Year-end tax checklist for freelancers (December moves)

Year-end tax checklist

Filing season is for recording what happened; December is the last month you can still change it. Answer six questions and this builds the list of moves that only work before the 31st, from timing an invoice to electing a solo 401(k) deferral, and it ticks off in your browser as you go. For the January to April side of the work, use our 1099 tax prep checklist instead.

Your December list

0 / 9 done

Income timing

Send December invoices now, while the client can still pay this year
Chase old receivables: money collected in December lands in this year's income, at this year's rate

Deductions before the 31st

Sweep the year's card and bank statements for business costs you never recorded
Prepay what a cash-basis business legitimately can: January software renewals, insurance, professional dues

Retirement

Consider opening a plan: a solo 401(k) generally has to exist by December 31, though SECURE 2.0 lets a first-year sole proprietor with no employees set one up as late as the filing deadline

Estimated payments

Diary the Q4 payment for January 15, the last installment of this tax year

Books and records

Reconcile the books against every bank and processor statement, not just the ones you remember
Total the mileage log while the trips are still recognisable
Back up receipts and invoices somewhere that survives a dead laptop

Answers and ticks are saved only in this browser (localStorage). No account, no upload.

How the list is built

Six answers toggle blocks of a master December list. The income-timing block flips direction with next year's outlook (accelerate income in a low year, defer it into one), the purchase and investment blocks appear only when you have something to act on, and the payments block escalates from a simple January 15 reminder to a safe-harbor check when you are behind.

Assumptions

Written for US sole proprietors and single-member LLCs on the cash basis, which is where the December timing moves actually work: accrual businesses book income when invoiced, not when paid, so the first block does not apply to them. Deadlines quoted (January 15 for the final estimated payment, January 31 for 1099-NEC) are the standard dates and shift to the next business day when they fall on a weekend. Checked 2026-08-23 against irs.gov; reviewed each January with our other tax constants.

FAQ

Does deferring an invoice to January actually save tax?

Only if next year's rate is genuinely lower, which for most freelancers means an expected income drop, a sabbatical or a switch to salaried work. Otherwise you have moved the same tax twelve months forward and given yourself a cash-flow gap in the process. Our view: defer for a real rate difference, never just to feel better in April.

Is buying equipment in December a good deal?

It is a discount, not a windfall. A $2,000 laptop at a 30% combined marginal rate costs you $1,400 after the deduction, so the purchase only makes sense if you were going to buy the thing anyway. Spending a dollar to save thirty cents is still spending a dollar.

What happens to this list on January 1?

Most of it expires. Income timing, deductible purchases and loss harvesting are done for the year; what carries into January is the paperwork: the Q4 payment on the 15th, 1099-NEC filings by the 31st, and the retirement deposits you already elected. That handover is where our 1099 tax prep checklist picks up.