WRITING

Who's Afraid of Tax Season?

BY CHELSEA ENNEN • May 2, 2025

Who's Afraid of Tax Season?

The best way for freelancers to handle their taxes is to hire a professional. Any experienced self-employed writer will tell you that a financial expert easily pays for themselves in terms of all the time and money saved. 

But if you’re just starting out on your own, a professional may be outside of your budget. And if you’re considering making the leap to freelancing, it’s a good idea to figure out how your new tax situation will work before the IRS is asking you for that money. 

Handling taxes as a self-employed writer isn’t nearly as scary as it might seem. With a few systems in place, handling taxes can be a very simple process. 

Keep Track of Your Money

It might seem obvious to keep track of the money you make as a self-employed writer. But having a variable income is pretty anxiety inducing, and a very common reaction to financial anxiety is to avoid looking at your finances

If your reluctance to sign in to your bank account is mostly psychological, make sure you have the support of a therapist to address your mental health properly. 

But if you’re building up your freelance client list before leaving your nine-to-five, it’s understandable that you aren’t paying the closest attention to the numbers yet; an extra few hundred dollars here and there might not feel worth opening up a spreadsheet. 

Remember, according to the IRS, if you net $400 from a business, you have to report that income on your taxes. That means if you make roughly $33 a month, yes, you will pay taxes on that income. So even if you’re just starting out, you likely need to track any money coming in. 

When it comes to more complicated situations, suit your tracking methods to your business. If you have to send out invoices, and you deal with clients who are maybe a little slow to pay you, you’ll want to add a little more to your data tracking. A simple color coded system can do nicely, so you can change the status of a payment amount once you have it, and you can see at a glance who owes you money. 

In any case, there’s more to keeping on top of your finances than simply looking at the balance in your checking account every so often. 

Round Up

The amount of taxes you’ll pay as a freelancer is variable. Where do you live? How much do you make? What are your business expenses? The tax rate for freelancers is 15.3 percent, but which number do you apply that percentage to? 

There are a lot of online services to help you calculate how much you need to withhold, but in general it’s best to round that number up a little. An estimation is just that—an estimation. And if it turns out you need to pay a little more than what the calculators thought, then you want to make sure you’re still covered. Then if you have anything left over, you get a tax refund, just like someone who pays traditional taxes. 

It’s not enough to just keep track of the numbers you’re saving for taxes if you don’t actually take that amount out of your account. Move that money into a separate savings account so you can’t accidentally use it, that way you don’t look at your bank account and think you have more spending money than you actually do, and so you can know at a glance the entire amount of what you’ve put away for tax season. 

It’s Not Personal—It’s Business

If you’ve ever spent your spring scrolling through bank statements, wracking your brain to think of anything you’ve possibly spent on your business over the past year, then you know how important it is to separate your business expenses as they come up. 

In years past, a shoebox full of receipts might have done the trick, but in 2025, make it easy on yourself and get a credit card that’s only for business expenses. Given that many writers have relatively minimal month-to-month business expenses, signing that card up for autopay pulled directly from your checking account should be fine. The point is for there to be one place you can go to find all of your business expenses, with nothing personal mixed in. 

Compared to self-employed people who need to buy beauty supplies for doing nails, gas for driving their rideshare car, or travel expenses, writers have relatively low overhead. But if you have a website, if you pay for invoicing software, if you have a coworking space membership or a home office, all of those expenses can go toward lowering your taxable income. 

It Doesn’t Have to Be Hard 

Writers can make a lot of fuss over paying taxes—complaining about organizing your receipts is a great way to start a round of small talk at a writers conference. Writers can feel intimidated by accounting work because it feels like the opposite of what your creative talents can do, but if you apply the same mindset you use to organizing your drafting and editing schedule across multiple clients, you’ll do just fine. 

If you make a plan to organize your finances, take out a share for taxes, and separate your business expenses on the front end, it’ll be easy and fast when the payment due dates come around. 

Chelsea Ennen is a writer living in Brooklyn with her husband and her dog. When not writing or reading, she is a fiber and textile artist who sews, knits, crochets, weaves, and spins.

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