If you find yourself panic-googling things like “how much should I set aside for taxes small business,” or “payroll tax deposit deadlines 2026” this summer, you aren’t alone. According to a recent study, 37% of small business and gig workers feel anxious and confused about how to file taxes.
Midyear tax anxiety may be common but it doesn’t mean its comfortable. The good news is, Neely’s Accounting is here to help. We’ve supported hundreds of Roanoke-area small businesses with their taxes and payroll since 2007 so we know a thing or two about how to navigate the complex tax system. We’ve put together a checklist of the 6 things you need to do this summer to feel confident about your small business payroll and taxes.
Your Mid-Year Small Business Payroll and Tax Checklist
- Confirm your Q2 estimated tax payment
Self-employed individuals and small business owners pay estimated quarterly taxes and if you don’t pay enough by the due date you may be charged a penalty. The deadline for paying your Q2 estimated taxes was June 16 and covers income earned from April 1 to May 31. - Verify your federal payroll tax deposits are up to date
Your FICA payroll tax deposits are due by the 15th of every month. It’s important to note that the Social Security wage base increased to $184,500 in 2026 so be sure your payroll system reflects this. Ensuring that your deposits are accurate saves you time and stress down the road. - Prepare for Form 941 Q2 filing
The IRS requires every employer with W2 employees on their payroll to file Form 941 payroll tax each quarter that reports income tax withholding and matching payroll taxes. The deadline to file Form 941 Q2 is July 31 so spend a bit of time ensuring your records are accurate. Be sure to note that OBBBA rules on tax-free tips and overtime will affect how you report so be sure you payroll is set up correctly. - Make sure Virginia income tax withholding is up to date
Like federal taxes, Virginia requires employers to withhold state income tax from employee wages and pay this withholding on a regular schedule. Unlike federal taxes, your withholding frequency (monthly, quarterly, or semi-weekly) is based on how much you withhold. Be sure to confirm you’re on the right schedule and that your filings are current. - Review employee classifications
Misclassifying an employee as an independent contractor is a payroll mistake that can result in heavy fines. As you’re organizing your 2026 payroll be sure to keep in mind that the 1099-NEC reporting threshold jumped from $600 to $2,000 in 2026. In other words, if you pay contractors, make sure you know who still needs a form and who doesn’t under the new rules. - Reconcile your books through June 30
Midyear is an ideal time to make sure your books match your bank statements, payroll records, and tax filings. Catching discrepancies now saves significant time and stress at tax time. If your bookkeeping has fallen behind, it’s a great idea to get it caught up now before the second half of the year picks up.
Reliable Payroll & Small Business Tax Support from Local Accountants
We’ve handled taxes and payroll in Roanoke for nearly two decades and freed up bandwidth for countless small business owners to put back in their businesses. If you’re ready to stop your anxiety-fueled, midnight googling about small business taxes and payroll, give us a call today. Our Roanoke CPAs will take care of everything down to the last detail so you enter next tax season with compliance and confidence.