Freelancer bookkeeping: client payments and quarterly tax

Worked example: one quarter, thirteen bank lines

The tool ships a synthetic checking statement for April to June 2026: three invoice payments from one client, a payout from a foreign client through Wise, an Upwork release, a coworking membership, software, one flight and two IRS estimated payments.

Counting the IRS debits as an expense would show $11,745.71 of profit and suggest you owe less than you do. The tool leaves those two lines in review for you; filed as owner draws, profit stays at $15,345.71. Over a full year that profit, about $61,383 annualised, comes to roughly $12,356 of federal income tax and self-employment tax on the tool's single-filer worksheet.

What the estimate says to pay next

Running estimate --year 2026 --months 3 --filing single --paid 3600 --as-of 2026-06-16 annualises the quarter, subtracts the standard deduction and a simplified 20% QBI deduction, adds self-employment tax of $8,673.11, and plans on the 90% safe harbour: $3,760.18 on 2026-09-15 and $3,760.18 on 2027-01-15. Give it last year's tax and income (--prior-tax, --prior-agi) and it uses the 100% or 110% safe harbour instead, which is often smaller. It leaves out state tax, credits and itemised deductions.

How to book it

1. Import your bank statement in AI Bookkeeper. Deposits mentioning an invoice, Wise payout, Payoneer or Upwork are suggested as sales; the IRS debits are left in review on purpose, because the same descriptor can be a payroll deposit; file your own estimated payments as owner draws (account 3100) with confirm ID=3100. Every suggestion waits for you to accept it.
2. Check foreign payments. A Wise payout is what landed after conversion; keep the client's invoice for the gross amount and any fee.
3. Run the estimate after each quarter, with your actual payments entered as --paid.
4. State estimated payments are not covered by the rules; book them as owner draws too.

The payee rules were written from remembered statement wording, not real bank exports, so check how your bank prints the IRS line. The page is not accounting or tax advice.

Questions

Are the IRS payments I make each quarter a business expense?

No. A sole proprietor's federal estimated tax is a payment of your own tax, not a cost of the business. Book it as an owner draw (the tool leaves the line for you to file) so profit is not understated. In the worked example, $3,600.00 of IRS payments would turn $15,345.71 of profit into $11,745.71 if counted as an expense. Ask a tax professional how your situation is treated.

How much should I set aside for the next quarterly payment?

The tool's estimate command annualises the profit so far, works out income tax and self-employment tax and spreads the safe-harbour amount over the dates still ahead. For the example it plans $3,760.18 on 2026-09-15 and again on 2027-01-15. It is a worksheet, not tax advice.

Is it free?

Yes. It is open source (MIT), runs in your browser and nothing is uploaded.