At Toozi, we help freelancers and small business owners manage their back office by text. After thousands of conversations, the same three tax mistakes come up over and over. Here's what they are and how to avoid them.
When you're employed by a company, your employer pays half of your Social Security and Medicare taxes. When you're self-employed, you pay both halves — that's 15.3% on top of your income tax. Most new freelancers don't realize this until they get their first tax bill.
The IRS expects self-employed people to pay taxes four times a year, not once. Miss a deadline, and you'll owe a penalty — even if you pay everything by April 15. The quarterly deadlines (April 15, June 15, September 15, January 15) don't follow a logical pattern, which makes them easy to forget.
The home office deduction, mileage, software subscriptions, professional development — these add up. But most freelancers only think about deductions in March, when it's too late to reconstruct what they spent in June.
All three mistakes share a root cause: freelancers don't have a system that works with their actual workflow. Desktop accounting software assumes you'll sit down and do bookkeeping. You won't. Toozi meets you where you already are — your phone.