October 15 is coming: a year of bank statements, organised in a weekend

The extension you filed in April bought six months. Most of it is gone. Between now and October 15 every CPA's inbox will fill with the same message — "here are my statements, can you sort it out?" — and there's a brutal queue behind it. Clients who arrive in early September with organised records get their return filed. Clients who arrive on October 10 with a folder of PDFs get an apology and a late-filing conversation.

The gap between those two clients is a weekend. Here's how to spend it.

Friday evening: inventory, not bookkeeping

Resist the urge to start categorising. Instead, make the list.

Every account that touched the business in 2025. Checking, savings, every credit card, PayPal, Stripe, Square, Venmo if it was used for business, any loan or line of credit. Mixed personal-and-business accounts count too; you'll separate them later.

For each one, which statements you have and which you need. That's January through December 2025 — plus January 2026, because December's card charges and the last payroll often clear in the new year and your CPA will want to see them. Download the missing ones now; banks make the last 12–24 months available online, and older or closed-account statements take a phone call you want to make tonight, not next week. Password-protected PDFs are fine — leave them as they are.

Any income statements you were sent. 1099-NEC and 1099-K forms in particular; the IRS already has copies, and your totals will be matched against them.

Put everything in one folder per account. That's Friday.

Saturday morning: convert everything

You need every statement as a spreadsheet, and you don't want to type them. Convert the PDFs with NoRekey: drop a folder of statements in, get Excel or CSV back, each one verified against the statement's own opening and closing balances so you know the rows are complete before you touch them. Scanned or photographed statements work; so do password-protected ones. A typical year — twelve statements of three or four pages across a couple of accounts — is a hundred pages and a few minutes.

Combine each account's months into one sheet, in date order. Check that December's closing balance on the statement matches the last running balance on your sheet. If the conversions balanced, it will.

Saturday afternoon: categorise into the lines your CPA will use

Schedule C has a fixed set of expense lines, and a sole proprietor's bookkeeping is simplest when it categorises straight into them. Add a column to each sheet and tag every row with one of:

• Advertising
• Car and truck — actual costs, or keep a mileage log and let your CPA choose the method
• Commissions and fees — payment-processor and marketplace fees live here
• Contract labor — anyone you paid who should have received a 1099-NEC
• Insurance
• Interest — business loans and cards
• Legal and professional services — including last year's tax prep
• Office expense
• Rent or lease
• Repairs and maintenance
• Supplies
• Taxes and licenses
• Travel
• Meals — generally 50% deductible; tag them, let the CPA apply the rule
• Utilities — including the business share of phone and internet
• Other — with a one-word note each

And four tags that are not expenses, which catch-up bookkeeping gets wrong more than anything else:

• Transfer — money moving between your own accounts, including card payments from checking. Counting these double-counts every card expense.
• Owner draw — money you took out. Not deductible, not income.
• Loan principal — the interest is an expense; the principal isn't.
• Personal — it happens. Tag it and move on.

Equipment purchases over a few hundred dollars go on their own list rather than into Supplies; whether they're expensed or depreciated is your CPA's call, and they'll want to see them separately.

Work one account at a time, sort by description so the repeated vendors cluster, and tag in bulk. A year of a small business is usually three to five hundred rows; tagged by description, it's two or three hours.

Sunday: reconcile, cross-check, hand off

Reconcile each account end to end. Opening balance on January 1 plus every transaction equals closing balance on December 31. If the individual statements balanced when converted, this is a formality, and it's the formality that lets your CPA trust the rest.

Cross-check income. Sum your deposits tagged as income and compare against the 1099s. Differences are normal (customer payments that never got a 1099, refunds, timing) but you want to know the reason for each one before the IRS asks.

Total by category. A pivot table on the tag column, one per account, then a summary that adds them up. That summary is, give or take, the Schedule C.

Build the handoff pack. For each account: the spreadsheet, the source PDFs, the reconciliation line. One summary sheet of totals. A short list of open questions — "is the laptop an expense or depreciation?", "the $4,000 deposit in March was a loan from my brother" — because the questions you answer now are the ones that don't bounce back in October.

Send it Sunday night. The CPA who receives that pack in early September can file with time to spare; the one who receives a folder of PDFs in October can't.

The same weekend for an S-corp or partnership

If the business files a 1065 or 1120-S, the extended deadline was September 15, not October 15 — if you're reading this after that date, the routine still applies, but call your CPA first. The third-quarter estimated payment for individuals is also due September 15, and having the year's actual numbers in hand makes that estimate considerably less of a guess.

None of this is tax advice; it's the bookkeeping that makes tax advice possible. Start Friday. The statements are the slow part, and converting them is no longer slow.