Exercise Timing Planner

Should you exercise your stock options now or wait until an exit? Compare the financial outcomes.

Grant Details

Grant Type

Strike Price ($)

Current FMV ($)

Exit Assumptions

Expected Exit Price $40.00

Years Until Exit

Tax Profile

Filing Status

State

Annual Income ($)

Difference (Exercise Now vs Wait)
—

	Exercise Now	Wait Until Exit

Timeline Visualization

Net Gain by Exit Price

Long-term vs short-term capital gains

Long-term capital gains apply to assets held for more than one year. Federal rates are 0%, 15%, or 20% depending on income — significantly lower than ordinary income rates.

Short-term capital gains apply to assets held for one year or less and are taxed at your ordinary income rate (up to 37% federal).

For ISOs, exercising early and holding for 1+ year from exercise (and 2+ years from grant) means the gain qualifies for long-term rates. Exercising and selling at exit on the same day means ordinary income treatment.