Dan Wang emailed me with some interesting additional hypotheses regarding the question of flaking that I raised last week:

I liked your piece on flaking. When I moved to New York, I found that flaking declined dramatically. So I think that any piece that talks about flaking in SF has to explain why it happens less in NY. Here's what I'd offer:

  1. SF is made up more of tech people, who like to spend long periods of time on their own, and aren't often customer-facing. NY is more sales driven, and that creates a norm of better social habits.
  1. SF has greater marginal costs for transportation. Most trips are Ubers; in NY, you hop in the subway, which doesn't require fiddling with an app. Also in SF, the transportation times have higher variance, which puts you on better grounds for being late even with the best of intentions. On the margin, that understanding makes it easier to make excuses.
  1. SF has many more markers for status than people in NY. I have seen people pull out their number of Twitter followers, as if that means something, when they're arguing a point. Connections matter more in SF, but it's harder to compare that than the more straightforward measure of income. All this to say that people in SF feel that they can get away with flaking out more easily.

Overall, I prefer NY so much over SF, for many reasons including this.

My response:

That’s a fascinating parallel to NY. Since I’ve only lived in the Bay Area, I don’t have much of a reference, but I’ve always had the sense that flaking was more prevalent here than comparable metros. Interesting to hear that intuition confirmed.

All those points seem right, especially #2. When making plans it’s easy to forget the transportation costs, but when the day comes you realize just how much of a pain it’ll be to get across the city to Inner Sunset or wherever. This drives (pun intended) a lot of desire for remote work, too. I "flake" on work all the time. Some mornings I wake up and on a whim decide to tell my manager that I’m going to wfh that day just because the idea of trekking 30 minutes through poorly maintained sidewalks sounds so unpleasant. To be clear much of my work really can be done remotely and this behavior is acceptable and widespread in engineering (I’m not slacking on my employers’ expectations), but it’s still weird.

I’d add to #1 that a lot of jobs in the tech industry, especially in software, require long bouts of deep work. However, it’s not always easy to plan for when you’ll be able to sink into that state. Quite often I find myself getting into that flow at 4pm, and it makes me want to just work through the night until I’m through with the task because it’s hard to get back, so I’ll often cancel evening plans when that happens (or at least be tempted to). Sales/customer-facing roles don’t have this dynamic nearly as much.

For #3, I don’t think I’ve ever heard someone pull their Twitter following as a point in an argument. Where have you seen that? That’s so tasteless that it’s hard to imagine.

The point about status symbols being less straightforward than a simple measure of income is really interesting, and one that definitely displays itself in my own personal interactions. In my social group, I’m much higher status in some ways than certain friends and far below in other ways with those same people. Each of us focuses on the thing we’re "good" at, so we generally feel of equal or better status than the other person. You can kind of pick your own measuring stick, whichever one makes you feel happier at the end of the day. On net I think this is a good thing. Seems to lead to more diversity (in the broader sense) and more interesting economic/cultural outcomes than if you focus on just income or any other single measure. But it makes sense that this would also lead to more flaking—everyone thinks they’re higher status than someone else, and this breakdown of the hierarchy means that flaking can come from either side and is not just unidirectional.

Brian Lui also responded with some interesting thoughts:

I think the prisoner's dilemma is right, and also there is some sort of status thing going on: if you are powerful, you can flake more. Then people who want to appear powerful imitate them and soon everyone is flaking. I didn't think about the technology explanation, but that totally makes sense. I am not sure how the culture is like exactly, but maybe it isn't that electronic communication is fungible with in-person, but that it's more of a substitute? Electronic is much better at creating some facets of connections, mainly ones based on thinking patterns, shared knowledge, values. But much weaker at others that fall in the general category of 'chemistry’.