Some of your posts are a bit self-involved, but when I read some of my old posts they sound sickeningly pretentious to me, so I can sympathize. All the way through the end of college I was given the impression that I was this bright shining star who would achieve so much because I was so smart (Top 5% of my class at an Ivy League school! That guarantees me everything else I want in life, right?), but grad school and the workforce have certainly knocked my ego down a peg in that regard. So maybe that has changed me a bit. On a spiritual level it has been gradual internalization of the idea that "I" don't really exist, that the reality is more like we're some sort of meta-entity with illusions of fragmentation. So that has helped. But I've also always struggled with the issue that I want to live my life by love and compassion, but I can have a hard time connecting with people. I think finding friends with whom I could gain social confidence helped.

I don't know how helpful that is, but you aren't alone in dealing with this sort of thing!