Tax season is only stressful when the books aren't ready. When they are, handing everything to your preparer is a non-event. The difference isn't luck — it's the work you do before the deadline shows up. After more than 24 years preparing financials for audits, boards, funders, and yes, tax preparers, I can tell you the goal is to make tax season boring. Here's how.
One note up front: I'm a Controller and advisor, not a CPA, and this isn't tax advice. Think of everything below as how to get your books into clean, defensible shape so your tax professional can do their job fast and cheap.
Start before you think you need to
The worst version of tax prep is the January-to-April scramble, reconstructing a whole year from memory and a shoebox of receipts. If your books are current all year, prep is mostly review. If they're not, start now — finding a missing 1099 or a mystery transaction is easy in November and miserable on April 14th.
Reconcile every account
This is the foundation, and it's non-negotiable. Every bank account, credit card, and loan — reconciled to the year-end statement, every month of the year. If your QuickBooks balance doesn't tie to your bank statement, your numbers are wrong, and filing on wrong numbers is how you end up amending a return. I don't consider a year "closed" until every account ties to source. If your books aren't reconciled yet, that's step one — and it's the first fix I cover in Common Bookkeeping Mistakes Small Businesses Make.
Clean up your categories
Open your Profit & Loss and actually read it. Look for anything that doesn't belong: a giant "Uncategorized Expense" balance, "Ask My Accountant" items you never resolved, personal charges that slipped in, numbers that look off. Every one of those is a question your preparer would otherwise bill you to ask. Clean them up now, while you still remember what the transactions were.
Chase down the documents
Tax prep runs on paperwork. Get ahead of it:
- 1099s you need to issue. If you paid any contractor or vendor $600 or more, you likely owe them a 1099-NEC — and you need their W-9 on file to do it. Missing W-9s are a classic January headache. Collect them now.
- Income forms you'll receive from clients, processors, and platforms.
- Fixed-asset purchases that may be depreciated — equipment, vehicles, large software or asset buys.
- Loan statements showing year-end balances and interest paid.
- Payroll records if you have employees.
- A mileage log, if you use a vehicle for business — reconstructing this after the fact is painful and weak under scrutiny.
Know the items owners always miss
A handful of areas trip up small business owners every single year. Get these in front of your tax professional rather than guessing:
- Estimated taxes. If you're self-employed, you generally owe quarterly estimated payments if you expect to owe $1,000 or more when you file — and the IRS charges penalties for underpaying, even if you're due a refund at year-end (IRS, Estimated Taxes). Don't let the bill surprise you in April.
- Depreciation. Big equipment purchases usually aren't a simple one-year expense. How they're written off is a tax decision worth making deliberately.
- Home office. If you use part of your home regularly and exclusively for business, there may be a deduction — but the rules are specific. Document the square footage and usage.
- Business mileage. Track it contemporaneously. A clean log is worth real money and holds up; a reconstructed guess doesn't.
- Owner draws vs. payroll. How you pay yourself has real tax consequences and depends on your entity type. Make sure draws, distributions, and owner compensation are recorded correctly — this is one of the most commonly mis-booked items I see.
Separate anything personal
If personal expenses crept into the business accounts, deal with them before you file. Business deductions have to be business expenses. Claiming personal costs is a real audit risk; missing legitimate ones means you overpay. Go through the year and make the line clean.
Tie your opening balances to last year's return
A quick sanity check that catches a surprising number of errors: pull last year's return and confirm this year's opening balances match where you ended — retained earnings, loan balances, asset values. If they don't carry forward correctly, something broke along the way. Better you find it than the IRS.
Hand off a clean package
When you're done, your preparer should get one organized package: reconciled financials, supporting documents, and a written list of your questions and judgment calls. No shoebox, no "I'll send that later." The cleaner the handoff, the faster the filing and the smaller the bill — cleanup time is the most expensive time you can buy from a CPA.
Frequently Asked Questions
When should I start preparing my books for taxes? Ideally you keep them current all year. If not, start by November so you have time to chase missing documents.
Do I need to send 1099s? Generally, for any contractor or vendor you paid $600 or more during the year. You need their W-9 first.
Should I pay quarterly estimated taxes? If you're self-employed and expect to owe $1,000+ at filing, usually yes. Confirm with your tax professional to avoid underpayment penalties.
What's the fastest way to lower my tax-prep bill? Hand your preparer reconciled, clean books. They charge for cleanup time — remove it.
Free download
Get tax-ready faster: the Year-End Tax Prep Checklist (PDF) walks through every step above, and the Contractor 1099 & W-9 Tracker (Excel) keeps your 1099 filings from becoming a January scramble.
If getting your books to clean, ready-to-file shape feels like more than you want to take on, that's exactly what I do. Not sure your books are ready? I'll review them — grab a free 15-minute slot at calendly.com/j-s-murrayllc/free-15-minute-consultation, or reach me at (202) 709-5015 or j.s.murrayllc@gmail.com. Murray & Associates works with small businesses and nonprofits across DC, Maryland, Northern Virginia, and virtually nationwide.
Jason Murray is the founder of Murray & Associates. Over 24+ years he has prepared financials for external auditors, boards, and federal grant funders, and has handled grant draw-downs, monthly and quarterly reporting, and grant close-outs for nonprofit clients.