Year-end tax planning checklist for freelancers

Summary

Sources: IRS year-end tax tips, Form 1040-ES, Section 179 guidance, state DOR calendars.

Educational only — not tax, legal, or investment advice. Confirm rates, thresholds, and forms with IRS.gov and a licensed CPA or enrolled agent for your facts.

Freelancers without HR departments must run their own year-end tax planning. This checklist covers federal and common state moves before December 31 and into January—adapt to your entity, accounting method, and state.

1. October–November diagnostics

1. Project full-year Schedule C or K-1 profit vs prior year.
2. Compare paid estimated taxes to safe harbor targets (100%/110%).
3. Identify large one-time deductions or income spikes.
4. Schedule CPA meeting with YTD financials.

2. Retirement contributions

Plan	Year-end action
Solo 401(k) deferral	Execute by Dec 31 via payroll
Solo 401(k) employer	Can wait until filing deadline with extension
SEP IRA	Fund by filing deadline
Traditional/Roth IRA	April deadline for prior year

3. Equipment and Section 179

Place qualifying property in service before year-end to elect Section 179 or bonus depreciation (if extended). Document delivery and business-use percentage.

4. Income and expense timing (cash method)

• Defer billing for December work to January if appropriate and legal under your method.
• Prepay deductible expenses (insurance, rent) if cash method and economic substance exists.
• Charitable contributions must be paid by Dec 31 to count for current year itemizers.

5. Entity and election deadlines

• S-Corp Form 2553 for new election (strict deadlines).
• State PTE tax elections (many close months early).
• Evaluate reasonable salary adjustment for S-Corp owners.

6. Estimated tax true-up

Increase Q4 federal and state vouchers if profit exceeded projections. Remember SE tax in the total—not just bracket math on profit.

7. Documentation sweep

1. Reconcile 1099-NEC received to revenue.
2. Complete mileage log gaps.
3. Capture home office measurements and utility totals.
4. Issue 1099-NEC to contractors paid $600+ by January 31.

8. January critical dates (typical)

Item	Timing
Q4 estimated tax	Mid-January
1099-NEC to payees	January 31
W-2 to employees	January 31
HSA/IRA prior-year	Tax filing deadline

9. Lookahead to next year

Adjust monthly set-aside percentage, update safe harbor baseline, renew marketplace coverage with HSA compatibility, and refresh operating agreement tax distribution policy for multi-member LLCs.

10. What not to do

• Buy personal assets and label them business without use.
• Skip payroll tax deposits on S-Corp year-end bonuses.
• Assume internet “hacks” replace CPA review on aggressive positions.

Official sources

• IRS — Small Business & Self-Employed
• IRS — Forms & Publications

Year-end planning reduces April stress and penalty exposure. Treat this checklist as a meeting agenda with your tax advisor—not a solo filing manual.