It never gets simple, only less fraught with importance. There is no wisdom in experience. The only things you gain are the dots to connect, a pattern which reveals the landscape but no end point. Everything is arbitrary.
At the end, even sincerity is all about playing games. Rules unknown, all improv, but never all in, trying to recall what you know about the trivia topic that is still and always a surprise. And there are always the winners, the losers, the cheaters, and those who refuse to play. I don’t know if I’m any good at this, but what brings me comfort is that no one is, and even if I appear to be messing it all up sometimes, we’re all stumbling around blind on the same chessboard, with the same set of broken pawns.