Situation
Year-end equity planning
Year-end planning isn't December — it's October. By the time the calendar turns, the windows for exercising ISOs, harvesting losses, and shifting tax-year boundaries are mostly closed. This is the sequence to run between October 1 and December 31, in roughly the order to run it.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01How-to— EQUITY ADVANTAGE
Top 5 Financial Items for Tech Employees Prior to EOY
Five Q4 moves for tech employees: ISO/AMT review, tax-loss harvest, charitable giving via DAFs, max the 401(k), benefits selection.
5 MIN5 MIN - 02How-to— TAX STRATEGIES
Exercise ISOs up to (But Not Above) the AMT Tax Limit
Exercise just enough ISOs each year to fully use the gap between your regular tax and AMT calculation — capturing ISO benefits without triggering an AMT bill.
3 MIN3 MIN - 03How-to— TAX STRATEGIES
Multi-Year AMT Spread Riding
Exercise some ISOs each year up to your AMT free window, sell prior-year shares to widen next year's window — a multi-year plan to monetize ISOs as qualifying dispositions with minimal AMT.
5 MIN5 MIN - 04How-to— TAX STRATEGIES
Tax Loss Harvesting
Selling losing positions in the same year as appreciated stock offsets gains dollar-for-dollar — mind the wash-sale rule and net short-term/long-term separately.
3 MIN3 MIN - 05How-to— TAX STRATEGIES
Double-Trigger RSU Liquidity Year Planning
When double-trigger RSUs all vest at once on a liquidity event, expect a tax-bracket spike and low withholding — plan the income, the withholding election, and the cash.
3 MIN3 MIN - 06How-to— TAX STRATEGIES
Manage Your Income Tax Bracket
Time controllable income (NSO exercises, disqualifying dispositions) and stack deductions to avoid crossing into the next marginal tax bracket.
2 MIN2 MIN - 07How-to— TAX STRATEGIES
Leave an Employer in 4Q to Optimize AMT
Leaving an employer in Q4 splits the 90-day ISO exercise window across two tax years — doubling your AMT-free exercise capacity and letting you defer the AMT bill an extra year.
5 MIN5 MIN
Talk to a 30/40 Advisor
Want this applied to your situation?
A 30-minute consult tells you whether the frameworks in this reading list cleanly apply to your equity package — and if so, what the first three moves are. No pitch.
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