Convert taxable wages into pre-tax benefits (health, FSA, DCFSA, HSA) — saves ~30% FIT + FICA.
IRC §125 Cafeteria Plan lets employees choose from a menu of pre-tax benefits: health/dental/vision premiums, Health FSA ($3,200 in 2024), Dependent Care FSA ($5,000), HSA contributions, group term life ($50K), adoption assistance. Saves ~7.65% FICA + 12–37% FIT on elected amounts. Requires written plan document + annual nondiscrimination testing. NOTE: >2% S-corp shareholders CANNOT participate in a §125 plan (they must take deductions via §162(l) self-employed health).
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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.
Take unpaid sabbatical year — convert Traditional IRA to Roth at 12/22% bracket vs 32/35% working years.