The January Tax Checklist for Small Business Owners and Freelancers
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 Reconcile every business bank and card acc...