I am by far the least successful person in my "tech" peer group and have struggled with jealousy and depression because of it. I don't have the answer for you,

I am by far the least successful person in my "tech" peer group and have struggled with jealousy and depression because of it. I don't have the answer for you, but a couple things I've done. (A lot of this might not work for you, because I'm not ambitious and I do accept being mediocre) For my "real" friends (defined as people who would like me even if I were homeless and broke), I focus on what makes us friends: it's not technology or success, it's experiences and time spent hanging out. I emphasize those behaviors and de-emphasize "work" discussions. For friends who just want to talk about their businesses and successes, I distance myself. It might not be nice, but I have to take care of myself emotionally first, and having my face rubbed in someone else's success doesn't make me feel good. I also try to befriend (even just as casual acquaintances) people significantly lower on the economic scale. That way when one of my successful friends posts on Facebook about their third tropical vacation in as many months (and my default response is to get upset that I can't afford the time or money for that kind of trip), then I also have another post to read about someone who is struggling to make rent, and that gives me perspective. Really I am in a good place overall, not the best place, not anywhere close to what SV would call "successful", but there's a whole big world out there. While we all squabble over who has covered more of the top half of Maslow's hierarchy, there are a lot of people still working on the bottom half. It's important to have a few people to put real faces on that to keep me grounded in reality.