I was sitting on the floor of my apartment in April of my first year freelancing, staring at TurboTax telling me I owed the IRS $14,000 I did not have. Not "I'd prefer not to spend this" money. I literally did not have it. I had been freelancing for about nine months at that point, cashing checks and spending like I was still getting a W-2 with taxes already pulled out.
That moment rewired my entire understanding of what it means to work for yourself.
The Money Is Not What You Think It Is
My first freelance client paid me $40/hr for a React app. I remember texting a friend about it like I had won something. Forty bucks an hour. That is over 80 grand a year if I bill full-time. I was making about $95k at my salaried job, but $40/hr felt different. It felt like more.
It was not more.
Self-employment tax alone eats about 15% off the top before you even get to income tax. Then there is health insurance, which went from "something my employer handles" to "$480/month for a plan with a deductible so high it barely qualifies as insurance." No 401k match. No paid vacation. No sick days. When I finally did the real math, I was making less per hour than my salaried job.
Nobody told me to do that math before I quit.
You Will Get Screwed on an Invoice
This is not a maybe. This is a when.
I did some work for a small agency early on. Good communication during the project. Friendly people. Delivered everything on time. Sent a $6,800 invoice and then just... nothing. For four months. Emails got vague. "We're processing it." "Accounting is backed up." "Let me check on that."
I had no contract. No late fees clause. No kill fee. Nothing.
I got the money eventually. Took a borderline-aggressive email and some very uncomfortable phone calls. But that experience taught me something that all the freelancing advice blogs skip over: the absence of a contract does not just mean you lack legal protection. It means the client does not take the engagement seriously. A contract is not a legal document. It is a psychological one. It tells the client "this person runs a real business" instead of "this person will probably let it slide."
Get a contract. Put late fees in it. Put a kill fee in it. Put a clause that says work stops if payment is 15 days late. I do not care if it feels awkward. Being broke for four months because you were too polite feels worse.
The Freedom Thing Is Real but Weird
Yeah, you can work from anywhere. You can take a Tuesday off. You can work at 2am if that is when your brain decides to cooperate.
But nobody warns you about the guilt.
Every hour you are not working, you are not billing. Every afternoon you spend at the park with your dog, some part of your brain is calculating how much money you just did not make. Salaried workers do not have this problem. They get paid whether they stare at their screen productively or spend 45 minutes in a meeting that should have been a Slack message. Freelancers internalize every unbilled hour as a personal failing.
It took me almost two years to stop feeling guilty about not working on a Saturday. Two years. And I still catch myself doing the math sometimes.
Nobody Prepares You for the Admin Work
I became a freelance developer because I wanted to write code. What I actually spend my time on:
- Writing code: maybe 60%
- Chasing invoices, doing bookkeeping, tracking expenses: 15%
- Writing proposals, scoping projects, handling client communication: 15%
- Figuring out taxes, quarterly estimates, insurance, retirement accounts: 10%
That last 40% is the job nobody tells you about. And if you are bad at it, the 60% does not matter because you will either go broke or burn out managing chaos.
After the $14k tax situation, I built myself a spreadsheet system to track income, set aside tax money automatically, and flag when quarterly payments were due. My accountant actually complimented it, which might be the saddest professional achievement of my life. But it kept me from ever being surprised by a tax bill again.
Most Freelancing Advice Is Terrible
I need to say this because it drove me nuts when I was starting out.
The internet is full of freelancing content that boils down to "charge what you're worth" and "just raise your rates." As if the problem is that freelancers have not considered making more money. Thanks. Revolutionary stuff.
Here is what actually matters and nobody wants to talk about: the first year sucks. You will underprice yourself. You will take bad clients because you need the money. You will say yes to projects you should say no to. You will work weekends not because you are passionate but because you quoted 40 hours and the project is going to take 70.
That is normal. It is not a failure of mindset or hustle or whatever other nonsense the LinkedIn crowd is selling. It is the learning curve of running a business when nobody taught you how to run a business.
The Part Where I Tell You to Do It Anyway
Four years in, I bill at roughly three times what that first client paid me. I pick my clients. I take time off without asking permission. Last month I worked four-day weeks the entire month and nobody noticed or cared.
But I want to be honest: the first 18 months were genuinely hard. Not "character building" hard in the way people romanticize. Hard in the "I might need to go get a real job again" way. The tax disaster. The unpaid invoice. A month where I had zero clients and zero income and started refreshing LinkedIn job listings out of panic.
Would I do it again? Every time. But I would do it differently. I would start with a contract template, a real accounting system, and six months of savings instead of three. I would charge more from day one even if it meant fewer clients. I would set aside 30% of every payment for taxes before I touched a cent of it.
Most importantly, I would stop reading advice from people who have been freelancing for six months and already have a course about it.
I put together a Freelance Developer Business Kit a while back. It started as the spreadsheet system I built after the IRS situation and grew into contract templates, rate calculators, and the quarterly tax workflow I actually use. I go back and forth on whether to even mention it in posts like this, but it would have saved me a lot of pain in year one and I figure someone reading this is about to make the same mistakes I did.
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