How to Prepare for Tax Season
Tax season does not have to be stressful. With proper preparation, starting long before April, you can make the process smooth, accurate, and even rewarding (in the form of deductions captured and taxes saved). Here is a step-by-step guide to preparing for tax season, whether you are an individual or a business owner.
Step 1: Keep Your Books Current Year-Round
The single most effective way to prepare for tax season is to keep your books current throughout the year. When your monthly bookkeeping is up to date, tax preparation is simply reading accurate, organized financials, not reconstructing twelve months of transactions from shoeboxes and bank statements. Businesses with current books file earlier, capture more deductions, and avoid the stress of last-minute preparation.
Step 2: Organize Your Documents in January
Tax documents start arriving in January. Create a dedicated folder, physical or digital, and file each document as it arrives. For individuals, this includes W-2s (by January 31), 1099s (by January 31), investment statements (1099-DIV, 1099-B, 1099-INT), mortgage interest (Form 1098), property tax records, charitable contribution receipts, and records of any other income or deductions.
For businesses, this includes your profit and loss statement, balance sheet, general ledger, payroll records (W-2s and 1099s issued), asset purchase records, depreciation schedule, and prior year return. If your books are current, most of these are already organized in QuickBooks.
Step 3: Review for Missing Deductions
Before handing your documents to your CPA, review the year for deductions you may have missed. Did you track all your business mileage? Did you record home office expenses? Did you capture all business meals and travel? Did you make retirement contributions? Did you purchase equipment that qualifies for Section 179? Our top tax deductions guide covers the most valuable ones.
Step 4: Verify Your Entity Structure
If you are a sole proprietor or single-member LLC and your profit exceeded $60,000-$80,000, ask your CPA whether an S corp election would save you money. If you started a new business, verify that your entity structure is optimal. Entity changes need to be planned before year-end, but reviewing during tax season ensures you are ready to act. Learn more about LLC tax preparation and S corp tax preparation.
Step 5: Review Your Quarterly Payments
If you made quarterly estimated tax payments, verify that they were applied correctly and review whether the amounts were sufficient. If you underpaid, your CPA can calculate the underpayment penalty and advise on whether increasing your final payment would help. Read our guide on quarterly tax payments.
Step 6: Meet with Your CPA Early
Schedule your tax preparation meeting in February or early March, not April. Meeting early gives your CPA time to review your documents, identify deductions, ask questions, and prepare an accurate return without the pressure of a looming deadline. It also leaves time to file an extension if needed, though with proper preparation, extensions should be unnecessary.
If you have been working with your CPA throughout the year for tax planning and monthly bookkeeping, this meeting is a formality, your CPA already knows your situation and has been preparing for your return all year.
Step 7: File and Plan Ahead
Once your return is filed, the most important step is planning for next year. Review what went well and what could be improved. Did you scramble for documents? Start organizing earlier. Did you miss deductions? Set up better tracking. Did you owe more than expected? Adjust your quarterly payments. Tax season is also a planning season, the insights from this year's return inform next year's strategy.
We serve individuals and businesses across Wheaton, Naperville, and Glen Ellyn. Contact us to schedule your tax preparation meeting and make this tax season the smoothest one yet.