Free tool

Year-round tax calendar

Don't react to taxes in March. Here's the full year of deadlines, planning windows, and the moments when you can actually change the outcome.

Educational reference — consult your CPA for specific deadlines.

Planning Calendar

The full tax and planning calendar.

Tax dates aren't random — they follow a rhythm. Here's the full year, with dates you can't miss and planning windows where you can actually move the needle.

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By month

By type

Jan 15

Q4 Estimated Tax Due

Final quarterly estimated tax payment for the previous year.

💡 Pay Q4 estimate

Jan 31

W-2s & 1099s Due

Send W-2s to employees, 1099s to contractors. File with IRS.

💡 Prepare W-2s & 1099s

Feb 15

1099-NEC Deadline

File 1099-NEC reports for non-employee compensation with the IRS.

💡 File 1099-NECs

Mid-March

CPA Planning Call

Meet with CPA to review prior year, discuss income timing, and plan for Q1 estimated tax.

💡 Schedule CPA call

Apr 15

Personal Tax Return Due

Deadline for filing individual 1040 and business returns.

💡 File returns / Pay Q1 estimate

Apr 15

Q1 Estimated Tax Due

First quarterly estimated tax payment for the current year.

💡 Pay Q1 estimate

May–June

H1 Income Review

Review first-half income with CPA. Adjust Q2 estimate if needed. Discuss year-to-date performance.

💡 Schedule mid-year review

Jun 15

Q2 Estimated Tax Due

Second quarterly estimated tax payment.

💡 Pay Q2 estimate

Jul–Aug

S-Comp & Structure Review

If you're an S-corp owner, review W-2 salary. Are you taking too much/too little? Ensure compliance.

💡 Review S-corp salary

Sep 15

Q3 Estimated Tax Due

Third quarterly estimated tax payment.

💡 Pay Q3 estimate

Oct 1

Year-End Tax Planning Starts

Early October: CPA reaches out for year-end planning. This is when the big tax moves happen — accelerate income, defer expenses, max out retirement.

💡 Start year-end planning

Nov

Quarterly Business Review

Review third-quarter performance. Assess if you're on track for estimated Q4 payment and full-year tax liability.

💡 Review Q3 performance

Dec 15

Q4 Estimated Tax Due

Fourth quarterly estimated tax payment (due by the 15th if year-end is Dec 31).

💡 Pay Q4 estimate

Dec 27

Year-End Deadline (S-Corps)

Final deadline to elect S-corp status for the current year (if using late-election relief).

💡 Confirm S-corp status

Dec 31

Tax Year Closes

Last day to make retirement contributions (e.g., Solo 401k, SEP-IRA), charitable donations, and business deductions.

💡 Max out retirement accounts

The pattern

Most business owners only think about taxes in March, when the bill arrives. But the actual decisions that matter happen in October and November — when you can still adjust deductions, max retirement accounts, and set up structures for next year. A proactive CPA reaches out in October, not March. This calendar shows the rhythm; your CPA should be in sync with it.