Like Jon Law, I took great pleasure in beating my classmates. Unlike Jon Law, I had a deeper motivation beyond that, so not winning wasn't really a big deal to me. And ultimately, I saw the race to valedictorian as a Wargames scenario - the only way to win the game is not to play.
Granted, my approach was "the only way to win the game is to break the rules."
I knew I had to toss out the entire "Winning!" thingy.
The problem is that I never replaced it with anything.
I tried active failure/self-sabotage during college, which didn't really solve anything and eventually got old.
I also tried the "not really caring" in law school. I actually declined to complete what they presented as a core requirement to see what would happen. They just changed the system so that I could complete it. Interesting.
I'm pretty good at vacillating between passivity/avoidance and periodic self-sabotage these days.
I still need some sort of overarching intrinsically motivated purpose to cohere around.
I will say that my initial "breaking the rules" approach is quite useful with bureaucracies.
