(I wrote this about a year ago, so parts of it might be out of date; I'm not much involved with OBNYC anymore.)

Context

Overcoming Bias NYC, the rationalist meetup in New York City, has for the last several years had a system of rotating month captains, who each volunteer to take responsibility for scheduling meetups in a given month. Before we adopted this system (in 2017, I think), there was already a tradition of having a meetup every Tuesday, but this ran into some difficulties:

• During some periods, there'd be diffusion of responsibility and sometimes the weekly meetup would fail to happen, since no-one took it upon themself to organize one (or there'd be a meetup but without a topic, which tended to result in worse meetups than those with a pre-announced topic)

• During other periods, one de-facto leader would do almost all the work of making sure the meetups happened, which resulted in the organizer being potentially overburdened, and the meetups being overly reliant on that one person.

The month captain system initially worked quite well, in my opinion, and is still going, though lately it has been faltering due to a lack of people willing to volunteer for the role.

I've been Month Captain a few times in the early days of the position, and once recently. The rest of this post will consist of a description of what I do in that role.

This post is descriptive, not prescriptive

This post is not intended as a claim regarding whether this is a good way to approach about the role of OBNYC Month Captain, nor a claim as to whether being OBNYC Month Captain is a worthwhile activity. It's just a description of what I did, not of what I think people should do.

Goal

My primary goal as Month Captain is to cause there to be a meetup every week, (unless there's a very good reason to skip a week). They're on Tuesday by default, but changing that is fine if there's a reason for it.

Ideally, they should be

• Good

• About a rationality-related topic

• Announced at least three days beforehand

  • But announcing things more than a week in advance can confuse people
  • I aim to announce Tuesday meetups on the Friday before, but this is allowing some margin for error
  • Posting a reminder about a day before the meetup is also helpful, or at least seems to increase attendance

Also, if anything comes up that someone in OBNYC should clearly handle, but there isn't anybody in particular on it, I think the Month Captain should take point on getting it done or finding someone who will - the point of the role is to counteract diffusion of responsibility!

Process

At the start of the month:

Confirm with the residents of the group house that usually hosts the meetups that the place is available.

• At the time of writing, I've been told that we can assume availability for Tuesdays and only need to check for other days of the week, but if you're reading this years in the future the situation might've changed

Pick some meetup topics

• I don't need all of the meetup topics picked out at the start of the month but it's useful to have at least a few of them

• Strategies for getting meetup topics, in the approximate order I attempt them:

  • Holidays

    • As a Month Captain, I like it when there's a holiday since it fills one of the meetup slots without me having to do much work. I'd want to check in with the person who usually runs a given event unless they've already announced it.

    • March: Pi Day

    • April: Rationalist Seder

    • June:

      • Tau Day

      • Maybe a Summer Solstice beach or park trip. Unlike the other holidays listed, there isn't someone who consistently takes responsibility for these, so it might fall to the Month Captain. I can copy the plan and announcement from a past year if I don't have a better idea

      • We don't have a tradition for Moon Landing day but maybe we could

    • September: Petrov Day

    • December: Solstice and Megameetup

• Meetups someone else has already volunteered to run this month

  • If they haven't decided on a date, I get to allocate it, usually to the soonest unfilled Tuesday they're okay with.

• Meetups I want to run myself

  • Usually I can come up with about one of these, but how to do so is outside the scope of this post.

• Recurring meetups

  • Look at the meetup history spreadsheet for things marked as 'Recur?' and see if it's been long enough since last time. If so, they're usually easy, since I can copy how they were done last time.

Send out an email listing what's provisionally planned so far, and asking for people to come forward to run meetups for the remaining weeks in the month. This can be mostly copied from a past 'Call for meetups' or 'Meetups for <month>' email if that makes things easier.

On an ongoing basis:

Try to come up with meetups for any weeks not already filled.

A mixture of topics is good; while I don't stick closely to this, I think with 4-5 weeks to work with, I'd look for about one rationality skills one, one AI one, one on some other specific topic of interested, and one just-fun one.

Some additional options for meetup ideas that that I won't use at the start of the month, but might try for weeks that remain unfilled:

• Look at the Eternal Meetup Brainstorming Thread

  • If there's something that someone expressed interested in running eventually, I can reach out and ask if they'd be down to do it this month, or if there's something I can run without too much prep or expertise on the topic, I can just do that

  • If someone has a good idea and is only available in a particular week it can displace a recurring meetup or one that I came up with, but usually this isn't necessary.

• Meetups I don't want to run myself

  • My goal is to have a meetup every week. If no-one else is preprared to run something, and there's nothing I want to run, it's time to ask myself if there's something that I don't want to run, but am capable of running. Such as, perhaps...

• Game night

  • If nothing else pans out for a given week but there hasn't been a board game night yet this month, we can just do that. I disprefer it to other options because it's not a rationality-related topic at all.

• General hangout

  • This is the fallback fallback option. If I have to resort to this, I would not consider my captainship a success. But it's good to know that there's a basically okay way to not succeed.

Each Friday

Send out the meetup announcement, or make sure the person running it does so.

• This can happen as late as Sunday and be basically fine, but I aim for Friday.

• Ideally, it should be done on both Discord and the OBNYC mailing list, but of the two, the mailing list is more important.

Each Tuesday morning

Send out a reminder about the meetup.

Midway through the month

Ask for Month Captains for the following months, unless that's already been handled.

Near the end of the month

Ask for month captains for the following months, if nobody came forward the first time I asked.