Your Financial Planning Checklist: Moves Worth Making Before the Holidays
Download our checklist of what's still worth doing before the fourth quarter gets busy with holidays and year-end deadlines.
Once the holidays arrive, the end of the year approaches quickly. Holiday get-togethers crowd the calendar, year-end deadlines cluster together, and the moves that seemed to have plenty of runway in September suddenly don't. This is not a comprehensive plan but rather a running list of things worth deciding on now, while there's still room to be deliberate.
Download Your Q4 Financial Planning Checklist
Roth Conversions Have a Hard Stop
December 31st is a hard deadline, not a soft target. There's no extension, unlike a Roth IRA contribution. If a Roth conversion has been on your list, the next several weeks are the last window to size it against your 2026 income.
Tax-Loss Harvesting Gets Crowded in December
The mechanics don't change in the fourth quarter, but the calendar does. Trading desks get busier, and there's less time to confirm a replacement investment doesn't trigger the wash sale rule. If you haven't reviewed your brokerage account for unrealized losses since earlier in the year, now is better than late December.
Either Way, Check These Three Things
First, any realized capital gains or harvested losses from earlier in the year that haven't been factored into your running total. Second, whether a bonus, RSU vest, or business distribution changed your income picture since your last projection. Third, whether you're still on track for the safe harbor threshold that actually applies to you — the 100/110% of last year's liability is often the simpler target if this year's income is higher than expected, since it doesn't require knowing your final 2026 number precisely.
Charitable Giving Decisions Benefit from Lead Time
Bunching multiple years of donations -- often into a donor-advised fund, or making a qualified charitable distribution if you're 70½ or older, both work better with weeks of lead time rather than days. Especially if you're contributing appreciated stock, which can take longer to transfer than cash.
RMDs Are Due December 31st
If you're required to take a distribution this year, there's limited flexibility on the deadline, and the penalty for missing it is real. If you haven't taken it yet, this is the point in the year to schedule it rather than leave it for December.
Trump Accounts and 529s Are Worth a Year-End Look Too
If you opened a Trump Account for a child this year, or you're weighing whether to fund one, the $5,000 annual contribution cap resets on the calendar year — same with any 529 contributions you're timing around a state tax deduction. Both are easy to forget until the calendar has already turned.
The Windward Approach
None of these decisions are complicated in isolation. The value is in making them together, with enough runway to be deliberate rather than reactive — which is exactly why we start this conversation in September rather than waiting for December.
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