> It's hard to call those choices "wrong" so much as selected based on the flavor profile of a younger, much more anxious me, whereas I am now considerably more

> It's hard to call those choices "wrong" so much as selected based on the flavor profile of a younger, much more anxious me, whereas I am now considerably more willing to swing for the fences now that I've realized just how high the ceiling, and how low the bar, really are As someone in a similar situation where it has become time to make bigger bets: Those earlier smaller, safer, bets enabled you to get here. If you made the big bets too soon, you'd run out of swings. Kelly criterion talks about this in a mathy sense. This fantastic old HN comment talks about it in a more relatable way: Entrepreneurship is like a carnival game https://news.ycombinator.com/item?id=15659076 https://news.ycombinator.com/item?id=15659076