The other night I was marveling over the connections between people I follow (but don’t know personally)¹ on Twitter. The details aren’t really important, but it was a scene repeated all the time. Musician links to a work of art made by someone I follow due to their work in games who is connected to a cartoonist who’s work I love and also via another connection to someone who makes software I love. Et cetera.

This happens all the time. I’m regularly amazed by how people who appear to have little direct connection (besides being connected through my own interest in their work) seem inevitably to find each other. It’s easy to imagine some big playhouse where they all hang out and the app makers are playing a board game with the independent journalists while some game developers are hanging out across the room with a musician discussing books whose authors are off playing their video games.

The image is at once aspirational and jealousy-inspiring. So it shouldn’t have been a surprise when, an hour later, I saw a discussion unfold about whether the just-completed XOXO-fest was nothing more than a cool-kids club.

XOXO-fest, as best I can tell, is, more or less, a conference designed to make my playhouse a reality for a few days. I know nothing about it beyond the fact that a significant fraction of the people I follow seem to be somehow involved with (or at least paying attention to) it. It brings together a cross-section of people who make things in a largely—scare quotes—indie fashion to talk to each other about how they make things. And having watched some other festivals and conferences devolve as they grew,² they appear to be trying to respond to their success without growing too fast beyond the intimacy that defines them.

I’m not so terribly interested in the good or bad behavior of the conference organizers. It’s a tough problem to solve, keeping the atmosphere of your conference intimate and engaging without appearing to be (or flat out being) elitist assholes. What is more interesting to me is how we react to the notion of all those cool kids out there living the life.

Most of us weren’t popular in high school, or at least didn’t think we were, and we don’t think of ourselves as cool kids now. One of the most simultaneously encouraging and depressing notions I’ve encountered is the fact that few people whoa are successful in their fields don’t feel that they are faking it. It’s natural to transfer the feelings of resentment we may have had toward the popular kids in high school on those connected, successful creators in their playhouse. And further, to wonder, if our desire to be among them is as empty, and pathetic, as a high school outsider trying to get an invite to the jock’s table.

And that’s where the comparison breaks down. In high school, for the most part, popularity wasn’t based on achievement. Not really. Not even achievement in the sports most schools seem set up to reward. For one, high school students simply haven’t had much time to achieve. Mostly, popularity was based on proximity to the popular. How you got the nod didn’t matter so much, whether it was wealth, a team affiliation, beauty, or even honest friendship, what mattered was that you were in. And if you weren’t, you wanted to be.

But when I look toward those indies in their imaginary playhouse, I’m not looking for friends, or an invite to a party. Sure those things would be nice. They seem like great people, for the most part, and I bet their parties have great decorations. What I really want is to have made something good enough that people who make things I respect notice. That I could meet the a developer who worked on one of my favorite games and have them tell me, “Oh, hey, you wrote X. I loved that.”

The desire to be a part of that kind of club seems, to me anyway, a much healthier aspiration. And to be clear it isn’t the only, or primary, reason I’m driven to make things. I’m not looking for the things I make to be a ticket to some insider’s club. And I’m sure that no matter how successful I ever get, I, too, will always feel I’m faking it. Also, to be sure, there’s plenty of cronyism, cliques, and discrimination in the adult world. But it’s important to separate true admiration of role models from sycophantic admiration of the popular for popularity’s sake, even when they can be a little hard to tell apart at times.