| HN Mirror

By unexercised I mean unexercised. Stock options vest continually (well, usually monthly or quarterly usually, after the 1-year cliff); when they've vested, you have the right to exercise them, and they're considered your property. You only exercise them when you choose to, and it's at that point that you're taxed on the difference between the current stock price and the strike price.

Many of my coworkers would auto-exercise-and-sell their options immediately as they vested. If I'd done this then it would've added between $15K-$60K for each of the first 5 years, but the last year would've been about $130K instead of $350K (I benefitted significantly from the stock price appreciation of GOOG, even if I did screw up nearly everything tax-related).

I left Google because five things happened within a year or so: #1 I started feeling bored at work #2 My existing project ended and I couldn't find one that really excited me #3 I passed a million bucks in liquid net worth #4 The outside tech world started entering what seems to be a period of high uncertainty and #5 I started thinking seriously about marriage & kids and realized I only had a few years left. So, in the spirit of YOLO and with immediate financial concerns taken care of, I figured it was time to do some things I'd always wanted to do.