>In the former, you understand it better and better as you age, but in the latter you're left with knowledge that's of no use while the next generation is ahead of you just by the privilege of being young.

I'd put it more like: you're left with knowledge that sees right through bullshit and the same-old promises and error modes, but nobody's buying. And the next generation is hired precisely because they're naive to all of that to repeat the same mistakes eagerly while sociopaths profit.