Are you still in Chicago? There was recently a gathering at the Art Museum garden with ~30 people in attendance, and a few people were discussing trying to keep the momentum, myself included. If you are around, I would like to invite you to give it another go. Regardless of your current location, I’d be curious to hear more details about your particular experience in this locale.
Hi Joshua, sorry I missed this comment! I’m not in Chicago anymore, though I’m still invested in the group’s success. I’ve been meaning to write up a postmortem of the version of Chicago Rationality that I ran (and later passed off to Peter), but I recently started working full-time so I’m not sure when I’ll get around to that—for now I can just say a couple of things here.
One is that I think Chicago is more spread-out than a lot of major cities, which makes it really hard to pick a good location—e.g., we initially had our meetups in Hyde Park, but we had very low regular attendance because most people weren’t willing to trek all the way down to the south side; and when meetups were moved to Harold Washington Library we basically lost all the UChicago students. Similarly Northwestern is way far from any central location you might pick, but in the opposite direction. This makes it really hard to sustain a core group of people who will regularly show up.
Another is sort of a catch-22, where because there’s not a lot happening in Chicago in terms of rationality or EA, there’s not a lot keeping really hardcore rationalists/EAs in the city. Like, I joined a version of Chicago Rationality in March of 2015 that only lasted for three months, at the end of which all four other members moved to the Bay to work for EA organizations. I think this was almost certainly the right call for all four of them, because they didn’t have strong roots in Chicago, weren’t well-positioned to earn to give, and were good fits for the culture and organizations they joined in the Bay, and most importantly because there was no community for them in Chicago and no way for them to have an impact there.
As for why I think there hasn’t been a lasting community in Chicago so far: Chicago isn’t flooded with programmers like some other cities—which is a big deal because programmers are way disproportionately into rationality/SSC—and it doesn’t have particularly unique industries that would draw rationalist-type people. Here I’m thinking of Seattle (which has sustained a large rationalist community), where lots of people don’t want to leave their jobs at Amazon, Microsoft, and SpaceX. (See also Paul Graham’s essay on cities, which led me to reflect on Chicago and find it to feel not at all ambitious, at least to me).
So those are my super rough thoughts on what it’s like to try to make a community work in Chicago. I definitely don’t think it’s impossible—there are communities in much weirder places with many fewer rationalists—but I think it’s important to keep these considerations in mind, and maybe using an atypical strategy to accommodate them.
For example, I can imagine that you might want to have weekly meetups switching off between three regular locations—one closer to Northwestern, one closer to UChicago, and one downtown. That way people who weren’t able to easily travel to the other locations could still make it to ~one meetup per month, which would allow them to feel like part of the community even if they’re not at every event. If the three locations each had a different host, this would also help with leadership redundancy (which I talk about in the post).
For the ‘not a lot happening in Chicago’ concern, I think you’d just want to be careful to not place all your eggs in a basket that’s likely to move away soon (like me, sorry). You need people who are committed to staying in Chicago and building a community there, rather than just excited about the thing but apt to leave for greener pastures. This means that while universities might be good places to find new members, you shouldn’t build your group such that it relies on students to survive.
Hope this was helpful, and sorry it was so long! Feel free to ask more questions :)