Year-end tax planning with stock compensation
Most equity tax planning is timing, and most timing options expire on the last day of the calendar year.
Project first
Estimate total income including vests, bonuses and gains, then compute both regular tax and tentative minimum tax before deciding anything.
Then act
Exercise ISOs up to your crossover, harvest losses outside wash-sale windows, bunch charitable gifts of appreciated stock, and top up withholding to reach safe harbour.
Split across the new year
Exercising in late December and early January uses two annual AMT exemptions within days.
This article is educational and not tax, legal, or financial advice. Talk to a CPA or tax advisor about your specific situation.