The January Tax Checklist for Small Business Owners and Freelancers

January tax checklist for small business owners and freelancers by Robert Allen Bautista, Kansas City tax preparer

January is the busiest month of the tax year for small business owners, and most of it has nothing to do with filing your own return. Several deadlines land before February 1. Here is the checklist I give clients, in date order.

By January 15

  • Fourth-quarter estimated tax payment (Form 1040-ES) for the prior year, if you are self-employed or have other income without withholding.

By January 31

  • Form 1099-NEC to each contractor you paid at or above the reporting threshold for services, and filed with the IRS. (Check 1099 Changes for 2026: the threshold changes for payments made after 2025.)
  • W-2s to employees and Form W-3 with copies to the Social Security Administration.
  • Form 941 for the fourth quarter and Form 940 (federal unemployment) for the year, if you have employees.
  • State withholding reconciliations and city filings where required, such as Kansas City, Missouri earnings tax returns for employers.

During January: close out the books

  1. Reconcile every business bank and card account through December 31.
  2. Clean up uncategorized transactions and personal charges.
  3. Total your mileage log for the year.
  4. List equipment and other assets bought during the year, with dates and costs.
  5. Run a year-end profit and loss and balance sheet.

Gather your personal documents

  • W-2s, 1099s (NEC, MISC, K, INT, DIV, B, R), 1098 mortgage interest, 1098-T tuition, 1095 health coverage
  • Records of estimated payments made during the year (dates and amounts)
  • Retirement contributions, including any SEP or Solo 401(k) contributions you plan to make before filing
  • Charitable donation receipts and childcare provider information

Plan for the year ahead

  • Set this year's estimated payment amounts and calendar the four due dates.
  • Collect W-9s from any new contractors before their first payment.
  • Decide whether an S corporation election makes sense this year; Form 2553 is generally due by about March 15. See LLC vs. S Corp.

Official IRS sources

This article is general information, not tax advice for your specific situation. Deadlines that fall on a weekend or holiday move to the next business day.

Related guides

About the author

Robert Allen Bautista is a tax preparer and accountant in Kansas City. He spent four years at PwC in IT audit and tax, served as Chief Accountant at a CPA firm, holds an M.S. in Accounting, and is a CPA candidate. He has worked with 350-plus individual and small business clients and writes plain-English tax guides in English and Spanish. More about Robert · Website · LinkedIn 

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