Contribute max to §423 ESPP with 15% discount + 6-month lookback = ~26% annualized risk-free arb.
IRC §423 qualified ESPP with 15% discount + 6-month lookback: purchase price = 85% of LOWER of start-of-period or end-of-period stock price. Contribute maximum (25% of comp or $25K/yr statutory cap), sell IMMEDIATELY on purchase date. Guaranteed 17.6% return per period (2 periods/yr = ~35%+ annualized). Tax: discount is ordinary income, gains are short-term. If held 2 years from grant + 1 year from purchase, qualifies for preferential §423 tax. Immediate-sell strategy skips tax optimization for guaranteed lock.
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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.
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.
HSA is the ONLY triple-tax-advantaged account: deductible in, tax-free growth, tax-free out for medical.