Quarterly Estimated Taxes: The Freelancer's Flight Plan
By Mr. Liad Goren, CPA · 2026-09-15
If you're self-employed, the IRS expects taxes four times a year — not once in April. Here's how to estimate, pay, and stay on course without the panic.
When you leave a W-2 job for freelancing, one of the biggest surprises is that nobody withholds taxes for you anymore. Instead, the IRS expects you to send estimated payments four times a year. Miss them, and you can face underpayment penalties on top of a large bill in April.
Who needs to pay quarterly?
Generally, if you expect to owe $1,000 or more in tax for the year after withholding, you should be making estimated payments. That catches most freelancers, independent contractors, gig workers, and landlords with meaningful rental income.
A simple flight plan
- Start from last year's return. A safe harbor rule lets you pay 100% of last year's tax (110% if your adjusted gross income was over $150,000) to avoid most penalties.
- Set aside 25–30% of every payment you receive into a separate account.
- Recalculate if income swings. Using the annualized income installment method can help if your income is lumpy.
The 2026 due dates
Estimated payments are due in April, June, September, and January of the following year. Missing a quarter by even a few days can trigger a penalty, so calendar them at the start of the year.
Common mistakes we see
Waiting until April and paying everything at once is the most common — and most expensive — mistake. The second is ignoring self-employment tax entirely: beyond income tax, you owe 15.3% in Social Security and Medicare contributions that employees split with their employers.
If this feels overwhelming, that's normal — it's a system designed for employers, not freelancers. A single 30-minute session with a licensed CPA can turn this from a source of anxiety into a checklist you run four times a year.