prompt: “How people maintain thought, like holding it in their head, writing it down, tweeting, storytelling. How to optimize for the most interesting thoughts being remembered”

I’m going to focus on the “how to optimize for interesting thoughts” bit. The first thing I find myself thinking is, is there any particular thing you need to do to ensure that interesting thoughts are remembered? It feels to me like interesting thoughts should be likelier to be remembered simply because they’re interesting – ie when you feel that a thought is interesting, you should feel some increased excitement around it – a sense that it might have some positive consequence somewhere. It’s like receiving a good hand in poker – you light up a little. At least, that’s my experience.

How DO you optimize for interesting thoughts? I’d like to think that that’s what I’ve been trying to do for most of my conscious, thinking life. Life is precious, and if we can’t guarantee that we’ll be constantly happy or constantly pleased, we can at least try to ensure that it’s mostly interesting. What is interestingness? Where does it come from? How do we seek it? Can we create it out of thin air?

I find myself thinking that interestingness is something that’s almost stumbled upon rather than actively pursued. Part of this is because interesting things have to be a little not-obvious to be interesting. If it’s too obvious, it’s not that interesting.

Another thing about interestingness is that it’s a very… connected… thing. Interesting things imply other interesting things. Once you have a few interesting facts, a few interesting ideas, perspectives, concepts, models – you can apply them to other things, see how they play with others. A while ago I was fascinated by the idea that “jokes exist in social contexts and perform social functions” – this idea came from someone else, I didn’t come up with it. But once I encountered it, it gnawed at me, and I found myself starting to consider all my other ideas and experiences through that lens. It’s one of my favorite experiences to have – when all the other thoughts and ideas in your brain rush to meet a new idea, and it’s a party in your head.

I think there’s a relationship between interestingness and familiarity. When something is too familiar, it becomes less interesting – not because it’s somehow intrinsically uninteresting, but because the way you’re looking at it is stale. You’re not really considering everything about it – rather, you’re thinking of it in a low-resolution, simplistic way – like how you don’t need to think about your daily commute to work. If you’re not careful, you can live your entire life that way; just passing through. So if you want interestingness, it helps to seek out the unfamiliar. For me, everything is connected, so I’ve found that even doing something like going to a different place or waking up extra early (or staying up extra late) can provoke interesting thoughts about completely unrelated things.

Interestingness is about surprise. Surprise is about expectations. So in a way the search for interestingness is about the search for surprise. Keeping track of things that surprised you is a good way to keep your mind open to interestingness. A quote that’s been on my mind is, “if something that happened struck you as unbelievable, it’s because your assumptions about how the world works were wrong”. And it’s always interesting to discover the ways in which you are wrong.

There’s a quote from Bertrand Russell: Everything is vague to a degree you do not realize until you attempt to make it precise. Your model of reality is imprecise to a degree you do not realize until reality itself comes crashing through in ways that you didn’t anticipate, and couldn’t have anticipated.

I find this Russell quote endlessly interesting, which is why I remember it. It was a quote that my boss would bring up several times in several contexts, and it always seemed relevant. Over time I learned to internalize it – this idea that when you say you want something, or that you’re going to do something, there’s always a vagueness there.

Interestingness is a function of curiosity. What are you curious about? What are some things that you don’t know, that you wish you knew? I’ve been procrastinating for a long time on an essay about electricity. Everything is endlessly interesting if you stare it at closely enough, and ask enough questions about how and why it is the way it is. I’m looking around me right now, I see a bottle of moisturizer in the corner. What’s up with that? Why is moisturizer a product that exists? Do humans need to be moisturized? Evidently it’s not necessary, because I don’t typically moisturize and I get by fine. So why does the product exist? Why is it in demand? I find myself wondering how much of skincare routines are really just bullshit marketing. See, now there’s a whole quest of interesting learning and knowledge down that path! Or I could switch and look at something else – there’s a bottle of water. Why do we bottle water? Who started it? I’m typing this in a web browser – how does THAT work?

These sort of trivia-esque curiosities are effectively infinite – you can spend your whole life pursuing them. I think there’s a class of interesting that’s slightly more compelling than that – and that’s the class of interesting thing that has a real potential impact on your life. I try to tweet a little bit about everything I find interesting, because I don’t know in advance what other people will find interesting. And it’s been interesting to see what other people find interesting – my tweets about marriage and relationships seem particularly popular – and I think that’s because everybody’s invested in getting better at their own relationships, and just at understanding human relationships in general. We are social animals, and that goes deep.

I think simply deciding to seek out interestingness in your life is a huge first step to take. And then there’s a bit of project management that follows: how are you going to develop your interestingness muscle? I think a lot of people feel a certain pressure to be interesting in a very specific kind of way – and I think that misses the point completely. That turns interestingness-seeking into a chore, another hoop that you have to jump through, another sort of status game you have to play. The real interesting (ha, this whole thing is so meta) thing to do re: interestingness is to wake up to your pre-existing curiosities. What have you already been interested in, your whole life?

A good way to figure this one out, if you have social media accounts that you post on, is to go through your old posts to see what you were posting. Going through my Instagram, I found that I have a habit of taking pictures of odd bits of infrastructure when I see it – like bad bus stop and overhead shelter design, for instance. It made me realize that I’ve actually had a long interest in that sort of ‘interior architecture’ (?), in how spaces are arranged and designed. And that makes me realize that I would actually enjoy books about that sort of thing, and read them out of interest – not because it’s something I think other people would think I’m cool for talking about.

I think Tiago Forte has been tweeting recently about how the best thing to do with this sort of knowledge accumulation process is to discharge it outwards in the form of projects and outputs. Twitter is a great place to do this. Just literally tweet whatever you’ve been learning and seeing. I think it’s always interesting to see how other people think. What are you considering? What are you concerned about? What are you confused about? You might not find your own confusion particularly shareworthy, but actually other people’s confusion can be quite illuminating. And you never know, somebody might come along and say something to you that surprises you in a certain way, maybe even solve your confusion for you. And even if they don’t, you might make an interesting new friend!

[This is a double vomit and I’m wondering what to do with the last 600 words – I had something I wanted to do here – I think I want to articulate a sketch of my ‘philosophy of interestingness’]

As I get older (and I might change my mind about this again over time, maybe in my old age in particular), I find myself more interested in things that seem likelier to have consequences on my life. When I was a teenager, and still in school, and then in the army after that, it felt like “real life” was mostly locked away from me still – like I was in a tutorial zone of sorts. So I was mainly interested in sort of abstract, big picture ideas and grand philosophies and things like that. I still have an interest in those things, but I’m no longer so interested in broad ideas like “what is value” – at least, not out of the blue anymore, not in such an abstract way. I’m more interested in things like, what can I do right now, today, that would put me in a more interesting place in the coming months and years? Who are the people I could and should be meeting, getting to know, building relationships with?

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I’ve said before that part of what I’m trying to do is to build a thread of thread of threads of interesting things that I can share with my friends. This was a goal I figured out along the way. As a kid I just wanted to… make games, write books, make science, contribute to the world in some interesting way. Along the way I found that I was accumulating a lot of random snippets and notes that didn’t seem to have any order or structure to them. This was a very frustrating experience. It’s actually pretty crazy to me that I have over 50,000 tweets – and most of them were probably only seen by a small handful of people at a very specific moment in time, never to be seen again. This is why I love twitter search and I love the reply/threading function. I am so grateful for this, actually – I don’t think it’s an exaggeration to say that my experience with twitter threads has changed my life. It’s actually changed the way I think about information. The realization I had in conversation with a friend was that the real problem in a lot of situations is a lack of threading. Too much information is fragmented – there are too many separate, disparate things to make sense of.

The cool thing about threads is that it takes many things and turns them into one series of things. When you search for something, you’re creating an on-demand thread of results. What this means is – if you start taking notes with the intention of having them be threaded with other similar notes, you then greatly simplify your note-taking by adding just a a little bit of complexity. Sometimes I get people asking me things like, how do you keep track of all your threads? I don’t, really. I don’t have a specific system of recall or tracking or whatever. I’ve just trained myself, organically, naturally over time, to start seeing each new piece of information as something that has threading potential. What do I add this to? What does this remind me of? If I’m thinking of saying something about something, have I said something similar about something else before? Can I thread it to that? This allows seemingly boring and mundane things to become part of bigger threads that become interesting by the virtue of being compared to other things, related to other things.

When I look at my own word vomit project now, I find myself thinking, oh goodness. It’s so poorly tagged. It’s so poorly catogorized. I have so many old vomits to look through and “process”. But realistically… I don’t think I should beat myself up about it. Done is done. I just need to have a better process moving forward. I mostly just need to focus on whatever I think is most interesting at any given point in time, because that gives me the necessary emotional energy to forge ahead.