It’s late October, and if you’re like most of the small business owners, 1099 professionals, and real estate and trucking clients I work with, year-end still feels far away, until suddenly it isn’t. I always tell my clients in Houston, Spring, Humble, and Atascocita that the week before Thanksgiving is too late to start getting ready. The next few weeks are the sweet spot: vendors and contractors are still easy to reach, your books aren’t buried under December’s chaos yet, and you have time to fix small problems before they become January fire drills.
Here are the three things I want on your list this week.
1. Know the new 1099 reporting threshold
If your business pays independent contractors, this is the single biggest change for 2026. The threshold for issuing a Form 1099-NEC or 1099-MISC jumped from $600 to $2,000 for payments made after December 31, 2025, under the amendments to IRC Sections 6041 and 6041A. That sounds like good news, since it means fewer forms, but it cuts both ways. Some contractors you issued a 1099 to last year may fall below the new threshold this year, while others you never tracked closely because they were “under $600” might now be closer to $2,000 than you realized. Either way, now is the time to run your vendor payment totals for the year, not December 29th.
2. Collect your W-9s now, while people still answer the phone
This is the step almost everyone puts off, and it’s the one that causes the most January headaches. If you’ve paid a contractor, landscaper, subcontractor, or part-time bookkeeper this year and don’t have a signed Form W-9 on file, request one now. Come January, that same person is juggling their own tax paperwork and is much slower to respond, and you’re the one left unable to file on time or forced to backup withhold. A simple email today saves you a frustrating chase in February.
3. Mark your calendar for the real deadline, not the one you remember
Form 1099-NEC is normally due to your contractors and the IRS by January 31. In 2027, January 31 falls on a Sunday, so the deadline moves to the next business day: Monday, February 1, 2027. It’s a small shift, but if you’re used to treating “the 31st” as a hard deadline, it’s worth updating your reminder. And if you’re a 1099 professional yourself rather than someone issuing the forms, don’t forget your own fourth-quarter estimated tax payment is due January 15, 2027. It’s easy to lose track of in the middle of the holidays.
While you’re at it: clean up the books
Here’s where year-end prep and good bookkeeping overlap. Before your records get handed off for tax season, take an afternoon to reconcile your bank and credit card feeds, clear out any transactions sitting in “ask my accountant,” and double-check that personal and business expenses haven’t gotten mixed together over the last few months. If you want a more detailed walkthrough, I put together a free guide on exactly this, Small Business Bookkeeping Basics, that covers what records to keep and the most common mistakes I see when books aren’t audit-ready.
For my trucking and owner-operator clients specifically: this is also a good moment to make sure your mileage logs and per diem records are current rather than reconstructed from memory in April.
None of this has to happen all at once, and it definitely doesn’t have to happen alone. If you’d rather hand off the vendor review, the W-9 chase, or the books cleanup to someone who does this for a living, that’s exactly what I’m here for.
Ready to get ahead of 1099 and year-end season? Call (713) 730-9792 or reach out through deannacpa.com. I’d love to help you head into the new year with clean books and nothing left to scramble for.
Sources
- IRS: Form 1099-NEC and independent contractors ($2,000 threshold for payments made after December 31, 2025)
- IRS: Instructions for Forms 1099-MISC and 1099-NEC (filing and furnishing due dates)
- IRC Section 7503 (deadlines that fall on a weekend move to the next business day)
- IRC Section 6654 (estimated tax payments)
General information current as of October 2026, not advice for your specific situation. Whether any provision described here applies to you, and what it produces if it does, depends on facts this article cannot know. Deanna R. Ngueket, CPA, LLC, certified public accountant licensed in the State of Texas.
