If your employer gives you stock options, save the cash to exercise them

One of my coworkers told me a story about another coworker who got laid off. The one who got laid off had stock options, and we think they would have stood to gain a lot if they had exercised them. But, having just lost their job, and being the primary breadwinner of their household, they couldn't justify a surprise expenditure on that kind of risk. So they had to miss the opportunity.

Since then, I've had a YNAB category for "money to exercise options." A savings goal on that category keeps pace with the rate at which my options vest.

This way, whenever I leave the company, exercising 100% of my vested shares won't be a financial burden. I can make the decision to exercise or not based just on how well I think the company will do, without short-term concerns like paying rent muddying the waters.