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Run the numbers before December 31
Once the calendar flips to January 1, most of the moves that lower your 2026 tax bill are gone. You have about eight weeks.
Year-end planning for a sales rep starts with one projection: what you'll actually earn this year, and how much tax you've already paid on it. Everything else comes out of that number.
Project the whole year
Pull your latest pay stub. Add up your base, every commission check paid so far, and what you expect to land in November and December, accelerators included. Then find year-to-date federal withholding on the same stub.
Here's where reps get caught. Your employer withholds a flat 22% on commission checks, but at $250,000 of income a good chunk of that money lands in the 24% and 32% brackets. That gap is why I tell clients to set aside an extra 10% of every commission check. If you didn't this year, you'd rather find out in November than in April, because you can still raise withholding on your last few checks or make an estimated payment by January 15.
Max what you can
The 2026 401(k) limit is $24,500, and contributions only count through payroll, so your last December paycheck is the deadline. If you're behind, bump your contribution percentage now while there are still checks to pull from. Big Q4 commission checks make this easier. In the 32% bracket, every $1,000 you put into a pre-tax 401(k) cuts your federal bill by $320.
Your HSA and IRA give you until the April filing deadline. The 401(k) doesn't.
Harvest losses, and gains
Open your taxable brokerage account. If a position is worth less than you paid for it, selling it locks in a loss that offsets your gains, plus up to $3,000 of regular income. Just don't buy the same investment back within 30 days, or the IRS disallows the loss (the wash sale rule).
The other side matters if you need cash soon. Planning a down payment or a new car early next year? Sell some winners before December 31 and let the losses you just harvested absorb the gains. You get liquidity out of the account and keep the tax hit small, instead of selling in a panic in March and eating the whole bill.
None of this takes long. An hour with your pay stub and your brokerage statement gets you the projection, and I'm not a CPA, so bring your tax preparer in before you make the moves. But walk into that conversation knowing your numbers, because January 1 closes most of these doors.
- Chris
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