Take unpaid sabbatical year — convert Traditional IRA to Roth at 12/22% bracket vs 32/35% working years.
During a planned unpaid sabbatical, mini-retirement, or maternity leave year with dramatically reduced income, execute large Roth conversions from Traditional IRA/401(k). Fill up the 12% and 22% brackets ($94K MFJ / $47K single at 12%; $201K MFJ / $100K single at 22%) with converted amounts. Vs converting during 32/35% working years, saves 10–13% per dollar converted. Also ideal window for QSBS §1202 exit (5-yr hold hit) and long-term capital gains harvesting (0% LTCG bracket up to $94K MFJ).
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Contribute up to $46K/yr additional (beyond $23K deferral) to after-tax 401(k), convert to Roth same-day.
Public sector + qualifying nonprofit employees stack a 457(b) alongside their 403(b)/401(k) — 2× annual deferral space.
Defer unlimited comp to retirement / future years — bypass 401(k) $23K cap on high-income executives.
Exercise ISOs early (bargain element = AMT) — pay AMT credit, get long-term cap gains + recover AMT in future.
Elect §83(b) within 30 days of restricted stock grant — pay tax on ~$0 value, all future growth is capital gains.
Contribute max to §423 ESPP with 15% discount + 6-month lookback = ~26% annualized risk-free arb.
10b5-1 trading plan lets executives sell during blackouts; costless collar protects downside with no cash outlay.
HSA is the ONLY triple-tax-advantaged account: deductible in, tax-free growth, tax-free out for medical.