The Freelancer's Guide to Quarterly Estimated Taxes
If you've ever gotten a surprise tax bill in April — or worse, a penalty notice for underpayment — this is the post that explains why, and what to actually do about it going forward.
Why freelancers pay taxes four times a year
When you work a regular job, your employer withholds taxes from every paycheck automatically. As a freelancer, VA, or consultant, nobody's doing that for you — which means the IRS expects you to estimate and pay your own taxes throughout the year, not just once in April.
That's what "quarterly estimated taxes" means: four payments spread across the year instead of one lump sum. Skip them, and even if you pay everything correctly by April, you can still owe an underpayment penalty for not paying on time throughout the year.
The 2026 due dates
*Following year
Missing one of these doesn't mean you're in trouble immediately — but the penalty clock is running from that date, so the longer you wait, the more it adds up.
What you're actually paying for
Two separate things get bundled into your quarterly payment:
- Self-employment tax — this covers Social Security and Medicare, which an employer would normally split with you. As a freelancer, you're on the hook for the full 15.3% yourself, calculated on 92.35% of your net income (a quirk of how the IRS defines your taxable self-employment earnings).
- Federal income tax — this is the regular progressive tax everyone pays, just calculated on your self-employment income instead of a W-2.
A common mistake is estimating only one of these and being caught off guard by the other. Both need to be accounted for in what you set aside.
A mistake that costs people the most
Estimating tax as a flat percentage of income — "I'll just save 25%" — usually gets it wrong in one of two directions. It's often too high early in the year when you haven't earned much yet, and can end up too low later once your income has climbed into a higher bracket. The real number depends on your total expected income for the entire year, not just what you've made so far.
Set aside money as you get paid, not at tax time
The freelancers who handle this smoothly aren't the ones with the best tax knowledge — they're the ones who move a percentage of every payment into a separate savings account the moment it arrives. By the time a quarterly deadline rolls around, the money's already sitting there waiting, instead of needing to be found.
Get a real number, not a guess
Rather than picking a flat percentage and hoping it's close, run your actual expected income through a calculator that accounts for self-employment tax, the SE-tax deduction, your standard deduction, and real progressive tax brackets — not just a flat guess.