Quarterly Estimated Taxes for Small Business Owners: Dates and Math

General information, not tax advice. Rules, thresholds, and dates change — confirm with the IRS and your CPA for your situation.

Why estimated taxes exist

Employees have taxes withheld from every paycheck. Business owners don’t — so the IRS requires you to pay as you earn, via quarterly estimated tax payments. These cover both your income tax and your self-employment tax (Social Security + Medicare), which is a big line for the self-employed (entity choice affects this). Skip them and you can owe underpayment penalties even if you pay in full in April.

The quarterly due dates

Federal estimated payments are generally due four times a year — roughly:

• Q1: mid-April
• Q2: mid-June
• Q3: mid-September
• Q4: mid-January (of the following year)

The periods aren’t evenly spaced, and dates shift for weekends/holidays — check the current year’s exact deadlines. Many states have their own estimated payments too.

The math (how much to pay)

You generally want to pay enough to hit a safe harbor and avoid penalties. Common approaches:

• Pay ~90% of this year’s tax, or
• Pay 100% of last year’s tax (a higher percentage applies for higher earners) — often the simplest safe harbor.

Practical method: estimate your annual net profit, apply your expected tax rate (income + ~15.3% SE tax on the applicable portion), divide by four, and pay each quarter. Adjust as the year unfolds if profit runs higher or lower.

How to stay ahead of it

1. Set aside a percentage of every payment received into a separate tax savings account — treat taxes like a bill you pre-fund.
2. Track profit in real time with clean books (chart of accounts).
3. Plan payments around cash flow so a due date never blindsides you (cash flow forecast).
4. Maximize deductions to lower what you owe (deductions).
5. Work with a CPA to dial in the number and avoid penalties.

Predictable revenue makes tax planning easier

Estimating and setting aside taxes is far simpler when your revenue is steady — and reviews drive the consistent lead flow that smooths it out. Tailwind keeps your pipeline full so quarterly payments are a plan, not a scramble — see how it works.

Pay as you go, skip the penalties. See how Tailwind works.