[crcastle]

Exercise != payout

Exercising options generally gives you shares in the company, not a payout. A payout would require selling the shares. Normally you can exercise vested options at any time very easily. Selling those shares you received from the exercise for cash is not as easy.

[aetherson]

I understand all that. But typically you must exercise incentive stock options within three months of leaving a job, or lose them.

If the OP can exercise his options right now for an amount of money he considers not terribly significant, then he could quit his job now, and if the old company monetized in the next couple of years (which he stipulates is reasonably likely), then he can still get the payout for it.

If on the other hand his options are not vested, or he can't afford to exercise them speculatively, then if he changes jobs now, he throws away significant equity that he thinks has a good chance of monetizing.