Year-End Tax Planning Checklist: 10 Moves to Make Before December 31

Published October 20th, 2026

Every year it happens. December sneaks up, the holidays get busy, and before you know it, it's January and the chance to make smart tax moves for last year is gone.

The good news? Most year-end tax planning is not complicated. It's mostly about getting organized while there's still time to act. Here are ten moves to make before December 31.

1. Get your books current through November

You can't plan with numbers you don't have. Make sure every bank and credit card account is reconciled through at least the end of November. If you're behind, now is the time to catch up, not April.

2. Look at your profit so far

Pull a profit and loss report for January through today. Is this year better or worse than last year? That one number tells you a lot about what your tax bill might look like.

3. Check your estimated tax payments

If you're self-employed, add up what you've paid in estimated taxes this year. The last payment for 2026 is due January 15, 2027. Better to know now if you're short.

4. Think through big purchases

Need a new laptop, trailer or piece of equipment? Buying and placing it in service before December 31 may let you deduct it on this year's return. Just don't buy something you don't need only to save on taxes. Spending a dollar to save 25 cents isn't a win.

5. Gather W-9s from your contractors

If you paid any independent contractor $2,000 or more in 2026, you'll likely need to send them a Form 1099-NEC. The reporting threshold went up from $600 to $2,000 for payments made in 2026. Collect W-9 forms now so you're not chasing people in January.

6. Clean up your receipts

Missing receipts are one of the biggest causes of lost deductions. Snap photos of any paper receipts still sitting in your truck, purse or junk drawer.

7. Review your mileage log

If you use your vehicle for business, make sure your mileage log is complete. The IRS business mileage rate for 2026 changed mid-year, so your log needs dates, not just a year-end total.

8. Separate business and personal

If any personal expenses ran through your business account (or the other way around), flag them now. It's much easier to fix in December than to untangle in March.

9. Plan your year-end payroll

If you have employees, confirm their addresses and Social Security numbers are correct before W-2s go out. W-2s and 1099-NECs are due February 1, 2027, since January 31 falls on a Sunday.

10. Book a year-end review

A 30-minute conversation now can save you hours of stress later. Bring your questions and your numbers, and leave with a plan.

A quick example

Picture a small landscaping business owner who waits until March to look at the year. By then, she finds out she had her best year ever, she skipped her last two estimated payments, and she has a stack of contractor payments with no W-9s on file. Every one of those problems was easy to fix in November. In March, they turn into penalties, late forms and a lot of stress.

Now picture the same owner sitting down for one hour in late October. She sees her profit is up, makes a catch-up estimated payment, sends W-9 requests to her three contractors and schedules a year-end review. Same business, same year, completely different tax season.

Common mistakes to avoid

• Waiting until January to look at the numbers. By then, most of your planning options for 2026 are gone.

• Buying equipment you don't need just for a deduction. A write-off only helps if the purchase helps your business.

• Guessing at estimated taxes. Base your last payment on real numbers from your books, not a hunch.

• Forgetting about contractors. The new $2,000 threshold means fewer 1099s, but you still need records to know who crossed it.

How Piney Woods Books & Tax can help

If your books aren't current, we can catch you up month by month so you have real numbers to plan with. If they are, a year-end review helps you spot what to do before December 31, from estimated payments to 1099 prep. You'll always know the price up front.

Common questions

Is it too late to do year-end tax planning in December?

No. December is busy, but most of the moves on this list can still be made right up to December 31. The earlier you start, the more options you have.

What if my books are months behind?

That's more common than you'd think. Start by getting the most recent months caught up so you can see where you stand, then work backward. Catch-up bookkeeping is built for exactly this.

Do I need a professional for year-end planning?

Not always. If your business is simple, this checklist may be all you need. If your income changed a lot or you're thinking about big purchases, a short review can pay for itself.

The bottom line

Year-end planning isn't about tricks. It's about knowing where you stand while you still have time to make good decisions. Start with clean books, and the rest gets a whole lot easier.

Ready to get organized? Book your free 30-minute consultation with Piney Woods Books & Tax.
Call 240-457-6368, email [email protected] or visit www.pineywoodsbooksandtax.com.

This post is general information, not tax or legal advice for your specific situation. Tax rules change, so talk with a tax professional before making decisions.

Sources

• IRS: Estimated tax payment due dates: https://www.irs.gov/faqs/estimated-tax/individuals/individuals-2

• IRS: Instructions for Forms 1099-MISC and 1099-NEC ($2,000 threshold): https://www.irs.gov/instructions/i1099mec