I can relate to this on a deep level ;-P . I used to be that guy that got labeled deep, but I guess I'm a little bit far removed from regular society now so now I'm either an artist or a fucking weirdo X-D, or maybe just a wacky idealist.

I feel very similar to you about "winning". I take it pretty far though. When I work a regular job, I always think about who is benefiting from my actions and what will they lead to. "Ok, I am helping someone but who are they and what are they going to do with my help? Are they going to use this help to make it further in the rat race, stamp out competition and live lives that reinforce all the ridiculousness in the world?" And so it ha she become very hard for me to "work". I like that there are more and more people working regular jobs who see through the ridiculousness and are looking for ways to be real, or "deep" in their free time though. I feel it's much easier for me to relate to the "average joe" than a few years ago, part of it is surely me calming down and finding my own peace, but I think a lot of lingering problems have been pushed to the forefront and people are able to break out of at automatic mode.

I feel like I'm ready to go off topic so I'll end this comment here. It'd be nice to have you in our chat room ;-)