October always feels like the quiet month. Summer’s over, the holidays haven’t hit yet, and it’s easy to tell yourself you’ll deal with taxes “after the new year.” I get it — but a few of the moves that actually save you money and stress only work if you make them before December 31. Here are the four I’m walking my own clients through right now.
1. Get ahead of your fourth-quarter estimated payment
If you’re self-employed, a 1099 contractor, or a small business owner who doesn’t have taxes withheld from a paycheck, your fourth and final estimated tax payment for 2026 is due January 15, 2027. That date covers income you earn from September through December, so now is the time to look at how the year actually came in — not how you guessed it would back in April.
A good gut check: the IRS generally won’t charge you an underpayment penalty if, across the year, you’ve paid in the smaller of 90% of what you’ll owe for 2026, or 100% of what you owed for 2025 (110% if your 2025 adjusted gross income was over $150,000, or $75,000 if you’re married filing separately). If a strong fourth quarter means you’re short, we can true that up now with your January payment instead of discovering it at filing time. I walk through this in more detail, with real numbers, in my free 1099 Tax Planning Guide — it’s worth a few minutes if you haven’t grabbed it yet.
2. Start collecting W-9s from your vendors now
If your business paid any contractor, freelancer, or vendor $2,000 or more this year for services (the threshold rose from $600 for payments made in 2026), you’ll likely owe them a Form 1099-NEC — and those are due to both the recipient and the IRS by January 31 (which lands on a Sunday this year, pushing the actual deadline to Monday, February 1, 2027). The single biggest time-sink every January is chasing down a W-9 from someone you paid back in March. Send a quick request now, while people are still checking email regularly, and you’ll thank yourself later. This is especially true for real estate professionals and trucking companies working with a rotating cast of subcontractors and owner-operators.
3. Reconcile your books while the trail is still warm
Q4 is the natural point to catch anything that slipped through the cracks — a business expense that got charged to the wrong card, a deposit that never got categorized, mileage you meant to log in July and never did. Cleaning this up now, rather than all at once in March, means your year-end numbers are actually reliable when we sit down to plan. If your records have drifted this year, my free 1099 Tax Deduction Checklist is a good place to start sorting expenses.
4. Call before December, not after
Almost every tax-saving move — retirement contributions, equipment purchases, entity elections, timing income or expenses — gets harder or disappears entirely once the calendar flips to January. If there’s a decision you’ve been sitting on, Q4 is when it still matters.
Ready to get ahead of your January deadlines? Call (713) 730-9792 or get in touch to set up a Q4 planning call. I work with 1099 professionals, small business owners, real estate professionals, and trucking companies across Houston, Spring, Humble, and Atascocita, and I’d rather help you plan in October than clean up in April.
Sources: IRC 6654(d)(1)(B)-(C) (estimated tax safe harbor); IRC 6041(a) and 6041A, as amended in 2025 ($2,000 reporting threshold for payments made after December 31, 2025); IRS General Instructions for Certain Information Returns (January 31 due date, next business day when it falls on a weekend).
General information current as of October 2026, not advice for your specific situation. Whether any of this applies to you, and what it means for your numbers, depends on facts this article cannot know. Deanna R. Ngueket, CPA, LLC — certified public accountant licensed in the State of Texas.
Related: quarterly taxes for 1099 contractors and no tax on overtime: what actually qualifies.
