Employer pays up to $5,250/yr for employee tuition OR student loan principal/interest — tax-free through 2025.
IRC §127 lets employers (including your own S-corp/C-corp) pay up to $5,250/yr per employee for tuition, books, fees — AND under CARES Act (extended through 12/31/2025) for student loan principal or interest payments. 100% deductible to employer; 100% tax-free to employee (no W-2, no FICA). Owner-employees eligible if plan is written, non-discriminatory. For an S-corp owner with a spouse/child on payroll, that's $10,500+ of tax-free education/loan money per year.
Click Generate advisory deep dive for mechanics, IRC citations, a step-by-step execution plan, a worked numeric example on your profile, costs, risks, and this-week actions.
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.