My impression is that if you meet enough people in your developer community who are organizers of things - be they conferences, meetups, trainings, or anything else - you will at some point hear them bemoaning the fact that everyone hates them, or similar. I've listened to it several times. I've felt it (but kept it largely to myself) a few. Tonight I find myself, finally, in the unpleasant position of having evidence to back it up.
It's generally understood that people taking on community organizer roles are just as flawed and prone to being wrong as anyone else, but are trying to do a good thing, and so we get given a lot of passes. For the most part - especially when the organizer in question is someone else - I think that's a good thing. It's difficult to put these things on, and nobody does it for the money, or even the fame, but out of a genuine desire to see their community grow and be better. I've learned over the past couple years to try and be delicate in my criticism of things other people organize, so it's clear that I mean to suggest ways to improve an event or group, and not to criticize the efforts of the organizer, and certainly not to criticize the organizer as a person. Because over the past couple years I've become more aware of how hard it is not to take even the most gentle and well-meaning criticism to heart and feel you've failed.
If you've never done any organizing, you might wonder, so what if you failed? So you tried to do something for the community, and it didn't work out, so what? If you've ever been on the other side, though, I think you begin to understand immediately. Before you even set up a website, or book a venue, or send out invites, I think most of us hesitate. There's an element of impostor syndrome I think we're exposed to at that point. I think a lot of us pause and ask ourselves, who the fuck am I to organize a _______, as though I had any authority on how a community _______ should be run? Maybe we wonder if someone famous shouldn't do it, or someone with a really successful open source project, or someone who's just, you know, better than we are. And maybe some of us stop right there because of that feeling. I spent years wanting to contribute in some way, not just with code, but to the community, before I was finally brave enough to start All-Girl Hack Night. It was that feeling that stopped me. So when someone tells you (what you hear as) you've done badly, you don't just feel like you've made a mistake - you feel like a liar, a fraud, a snake-oil salesman whose arrogance has driven people away from the community, never to return.
So like I said, I am very much feeling that as I sit here writing this. I know that I failed at least one person, and may have caused them to become more skeptical about participating in a group I organize, and in other groups like it. I guess in a way I'm writing this blog post to myself, even though I started off writing it to all my friends who I know have felt this way in the past, or who are doing brave things that may expose them to this feeling in the future. Maybe I'm writing it to everyone in these communities. Maybe I'm just writing it.
You can't make everyone happy. You just fucking can't. Sometimes the well-intentioned approach that seemed great in your head, and worked great the previous three times, fails fucking abjectly. Sometimes someone is livid at something that other people begged for. Sometimes you meant it as a compliment and it gets taken as sarcasm. Sometimes you hang the banners and arrange the flowers and set out the chafing dishes and nobody ever shows up. We can try to make people happy, and to provide value, and that's all we can do.
Bringing your A game isn't always going to be possible. The more you try to do things, the greater the odds that you will fail at some point. That's the risk inherent in trying. If there's never been a time in your life where you were trying to make things work out, trying to get all the pieces to fit together, and yet could see that the situation was just rapidly falling the fuck apart, and all the people were rolling their eyes, and suddenly half your vocabulary disappeared from right off the tip of your tongue and you seriously considered just running out of the conference hall and into the nearest forest.. I envy you.
Anyone who gives up on a community because one organizer fucked up was probably already looking for an excuse. Sometimes people will treat you like the hostess at the Cracker Barrel. Those people have most likely not decided to jump into the community with both feet. And yeah, maybe you did have the opportunity to convince them to, and maybe you did waste it. That sucks. But it's still ultimately a decision they have to make, to give the community permission to be wrong and to try and improve whatever they felt was lacking rather than just write it off as not worth their time. Even if you did the best job in the world, you still couldn't be assured they'd come out of it that invested.
There are damn few institutions of community in this industry. The long-running conferences tend to be corporate things employees get sent to so companies can market to them. The long-running mailing lists get increasingly off-topic until finally they're just slower versions of Reddit. I don't think I know of any meetups that even existed before the mid-aughties. If you manage to make something hold together more than a couple months you are basically magic already. And, really, it's better that way. We bring strangers together under the guise of community, and then we lose strangers to communities of friends they met while standing awkwardly at an open bar in a brightly lit hotel lobby wearing a plastic nametag. And if we organized that open bar, or even just the nametags, we have something there to be proud of. Attrition can bad, but it can also mean that it's working.
Anyway, if you were wondering, hey, why is it that every community organizer I know gets so hilariously emo sometimes, I think I have your answer. We do this shit to do good and make things better, but there's always the chance we'll do a bad job, or even do a good job but still let someone down. That can make you feel really badly about yourself. Yet people still do it, cause if they didn't someone else would have to, and then it would just sometimes suck for someone else.