A typical year-end list piles everything onto December 31: your HSA, your fourth-quarter estimate, your cash balance contribution, your charitable gifts, your tax-loss harvesting, all of it. When everything's due at once, the things that genuinely expire get the same frantic attention as the things that could comfortably wait until spring.
In this episode, Jared sorts the real year-end list into four buckets that actually end at midnight on December 31, payroll (401(k) deferrals, Roth catch-up rules for surgeons with prior-year wages over $150,000, withholding), portfolio (tax-loss harvesting and the wash sale trap, Roth conversion timing), giving (RMDs, qualified charitable distributions, the new charitable deduction floor and cap, annual exclusion gifts), and the practice (the pass-through entity tax election, bonus depreciation, cash balance plan design changes). Then he covers the three dates that crowd most year-end lists but actually land in 2027: the Q4 estimated tax payment (January 15), HSA contributions (April 15), and cash balance funding (with the return).
He walks through several worked examples along the way, including an $8,500 401(k) deferral gap that's gone for good on December 31, an $80,000 tax loss that can vanish because of a wash sale, and a $26,000 difference in federal tax depending on which year a Roth conversion happens in.
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