Here we go again, somehow the end of the year is right around the corner. One minute you’re sipping pumpkin lattes and listening to holiday music in the grocery store, and the next minute… BAM. It’s time to wrap up your books, gather tax documents, meet payroll deadlines, and try not to sprint into January with your hair on fire.
But here’s the good news: a little preparation right now saves you a whole lot of stress later. And trust me, January-you will be very grateful you handled this before the ball drops.
So let’s check the boxes of the biggest year-end reminders and deadlines every business owner should tackle before 2026 shows up on your doorstep.
1. Track Down Those W-9s
If you pay independent contractors, now’s the time to make sure you have a W-9 from every single one of them. Don’t wait until the second week of January when you’re digging through email threads from six months ago trying to remember whether “Mike from the website project” is a real person or a spam bot.
You’ll need these W-9s to issue 1099s by the January 31 deadline. Missing information equals delays, corrections, and general chaos. Save yourself the headache and gather them now.
Pro tip: if you’re missing a contractor’s W-9, ask before they go on vacation and ignore all emails (you know it’s coming).
2. Get Your Books Clean and Up to Date
If your bookkeeping feels like a junk drawer in December, you’re in good company. But year-end is the perfect time to clean things up. Reconcile your accounts, categorize expenses, clean up old vendor bills, and make sure everything matches what actually happened in your business this year.
Your future tax return depends on accurate numbers. Plus, you’ll start 2026 with clarity instead of confusion, which is always good for business (and blood pressure).
And yes, please categorize things in the right place. Office snacks are not “equipment.” (We see you.)
3. Final Payroll of the Year: Accuracy Matters
Your last payroll of 2025 needs to run by December 31. Everything: wages, deductions, bonuses, reimbursements, and withholding needs to be correct and in the system.
Think of year-end payroll like gift-wrapping the year: a clean, accurate final payroll keeps January simple and keeps the IRS happy.
4. W-2 Prep: Verify Employee Information
Before those W-2s go out, double-check that employee information is up to date:
- Names spelled correctly
- Social Security numbers accurate
- Addresses updated (this one gets missed the most)
- Earnings, deductions, and benefits properly recorded
The goal: No angry emails in February asking why someone’s W-2 was delivered to their old apartment… two states ago.
5. S-Corp Owners: Report Your Health Insurance Premiums
If you’re an S-corp owner, your health insurance premiums must be included in payroll before year-end. Don’t wait until January… the reporting has to hit the books by December 31 so you get the correct tax treatment.
This step can reduce your tax liability, which is basically the adult version of finding $20 in your winter coat pocket.
6. Year-End Bonuses
Giving out bonuses this year? Make sure they’re processed with your final payroll. That keeps everything compliant, accurate, and neatly tied into year-end reporting.
And yes, employees will love you a little extra – never a bad thing.
7. Payroll Deadlines You Can’t Ignore
The big ones:
- December 31: Last day to run 2025 payroll
- January 31: Deadline to issue W-2s
- January 31: Deadline to file W-2s with the Social Security Administration
- January 31: Deadline to issue 1099-NECs to contractors
January 31 is basically “Everything Day.” Circle it. Highlight it. Tattoo it on your desk if needed.
8. Review Year-End Vendor and Subcontractor Payments
Double-check:
- Any uncashed checks
- Outstanding bills
- Whether you paid contractors more than $600 (hello, 1099-NEC)
- Any reimbursable expenses still sitting in someone’s inbox
Cleaning this up now makes tax season smoother and gives you clearer year-end numbers.
9. Review Fixed Asset Purchases and Depreciation Needs
Bought equipment this year? Computers? A new vehicle? Camera equipment for YouTube videos you swear you’re going to film?
Make sure everything is recorded properly so your accountant can apply depreciation correctly on your tax return.
10. Consider Whether You’re Changing Payroll Providers
If you’re thinking about switching payroll systems, year-end is hands-down the best time to do it. January 1 is a clean slate – no mid-year data migration, no messy adjustments, no “Wait, why does this system think we still owe taxes from July?”.
Start the New Year with Intention, Not Overwhelm
The whole point of year-end prep is simple: avoid the January scramble. When you take care of W-9s, clean books, payroll questions, W-2 prep, contractor payments, and final deadlines now, you give yourself the gift of a calm, organized start to 2026.
Your business is smoother. Your tax prep is easier. Your CPA is happier. And honestly, you might even enjoy your holidays a little more knowing everything is under control.
If you’d rather hand off the stress, the cleanup, the deadlines, and the “Wait, where did I put that form?” moments… Harper & Co CPAs Plus is ready to help.
We’ll walk you through every year-end requirement, clean up your finances, help you meet all deadlines, and set you up for a confident start to 2026. Let’s finish the year strong, and start the next one even stronger.
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