towards taking the opportunity.

I often hear people say, "should I apply for this job? I don't know if I'm qualified or not." This mindset is the wrong approach. It's the interviewer's job to decide if you are qualified, not yours. Don't do their job for them.

Good things happen when you get out of your own way.

If you don't get the job, you've received feedback that informs you where to go next. Feedback you can use to refine answers and presentation, and skill set. This feedbacks points to where you have gaps you need to fill. As you learn and improve, confidence will come naturally, making you an even more attractive candidate.

Build a narrative for the opportunity and cover

There's an old joke: How would you describe changing a lightbulb on your resume?

> Single-handedly managed the successful upgrade and deployment of a new environmental illumination system with zero cost overruns and zero safety incidents.

No one is as happy as they seem on Facebook, as pretty as they look on Instagram, or as employed as they act on LinkedIn.

Before you can apply for jobs, you need to be able to tell a narrative about how you belong and why you are asking.

Update your LinkedIn for the job you want, not the job you have. This doesn't mean lying; it means being strategic. Your LinkedIn & resume are a highlight reel, so pick the highlights that position you where you want to be. For example, when I switched from being a full-stack engineer to a frontend engineer, I reworked my work history to focus on accomplishments with JavaScript and less on backend work.

Job postings for jobs you want in the future can act as a roadmap. Look at what skills are required for the positions you want. If you have them, highlight them. If you don't, start getting them.

Take on new projects in your current role

This is the safest way to play up. You can play up towards a promotion or towards learning new skills. As an engineer, you could take on more managerial or strategic projects, examples include:

• Taking on training/mentorship responsibilities

• Contributing to documentation or coding standards that affect the whole team.

• Work with stakeholders to help with product decisions and roadmapping.

The call to adventure

Over time, you will build both confidence and competence. You'll be able to deliver quality work without working many extra hours. You'll have enough knowledge that extra studying is not required. Careers go through narratives, you've slain the beast, and now it's time for a liminal break.

Until you decide to take on your next challenge.

A better model for professional social interaction - Office: The Game

For the rest of this article, imagine office politics through a different lens: Work as a game.

The players have unique viewpoints, hidden information, and personal incentives in this game. They win the game by working together, collaborating, and helping each other achieve those goals.

It is not a win-lose or zero-sum game.

There are many plays where both players benefit. To get pursue your goals, your best bet is to find plays that help both you and others.

Cooperation over the competition.

This office as a game model is not only more fun, but more productive and closer to the truth.

If you want to understand this game model more, look no further than Survivor.

What Survivor can teach us about office politics

Yes, Survivor is still going on CBS. Yes, I still watch it.

Modern survivor is played exclusively by contestants with 20 years of seasons to study. Many people incorrectly assume that Survivor is a game of treachery and deception. But the strategy has evolved. Players today know it’s truly a game about trust and collaboration.

When there is a conflict between two players, one is always eliminated. The tribe keeps the peace. Winners are the player who can get along with the most people for the longest period of time. Working well with others is how you survive the office, survive the rounds of layoffs, and ultimately, survive each other.

Survivor isn’t a game of deception, but it is a cutthroat one.  At the end of every episode, players have to vote someone out. Not so in the office. Hopefully, your organization is growing instead of shrinking. Collaborative play is even more effective under these conditions.

Even if you are being collaborative and honest, is that enough? Is there still something immoral about the game?

3 falsehoods programmers believe about office politics

Office politics require dishonesty

As we’ve established, playing doesn’t require dishonesty. Some people consider any kind of putting on a face or biting your tongue as dishonest or manipulative, but that’s just being professional and civil. You don’t have to lie, and expressing ideas without wearing your heart on your sleeve does not constitute lying.

Some people believe you support a broken system by participating in it. They think the push and pull of differing worldviews and incentives are inefficient, and they would instead focus on the work. This a meme-ably bad take.

Yes, it would be nice if we could all easily agree on what needs to be done, by whom, and why, but that is never the case. You can either learn to be effective with a system (regardless of your opinion), or you can waste energy silently raging against the machine.

Your choice.

You can and should be rewarded for results and results alone

Other people believe that they are disrespecting some kind of a “meritocracy” that should exist. You get ahead from the outcomes of your work, not manipulating people or exploiting loopholes. Sounds good in theory, but it’s only a fantasy.

True meritocracies do not exist in the real world.

The problem with this approach is those true meritocracies cannot exist in the real world. We’ve already talked about people having different perspectives and goals. What we haven’t talked about is previous experience, resources, opportunities, timing, and plain old luck.

In fact, organizations can have a paradox of meritocracy: when trying to install meritocratic practices, they instead tend to discriminate and wind up enforcing racist and sexist hierarchies.

There’s also a paradox at the personal level: More research suggests that when you believe in a meritocracy, you are more likely to act in selfish and entitled ways and think less critically.

The idea that you should play fair because you want the world to be fairer is ludicrous. It’s playing yourself into playing the game sub-optimally.

You have to be ruthless to win

Some people believe that acting selfish and self-entitled is a winning strategy. Steve Jobs is the quintessential archetype. Some people read the Steve Jobs biography and walk away with the thought: “If I was a bigger asshole, maybe I could be more successful like Steve.”

But the research doesn’t bear this out either. People who try to be combative and manipulative are no more likely to acquire power.

The opposite is true. Practicing generosity and gratitude is more likely to lead to success than more negative behaviors. It’s also easier to navigate the world when people don’t mind working with you.

While playing the game aggressively in the sense of attitude is a mistake, there’s still the question of aggressiveness from an energy perspective.

Are you playing passively or aggressively?

You are playing, no matter what. You have to play well with others. Being unable to do so will lead to more stress, getting sidelined from projects, being ignored in meetings, and in worse cases, termination. But you can decide how aggressively (in the gameplay sense, not the attitude sense)  you want to play.

The aggressive strategy isn’t for everyone, and it doesn’t play well in every organization. That’s okay. There’s nothing wrong with sitting back in a comfortable position. But if you’re considering chasing more prestige and opportunity, here are some factors you should consider:

1. Do you work in a growth-friendly environment? Organizations with clear career paths that invest in their employees’ growth are excellent places to employ an aggressive strategy. These tend to be larger companies. Companies with fixed mindsets, slow growth trajectories, and where the COO is the owner’s nephew are less than ideal.

2. Do you want to advance? many developers stop at the senior engineer level and are happy writing code all day. Advancing comes with more money, power, responsibility, travel, and zoom calls. Does that tradeoff appeal to you?

3. Are you ready to be intentional and take ownership of your career? What we are talking about is a mental shift where your career changes from something that happens to you into something you are proactively steering.

If you want to play the game, realize that you can practice and improve. Not everyone realizes this. They’ve internalized the stereotype that engineer types are antisocial. Taking ownership means accepting that you can work on and improve your shortcomings when working with others.

Working with others is a learnable skill

If you’ve decided to invest some skill points in your interpersonal skills, what are some specific places you might look to improve? Here are some options to consider.

1. Managing your emotional state - We can’t control how we feel, but we can control how we express, harness, and process them.

2. Having empathy for others - It’s easy to forget that there are human beings on the other side of software.  Build empathy for coworkers and customers alike.

3. Communicating clearly & honestly - it’s your responsibility to be understood. Learn to speak in a way that people will hear.

4. Being persuasive - Humans are all running the same OS, which is hackable. It’s not enough to communicate information. Information is only helpful if it causes a state change. You need to communicate in a way that gets people to move.

5. Writing - The internet runs on words. Between Slack, email, tickets, and project specs, a large amount of your communication is via writing.

6. Taking initiative - A big part of leveling up in your career is learning to find problems and solutions instead of waiting on someone to tell you what to do.

7. Yes and-ing people - All communication is improv. People will like you better if you can learn to play along with what they are doing and build off of them. Avoid disagreeableness

8. Finding alignment - Observe what games other people are playing. Make your goals fit in with theirs.

9. Compromise & negotiation - Once you find alignment, you must learn how to reach actionable agreements with others that you both feel good about.

these are all things you can practice, cultivate, and develop.

These tasks are part of the work. By playing well with others, you will work on better projects and increase your success rate. coding in silence is suboptimal.

tired of working on features that don't make sense? try getting in the conversation earlier when these decisions are being made, or at least know when and how to push back.

Coding is a solo activity. Building software is a team sport.

Further reading

Some books I highly recommend on improving social interaction.

1. How to Win Friends And Influence People - Dale Carnegie, obviously.

2. Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships 1. Marshall B. Rosenberg, Deepak Chopra - how to communicate without bias, finger-pointing, anger, or defensiveness.

3. Impro: Improvisation and the Theatre - Keith Johnstone - because all conversations are improvisations

4. Radical Candor - Kim Scott - how to be nice and not kind

5. Games People Play - Eric Berne - Understanding what goes on in social interactions.

I’d also recommend this thread about ‘reply game’, and think about how you can apply it to conversations in a professional context.

Post by Visakan Veerasamy ⛵️ (@visakanv)

And some stuff on career strategy:

1. The Gervais Principle - This book teaches organizational literacy via the U.S. version of the Office.

2. Developer Hegemony - This book builds on The Gervais principle and talks career strategy specific to engineers

3. Staff Engineer: Leadership beyond the management track - a tactical guide to having more of an impact within your organization.

4. You and Your Research (transcript) - A fantastic talk on how you have to think about your work holistically if you want to do great work.

Change how work feels every day

Once you view the office as a game and one you can play without guilt, you open many more options for approaching the daily grind.

You can reframe work as somewhere you have agency instead helplessness.

You see organizations as systems. Systems you can learn to work with instead of against in service of your goals.

Instead of seeing weaknesses as fixed properties about yourself, you see opportunities for learning and growth.

Instead of a combative playground for craven sociopaths, you see a community of players helping each other do great work.

When does the next thing happen? – Nick Disabato

Information overload tends to predict structural collapse. Now that social media has reached its conclusion, we must find new ways to socialize that nourish us.

How we got here – RADAR

The current trends have led to misalignment, a lack of synchronicity, impermanence, and atomization. All of this leads us to feel alone and groundless. This article gives us the beginnings of a grammar to talk about the current state and why we are all feeling more “out of sync”:

• Loss - we have fewer cultural touchstones and less connection with one another.

• Misalignment - The way things work is out of line with how we want them to work and how we think they should.

• Impermanence - everything has a 24-shelf life. We spend less time investing in everything from content to friendships. More short-term thinking.

• Atomization - Our perceptions are increasingly made up of algorithmically generated bubbles. It leads to a greater separation of reality itself. When everything is separate, it’s small. And when it’s small, it lacks meaning.

The Muskening - Vanketesh Rao 🔒

A summary of the current orientation of Twitter. While Twitter may not die, Twitter, as we once knew it, is probably gone. Musk bought the platform… as joke? A political move? A tax dodge? It’s hard to say, but none of the outcomes look particularly good. A paid article, so here are a few choice quotes:

• In brief, an irresistible force has met an immovable object. An entrepreneur who has never met a venture he couldn’t master has met a platform that has never met a leader who could tame it. A legendary emperor has marched into a fabled graveyard of empires.

• Among what I think of as the four pillars making Twitter what it is, Discovery, Discourse, Dopamine, and Distribution, the last is the most legible, and most immediately amenable to authoritarian high-modernist redesign for yield. Pay-for-reach is a proposition everybody understands.

• On Blue Checkmarks - Along the way, he managed to antagonize the old bluecheck class, and lend the revamped bluecheck feature a perception that was an unholy cocktail of undesirable attributes: a pay-to-play grifter-marketer badge, a must-display Elon-tribe gang-tattoo, and an adverse selection mechanism for people with LinkedIn-type tastes and sensibilities.

• None of this is novel. Facebook and Google already got to distribution-optimized business models a few years ago. It’s not just Twitter that is headed towards a market-harvesting end-game. The entire industry is already there, and Twitter is just late to this party.

• It’s going to be hard to earn back the goodwill of advertisers who have paused or fled due to the open signaling of new-owner-politics, followed by threats of “thermonuclear” name-and-shame retaliation for supposedly caving to blackmail by nefarious Woke forces (“buy ads or I’ll expose you for being a pedo-guy in the pay of George Soros” would be… an odd marketing tactic to witness).

• And most importantly, it’s going to be hard to earn back the trust of users who are leaving or thinking of leaving because they think the platform is now the instrument of a purely political agenda.

The World Is Run By People No Smarter Than You - Shawn Wang

One positive outcome of the Muskening:

We never have to feel impostor syndrome ever again.

Rates are moving back toward “normal”

We have lived our entire adult life in a bull market. To us, interest rates look like this, a lifetime high:

But over the long term, it looks something like this

Rates are at a local maximum, but are they high? We’ve survived much higher rates before. The US has had positive GDP growth for 42 of the last 50 years. We’ve survived this before, and we’ll survive it again.

Interest rates are rising steadily towards pre-2008 levels. Is this a “new normal” or a “back to normal?”

Either way, it’s the end of one cultural season and the beginning of another.

Fuck around season is over. Find out season is here

Rivers of capital and stonks that only go up carried with them a sense of enduring optimism. As the river dries up, we instead see realism over-optimism, skepticism over idealism, and accountability over impunity.

In the fed rate was lower, would Elizabeth Holmes receive a shorter prison sentence?

A fraud like Theranos can only exist in a low-interest-rate world. The reason people bought into it was that they wanted it to be true. I was sure Elizabeth would get a slap on the wrist: she’s too pretty, too pregnant, too rich, too well connected. No way she suffers consequences for convincing people to mistakenly stop taking their blood thinners and blowing $686.3 million of investor cash.

But now it’s find out season, and she’s getting 11 years.

Post by Bucco Parody Capital (@buccocapital)

While it’s nice to see a huckster get what’s coming to her, the more important impact is how it affects our day-to-day life.

The end of the age of convenience

Imagine how different travel would be without Uber, Lyft, and Airbnb. Soon, you may have to.

Investors are no longer interested in engineering an on-demand economy from scratch.

Without free-flowing capital to deploy, these kinds of businesses can’t continue to subsidize costs.

For example, Doordash. The thing that should not be.

The only way they have stayed afloat has been through venture capital, stealing driver tips, and charging restaurants a 30%. All of this, on top of the exorbitant fees they charge customers

Airbnb started in 2008. Uber was founded in 2009. Lyft followed in 2012. These companies have only existed during the previous economic season, and there is no guarantee they will survive the next.

Like Twitter, these businesses will not truly die but will be husks of their former selves. The beauty of building with cloud computing is that it scales both ways.

But the real question isn’t where VCs are putting the money, it’s where we should put our assets.

It’s never been a better time to hoard

Stocks are cheap, takeout cheeseburgers are expensive, and places to park cash are back on the menu.

I-Bonds became a popular investment vehicle when their rate hit 9%. They are still returning a respectable 6.89% as of this writing.

High-yield savings accounts are back. Ally is currently offering 3%. Now that banks are making money lending to the reserve again, they have incentives to increase deposits and are sharing some of those rates with customers.

Stocks are also on sale. High valuations are dropping. This is another part of the Find out season effect, or as economists call it, “normalization”:

Crypto is on super sale, but it might go to zero.

Typically it takes the market 12 months to react to interest rate changes fully. With more investment options and places to store cash than ever, it makes the most sense to spend as little as possible and invest what you can now.

Besides savings, how can we find opportunities in the new season?

Thriving in the new climate

Work for a business that makes money

harder than it sounds when you’re a software engineer. Approach businesses like you would invest in them. Does their business model make sense? Do they seem stable? Find a company that can weather find out season.

The companies laying off are highly leveraged and not profitable. The fud about engineer hiring is overblown. If you’re looking, here’s a list of 500 companies still hiring.

Become an investment, not an expense

Plenty of companies still have money to deploy, but they are being more thoughtful about where it goes. If you sell products or services, think about how you can position yourself so that companies see you as someone who can save on costs or increase revenue. Many successful businesses are forged in recessions.

Learn to cook

Is it just me, or is eating out getting progressively worse and simultaneously more expensive? Seems like a good time to pick up a copy of The Food Lab and learn to make a nice stew.

Relax

Things are not as dire as they seem. People have weathered worse. There are opportunities here. Finally, remember:

Antifragility: a 30-second primer

Antifragility is any object, person, or process strengthened by stress and disorder. People, systems, and items that break under stress are fragile. The term comes from Nassim Nicholas Taleb's book, Antifragile: Things That Gain from Disorder.

Note that this is different from being resilient; A resilient system doesn't care about stress or disorder one way or another. Antifragile systems crave them.

A common example is the muscular system. You strengthen muscles by putting them under stress.

It’s also a bitchin’ K-Pop song

Watch on YouTube

Need more stress? Have you tried tech interviews?

Interviews start from a place of distrust.

Bad hires are expensive, so companies would rather have false negatives (disqualifying a well-qualified candidate) than false positives (hiring someone ineffective). From the interviewee's perspective, interviews are variant and random.

Evaluating candidates is difficult. As someone with experience on both sides of the table, I know how hard it is to measure someone’s confidence with limited interactions and work samples.

Any interview could consist of one or more exercises:

1. online quizzes

2. pair programming

3. take-home assignments

4. whiteboarding (virtual or in-person)

5. big-picture questions

6. architecture questions

7. behavioral questions

You might have to do hours of unpaid labor before talking to a human. And the human you get might not be thrilled to be proctoring an interview.

Remember: interviewers are developers too

They may not want to be interviewing candidates and would much rather work on whatever feature they have due at the end of their current sprint. They may have yet to spend time practicing their interviewing skills, and their managers may not have invested in helping them grow that skills. Sturgeon’s law is very much in effect.

So, how can you turn this process into a good thing for you?

The Antifragile Interviewing Process

First, you have to start viewing every interview as an opportunity to improve

You may be frustrated that you have to learn skills that seem irrelevant to the job you are trying to get, but that's part of the game. The sooner you can make peace with this, the better.

Think of interviewing skills as an investment in yourself. You are helping yourself get better opportunities.

Once you do this, you can start turning interviewers’ tactics against them.

1. Put in the reps

Clean up your LinkedIn and make sure you’re attractive to recruiters. Make sure your job descriptions contain all the right keywords and include all your best accomplishments. Posting daily seems to increase the number of inbound requests you receive.

You should get plenty of opportunities to talk to people.

If you haven’t interviewed in a while, consider getting a few practice rounds in before applying to jobs where you have more interest.

Interview for jobs you don’t want

One way to get practice is to interview for jobs you are not interested in. You can take the interviews, collect questions, record yourself, reflect, and review.

You may think this is unethical. Aren’t you wasting interviewers' time? Maybe, but interviewers build this into their process. They interview plenty of candidates who have little to no chance of getting hired.

2. Practice coding puzzles

Algorithm riddles you would never see in day-to-day work are more valuable than you think.

They are a waste of time if you view them as a part of your programming repertoire, but not if you view them as part of your career skillset. So what if they have no use outside of the interview process? The interview process is enough. Take note of the questions you see, and study up on common algorithms. Use guides like Cracking the Coding Interview. Protip: more things are graphs than you think.

You’ll want to focus on both the technical and soft skill questions you see, and prep for both.

3. Build your question & answer bank

Take note of questions that you are asked frequently or ones where you trip up. After an interview, take some time to write out answers. Refrain from showing up to an interview and reading from a script, but the act of writing will help you think through your answers and do better next time.

If you prepare, interviewers will only get to hear your first draft. First drafts aren't representative of your best work.

Treat interviews as a feedback loop. If you fail at certain points, that's a signal of a weakness you can work upon.

Here are some facts about yourself you should have down cold for interviews:

1. Your favorite project you’ve worked on, and why.

2. Your toughest technical challenges, and you how you tackled them.

3. A time you had a conflict at work, and how you resolved it.

4. Your approach to testing and documentation

5. How you evaluate new technologies

6. What you do with vague requirements.

If you’re brave, record yourself

Hear me out: record your job interviews and watch them back.

I wouldn't tell the interviewer you are doing this, and I wouldn't share it with anyone else. An interviewer may not take kindly to you sharing their questions.  Watch it yourself and see how you come across it. I know it's uncomfortable, but if you can get used to it, you can get some insight into how you come across to others.

It’s awkward, but the rewards are worth it.

4. Embrace rejection

You’ll deal with rejection during your interviewing process.

Interviewing is a numbers game, and that makes it inevitable. Sometimes it won't be your fault. Realizing this is the first step to making peace with it. You’ll need to be able to handle rejections to bounce back, put on a smile, and jump back into your next interview.

We can’t change the interview process, the sooner we make peace with it, the better.

Embrace the interview, let it strengthen you

You could think of interviews like gym sessions: painful at the moment, but they make you stronger. Or think of it like iterative software development; You tested your interview system, digested feedback, added features, and fixed bugs.

As an additional benefit, you'll be more confident and at ease in your interviews when you're less stressed. That makes you a more attractive hire.

To summarize, the antifragile interview process:

1. Put in the reps

2. Practice coding puzzles

3. Build your question & answer bank

4. Embrace rejection

5. Repeat as needed.

How exactly is Elon “killing Twitter?”

Internet hyperbole aside, here’s what’s been going on at the bird site:

• Igniting advertiser goodwill. Elon showing an unstable public roadmap, as well as accusing advertisers of leaving as a political act, is burning goodwill. This means a loss of revenue for the company.

• Burning poster goodwill. Some people won’t want to be part of the richest man in the world’s political play. He told people to vote republican. He ran a poll asking if he should reinstate trump, so he can ask like his hands are clean after doing so.

• Losing 83.5% of the engineering staff. Can Twitter handle the world cup on a skeleton crew? that remains to be seen.

Post by Mosquito Capital (@MosquitoCapital)

Twitter may not “die,” but do websites of a certain scale ever truly die? technically, Myspace and Digg are still around, withered husks of their former selves.

While the Musk midlife crisis has made for great popcorn internet, there’s been a slow death of social media over the last four years.

What did social media get us, why did it stop, and where do we go from here?

The jobs to be done of social media

What is it we want from social media? What do we hope doom scrolling will do for us?

1. Discovery,

2. Discourse,

3. Dopamine, and

4. Distribution.

We can find new ideas and share our own. We enjoy it and talk with our friends about a bit. Discourse is the only difference between media and “social media,” and it’s slowly being phased out.

The death of the feed and the rise of the reel

Twitter and Facebook have decided that your news feed is no longer for discourse. both default to more content from creators and less from your friends.

Twitter may be dying, but Facebook is already dead.

The only reason I keep Facebook is that it's the last tendrils of the meat space in my social media. I have a neighborhood group where I hear about yard sales, and we organize meetups and block parties. We complain about who Airbnbs what.

That's it. Everything else is a useless feed filled with ads for T-shirts that will make my dadbod look less fat.

No friends, only algorithms.

Mark Zuckerberg realizes that the old Facebook is going, which is why he has spent so much money trying to make Metaverse happen that his company is now worth less than Home Depot.

Post by D🌑CFUTURE (@topherflorence)

A new challenger approaches

Tiktok changed the game when it comes to discovery.

They realized they could learn more about you by not looking at what you like but looking at what you reject. Tiktok stares into your soul. They win the dopamine game.

My friends talk about losing hours to TikTok as if that is a normal thing to do.

There’s nothing social about any of these applications anymore. They’ve gone all in on discovery and dopamine. Distribution is available but pay-to-play.

The public square is gone, & we’re better off for it

on default public social media, people can only show heavily-edited, non-offensive versions of themselves.

This context collapse creates a “lowest-common-denominator philosophy of sharing [that] limits users to topics that are safe for all possible readers.”

Instead, we’ll find our connections in more fragmented and cozy spaces.

Why Substack?

I’ve asked myself, what is it I want from social media? Mostly, discourse.

What I like about Twitter is that it is still the best place to have interesting conversations with strangers. I like sharing and hearing new ideas.

Twitter is the real professional social network, not LinkedIn. Like how Instagram is the real dating site, not Tinder.

That's why I switched to Substack. With it's mix of longer-form content, chat, comments, and email replies, it seems to fit what I'm looking for in a social media platform.

No one tool will replace Twitter. Socializing online will be a mix of different mediums, platforms, and communities.

Where do we go now?

• Private communities - Communal Slacks and Discords.

• Group chats - WeChat, GroupMe, Telegram, Signal.

• The Metaverse

• Real-time online hangouts - Zoom calls with friends, Discord voice channels. Watching each other on Twitch.

• New Twitters - Cohost and Mastodon. The old new Twitter Tumblr. I’m bearish because the energy seems more anti-twitter than pro these platforms. Maybe there is alpha in being an early adopter if you want distribution?

Or fuck it, let’s go back to forums.

The scripts that used to work don’t anymore.

The rate of change will only continue to increase. The feeling of disorientation will only get worse. By the time you can write new scripts, they’ll be outdated. The uncertainty and speed at which things move can be better understood through thinking like a state machine:

Thinking in state transitions

In software, there’s a pattern called a State machine: With other data structures, you think about how the data is structured and what you can do with it. With state machines, instead, you write code that handles transitions between the states.

Styling on the web also has transitions. Instead of styling the two different states of an element, you have to write an initial state and then “tweens”: instructions for how to change from one state to another.

Instead of thinking about where you are or where you are going, state transitions are about focusing on the liminal space in between.

I think this could be a useful model moving forward.

How can you cope with [broadly gestures at everything]?

That’s what I aim to explore in this newsletter:

How can people and organizations get better at handling change and uncertainty?

I can’t do it alone

I can only tell my story and the lessons I’ve learned. I hope to talk to others and share what they are seeing. I want these posts to be the start of conversations and a space where we can figure out what the hell is going on together.

Chat will be enabled for this Substack to give people a place to connect.

Here are some topics I’d like to cover…

Planned topics:

• Senior+ development

  • Learning to become a mentor

  • From interview candidate to interviewer

  • Writing about code overwriting code

  • Thinking strategically over productively

• Career strategy

  • Developing long-term career strategy

  • Finding the right-sized companies for your skill set

  • When learning new technologies

  • How to get oriented at a new organization

• The changing world

  • What impact will AI & ML have on the job you have today?

  • How to navigate the Muskening

…unless something changes.