2026 Small Business Tax Planning Checklist

Go through each section. Check off what you have handled. Any unchecked item is a gap worth addressing before tax season.

Books and Records

Business bank accounts are 100% separate from personal accounts

All transactions are categorized and reconciled through the current month

No personal expenses appear in business accounts (or they are properly coded as owner draws)

Profit and loss report is current and readable

All income is recorded including cash, Venmo, PayPal, Zelle, and check payments

Mileage log is up to date with dates, destinations, and business purpose for every trip

Home office deduction is documented (square footage of dedicated workspace vs. total home)

Business meal receipts include who attended and the business purpose

Equipment and tool purchases over $2,500 have receipts and are listed separately

Software, subscriptions, and professional services used for the business are recorded

Receipts and documentation are stored (digitally is fine) and not just in an email inbox or paper pile

All contractors paid $2,000 or more this year have a W-9 on file

1099-NEC forms are ready to issue by January 31st

If you have employees, payroll tax deposits are current with no outstanding balances

S-Corp owners: your salary is documented and reasonable relative to your revenue

All four quarterly estimated tax payments were made on time this year

Payment amounts were based on actual income, not a guess

You know your safe harbor amount for next year based on this year's tax liability

You know approximately what your net profit will be for the year

Retirement account contribution for the year has been decided (SEP IRA or Solo 401k if applicable)

Any large equipment purchases are planned with depreciation method in mind

You have reviewed whether your entity structure (sole prop, LLC, S-Corp) still makes sense at your current revenue level

You have a CPA or tax professional lined up to file your return before the March/April deadlines

How did you do?

20 of 22 checked: Your books are in good shape. A quick review call is still worth doing.
14 to 19 checked: There are real gaps here that could affect your tax bill. Worth a conversation before year-end.
Under 14: Your books need attention before you hand anything to a CPA. The longer you wait, the more expensive it gets to clean up.

Have gaps? Let's close them before they cost you.

A free Financial Health Check takes about 20 minutes. We go through your setup, find what needs fixing, and give you a clear next step.

Prepared by Remi Matteo · Matteo Bookkeeping LLC · Jacksonville, FL · matteo.finance