October 15 Is Behind You. Now Stop Treating Taxes Like a Once-a-Year Event.
Taxes aren't an event. They're a result. Here are four money moves to make before December 31 so next year isn't another scramble.
The October 15 extension deadline just passed. For a lot of business owners, that means one thing: relief. The return is in. The stress is over. Time to forget about taxes until next spring.
That's exactly the habit that keeps CEOs overpaying.
Taxes aren't an event. They're a result. By the time you file, every decision that shaped your tax bill has already been made. Strategy happens before December 31. Filing just reports the score.
- Taxes are a result of decisions made during the year, not a once-a-year event.
- Review your profit and loss through September to see where the year will land.
- The fourth-quarter 2026 estimated payment is due January 15, 2027.
- How you pay yourself and when you make big purchases both affect your tax bill.
- Monthly visibility into your numbers turns tax surprises into decisions.
Why the Scramble Keeps Repeating
When taxes only come up once a year, you're always reacting. You find out what you owe after it's too late to change it. You dig for receipts. You guess at what was personal and what was business. And you promise yourself next year will be different.
Next year won't be different unless the process is.
4 Money Moves to Make Before December 31
1. Look at your numbers through September. Pull your profit and loss for the year so far. You can't plan around numbers you haven't looked at. Ask one question: if the next three months look like the last three, where does the year land?
2. Check your estimated payments. If you pay quarterly, the fourth-quarter 2026 payment is due January 15, 2027. Make sure what you've paid so far matches what you're actually earning, not what you earned last year.
3. Review how you pay yourself. Your entity type and how you take money out of the business both affect your tax bill. If you haven't revisited that since you started, it's time.
4. Time your big decisions. Equipment, software, hiring, or a large expense you're already planning? When you make it can matter as much as whether you make it. Talk it through before you spend, not after.
Clarity Is the Strategy
Most CEOs don't have a tax problem. They have a visibility problem. When you see your numbers every month, taxes stop being a surprise and start being a decision.
That's the CEO mindset: you don't wait to find out. You decide.
Your Next Step
Not sure where your business stands going into year-end? Start with the Free CEO Financial Health Check™ and get a clear picture of your numbers before December 31. Want to talk it through? Schedule a free Connection Call.
Frequently asked questions
What should business owners do after the October 15 extension deadline?
Use the time before December 31 to plan. Review your profit and loss through September, check your estimated payments, revisit how you pay yourself, and time any big purchases deliberately.
When is the fourth-quarter 2026 estimated tax payment due?
The fourth-quarter 2026 estimated payment is due January 15, 2027. Make sure your payments reflect what you're earning this year, not last year.
Why is year-round tax planning better than planning at filing time?
By the time you file, the decisions that shaped your tax bill have already been made. Planning during the year lets you change the outcome instead of just reporting it.
Tabitha Lewis, MBA
Founder & CEO of THL Ultimate Solutions in Raleigh, NC. Business & Tax Strategist, TEDx speaker and author of Rise Stronger. Tabitha helps established business owners reduce taxes, increase profits and build long-term business wealth.
More about Tabitha →This article is for general education and is not tax, legal or financial advice for your specific situation.
