Two top do-overs:
1) Not be a dev and try harder to be an astronaut as was my original plan.
2) If #1 still gave trouble, at least not waste 6 years of my career doing a detour into social media and PR. It was the early days when the salary (6 figures) and bonuses (5 figures) at that level of the corporate hierarchy were nice. But other than a bulked up 401k and paid-off house, social media ended up being a dead end for me. Going back to dev work meant I had NOTHING skill-wise to show for that time. I am STILL trying to catch up.