Tax season—just the phrase makes business owners reach for more coffee. Between receipts scattered across three shoe boxes, mystery expenses you can’t quite remember, and that sinking feeling you forgot something important, April can be brutal.
But here’s the good news: you still have time to make tax season significantly less painful. You don’t need to be a financial wizard or hire an expensive team. You just need to make five strategic moves before you sit down with your CPA or tax software.
1. Reconcile Your Books (Even if They’re a Mess)
Look, we’re not judging. Many business owners are six months behind on bookkeeping. But before you can file taxes, you need to know what actually happened financially last year. Set aside four hours—yes, four full hours—to reconcile your bank statements with your records. Match up deposits, categorize expenses, and find those missing receipts. Your February self will thank your January self.
2. Gather Your Tax Documents in One Place
Create a physical or digital folder labeled “2025 Taxes” and start collecting: all 1099 forms from clients or contractors, 1098 forms if you have a business mortgage, receipts for major purchases or equipment, mileage logs if you use your vehicle for business, and documentation for any home office expenses. Having everything in one spot saves hours of frantic searching later.
3. Review Your Deductions
This is where business owners leave money on the table. Common deductions people forget include: business insurance premiums, professional development and training, software subscriptions, marketing and advertising costs, and merchant processing fees. If you’re not sure what’s deductible, make a list of questionable expenses and ask your tax professional. That’s what they’re there for.
4. Check Your Estimated Tax Payments
If you’re making quarterly estimated payments, verify that you’ve made all four payments for last year. Missing a payment doesn’t just affect your refund—it can trigger penalties and interest. Pull up your records and confirm: April 15, June 15, September 15, and January 15 payments are all accounted for.
5. Schedule Your CPA Appointment NOW
Tax professionals book up fast. If you wait until March, you’ll be squeezed in at the deadline when mistakes are more likely. Book your appointment for late February or early March. Most CPAs appreciate clients who come early with organized documents—and they often have more time to find you additional deductions.
The Real Cost of Procrastination
Rushing through taxes leads to missed deductions, errors that trigger audits, and the stress-induced cost to your health and sanity. Business owners who tackle taxes proactively typically save 10-20 hours compared to those who wait until April 14th.
Bottom Line: Tax season doesn’t have to be chaos. A little preparation now pays dividends in time, money, and peace of mind.
Your Action Step: Pick ONE item from this list and do it today. Just one. Then schedule time for the rest.
Resource: The IRS publishes a Small Business Tax Calendar with all the important deadlines for the year. Bookmark it and set reminders for quarterly estimated payments. Access it here: IRS Small Business Tax Calendar
Need local help? Check out the Delta Chamber member directory for accounting professionals who understand rural Colorado business.