It happens every December. The books are mostly done. The year feels decided. And somewhere between holiday parties, family travel, and end-of-year exhaustion, taxes become something to “deal with later.”
That assumption is one of the most expensive beliefs I see every year.
Here’s the truth most business owners don’t realize. December is not too late for tax planning. In many cases, it’s exactly when it matters most. And NO, this doesn’t require spreadsheets, panic buying, or turning your holidays into a finance boot camp. The smartest year-end tax moves are often decisions, not paperwork. Thoughtful adjustments, not frantic activity.
Why December Is Not “Too Late”
The IRS doesn’t shut down for the holidays. The tax code doesn’t either.
Most people associate tax planning with January through September. That’s fine. But many of the levers that move your tax bill don’t lock until December 31st.
Income timing. Compensation decisions. Investment elections. Retirement strategy. Entity optimization. These are not “early-year only” tools. They’re calendar-based tools.
I’ve had countless conversations that start with, “Chris, it’s probably too late, but…” and end with, “I didn’t realize we still had that much control.”
That gap between assumption and reality is where planning lives. Tax planning isn’t about starting early. It’s about knowing what still counts.
The Eggnog-Friendly Tax Moves That Still Matter
This is where people expect complexity and are usually surprised by how simple the conversation actually is.
Real tax planning at year-end doesn’t mean rewriting your entire business structure or implementing ten strategies at once. It means understanding a few key decisions that still have outsized impact.
First: Income Awareness. Not what you earned in theory, but what actually hits this tax year versus next. Timing matters more than most people think, especially for business owners with flexible billing, variable revenue, or discretionary income control.
Second: Owner Compensation decisions. For S-Corp owners in particular, how and when you pay yourself at year-end affects payroll taxes, income taxes, and audit exposure. This isn’t about pushing boundaries. It’s about aligning compensation with reality before the year closes.
Third: Investment Timing. Certain investments create immediate tax impact even if the economic return plays out over time. Others do not. Buying something “just for the write-off” is not strategy. Choosing an investment that fits both your tax picture and your long-term plan is.
Fourth, Retirement Leverage. Most people think retirement planning is about “maxing things out.” That’s backward. The real question is how retirement fits into your broader tax strategy this year and next. The decision matters more than the contribution itself.
None of these require panic. None of these require sacrificing the holidays. They require clarity.
What Not to Do in a Holiday Tax Panic
This is where good intentions quietly turn into bad decisions.
Don’t buy assets you don’t need just for a deduction. A bad investment with a write-off is still a bad investment. Don’t let bookkeeping software or a tax prep checklist dictate strategy. Software records history. It doesn’t plan futures.
Don’t assume last year’s approach still works. Tax law changes. Your business changes. What worked before can quietly become inefficient or risky. And don’t extend and hope. Extensions without strategy simply delay the problem. They don’t solve it.
Tax planning is risk management. Panic is the opposite of that.
A Real December Conversation I Have Every Year
Every year, I have some version of the same call.
A business owner had a solid year. Nothing extreme. Good growth. Healthy cash flow. They assumed the outcome was already set and that filing season would determine the rest.
Instead, we spent one calm conversation reviewing timing, compensation, and a single strategic adjustment. No chaos. No miracle promises. Just alignment.
The result wasn’t magic. It was predictable. Fewer surprises. Better positioning. A plan heading into January instead of regret. That’s what good tax planning looks like. Quiet. Intentional. Boring in the best way.
The Calm Truth About Year-End Taxes
If your business is still operating, you still have options. The calendar doesn’t decide your tax bill. Your decisions do.
December isn’t about scrambling. It’s about choosing not to drift into filing season blind. It’s about understanding which levers are still available and pulling the right ones once.
So if you find yourself thinking about taxes while sipping eggnog this season, that’s not a bad thing. That’s awareness. And awareness, handled correctly, is where the real savings begin.
Welcome to the New Age of Accounting. Let’s begin.
P.S. If you found this article helpful, you’ll love my new book S-Corp Mastery: How Smart Business Owners Maximize Tax Savings & Build a Lasting Legacy. It’s now live and available in a sleek, easy-to-read PDF version. Grab your copy here.
Chris is the Managing Partner at Weston Tax Associates, a best-selling author, and a renowned tax strategist. With over 20 years of expertise in tax and corporate finance, he simplifies complex tax concepts into actionable strategies that drive business growth. Originally from Sweden, he now lives in Florida with his wife and two sons.
