December 31 Is a Wall, Not a Suggestion
Every business owner we know has a version of the same list. The things you're going to get to. Not urgent, not forgotten, just always sitting one week out.
Most of that list is forgiving. It waits for you. This particular list isn't. Everything below has a hard stop at midnight on December 31, and after that it's simply not available to you for 2026, no matter how good your reason is, no matter who your accountant is, no matter how early you file.
So here it is, plainly, while there's still time to do something with it.
Has to happen before December 31
Owner compensation — if you're an S corporation, your wages have to run through an actual payroll before your last check date of the year
Shareholder health insurance — owner coverage has to be reported on the W-2 correctly, which means telling your payroll people before the final payroll, not in February
Equipment and vehicles — placed in service, meaning delivered and available for use, not ordered and not merely paid for
Retirement plan setup — several plan types have to exist by year end even if the money goes in later, and "exists" means paperwork signed, not intended
Employee bonuses — the timing decision, and for many businesses the actual payment
W-9s from every contractor you paid — chase these now, in October, while people still answer the phone, instead of in late January when 1099s are due
Accountable plan reimbursements — mileage, home office, and out-of-pocket costs you've been covering personally all year and never reimbursed yourself for
Charitable contributions, if you're making them
Writing off uncollectible receivables and dead inventory
Entity elections you want in effect for 2027
Can wait until you file
Not everything is a December problem, and we don't want you rushing things that don't need rushing:
Funding certain retirement plan contributions, where the account exists but the deposit can come later
Some individual retirement account contributions
Certain elections that get made on the return itself
Filing an extension, which buys time to file and nothing else
That last line is worth repeating, because it's the single most common misunderstanding we encounter. An extension is not an extension to pay. If you owe, you owe on the original due date, and interest starts there.
The dates to put on your calendar right now
January 15, 2027 — fourth quarter estimated payment for 2026
January 31, 2027 — W-2s and 1099s out the door
March 15, 2027 — S corporation and partnership returns
April 15, 2027 — personal returns, C corporations, and the first estimated payment for 2027
Notice how tightly those last two are stacked. In April you can be making a first-quarter payment for the new year at the same moment you're settling up on the old one. Owners who haven't planned feel that month for a long time afterward.
If you already owe the IRS, your deadline is harder than everyone else's
We want to speak directly to a specific group here, because this affects a real number of the people reading it.
If you're in an installment agreement, an accepted offer in compromise, or currently non-collectible status, staying in compliance is part of the deal. That means filing on time and paying current taxes on time, every year, for the life of the arrangement. Showing up in April with a new balance you can't pay can undo an agreement you spent a long time getting.
We've watched people lose a settled arrangement over a new-year balance they never saw coming, and it is genuinely one of the most preventable bad outcomes in our whole practice. If this is you, you shouldn't be doing a fall projection as a nice idea. You should be doing it as maintenance on something you can't afford to break.
What the other side of this looks like
For the business, it's the absence of a scramble. The last payroll of the year is right the first time. The 1099s go out without a week of chasing tax ID numbers. There is no January discovery that something needed to happen in December.
For you, it's a normal spring. You get a return that confirms what you already knew, rather than a number that reorganizes your year. You get to spend February thinking about your business instead of about your taxes. And if you owe, it's already funded, because you've known about it since October.
That's really all any of this is for. Not a magic trick and not a loophole. Just knowing sooner, so that what arrives in April is confirmation instead of news.
What it takes to get started
Print the first list in this article and go through it honestly. Mark the ones that apply to you and the ones you're not sure about — the not-sure ones are usually where the money is. Then get your profit and loss through the most recent month, your balance sheet, a payroll summary, and last year's return together.
One meeting is generally enough to get through all of it. We're booking these through October and November, and the calendar tightens up considerably in December, which is the least useful month to be doing this.
Who we are
For more than twenty years, Business Advisory Services LLC has handled accounting, bookkeeping, payroll, tax preparation, tax resolution, and business advisory work for small business owners, from our offices in Middleton and Eau Claire, serving clients throughout Wisconsin and the surrounding states.
Before the wall, not after it
Call the office at 608-831-4900, ext. 801, and let's get you on the calendar while the year is still open. Or call us on our cell phone at 608-347-3010. It's a conversation, not a commitment, and the worst thing that comes out of it is finding out you're already in good shape.
This closes out the series. Thank you for reading along — and if any of the six pieces described your situation a little too accurately, that's the one to call about.
Comments