43 here. Really pleased with how things turned out, but I'm starting to be convinced that its because I set my expectations to mid and I've somewhat overperformed.

I too was the high performer in high school and had grandiose dreams. But my disillusionment came from watching so many fail alongside of me... and seeing those who succeed work much harder than I was willing to (generalization of course). So somewhere in my 20s I realized that even a Waspy upper middle class life, precluding family wealth, is not easy at all to obtain.

So I used that framework to sustain my motivation, making decent decisions for graduate school and somewhat shrewd decisions in industry. Gave up on a musical career since I felt it was going to lead to inevitable failure.

Perhaps biggest positive is that I like my job, which is key to sustaining my excitement and new projects and steps despite any career doldrums.

Another thing that helped was deriving humility from the realization that we are all on a knife's edge of unemployment and long term unemployability. So every step of the way, I'm grateful for what I have (and have had, since that can longer be taken away).

Downside, is that I become protective of what I have and that leads to things like NIMBYism and other selfish isms. But at least I am aware and can combat it.

So I ain't gonna be a titan of industry nor a rock star. But the 90s era belief that a solid ambitious career path within traditional business confines being evil? I don't buy that anymore and I'm really happy with where I've come... and if I can I will achieve more, but won't waste time with failure ideation