Year-End Tax Checklist for Freelancers: Do These Before December 31
December isn’t just holiday season — it’s tax optimization season. Every year, I spend one Saturday in early December running through this checklist. It typically saves me $500-2,000 in taxes through strategic timing of expenses, retirement contributions, and end-of-year housekeeping.
Here’s my complete year-end checklist.
The Checklist
Income & Revenue
☐ Review year-to-date income. Run a P&L from your accounting software. Know exactly what you’ve earned. This determines your tax bracket and informs every other decision.
☐ Consider deferring December invoices. If you’re close to a higher tax bracket, sending a December invoice in January pushes that income to next year. I did this once — deferred a $5,000 invoice by 10 days and saved about $300 in taxes.
☐ Accelerate income if this year is lower. If next year looks higher, do the opposite — collect as much as possible before December 31 to fill up lower brackets.
Expenses & Deductions
☐ Accelerate business purchases. Need a new laptop, monitor, or equipment? Buy it in December for this year’s deduction. Section 179 lets you deduct the full cost immediately.
☐ Prepay annual subscriptions. Some software charges annually — pay before December 31 for this year’s deduction.
☐ Stock up on office supplies. That printer ink, paper, and supplies you’ll need in January? Buy them in December.
☐ Book January professional development. Pay for courses or conference registration in December even if the event is in January.
Retirement
☐ Make Solo 401(k) employee contributions by December 31. The employee contribution portion ($23,000 limit in 2026) must be in the account by year-end. Don’t miss this deadline.
☐ Plan SEP IRA contributions. SEP IRA contributions can be made until your filing deadline (April 15 or October 15 with extension), but calculate your target now.
☐ Consider Roth IRA contributions. $7,000 limit, income phase-out starts at $150K MAGI. If you’re close to the phase-out, maximizing before year-end ensures you qualify.
Tax Payments
☐ Review quarterly payment accuracy. Compare total quarterly payments to estimated annual liability. If you’re short, make an extra payment before January 15 (Q4 deadline) to minimize penalties.
☐ Calculate estimated final tax bill. Will you owe in April or get a refund? If you’ll owe a large amount, adjust Q4 payment upward.
Bookkeeping & Records
☐ Categorize all outstanding transactions. Don’t leave uncategorized expenses for January. Review every transaction through November and stay current through December.
☐ Reconcile bank accounts. Make sure your accounting software matches your bank statements. Catch any discrepancies now.
☐ Backup all receipt images. Export annual receipt backup to Google Drive or external storage. Don’t rely solely on your accounting software.
☐ Update asset records. Any equipment purchased this year? Log it with purchase date, cost, and business-use percentage.
Client & Business Admin
☐ Verify client payment info for 1099s. You need to issue 1099-NECs to subcontractors or services you paid $600+. Verify their info now (W-9 forms).
☐ Request W-9s from new vendors. Any new subcontractor or service provider you paid $600+? Get their W-9 before year-end.
☐ Review retainer agreements. Are your retainer rates still appropriate? January is a natural time to adjust.
☐ Plan rate increases for January. Decide on your new year rate and draft notification emails for existing clients.
Planning for Next Year
☐ Set financial goals. Revenue target, savings rate, retirement contribution target, rate increase amount.
☐ Review and adjust your tax savings percentage. Is 28% still accurate? If your income grew significantly, you might need 30%.
☐ Schedule January CPA meeting. If you use a CPA, book your appointment now. January-March is their busy season.
My December Timeline
December 1-5: Run P&L report, review YTD income and tax situation. Identify opportunities.
December 6-15: Make strategic purchases (equipment, prepaid subscriptions). Maximize retirement contributions. Decide on income timing.
December 16-25: Complete all bookkeeping through mid-December. Reconcile accounts. Backup records.
December 26-31: Final purchases, final categorization, final reconciliation. Prepare documents for CPA.
January 1-15: Q4 estimated tax payment. Begin 1099 preparation. Send rate increase notifications.
The Bottom Line
A few hours of year-end tax planning saves hundreds to thousands in taxes. The checklist is straightforward — the value comes from actually doing it before December 31 instead of looking at it in January and realizing you missed the window.
Print this list. Block 3 hours on a Saturday in early December. Run through it. Your April tax bill will thank you.