The 2026 Self-Employed
Tax Checklist
Two deadlines are coming fast. This free checklist walks you through Q3 estimated tax (Sep 15), the extension filing deadline (Oct 15), every deduction self-employed people miss, and a 30-minute bookkeeping cleanup you can do today.
Self-employed, 1099, S-corp
Filed a 2025 extension? This is your date.
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What is inside the checklist
- Q3 estimated tax (Sep 15): who owes it, how to calculate using the safe-harbor method, exactly where to pay federal (IRS Direct Pay) and what Florida residents skip.
- Extension filers (Oct 15): the full document list to gather before October, including K-1s, 1099-Ks, and self-employment expense records.
- Deductions self-employed people miss: home office, vehicle mileage, self-employment tax deduction, health insurance, retirement contributions, phone and internet, and more.
- 30-minute bookkeeping cleanup: a step-by-step routine to reconcile your accounts, separate personal and business charges, and stop the mileage log gap before September.
- Referral guide for professionals: if you are an accountant, attorney, or financial planner with clients who need tax help outside your lane, a quick note on how to send them our way.
Want someone to just handle it?
If any of this checklist feels like more than you want to manage, that is exactly what our office is here for. Quarterly estimates, extension returns, bookkeeping cleanup, prior-year and back taxes. A real person, one honest quote, no surprises.