· 1 min read · Foozool Team
Tax Season Preparation Checklist for Small Businesses
Tax season stress is a symptom, not the disease. The real problem is 11 months of deferred bookkeeping that all comes due at once.
Here’s how to spread the work throughout the year so tax filing becomes a non-event.
Monthly Tasks (All Year)
- Reconcile bank statements within the first week of each month
- Categorize all transactions — don’t leave anything in “Uncategorized”
- File receipts and invoices — digital copies attached to transactions in your accounting software
- Record estimated tax payments (if you pay quarterly)
- Review accounts receivable — follow up on unpaid invoices
If you automate invoice capture with a tool like Foozool, most of the filing and categorization happens automatically.
Quarterly Tasks
- Pay estimated taxes (April 15, June 15, September 15, January 15)
- Review P&L statement — catch anomalies early
- Verify payroll tax deposits are current
- Update mileage and home office logs if applicable
Year-End Tasks (November–December)
- Gather W-9s from all contractors you paid $600+
- Maximize deductions — prepay expenses, contribute to retirement accounts
- Review asset purchases for Section 179 deduction eligibility
- Verify all accounts are reconciled through November
- Back up your accounting data
January Tasks
- Issue 1099s to contractors (due January 31)
- Reconcile December and close the year
- Compile all tax documents — W-2s, 1099s, interest statements, investment reports
- Schedule time with your CPA
The Pattern
Notice the pattern: tax preparation isn’t a January activity. It’s a year-round habit of keeping clean books. If your books are accurate and current, “tax preparation” means exporting a few reports and handing them to your CPA.
The biggest enabler: making sure every invoice and receipt is captured and categorized as it arrives, not discovered in a shoebox in January.