January brings tax-season dread for many small business owners, not because the return is difficult, but because they must rebuild a year's financial history in two weeks. They search memory, bank statements, and PDF downloads named things like "Invoice_final_FINAL_v3." The return is simpler. Gathering and sorting records causes the trouble.
Spending three to four hours in November or December can change that. Here is what to handle.
Why November Gives You More Time
December works, but November gives you time to fix missing items. Maybe a bank statement is missing, or you need to send a 1099 to a contractor but never collected a W-9. Find those issues in November and fix them before year-end. Wait until the last week of December, and small delays can run you into deadlines.
Set aside two to three hours in mid-November for an initial review. Reserve another hour in late December for anything that arrived afterward. That is enough.
Documents to Gather
First, confirm that you have the full year's records. For most small businesses, that includes:
- Collect bank statements for all 12 months from every business account. Include checking, savings, and any separate tax reserve account.
- Gather all 12 months of statements for every business credit card. Separate personal and business charges on cards used for both.
- Get statements for business loans, lines of credit, and equipment financing. You need the opening and closing balance plus total interest paid for the year.
- Employee payroll records: wages, payroll taxes withheld and remitted, and bonuses. Your payroll service should have a year-end summary.
- Find receipts for large or unusual costs that bank activity does not explain well, including equipment, professional development, and major one-time business expenses.
1099 and W-2 Checklist
If you paid independent contractors or freelancers, federal law generally says you must send a 1099-NEC to anyone paid $600 or more for services during a calendar year, as long as that person is not a corporation. Recipients must get the form by January 31. It must also be filed with the IRS by January 31 for 1099-NEC forms, though other 1099 types can follow different deadlines.
Issuing a 1099-NEC requires the recipient's legal name, address, and Taxpayer Identification Number (TIN). You should have received those details on a W-9 before, or when, the work began. If contractors paid $600 or more are missing W-9s in your files, use November to request them. Without that information, you cannot prepare an accurate 1099, and an incorrect form can cause additional problems.
Businesses with employees must provide W-2 forms by January 31 too. Your payroll service will usually prepare them, but check the timing and make sure employee addresses are up to date in the payroll system.
Reports to Run Before Year-End
Before December is over, download these reports from your bookkeeping system:
- Year-to-date profit and loss statement: Scan every line for anything unusual. An expense category far above expectations may point to wrongly categorized transactions. Correct those before sending the books to your accountant.
- Balance sheet: Review current asset and current liability balances. Confirm that bank balances agree with your statements. Outstanding AR and AP should match what you actually expect to collect and pay.
- AR aging report: Invoices more than 60 days old at year-end may be uncollectable. Your accountant may need to consider bad debt treatment. Know what remains unpaid before the meeting.
- AP aging report: Record unpaid bills owed at year-end in your books, even when you pay them in January. Accrual-basis businesses include December expenses in December, regardless of payment date. Cash-basis businesses do not, but your accountant needs to know which basis you use.
Questions for Your Accountant
Good preparation makes tax work quicker and less expensive. Consider these questions before you meet:
- Personal vehicle for business? Do you have mileage records?
- Dedicated home office? What were total home costs, including rent or mortgage, utilities, and internet?
- Did you purchase equipment worth more than $2,500 that should be capitalized instead of expensed?
- Did you open or close any business bank accounts during the year?
- Did you lend to or borrow from owners or related parties?
- Did significant personal expenses run through the business and need reclassification?
You do not need complete answers yet. The goal is to flag issues before they become surprises during tax preparation.
Preparation Instead of Panic
The small business owners who enter tax season calmly are usually the ones who kept their books reasonably up to date all year. Not flawlessly, just up to date. Transactions get categorized within a week or two of reaching the bank. Reconciliations happen monthly. Contractor payments are recorded when they go out.
With current books, year-end work takes a few hours of review and filing. With books that are a year behind, it becomes a full reconstruction, costing time, accountant fees, and peace of mind. This is not about judging either situation. Life gets busy, and many owners begin the year with a backlog. The way to reduce January emergencies is to keep records reasonably current throughout the year, rather than attempt a huge catch-up each December.
HiGeorge continuously brings in transactions from your bank accounts and sorts them automatically, so your books do not accumulate a backlog. In November, a year-to-date P&L takes one click to run. The records you need are together, and your contractor list is already on file. Year-end becomes a review instead of a rescue. This guide offers general preparation guidance. Your tax obligations depend on your business structure, state, and circumstances, so work with a CPA or tax preparer when filing.
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