I can only speak from my own experience but as I get older I'm less likely to enjoy being lost because of a greater appreciation of time being finite and a realistic appraisal of my own abilities. I think that's worth rebelling against because if something mostly makes sense either I'm lying to myself or it's too easy or it's not new. I want to fit in as many things as possible that don't make sense until they do, precisely because life is finite therefore I think feeling lost can be positive.