Ever since reading this article by Ben Hoffman I’ve started noticing and seeking out Interesting Conversations. Like you know how sometimes you find yourself in an object-level conversation and you and your partner are both learning and sharing information and doing novel intellectual work together? It isn’t purely one person teaching another, it isn’t that y’all are debating, it isn’t that you feel the conversation is high-value in some other metric like “wow this person is revealing they are cool and i want to know them”. It’s a fascinating conversation that makes you want to look off into the intermediate distance so you can focus your thoughts better. You’re really thinking and being challenged, and get to do the same for your conversation partner.

I’ve started seeking this out (I did not used to), and boy it’s kinda nice. People will say things that surprise you and make sense. They’ll have been thinking deeply on a topic you also think deeply about. They’ll give you new analogies and lenses for understanding the world, and they’ll ask questions that expose flaws in your model. It’s just super delightful.

I’m not very good at getting these interesting conversations and I’m very new to it, but here’s my thoughts so far:

  • Start conversations about things you yourself are actively thinking about and developing beliefs on. If you’re super into urbanism and have Opinions about urbanism, it’s easy to have an opinion-sharing / belief-stating conversation about urbanism which is not that interesting. But if there’s some new development in urbanism you’ve been thinking about that you haven’t made your mind up on, that’s likely to be fruitful (because you have deep background knowledge but are still exploring).
  • Accept that you have to prevent or manage new people entering the conversation. It’s actually shocking how quickly a conversation will be devastated by someone merely physically joining the circle:
    • They will take things on a tangent interesting to them.
    • Someone will try to include them by asking their opinion or by moving to a tangent interesting to them.
    • They will try to offer insight but just not “get it” and fuck up the conversational momentum. No judgement here, it’s hard.
  • It seems hard to return to your interesting conversation after it does get derailed. In theory you can just ask for what you want: “Hey I actually really wanted to talk to just Apollo right now about dancing, I was having a very interesting converation, Apollo do you want to keep our focus on what we were talking about before?” to rerail it which is Correct and Good but also I think a lot of people maybe can’t handle even such a soft form of rejection. So preventing people from joining in the first place is good, like going on a walk (except walking can degrade your intellectual ability, it’s a salesman tactic) or finding some nook and having closed/intimate body language.
  • I fully believe that you the reader are capable of having such fascinating conversations. Everyone has things they think deeply about, sometimes they’re just very unusual like “I think a lot about the stickers you see everywhere but most people don’t notice in Pike/Pine in Seattle” or “I’m trying to figure out of it’s good to study yourself intensely and constantly analzye yourself”. But it doesn’t have to be uncommon to be interesting, AI safety, nihilism, or relationships can obviously be fruitful fields to discuss. The point here is that everyone does contain this interesting-ness, it can just be hard to find and get to work.

That’s it.