Overcome the Fear of Transitioning to Full Time Freelance
8 min read

Overcome the Fear of Transitioning to Full Time Freelance

Overcome the Fear of Transitioning to Full Time Freelance

Have you considered quitting your job and becoming a freelancer? Has your startup shut down and now you are forced to consider becoming a freelancer to pay rent? Going out on your own is a scary proposition, but the rewards are worth it:

Freelancing means that you have more control over who you work with, the kind of work you do, your schedule, and your income. A recent study shows that 45% of full-time freelancers make more than they would at a full-time job.[1]

Why is it so scary? Most of the education and experience we’ve had is biased towards full-time employment. Becoming successfully self-employed means shifting your mindset and gaining a bunch of new skills. As The E-Myth Revisited says, being a great chef doesn’t qualify you to run a bakery.[2]

If you’ve ever considered freelancing, you’ve probably had some of the following concerns:

  • Do I have the technical skills needed to compete in the market?
  • Will I be able to find clients that are willing to pay for those skills?
  • When I find those clients, how will I price my services?
  • Once I set a price, how do I close the deal?
  • Afterward, how can I ensure that I finish the job without getting screwed?
  • If I do all of that, will I make enough money to live happily?

It’s a lot to take on, and more than I can cover in one sitting. I want to give you a 10-minute overview of how to tackle each of these problems and provide some other resources if you want to dig further.

Building Confidence In Your Skillset

Has someone paid you for your skills previously? That’s all the validation you need that you have a skillset that provides value and that there are people out there willing and able to pay for it. Most likely, this is from a previous job.

If you’re a college student, don’t jump straight into freelancing full-time. Doing side jobs for beer money is fine, and looks good on a resume. Even if you want to be self-employed, I’d recommend getting a full-time job for at least two years, preferably one where you get to interact with customers. Consider it an investment in your future, which unlike college, will pay you while you learn. Working full-time will give you idea of how businesses work, allow you to focus on improving your craft, and build a war chest for future entrepreneurial endeavors (more on that in the money section below).

If you’re still not sure, remember that you will always be growing into your skills, and you can grow into the work. If you have technical chops, and the ability to study and improve said chops, then you’ll be okay.

You’ll always be learning, so even when you are employed, working on a side project to increase your skills is a valuable use of time.

Finding Clients

There are many ways to find clients, but it takes work. Work will not just fall into your lap; you have to hustle.

Some strategies you can implement:

  • Your current employer could be your first client. They are a company that has already paid you for your work; you can’t ask for better customer validation.
  • You can proactively reach out to your network, and let them know you are looking for new opportunities. Don’t ask them directly for work, but ask them if they know anyone who may be interested. The network of people one degree separated from you is huge. Last week I found out my friend’s wife gave dance lessons to the daughter of Korn’s drummer. There is more opportunity than you think.
  • You can directly reach out to other freelancers and agencies. Many of them have work that they aren’t fit for or maybe they are overloaded, but they will be more than happy to hand off work to people that they know and trust. Also, when you have work you can’t do, you will have a network of trusted professionals you can fall back on.
  • You can look online for opportunities, but NOT on Upwork or Freelancer.com These race-to-the-bottom marketplaces are horrible for all parties involved. Instead, stick to the job boards that don’t suck[3]

I covered these strategies and others in more detail in my guide: A Guaranteed Strategy To Get Your First Clients[4]

Setting A Price that Works For Both You And The Client

Pricing is an incredibly important and challenging subject that is not talked about very frequently. If you set your price too low, you’ll end up working ungodly hours. Set your price too high and you could find yourself with no clients at all.

If you are put on the spot and asked for a rate, here’s the quickest way to come up with a set rate:

  1. Take your current salary. If you aren’t currently employed, make an educated guess on what you could get today.
  2. Divide by 1,000.
  3. Round a bit if need be and in your favor. If this formula gives you $71.5, then call it $75.
  4. Then bill that much per hour.

That’ll give you a baseline. Let’s break down a year of matching your current salary:

  • Bill 20 hours/week for 50 weeks.
  • Bill 25 hours/week for 40 weeks.
  • Bill 40 hours/week for 25 weeks.

Don’t all of those sound doable? Now, if you raise that rate 10%, you’ve given yourself a 10% raise. That’s generous by most employer standards, and to most clients, the difference between $50 and $55 is a rounding error, and all of that is with billable time being 50% of a salaried position.

That doesn’t mean it’s all Mai-tais on the beach just yet. That additional time will be used for business development, finding clients, facilitating tasks such as email & invoicing, and giving yourself a buffer if things go wrong. (SPOILERS: Things will go wrong.)

The other question of pricing comes down to hourly billing vs. project billing. While I’m not a fan of hourly billing, [5] I think it’s the safest approach for new freelancers. Project billing is more a 200-level approach. However, if you are moving from a senior level position or feel confident in your ability to set expectations and guidelines, and you are willing to take on the risk, then go for it.

There’s also the option of billing daily, weekly, or even monthly. Brennan Dunn did a fantastic job weighing the pros and cons of each here: The definitive guide to project billing [6]

Pricing is a deep enough subject that myself and others have written whole books on the topic. Here are two places to start if you want to dive deep into pricing:

  • The Freelance Pricing Handbook[6] (entry-level).
  • Breaking the Time Barrier [7] (mid-level).
  • Value-Based Fees [8] (grad-student level).


Turning Interested Prospects into Paying Clients

Once you meet someone, you need a bit of ground work. The key questions you need to answer:

  • Is this someone that I can work with? It doesn’t mean “ideal” client. Especially when starting out, it means that you can finish a project with this person without wanting to stab them.
  • Is this someone that is willing and able to pay me? Watch out for people that don’t seem to value you, “idea people” or “early-stage startups” who may not have money or mom-and-pop businesses where the ROI isn’t going to make sense for them.
  • Can you provide what they want? If someone wants beautiful branding and you are a PHP developer, then it’s a no-go. I said you could learn on the job but within reason.

If so, then you have the beginning of a transaction! But before you do any work, two things that have to happen:

  1. You both sign a contract.
  2. You get a deposit.

Don’t lift a finger until either one of those happen. Ever.


I see this mistake all the time, and it’s horrible. If you take one piece of advice from this, watch Mike Monteiro’s video, “Fuck You, Pay Me”.


Both are required. Any client that won’t do either should be sent away as soon as possible.

Providing Value To Your Customers

Hooray, you did it! Time to start doing the work. It’s important to remember that in the end, your clients are your business. That’s why weeding out problematic people is crucial. Bad clients are cancer that will destroy your business from the inside. Good clients are worth 10x what they pay you.

That means that no matter what, you have to keep your word and deliver on what you promise. Good and clear communication is essential. Do what you say and say what you do. All of this is key to excellent customer service, and great customer service is key to survival.

Note that this doesn’t mean being “nice” in a way that is harmful to your business. Good customer service does not require you to be a doormat to every whim of your client. It doesn’t mean you can’t set boundaries.

Be courteous, professional, and clear; don’t be someone’s bitch.

Another common problem after the project has started: The work is done, and the client doesn’t want to pay.

If this happens, it’s probably too late to do anything about it. If this happens and you didn’t get a signed contract, it’s certainly too late. Cut your losses and move on. Watch “Fuck You Pay Me” again before your next project:

The best ways to prevent this problem is to get as much money up front as you can (100% is ideal), and have terms in the contract for when this happens. Otherwise, stop work, and persistently, but calmly, ask for your money.

Be courteous, professional, and clear: Don’t be an asshole.

Managing Your Money

How can you ensure that you are one of that 45% of freelancers making more than a salaried position, and not one of the presumed 55% that don’t? More importantly, how can you make sure that you always have enough money on hand to not starve?

Running a business takes financial discipline. That fiscal discipline needs to start long before you make the leap into freelancing. Get 3x your monthly expenses in the bank before making the leap, minimum. Six months is preferable. If you are unable to be disciplined enough in your spending and saving, then you aren’t going to be able to run a business.

Your reserves aren’t just a rainy day fund. Cash on hand is foundational to weeding out bad clients. Before, I talked about how bad clients can be left unabated, and can kill your business. If you have bills to pay and don’t have the money to pay them, you will justify working with people that you shouldn’t, or charge less than you should.

You work longer hours with more stressful people for less money, which means less time and less energy to put towards getting out this situation.

Eventually, you’ll either go broke or end up getting a job once again while you dig yourself out of the hole that you dug.

Get a company business account, and pay yourself a regular salary. I cover this strategy in detail in my article How to Survive Feast or Famine Cash Flow[8].

You’ll also want to account for expenses and taxes. Taxes can vary by state, but set aside between 25 – 33% depending on your state and amount of expenses you have. Of course, I’m not an accountant. But you should find one to help you with this. A reliable accountant is one of the best investments you can make in your business.

Putting It All Together

So, once you have an idea of your monthly expenses, tax liability, and payroll for the employee of your business, which is you, you have a solid idea of how much money you need to be bringing in each month. Go back to your pricing and your strategy for finding clients, and make sure you have a plan in place for getting an amount of paying work that can hit these marks without working yourself to death.

So go out there and do great work.


  1. Freelancers Make More Than You Think (and Maybe More Than You) 
  2. The E-Myth Revisited
  3. Alternatives to Upwork
  4. A Guaranteed Strategy To Get Your First Clients
  5. Why You Should Charge Flat Project Rates
  6. The Definitive Guide to Project Billing
  7. The Freelance Pricing Handbook
  8. Breaking The Time Barrier
  9. Value-Based Fees
  10. How to Survive Feast or Famine Cash Flow