Doing Taxes When You’re Your Own Boss

Published on: Jun 2, 2020fb-roundtwitter-roundemail-round
dollar bill freelancer at the computer

The Story

Whether you bring home the bacon as a freelancer, side hustler or the boss of your own small biz, one thing is for sure: the gov wants a bite.

Even if it’s not that much bacon?

If you made at least $400, you’re probably on the hook for paying taxes. The IRS has an interactive Tax Assistant tool that lays it all out. Just enter some basic info, like whether you’re single or married and how much you’re making, and it’ll tell you if you need to file a return.

How do I keep track?

At the beginning of a new year, you should get a 1099 from any company or person who paid you more than $600 the last 12 months. Use that to do the math. But it’s also smart to keep your own records, so nothing slips through the cracks. If you don’t get a form you were expecting by mid-February, send a reminder.

Okay. Anything else?

Some bad news: on top of your regular income tax, you have to pay a 15.3% “self-employment tax.” That covers Social Security and Medicare taxes that would have come out of your paycheck if you had a 9-to-5.

Oh, and the gov likes it when you estimate how much you’ll owe them and make a few payments a year. And if you underpay, you’ll owe a penalty. Quarterly estimated payments are typically due in mid-April, June, September, and January.

More tax deadlines? Great.

In better news...deductions. You might be able to write off some expenses. Think: business travel costs, career-boosting classes, a new work computer, even some housing costs – like part of your mortgage and utility bills – if you have a home office.

The more deductions you claim, the lower your taxable income and tax bill can be. Just make sure you keep receipts and records in case you get audited. Psst...audit = a gov investigation to confirm you told the truth, the whole truth, and nothing but the truth on your tax documents.


Doing your own work thing can make paying taxes more complicated. But understanding the rules and claiming the deductions you deserve can help you get it right. And keep more of your hard-earned money.

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