My favorite learning experience (from a startup perspective) is also the one I think was the biggest failure. So much tech and a lot of dedication on my part, but looking back, the lost time with my wife. All of it really due to a lack of planning and an over commitment by management expecting engineering to step up. I don't ever recall being asked for estimates, just what needed to be done. I was in my tunnel at the time, building things.
I look back and the pre-devops, "devops" call at 1pm on a Saturday (after a 60+ hour week, they didn't have / hire sys admins before launching) was basically the end of line for me. Thankfully, the wife and I were driving back down 1 from SF to the Central Coast. We took our time and nourished the lack of coverage.
However, the grandparent specifically formulated the choice as a dilemma: (I'd work my ass off without options, but the options really make it easy to say "I will do everything in my power to make this succeed" instead of "I'd rather go spend time with my friends tonight"), and that is probably what the parent was referring to.