Reflections on Earning $100,000 Freelancing in 6 Months

In June, I quit my job and set out on my own. By December, I had earned over $100,000 freelancing. Here are six reflections on the past six months.

December 21, 2020 | 10 minute read

I just passed a big personal milestone: I’ve now earned over $100,000 freelancing since leaving my job in June. Now that I’ve hooked you with the money, here’s the real kicker: I did this while working, on average, 20 hours per week.

While I have earned a lot of money in my six months freelancing “full-time”, getting to this point took almost five years. I’m not trying to brag or boast and I’m not going to sell you a course on how you can achieve the same. Like I said, it took me five years of working really hard to get to this point. And even then, I’m very lucky that I was able to (a) make the switch and (b) still earn a good amount of money during a global pandemic.

So instead what I’d like to offer is a handful of reflections on freelancing full-time.

Set Yourself Up for Success on Monday

Like most people, I used to try and be productive on Monday. You have to “hit the ground running,” and all that, right? Once I had the freedom to take a step back and reflect on the architecture of my week, I realized this is not an effective use of Monday.

Think about it this way: if you’re a runner trying to improve your fastest mile, you don’t go to the track and then try and run as fast as you possibly can for your first lap. If you’re trying to become stronger, you (hopefully) don’t go to the gym and immediately pick up the heaviest weights. You warm up first!

Monday is the warm up day for the week.

So what do my Mondays look like now? The biggest difference is that I don’t try to do billable work. Instead, I try to make sure I’m ready to have a really productive week. Now I typically spend Mondays checking in with clients and I have recurring meetings with most of them. I take some time to review all my current projects and deadlines and schedule out when I’m going to work on what. If you’re interested more in that process, I wrote an article on how I use time blocking.

The point is this: I want to clean off my desk on Monday knowing I’ve got a solid plan for the week and the ability to really focus on my work.

I want to feel warmed up.

Hire an Accountant

Before you start freelancing, I would highly recommend finding a good accountant to help you with your taxes. It’ll be a little expensive and you won’t want to pay for it at first. But you will thank yourself for doing it. I would even go so far as to say that a good accountant on speed dial is a basic requirement for any freelancer.

I am not an accountant, nor am I in any position to be offering financial advice for your specific situation, so hire an account for yourself and check all of this with them. With that said, something a lot of people don’t know when they start freelancing is that you have to pay taxes quarterly in addition to at the end of the year. The fiscal year is broken up in to quarters and each quarter you have to pay the IRS one-fourth of what you estimate you’ll owe in taxes for the year.

You want to work with an accountant to figure out how much you’ll likely owe and to help you file these taxes. There are three or four similar types of filings for self-employed, consultants, freelancers, sole proprietors, sole proprietor LLCs, etc, etc and you want to make sure you file the right forms and pay what you owe.

Taxes in the US are awful. The tax code is incredibly confusing and difficult to navigate and if you get something wrong it can be really expensive to fix. So it’s worth every penny to hire someone who really knows what they’re doing and can help you out.

Put Half Your Income Somewhere Where You Can’t Touch it. And Don’t Touch It.

Half?! That’s so much! What?! I hear you - that was my reaction too when I received this advice.

I got this advice right before I made the jump to freelancing full-time and I cannot tell you how glad I am that I followed it.

One of the two really hard parts of freelancing is managing your money (we’ll get to the second hard part next). It’s tricker than when you’re on a W2 because money comes in waves, as opposed to a study pay check.

So why save half your income?

Going back to your taxes, you have to pay estimated quarterly taxes. You sit down with your accountant, estimate how much you’re going to earn, and then create your filings and pay the IRS based on that.

If your estimate is high and you don’t earn as much as you thought you would, then the IRS gives you some of your money back. If your estimate is low and you earn more than you thought you would, then you also owe the IRS more than you thought you would and that money has to come from somewhere.

So save half your income. Doing so has three really important benefits:

First, as I just mentioned, it will help you avoid any financial surprises during tax season.

Surprise: I earned a lot more than I thought I would in my first year of freelancing full-time. That’s great, but now I owe the IRS a boat load more money. That sucks, but it sucks a lot less than if I hadn’t been saving half my income. If that were the case, I’d have to take out a big loan in order to pay my taxes. No thank you.

Second, saving half your income makes you conservative with money. You just get into the habit of thinking in halves. You send out a $5,000 invoice and automatically think $2,500 for me.

Third, you might get a nice bonus at the end of the year. Saving half your income after you’ve already paid your quarterly estimated taxes means that you may end up with a nice chunk of change left over at the end of the year, even if you end up owing more money to the IRS. It’s like giving yourself a bonus and it feels fucking fantastic. (Excuse me.)

Find Stable Work and Variable Work

Finding work is the second hardest part of freelancing. Many freelancers experience booms and busts, which are difficult to manage financially and even more difficult to manage emotionally.

You might go through a dry spell, where you don’t land a lot of projects. This leads to a bust and you have to be really careful with your money and really careful with your psyche. It’s going to be hard to land more work if you’re demoralized. Then, suddenly, you land four really big projects all at once and now you have to somehow manage all of them.

The trick to solving this is to think of your work in terms of the barbell strategy. If you’re not familiar, the barbell strategy is where you invest in really safe assets and really risky assets and nothing else (hence the term barbell: the weight is at both extremes). As a freelancer, you can think of your work as falling on a similar spectrum in terms of what the payoff might be and how much risk there is in getting it. You can then craft your workload accordingly.

I have some freelance clients that pay me for a set number of hours per week, in perpetuity. I have other clients that pay me based on the project. The regular clients are safe in that I know how much I’ll earn from them and when I’ll get paid. The project-based clients are risky because I have to find them, pitch them, and land them. I earn a lot more from the project-based clients, but the risk and effort are both higher. I could, live off of just my regular clients, which is key: it gives me the freedom to pitch all the variable projects I want without risking financial ruin if I don’t land any of them.

Most freelancers go into this thinking of just variable, project-based work which is effectively the same as investing all your money in really high-risk assets. De-risk your work portfolio!

If you want to find regular work, consider past employers or past clients. You can also reach out through your network to see who works at a company that needs someone for a few extra hours per week. You would be surprised how many companies need more help, but not enough more to justify bringing someone on full-time.

Think Through What You Offer and How

You want to have a very specific idea of what you can offer clients. For me, that means:

  • What kinds of projects I take on
  • How I complete projects (i.e. what technologies I use, how I deploy and manage projects, how I organize deliverables, etc)
  • How I pitch and scope work (how I determine how much time a project will take and how much it will cost)

Having a really clear offer (or offers) will help you land work you’re good at and filter out work that will pull you away from work you’re good at.

Having a clear offer will also save you a lot of time by making your projects more repeatable. For instance, I have a Cookiecutter repo that I use to spin up new dev projects and a script that sets up the development, staging, and production environments. The principle I use here is: every current project should make every future project a little easier, faster, and/or cheaper in some way.

Finally, the most important reason to have a clear offer is that clients generally don’t know exactly what they want or need. They’re not experts in building software. They may come to you and say they need a website with out realizing the variability and complexity that can go into that. Do they need a static site? Drupal, WordPress, or something else entirely? Do they even need a CMS? Having a clear offer helps you sell yourself to clients and helps you both determine if it’s a good fit.

Track Your Time Meticulously

Everything comes back to how you spend your time. Whether you make a boatload of money or whether you burn out completely, it all comes back to how you manage your time. So track your time meticulously.

You may need to do this anyway as some of your clients may want a detailed breakdown of how you spent your time with each invoice. I live in the Washington, D.C. area and this is true for most projects that interact with the federal government in any way. Even if you don’t need to do this, it’s probably the most important metric to track and there are a lot of benefits to doing so.

The first and most immediate benefit is that you’ll get paid for all the work you do. It seems like that would be easy anyway, but I have invoiced a client and just missed a day of work because I wrote it on an index card instead of in the notebook I was using at the time.

The second benefit, which is perhaps equally important, is it will give you a very detailed breakdown of how you’re spending your time which you can review periodically. Feel like you’re spending a lot of time in meetings? Review your time log. Feel like you’re not doing enough billable work? Review your time log.

I use Toggle to track my time and I cannot recommend them enough. They have an app or an integration for everything (iPhone, Android, Chrome, Firefox, Mac, Windows, etc). The interface is easy to use and they make the “tracking your time part” really simple. I spent a few weeks researching and testing out different free and paid time tracking apps and Toggle blew them all out of the water. It honestly wasn’t even close.

Tracking your time ensures you get paid for the work you do. It also helps you see how much you’re working. It’s honestly really nice to look back on a week and see that I worked a lot, which must be why I feel so worn out. Or I feel like I didn’t get a lot of billable work done and when I look back on my week and see I was in a lot of meetings. Or, I did work a lot but not nearly as much as I thought, so I must just be feeling a lot of stress and anxiety about my current projects – Let me manage that.


I have found freelancing full-time both incredibly difficult and incredibly rewarding. While I’m glad I made the switch, and even wish I’d done so sooner, it does require a shift in how you think about your work, time, and money.

I hope these reflections help if you are considering a similar path or if you’ve been freelancing for a while.

If I could throw in one final reflection, one reason I was able to achieve this goal was that I connected with a lot of other freelancers. Two of my biggest projects in 2020 came from other people who work independently. I’m gearing up for a large project early next year where I’ll assemble a team of 2-3 other freelancers I know. Many of these reflections came out of conversations I had with friends who are also freelancing full-time.

So, if you have any questions about freelancing or anything I mentioned in this article then connect with me on Twitter. I’ll be glad to answer any questions or elaborate further on anything in this article.