December is busy enough when you run a business. Add holiday sales, staff schedules and family plans, and year-end paperwork tends to slide into January, right when the filing deadlines hit.
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A little work now makes tax season calmer and gives you a clean start for 2027. Here’s a checklist you can work through over the next six weeks. None of it requires an accounting degree. Several items are worth a conversation with your accountant, and we’ve flagged those.
1. Get your books current
Catch up on bookkeeping through November now, so December is the only month left to close.
- Match your bank and card statements to your books.
- Categorize anything sitting in “uncategorized” or “miscellaneous.”
- Flag personal expenses that slipped onto business accounts, and the other way around.
If you’re months behind, this is the single most valuable thing on the list.
2. Chase what you’re owed
Pull a list of unpaid invoices and follow up on anything past due. A polite reminder in November gets paid faster than one in March. While you’re at it, look at which customers pay slowly and decide whether your 2027 payment terms should change.
3. Collect W-9s now — and know the new 1099 threshold
If you pay independent contractors, there’s a meaningful change this year. Under the One Big Beautiful Bill Act, the reporting threshold for Forms 1099-NEC and 1099-MISC rose from $600 to $2,000 for payments made in 2026. A contractor you paid $1,500 this year may no longer need a 1099. One you paid $2,000 or more still does.
What to do now:
- Request a Form W-9 from every contractor you’ve paid this year who hasn’t sent one. It’s much easier in November than in late January.
- Total payments by contractor so you know who crosses $2,000.
- Ask your accountant how card and payment-app payments are handled, and whether any 2025 payments still need attention.
The deadline to file 1099-NECs and send copies to contractors is normally Jan. 31. In 2027, Jan. 31 falls on a Sunday, so the deadline moves to Monday, Feb. 1. There’s generally no automatic extension for 1099-NEC, so plan for that date.
4. Prepare for W-2s if you have employees
W-2s are also due to employees and the Social Security Administration by the same Feb. 1, 2027 date. The IRS recommends verifying employee names, addresses and Social Security numbers ahead of time. Do it now, before the holiday rush. If someone moved this year, you want the right address on file.
5. Review recurring costs
Print out every subscription, software license and recurring charge your business pays. Cancel what you don’t use. Downgrade what you’ve outgrown. Small monthly charges add up to real money over a year.
6. Count inventory
If you sell products, plan a year-end inventory count. Your accountant needs it, and it’s the best time to spot slow-moving stock you might clear out in a January sale.
7. Book a year-end meeting with your accountant
Schedule it before Dec. 31, while there’s still time to act.
Topics worth raising:
- How the year looks compared to last year
- Timing of any planned equipment or vehicle purchases
- Retirement plan options for you and your employees
- Whether your fourth-quarter estimated tax payment is on track
- Any 2026 tax law changes that affect your business
Your accountant can tell you which of these matter for your situation. The point is to have the conversation in December, not April.
8. Back up and organize your records
Back up your accounting files, and keep receipts, contracts and statements organized in one place. A simple folder for each month, digital or paper, works fine. If a storm or a hard-drive failure hits, you’ll be glad you did.
9. Put Florida’s annual report on your 2027 calendar
Florida LLCs and corporations must file an annual report with the Division of Corporations (Sunbiz) each year. The filing window opens Jan. 1 and closes May 1, and the state charges a $400 late fee for reports filed after May 1. File through the official Sunbiz site. Ignore third-party mailers that look official and charge extra.
10. Plan for 2027 cash flow
Many Sarasota and Manatee businesses ride a seasonal wave: busy from winter through spring, slower in summer. Sketch a simple month-by-month cash-flow plan for 2027:
- When will revenue be strongest, and when will it dip?
- Which big expenses — insurance renewals, tax payments, equipment — land in which months?
- How much cushion do you want before the slow season starts?
Even a rough plan helps you decide when to hire, when to buy inventory and how much to set aside.
Bonus: keep business and personal money separate
If you’re still running business expenses through a personal account, year-end is a good time to change that. It makes every item on this list easier. We’ll cover how to do it in an upcoming post.
The bottom line
You don’t need to do all ten this week. Pick two, get them done, and work through the rest by mid-December. Your January self will thank you.
If you want to talk through year-end cash flow or planning for 2027, Liberty Savings Bank’s business banking team is happy to sit down with you. We’d love to help you plan your next year.
This article is for general information only and is not tax, legal or accounting advice. Talk with a qualified tax professional about your specific situation.
