HSA is the ONLY triple-tax-advantaged account: deductible in, tax-free growth, tax-free out for medical.
HSA (High-Deductible Health Plan required, $1,600 individual / $3,200 family deductible min in 2024) is the only account with all three: (1) contributions deductible from federal + state income tax AND FICA if via payroll, (2) growth 100% tax-free, (3) withdrawals tax-free for qualified medical. Max: $4,150 self / $8,300 family + $1,000 catch-up age 55+. Pay medical out-of-pocket, KEEP receipts, invest HSA in index funds for 30+ years, withdraw decades later tax-free reimbursing decades-old receipts. Effectively an unlimited-life Roth IRA for medical.
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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.