If you are like most business owners, December feels less like a winter wonderland and more like a race against the clock. Between holiday parties, closing out the books, and managing employee time-off requests, strategic planning often falls to the bottom of the to-do list.
However, the difference between a chaotic start to 2026 and a prosperous one is often determined by the decisions you make right now, in the middle of the holiday rush. As we approach the final weeks of the year, there are three specific areas—ranging from health insurance to tax compliance—that require your immediate attention.
Here is your checklist for wrapping up 2025 with confidence.
1. The Valuation Check: Key Person & Buy-Sell Agreements
Your business likely looks different today than it did in January. Did you land a massive contract? Did your revenue grow by 20%? Did you hire a VP of Sales who is now indispensable to your revenue stream?
If your business has grown, your risk has grown—and your insurance needs to keep up.
- Key Person Insurance: If your top rainmaker brings in $1M in revenue, but you only have a $250k policy on them, you are underinsured. Use this time to review policy limits to ensure they reflect the current financial impact of losing a key employee.
- Buy-Sell Agreements: Many partners fund their buy-sell agreements with life insurance. If your business valuation has skyrocketed in 2025, the existing insurance payout might not be enough to buy out a deceased partner’s shares, leaving the business in a cash-flow crisis.
Schedule a quick valuation review to ensure your safety nets are actually high enough to catch you.
2. The Tax Reminder: Corporate Estimated Payments
While we are insurance experts, not accountants, we know that cash flow management is the heartbeat of any small business. This is a friendly reminder that for calendar-year C-Corporations (and often pass-through entities depending on filings), the 4th Quarter Estimated Tax Payment is generally due on December 15.
Missing this payment or underpaying can result in penalties that eat into your 2026 profits. Check in with your CPA or tax professional this week to ensure that payment is scheduled. It is better to pay it now than to deal with the IRS headache in April.
3. The Strategy Shift: Planning 2026 Benefits Administration
Once the December 15th hurdles are cleared, take a breath and look at your administrative processes. 2025 brought new challenges in compliance and employee retention. As you prepare for 2026, ask yourself:
- Did our enrollment technology work smoothly, or was it a paperwork nightmare?
- Did employees understand their benefits, or did we field the same questions repeatedly?
Now is the time to look into upgrading your benefits administration platforms or hiring a third-party administrator for 2026. Streamlining these systems now saves you dozens of hours of HR work later.
Finish Strong
The end of the year is hectic, but checking these three boxes provides immense peace of mind. By locking in your group health plan, updating your business protection policies, and satisfying the tax man, you earn the right to truly enjoy the holidays.