41. Henrik Karlsson - Strolling Through Life’s Labyrinths

·Writer
Henrik Karlsson - Strolling Through Life’s Labyrinths

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Description

Henrik Karlsson (Substack, X) is a writer and essayist. His newsletter, Escaping Flatland, explores attention, agency, relationships, and the inner life of making things. He is one of my favorite essayists, and I spoke to him previously on Dialectic 19: Cultivating a Life that Fits in Spring 2025. We met again in Copenhagen, this time on video.

Our first conversation focused on designing your life iteratively and relationships. This time is about the messiness of creativity and problem-solving. We circle a central theme of navigating through the woods of confusion when you are—and must necessarily be to grow—lost, and trusting yourself to reach clarity on the other side. Henrik walks us through how he (and so many of his favorite artists and thinkers, from Brian Eno to Charles Darwin to Ingmar Bergman) smashes apart his mental models in pursuit of seeing things more clearly. Or at the very least, offering up something new.

He also challenges my praise of boredom, describes how a ballerina finding balance in her body mirrors what creatives must do, likens desire to the energetic discovery of wandering (or dérive, like past guest Cyan Banister has spoken about), explains why the best art is like a Jenga tower, and reflects on what he believes in; Henrik’s humanity is on display. He challenged me to think much more ambitiously about the risks I take, the ways I am holding on to faulty models of reality, and how living richly is simply a matter of perspective.

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Timestamps

  • (00:00) Opening Highlights
  • (01:28) Intro to Henrik
  • (04:05) Thanks to Notion
  • (05:58) Begin: Attention, Boredom, Predictability, Aliveness, and Dérive
  • (14:52) Confusion and Clarity: Mental Balance, Breaking Mental Models, and Making It Through the Woods
  • (31:37) Henrik's Notebooks, Personal Constraints
  • (40:54) Introspection as Subject, Not Object: Nick Cave, Rick Rubin, and Attending Outward
  • (46:56) Creative Risks, Constraints, and the Labyrinth: Eno, Von Trier, Cage, and Herzog
  • (1:03:47) Agency, The Right Kind of Risk, and What Else Is Possible
  • (1:23:29) Desire: Trusting Excitement and "Galloping Down the Street"
  • (1:30:44) Why Good Ideas Come from the Edges and Keeping the Space to Sit in Your Ideas
  • (1:44:58) Physical Space and Isolation
  • (1:51:19) Jenga Towers: Why Great Art Has Space and Spits You Back Out
  • (2:01:30) Conviction, Belief, Navigating Murkiness with Firmness and Openness
  • (2:15:54) Short Essays and How Reading Is Like Running
  • (2:22:27) What Love Is Like and Befriend Those We Read
  • (2:29:18) Grandfather Nils and a Final Reminder
  • (2:40:49) Thanks Again to Notion

Links & References

Transcript

(00:00) Opening Highlights

(01:28) Intro to Henrik

(04:05) Thanks to Notion

(05:58) Begin: Attention, Boredom, Predictability, Aliveness, and Dérive

Jackson: (5:59) Henrik Karlsson, here we are. We're back for round two in the flesh and on video. It’s nice to be with you. We are not in your home, I should establish right up front, so you are not obligated to any of the aesthetic choices. Although, I think this is a fun room to be in.

Henrik: (6:17) It is. It's an old mill, and I do live in an old mill.

Jackson: (6:21) So it's almost right spiritually. Wrong island or wrong landmass, but the right corner of the world. We'll take it. We're back in Copenhagen. I want to start with two not obviously related ideas. You have said somewhere that in English we spend attention, in Spanish we lend attention, and in Swedish, as I understand it, we are attention. Hopefully I don't have that totally wrong, at least directionally. You also tweeted recently a couple of things I liked. First, the most useful piece of writing advice you can squeeze into three words is, "Don't think, look." That's Wittgenstein. So much bad writing comes from people moving words about on the page instead of staring at the real thing and then adjusting their words to fit. Then you also wrote, in a piece where you're reflecting on the ways that children lose the magic: "When children learn to draw, they tend to make more and more interesting images for several years until around age five, when they learn to be boring. Most people never learn how to draw anything interesting again. This tends to happen in all domains of our lives. We figure out how to do things well enough and then get stuck." As I reflected on your writing, you actually come back again and again to what I might call cultivating the feeling or experience of being bored. You come back to boredom and specifically the notion that boredom is important in developing attention. So my slightly cheeky first question is: how does practicing boredom keep us from becoming boring?

Henrik: (8:20) I’ve used that phrase, the importance of being bored, before. I saw it in your notes, and instead of thinking about the word "boring," I think it might be the wrong word because boring might feel like a bad feeling. I'm saying more under-stimulated, meaning you are supposed to be not externally stimulated. If you remove external stimulations like rewards, status, and YouTube videos that keep you activated, you will feel bored at first, perhaps. Eventually, because we are curiosity-driven animals that have rewards inside of us to seek out new stimuli, we will start to generate that internally. We'll start to daydream, or we'll start to pay attention to the flowers around us, or we'll be curious about and start researching or writing something. Removing stimuli gives space for those slightly lower-tuned stimuli that come from inside to bubble up. Boring is, in a sense, being predictable. If you can determine what I'm going to say next from what you've observed of me, that would be boring. The more you're steered by what comes from the outside, the more predictable you're going to be. The more you're generating your own decisions internally, that’s often a source of surprise. If you attune to that over many years and build up a richer sense internally, that will be a source of surprise. That’s why you end up being more interesting. But being not boring or interesting feels like it's for other people. It's better to think about it as making you feel more alive.

Jackson: (10:48) I like that you've taken issue with both my uses of being boring and boredom. I had a conversation with Cyan Bannister, and the first time I ever met her, we talked about boredom. She said something along the lines of, "I'm never bored; I try never to be bored." We were debating over this because I think we were having a disagreement that wasn't really a disagreement. This kind of boredom leads to all these things coming in. It's actually more like space. Cyan uses this word that you also use, which is dérive. This kind of not totally aimless but semi-intentional drift captures the same thing. I'm calling that boredom, which is like meandering, walking, or just sitting and wondering and daydreaming. To your point, that is actually about letting all kinds of things in that are going to surprise you.

Henrik: (12:03) It's interesting. I love the interview with Cyan; she is so interesting and not boring at all. I was in Spain recently with my kids in Malaga. The first day we were there, I had some plans. It was just me and the kids because Johanna hurt her leg, so she was in the apartment. The day after, I had to entertain the kids in the evening again and I didn't have any plans. I told them we were doing a dérive.

Jackson: (12:40) That's better pronunciation than mine, by the way.

Henrik: (12:43) I don’t know. My French is... I’m also winging it. The eight-year-old asked, "What’s a dérive?" and I said we’re just going to go out from the apartment, look around, and you’re going to get to pick the most exciting direction we can go. We’ll go until we can’t see anything more, and then you decide again. It was interesting to notice how alive they became when they got to do that. It’s a labyrinthine city, so we were going down back alleys, into construction sites, and finding all these nooks and crannies. It made us much more alive than when we were going to more exciting places. Instead of saying "I'm going to go here," I would stop every few minutes and ask where I actually wanted to go now. The streets we got to were probably less interesting in some objective way than the cool caves or the beach, but we were more alive to those places because we had to attune to ourselves to figure out what would be most interesting. The kids just started galloping down the street; they came alive. I felt the same. You see it in the kids more because it's in their bodies, but we all have that sense where you almost dance down the street when you take the time to attune yourself.

(14:52) Confusion and Clarity: Mental Balance, Breaking Mental Models, and Making It Through the Woods

Jackson: (14:05) It is a state of attention. In the Robert Irwin biography, he, Turrell, and a guy from NASA go into a sensory deprivation room and sit there for eight hours. It is not even a water tank; it is just dark. They sit in there for eight hours, and then they walk out. They are prancing down the street looking at flowers, basically tripping, because everything is so vivid. It is marvelous how something as simple as saying, "Kids, we’re not going to wander around without a plan; we’re going to dérive," results in really looking. This goes back to Wittgenstein. Maybe the painters know it best: just look and really see. Look and really see, and you will be quite surprised by what is actually there. I would like to talk about something you’ve written about in different ways quite a lot. Most recently, you described it as mental proprioception. You wrote: "My job as an essayist consists to a large extent in putting myself in the right state for the thoughts to come out right." That is something you come back to over and over again. There is a lot else happening that can distract me from my curiosity or, even worse, that I can mistake for curiosity. For example, I get another kind of positive, motivating feeling that says, "If I write this, my readers will be pleased." Staying fully centered in curiosity through an entire essay is perhaps as hard as feeling that you are holding your body exactly right to execute a pirouette. I often, without noticing it, tip over into writing what is popular, and then I stumble.

Henrik: (15:55) I wrote that about a month ago, and I stumbled last week. It is very hard to do. I have been struggling with my brain for the last two weeks, wondering why it wasn’t working. I was feeling all this resistance, and it wasn’t fun at all. Two days ago, I decided to put the thing I was working on aside—even though it felt like a very good and important essay I had made progress on—and work on something no one cares about at all. All of a sudden, everything came loose. It turned out lovely and was so easy. I realized I had tripped myself up thinking the essay I was working on would be a big, important essay. The weight of it was almost—

Jackson: (16:49) What I hear in this is that it is about balance, more so than leaning one way or another.

Henrik: (17:02) It feels like putting the weight in different parts of my body. It is very tricky to talk about and sounds almost like woo, but the felt sense of it is that my motivation, or where I am writing from, is in a different part of my body. Maybe I am too low in the body. When I get it right, there is a certain kind of nimbleness, lightness, and playfulness. Like the kids galloping down the street, I get this fluid movement in my body. It is very closely related to posture, stance, and balance.

Jackson: (17:51) One of the things that comes up over and over in your writing about other people is an obsession with how people disassemble and reassemble themselves. Another way of putting this would be leaning into the confused space. This shows up most in the notebooks and private writings of artistic, scientific, or mathematical people. I know you like Grothendieck, Ingmar Bergman, and Tarkovsky, but there are other versions in Herzog and Knausgård. I recently read the Steinbeck letters from when he was writing East of Eden, which is another version of this. You also reference Newton and Einstein as they were reinventing things that were already known. You call it a building-up ability to perceive the evolution of their own thought. I see this as wading into the confused or unbalanced space, to steal from the earlier metaphor. What is the benefit of this? Why do you try to confuse yourself or move into spaces of not totally knowing or being sure?

Henrik: (19:19) Maybe I can get at it with an image. Let’s say you’re trying to make a mosaic, fitting tiles to a strange shape. If you only have square tiles and the shape you are trying to fill is round, if you just put them in, you are going to make a square. You can’t make it round that way. You actually have to break the tiles. The smaller the parts you break them into, the more perfectly you are going to be able to fill that shape. I think the same is true with our mental models. We have endless mental models for all situations, and they are a bit like square tiles. When you get a new situation, they might apply a little bit, but if you apply them straight off, they won’t fit perfectly. If you get into that confused state, it is like you are breaking your pre-existing mental models—the tiles—and you end up with a mess of small shards.

Jackson: (20:26) Debris.

Henrik: (20:28) That part scares most people. It is very overwhelming and cognitively taxing to be sitting there thinking, "Five minutes ago I understood this, and now I don’t understand anything." People try to escape from that. We have all sorts of inbuilt desires to reach cognitive closure.

Jackson: (20:50) We probably just see everything in the world as a square shape or a square frame.

Henrik: (20:55) That is what we end up doing. Confirmation bias is the classic example. You say, "Oh no, my square is actually correct," and then you just find things that confirm that. Or you get angry. There are all sorts of reactions. Darwin made a marvelous observation. He said he has to write down everything that disconfirms him—everything that doesn't fit his mental models—because he will forget them. I think that is true of everyone.

Jackson: (21:25) I misread that when I originally read it. I didn't totally catch the importance of that. It's actually your mental immune system rejecting the things that don't fit. He is specifically writing down the things that he doesn't like.

Henrik: (21:41) Exactly. Those things that don't fit in or confuse him, his mind is very good at filtering. All our minds are very good at that.

Jackson: (21:49) It bounces off.

Henrik: (21:51) We have a tendency to want to protect our squares. In cognitive research, they talk about knowledge shields. As you're going through life, you're having to construct all these mental models to navigate and make good decisions. You have to model the world in order to make good decisions, and that's costly. It costs energy to reconstruct and make these models, so your brain is incentivized to make them only good enough. You don't want to understand and see the world correctly; you want to see it well enough that you can manage. When they are good enough, your brain is going to start to filter stuff. You converge on a mental model which is not the correct understanding of the situation, but it's good enough. When we get to that point, you stop taking in new data. Everything new that just doesn't fit gets thrown off. That's why it's a knowledge shield, because it shields you from new information. A lot of work when you're doing expertise training in the military is finding ways of breaking these shields. How do you make sure that you break the understanding of someone who thinks they understand the situation, so they end up confused again? They end up breaking their tiles. Once you get the tiles apart, that is a first step toward piecing together a better model. Then you have to break it again.

Jackson: (23:31) There is an element that I think you've written about. When you've done the initial work of breaking everything up, you're sitting there with your pile of shapeless debris at the rock bottom of understanding. There is no coherence. I'll read one more thing and then I'll ask the question I was going to ask, which is Knausgaard on what he calls "sub-Bergman." He says in order to create something, Bergman had to go sub-Bergman to the place in the mind where no name exists, where nothing is as yet nailed down, where one thing can morph into another, where boundlessness prevails. The workbook is this place. In it, Bergman could put anything he wanted. The entries he made there could be completely inane, cringingly talentless, heartrendingly commonplace, intensely transgressive, or jaw-droppingly dull. This was, in part, their purpose. They had to be free of censorship, in particular self-censorship, which sought to lay down constraints on a process that needed to be wholly unconstrained. What all of those notebooks seem to get at is something along these lines. Using your metaphor, it's the person sitting with all the broken pieces. What does it look like when you've done that work to start to gradually put these pieces together and fill in the circle? That is a very cognitively and emotionally uphill experience.

Henrik: (25:16) It is very demanding. I talked with Michael Nielsen about this several years ago, and he said something that helped me understand this and get the right stance around it. I was complaining that when I was working on my essays, they would be good and then they would gradually sprawl. At that time I was afraid and would try to stop them. I felt like if I just kept going, this was going to sprawl endlessly and fall apart. He said if it starts to sprawl, then you're halfway there. That was very important for me because I admire Michael's work a lot. To have someone whose work I admire tell me that this thing which felt like everything falling apart was progress was helpful. I'm lost in the woods, and he has been through these woods many times and the good stuff is on the other side of it.

Jackson: (26:33) It is so painful though.

Henrik: (26:34) The one I wrote about Bergman and Grothendieck was the first one where I went through the entire woods. Johanna and I worked on that for three months. It ends up being a very simple piece because that's what happens on the other side of it. You end up with something quite simple again, usually.

Jackson: (26:56) The circle is as simple as the square, perhaps.

Henrik: (27:00) That can be humiliating because people read it and think it's obvious, but I have spent months getting there. There can be a temptation to shy away from that because I want to keep it complex so it looks smarter.

Jackson: (27:15) Much of the best writing is the kind of writing you're nodding along to, saying, "Yes, this is it." It can seem easy to write, but what it's actually doing is giving you the words for something you've felt or acknowledged but didn't know how to express. It's almost a version of this. That's why so much simple writing can be so elegant. Maybe you don't get quite as much credit for it because some people will be like, "I've been saying this," but that is the work that's inside there.

Henrik: (27:46) It might be fun to think about that particular essay because it started out sounding smarter than it ended up. My first draft was about the idea that our identities are interfaces. Interfaces are this thing between you and the outer world, and how you arrange that interface is a complex idea. I wrote this piece about it, and my wife Johanna looked at it and said she liked that one line where I said being bored is important. I had to throw out this entire complex apparatus of theory I had built and just take this line. I remember feeling that the idea that boredom is important is just so obvious. To build up from that to something deep and interesting, I had to read a thousand pages of Grothendieck's notes and 40 years of Bergman's notebooks. It was an extremely long process to end up with something that is in some ways obvious. How do you build up from that?

Jackson: (29:09) When you're sitting at the bottom, it's almost like you're the kid who's broken all the Legos apart. You're sitting in your pile of broken pieces. My feeling is similar to your comment about feeling like you've spilled over. That is not only cognitively wearing, but it's an emotional low point. If you're halfway through a project, it's emotionally hard, too.

Henrik: (29:33) Two things have made that easier for me over time. That project, an essay called Cultivating a State of Mind Where New Ideas Are Born, was three months of sheer terror. It was a baptism of fire where I learned to write in a new way. The thing I did wrong there was that I had the outcome in mind. I was clenching. I wanted this to cohere. Instead, it's a little bit like being lost in the woods. If you're clenching and panicking and needing to get out of the woods now, it's going to be a terrible experience. If you're instead thinking, "I guess I'm in the woods. I don't really know where I am, but it's kind of beautiful here," you can stroll around and notice things. If you trust that you'll end up on a path, it can be easier. Unclenching and realizing there's no deadline on this helps. When things fall apart, you have to trust that it can take time and it will end up looking like something completely different. You have to let go.

Jackson: (30:52) It's not seeing the thing you were hoping to see. It's being open to seeing something else.

Henrik: (30:58) Exactly. You have to really let go. That helps. The only other thing that helps is to go through the woods a few times because it becomes validated. The first few times I went through the woods, I felt there couldn't literally be anything on the other side because it was just confusion and terror. Then, lo and behold, I ended up with much more clarity and understood things that were important to me. I ended up writing an essay I liked. Doing that a few times changed the emotions around it.

(31:37) Henrik's Notebooks, Personal Constraints

Jackson: (31:33) Confidence is the memory of success, as my friend Jason likes to say. Do you keep notebooks in this way?

Henrik: (31:40) I do from time to time. I write several hundred thousand words of journals in a year. Some months I'll write 50,000 words where I'm endlessly sprawling. I have them all. I think maybe if I have time, I should edit some of that together and publish it. It could be a fun companion to the essays, showing the process behind the work, the life, and the frustrations. I find them very valuable. As I write them, there is a sense of being lost in the moment. I give myself a few days a week where I'm allowed to wander in the woods in the notebook. I'll just read randomly and let things fall apart without any pressure. I'll go back to them a few months later and see that it was really good. I'll find these clearings, but I can't pressure myself to see them at the time because then I'll clench. I just go around, and when I'm done, I look back and find these beautiful essays. I was rereading some diaries I wrote two years before I started the blog. I remember that as a dark night of the soul period where I hadn't found my way yet and hadn't learned how to write. When I was rereading them, they were much better than I remembered. I had actually written, almost word-for-word, two or three essays that I published three years later. I had already done them, but I didn't notice it and didn't have the confidence to see it. That wandering is important, so now I try to be more persistent about returning to those wanderings. It's like being a child and then editing—writing drunk and editing sober. It's like being a kid going around in the woods and then returning a few months later as a connoisseur picking out the best of it.

Jackson: (34:16) I totally relate. I write far less than you do, but I have a writing group I go to. I'll write things one Wednesday morning and feel like I'm in the wrong mood and it all sucks. A week later, I'll look at it and realize it's pretty good. I'm such an unreliable narrator of the present. Writing itself is a practice of doing this often for the experience of living. Unless I spend some time meditating on an experience and ideally writing about it, I have to trace the grooves once or twice for it to really work. There is something about having to encode. The more times we encode something, the more it gets to work. You don't delete these notebooks. There's some element in your brain saying that maybe somebody will read these notes if you're successful enough. One point you make about the notebooks is that it's the one place where Bergman isn't being observed. I'd like to tie it to another point you make about constraining oneself. You talk about Von Trier or Vinterberg tying their hands behind their backs and finding ways to create that are deliberately constrained. Knausgaard forces himself to write five pages a day, and then eventually 25,000 words in 24 hours.

Henrik: (35:50) Let's not dwell on that.

Jackson: (35:52) That is dark.

Henrik: (35:54) Imagine having agreed to publish that also.

Jackson: (35:57) He did.

Henrik: (35:58) It's in book two of My Struggle. He's doing it in the middle of a controversy. He knows that 500,000 people, 10% of the population in Norway, are going to read this. Then he spends 24 hours writing 25,000 words about meeting and falling in love with his wife in a very intense and painful way. Let's not do that.

Jackson: (36:22) One version of this is finding ways to prompt yourself into new ways of creating or writing. The other version is considering how it's going to be observed. I'm curious how you think about tricking yourself. You wrote somewhere about spending one week writing where it all has to be deleted at the end of the week, and maybe another week where the whole point is to make it as pop as possible or most audience-oriented as possible. I'm curious how much you play with those types of things or even think about this in the case of the notebook. Is there ever a version of writing that would change if I truly promised to permanently delete it afterwards versus putting it in my back catalog of notebooks?

Henrik: (37:16) I don't think about an audience at all when I'm in my notebook. It would be valuable to publish parts of it, but as I write it, I don't think about the audience at all. If I go back and read my diaries from when I was 17 or 20, I can clearly see I was young and had hubris. I thought that this was going to be read, though hopefully not. If I read my diaries from around when I turned 30, there's been some shift in my stance where I can feel this person no longer thinks anyone's going to read.

Jackson: (38:04) Are you writing to yourself in the future?

Henrik: (38:08) Yes, exactly. The big change that happened for me in 2019, which was a precursor that led to the final breakthrough with public writing, was that I started indexing my diaries. Once a week I would go through and I would number the pages and then I would do an index on the front page. I would write, "On foldup two, I talk about Ivan Illich," and then also "On foldup 18." I would list them.

Jackson: (38:39) This is the re-encoding again, the retracing.

Henrik: (38:42) The idea was to make sure that I would go back to it and enter into dialogue with my past self and not have all of these thoughts wasted, so that they would be searchable. What happened when I did that was that I became my own audience. Prior to that, I almost never reread my stuff. Then I started rereading; it became real.

Jackson: (39:06) You knew the audience. It's really easy to write a letter because you know exactly who the audience is, but also you have extreme confidence the person will read it. If you write anyone a letter, at least if you know them, they're probably going to read it. What I'm hearing you describing is a trust of your reader to actually follow through. You got into a pattern where future you actually would go back and read it, so it made the stakes more serious.

Henrik: (39:36) I suspect early on when I did that I would go back and read things and notice, "Oh, that's cringe. I am posing." That would be embarrassing in front of the audience of myself, and so I would want to unlearn that course.

Henrik: (39:58) It's like a ballerina in front of a mirror looking at the movement of the leg and seeing the wrong movement because it’s posing or cringe. Without even thinking about it, I had that reinforcement loop which helped me get into the right pose. Whenever I write in the notebook now, I always immediately go into the right pose where I am open, creative, and willing to linger in confusion. In other mediums, like if I open the Substack editor, Google Docs, or an email, I enter into different stances. But I have, through practice, encoded a very good stance around my notebook, so I can always go there.

(40:54) Introspection as Subject, Not Object: Nick Cave, Rick Rubin, and Attending Outward

Jackson: (40:49) It's an environmental priming where you know what we do here and you're in that. There's a thread that relates to this in terms of how we talk to ourselves and ask ourselves questions. You were talking about a woman, Kellie, who is writing into Nick Cave for advice on how to be creative. She's struggling and blocked: “Another way to make a distinction between Nick and Kellie is to say that Cave is trying to figure out what his voice is trying to say right here, right now, while Kelly wants to hear her voice tell her what is true about her across time. But they are both introspecting in the sense that they want to know what a voice inside them says if they block out the expectations of society or the audience. Cave is more modest than Kellie here. He is asking not who he is, but who am I in relation to this song, this book, this tour? (Is there potential in this song? How can I open it up? What does it want?) Those questions are hard, but not as hard as "Who am I?" and can often be solved in a few hours at the desk.” Is the secret to this productive conversation with ourselves to ask simpler questions? Or to be more specific?

Henrik: (42:15) In my own notebook, another shift happened around the same time: I shifted a lot of it away from myself. I used to use my diary to deal with my frustrations. I still do that for a little bit, but I started to attend outwards. My notebook was filled with reflections about things I read, things I saw that my kids were doing, things that happened in nature, and conversations. I started to attend outward. I made a note about that recently where it's almost like you can know yourself as an object. I think that was what Kelly wanted to do: "What kind of person am I? Who am I?"

Jackson: (43:09) And almost drawing a narrative around yourself as well.

Henrik: (43:12) And that's very complex. I have no idea who I am. We're such extremely complicated objects. Even saying what Hamlet is, or a short book, is very hard, but we're like that times a thousand. We are going around having different experiences and thoughts every moment, and trying to define down what that is is very hard. It's hard to have a good understanding of yourself as an object. A lot of people try to turn toward that, and that can just be confusing and navel-gazing. When I try to attune to things outside of me—to my kids, a book, or nature—I am connecting to myself as a subject. I'm connecting to myself as a person paying attention. What am I noticing here? What am I getting frustrated with, or what am I curious about? All of that is information. You can understand that subjective perspective of yourself. If you look at someone like Rick Rubin or Nick Cave, they have extreme confidence in their subject. They know themselves as subjects really well.

Jackson: (44:35) They know the pieces in the circle. They know the debris more than they are looking for the boundary shape.

Henrik: (44:43) Yes, I think those things.

Jackson: (44:45) Another way of putting it would be that they are seeing the pixels deeply. They have an incredibly high resolution on the pixels, but they are less concerned with what the holistic image is.

Henrik: (44:56) Yes, they do. It is like with someone like Nick Cave; it is not clear at all where he is going. Obviously, music is very important to him, as it has been for 40 or 50 years. The way that music evolves and the different kinds of films, books, and art projects he does along the way—he is making his small ceramic figurines—all of that is very drifting. If you were trying to understand Nick Cave as an artist—let’s say you were his management and you were trying to determine what the Nick Cave brand is—you would never suggest doing porcelain figurines of the devil.

Jackson: (45:46) It is telling that the world today is trying to put ourselves into brand-shaped, let alone algorithm-shaped holes. We are trying to make ourselves legible. The modern Internet is about making yourself legible in a way that is cohesive enough, small enough, and contained enough that it can be replicated externally. I think it is telling that there is some kind of external pressure to be that way. Maybe less with Nick, but people love to draw some guru box around Rick Rubin and then poke fun at it. I think Rick just doesn't care because he is just like, "I like these pixels" or "I like these little shapes."

Henrik: (46:28) The understanding that people have of Rick from the outside is probably very deep divorce from what he is from the inside.

Jackson: (46:40) I think they are observing him far more than he is observing himself.

Henrik: (46:43) The stereotypes of him just being that guru exist, but he is actually a very intellectual person and spends enormous times reading. That is not what people see.

(46:56) Creative Risks, Constraints, and the Labyrinth: Eno, Von Trier, Cage, and Herzog

Jackson: (46:54) This relates to what we were talking about at the top, which I would call a broad thing around being unpredictable. I think that extends into taking risks, agency, and a handful of other things. You say, "I have such difficulty hearing what I feel when there are strong external reasons to do something." We were speaking about that, and as a result, you need to create the space to become more unpredictable. When talking about AI, you say a language model analyzes a string of words and completes it by predicting how the text would have continued if it was a sentence on the Internet. Your job, on the other hand, is to write the least predictable thing that still makes sense. Once you learn that grass is supposed to be green, it becomes almost embarrassing to make it blue, even though real grass is often blue, as good painters learn when they start to pay closer attention to reality. My sense here is that there is being unpredictable for its own sake, which is the wrong reading of how to make oneself irreplaceable to AI. You could imagine someone just trying to be chaotic and using unpredictability as a path to getting towards where you want to go, or to the place that is right, or to a place that is ours. How do you know the difference, whether it be in a stylistic choice in creativity and writing or in a life decision choice? There would be a risk of just being unpredictable for its own sake.

Henrik: (48:38) I am going to push back on that. I do not think having a goal to be unpredictable is the way; that is playing to the audience, as if you are trying to fight the AI. It is better to orient toward what is exciting or what is alive. That is what to aim for. When it comes to constraints and unpredictability, I was thinking about John Cage and Lars Von Trier. Both do very unpredictable work and both use constraints a lot in the process. John Cage has this piece where he set up a system and used I Ching or dice to make all the decisions. The music is total chaos. The timing of the notes, the pitches, everything is decided through this random system. I find that a fun experiment, but it is horror to listen to. It can be interesting for a few minutes.

Jackson: (49:53) It is a hack. Cyan rolls dice to decide to do things in her life, but I don't think she is using it to get to a place of openness, derive, or original seeing versus using it as a way to get to the finished product. That is the difference.

Henrik: (50:13) Randomness will get you out of the habitual. It will get you to places and combinations you would have never seen before. But John Cage doesn't then apply his own taste to it. He just says the system has run its work, and now we have random chaos. That is one kind of experiment. Brian Eno is closer. He has a system that runs in his house where he has 10,000 sonic landscapes that he has made across the years. His system will pick two at random and play them at the same time in his loudspeaker. He can push a button to change into a different combination or save that combination. He is exposing himself to a lot of dissonance, but then he is applying his taste. He gets outside of his habitual space of ideas, but then he picks the ones that are interesting and reworks them into something that works. That is a difference between him and Cage. What Lars Von Trier is doing when he is applying constraints on himself is something similar. He is applying constraints that limit him from doing things that are easy and that he knows will work. He is very talented with framing. If you look at the films he made in the eighties, they look like Golden Age Hollywood. Everything is so crisp and beautifully choreographed. He consciously said he was going to forbid himself from doing all the things he is famous for and does well. He is only going to use a handheld camera and, for a period, no artificial lighting. He has all these constraints forcing him to remove all of that. But he is not just making poor films; he is acting within that realm. Now that he can't do the normal interesting things he likes, he has to go in a new direction. He actually ends up finding novel things that are not only novel but also more powerful. They are resonating with us as an audience at a deeper level. That is what matters. It doesn't matter that it is novel; it matters that it shakes us.

Jackson: (53:05) The tension here feels like he's using unpredictability as a tool to unlock more aliveness. Or maybe unpredictability is still the wrong word, but he's using these constraints. You write a lot about Eno and the ways he is really good at risking everything over and over again. You critically make the stipulation that he has upped his level of risk-taking gradually over time. At one point you say if you have a hit and can build up some savings, that is meant to fund bigger risk going forward, not keeping up with the Joneses. Am I habitually doing what I had to do to get here rather than looking clear-eyed at possibilities that actually exist now? The question to go back to Von Trier is: do we know if his films are actually better? Last time we spoke, you talked about how if you could, you'd spend a year just writing about Bergman's diary. Is that the best thing for you to work on? Is it "more love in relationships" lists, as we joked about last time? To go back to mental proprioception, it's about this balance in yourself and with the world that allows you to chase what you're alive to and be responsive. There are these hacks that the most truly attuned person wouldn't even need to use. Lars is using these constraints because he knows that his tendency will be to...

Henrik: (54:41) I think we'll start with an image again. Imagine that we're moving through a giant labyrinth, a maze. It's not even like a normal labyrinth; it's high-dimensional, going in a hundred dimensions at the same time. Inside this labyrinth, we're going to have good artworks, good essays, good startups, and good research ideas. Our job is to take the right path through this labyrinth to find the good stuff. That's what we're doing when we're creating new things. These different constraints and stances are rules of thumb for how to navigate this labyrinth. For example, if you're applying constraints, you're saying that you're not allowed to do this and that. You're blocking off big parts of the labyrinth. By saying you are only going to work in this direction, you're forced to go further down in that direction and you'll find new stuff. But I don't think we can know beforehand where in the labyrinth the good stuff will be. Sometimes going very pop, like Coldplay, works. I think Coldplay has done some extraordinary art. They have thought very hard about what the audience wants and they've optimized and gone down the labyrinth very hard in that direction. They ended up finding some good things. Others say you can't know in beforehand. If you look at Lars von Trier, it's very clear that he's always applying these rules on himself. More than half of the time, he abandons the projects because it turns out that part of the labyrinth is barren.

Jackson: (56:40) It's explore/exploit in some sense.

Henrik: (56:42) He had a project that he started in the early nineties where he was going to film for three minutes every year for thirty years. That's a strange constraint. It turned out that was a terrible film, so he's not working on that anymore. He's done many of those. You just have to try different parts of the labyrinth. I don't think there's one stance.

Jackson: (57:06) I like that a lot. The arbitrary constraints to unpredictability are one version. Another version reminded me of Steve Jobs. It's Herzog being upset about doing things the proper way. The professionals have too many preconceived ideas of how to go about things, wasted resources, and missed the light in the trees. They're worried about the makeup, and he's obsessed with the gold light. Steve Jobs speaks about this in the eighties. He's talking about how they had some way of doing accounting for hardware, and you basically flubbed the numbers because there's no way to get the numbers exact. He said that seems dumb and we should just change it. He calls this business folklore. It's the way things are done, the way things have to be done. That's another version of reasons you might not look in a certain part of the labyrinth. You come across a certain solution dilemma and all conventional wisdom says you choose door B or C because door A tends to lead the wrong way. It is about getting yourself... unpredictability almost feels like deliberately being unpredictable. Rolling the dice is a very low-dimensional way of doing this broader thing that you're describing.

Henrik: (58:42) Dice is just an example of a constraint. Herzog is irritated with the crew because they're going through the motions and doing all of the normal Hollywood stuff. He doesn't feel like that's necessary because he'd rather catch these accidents and the beautiful light that comes on at some point. That is the tile again. They have a tile: "This is how you make film." When you're dealing with Werner Herzog, the normal Hollywood tile is the wrong shape. You have to be able to break that apart and put this together in a new way. Be open to the fact that maybe we're not going to do makeup in this scene because we'd rather film the morning light right now. Be open for that because that's the right thing for his aesthetic and his ethics of film. But they couldn't because they were so locked in. They had this northern shield again.

Jackson: (59:47) If we don't get the makeup, we won't have the tile that makes this a square. And we have to make it a square. That's what they're saying.

Henrik: (59:55) They're just reapplying the same idea they have as a framework. This is how we do it; it's going to be A, B, and C. It's going to be the same over and over again. Whereas if you're going to do really good work, you have to be open to this thing right now. The film they were making in that case was a very gritty, handheld Vietnam film where it's supposed to be very claustrophobic. You don't need makeup for that. If you pay attention to the film you're making, that is not necessary. But they are so certain we're supposed to do it that way. To make good art, you have to try to be naive or innocent. This is the situation. What kind of camera movements do we need here? What kind of stuff do we need here? Don't do the habitual thing and just make the mosaic specifically for this piece of work.

Jackson: (1:01:00) How do you think someone like that? The counter-argument to this framework would be that breaking apart all the tiles every time is obviously not tenable. The more you break them, the better you get at rebuilding them. Someone like Herzog is very comfortable in the broken debris space. He's very comfortable in ambiguity. That might be a trait of someone with high agency. There's a reason we have consistency in models. Is it just about getting more comfortable in ambiguity so you can speed-run that faster? How do you know when to? Unpredictability as a goal in and of itself leads you astray. It leads you to overrating doing things from first principles. That's not the point. The point isn't to do things from first principles. The point is to find the new place in the labyrinth. Maybe it's just attunement, as we keep coming back to.

Henrik: (1:02:02) You talked about it being very costly to do it that way. That is the case, but if what we're talking about now is not how to run your accounting bureau doing the same thing over and over again, then you shouldn't apply this way of thinking. When you're filming the podcast, you probably shouldn't reinvent that every time. The focus for what you're doing with podcasts is trying to push the conversations into a better space. Around that part where it really matters, it's worth putting in that effort. If you just want to get a result fast, then use tiles. It's the same as if you're building a house and you have these floors that you just click in. It looks like a fake wooden floor and it's very fast. It's a sort of tiling. If you want to make a really nice house, you're going to have a carpenter hand-carve every little part of it. It depends on what business you're in. If you're in the business of creating new ideas for a startup, art, or essays, it's a very costly research cost. These are costly projects, but it's the only way we know how to get to these powerful new experiences, products, and artworks.

(1:03:47) Agency, The Right Kind of Risk, and What Else Is Possible

Jackson: (1:03:47) One last thing. You wrote about agency shortly after we last spoke. You had this little excerpt about Maud: "I wish I had a book that I could put in her hands. And it helps her learn what many never learn or learn too late. Namely, that the possibilities are much bigger than you think, that you can live more deeply and truly, and that you can solve almost any problem if you put your mind to it. A book about how to handle being sentenced to freedom and to handle it effectively and authentically and responsibly." You go on to talk about autonomy and efficacy as these two components of agency: the capacity to dig inside and figure out what wants to happen through you, no matter how strange or wrong it seems to others. Maybe cost is similar to risk. What is the relationship between agency and risk? Along the lines of everything we just spoke about in trying to do truly new creative things in that labyrinth, how do you think about updating your model of risk? Specifically in the Eno sense, how do you use the current success to unlock the new unknown thing versus playing the hits?

Henrik: (1:05:09) That part is hard. Our sense of self and our mental models are always a lagging indicator. They are slow to update. I struggle with that a lot because the rate of change for me has been quite rapid. I went from being totally on my own and isolated on the island six years ago. Maybe three years ago, I started to have some success, and now it's my job. When you have that kind of almost exponential change in your life, it's very hard to update. I still feel like the person I was four years ago, which is not who I am now. To get back to risk, I probably take way too little risk.

Jackson: (1:06:14) I think all of us do, almost overwhelmingly. Maybe not Elon or Peter Thiel.

Henrik: (1:06:18) Specifically in my case, I haven't updated that I'm actually not struggling with money anymore. That used to be a terror for me for many years until less than a year ago. I still think that way even though it's not true. That's making me make not the optimal decisions I could be making.

Jackson: (1:06:50) It's a scarcity mindset that is seeping in.

Henrik: (1:06:52) I'm not looking at the situation clear-eyed. I'm not noticing that the situation is actually like this. The amount of money I could invest into a project is higher now. I'm not noticing that. Because I'm not noticing, I'm actually not making the best decisions. I don't know how to actually make that update faster. Another thought that came up when you talked about risk is that it helps to think a little bit like a VC. You're making a bunch of bets in your life. Every time I'm writing an essay, I'm making a small bet. I'm betting that this will be a valuable thing for me to spend 50 hours working on. I'm betting on these conversations. It's usually the case that it's not worth doing due diligence on everything. It's a good idea to not take risk in most domains of your life so that you can play very risky in some domain. The bold, risky moves have high payoff. In order for them to have high payoff, you have to do due diligence. You have to think things through and position yourself correctly so that your experiments have some likelihood of paying off. Most of them will fail, but you want 10% of them to succeed. To do that, you have to be okay with not thinking too much about my clothes or things like that. I try to simplify many parts of my life.

Jackson: (1:08:43) I was going to say you're very concentrated. To the extent you have almost overwhelmingly concentrated on a few fairly risky things that maybe are less risky than they look on the outside, you don't have a diversified basket on a relative basis.

Henrik: (1:08:58) Exactly. You see that when Abraham Maslow did his research on people who are highly self-actualized. They are making concentrated bets in certain domains and they're not taking a lot of risk in their entire life usually. They are selective conformists. Some people who are very self-actualized, in his opinion, tend to dress very conservatively, tend to have normal haircuts, and tend to be that way in all sorts of ways because they're trying to minimize needless friction. If I'm wearing a funny T-shirt, that's going to cause some friction in certain situations. Do I really want to spend my limited amount of energy, time, and money on the friction of my T-shirt, or do I rather spend it on my relationships or my creative work?

Jackson: (1:10:00) If you keep talking about clothing too long, you're going to sound like Mark Zuckerberg. You have to be careful. I think the point is well made.

Henrik: (1:10:08) It's a point I often make about priorities. Don't sacrifice the wrong thing. What's the thing you're trying to do? Steve Jobs wore the same clothes every day because he didn't have to think about that. There was no friction. It is very simple.

Jackson: (1:10:27) There is another thing: don't get cute. If you found a thing that works, we talked about this last time. You said, "Great, you wrote a couple of good essays. That's cool. Let's see if you stick around." I'm four years into this now; you're five years into this. What about fifty years? I think about this while working on my project. I'm a year and change in, and it has more success than it had before. How wide is my aperture? Am I taking enough risk? Am I trying enough other things? Should I just keep doing this thing? I think I'm drawing a false comparison, but I'm not totally sure how to think about risk in the context of opening up the aperture to planting other seeds versus not getting cute because you found something.

Jackson: (1:11:28) Hit the ball.

Jackson: (1:11:28) Keep hitting the tennis ball.

Henrik: (1:11:31) If I think about myself and how much choice I have, I keep thinking that maybe there are some very big, very valuable things I could be doing if I just doubled and tripled down on certain things that would be very valuable for other people. I would also probably earn a lot of money by doing those things. Sometimes I think maybe I should do that, then I could have a bunch of money to donate and have much more impact, but I just can't do it. That is just a personality trait. I am someone who is seeking and trying things, but to some extent, I think it's a valuable thing to think about at times. This is a period where I'm locking down and not changing plans all the time. I am only doing the newsletter. That's the only thing I do. I don't take on any other work, so I've locked that down. But I'm keeping some aperture inside of that because otherwise I'd just rebel and quit the whole thing.

Jackson: (1:12:45) Conversely, you've talked about a world where the essays are the exhaust of the life, state of mind, or even the milieu you've cultivated. You've alluded in your writing to a world where you threw out a whole bunch of ideas, whether it's doing more investigative work, interviews, bringing people to the island, or making films. It’s easy for me to imagine a future for you where Henrik wrote essays in the barn for 20 years. Maybe the output of that is that you write a few good essays. There’s a different version of you where the world of Henrik or the world of Escaping Flatland has many more facets. I think about this a lot in terms of what I'm doing, especially as someone who has a tendency to want novelty, shiny objects, and variety. To tie it back to the earlier theme of proprioception and balance, how are you attuned to yourself regarding what to do next? How are you attuned to the ways you lean in that way?

Henrik: (1:14:02) We're very much at the edge of my thinking, so I'm going to be incoherent.

Jackson: (1:14:07) That is hopefully the goal with a little bit of this.

Henrik: (1:14:10) I'm struggling with this thought a lot. One promising direction for my personal work is that I've had a period where I've locked down very much and done my thing. To get where I am now, I had to realize this works and is aligned with what I value, so I'm just going to double and triple down on that for a few years. For the last year I've been wondering what the next step is, and I haven't figured that out. One thing that could be valuable is making sure that I put myself in interesting situations and work on interesting projects such that the essays happen of themselves. I'm trying to put myself in a situation where I free up more time. Right now, the blog is taking everything from me. It would be interesting to carve out time so that I work on the blog three days a week and the rest of the time I'm doing related work that puts me in new situations to feed the blog. I can't keep going doing what I'm doing now because if I spend six days a week on the blog, at some point I'm going to get very boring because I'm not having enough new experiences. I probably need to start making films, start a podcast, or start traveling more to feed the main thing. I'm trying to find some way of making those things work together.

Jackson: (1:16:01) You have to see that threat. The root of the question is trying to figure out what is riskier. Is it riskier to stay focused and not get distracted, or is it riskier to try all these other things and lose the plot? My reading of you is that you are very attuned to knowing that at some future point, there is—forgive the crass metaphor—almost like a tumor or a little seed of something. It’s working to do the essays six days a week right now, but you probably won't be able to sustain that forever, so you need to unfold. That's how I see it.

Henrik: (1:16:56) One thing that comes to mind is seeing it a little bit more clearly as we talk. I think I have this from Nassim Taleb’s books, maybe Antifragile, where he talks about certain kinds of jobs. If you have a normal 9 to 5 job, it’s going to look very stable, and then one day you’re going to get fired and your income is going to go to zero. Whereas if you drive an Uber, your income is going to be up and down a lot more, but you’re actually more resilient or antifragile because you’re planning buffers in your spending to handle swings. If there’s a downturn, your salary is only going to get cut 20%, not 100%. That idea applies to my situation too. I could double down on the things that work. There are book deals I could do that would earn me more money and have more impact short term. But it’s like putting all the eggs in one basket. The risk is that I’ll burn out, I’ll get bored, other people will get bored, and I’ll be locked in. It is going to look safer and more stable right now, but over 50 years' time it’s probably riskier because I’m locking myself in. Trading off 30% to 50% of my time into more diverse bets will make my situation now more unstable and my income go up and down. But it’s probably over time a less risky path. That’s my current thought at this very hour.

Jackson: (1:18:52) It relates to a finance idea: the number one thing is to stay in the game. You should keep playing the game and optimize to be able to keep playing the game, not to hit zero. I think there’s an energy or curiosity version of that.

Henrik: (1:19:10) I’ve had that thought on and off for a long time. I think I could have become a full-time writer a year earlier, maybe even sooner. But as soon as I saw that was possible, I was afraid. I feared that if I were to sprint to that goal and quit my job, I would be completely reliant on this income. That might be a terrible situation for me. It might be very stressful. I might feel very locked in and having to deliver certain things. So I consciously started to be a little bit unpredictable. I would drop my cadence or go silent for a month. I would throw curveballs and break stuff. That slowed my growth quite a lot and I lost a lot of subscribers. But it meant that I had the permission a year later. Now I know I have permission. I can go silent for a month.

Jackson: (1:20:22) It enabled you to go farther and to go longer.

Henrik: (1:20:24) Because I was afraid, otherwise I’d just be too afraid. I do already have a lot of latitude, but the question is: do I need even more?

Jackson: (1:20:37) The challenge with all of this is that it’s possible it actually was risk aversion then. Risk aversion can sit next to knowing yourself well enough to know that you have to go slow to go longer. I’m trying to build up an attunement in myself to better identify fear and risk aversion when that’s all it is. When you’re an analytical or introspective person, you could talk yourself into a lot of things. The Silicon Valley investor advice—to just go faster, do more, be more agentic—generally tends to be pretty good. But the challenge then is that mentality broadly doesn’t tend to build the most enduring things.

Henrik: (1:21:36) It’s interesting with risk aversion. What I noticed in that situation was that I know that I am risk averse. I have to be because I am the sole provider of my family. I can’t take those kinds of bets. Knowing that and planning in enough buffer and enough creative freedom probably makes you realize how risk averse you were before you had a family.

Jackson: (1:21:59) What do you mean?

Henrik: (1:22:04) Maybe I’m projecting or assuming, but my assumption would be in the same way that I think I don’t have that much time. If you spend a day in my life, you would be laughing about how much time I have. I suspect there’s a similar amount of risk that you can take when you’re 25 and don’t have a wife and kids. It is so dramatic. If you were in your 25-year-old shoes, you’d be like, "Oh my gosh, dude, you’re not taking enough risk."

Jackson: (1:22:05) Maybe. I think I was pretty calibrated when it came to risk. My problem was more a lack of knowledge and a lack of good habits. Maybe I could have taken even more risk. I took more risk then than I do now, but I definitely squandered my time away. That makes me fry now. I had so much time and I accomplished almost nothing. Now I have a bit more time again. But for many years I had no time at all and I had to get up at five in the morning and write. You’re sitting there at five in the morning and you’re super tired. Why didn’t I do this before I had kids?

Henrik: (1:22:36) One little thing this week: a friend asked me about what I want, specifically regarding desire. I’m curious how you think about that as it relates to attunement in the specific sense of really wanting something. It caught me off guard in my inability to answer her question. We just spent the last 20 minutes talking about how some people really want money and they get money. Maybe they’re not fully aware of how bad they want that.

(1:23:29) Desire: Trusting Excitement and "Galloping Down the Street"

Jackson: (1:23:29) I like the word desire. I think that word does a lot of good work here. At least for me, this doesn't apply if your goal is to make as much money as possible. This only applies if you’re a weird person who wants to write essays. I find that it’s very important that it should feel like desire. It should feel bodily. It should feel like my kids when they are galloping down the road.

Jackson: (1:24:44) This is it.

Henrik: (1:24:44) It should be. I treat myself all the time. The reason I talk about these things is because I find them hard. I have a bunch of very intellectual friends who are always reading hard books. Sometimes I’ll tell them I’m going to do an essay with all my reflections on The Brothers Karamazov. Then I stop working on it. I realize I’m actually trying to impress my friends and I’m not excited about the book. I’m actually excited about things that feel light, open, and playful, like galloping down the street. In order for me to do good work in my line of work, I have to get back to that thing. It’s very hard, and I miss it all the time. I get these ideas that sound like good ideas, and they are projects that I admire from afar. I’d love to read that essay or that book, but it’s from the head. I can calculate that it’s a good thing to do. Sometimes I think that I want that, but the thing I really want is the thing that makes me feel playful and loose in my body. Those things are almost embarrassing in some sense. I like the word desire. What is making your blood boil a little bit? Often those things are hard to explain. The ideas that I get in my head are usually better elevator pitches.

Jackson: (1:26:41) What should I want to want? That is the meta thing running here that can crowd out the desire.

Henrik: (1:26:46) I’ll give an example because I’m talking in the abstract. I was reading Solvej Balle’s Book 6 of On the Calculation of Volume.

Jackson: (1:26:56) This is the repeating day.

Henrik: (1:26:57) Exactly. I was reading Book 6 and there was a segment where she was talking about Plato. There is a dialogue with Socrates where they talk about how, in the past, time used to go in the opposite direction. I started imagining what that would be like, living your life backward. You would go around visiting different funerals and notice how sad you were at them to find your friends. The sadder you got at a funeral, the closer the person was to you. Sometimes you would have to try to find some parents if you were living backwards, because eventually you would have to climb back into a woman who would carry you further into the past. This is a very strange thing, but I got very excited about it. It’s not an obviously good idea. In my line of work, it's like, what is that?

Jackson: (1:27:58) It's a new part of the labyrinth that you've never been in before, though.

Henrik: (1:28:01) I noticed that idea for some reason. Now I give it space, but it was just a small thought that happened for three minutes in my head. I got excited and felt a lift. I can’t explain it. It’s not an obvious escape in the Flatland essay. I don’t know where it’s going. Maybe it will end up as nothing, or it might end up as something completely different that doesn't look like this at all. But there is some seed there. I’m trying to more and more trust that excitement. If I travel down this and let it go into confusion—because I don't know how this idea could work or what it is trying to do—I might end up with a story from my childhood. It would be something completely different, but I'll trust that this is an interesting part of the labyrinth.

Jackson: (1:28:53) It's a nice complement to aliveness, which is a word you use so often in talking about writing. You talk about it like a lightning bolt in your body. It feels like those two things are operating in a similar part of our inner space.

Henrik: (1:29:10) I guess aliveness is the catchphrase for that. But today, I’m feeling galloping down the street. It’s better because it’s more visceral. Aliveness is a bit of a dead word.

Jackson: (1:29:23) I don't think I need to ask. It’s funny with things like this. There’s something so true it’s pointing at, and yet if you use the same word too many times, it gets dulled. It’s important to find new ways to hold it.

Henrik: (1:29:40) There is a lovely apocryphal story about a mental institution in Copenhagen. It was called Mental Institution. At some point, they started feeling that was a little bit old-fashioned, and they wanted to change it to Psychiatric Hospital. They had this beautiful carved stone in front of the house where it said Mental Institution. At a meeting, someone had the brilliant idea to just flip the stone over and write the new name on the other side. They went out, flipped the stone, and then it said Idiot Asylum. Words will get destroyed. There is this continual loop of having to rename this place because whatever name they picked for it would be dragged in the dirt.

(1:30:44) Why Good Ideas Come from the Edges and Keeping the Space to Sit in Your Ideas

Jackson: (1:30:40) That applies to a lot of things. I'd like to talk a little bit about remoteness or space. I’ll start with a quote from Ingmar Bergman's workbook, April 5, 1955: "As you know, I am afraid of emptiness, desolation, and stillness. I cannot bear the silence and isolation. Death. Emptiness is a mirror turned to your own face." And this is from you: "Almost everything that makes up our world first appeared in a solitary head. The innovations, the tools, the images, the stories, the prophecies and religions. It did not come from the center, it came from those who ran from it." Why is some form of isolation so foundational to being creative?

Henrik: (1:31:32) If we're going to get technical, and I’ve decided we should, when you have a larger population—as you have in the center, in the big city, or in the mainstream—they are going to filter harder. It’s like a bandwidth pass. It is very hard to get an idea to catch on in a big population because you have to make everyone believe it. It has to be really good.

Jackson: (1:32:01) You have to reach a critical mass.

Henrik: (1:32:02) It’s very hard for that to work. The good thing is that the mainstream will filter the bad ideas. The mainstream has a fairly reasonable understanding of how vaccines work, but they also don't have a perfect understanding either. Big corporations filter ideas very hard, so they kill the best and the worst ideas. Smaller populations filter less hard because there are fewer people to convince. If you go into a Discord or a group chat, the ideas that can float around and get accepted are going to be much more extreme in both directions. They are going to be worse and better. When society is functioning well, it is organized in a hub-and-spoke form where you have the fringes. In the fringes, you have research labs or solitary researchers having ideas where there is no filtering and the ideas are allowed to be extreme.

Jackson: (1:33:06) It’s like pace layers.

Jackson: (1:33:07) Similar idea.

Henrik: (1:33:08) Exactly. It gets passed on to a scene where it gets filtered a little bit and improved. Then it gets passed on to bigger and bigger populations. Almost all good ideas need to start out in the fringes. If they were in the middle, they would be censored or wouldn't catch on. We can all be in the center and the fringes at the same time and go back and forth. But we need the fringes. We need to protect these spaces where people are allowed to become radicalized and allowed to have extremely bad ideas.

Jackson: (1:33:41) The Internet, by the way, is in theory really good for this, but in practice it is actually bad.

Henrik: (1:33:48) It’s hard to tell. Nadia made an interesting point in her book, Anti-Mimetics, about the evolution of the Internet. Until 2016, there was a gradual centralizing force towards social media, and then that blew up in massive, crazy ways. Since then, you've had a gradual trickle into group chats. What’s happening is supercharging memetic evolution because people are connected to the main population on Twitter, but they are taking ideas into group chats. There is a very rapid evolution of ideas in this radicalized setting, and then they are spawning back out. We are getting an amplifier of natural selection. In a laboratory, if you have bacteria and you want it to evolve certain characteristics, you accelerate the rate of evolution. You can change the topology of the groups. If you put everything in a big blob in the middle, it's going to be very slow for that group to adapt. If you instead make these hubs and spokes where you have these smaller things on the sides, that structure is called an amplifier of natural selection. If you structure it precisely right, you can dial up the speed of evolution. It could be argued that what's happening on the Internet is that with group chats, we've dialed up the rate of evolution by having these evolutionary breeding lagoons. You have the most bizarre mutations in group chats, and then they are getting spawned back into the feed. It goes back and forth into different group chats. That depends on how much time people spend in group chats versus the feed. I find that to be a very interesting idea. By thinking about the structure of our networks and altering the connections in a deliberate way, you can steer the evolution of ideas. You can make a network that is producing more ideas faster by just changing who talks to whom. We could do some interesting things with that on the Internet. Now we just have these big blobs, but if we could create these more structured spaces, it would be powerful.

Jackson: (1:36:25) Are you not building something that could be that? You talked about a blog being like your little room or your little cafe on the Internet. As you build, maybe it starts off as a little book club and as it scales it becomes more of a cafe or a church. There are various coalitions of personality-led clusters. There's the Venkatesh Rao part of the island, the Henrik part of the island, Nadia, and so on.

Henrik: (1:37:01) I think so. There are many tools for this like Discord and Substack. I use the chat with the people who are behind the paywall. I still think we lack the proper tools, but I can't figure out the correct shape for this because it's a very tricky thing. You want to have hierarchy. There's a hierarchy around my blog where I am the alpha male and I have much more reach. I can affect that community much more than anyone else. We need better tools for creating hierarchies because people are going to contribute at different levels. The problem with an open comment section is that it tends to drag the quality down. Certain people reach out and want to connect, but they might not be the ones who should be front and center. When they start commenting because they are trying to reach out and don't have any friends, the people who could contribute more feel like it's amateur hour. They aren't going to contribute there, so they email me instead. I have the interesting conversations over email instead of in the comments.

Jackson: (1:38:27) You host an event and pull the actually interesting people into a back room afterwards, or the after-party.

Henrik: (1:38:33) There has to be some structure where the main conversation is held by the people who are having the high-quality conversations. We need a hierarchy. It's probably going to be controversial for some people that you're ranking people, but it's important that you can control the flow of information. We don't really have the right tools for that, or it's not easy to do.

Jackson: (1:39:02) It's quite interesting that we have a very good structure for the vertical creator-audience relationship and for wide-open, horizontal spaces. There's very little resolution in that space between the vertical and the horizontal. You wrote about air gaps in time between publishing work. You said, "I suspect many of my friends who write and publish rapidly are short-changing themselves. They generate text filled with hidden doors and move on before they've opened them." Another metaphor you use is that your drafts are rooms you go to when you want to think. When you publish, you throw away the key. You said to keep the key for a little while. Say more about that.

Henrik: (1:39:50) It's that forest of confusion again. When I write the first draft of something, ideally it is just notes to myself in my journal. That is just me exposing what I already think. It's basically a tide. The next step is addressing the hidden doors. Once I have that thing on the table, I'll notice open questions or things that do not fit. If I just publish it and move on, I'm not actually going to get the real value from that draft. The real value is when I see it isn't making sense and I need to do more research or talk to a specific person. I start smashing it to pieces. It's in that process where I'm actually updating how I think and getting into closer contact with the idea.

Jackson: (1:40:55) My assumption was that what you described makes sense. A piece is 80% there and you could publish it, but you have an itch. My assumption was that you have things that you know are good and you are going to hold them. You talk about holding things for a year, which is probably closer to the previous example.

Henrik: (1:41:20) That part is also true. There is something about my brain that when I publish something, it is gone from my life.

Jackson: (1:41:33) Which is that metaphor, right?

Henrik: (1:41:35) That sucks a little bit because it means I can almost never rest on my laurels. Whenever I write a good essay, I am putting in hard work and finally shoot something, and then I publish it. Now I have nothing. That is the feeling. I never get to feel like I have built a body of work. That is never how it feels to me. It always feels like I had an interesting room I was hanging out in, and now I have abandoned it. Now I need to find some other interesting room that will make me come alive. Those rooms are valuable to hold because it is nice to have a nice room that I can hang in.

Jackson: (1:42:17) It's almost selfish.

Henrik: (1:42:18) When I am in that room, I am thinking about things that are valuable to me. Those stories are putting me in a mind state where I am able to get closer to things that are meaningful in my life. If I am writing an essay about my kids, I am going to be a more present father during that project. As soon as I close that door, I would have usually become a better father than I was before.

Jackson: (1:42:55) It is like an active lens. You wrote about writing about things being like pulling the world into you. You have a lens or an aperture that is sucking in all that stuff. There is something great about that because it is being compressed and offered. I really worry if you write a book.

Henrik: (1:43:24) Why?

Jackson: (1:43:25) Because a book is this experience in a much more totalizing way. If you were to write a book, it would have to be something so foundational that you could have written fifty essays about it. I imagine something akin to a mother seeing their child go off to college.

Henrik: (1:43:48) If you spend a year or two years on a project, it is going to be a part of your life. That was when my kids learned to bike, and everything is in that book. I am not working on a book, but the funk is the core reason I write. It is a meditative practice. If you meditate, you put yourself in a certain state. The NASA people that were sitting in a deprivation tank get out and see the flowers. Essays are like that for me. If I spend time writing about my kids, I go out and notice everything about them. That is very lovely. I get to prime my own mind toward both being more present and understanding at a deeper level. The presence goes away after the project, but the deeper insight stays.

(1:44:58) Physical Space and Isolation

Jackson: (1:44:50) Priming your own mind is a wonderful way of putting why some creative thing might be worth it independent of anything else. You wrote about Joanna reflecting on my interview with Nadia. She asked if you were making a mistake being so isolated. You could be people who go to dinners and talk to interesting people. You have said elsewhere you really love talking to people. Do you get lonely now? Do you worry about the pressure of one person being so foundational to how you can think aloud? It is a lot to hold.

Henrik: (1:45:56) That is something Joanna and I talk about. It is perhaps even more acute for her than for me. If I were to be hit by a bus, we are homeschooling together and I am the sole income. Her life would be very difficult. It is important to plan for that eventuality and to make sure she has her own social network that she can rely on. That is also true for me, but it is a little easier since I naturally have a lot of connections through the writing. I have collaborators and friends. It is always good to have multiple lives to stand on. We think about this all the time. Should we be in a city? Would it be better to be surrounded with more of a scene? It is valuable to weigh how we are constructing the environment around ourselves. When we made the decision where we live now, we did not think we would ever earn any money. We wanted to homeschool, so it had to be cheap. Now we can see a path where we could actually live in a city and afford to homeschool. So we should update and ask if it still makes sense for us to live on a cheap farm on an island. Where we have landed is that it does make sense for us because of how we are wired. We like the local community, we like nature, and we like to have a lot of time on our own.

Jackson: (1:47:52) A lot of space to come back to it.

Henrik: (1:47:54) When we lived in the city, I was a yes man. I knew everyone in town. It was Uppsala, a city of 200,000, and I could not go through the city without running into someone. I was always getting dragged into cafes and parties. I cannot say no to things. There are so many exciting things and I am always talking. I constrain myself in this place. When you are in the country, you have to actively decide where to go and who to visit. You have to make it a priority. Who would I actually like to spend more time with? I like to have to be deliberate about my choices like that.

Jackson: (1:48:41) Life is a constant fight against inertia. The point isn't just to change things, but to build a habit of reevaluating. This is something you do really well across so many of the contexts we’ve spoken about. Most of us face the temptation to hesitate. We wonder if we can make a change and are hesitant to unfold and explore the possibility of something else. If we do make a change, we feel like it has to be how it is forever. Maybe it comes back to a lightness or a loose grip. It is not about a lack of conviction, but an openness to the fact that what was true for me then very well might still be true for me now, or it could change in a year. That could be true about work, where you live, or much smaller things. There is a temptation, once you get something, to just hold it and keep holding it.

Henrik: (1:49:39) I find that meeting new people is a very good way of unclenching that fist. This is especially true if they are curious, agentic people who are doing different things and are a little bit disagreeable. They can push on you.

Jackson: (1:49:58) It’s the spheres.

Henrik: (1:49:59) Exactly. It’s fun because they’re all so different. I have different people I turn to for perspectives and advice, whether they are mentors or peers. Their opinions go in completely different directions. I get confused because I always want to do whatever the person I'm talking to suggests. It is very good for me to have people saying the opposite. It blows my head open and I get confused. Then maybe I’ll try a little bit of this and a little bit of that, or something in between. I used to rely a lot on solitude for that work. Now I have the luxury of relying more on peers because I found people who can do that to my mind. Previously, the people I had access to were not priming me in the right way. They were maybe a little bit too conservative.

Jackson: (1:50:55) Right.

Henrik: (1:50:56) I would have to retreat into solitude, which might be the best thing. Sometimes I find that solitude is slower but better. Sometimes I just want to make a fast pivot or decision, and then I just talk to a few different people.

Jackson: (1:51:15) You want to cycle through the different modes too.

Henrik: (1:51:18) Yeah.

(1:51:19) Jenga Towers: Why Great Art Has Space and Spits You Back Out

Jackson: (1:51:19) I really liked that you talked about good and bad consumption and how the space theme shows up. Certain art, information, or content can be good consumption and certain can be bad. The essence of it is about how close you feel to yourself. You said that you and Johanna sometimes look at a page in an art book for ten minutes. You can't do it for much longer than that. Paintings, unlike the internet, spit you back out after a while. Despite having allowed ourselves to get completely absorbed by something external, when we close the art book, we feel more attuned to ourselves. You talk about Philip Glass and the way he thinks about composing music for films by leaving space. In many parts of the internet or a TV series, you come out of it and don't really feel super close to yourself. Other forms of art have enough space for you to put yourself into it. What are the patterns of the art that have this kind of space for you? What makes you really learn about yourself or get closer to yourself?

Henrik: (1:52:46) I think it was Empson who talked about the seven types of ambiguity. That is one way to think about it. The type of art I’m talking about has ambiguity and space. It is not reaching closure in itself. Philip Glass makes the distinction between art and a commercial. A commercial is perfectly closed; everything fits together and the message is super clear.

Jackson: (1:53:13) It’s like propaganda.

Henrik: (1:53:14) The propaganda commercials know exactly what they want you to feel. Everything is designed for a set message. They don't want you to have any interpretation.

Jackson: (1:53:24) No interpretation.

Henrik: (1:53:25) When you start removing things and creating space for interpretation, the viewer has to fill those spaces to make the artwork meaningful. Famously, Shakespeare’s plays are often based on historical things that actually happened. If you compare the history to what he writes, he often removed the motivations for behaviors. In the historical record, we know exactly why a person did a certain thing, but he deletes that. You are left wondering why he is killing his wife. When you don’t know, everyone can project different things into it. Different actors can play these plays in different ways. There is so much space for reflections and emotions to be pushed into Shakespeare's work that wouldn't have been there if we knew exactly how to interpret it. When there are things you need to fill with yourself, the way you feel it is by listening inward. You ask yourself why you think he killed his wife. You notice the way he turned his head and think he was lying. The thing you are attuning to there is yourself.

Jackson: (1:54:54) Yeah.

Henrik: (1:54:55) Ambiguous art also spits you out because it is hard work. If you have ever read Shakespeare, you have to stop at every other line and fill things in. You wonder what a word means or how to interpret it. It is exhausting to read ambiguous work compared to propaganda or Twitter where there is less of that. It has a twin capacity: it will spit you out because you get tired, and then you just lean back on the sofa to be with yourself. You will also be close to yourself because you have been forced to pull from yourself. That’s my read on what is happening in those situations where a piece of art or writing brings me back to myself.

Jackson: (1:55:47) I love the "spitting out" metaphor because it's a great way to articulate friction. The majority of incentives and culture today are actually incentivizing media not to have that effect. One of my favorite ideas is that reading is a collaborative act. It is more collaborative than most other mediums we spend time with today, with painting being an extreme example on the other end. No two people read the same book because I have to put myself into it. Perhaps a truly remarkable novelist is good at projecting something very specific, but usually it works the other way around.

Henrik: (1:56:27) With writers like Shakespeare or Kafka, the skill lies in removing.

Jackson: (1:56:36) Yes.

Henrik: (1:56:38) It's almost like that game with the blocks—what is it called?

Jackson: (1:56:44) Jenga.

Henrik: (1:56:45) A good novelist can pull the Jenga blocks and build them very high. You wonder how it can even stay up.

Jackson: (1:56:55) Yes.

Henrik: (1:56:56) But it somehow remains standing.

Jackson: (1:56:58) It's no surprise that many of the worlds we adore are the ones we can put ourselves into and imagine ourselves in.

Henrik: (1:57:03) Weak writers build very compact things with no holes in them.

Jackson: (1:57:11) A Jenga block of narrative writing.

Henrik: (1:57:13) Exactly.

Jackson: (1:57:15) I like that a lot.

Henrik: (1:57:19) There are strong incentives today to write in ways that fill all the holes—to write propaganda or obvious things. If you look at what's trending on Substack, it’s often cliches filled with fluff that reinforce what people already think. There is no space to fill in. I notice this myself. If I used the techniques Kafka or Shakespeare used—making things gnarly and hard to interpret—I wouldn't have any readers. There is a tension because I want to provide that space, but I also need to make my writing very clear and easy to read on a phone while on the toilet.

Jackson: (1:58:24) If it's going to spit you out, it needs to be very easy to get into.

Henrik: (1:58:29) The easiest way to create ambiguity is to refer to modernist poetry, but that is a constraint for me. I’m not allowed to use those tricks or that elliptical style. The challenge is writing something that is clear and easy to read on the surface—almost like a Twitter article—but simultaneously opens up those spaces. I’m not sure I always succeed, but it is an interesting challenge. Without using obscure language, I want to see if I can use simple sentence subversion.

Jackson: (1:59:14) It's about finding a way to subvert.

Henrik: (1:59:16) Hemingway does that well. He uses very simple language, and while some of his sentences might be obscure, they still create those spaces.

Jackson: (1:59:28) You’ve mentioned how the biggest topics can be the most boring to write about. The trick is figuring out how to discuss things like romance in a fresh way. It is electrifying when it works, but it's difficult because the temptation is to be either overly obscure or overly basic.

Henrik: (1:59:55) One way I think about it is like playing jazz. Jazz musicians take a classic chord progression and improvise on top of it, adding disharmonies. You can take something simple and add interesting juxtapositions and shifts. If I write about love or emotions, I might bring in machine learning because those are from different domains. If I can weave them together, I can write about each quite simply—a few things about machine learning, a few things about Tolstoy—but the way they clash produces larger resonances. I try to create these spaces using simple language by juxtaposing ideas from different fields. This also helps bridge domains. Many of my readers are programmers who might resonate with Tolstoy because I am connecting those worlds, and vice versa. It is valuable to bridge those gaps.

(2:01:30) Conviction, Belief, Navigating Murkiness with Firmness and Openness

Jackson: (2:01:30) There is a thread I keep returning to, defined by two words: trueness and conviction. In your essay on agency, the takeaway was that agency is about your values, your desires, and taking a stand. If you have enough conviction, agency is actually quite easy. At the end of that piece, you write powerfully about your daughter, Mod. You said the reason having her in your life made you more agentic was that it was the first time you experienced what it means to surrender to your values. You had idiosyncratic opinions when you were younger, but you held them flimsily. When things got hard or people disapproved, you tended to give up and do the normal thing. You wrote that if you had experienced that pressure before Mod, you would have caved in immediately. But with her, caving in was unforgivable. You must never fail her. That is such a powerful, almost impenetrable example. In cases that are perhaps less biological, where do you think this type of conviction comes from?

Henrik: (2:03:22) Conviction can come from multiple directions. For some naturally disagreeable people, it comes easily. For me, it was having children and feeling that I had to stand up and act for them. That experience provided habituation. By being forced to stand up for my convictions, I had to go through the pain of doing what I wanted to do. I came out on the other end and realized it was okay. Sometimes you need to be held by the hand or forced. It’s like joining the Marines; you are forced to do more situps than ever before, and you realize you are actually capable of it. This can happen in different ways. A startup incubator can provide similar external pressure, where the need to live up to mentors or investors forces you to do things that are uncomfortable.

Jackson: (2:04:44) It's like constructed stakes.

Henrik: (2:04:46) Having investors or having kids are different ways of constructing those stakes. Another way of securing your conviction or acting on what you believe that’s been used a lot historically is to say that if I do not do this, I betray God.

Jackson: (2:05:07) I wrote that down. You said thinking of the work in religious terms as a service to or a search for God—Bergman, Grotowski, Tarkovsky, and Pascal all do this. It might be easier to summon the awe and daring necessary to push out into the unknown and against social pressure if the alternative is failing God or a fiendish muse.

Henrik: (2:05:24) I’m an atheist, so I’m going to be very crass about what that mental move is doing. It’s hijacking our conformity bias. We have a tendency to want to bow our heads to authority. If you invent an authority which is all-seeing and all-powerful and give them your idealized values, you’re hijacking your innate drive to submit to authority or to fit in. You’re hijacking that monkey brain thing we have. One shouldn't explain that because it works less well if you understand that's what you're doing. I struggle to do that myself since I don't believe in God and would know I was tricking myself and just using God as a prop.

Jackson: (2:06:21) What do you believe in?

Henrik: (2:06:25) I believe we all have something we can contribute. The universe in itself is so extraordinary, with everything like quantum particles, black holes, and evolution. We get to come here and explore and take part in this unfolding creation. That’s so remarkable and big in itself. On top of that, because of the accident of your genetics and the place you’re born, there are certain things that will only be possible for you. There will be certain things that only you will be in a position to care for. For some reason, it feels imperative to me that you should protect and be a guardian of that possibility. You should make sure that you leave the universe a better place and act as a force toward higher complexity. When you leave the planet, if the fight against entropy has been won, civilization is a little bit more coherent. We have better theories of the world, richer relationships, and more diversity in perspectives. It would be super boring if the universe was just rocks floating in dead space because that wouldn't have as much complexity as biological evolution. You're just being the force for increasing complexity.

Jackson: (2:08:26) Is it fulfilled potential? Is that too simple?

Henrik: (2:08:30) That's a good way of simplifying it down, but not only for yourself. I am not all that important in myself. I value myself because I live in my body, but what matters more to me is this continual unfolding. With my ancestors and all those behind me, how can I play a part in this ongoing evolution dance? We’re in this big jam session. How do I make sure that when I leave the stage, the song—

Jackson: (2:09:13) The music kept going.

Henrik: (2:09:15) It kept going and was hopefully going in an even better direction because people around you had grown and were playing wondrous things.

Jackson: (2:09:22) We talked about this a bit last time, but it is being a good steward of being sentenced to freedom. You were writing about Zbigniew Herbert and ethics, talking about how ethics is care and not something an external authority demands of you. It's not a list of commands you follow. You also spoke with David Perell about this kind of hard and soft together—being open or porous and also very firm at the same time. In the Herbert essay, you said you have to see the world for what it is in all its brutality while keeping your heart soft for the beauty that makes it all worthwhile. Maybe you could replace hard and soft with bravery and openness. Does that resonate with you?

Henrik: (2:10:20) I think that's part of it. It's interesting when we have these conversations because it's all the same topic all the way through. The reason you need to be both hard and soft when interfacing with the world is that the world can be a horrendous place. Many things, big and small, are terrible, and you want to see them with clear eyes because you want to see all of reality as cleanly as you can. We don't have to think about the big horrible things, but just in your life. In a relationship, you want to be able to see the ways you are failing as a father or a husband. You want to see the frictions. You want to be able to sit with those uncomfortable things. That requires a certain hardness. It requires a certain non-naivete, a certain forcefulness and strength in facing these painful things because unless you can do that, you're not going to see reality clearly. If you're not seeing reality clearly, you're not going to be able to chart the most ethical, good, interesting path through the labyrinth. But you also need to be soft. Softness is what is going to guide you through this world. The hardness lets you see the world, but it's not telling you where to go. Softness is what tells you where to go. The risk if you're just very hard is that you become stoical and close down. You become tense and decide the world is a terrible place and you're not going to trust anyone. That's not going to help you navigate. At the same time, you have to get back to galloping down the road, being playful and soft. Those small intuitions from the inside—what feels alive and what feels good—are going to guide you where you should walk in this reality. We've talked about it in terms of creative work, but it's also true in all domains. When you're having a conversation, it's that ability to feel inside yourself when something is right. If you can tap into that, be vulnerable with that and share that, the conversation will come alive. It's the same thing as with creative work, and I think it's the same thing if you're designing a house or building a company. I noticed when I mentioned that I didn't believe in God, you got curious. You stopped, went off-script, and asked what I believe in. You were genuinely curious about that, and it felt like there was an opening in the conversation. There have been several of those in our conversation here. You want to be both hard and soft. You need to be stoical enough so you can see reality and childlike and playful enough so you can decide how to walk through that world. They are not easy to combine.

Jackson: (2:14:12) It is assertive and receptive. What I do is hard to define. I could show up with no notes and be maximally receptive. We would probably have a pretty generative conversation, and I should probably try more of that. However, I don't think we would cover as much ground. I tend to drift. I could also just come and read off a teleprompter, but all wonder comes from that marriage between the two. Everything good comes from that balance. It is about staying right in the middle of asserting and receiving.

Henrik: (2:14:56) So much of it feels like we're calling back again and again to the phenomenology of navigating in murky spaces. How much is it supposed to feel in the body? What are the rules of thumb? How are you going to put your feet and feel inside where to go? It feels like everything good talks about different aspects of those felt senses.

(2:15:54) Short Essays and How Reading Is Like Running

Jackson: (2:15:26) That is one of the primary readings I have of your work. It is something you are not always staring directly at, but you are circling around. One of the reasons I find the writing beyond beautiful, compelling, or entertaining is that it is useful. I think that is a worthy thing to pursue. I have a few more miscellaneous things. Your essays are short and very readable in a way that must be quite deliberate, even compared to other things on Substack.

Henrik: (2:16:13) They have gotten shorter. I used to average 4,000 words; now I probably average 2,000 words. That is a nice length that you can finish in one sitting. I used to allow myself to sprawl everywhere. I want to make sure each essay is its own small room. If I look at my older essays, they are actually three groups put together because I didn't feel like one was enough. Now I trust that one thing is enough. I prune my writing a lot. When I read other writers, there is often much more fluff. That can be good because it can be a way of putting you in a state by repeating the same idea from different perspectives. I try to keep it more trimmed to make it easier to get through, but also to leave more space. Most people read through my essays very rapidly, and hopefully that is a pleasant experience. I try to make them so that if you slow down and consider what this would mean if applied in your life, there is actually a lot to unpack. The sentences are written in a way that should flow very easily, but there is depth. It is that double lead.

Jackson: (2:17:52) It is the Jenga Tower, too.

Henrik: (2:17:54) You should be able to scroll through it and read it quickly, but you should also be able to sit with it. Some people have told me they have read certain of my essays fifty times. That is wonderful. If you can create something that people can come back to and see more and more layers, it is successful.

Jackson: (2:18:12) How is reading like running?

Henrik: (2:18:16) Reading is like running in that it is a skill. To be able to run, you need to build up many parts of your body: your leg muscles and your heart. To be a good runner, you have to develop your mental models and understanding. You taught me about pacing and things like that. If you are going to run a marathon, you are not just going to go out and do it. You have to become the kind of person who can run a marathon. That takes at least six months, probably several years. The same thing is true of reading and writing. A lot of people misunderstand that because they can read a little bit, and then they think they can just tackle Anna Karenina. That is like saying I am going to do a marathon on my first training run. Everyone runs too fast and too far when they start. What matters in reading is gradually building up your capacity to process words, your references, and your understanding. If you are reading Dante, there are going to be references to a million things. The poem is going to be much better if you understand those references. It takes time to build up those things to actually do it. A good idea is to start slowly and steadily, making it fun and gradually pushing yourself. Reading Anna Karenina is supposed to be very easy. It is not a hard book if you are prepared for it. When I was seventeen, I thought it was very hard to read. Now I read it and it is like a romance novel. It is very easy because I built up the capacity. I think about this more and more in all domains. I used to think you just need to explain certain ideas to people. That is a big part of why I started writing publicly. I figured this thing out and thought I should just write down how to do it. Then you realize that is not how it works. I used to write essays about how I write my essays, thinking I could teach other people that way because it is obvious to me. But the reason I can write the way I do is because I have spent twenty years becoming the kind of person who can write them. My entire nervous system has been redesigned for the purpose of writing essays. If someone tried to do what I do, it would take at least five years of deliberate hard effort. You have to literally rewire your entire brain. I think that is underappreciated. Regarding agency, people say you can just do things. But if you are the kind of person where your parents abused you and no one ever believed in you, you get intense anxiety at the thought of putting a foot forward. You can't just do things. It is going to be a very long process of rebuilding yourself into the kind of person who can just do things. But it is also a hopeful image because basically everyone can run a marathon, and basically everyone can become a good reader or writer.

Jackson: (2:22:08) You have to show up.

Henrik: (2:22:09) You have to show up. You have to do it again and again for many years. You have to not burn out by expecting too much of yourself. That kind of gradual increasing of strength and the little practice.

(2:22:27) What Love Is Like and Befriend Those We Read

Jackson: (2:22:26) I found an old draft of Looking for Alice that you linked to in a footnote. Instead, I've done it by chaining myself to someone who grew weird in ways synergistic with me. That word unpalatable is interesting. What is palatable and what is not is often a question of context. A Westerner sees someone eat a dog and feels revulsion. The revulsion isn't in the dog; it is in the context. To understand the delicacy of the dog, you must inhabit another world. That can be very hard. Maybe you figure out how to place yourself in the context where dogs are tasty, and now you're munching on one. Along comes your mother. "I've just had a revelation," you say. "Let me tell you." But all she sees is the paw on your plate. I think love is a lot like that.

Henrik: (2:23:13) I haven't forgotten that. That was cut from that final lesson.

Jackson: (2:23:18) Why is love a lot like that?

Henrik: (2:23:24) Love, as compared to infatuation, is a deep, knowledgeable appreciation of another person. You can't love someone in the Erich Fromm sense of that word unless you are so intimate with that person that you have actually looked at them and understand them. Personally, my closest relationships with people I feel the deepest love for are almost like acquired tastes. A lot of people fell in love with Johanna around the time when we met because she was very lovely in some easy-to-read ways. The important parts of her personality, the parts that I truly love now and that are the core of her, they didn't see and didn't appreciate. To really deeply love someone for who they are, you have to see them very deeply, and that requires a lot of context. It's almost like acquiring the skill of loving someone. Sometimes if you show that to someone else, it might not make sense. Take a very obvious example: some people have an open relationship because they look deeply at each other and realize they are totally okay with each other sleeping with other people. That feels very beautiful and fragile and close for them, totally respecting each other's idiosyncratic feelings. Another couple might look at that and say that seems like a very toxic way of living. Have you actually inhabited this world? Have you actually paid attention to what we feel inside when these things happen? That's an obvious one, but there are often subtle versions of that in all relationships if you're actually allowing that relationship to grow into a shape that is fitted to the people involved.

Jackson: (2:26:00) You write about authors as your friends. Authors are our friends. They are odd people who talk to us sometimes from across the grave. When Johanna and I talk, we'll say Tomas and mean Tranströmer. He is one of our mutual friends and we gossip lovingly about him. When I read the biographies of exceptional people's early lives, it feels like getting new peers. Their way of being works on me. Gradually, I raise my aspirations. Who do you feel closest to in this way? It doesn't have to be an answer for all of time, but could be current.

Henrik: (2:26:37) I always turn to different authors at different points in my life where I'm struggling with things. As we talked about earlier, I've been struggling with the next step of my creative journey. It's been natural for me to turn to someone like Brian Eno. You read his diaries, listen to interviews he's done, read his biography, and try to piece together how he's done it. That gives you some models. In some ways, it's easier for me to talk to him because of the situation I'm in right now. Not many people have been in that situation. None of my friends have. It's hard to talk about these things, but I feel like I can bounce against his experiences. I don't think I'll do the same thing as he did, but he feels like someone I can sit and talk with. I get the impression a lot of people put authors on pedestals. I see people even do that with myself, which is super weird to me because I'm obviously just a guy. It's very strange when people do that. I'll even see it in comments where people write about me in the third person as if I'm some kind of thing.

Jackson: (2:28:07) You are the dictator of the blog.

Henrik: (2:28:09) Sure I am. But it's so strange when people write about me as if I'm some famous person. I'm just doing the dishes and my kids are playing. I'm in the room. You don't need to put me up there. The same is true if you approach Dostoevsky like that. You realize they were all very human. They were all very relatable and open in their writing in their strange ways. You can really see eye to eye with them. It's very healthy to just bring them down. They are weird, they've gone through extreme things in their lives, and they are very skilled at specific things, but they're just people. They can be interesting to talk to because they have interesting experiences and they pushed further into that than many others. It's nice to just put them down here and play with them.

(2:29:18) Grandfather Nils and a Final Reminder

Jackson: (2:29:18) You wrote about your maternal grandfather who passed away last summer, Nils. Life is not a story that builds to a climax; it is a story that meanders. Every single moment in life is as worthy of care and attention as the climax of a story. What I grieved wasn't his worn-out body finally giving up. That felt good, actually; it was a relief for him. What I grieved were all the moments that were gone. Even more, I grieved all of the moments he had been alive to himself—all of the moments that no one else will ever remember. The feeling of sun on his skin. The long nights in the snowplow clearing the roads through the pine forests. The feeling, if any, of his last night when Maud the Elder held his hand and he seemed for a moment to slide out of his dementia into sleep and smile. It was the goneness of all of those moments that hurt. Are there any other moments that come to mind that you would like the world to know about Nils?

Henrik: (2:30:22) He was a very special man who meant a lot to me. I always say he had a very close relationship, closer than most people have with their grandparents. He retired as a road worker when he was sixty, the year I was born. He spent a lot of time caring for me when my mom started working again, so I grew up very close to him. He would take me camping. He was a very down-to-earth person. Those moments were very important and maybe not typical for the milieu he came from. He came from very poor circumstances, growing up without electricity in an environment where everyone was very martial. He grew up to be the kind of person who takes care of kids and is very soft in many ways, but he was also very core. There are so many interesting things about him. There is one beautiful story about how he was. When he was four years old, on Saturdays they would get sugar and put it over a fire to make caramel. He did that and it slid down his throat so he couldn't breathe. He was so sensitive that he didn't want to disturb anyone, so he went around hugging his mom, his dad, and his seven siblings. Then he went out, lay down on the meadow, and prepared to die. Then it melted and slid down. He was a very special person. He was not the most talkative person, but he was extremely determined to do well and to help people. During COVID, when he was ninety-two and basically not holding together anymore, he would still take his rolling chair and walk five hundred meters down to the house where the elderly people stayed. He would go from window to window and talk to all of the people who were in isolation. He would always try to find some way he could be of use. Toward the very end he couldn't speak and was almost completely lost. I don't think he recognized anyone, but he was still the same person. One of the nurses told us there was another elderly woman in a wheelchair having a panic attack because she was afraid of death and dementia. She was acting out and throwing stuff. He saw that and, although he couldn't speak, he got up and moved slowly over and took her hand. He sat there for two hours just holding her hand because he could still sense she was getting calm. To the very end, he was always looking for ways of being of use to other people. He never cared at all about himself.

Henrik: (2:34:16) He was never self-centered in any way whatsoever. When he died, he instructed that he didn't want a grave; he wanted to be put in the communal grave without any plaque. I think he felt like his work was done and he was here to be of service. He made the atheism point too. He didn't believe in a life after this; he just believed in being of service and disappearing into the night. He formed me in so many ways. When I met Johanna, we bought their house when they moved to a senior apartment next door. That was set up so they would have some time to say goodbye to life in a gradual way. During those years when we lived there, we hung out. In the beginning, he would just barge into the house all the time and could always fix things. Gradually it became less and less, but you always had to do the good work. I remember we were going to a party and I had a suit on. He came and said it was the day for the potatoes. I said we could do that tomorrow because I was going out. He was eighty-seven and insisted it was the day of the potatoes. He went out and started planting. I couldn't let an eighty-seven-year-old plant all the potatoes, so I stood there in my suit and planted them. He wanted to do the right thing all the time. That was a very special experience. We spent three years where he was the closest friend I had. I spent more time with him than anyone else between the ages of twenty-five and twenty-eight, a very formative period in my life. I think that helped me shape some sort of value system.

Jackson: (2:36:41) There is a line from Herbert. I could be mistaken, so forgive me: "Repeat words stubbornly. Repeat all incantations of humanity, fables and legends, because this is how you will attain the good you will not attain. Repeat great words, repeat them stubbornly." Is there anything that you find yourself repeating?

Henrik: (2:37:07) I have some poems that I often return to, several by Tranströmer. There are a few lines I like to repeat where a sentence encapsulates an important thought like a simple diamond. Many of the ones I turn to are more like a mood. One I often return to is "A Short Pause in the Organ Concert" by Tranströmer. It is a beautiful rendition of him going into a church and experiencing a connection to the human condition. It comes out very strongly in that scene where he is standing in the church. There are certain lines where he talks about how the book inside every person gets rewritten every second. It's like a majestic book with so many pages that still have air between them, with waves going through it all the time. That poem puts me back into a sense of awe and care for the human being and for the condition we are in. It reminds me how fragile we are, how small we are, and how meaningful we still are.

Jackson: (2:39:01) I have one last thing. It's not a question; it's something I wanted to read. I'd like to hear if you have a reaction. It was one of my favorite things you wrote recently about a sculptor on the island. "If you look at the cliffs that have been carved by the glaciers during the ice age," he wrote, "you can still see the carvings there ten thousand years later. These shapes will live on for a long time." And this is you: "The feeling of a hand in 1972, made into an object that will stand for millennia. It is hard not to see a parallel to some of the oldest preserved cave paintings, which are hands that have been held up against the cave wall and preserved as silhouettes by color pigments blown at the hand. We were here, we felt this."

Henrik: (2:39:45) I think that is what it comes down to. There is so much work to be done. There are hospitals to be manned, companies to be started, and roads to be cleared. There is so much work to be done, but to me, the point of it all is the human experiences that it enables. When you see those examples from Argentina, where hunter-gatherers blew colored pigments on their hands to leave prints on the wall, it is a reminder of that feeling. Yes, we have to gather roots, we have to kill lions, we have to eat, and we have to mate. But it all comes down eventually to the fact that we are here. This is happening. Remember.

Jackson: (2:40:44) Thank you, Henrik.

Henrik: (2:40:45) Thank you, Jackson

(2:40:49) Thanks Again to Notion

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