Quick answer: Do bookkeeping weekly (log transactions, invoice), monthly (reconcile, review profit, set aside taxes), quarterly (estimated taxes on April 15, June 15, September 15, and January 15), and annually (1099s and W-2s by early February, returns by March or April).
📅 Stay organized year-round + free editable checklist
Running a business is exciting, but keeping up with receipts, invoices, and taxes can get overwhelming. The fix is a predictable rhythm. Here are the bookkeeping deadlines every busy entrepreneur should have on the calendar.
🗓 Weekly
- Log income and expenses (15 minutes, same day each week)
- Save and label receipts
- Send invoices for completed work
Skip the spreadsheet setupBookkeeping Plus does the math: dashboard, profit, and tax set-aside.
See Bookkeeping Plus📆 Monthly
- Reconcile bank and credit card accounts
- Follow up on overdue invoices
- Review profit and top expense categories
- Move a percentage of profit into a tax savings account
- If you have employees, deposit payroll taxes on your required schedule
📊 Quarterly
- Pay estimated taxes: April 15, June 15, September 15, 2026, and January 15, 2027
- File Form 941 if you have employees: April 30, July 31, November 2, 2026, and February 1, 2027
- Review pricing, subscriptions, and spending
- Check whether sales tax filings are due in your state
🎯 Annually
- February 1, 2027: 1099-NECs to contractors paid $2,000 or more in 2026 (up from $600), plus W-2s to employees
- March 15: Partnership and S corporation returns (March 16 in 2026)
- April 15: Individual returns with Schedule C, and C corporation returns
- September 15 / October 15: Extended deadlines
- December: Review the year, make planned purchases, and collect W-9s from contractors before paying them again
🧠 Make the deadlines stick
- Put every date into your calendar with a reminder a week ahead
- Use a checklist you tick off each month
- Keep business and personal money separate so every task takes less time
📥 Grab the free checklist
The free 2026 tax deadlines calendar and the Free Bookkeeping Starter Template turn this list into something you can actually follow. For the step-by-step monthly routine, read Monthly Bookkeeping Routine to Stay Tax-Ready All Year.
Frequently asked questions
At least monthly. A short weekly session for logging transactions plus a monthly reconciliation keeps most freelancers and small businesses tax-ready.
For payments made in 2026, 1099-NECs are due to contractors and the IRS by February 1, 2027, because January 31 falls on a Sunday.
Bank and card statements, receipts, invoices, mileage logs, 1099s you receive, and estimated tax payment confirmations. Keep most records for at least three years after filing.
This article is for educational purposes only and isn’t tax or legal advice. Figures reflect IRS guidance for 2026; check with a qualified tax professional about your situation.
