4 Things You Should Never Do if You’re a Freelancer

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The freelance life can be pretty sweet, but watch out! Keep reading to learn what not to do if you’re your own boss. 

I never intended to become a full-time freelancer, but looking back on the process now, it was perhaps inevitable after I left my museum career and found continued frustrations with a salaried job in a new field. I started freelancing as a means to an end (initially, that end was paying off debt and being able to afford to buy a home), but came to love it so much that I quit my salaried job at the beginning of 2023.

If you’re dipping your toes into the freelance world and wondering if you’ve got what it takes to succeed, here are a few moves NOT to make. Avoiding these pitfalls won’t guarantee a happy freelance existence, but it’ll sure make it easier for you to build one.

1. Neglect your taxes

This first one is major. If you are self-employed, you will owe taxes to Uncle Sam four times a year, in January, April, June, and September. It is imperative that you not forget to make those estimated quarterly tax payments, because if you do, you’ll be penalized. Remember, as a W-2 employee, your employer takes taxes out of your paycheck, but if you’re a freelancer, your clients will not. You’ll receive a 1099 form at the end of the year showing all that you were paid by that client, and the IRS gets a copy of it, too, so don’t think you can pretend you didn’t earn that money and dodge out on the taxes you owe.

I recommend hiring a good accountant to help you calculate how much you’ll owe and prepare your tax return for you, as you get different deductions and write-offs than you would as a salaried employee. And keep track of your business income and costs — I record every bit of money I earn and all my work expenses in a spreadsheet. This makes handling those taxes far easier.

2. Stop growing your skills

When you were a salaried employee, you may have had the opportunity to learn and grow in your career field by way of professional development encouraged and funded by your employer. This was the case for me in museums — I often got to attend workshops, presentations, and industry conferences, and I enjoyed these chances to network and pick up new skills.

If you’re a freelancer, you’ll have these same opportunities, but you’ll have to do more of the legwork. Join groups on social media (such as Facebook and LinkedIn) for your profession or area of expertise. Seek out connections with industry leaders (LinkedIn, again, is great for this), and if you can fit workshops and conferences (virtual or in person) into your schedule, you definitely should.

Staying on top of trends and new knowledge in your field will keep you fresh and employable, and you can more easily market yourself to new clients. Investing in yourself is even more important as a freelancer.

3. Live without cash savings

If you’re preparing to quit your salaried job, one of the best things you can do for yourself first is to make sure you have a solid cushion of cash saved up. Commonly held wisdom for an emergency fund is to save three to six months’ worth of bills, but this is predicated on the idea that you’ll have access to unemployment insurance if you lose your job. As a freelancer, you won’t, so it’s a good idea to have even more in your savings account to get you over the hump if you lose a client and have to drum up more paying work for yourself.

4. Skip taking time off work

This is where I often struggle. As a freelancer, you don’t get paid time off. If you’re not working, you’re not making money. And you might feel as if you can’t ever take time off work as a result.

So what’s the solution? I am now feeling a bit more confident in my ability to not be a workaholic all the time, thanks to recently taking a vacation to another country. I took my laptop with me and worked a little. But the bulk of it was when I was sitting around in airports for several hours at a stretch, or when I got up early in the morning (if you can ever get someone else to make you breakfast while you work, I highly recommend it). The rest of the time, I enjoyed myself and didn’t think about work. I also put in extra hours before I left on my trip, and now that I’m home, I’m getting back into the swing of things.

If you’ve ever sat in yet another endless work meeting and wondered, “Isn’t there a better way?” going freelance might be right for you. Just be sure you’re keeping taxes and professional development in mind, and don’t forget to pad your savings. Oh, and take time off, too — it’s good for you.

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