Going all in on the stock option program, even if it was a little risky. I remember the argument: There's no lottery or casino that'll give me odds like these. I also left when we'd grown to the point where middle management didn't want to understand that when the program ran out (4 years) and had to be restarted at the new validation, that was basically a static pay cut for me. I get paid a lot more now, but I still made more from stocks than work last year.
Second, our apartment. It's a lot like a row house, except it's in the city. The other part backs right up to the park.
Third, maxing out parental leave with both of our kids at a company that (as, more or less, a recruiting gimmick) topped up parental leave pay from the capped 80% to, iirc, 100% with no cap. They turned out be quite dumb about this and had shuffled me into a corner when I came back. I was ready to put my back into it, but well, I guess not then.