Hi Jas! After our recent meetup on moral mazes, we were talking in the KWR discord about how much one can trust someone who says that there are no mazes or status games being played in their corner of the world. You had some interesting things to say in that conversation, and both of us leaned towards being somewhat skeptical.

Separately, both of us have organized and been deeply embedded in local rationality scenes - you in New York, me in Waterloo (and broadly Canada). I think there were themes brought up in that conversation that could be worthwhile to explore in this context.

I'll list a few thoughts to get us started, and you can pick how you want this conversation to go, how does that sound?

Here are some of my takes:

• One feature of rationality communities that I think is really valuable, and want to work to preserve, is how socially oblivious or uncharismatic people are accepted into the community, and can eventually thrive.
• Recently, I've been feeling kind of bleak about this feature's staying power for reasons I outline here. People were starting to raise the alarm bells about discords full of people strategizing on gaming EA applications right before the FTX collapse. Now nonprofit funding equivalent to five to ten new openphils are going to be here again quite soon, and I just can't see that not having a massive effect on the culture.
  • (I know a few teams with situational awareness that are starting to build capacity and orgs about this. I'd like this funding situation to be taken as a given and not litigated here.)
• One failure mode I see from startups, which are sort of similar: The original team is comprised of people who are smart and caring and cool, but they prefer more charismatic and likeable folks over uncharismatic and disagreeable ones. Those middle layers slowly set the organization in a less good direction over time. I'm sure the Berkeley group houses are going to be fine, and I'm genuinely glad for that. But I don't run my meetups for the established bay area community; I run my meetups, at least in part, for the uncharismatic seventeen year old version of myself who felt alienated and lonely and disconnected from humanity, and who didn't know that there were others like her in real life until she went to a meetup in Ottawa.
  • It seems valuable to me that other seventeen year olds in that situation can find this community, that when they do they feel welcome here, and that this community helps them thrive.
  • There's an adjacent community of seventeen year olds who have viral tweets that Tyler Cowen sees and grants them Emergent Ventures money about. I don't not care about those teens, but on the whole I think they'll make it out fine.
• You say: I also believe that the optimal amount of power-seeking-ness is far from 0. It's important to have teeth. I entirely agree; we all know the adage about well-kept gardens. There were occasionally people who showed up at my meetups who actively degraded the culture in more status-oriented and mazey ways, and it was good that I had enough teeth to kick them out. I wish I had more, actually! But by default, I wasn't trying to suss out every new person that walked in the door, and I'm nervous about that maybe having to be the reality in the future.

As you know, I've been thinking about this more since I'm moving to Toronto soon: leaving my old meetup group, and starting a new one. Though I'm really proud of what I built here in Waterloo, I've also started to think more about what I might want to do differently this time around.

Hi Jenn! Thank you for starting this conversation.

What attracts people to the rationality community in the first place? In the two-decade history of the broader community, we've already seen the answer to this question change.

[circa 2006 - ] Hanson and Yudkowsky published on Overcoming Bias. Yudkowsky conceived of the idea of existential risk from AI, and published the Sequences to find and educate people in rationality so that they can hopefully figure out how to mitigate risks from advanced AI. A lot of people formerly in the New Atheist Movement congregate around these writings.

[2009 - ] LessWrong launched. Some people started their own blogs.

[2013 - 2021] Scott Alexander published on Slate Star Codex. The blog got pretty popular, and during this period there were a lot of meetups popping up in cities where Anglophone nerds tended to live—Berlin, Waterloo (thank you for your service :D), and of course lots of major cities too. I got introduced to SSC in 2016 by a friend linking me an SSC post and telling me about LessWrong, and that was how I found the community.

[2021 - ] Slate Star Codex metamorphoses into Astral Codex Ten on Substack, and becomes spectacularly popular. By now the community had our first global meetup coordinator because there were regular and irregular meetup groups in so many places around the world. Many people learned about the rationality community through the twice-a-year ACX Meetups Everywhere announced on the blog. FTX started taking off.

[circa 2022 - ] Lightcone Infrastructure purchased Rose Garden Inn, retrofitted the buildings into an incredible event venue, and started hosting a lot of events attended by a lot of cool people. Many people learned about the rationality community through attending one of these events. ChatGPT released.

[circa 2024 - ] AI as a concept permeates our collective consciousness... AI risk becomes a mainstream concern. Many people learn about the rationality community because of AI.

Ah, yeah! Jumping in before you finish your thought to say that I've been thinking through the more recent cultural changes too, though not in the context of community organizing work.

I wrote this shortform outlining a pet theory i had about why the community has gotten more right wing, and in my manifest 2025 retro I said stuff like:

then i come here, and i'm kind of like, who are all these guys? and they're all so young? and then i met the extropian, and... now i think a more accurate model might be like - whatever the rats were to the extropians, the people at manifest are to the rats... something new and different is emerging from us. and i like some parts of the new thing and really dislike other parts!

...alright, carry on!

Manifest 2025 is a good point, and you mentioning that made me realize how diverse the community has become... Actually I would go one step further: the boundary of the community has become so nebulous, maybe it's now less of a community and more of a scene. "Rationalist-adjacent" is a term that I've seen people start using in recent years, and I've met quite a few people at Lighthaven who made it very clear to me that they were "not a rationalist."

There are people who like reading Astral Codex Ten and people who take AI risk very seriously and people who work in the AI industry and people who bet on prediction markets and people who are into Progress Studies and people who like science fiction and makerspaces and people who like computers and economics and people who are into life extension and... all of these categories have some sort of overlap, and I don't know how to model the "median community entrant" because I find it hard to define "median" "community" or "entrant."

One observation that I had in New York was that, my fellow organizer Tristan was really good at hosting meetups with great turnouts. His meetups had interesting intellectual topics like "options in finance and real life"—not orthodox rationality but had lots of people interested; whereas my attempts to run a series of rationality-skill-training type meetups based on the CFAR workbook had much less turnout. That was probably when I realized that people were not here for the rationality... and/or there was something else I was doing wrong about community organizing.

When I think about the evolution of the rationality community, one lens I use is about growing up, both in an individual sense and a collective sense. In an individual sense, many members of the community went on to take on projects bigger than themselves: companies, blogs, relationships, books, marriages, children... And in a collective sense, the community nonprofit, Lightcone, serves as some sort of infrastructure for a lot of important Anglosphere intellectual activities. I sense a general increase in the level of complexity in the air.

A corollary of the "growing up" frame is that the community has been a place for people to grow up, hopefully becoming a little less socially oblivious and a little more charismatic. I certainly was quite insecure and anxious when I encountered the community in my early 20s... I cringe a little thinking about my past self, and I feel grateful for the community for being the catalyst for a lot of my personal growth. I think this is true for quite a lot of people who have been around for a while.

There's another thread, which is that a high-trust environment can exist because something can enforce accountability for defecting behaviour, like if everyone is a friend's friend, or employed in the same industry and care about their reputation. The lack of definable boundary of the community plus the sheer amount of people means we do not really have a high-trust environment at large.

So, how do you build the garden for 17-year-old Jenn given such complexity? My guess is that it comes down to friendship. Maybe initially you get to know each other because you like the same ideas. Going through changes together over the years is an opportunity for you to really learn about each other, then you become good friends with the people whose character you really do admire, witnessing each others' lives unfold. There are two elements of this process: finding your people, and the test of time. On the former, you're already doing great by writing on the internet! On the latter, I think the upcoming landscape change is a good opportunity to learn about people, as well as ourselves.

I want to separate the concept of "the community" and the concept of "people in the community" here. The wonderful things that helped your younger self thrive were not done by "the community"; they were done by the wonderful people you met. I think "the community" is becoming too abstract of a concept to be helpful here, and focusing on the individual people might be more helpful. For example, asking "can this person be trusted to use $X of funding effectively?" is a better question than "is this community trustworthy?"

The distinction between close-knit community and more wide-spread scene seems useful. And one good part about becoming more of a scene is that people who are into progress studies and those that are into AI safety and those that are into animal welfare can still run into each other at parties and events, but they're not stuck going to the same meetup that serves them all equally poorly.

And if the scene is big enough, I think you're right that instead of focusing on the network as a whole, a good instinct is to focus on building my own sub-community inside it? And perhaps it's the only thing I can do, considering the increased complexity in the air.

Which is not to say that communities themselves are not complex. I recently came across Wendell Berry's definition of community, which I felt drawn to:

A proper community, we should remember also, is a commonwealth: a place, a resource, and an economy. It answers the needs, practical as well as social and spiritual, of its members — among them the need to need one another.

Putting all those pieces together: perhaps the question to ask isn't "what can we do to prevent the community changing in undesirable directions?" The question should be more like... "given the evolving shape of the scene, how do we build a community inside it that can maintain the common weal?"

And along those lines, when I think about the difference between your meetups and Tristan's, my intuition is that both are genuinely good, and merely provide a different mix of nutrients for the scene/community/commonwealth. Numbers are important, but they're not everything.

The community growing up together is also an interesting frame. Thinking about local history:

• I sort of took over the meetups from Sean, after he moved to Toronto.
• Before Sean moved to Toronto, there was a previous group there, which fizzled out by when I was in high school (they took place at a bar and I was too young to go). One of the organizers of that group now lives in Waterloo, by chance. Recently I got to talk to him a bit. He's been out of the scene for a while, and doesn't know Sean at all.
• The current Ottawa group has been going strong for over a decade, and I'm glad to call many people in it my friends. There is an older gentleman in the group, who was a regular at the previous meetup group in that city. According to him, in the mid 2000s, everyone started getting married and having kids, and so the meetup dissolved.

It's good if a well run meetup group can continue indefinitely. But if there is rich soil to work with, even if the fields lie fallow for a bit, someone else will come along and pick up the plough. And now I wonder: if that previous meetup in Ottawa didn't dissolve, and the room I walked into as an intern was one that was full of forty year olds instead of twenty year olds, would I have stuck around?

Which is to say: perhaps I'm borrowing trouble, and I should trust the next generation to take care of themselves. Perhaps I should focus my attention more to what my own cohort needs? (There are flailing seventeen year olds, but there are also flailing twenty-seven year olds, and perhaps I am, at this stage of my life, better equipped to help the latter?)

There's another point I want to raise, though I'm anxious about saying something like this. The two months I've had since Inkhaven have been kind of strange. I get emails now from errant readers regularly, and one of them told me it's passed around between a bunch of interns at a place I didn't really expect. Additionally, two new people came to the meetup last week, and both of them mentioned reading my blog.

One reason I went to Inkhaven, and am choosing to focus on writing more, is exactly to become more of a prominent attractor. I want to plant my flag here in Canada, and say "hey, if you stay here too, you can hang out with me at the cool events I run, and meet the other weirdos in my network". I want to create a sustaining, viable alternative to moving to the freaking Bay! And then the gambit works, and it... honestly makes me kind of want to die of mortification a bit. While having that beacon is good, I worry that it works at cross-purposes somewhat to building a scene that is relatively immune to celebrity-oriented status games :^(

Which brings me to your next point, about high-trust communities. Even the dreamtime is partially illusory: though mild, the rationalist community has always had status games, social climbing, people angling for proximity to Eliezer or Scott or whoever. I was lucky enough to be out in the boonies where I was spared. You, in New York, felt it more, which is why I think you might have interesting things to say. And it definitely seems true to me that enforcement mechanisms are important for maintaining nice norms. (If that wasn't the case, we'd have nice norms by default.)

So I agree: it's could be productive to focus on the individual people, rather than the abstract idea of a community. So what can one say about individual people, and the way they behave?

Some interesting points you brought up that I'd love to see you riff on more:

• "I think how people behave is the product of both who they are and the incentives given by their environment. I think the average person behaves less mazely if they are in a less mazely environment and more mazely in a more mazely environment. It is as much about the person as what the environment actually rewards and punishes (is it real good work or is it talking about how much work you've done?)"
• "I think places where the work is geniunely demanding, where there's more stuff that needs to do than people, as well as good rewards for people who get things done, set up incentives for people to actually do the work than to play maze games."

And one last thing I'll flag is that I'm quite suspicious of advice along the lines of "just trust the vibes". Vibes are just sanewashing discrimination, and I am not immune to charismatic and pretty people! Very often I have initially misjudged who is a good fit or not, because dumb monkey social brain easily tricked. Moreover, many people take a few months (or even years) to fully integrate, and I want to hold that space for them.

I might have a slightly more pessimistic view of community than you, because when I read the Wendell Berry quote you mentioned, my first thought was "that's an extremely tall order, you're not gonna get that in today's Western society." I think it goes back to the level of complexity that we're dealing with here. It might be true in a different place or time, when the way people navigated the world was to stick with their clan no matter what; where your survival became precarious the moment you got ousted by your tribe. There's a correlation between how much one depends on a community versus how much one invests in that community. You and I live in a world today where people are seen as individuals first and foremost, that people are expected to be responsible for their own life outcomes. As a result people might be in multiple communities but don't depend much on any single community. Community membership becomes something one has rather than one's identity.

I think a community that answers the practical and spiritual needs of all of its members, where the members need one another, is only possible if all members are content with not developing identities that come in conflict with any aspect of the community. Not possible in an individualistic society, and definitely not a bad thing in itself—individual rights and freedom! Woohoo!

There's a distinction that I want to draw your attention to here: social group versus institution. A social group is primarily about people's relationships with each other. An institution has things that a social group does not have: clearly defined membership, something that serves the function of a constitution, rules of governance, explicit hierarchy, mission, etc. An institution also has everything a social group has—human relationships!

Social relationships are, and will always be, important, even in an institution. You cannot be doing your best work if you hate your coworkers! Those emotions, and the effort to deal with them so you still function at your job, consume cognitive bandwidth! And on the other hand, people very much seek to work with people who they like.

Lastly, I'm going to try to describe a thing that I'm noticing, and you can tell me if I'm accurate. From your social justice background, you learned that implicit bias is in all of us, and explicit reasoning is how we combat implicit bias. But then, there's this branch of self-improvement stuff that always goes "listen to your feelings" "trust your instincts" and it's head-on colliding with the systematic effort that you've made to not discriminate against people. Does this sound accurate to you?

Going through the points in order:

I am under no illusion that genuine community building is easy, nor that I can provide the comprehensive stack. Still, it seems useful to have a north star to guide your strategy as you look around for marginal gains that you can achieve, and ways to shape the community to be more generative and convival. The same way that people become more mazey in mazey organizations, they become more community-oriented when they are put in good communities and invited to contribute. To mangle Peter Maurin: it is not enough to do good on a personal scale, the important thing is to make the kind of society where it is easier for people to choose goodness.

Acknowledging that such a task is difficult, I think the more interesting questions are:

(1) Does Berry's definition seem like a useful guide, or are parts of it outdated or obsoleted, or simply not a good fit for our specific scene? I lean towards thinking that it's still valuable. I enjoy individual rights and freedoms very much, but a valuable part of that freedom is being able to slot myself into and contribute to a community of my own choosing, instead of the one I was born into.

(2) What parts of the definition might work at cross-purposes with each other? For example, my part of the community is very econ-brained, and our version of a community economy is going to seem more structured than some other mutual aid groups I've been part of. Auctions and cheerful prices and bets are very not on the table for many other communities that practice mutual aid. And I like the increased sophistication here! But might that cut into, like, the spiritual wellbeing angle in some illegible way, and should I care at all?

(3) Seeing as there are finite resources and a finite amount of time to dedicate to the venture, what parts of the definition should be prioritized, considering the shape of the scene as it currently is, and the ways that it is evolving?

And yes, related to our agreement that we should avoid doing things we find annoying, one more major consideration for me is: how do I ensure that the community that gets built is full of people I like, and thus want to continue making events for?

When I say I'm suspicious of "just trust the vibes", what I mean is something like "my vibe sonar is good at detecting people who are sparkly in the moment and much less good at detecting people who are long-term good for the community." I am genuinely not that good at detecting that latter thing!

True, sometimes there is just an instinctive good feeling between you and a new person, and you become really good friends. But sometimes you're like "man, I really don't know about this" but you give the new person the benefit of the doubt for a few months and maybe have an awkward conversation or two with them, and then after that they become just as wonderful as the first person to talk to.

And this isn't me being self-effacing. When I interview job candidates at my day job, I follow a rubric and make myself go through all the questions, even though I have "a good feeling" about some people that makes me want to skip past all the formalities. And the candidates I feel good about then sometimes fall flat on their face at later questions, and I'm glad I followed the rubric even though it made me feel like a dork in the moment. People genuinely aren't very good at vibe checks, and this is what the good version of DEI solves for; it protects the organization as a whole by checking the implicit biases of the HR department. You heard it here first folks, I'm going to go full woke and DEI the Canadian rationalists.

And this impartiality is important, because what I'm aiming to do in Toronto is going to be more institution-shaped than friend group shaped. This means that the stakes are higher, but the payoff is too, if we can do something good.

And, well, not to be cute, but I learned just as much about implicit biases from the website less wrong dot com, which purports to teach people strategies on being less wrong, as I did from my time in the SJW trenches :P

You're right in that if I try to be maximally inclusive and ignore the vibes completely, that would also be counterproductive. It's just that, ironically, I don't think vibe checks are very useful for ensuring that the vibes are good? It might be a skill issue, but if I don't have the skill, I don't have the skill and can only route around it.

Where do you think we agree, and disagree? And what general advice do you have, as someone who's organized in a big city before?

Okay, I have a better understanding of what your concerns are, a few things come to mind.

I think "vibes" is an overloaded term and I will discard it for the rest of the discussion. It doesn't seem helpful in clarifying what the underlying thing we're talking about here.

On trust, there are different degrees and different shapes of trust. Roughly on a spectrum, "this person I just met claims affiliation with institutions I like" is less than "I went to school with this person and they seem fine" is less than "I have worked with this person and know how they work under stress" is less than "I've been friends with this person for years and have witnessed them at their worst moments." In terms of shape, "I would trust this person to never intentionally deceive me" and "I would trust this person make good judgements on my behalf" are very different. You have already mentioned this in your example from your day job, I think you can generalize this: come up with your own trust taxonomy, as a framework to quantify it.

how do I ensure that the community that gets built is full of people I like, and want to continue making events for?

For each marginal member of the group, I think you can ask a few questions:

• Is this person's presence a net positive or net negative for the group?
• Do I actually trust this person?
• Do I actually like this person?

If the answer to any of these questions is "no" or even "ehhh I'm not sure" then maybe it's worth thinking about how to handle their presence.

So this points to something actionable: maybe you can spend your first months in Toronto doing only coffee chats with people one on one to get to know them.

—

Once upon a time I was both a very naive person and also held the ideals of open democratic groups deeply. This turned out to be a bad combination upon contact with reality. I thought I was building a public town square, then got surprise pikachu'd when I realized that not everyone who showed up was someone I really liked!

I think there's a strain of thought that goes something like "community organizers have the responsibility to provide opportunities to help people learn how to socialize." I used to think this way, but reflecting back on it, I think this came from a confused model of personal responsibility. In a do-ocracy, the people who step up to make things happen provide a public good, and sometimes that public good gets confused with "publicly-owned utility." So many organizer slip and fall and burnout on this unfortunate slippery slope.

You are not building the town square in Toronto. No one is automatically entitled to admission to your events. They are your parties, you get full say on who you let in.

Another thought I have is that you can actively seek out people whose intellectual work you like based in Toronto, maybe get coffee with them and get to know them on a personal level first.

I want to go back to an earlier point of "what attracts people to your group in the first place?" Something that I've noticed in New York and San Francisco is that a lot of cool events are not publicized. They are private Partifuls circulated around, and the reason someone is invited is because someone already in attendance actively wants to see the invitee present.

So maybe the move is to be "illegible": use your blog as a query for people who like your blog, and only the people who you also like get invited to "low-key hangouts."

And this kind of predicates on you knowing people individually.

—

But maybe "events" is the wrong concept to think about altogether!

A thread I want to pull on is "are there people whose job is community building, and how do the pros do it?"

I saw this job posting on The Diff the other day, so I think this professional field exists:

A frontier investment firm is looking for someone with exceptional judgement and energy to produce a constant feed of interesting humans who should be on their radar. This person should find themselves in communities of brilliant people hacking on technologies (e.g. post-quantum cryptography, optical computing, frontier open source AI etc.) that are still well outside the technological Overton window. You will be responsible for identifying the 50–100 people globally who are obsessed with these nascent categories before they are on-market, then facilitating the high-bandwidth IRL environments (dinners, retreats, small meetups) that turn those connections into a community. (Austin, NYC, SF)

The first name that comes to my mind is Tamara Winter, the commissioning Editor at Stripe Press. I think her focus is more multidisciplinary than technical, and I've only been to a couple of events she's hosted, but I have a strong sense that a large part of her job is to get to know people, and it's obvious to me that she just knows everybody.

When we break it down into "what kinds of work constitute community building, "getting to know people," again, is an important component of it. When I was organizing stuff in New York I naively focused on "making meetups happen," which in retrospect was only one aspect of community building, maybe not even the most important aspect. The "facilitating the high-bandwidth IRL environments (dinners, retreats, small meetups)" bit in the job description is interesting, because it suggests that the format of the events is a variable that depends on the people.

If we read that job posting again, the very first thing it's asking for is "exceptional judgement." As an aside, I'm actually very curious about how the pros develop this skill, given that they probably push far beyond Dunbar's number.

Now that I think about it, the garden metaphor is more apt than I thought. You want to garden in this new place, it's important to first survey the soil and the climate. This also makes things much easier for you: don't burden yourself with the maze analysis, it's unnecessarily cynical as a place to start from. Just go out and find the people you like and get to know them, and see what emerges.

That Diff job posting is such an interesting object, wow! You're right that I've never actually thought about all the different components that community building entails, and all the different molds that an organizer can come in, and how they develop their skills. I've been in this one mold for a very long time.

And exploration seems important, because it does seem to be the case that organizers in larger cities struggle a lot with open meetups. And I'm sure the money gun I mentioned at the beginning isn't going to help things.

I'm admittedly sad about having to think about this, because I want to host the town square, and it's worked well for me so far. I'm used to shouting about my meetups from the rooftops and getting like three new people a year if I'm lucky.

But a group being open and inclusive is only valuable if the group is worth being in, and it sounds like if I want to build a worthy group, I must pivot; my current playbook will simply not result in a good culture if I try to deploy it in a large city.

One of the other big-city rationality organizers described their meetup group to me as "an open door, somewhere out of the way", and I really loved that description. It's what I'd like to do too: I don't want people to stumble in without knowing what they're getting into, but I also wouldn't want to go too far in the other direction, and keep it exclusive to people who manage to actually get on my social radar via other means.

If my work continues to be meetup-shaped, it sounds like I should keep it semi-closed for the first few months to ferment a robust seed culture, one that can bounce the people who don't be a good fit away. But I would still like to open it up after that, ever so carefully.

Perhaps I can keep it super exclusive, and then make an IRC channel that's open between 1 and 2am every third Sunday of the month where people can queue up to pass a rigorous interview to join, like the process for getting into certain private trackers if you don't have a guy on the inside. Just kidding! Unless...?

...But I'm dancing around the point you're patiently making, over and over again. What you're saying is that I really need to actually think about moving away from doing open meetups, at least in part. That's a little hard for me to hear, because I love hosting open meetups! I love designing ones that are silly or generative or useful, I love finding readings that pair well together and curating sets of discussion questions. I love blocking out meetups six months at a time, with an eye towards getting the ratio of different kinds of meetups just right.

But I think I can learn to love other things too, and I appreciate the heads-up that this is a thing that I should try to do. Let me think. I'm looking forward to being in a place where there is a stupid amount of events and activities on offer on a regular basis, and it might not be that hard to invite two or three people that I think would get along well to any given outing. I'm looking forward to being in a city where many more really cool people live, just because of the sheer size of the population, and where it's even more of a waste if I don't up my cold email and my warm introduction games.

And my group here has gotten quite large in recent years. In the first few years, I'd worry a bit if fewer than four or five people showed up, and feel a bit like a failure. Now I look forward to every meetup where everyone can fit at the same table, and take part in the same conversation. And if I want that smallness, maybe it's not that much of a leap to organize small events deliberately?

But I wouldn't have no open events, and I'm sure you agree that zero open events would also be a failure mode. In the end, do you think we're roughly on the same page?

I remember talking with rationality community organizers from medium-sized cities, and quite a few of them told me that their meetups were like a friend group and they just hung out at each others' living rooms. KWR feels like a cozy friend group too! You and I literally met at a meetup hosted at Sean's living room! But organizing in a large metropolitan area is a different kind of work, yes.

When I graduated and moved to New York for work, the cultural shock hit me pretty hard. The New York metro area had 30 times the population size of the Kitchener-Waterloo area, and being a destination for type A go-getters from around the world, people just behaved quite differently! The kind of small Canadian town niceness that I took for granted just did not exist anymore. Learning how to read people, how to leave good impressions, and how to navigate the complexity of a large metro became quite important. To be clear, I did met a lot of wonderful people in New York, who made New York feel like home to me. But New York is overall a high-paced stressful place with its own social norms. Though perhaps Torontonians are nicer than New Yorkers :P

Oh, this actually ties back to something that you'd asked me to riff on earlier, "I think how people behave is the product of both who they are and the incentives given by their environment."

We've both read Priya Parker's The Art of Gathering, and one of the points I remember from the book is that the curation of attendees really mattered. When I read that book, I was still running public meetups for the OBNYC mailing list (already over 1000 members at the time) following their existing tradition of public meetups, so I didn't really have the opportunity to apply many of the lessons from that book. But you get to do this greenfield project, so use your many degrees of freedom to your heart's content!

Something good about the KWR meetups is that it's a group of regulars, with new members trickling in. Having the majority of the meetups being regulars, and controlling the rate at which you introduce new people, is good. Again, I didn't have such luxury when I was in New York, and when I found myself among people who I didn't know very well, it became hard to play the role of an organizer as well as I'd hoped.

Lastly, I want to say a bit more about the dynamics of inclusion. There are people in the community whose personality can be a little abrasive at times, but they are fundamentally kind people who make up for it in other ways, like being funny or having lots of brilliant insights or leading cool projects. I have found myself nonetheless valuing the presence of these people, even if I need to occasionally push back on them. Then there are people who are genuinely taxing to interact with, the cost of including them in the community social fabric is high enough to drive away the people you actually want.

I think a well-functioning group usually has some capacity to tolerate the first kind of friction. But that capacity is like a savings account of some sort, its existence depends on people intentionally banking it over time, and it can be depleted if not consistently replenished. In general, you don't want someone whose presence cost more than what the group can handle at the time, depending on how much the group has in their "social support reserve". From this lens, large, open communities structurally have an expiry date, and the evaporative cooling effect we've seen in many communities or subcultures almost feels inevitable.

Thank you for inviting me to this discussion. I'm very, very excited that you're moving to Toronto! Looking forward to seeing what your garden looks like :)

Me too :)

I'm really glad that you were open to doing this, and sharing your hard-earned advice. I'd hate to be the last in a long line of organizers that burn out of organizing meetups in big cities, and I feel like I have a better sense of how that happens now.

Thanks for chatting!