*Dialectic Episode 19: Henrik Karlsson - Cultivating a Life that Fits - is available on [Spotify](https://open.spotify.com/episode/1iXfqPonC8nPgygvk9ufOu?si=5e2470a742ef455a), [Apple Podcasts](https://podcasts.apple.com/us/podcast/19-henrik-karlsson-cultivating-a-life-that-fits/id1780282402?i=1000710964687), and [YouTube](https://youtu.be/y48X_tx8H5g?si=YgsPcKWEOBIUaqy1), and all podcast platforms.* ![[19-henrik-karlsson.jpg]] <iframe style="border-radius:12px" src="https://open.spotify.com/embed/episode/1iXfqPonC8nPgygvk9ufOu?utm_source=generator" width="100%" height="152" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe> <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/19-henrik-karlsson-cultivating-a-life-that-fits/id1780282402?i=1000710964687"></iframe> <iframe width="560" height="315" src="https://www.youtube.com/embed/y48X_tx8H5g?si=YgsPcKWEOBIUaqy1" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> # Description Henrik Karlsson ([Substack](https://www.henrikkarlsson.xyz/), [X](https://x.com/phokarlsson)) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: [on designing your life](https://www.henrikkarlsson.xyz/p/unfolding?r=8rxu&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false) and [finding your wife (or husband)](https://www.henrikkarlsson.xyz/p/looking-for-alice?r=8rxu&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false). Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide. My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves. I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger. He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting [Henrik's writing](https://www.henrikkarlsson.xyz/), as he is fully reader-supported. --- **This episode is brought to you by [Hampton](https://joinhampton.com/community)**, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its **2024 Wealth Report.** They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report. # Timestamps - 2:36: Self-Cultivation, Introspection, and Larry Gagosian - 8:46: Writing to Think - 16:05: Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid) - 21:53: "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future - 25:12: Self-Criticism and Kindness to Your Past Self and Ideas - 28:44: Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends" - 33:10: Introspection, Agency and Being Sentenced to Freedom - 38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments - 49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us - 1:04:16: The Role of Ambitious Goals in the Context of Unfolding - 1:10:06: Hampton - 1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible - 1:26:53: Asking Questions that Push People Past their Cache - 1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet - 1:48:55: Ruthless Prioritization and Making Time to Get Better - 1:57:05: Initial Spark and Connecting with People - 2:05:58: Collaborating with Henrik's Wife Johanna - 2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition - 2:16:48: Sacrifice - 2:18:57: Pseudonymity and Playing with Identities - 2:20:57: Self-Organizing Systems - 2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold - 2:33:13: Writers Who Help Us See Ourselves - 2:35:13: Writing and Thinking in Swedish vs. English - 2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For Others # Links & References - [How Larry Gagosian Reshaped the Art World - The New Yorker](https://www.newyorker.com/magazine/2023/07/31/larry-gagosian-profile) - [Thoughts on agency - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/thoughts-on-agency) - [6 lessons I learned working at an art gallery - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/art-gallery) - [How to think in writing - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/writing-to-think) - [John Stuart Mill](https://en.wikipedia.org/wiki/John_Stuart_Mill) - [Alexander Grothendieck](https://en.wikipedia.org/wiki/Alexander_Grothendieck) - [Cunningham's Law](https://meta.wikimedia.org/wiki/Cunningham%27s_Law#:~:text=Cunningham's%20Law%20states%20%22the%20best,the%20inventor%20of%20wiki%20software.) - [A summary of what I wrote in 2024 - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/2024) - [Everything that turned out well in my life followed the same design process - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/unfolding) - [Awareness - Anthony de Mello](https://www.goodreads.com/book/show/94318.Awareness) - [Think more about what to focus on - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/multi-armed-bandit) - [On limitations that hide in your blindspot - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/limitatons) - [LessWrong](https://www.lesswrong.com/) - [Don’t sacrifice the wrong thing - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/sacrifice) - [Flatland - Edwin A. Abbott](https://www.goodreads.com/book/show/433567.Flatland) - [Sometimes the reason you can’t find people you resonate with is because you misread the ones you meet - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/friends-missed) - [Are you serious? - Visakan Veerasamy](https://visakanv.substack.com/p/are-you-serious) - [Into the abyss | Death Row Documentary - Werner Herzog (0:00-5:29)](https://youtu.be/QmyN3QJky7I?si=isliD6VUxQsncnqJ) - [Alexander Obenauer](https://alexanderobenauer.com/) - [A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/search-query) - [How Twitter gamifies communication - C. Thi Nguyen](https://philarchive.org/rec/NGUHTG) - [The Idiot - Fyodor Dostoevsky](https://www.goodreads.com/book/show/12505.The_Idiot) - [Looking for Alice - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/looking-for-alice) - [Adrienne Rich](https://en.wikipedia.org/wiki/Adrienne_Rich) - [Geoffrey Hinton](https://en.wikipedia.org/wiki/Geoffrey_Hinton) - [Pseudonyms lets you practice agency - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/pseudonyms-and-agency) - [The Learning System - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/learningsystem) - [Spring - Karl Ove Knausgård](https://www.goodreads.com/book/show/36723048-spring) - [Steve Krouse](https://x.com/stevekrouse/status/1921380764114948317) - [Tomas Tranströmer](https://en.wikipedia.org/wiki/Tomas_Transtr%C3%B6mer) - [Thomas Bernhard](https://en.wikipedia.org/wiki/Thomas_Bernhard) - [The third chair - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/third-chair) - [Tyler Cowen](https://x.com/tylercowen) - [#003 - Henrik Karlsson on Creating Your Milieu, Writing, & Apprenticeships - Audience of One](https://open.spotify.com/episode/4IvqF4kVXQRkNPwVVOpRfK?si=c20c2e46538645e4) Dialectic with Jackson Dahl is available on all podcast platforms. [Join the ⁠telegram channel for Dialectic⁠](https://t.me/dialecticpod) [Follow ⁠Dialectic on Twitter⁠](https://x.com/dialecticpod) [Follow Dialectic on Instagram](https://www.instagram.com/dialecticpod/) [Subscribe to Dialectic on YouTube](https://www.youtube.com/@Dialectic) # Transcript **Jackson**: Henrik, thank you so much for being here. **Henrik:** Thank you, Jackson. So fun to be here. **Jackson:** A nice little bit of serendipity crossing over the same part of the world. I don't do these interviews over Zoom, so I don't know if I'd normally be able to get you. It's great to be with you. **Henrik:** It's really nice. I think you're the first person who has hunted me down. **Jackson:** You put in some effort to make it work for me too, so I appreciate it. ## [00:02:36] Self-Cultivation, Introspection, and Larry Gagosian **Jackson:** It's funny. You've described much of what you write about as self-cultivation. I see you as someone who has very much curated and designed a specific life for yourself. This was partly exemplified when I was texting you some long instructions for where we were going to meet up today, and it literally didn't go through because your Nokia phone doesn't receive MMS messages. **Henrik:** Yeah. **Jackson:** How old is your phone? **Henrik:** I don't know. I have a version of Nokia phone that I bought. I have a stack of them, so I keep changing them. I've had that phone, the same model, for 20 years or something. **Jackson:** Amazing. We'll get into all of the ways I think your life is unique. I want to start with a maybe hilarious, or at least odd, comparison or contrast, which is funny, I think, given your work in an art gallery. There's a piece in The New Yorker from a few years ago on Larry Gagosian. **Henrik:** A great piece. **Jackson:** Amazing piece. There's a part in there that always stuck with me, and I wasn't sure why—if it was partly because it made me feel insecure or because it made me realize what I didn't want. It was just in such interesting contrast to how I live my life. It says: “In Michael Shnayerson's 2019 book Boom, a director recalls asking Gagosian if he might write a memoir. Gagosian's response was that he avoids self-reflection because that is how you, quote, 'lose your edge.' The late art critic Peter Schedule once observed, 'We think of genius as being complicated, but geniuses have the fewest moving parts. Gagosian is simple. He is basically a shark, a feeding machine.'” Meanwhile, you seem to be a shining example of someone who is deeply introspective and yet is simultaneously full of action. You have taken a great deal of agency (a word that we'll talk more about that's very popular these days) to use your introspection to design a very specific life for yourself. I have to admit, if I were going to choose between two lives, I would choose yours over Gagosian's a thousand times out of a thousand. I thought it was interesting to see that contrast. As someone who I think has always had a lean toward introspection and wondered how useful or meaningful it is, your writing has been really empowering for me. My first question is: what does it mean to be introspective? And how have you gotten better at not protecting yourself or not lying to yourself? **Henrik:** There are a bunch of interesting things there. First, with Gagosian and that stuff, I would probably be a lot more successful if I didn't introspect as much. I've definitely turned down paths that could have led to greater success because they didn't align with what I believed in or felt inside. I think I've always had a great touch with myself, comparatively. I think that has to do with where I grew up. I grew up in the middle of the woods in Sweden. It was a small village, 672 people when I was growing up. It was a very protected space, and we were roaming the forests. It was a very playful space. I think I just kept going with that. It feels like that's what I'm still doing. We would find abandoned houses deep in the woods. We'd have computers there and pick them apart, or we'd make movie studios and renovate the houses and learn things like that. It just feels like I've kept going with that. I think a lot of people have the type of introspection that I like. I often talk about introspection for doing. I try to avoid sitting down too much and just reflecting on my feelings and ruminating. Instead, I take a few minutes here and there to notice what pulls on me and then go out trying things, and then you get feedback. I think a lot of people do that as kids. You see something, like an abandoned house, and you want to climb into it. Then you just do that, discover things, and keep doing things. I think it's mostly just protecting something that a lot of people have as kids. **Jackson:** There's almost a slight similarity. Maybe there's the bell curve meme here. Ultimately, Gagosian and you, in some sense, are on similar ends of the bell curve around getting back to the simple thing. The fear of too much introspection in a negative way is that you're stuck there and don't do anything with it. It's interesting that you came back to something quite simple. Even though you're very attuned and spend a lot of time thinking about big ideas and what you want out of your life, it comes back to something, as you say, almost childish: what makes you feel alive. **Henrik:** Yes, it's very much that mid-wit kind of thing. When I worked at an art gallery, I would sometimes mentor art students. They're always so fun. They're often very attuned to themselves and are really crazy creative people. When I was interacting with them, I had to take this Gagosian-type role, explaining to them that they need to fashion a brand out of themselves and figure out how to network commercially and do that, because you have to have both of those things. That's the really hard part. If you don't have introspection like Gagosian, and you just go for it, optimize for agency, and optimize for growth, you can go really fast and far and have a terrible, painful life. It's really nice if you have someone like an art student who is really connected to their creativity and then also learns how to be agentic. When you can have that combination, it's very rare. That's such a beautiful thing when that comes together. **Jackson:** I want to talk more about that ## [00:08:46] Writing to Think **Jackson:** for you. I think it starts with writing. And obviously writing and thinking, as you've written extensively about, go together. There's one bit where you say at a certain level, the rate limiter of how well you can write is introspection. The whole point of writing is to show the inside of your head. Then you've called writing putting your thoughts in order. It reminded me. Paul Graham, the founder of Y Combinator, says writing converts your ideas from vague to bad, which is another one of my favorites that feels very aligned with you. You go on to say at another point, good thinking is about pushing past your current understanding and reaching the thought behind the thought. It often requires breaking old ideas. This is easier to do when the ideas are as rigid as they get on the page. In a fluid medium like thought or conversation, you can always go, "Well, I didn't mean it like that," or rely on the fact that your short-term memory is too limited for you to notice the contradiction between what you're saying and what you said 12 minutes ago. And it's interesting there's an interpretation of that that paints introspection as maybe much more scientific than most people's feeling about it might be. I'm curious for you: why is structure and process so important to understanding yourself? **Henrik:** That gets to an interesting thing. There's often this distinction: some people are more into logic, process, and reasoning, and then there are the feeling people who are intuitive. I think that's a false dichotomy. I'm inspired by John Stuart Mill, the philosopher. He wrote \*On Liberty\* and the strongest arguments for free speech. What was interesting about Mill was that he was a rationalist super-baby. His father and Jeremy Bentham had this idea of raising a super-genius who would push philosophy forward, utilitarianism, and create modern government. They raised him in a disciplined way. He had internalized logic and would study classical Greek logicians when he was about 8 years old. He's interesting because eventually, during the Romantic era, when he was in his 20s, he got in touch with the Romantics. This was the whole idea that there's some mysterious core to you that you manifest in the world. We're still living in a very romantic era with this idea of authenticity. He came in contact with that and felt there was something true to that romantic idea. He was then able to integrate those two things and think about that in a deep way. I resonate with that—this idea that they go together. You can use logic and reasoning to figure things out, but you also need to use intuition. It's not straightforward how those things go together, but you can try to push both things forward. I saw a meme about the Pareto frontier. Often, people talk about trade-offs, like trade-offs between process, reasoning, and intuition. That's only true if you're on the Pareto frontier. Speaker 2 Ah. **Henrik:** The proper answer is, let's do more of both because we're not at the frontier yet. I think what philosophy does, if you go back to ancient Greece, real classical philosophy is that process. They're starting from moral intuitions, and then they're using logic and Socratic dialogue to unpack that and see the false assumptions. Often, I find that I have several intuitions, so then you can't follow your intuition. You have to unpack which is the real intuition. Then there's this back and forth between reasoning and intuition. I might articulate my intuition about what I should do, and then I can use logic and reasoning to unpack and critique that, then refine my intuition. It goes back and forth. **Jackson:** In the interview before this, I interviewed this guy, Tom Morgan, who's very interested in Ian McGilchrist and left brain, right brain. I think there's a similarity here: intuition isn't necessarily vague or fuzzy so much as it's not necessarily verbal. What I think is powerful about writing, in the way you talk about it, is that writing, you say, allows you to order your thoughts. It allows you to put everything on the table and look at it a little bit more clearly, or at least know what the known knowns are. I think people who bias towards intuition, it's almost a cop-out. They can say it's intuitive; I don't need to put parts of this in order; I don't need to make parts of this structured; it's just all intuitive. Whereas the best intuitive people, or the people who make the best gut decisions, do so with plenty of structured inputs. By actually making their inputs more structured, they can result in a non-verbal, intuitive, wise choice or decision, or whatever it might be, in a way that they might not be able to explain explicitly to somebody, but at least the inputs are structured. I find that flywheel you describe is really powerful for almost all of my thoughts. I end up copping out if I just say it's a gut thing. It's not a rational thing; it's not a reasoning thing. I can still make some of these inputs more objects so I can play with them and turn them around. **Henrik:** You have to think about in which domains. I have a very rationalistic take on what intuition is: it's just pattern matching. I don't think there's any divine thing, but that would be really great if it was. If you think that it's pattern matching, then you have to understand that there are certain domains where it's even possible to have intuition. An experienced firefighter is going to have great intuition for when to evacuate a burning building. But a lot of the times, people who are picking stocks or something might not even have any intuition. Or, if you are 19 years old and are going to pick your major, you're not going to have an intuition because you have not had any feedback to develop a pattern-matching capacity. Whereas someone who's a wise mentor figure who has seen thousands of young people grow into competent versions of themselves might be able to look at some person and say, "You should really go into software or something." You can't have intuition without tight feedback. **Jackson:** Totally. ## [00:16:05] Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid) **Jackson:** You have an amazing piece, and it comes up in a few different areas around using conjecture, what you might call takes or strong opinions, and error. This is a different section, but I thought it connected. I wrote about the thoughts that passed through my head as if my thoughts mattered unironically. I think that's from \*Looking for Alice\*. But I thought it was interesting the way it connected. It's the piece where you talk about growth and Deke, and you say, "Forcing the diffused ideas and impressions in your head into a definite statement is an art form. You have to grab hold of what is floating and make it rigid and sharp. It can feel almost embarrassing. Revealing your ignorance with as much vulnerability as possible." You go on to talk about this idea of increasing the surface area for beliefs you might have so that they can be pressure tested. It's this really interesting notion that perhaps we would all benefit to have more strong opinions if we are willing to hold them with a loose enough grip or willing to update them. Put another way. We live in a world with lots of strong opinions, in the media world in particular, where the incentive is to broadcast, to shout your opinions as confidently as possible and never correct yourself. There's very little learning. But you advocate for this world where it's beneficial to have a strong opinion even if you're wrong, so long as you are willing to update it when you are wrong. You give an example: you were asking somebody if the dynamic between the Greeks and the Romans is similar to the Japanese and the Chinese, and you acknowledge being wrong, but it created an opening for you to learn. The root of the question is: how do you balance this strong-take-oriented, high opinionatedness, but also not get too lost in your own confidence? **Henrik:** It's a very peculiar state of mind to imagine we could do a typology of different types of people. There are people who have strong opinions, hot takes, and are never updating. Then perhaps a really large group are people who are really good at critiquing and taking things apart. That is really important. It's a really important part of the process. But the problem is you can't only critique; you have to have something to critique. A wonderful thing about Grothendieck, whom you mentioned, is that he was an absolutely marvelous mathematician, but he had this childish wonder. Whenever someone started to talk to him about some new area of mathematics he had never heard about, the person would talk for 30 seconds explaining that area, and he'd say, "Oh, it has to be like this!" He would immediately say, "It has to be like this." Then someone would say, "No, no, it's not." Then he'd say, "Oh, it's not? Why?" Then they would say something, and he'd say, "Oh, then it has to be like this!" "No, no, it's not." But that capacity to be stupid and just articulate something—because if you're not articulating, you're having that thought anyway, in some unarticulated sense. As we're having this conversation, I probably have a bunch of assumptions about who you are or what you're getting at. But as long as they're in my head, and if I'm not articulating them, you can't correct me. Especially now that I've gotten to a larger scale, I have a professional army of people telling me when I'm stupid. It can be very frightening. It's very tempting to retreat into making foolproof arguments and filling in all the holes. But that slows down the rate of learning. One must be willing to put this out, knowing it's going to go up on Hacker News and 137 programmers are going to tell me I'm stupid. Then I can read that and learn. That's such a useful process. But to get back to your question: this is somewhat intuitive and logical when you say it like this, but it's a very peculiar state of mind to inhabit. It's so easy to either fall into being protective and only critiquing ideas and looking for flaws, or, if you're putting something out, to protect yourself and start to have confirmation bias. It's a very delicate thing. With all these very delicate states of mind, I think they can only be cultivated in communities of practice. You have to observe people do this and interact with them to get that sense. It's not something that's going to spread memetically. It's too complex to summarize. It's a very peculiar way of orienting inside yourself emotionally. But to start to feel a certain joy in being wrong, asking, "How can I be more wrong faster?" and to recode the shame of being wrong. **Jackson:** Turn that into a dopamine. **Henrik:** I think that just takes a lot of practice because the first 800 times you're going to feel shame, but then eventually... **Jackson:** There's something deep inside that which is a disposition to actually listen. This involves saying something with an opinion, taking a position, but then the crucial act is listening. For most of us, the temptation, if confident, is to not listen. It's also funny how much this embodies that silly notion. If you want to get an answer to something quickly, just say the wrong thing. **Henrik:** Cunningham's Law. ## [00:21:53] "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future **Jackson:** You have another frame for this, which is resisting what you call "not that." You say this way of formulating it, "not that," is a bit vague, as it only defines where not to look for the solution. It is useful to also attempt a positive formulation. I think you're talking about what you had brought up: the disposition to critique, where many people run through the world "not that-ing" everything. It's the opposite of the "take" person. Why is having a positive formulation, as you say, so important? **Henrik:** The positive formulation is a probe; it's something that's reaching out toward the world. For instance, if I'm deciding what car to get, I might say, "I'm not going to get a Tesla because I hate Elon." Okay, let's not get that one. But then you can't really critique that option. So, we have no car. What should we discuss? There's no data; we can't examine that non-car. You have to propose something, for example, "I think I'm going to go for a Chinese car." Then you can start discussing, "Oh, do you really want to do that?" or "Should it be electric?" It's much harder. Here's where it almost makes sense to talk about the divine and intuition, because there's something almost mysterical about how positive formulations come about, especially in very creative domains. I was with some friends, and we were producing music yesterday. We had a song, and we were like, "Not that." To go from "maybe we have..." We like the chorus, we like the verse, but we're not sure what to have as a bridge. We only know what shouldn't be there. **Jackson:** Yes. **Henrik:** Then to go from there and somehow, from some part of yourself, pull out, "Maybe this." Maybe we should go with this thing. It's such a... Where do these things come from? A lot of people struggle with pulling that thing. If you're sitting with a chorus and a verse, to be able to throw out a melody that would be the bridge takes a stupid bravery. But it's so important because until someone—we were four guys there—puts out an interesting idea, that's when we can start talking about it. **Jackson:** That's the beginning. **Henrik:** Without that step, there's nothing to react to. There's no feedback, no data, no emotional reaction. All the flow of information that leads to new insight starts with someone saying, "Maybe this." **Jackson:** Maybe this. It's beautiful. It's not exactly the same, but it's a little explore, exploit. "Not that" and "maybe this" are almost two totally different modes. It would be more helpful if you could, at least in the music sense, say, "We're in the 'maybe this' part of the session." Then at some other point, or maybe it's even like, "write drunk, edit sober." There's an element of this total phase shift. ## [00:25:12] Self-Criticism and Kindness to Your Past Self and Ideas **Jackson:** You have a beautiful framing around criticism of your own ideas. In learning and updating the model, you say the original idea remains the seed, no less valuable for having been wrong. It takes creativity and boldness to leap out and form a conclusion. The part that criticizes must understand how dependent it is on the part that throws ideas at the wall. It is often easier to criticize than to synthesize a new position, which is part of what we were just talking about. How do you maintain or even cultivate kindness and generosity with yourself and your former ideas to create this loose, open environment where you are free or willing to do the "maybe this" before you get into "not that" mode? **Henrik:** : Again, it's practice. Concretely, tactically, day to day, I have to figure out what makes me get into that creative flow. For me, it's a lot of walking up and down the farm and using transcription and talking. Because when I can't see what I've typed, then I can't critique it, and I just keep going. That works for me. I also try, for most of the week, to block all notifications so I don't see. I can go in and look at the critiques I get on Twitter and on Substack at specific times. I don't have that in the back of my head all the time. You have to figure out what works for you, what puts you in that playful state, and be able to protect that because it's really hard to protect. There are so many forces pulling you down, like distractions. You have to be in a very open space of mind, but also you have to be unprotected. It gets better with practice. I've been writing very hard for four years now, and that's been so interesting. When you go through this, it's like you do gradient descent on your own mind, in a sense. I've updated so many of my mental models and how I think. It's also rewired my brain in some sense, and what I get rewarded for internally. I feel that phrase where you have to feel love for the seed, the way you were wrong. I feel so much like that now, especially looking back. There are things I did or said when I was 17; I was super stupid. I used to think, "Oh, why did I do that?" Now I think, "But how was I supposed to be where I am now if I hadn't done that?" As a 35-year-old, I can see there were better ways of doing it, but that was my best guess. I have to love that because making that bad guess taught me things and let me grow as a person into being the type of person who could critique it and see what's wrong with it. Now I look at that person who did all those stupid things and think, "Amazing, Henrik, you're so, so beautiful. Stupid things you did." I think I've rewired my brain into feeling a lot less shame around being stupid. ## [00:28:44] Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends" **Jackson:** Speaking of a younger version of you, you've got quite an eclectic past. I'm sure I'm not even covering anywhere near the whole of it, but a few categories: poetry, I know you were doing for a while; software engineering; music. Maybe a little bit of that this past weekend too. How do you think those—either those or others—that eclectic mix has shaped you as a writer, especially across pretty concretely different mediums of software, poetry, and music? **Henrik:** That's one of those things I could feel shame for early on. I was drifting, trying things, and moving, and I thought, "Oh, I'm so stupid. Why can't I just settle on something and just keep?" The poetry thing was going well, I had my writing workshops, and I had a book deal. I wondered, "Why do I have to throw this away and then do something else?" I was doing programming and then had a consultancy, and then I threw that away. Why am I doing that? But again, it's just intuition. I went there and was learning things. Now, in retrospect, I can see I'm obviously pulling a lot on mental models I got from computer science as I write. I'm obviously using techniques I learned from poetry as I write. I'm obviously all sorts of things. I used to work in shipping, packing medicals when I was a teenager, and I use those techniques that I learned there when I'm packing and sending artworks at the art gallery. So everything comes back in. At this stage, a lot of the writing I do now is looking back at all these things that I was sort of ashamed of, that felt like dead ends. Now I'm looking at that and seeing there's a lot of wisdom there and things I learned. It's a wealth of experience from that. There's something beautiful now looking back at working in different industries for six months to a year. You can learn quite a lot in six months. I worked at a bio lab for six months when I was 19, and I know a whole lot about DNA sequencers and enzyme extraction and things like that. I'm not good at that, but it's really interesting to understand. Now, if I'm talking to someone in a bio startup or they're researching some HIV vaccine, I sort of know what they're talking about. I understand what the machines look like. I understand what it's like to be in a lab like that. It's just really fun to have a highly textured tapestry of reality. **Jackson:** You have this piece summarizing your work from 2024, and you open it with this beautiful frame around all the ways the themes became available to you in hindsight, or at least started to resolve in hindsight. It's funny how our lives seem to be a bit like that too. There's the classic Steve Jobs idea: the dots only connect in reverse. But especially in creative fields, for some reason we take this notion that, "Oh, you did all those other things, and those are time-blocked. And now you've begun as a writer and you're starting anew." Maybe you are in some sense, but how could they not? How could that mix for twenty years, or whatever it might be, not be deeply informing? **Henrik:** If you want to be a writer, I think that's a good idea to do too. I don't remember who, but someone came to Osip Mandelstam, a Soviet poet. He asked Mandelstam what he should be doing because he was a young poet and wanted to learn how to get well. Mandelstam said, "Don't write anything for ten years. Go out to a mine. Go out into the woods. Just fill yourself." **Jackson:** Yeah. **Henrik:** With lived experience, and then you can write. I really wanted to be a writer for all of those years when I was doing those things, but I couldn't have been. I could string sentences together, but they didn't have that sort of light behind them that real writing is supposed to have, which can only, I think, come from lived experience. ## [00:33:10] Introspection, Agency and Being Sentenced to Freedom **Jackson:** It's a good transition to go back to introspection. You talk about introspection by doing. There's a frame I found initially shocking, and the more I've thought about it, really powerful: introspection and agency being the internal and external frames of the same idea. I think this is pretty non-intuitive. You have a piece you wrote about agency. The more common frame of agency can be very—I don't mean this word totally in a loaded way—somewhat exploitative or competitive. This is a sort of orientation toward the world of seizing opportunity wherever it is. And you frame it a bit more about an attunement to yourself and perceptiveness around yourself. There's one sentence that I loved. You were talking about writing a book for your daughter, Maud, on agency. You say it's a book about how to handle being sentenced to freedom, and to handle it effectively, authentically, and responsibly. "Sentenced to freedom" is amazing. **Henrik:** Maybe Sartre said that. **Jackson:** Maybe I'm getting ahead, or... **Henrik:** Or... **Jackson:** ...or maybe that subverts my question. I didn't realize that was Sartre. But in either case, why is that set of words so resonant or meaningful? **Henrik:** Maybe it's the Nordic melancholia that I have. But freedom is a very, very heavy burden. What Sartre was getting at with that phrase, if I remember the content correctly, is basically that. Kierkegaard talks about the same thing. You can pretend that you're not free. You can pretend that you have to follow norms and rules, and you can pretend that there's group pressure, but that's you deciding to do that. So you can never outsource it. Or, if you're a Christian and you believe in God, that's you deciding to believe in that. You can never get away from being the one making the decision. And that's a pretty horrifying thought when you realize it. You realize you're probably doing a lot of harm to other people. You might say, "But that's the incentives, that's how the world is." No, that's what you decided. Once you realize that you can always make a choice, that's a pretty heavy burden. For me, it also goes further and connects back to the romantic idea. I also think your genetics and your experience enable certain types of things to happen in the world, if you unblock and stay attuned. Both in a Hayekian sense, you're going to be in certain positions, see certain business opportunities or arbitrage, and that's going to provide value to the world. If you're not acting on the information you have about how a certain logistical problem can be solved, then it won't be solved, because you're the only one who has that information. Also, in an artistic sense, you might have an attunement for essays or a certain attunement for particular relationships. If you are not paying attention to that information that is flowing for you because of where you've been and what your genetics are, then you're not taking your responsibility there. **Jackson:** There's a stewardship there. **Henrik:** Yeah. **Jackson:** Duty. **Henrik:** ideas go together, pointing to the same landscape. Freedom is attunement, being attuned. If you can pay very close attention to what you are seeing and sensing, and act on that information in the best way you can, then you're handling your freedom responsibly. That's a very hard thing to do because it gets back to agency and introspection. To really handle it well, you have to understand how the world works, how to get stuff done, and how to be agentic. But if you're only doing that—and I can feel some disgust for a certain type of romanticism around agency—it's ethically unmoored. **Jackson:** I hear you. **Henrik:** Not everyone uses the word like that. I've thought about this. It makes sense to reserve agency for just power; it's basically the capacity to get stuff done. That's morally neutral. If you're doing that without having the attunement to the ethics, the curiosity, and whatever is flowing through you, then that can end up in some really dark places. **Jackson:** Totally. ## [00:38:09] "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments **Jackson:** It's not obvious that what is attuned to yourself is always what is attuned to the world, although my sense is that they become more likely. You have this really big idea of finding fitness in the world. One of my favorite essays you've written is the piece on unfolding. I think it's "Everything You say this is true of relationships, essays, and careers: you want to find something that fits. Self-actualization means that you have designed a life that fits you, that allows you to express your human potential. I'm more curious, what does fit feel like? As someone who is deeply introspective and agentic, you have followed your own advice. What does fit feel like? **Henrik:** It feels good. I'm a quite sentimental person. I live on a nice little farm with my kids, and I can see they are having such a good life. I'm so proud of that. I'm getting to have time to discuss ideas with my wife and talk to Jackson. I have a really interesting life, and I'm close to the edge of my ability, following my ethics and all those things. Sometimes I get tears in my eyes. It's really good. I feel very alive. I feel very grateful. I feel love. As I was talking about earlier, when I was flying out, I just look at people and I feel love. It's a very expansive feeling because I don't feel needy at all; I feel held by my life. I feel held by my readers, my family, and the nature around me. That makes it much easier for me to feel gratitude and love for everything. I look at people on the street and think, "It's so nice that you're here." There's heaviness to it too, because it means trying to turn toward hard things. I'm 35 now, getting into that early middle age where relatives and loved ones are getting sick, people are dying, and there are hard things to stay attuned to. There's a heaviness, but there's also deep love in that. It feels alive. **Jackson:** It reminds me of Amor Fati: to be in love with your own fate. There's a framing that maybe came up in something you were writing, but I initially came across it in Anthony DeMello's book \*Awareness\*. It's the idea that you care about the outcome, but you are okay with either outcome. This Zen-like approach to being very okay and settling into your life. In that piece I mentioned, you talk about unfolding, form, and context. There are two excerpts that illustrate the core ideas from Christopher Alexander you're talking about. You say, "The context is smarter than you. It holds more nuance and information than you can fit in your head. Collaborate with it." That's an awesome framing. Then you say, "You have lost track of all the experiments and insights that led you to a fit. But the good news is that you don't have to remember it. The form does." I love that. This idea of unfolding inside of it is, at root, experimentation or iterating with the context, as you say. You say, "Extracting info from the context and baking it into form to create a process that produces a design that's smarter than you." You've also written about the multi-armed bandit problem, exploit, and a lot of these different ideas. This is you on experiments. Then I'll ask a question. You say, "Perform experiments. By this, I don't mean do random things. I mean state your assumptions and find way to test if they are false. Most of the time, the slot machine of an experiment yields nothing. But that's okay. A few will rearrange the world around you by increasing the speed at which you can act on the context. Trying new things will become cheaper for you, so you will take more risks and extract more information from the context. Write faster, prototype faster, ask for feedback faster. Velocity is underrated." There's a frame you used around collision with reality. What makes for a good experiment that allows you to collide with reality, specifically across different scales? You can imagine an experiment like, 'Do I like this hobby? Do I like Jiu Jitsu?' And you can imagine an experiment like, 'Should I move from my home country to an island in Denmark so I can homeschool my daughters?' Is there a through-line across experimenting across those different modes? **Henrik:** : An example of how is very straightforward and basic, and people do it more or less. When I started working at the art gallery, one of the first things I was thinking about was how to rebrand it. Can we make it more intuitive to people what kind of value we're providing and why they should go here? Can we get more people in through the door? The fast and simple way I found to do that was just to go talk to everyone who went into the store. I tried different ways of framing, explaining who we were. Then you start to notice people's eyes light up when I tell that story or that framing or that phrase. Then I try to say that same story slightly differently. I do that 300 times or 400 times. I intuitively try different variations until I find something. This is a good first draft of our new branding. Then, of course, over time, run new experiments and test it. The mistake people would make is that there'd be a committee or something, and they talk about it. Or they would sit and run some PowerPoint slides and think about it. But it's so fast to just go up to someone and do an improvised version of your new press release or whatever. It takes 15 seconds. With bigger decisions, like when we left Sweden and moved to the island, that was a really big decision. Those things, of course, take longer. We were thinking about that maybe for four years. We didn't know where we were going, but we knew we wanted to leave Sweden to homeschool. Where should we go? Whenever we had some money left, we would travel to places where we could reasonably live. We just went from place to place. We would contact people who might have information and ask which villages have more homeschoolers, start mapping that out and figuring out what's close to home. Then you make a guess that these three places seem most promising. Then you try to, as rapidly as possible, go there and just experience what it's like to be there. Just getting information as soon as possible and honing in. We're going to move somewhere, probably in Europe. That's too broad. You can't just randomly go to random places. You have to have some criteria. You start listing constraints: we want it to be fairly easy to travel home; we should afford it. All these things. Then you start listing constraints and mapping out potential solutions. You take the first best idea and try that, and then the second best, and keep going and surfacing. As you do that, you surface more and more constraints. You go there, it's like, "Yeah, but maybe we also want the nature to look nice, not this pine forest shit." **Jackson:** There are two follow-up questions I have there. One is the first example. Can I test a bunch of different ways to pitch this art gallery in that multi-arm bandit piece? I think you do a great job of talking about the classic explore-exploit idea from computer science. I think most people will try something three times or five times, and then they'll choose the one that works the best of those, or they'll find anything that kind of works and they'll just stick with it. It takes a certain kind of energy to try something. Maybe you didn't literally mean 300. Our mutual friend Ava talks about this with therapists or dog walkers. She's like, yeah, you should try 30 therapists because eventually you'll find one. I think most people are either on the end where they don't have the energy to try a whole bunch of things, or they swing to the full opposite end of the spectrum, kind of like we were talking about earlier, which is they're sort of Peter Panning through life and just sampling everything and never settling anywhere. **Henrik:** : You have to decide how important. You can't do everything properly. You have to have your priorities. That's why it matters to really think hard about your goals and values and so on, because you're going to have to rank order. My philosophy is that I'd rather do a few things really well. That comes back to attunement. There's a certain pleasure to going in very close combat with reality and just going really deep on a few things. I try to think really hard about what I value, and then I just cut away all of the things. As I mentioned, I don't have a smartphone because I cut away a lot of things that I don't want to have in my life. Then I don't have to think about which smartphone I should get. I have the same Nokia that I've had for 20 years. That's a nice enough phone. I'm just going to keep using the same phone forever until they stop doing them. Instead, I'm going to spend ridiculous amounts of time figuring out where to raise my kids. Or at the art gallery, if we can't get the branding right and get people to know how to explain who we are to people and get people in through the door, then nothing else matters. Then 300 times is the least you should do. Whereas, what color should the homepage be? I don't know, white. **Jackson:** Just spend five. Spread very thin. **Henrik:** : Yeah. **Jackson:** It's a painful realization. ## [00:49:06] Seeing Past Blindspots and Listening to Feedback the World Gives Us **Jackson:** On the note of fit, especially around your work, presumably you were doing some unfolding as you did poetry and music and computer science. Perhaps it's not exactly the right question, but what feels different about writing in this phase than those previous things, which were also creative, and in the poetry case was even writing? Is it about the outside world reception of it? Is it purely internal? Is it both? **Henrik:** It's both. The big conceptual breakthrough for me, an obvious thing in retrospect, was that I should have a blog in English. I always wanted to write. As a Swedish person, it's not obvious that you should write in another language. Most people write in Swedish, and that limits your audience. Once I realized that, I thought, why would I write in Swedish? The audience is 1% of the English-speaking audience. This means you're much more limited in what you can do and in addressable markets. You're never going to be able to fund anything interesting if you write in Swedish. It's mathematically impossible. Something clicked into place for me there. The blog is such an open-ended vehicle. There's such a large market of people who read it and are willing to fund it that I can steer it in ways not possible with other things I've tried. When I was doing programming, it was very limited. Maybe if I'd done a startup, I would have had more, but I was doing consulting, so it was very limited in how I could steer it. There were not that many degrees of freedom. Writing for magazines offers almost no degrees of freedom. The blog is a good vehicle. That makes it very unfolding-friendly. I can see myself doing it for 50 years because I can. Maybe in year 30, it's going to be all about Sudoku, and that would work too. **Jackson:** Great containers, vehicles, tools adapt along with us, which is powerful. You mentioned the switch, and maybe the unlock, from writing in Swedish to English. You've also written broadly about blind spots, seeing through things, seeing through abstractions, map versus territory, and even a hacking orientation to things. You've said, "My preconceptions are a filter that reduces the amount of information I get from the context. How can I filter less?" And, "When the context thrashes one of your ideas, you want to say, 'Oh, that's interesting.' It takes practice, but it's worth getting better at. Reality is shy. It only reveals itself to those who, like honest scientists, do not wish it to be something else." And one last bit, you were talking about how we bundle things. You said, "A career is made up of a bunch of different things, like a salary, an identity, relationship, status, a sense of meaning, and so on." That's not necessarily the exact same as switching from Swedish to English, but they're all circling the same idea: the types of things you look back on and say, "Oh my gosh, duh." What are the most critical? Maybe the Swedish bit is one of them. But what are the most critical preconceptions or ideas that you used to hold firmly, that, by dropping them, have enabled you to act more freely or see more clearly? **Henrik:** I write essays for a living now. I think I knew, if I'd listened to myself, that was what I wanted to do when I was 20 years old. I remember I wrote a bunch of pretty good essays. I met my wife when she read one of my essays, so we connected over that. I just remember when I wrote those pieces, something came alive in me. **A somewhat concrete example:** She makes fun of me because she was saying, "You should write essays because you love writing essays." I was really stupid. I was saying, "But no one reads essays in Sweden. Compared to Germany or the US, there are magazines that publish essays. There's nothing like that in Sweden. We have no tradition of essays in Sweden. No one writes essays for a living in Sweden. You can't do that." So then I didn't explore that. That's so stupid because if you get a signal that something is alive, I should have just done that and then I should have figured out a way of funding it, which could have been having a software consultancy or whatever. It was so stupid of blocking off an avenue that was the right one. In retrospect, I didn't go down there because there was no established road to go down. **Jackson:** The rational mind was on the side of fear versus the side of what you knew. **Henrik:** Yeah, but it's such a stupid argument. If you discover this feels alive, the only job I have is to figure out what feels alive and then figure out how to fund that. They're not the same problem. Now I'm lucky that the thing that feels alive to me pays my bills, but that's not necessary. The important thing is to feel alive and to have food on your table. They're not the same problem necessarily, but I treated them as the same problem. I bundled that. I figured I want to be a writer, but I want to pay my bills doing writing, and you can't do the kind of writing I want to do, so I'm not going to do it. So stupid. **Jackson:** And impatient. **Henrik:** Yeah, impatient. But when I unbundled, eventually, later, I unbundled and I said, "I'm not going to be a writer. This will never work out because the stuff I want to write, no one would ever pay for." So then I started a software consultancy. I did other things. I worked at the art gallery and so on. And I just wrote for myself because then I just carved out space and I unbundled it. Suddenly I could just live in my writing. And then, of course, I got much better at it and I grew and I got an audience. Then from a magical backdoor that I could have never predicted, it became a livelihood. But I couldn't have gotten there by thinking about the funding. That's one of those examples where I look back and I was like, "Oh, this is so conventional-minded, Henrik. You should have just listened to your instinct there." Many of those, like homeschooling for us too. Homeschooling, super taboo in Sweden. It's funny to look back because we knew we didn't want to have our kids in school, and we spent so many years trying to avoid saying that we should homeschool. It was like, "Could we start working at a school and maybe push it in the right direction?" No, that doesn't work. "Could we start a school?" No, that doesn't work because of legal things in Sweden. "Could we move to another country and start a school?" We were going through the whole list just to avoid it because it was so painful to say "homeschooling." That is like child abuse in Sweden. Emotionally, it felt like saying, "Oh, we're going to abuse our kids." It's just so stupid in retrospect. No, you can do it nicely. So many of the really important things in my life have come from me switching a position 180 degrees. **Jackson:** There's classic advice that comes up, so frustrating to hear, yet continually true: you know what you need to do. But we do so many gymnastics. It's also amazing that on the idea of bundling or unbundling, the world has a way of rebundling and rearranging itself when you do the thing. As Joseph Campbell said, doors will open where there were only walls. It's telling that you set out to do the writing, and now the pieces are coming together. On the note of blind spots, you write about how our mental models seek to make the world predictable, and how part of the opportunity to see blind spots and learn is by making things less predictable or seeking unpredictability. Do you have a sense of how we can make reality less predictable, within reason? **Henrik:** : I noticed there are certain practices that I use. For example, I try to seek out when I'm writing. I've gradually, over time, started out more in the less wrong kind of blog post: very cerebral, very abstract. About two and a half years ago, I had an insight that that's a really stupid way of doing it. It was embarrassing because I had gone to that, escaping from the literary world. I felt it's really nice to have people who are actually trying to think. That's so nice; some people are thinking. There are people on LessWrong who are doing really good work too, I should say. Then I realized I need to be telling stories. I need to be talking about specific situations, specific people. I need to do literary things. That was embarrassing because in those circles, it's low status to do literary things. That was also something I had to flip in my mind. The thing about doing this—and that doesn't have to be writing—is that instead of talking abstractly, or asking a question abstractly about bundling and unbundling, you can talk about theory for a long time. But it's so much more interesting to take a specific: How did Spotify unbundle and rebundle the music market? What kind of consequences did that have for smaller artists, larger artists, and labels? And how did people. You start, and then you realize there's so much more detail to this unbundling, rebundling thing. Then you look at how it happened in some other industry or in your life, and you notice that it's much more complicated than the theoretical framework. Often when that happens, when I write pieces, I'll start. I'll just put out a thought: a mental model or an explanation for how something works. Then I'll try to think of examples of that. I try to think through things in a lot of messy details and look for case studies that do not fit the pattern. **That's one game:** Just go look for case studies, look for really messy examples, and think through those. It's okay if you can't formulate it into any neat framework because usually, if you start looking really closely, that unbundling, bundling framework would break down because it's too simplified. I haven't done that exercise, so I don't know what the alternative is. Sometimes you'll find another mental model that comes out of that, and sometimes you'll just end up with some vague intuition. That's a useful way of turning toward more messy examples. Another thing is what we've talked about all the time: just articulate what you think. It's really interesting in conversations. You could lock two people—that's basically my marriage. You lock two people in a room for five years, and they talk to each other. There's almost no external output. Johanna and I spent a lot of time together, and it's so interesting. You can have just two people in a room for years, almost, and it keeps surfacing more and more information. It doesn't stop because you get into this loop where, you and I are talking here, you will say something, and I'm going to react to it. If I'm able to surface my genuine reaction and my genuine thoughts, then you can react to that and say, "Well, I actually have an example that doesn't fit what you said," or, "No, you've misunderstood me." It's always so interesting. If I'm talking with—this happens mostly with my wife—she'll say something, and I'll say, "Oh, did you mean... Oh, you're saying that?" And she says, "No, I didn't. What?" These ideas looked the same to me, but they're not. What? Then there's a crack, and now I'm confused. What? What do you mean? Then you can spend two hours trying, going into that crack, and things will. There'd be a lot of information and surprise and complexity just staring toward the situations where you get confused or wrong. It's so common. People say something, and you get confused, but you assume you know and just keep talking. But if you stop: "Wait, what did you say there? What?" And you do that. Then you try to be like a dog sniffing for all the times you're confused or wrong, trying to rearticulate and surface all that so other people or the world can react to that. **Jackson:** It reminds me, I'll be listening to these interviews back while I'm editing. I think a lot of times I do a good job. I've generally improved as a listener quite a bit over the last 10 years. But sometimes I'll catch myself and realize, "Oh my gosh, I wasn't listening there." I traversed into the thing I wanted to say. Only hearing it back a second time do I realize, "Oh my gosh, they were saying something so different." **Henrik:** That's an interesting exercise you're doing. I've been on a bunch of podcasts now. It's really interesting to listen back, and you notice those sorts of things. **Jackson:** Yes. **Henrik:** There, I'm actually missing. Then you can start, or I do at least: I listen and think, "I'm going to practice that next time. I'm going to not do that thing. I'm going to stop longer." You get this feedback by creating a feedback loop, as you're doing when you're listening back. **Jackson:** Tracing those groups. There's also a degree of it being easy for low-resolution things to be predictable when you're dealing in low resolution and abstraction. It's easy and predictable to go back to the first thing you were saying. When you dial up the resolution, it turns out there's way more, including way more that will be surprising. That is what you write so well about: we're really good at doing the thing you said with Joanna—"Oh yeah, I got it. I got the shape of what you're saying. I can make out the picture." ## [01:04:16] The Role of Ambitious Goals in the Context of Unfolding **Jackson:** My last note on this theme: You have this line that I've quoted to many people since reading the piece: "The opposite of unfolding is a vision." This sense of "if only I was in another context" comes up a lot, which is this idea of the vision. The idea that, "Oh yeah, life would be so great if I lived on this Danish island instead of where I live now." Or "life would be so great if I was a writer and didn't have my job," or "life would be so great if I quit my job and traveled the world for 12 months." I think you very rightly disassemble the virtue of the vision, at least in the pie-in-the-sky sense. But I also don't think you discredit it entirely. What role do goals and vision play, and how do you use them in this loose-grasp sense? How do you use them to still provide some sense of long-term direction? You're an embodiment of this unfolding, and yet you don't seem to be someone who doesn't think about the future at all. **Henrik:** That's something I think a lot about. It's one of the parts of that essay that I feel is a little bit unresolved in my head. It could well be that I just am not very good at setting goals. It might be a skill issue that unfolding works well for me because it's the only tool I know how to do. **Jackson:** Because I see you and Gagosian in totally different ways. **Henrik:** I think about that now I'm writing full-time. Maybe I should have another goal. That was a goal, in a sense, that I wanted to write full-time. Now I'm doing that. What should I do now? I find that really hard to articulate because all the things that come to my head feel silly. "Oh, I should have more subscribers." I don't care; that's such a boring goal. "I should have more money." Who cares? What would be an exciting goal? I find that hard. Maybe that's a skill issue for me. I do think goals, lightly held, can help prioritize. When you're unfolding, when you're moving through life, there are so many opportunities, you have to have some way of rank-ordering them. I think of it that we have a value structure. We have some sort of utility function in ourselves that helps us rank-order things if we tune into it. That utility function is a very complex thing which has our ethics, our curiosity, how we're wired. Goals are a part of that. You're sitting there, there are so many things you could be doing, and you have to pick one or two or three. Goals can really help there. There's obviously something too. I've chosen to limit my life. It's not exactly the same thing as goals, but I've limited my life, so I focus very much on the writing. I've mostly given up music; I've mostly given up programming. That's obviously because, in some sort of goal sense, I have the idea that I could become a good writer if I do that. I realized being a good writer is more important to me than being a good musician or being a good Programmer. So that's some sort of goal. That helps create a coherence that I get more rapid feedback loops because I'm obsessing and being very monomaniacal about it. Goals can really help in that sense. There's also this idea—and I have no experience with this, but I see some people who have that skill, some really good startup people—where they're able to articulate these really fantastic, extreme goals. "We're going to go to Mars," "We're going to build AGI." The cool thing when you have a goal like that is that you can do reverse induction. You start, "Okay, if I want to be on Mars in 2040, what has to happen in 2039? And for that to happen in 2039, what needs to happen in 2038?" That can really... if you then roll all the way back to where you are now, then you realize you should probably be doing something radically different. That maybe looks really strange. Maybe you roll all the way back and figure out you should become a stamp collector or something. **Jackson:** Also, decisions today compound very hard over a decade or 15 years. Say what you want about Elon, he's very good at this. **Henrik:** : It's something I've been playing around with in my head: could I learn how to do that? But I don't know how to do it. Sometimes I've thought, maybe I should do an opera. What would have to happen for me to make an opera in five years? I don't know. But I haven't found a goal that... **Jackson:** That resonates with me enough; it makes a lot of sense. I think this applies in really big-scale ways. Also, last year my goal with running was to run more or run a couple of times a week. This year, my goal is to run the marathon. That is a very different goal. And I don't think, to your point, it's always helpful to have that level of specificity, but it can be very empowering, if only on the notion of belief—of knowing the direction I want to run. It's a little bit clarifying. You said your goal is to write a few good essays, which in some senses is vague, but I think you also know what you mean by that. **Henrik:** a clear point. **Jackson:** On the horizon, which I think is powerful. **Henrik:** Yeah. ## [01:10:06] Hampton ## [01:11:41] Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible **Jackson:** We spent most of the conversation talking about this self-cultivation idea across a whole bunch of different frames. I now want to talk about other people in the world, the external world. I want to start with the name of your blog, Escaping Flatland. You say Flatland is a reference to Edwin Abbott's 1884 novel about a square who lives in a two-dimensional world and makes contact with the sphere from Spaceland, the three-dimensional world. You go on to say: "I now recognize a deep longing in this name. To escape Flatland is a dream of making contact with people and ideas that could expand and alter my understanding of reality into something richer, more full, more roundedly human." What does it feel like to collide with a sphere, whether a person or an idea? **Henrik:** : It's a continually evolving situation. It's been a very strange journey for me. I started writing almost to the day four years ago. Looking back, I realized I was so lonely. We'd left Sweden; we didn't know anyone. It was this very dark night of the soul kind of place. But when you're in a place like that, you can't really admit that to yourself. You have to just keep working. And I did, and then started to bring people into my life. I've made friends with people I used to admire. There happens several things with that. There's the validation. I met people who were like, "You are so radically underestimating yourself." And I was like, "What do you mean? Tell me more about that." Changing the context of people that I was interacting with really changed my ambition and my level at how far can you take this project of trying to be yourself and a good person. You realize because you live by the sort of references of people you've seen. I've met some amazing people in my life. But when you meet someone who's pushed to the very edge of thinking and writing, for example, you're like, "Oh, that's something else. I didn't even know that league existed." And that can be like existence proof. You realize that could be done, and that's sort of a goal too. You can look at these people and you're like, it's possible to become like that if I keep doing this for 15 years. So that's a really, to get like a high-resolution image of what kind of character you can cultivate. And then of course, there's all sorts of tacit knowledge. It's so useful to get to talk to people and get pointed feedback. I have a writer I used to admire, I still admire him a lot, and he can sometimes write fairly nasty emails to me, but from a place of love. It's very direct with me, just giving me that sort of feedback. And to get hard, direct feedback from people you admire and who are at the very peak of the game, that's a very high-resolution signal. It really kind of transforms and just created this kind of motivation and momentum. So my inner world feels like 10x more high-res. My thoughts and feelings feel much more high-resolution, and my capacity, it's just a very interesting internal experience because self-writing is this kind of self-cultivation thing. The project I'm doing is basically turning myself into a certain type of person who is able to have these thoughts. The essays are kind of just exhaust from the project. The work is growing emotionally and intellectually in such a way, and just going out into the world, talking to people, reading, looking at things, and becoming the kind of mind that can have these thoughts. That's the real work. And again, you don't know what you don't know. I was curious. I had a rich, wonderful life before too, but just, oh, there's another level that I didn't even know. **Jackson:** Another dimension, the metaphor. **Henrik:** Exactly. That's a part of it. But the beautiful thing too, where I feel I'm at in this stage now, perhaps since I started writing full-time, is what I jokingly call the current era of the blog: return to Flatland. I went out on this big journey of trying to prove myself, meet my heroes, and go on an adventure. I grew a lot from doing that. Now I turn back. I just came back from being with my grandfather, and I return to my village where I grew up. I turn back to my parents. I reappreciate that from the space of having become the kind of person who can more richly appreciate the beauty of the everyday life around me. I really love Flatland now. **Jackson:** That reminds me of many things, sort of combining high and low at the same time. There's a little bit of that in there. You've said that you can shape yourself by reshaping your relationships. **Henrik:** An important part of that, to get back to Flatland, is something I appreciate more and more. There's this naive, good first approximation to that idea, which you see a lot on Twitter: you're the average of the five people you have around you. That's a good first approximation. But what I realized more and more is that you're the average of the five persons you interact with. By that, I mean it matters how you talk to them. You can have the same five people around you, but if you change how you talk to them, suddenly you have five new people around you. It's not necessarily that you need new people; you might just need to interact with them newly. **Jackson:** That's really interesting. My next question was going to be: what makes someone a sphere or sphere-like? You have a list in that initial piece where you're listing off various friends and influential people. Perhaps a better version of that question, which ties into another piece you wrote about your friend Torbjörn and how you saw him differently, is this: what goes into it? Perhaps the person who's a sphere to you is not a sphere to me. having relationships and interactions with others that actually expand you, increase your dimensionality, and cause them to shape you deeply? **Henrik:** There will definitely be some people who are more sphere-like. To use a silly metaphor, there are different states of matter, and you can have phase shifts between them. People also have different states. You can phase-shift a person, so someone can be a square, and then you can turn them into a sphere with the right prompt or situation. Certain people are much easier to make that phase transition. They're usually quite secure people: open-minded, curious, outward-directed, and attuned to the world. For me, I've always felt it very easy to commune with artists, researchers, founders, and entrepreneurs—people who are in that mode where they are, I guess, genetically disposed to be interested in colliding with the world and being curious. Some people have that, and those people are quite easy to turn into spheres. They are basically spheres all the time. Maybe only when they're talking with the IRS do they turn into squares, but the rest of the time they're spheres. Some other people are squares almost all the time. But then maybe you're in the same space during 9/11, and suddenly they switch and turn into spheres. You see their full humanity, and a bond can be created, like bands of brothers, that sort of thing. **Jackson:** Environment matters a lot for many people. **Henrik:** It's really nice to find these natural spheres who are like that all the time because that's so easy, nice, and relaxing. But you can also get more skilled at inducing sphereness in people. That often comes from becoming more grounded and unneedy. If you feel very secure and you're not needing validation from other people, it's much easier to be open with them because you can share things. People are such good readers of subtle emotional cues. Maybe this is easiest to see in dating. When I met my wife, I was quite open, and we went really fast and shared everything really rapidly. In our context, she was holding the handbrake, but I was so secure and grounded that I was fine that she was holding the handbrake, and there was no tension. I was comfortable. I really, really like you, and it's totally okay that you're holding the handbrake. This can take a year. If you're coming from that place—because a lot of people will be afraid in that situation of showing that they care about someone. **Jackson:** Or we pull back when other people pull back. **Henrik:** Yes. Because I was generally: if she doesn't want me in her life, that's fine. She's just an amazing person. I want her to have an amazing life; I hope I get to be there, but I generally felt that way. When you're coming from that place and you say, "Oh, you're an amazing person, I want to hang out with you," then that's not threatening. **Jackson:** It's a little more abundant too. **Henrik:** That's an extreme example. But a similar thing goes on in relationships. If you come in and you're very confident and calm, and then you start sharing, "Oh, you have such a wonderful laughter." You just say whatever's on your mind: whatever you like about the person, or, "It doesn't feel like you're listening now. Could you just take five seconds after I've answered? Listen before you answer?" You can start saying all these things. When you're able to be more honest like that, you can induce sphereness. **Jackson:** That's a great answer. It's related. I have a couple of excerpts from the piece on Torbjorn that I mentioned. You say, "You can only ever know another individual if you meet them in open dialogue, if you treat them as unfinished, as capable of surprise. If someone seems boring to you or a bad fit, it might be that you don't know how to prompt them, that you haven't seen them react to the context that brings out their full being." That's a nice pairing with what you just said. In that piece, you described the most important friendships as being friendships of virtue, as opposed to pleasure or utility. I think pleasure or utility is the two other modes. On the note of how you convert people into being spherical: what are the types of virtue that are often more illegible? What does it or feel like when the light cracks through with those types of people? I am specifically thinking of how you talk about Torbjorn in that piece, but it might show up in any number of ways. **Henrik:** His big virtue is responsiveness, which is our attunement. He's totally there when you're in a conversation with him. It's very fast. He's really good at improv, throwing jokes, and that kind of verbal dexterity. As I talk about in that essay, I misread that as him being funny. Funny is nice, but I don't necessarily need funny people to be my close friends. I misread that skill or that virtue as funniness. There are other sorts of things, certain types of virtues, you can only see in adversity. **Jackson:** Yes. **Henrik:** You need to see how they handle when they really need to show up or when they're in deep pain. That can really change how you see a person. In those moments, a different layer of their personality shines through, and then you can never see them the same way again because there is this process running deep inside them. Now you've seen that, and now you know how to access that more. A lot of it is just seeing people in different and often hard situations can really bring things A lot of virtues are long term. A lot of virtues are things like trust, showing up, and putting in the work. When I'm writing online, I interact with many other people who have podcasts, or who are writing and blogging and doing things. There's this sense: the first time you talk to someone new, it's always fun when there's a new one on the scene and you check on them. But you're also like, "Let's wait two or three years." Because if you're going to do a good body of work, you just need to show up in hard times and good times. And you just can't know until they've... **Jackson:** Did they write one \*Looking for Alice\*? Are they still crushing three years later? **Henrik:** That's a common joke. We tell each other, "We'll see in 50 years." When I'm talking to other people who seem like long-term players who are really dedicated, you just can't communicate it. You have to do it for 10 years to show that you're that type of person. Even I, I'm four years in. You still don't know if I'm going to cash out at some point, or sell out, or do whatever, or give up. You don't know that yet. Four years is not enough. Let's get back in 10 years. If I'm still doing it in 10 years, that's going to say something about my disposition. **Jackson:** Reminds me of Visakan. Visakan has that piece on seriousness that I assume you've read. He talks about seriousness in the same way: the only measure of it is time. **Henrik:** Yeah. ## [01:26:53] Asking Questions that Push People Past their Cache **Jackson:** One of my favorite ideas I've called "cached conversations" or "breaking past the cache." You have this amazing anecdote in \*Looking for Alice\* about Herzog and the squirrel. It's this anecdote about how a priest is going to have to speak to a young boy who's about to be taken to be killed as punishment. He is going through the motions. Then he starts talking about the squirrel. He's prompted by Herzog to talk about the squirrel in this very authentic way that brings him to tears. And you say, "He is no longer saying versions of things he has said before. He's not protecting himself; he's just there." From that point on, it takes about 10 seconds before he's crying. If you want to prompt someone to be authentic and playful and generative, you usually need to ask them something where they have a rich experience to pull from but have never pulled an answer from that experience before. If you ask two or three increasingly detailed questions about something they tell you, you get there. I just love that. **Henrik:** : The scene you're describing is the opening scene from \*Into the Abyss\*. I think \*Into the Abyss\* is on YouTube, so I really recommend everyone go look at the first scene in that film. It's remarkable to see that switch from this surface-level, cached talk into genuine interaction. And the way it comes from surprise. It's such a beautiful scene. **Jackson:** The way you frame it, too... I've brought this up in so many conversations. People don't necessarily have an intuitive sense of what makes a truly great question. A truly great question, as you say, allows for someone to pull something. It's actually quite easy for them to pull, but it's also new or surprising. Anyway, my question is: Who, outside of Johanna—I think it would be a little unfair to use her—is best at pushing you past your cache in this analogy or getting you to pull new things? **Henrik:** : That's an interesting question. I do try to talk to a lot of people. I really like talking to people. I talk to a lot of people I meet from my blog, and it's always interesting to see where the different conversations go and what people are resonating with or struggling with. I'm trying to bias toward talking to people from Nigeria or Vietnam. It's fascinating to me to talk to people from radically different lives and connect over ideas. Everyone has something they're bringing out. Every conversation is unique. It's really interesting to move between different conversations; it's always very beautiful. But there are obviously certain people who have a really good skill. Alexander Obenauer and I have a conversation like that. He's an independent researcher, and we just end up in really interesting, strange places. But it's interesting. Everyone is a different flavor. His flavor is very different from Johanna's. And Torbjorn, my best friend, is also like that, also a very different flavor. Both Alexander and Torbjorn are more "yes, and" people. I go to them and talk, and they're really excited, and their brains go in interesting directions. I always end up with a bunch of new ideas. Then I go to Johanna, and she'll take a hammer and smash half of them. So you need to have different people for different things. It's hard. It's unfair to compete with Johanna because we've spent 12 years or something building up a certain trust. She's also wired in a strange way, so we can have such brutal conversations with love, which you can't expect. I can't expect you to go at me like that. And maybe I'd leave the room if you did. **Jackson:** I hope we can all find something like that, the pressure cooker. ## [01:31:12] Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet **Jackson:** One other part concerning other people that you've written extensively about the beautiful metaphor of whistling in an orthogonal direction—put another way, like the bat signal on the Internet. You've framed the Internet as this beautiful niche-matching machine to find your people. You have a few excerpts. You say, "The Internet had rearranged itself around me." And then, "It is crazy beautiful to have a stranger arrive in your inbox, and they're excited by exactly the same things as you. You start dropping the most obscure references and they: 'Yeah, read that. Love it.'" "The first handful of times it happened, Johanna asked me what was wrong. I was crying in the kitchen. Those were tears of homecoming." I've asked you a few questions in this vein, but what does it feel like, or why is it so beautiful to be seen or known by strangers on the Internet? **Henrik:** The strangers are people. There's something almost a little bit like 9/11: when you're close to someone, that creates a bond because you have a really complex, in that case, painful situation. That is a shared context that is luring out a lot of humanness from you. Something similar happens, often in a more positive vein, but not always. Sometimes it's really dark stories I bond with people over. I get a lot of email from people talking about their wife dying of cancer. I get a lot of things like that too because I write about relationships, and I guess I sort of project that I'm the sort of person you can tell about death in the family. When you have a rich, shared, deeply human context, either a tragedy or a certain old poet that you both loved or similar ideas, that's such a rich context that lures a lot of humanness. It's like you're jumping straight into having these very deep conversations. You and I right now are in the deep end of the pool, and we've known each other for what, two hours? There's something really beautiful about jumping straight in. In most situations, it just takes a long time to get there because you have to build a lot of context. Maybe after five years, you can have those conversations. But there's something really special about that. There are also two things. With people I've met through the blog, first of all, we kind of assume that we'll probably never meet in real life and our lives are not getting intertwined. So you can tell everything. It's like I'm their therapist and they're my therapist. We just say everything because it can't hurt us. There's no risk. That's another lovely part of it. **Jackson:** Well, don't get catfished. But yeah, otherwise. **Henrik:** Yeah. I don't share as much as people share with me. **Jackson:** Beautiful though. Think about what a service that you can provide someone who doesn't necessarily have someone else they can talk to. **Henrik:** Wow. No, I really hope that. I know a few people have had great benefit. It can just be basic things you just don't know. I'm in a different situation. I've met and talked to more people and can just tell them, "Oh, you could go to that place or talk to that person." You know, there's something less wrong for people like you. **Jackson:** Yeah, here's your blind spot. **Henrik:** Just some things that are really easy and obvious for me to say can be really helpful for another person. Then, of course, there's something a little strange that happens. Everyone who reads my blog is basically a version of me. You're almost like me; we could be cousins or something. That's such a strange thing. Everyone I talk to through the blog is basically like me. They know so much about me because I've written way too much about myself. And that just means there's this immediate camaraderie where we can assume so much about each other. **Jackson:** Yeah. **Henrik:** It makes it very easy to just go really fast in interesting directions. **Jackson:** Yeah, it's like you get to start at a much higher level, at least in some ways. Obviously not in all. It's not going to be the same as someone you went to school with, but it's almost like different modes of knowing. **Henrik:** Exactly. To clarify, this does not require that you have a pretty big blog now. It doesn't require that at all. Thinking back to it, at the point where I had maybe 70 subscribers, I was almost already filled out because there are only so many people you can talk to. By the time I had 70 people who read my blog, there were five really cool people among them, and some of them I still talk to. I would have been fine at that level. The big life transition for me happened at 70 subscribers. So you don't need to go to ten. Reminder: I had, what, four blog posts and 70 subscribers. So I think it's a very low bar. it's the same thing: if I'm going to talk to people, I have to prioritize who I talk to. If you have a blog, even if it's just one post where you have listed your favorite books—so few people do that. But if I'm going to decide between, say, 10 people who want to talk to me, and one of them has written a pretty interesting blog post about how it's to grow up in Sri Lanka and they have good taste in books, I'm going to go with that person. **Jackson:** Yes. There's a guy you mentioned somewhere, C. T. Nguyen, and he writes about games and agency. He has another piece on the way that different communication mediums totally collapse or expand context. He gives the example of a teacher in a classroom who says something to 30 students: 29 eyes glaze over, and one of the student's eyes light up. There's so much fidelity there. Compared to a tweet, you could have 300 likes, and it means that 300 people thought it was mediocre-plus-one. Or you could have a tweet with three likes that three people totally loved, and no one else cared about. And that's not packaged in there. I think you do an amazing job of writing about why blogging specifically, and Substack specifically, are so powerful in the opposite way, in terms of enabling or empowering niche. You've called part of what you've tapped into a "subterranean Internet," which I think is a beautiful metaphor. Then, in your classic, iconic post on "A Blog Post is a Search Query," you say you write to find your tribe. You write so that they will know what kind of fascinating things they should route to your inbox. If you follow common wisdom, you will cut exactly the things that will help you find these people. What goes into this ability to embrace niche and writing with a really intense amount of detail that produces—you either write it, or at least I felt it, like—this image of one person jumping out of their chair as they read your blog post? You so clearly do that. You've written about the method of that, but that's so not intuitive. Most of us are writing for the imaginary large audience. Why is niche so important? **Henrik:** It's hard for me too. In some sense, it's even more so now that it's my job, because there is an obvious tension between being precise and going deep, and getting a large audience and a lot of these superficial metrics of success. Some of them are not superficial, like funding. If I got super into Ingmar Bergman's diary and decided that the rest of the year was only going to be about Ingmar Bergman's diaries, that would be pretty fun for me and probably 100 or 200 people. But I would have to get a job because I couldn't do that. There are obviously tensions like that, and it's not easy to navigate those things. You try to always err on the side of being too specific and going too far to compensate for the fear that people will laugh at you, or you're going to only get two likes, and all those things that can be socially awkward or painful. The way I try to think about it now, because I'm in hard mode of this since I need to write things that people want to support financially, makes it much harder. If I had a job, I would do a year on Ingmar Bergman's diaries, but I can't. So I have to try. The thing I try to do is, at every step of the way, trade away more and more growth. At some point, I needed some growth to get to a place where I could fund it. I don't have a good salary, but I have a salary that I can live off now. If I were to work equally hard and grow as fast, I would have two salaries in two years. I don't need two salaries; that's pointless. I still want to have a little bit more money so I can put away some retirement savings and so on. But mostly right now, I'm trying to trade off more and more toward: can I, on the margin, switch to being more and more obscure, like doing the Rage Ahead career arc? In five years, it's going to be a full year on Ingmar Bergman's diaries. It will come eventually. You can always trade those things because as a blog grows, you get more degrees of freedom. Then I'm trying not to trade those degrees of freedom for money or status, and instead trade them for doing weirder shit. **Jackson:** But on some level, it's all relative, but you are already doing something quite a bit more niche than the average person. Maybe that's the shape of Substack and the nature of the medium. But I would argue some of what has made you successful is that it isn't so generic. **Henrik:** Definitely. I very consciously avoided the best practices. That has cost me things, like having a cadence. **Jackson:** You could write some more lists. Substack loves lists. **Henrik:** I could. If I wrote a list a week on only love and relationships, I'd be… **Jackson:** We'll know. We'll know you're buying something nice for the family when you start doing relationship lists. **Henrik:** Yeah. **Jackson:** You have one other bit about this where you talk about the topography of the Internet as a river flow, a grand river delta. You say that this is what online writing is at its limit: the summoning of a new culture as well. I might be reaching here, but do you have a sense of either where in this river you sit, or, if not that, what culture you are a part of summoning or creating? What is the place of the Internet? Where on the map of the Internet are you sitting? You're in this interesting place of Substack, and you tapped into parts of LessWrong and stuff like that in the past. Maybe that's not the right way to think about it, but I'm curious if you have any sense of proximity. **Henrik:** I am a child of the rationalist movement in a sense, and I've branched off from that. I think a lot of the way the internet works, and when you're growing your subscriber I'm growing. You start in proximity to some place. You have to find where people who are almost right are. Ideally, you find some place which feels like home already. Someone's already built it, and you can just go there and contribute, write comments, or guest blog. That's the ideal world. But usually, most people are not exactly the same, so everyone needs a new place. I like LessWrong, but I'm not exactly a LessWrong person. The more I lean into the way I'm not, I think a lot of people would look at what I'm doing and LessWrong and say, "What? Are you from there?" It doesn't look the same at all because I've leaned into what I'm doing. That's evolved over several years into something that's very different from the average LessWrong post. But you have to start somewhere because you can't just scream into the void. It's really nice to find, "This is almost where I want to be. This is like a cafe on the internet where people hang out. I can start here, and I can make connections and friends, and it will snowball from there." You attach yourself to a big node in the network. If you are a weird person like I am and like to put a lot of your thoughts online, you will start to grow into a bigger and bigger node. You'll start pulling in people from all sorts of places, and you yourself become a node. If you are really careful and avoid audience capture and optimizing for stupid things, you can turn that node into an expression of yourself, but also a creation engine for yourself. **Jackson:** Yeah, yeah. Your own little island. **Henrik:** It's an autocatalytic process where I'm pulling in people who tell me things, and we mirror each other. This is radicalization in a sense, but in a good sense. You find like-minded people and you become more confident and radical in your positions. Hopefully, those are sound positions. Eventually, I've grown to the size where I'm starting to feel I'm, to some extent, having an effect on some people. There are a lot of people who read, and some of them are going to take what I'm writing seriously, sit and think about it, and then maybe make life decisions based on it. There's a certain responsibility that comes from that. I have to think a little bit more about what kind of culture. This is my corner of our civilization, and how do I want to tend it? One of my role models is the Idiot from Dostoevsky. I want to be the Idiot. He must be autistic or something, but he's this very Prince Myshkin. He is a character who comes to Moscow or St. Petersburg, and he's very optimistic, attuned, and sharing. He's not involved in the power games or anything. It becomes chaos because he crashes into everything, because he's just so pure and naive. I'm not that. He's like a Jesus; he's a version of Jesus. I don't think I'm Jesus, but I think it's a good North Star of trying to be that naive person. The Internet is so jaded. Trying to be a person who says, "I'm okay with being stupid. I'm okay with loving the world." I'm going to say things, and I'm going to have people throw eggs at my head, and I'm going to turn the other cheek to it. Being that kind of person. That's such a human way of being: very open and loving toward the world. Because of the dynamics of social media and so on, it's not a natural role to take. The natural path is to become jaded and calculating and all those sorts of things. That can create a very perverse culture if you're on Twitter a lot, and everyone is very calculating and everyone is seeking outrage. That can give you a very jaded perspective on reality and help you internalize some really nasty values. Trying to not become jaded, trying to not be pulled into this and try as hard as I can to just be like a normal person who likes to play and who loves my kids. Trying to remain as complex and roundedly human as possible as an end in itself. I think that's an important cultural thing. We need to have people who are complex and not jaded or calculating. I think that's a way of caring for your corner of the culture, to just be that sort of person. That's what I'm trying to be. **Jackson:** There's some "maybe this" energy in that, rather than "not that," which the Internet is pretty defined by. ## [01:48:55] Ruthless Prioritization and Making Time to Get Better **Jackson:** I can't remember which essay I found it from, but you talk about what you've done and making time to expand yourself. You say, "I can't strongly enough recommend setting off 20 hours a week to work on a project that forces you to learn and grow and meet new people. Most of us are awake some 110 hours a week, so 20 hours is not impossible, but it adds up in a surprising way if you keep at it for three years. I feel like I've grown into my body. I feel 15 years older, in a good way." That's just a really beautiful way of framing what you do, what you've done, and what I think many people—what I've certainly benefited from, what I think others might too. It's hard. How could you have started this sooner? Put another way, do you have any advice for somebody who is listening and is busy but lonely and wants to take the first step to doing something like that? **Henrik:** It's a muscle. You have to just start doing it. You can also think about it software that I'm writing. If you want the software in your life to have as one of its outputs that you spend 20 hours a week growing, you can put that on your Trello card. Then you try, and then you notice, oh, it's failing because of X, Y, and Z. Then you run a bug log. Then you look, okay, so I ran this a week, I managed to do five hours. I failed because I was looking at my phone. I was too tired. So next week I'm going to maybe lock my phone away. **Jackson:** Get a Nokia phone. **Henrik:** Maybe I'll get a Nokia phone. Try that for a week. Maybe I'm going to start working out a little bit more so I get the stamina to work in the evenings or in the mornings before work, and I'm going to try that. Then you do that for a few weeks and you bug log it. No, it still doesn't work because of this and that. Then you adjust, and then you adjust. Gradually, you reshape your life by running a bug log and removing the bugs. Then you build the muscle. **Jackson:** To our earlier combo, it starts with a goal. Or put another way, it starts with real, honest prioritization. **Henrik:** Yeah. **Jackson:** What am I actually willing to give up? **Henrik:** That's the thing. For me, the big thing was having kids. I'm talking to the people so you don't have to have kids before you do this. But once I had kids, I was like, yeah. Before that, I thought it was impossible. I could just do everything. I would say yes to everything. A party, that and that and that and that. I said yes to everything because it felt like I had unlimited amounts of time. I didn't, but I had enough time that it felt like I did. And then I went nowhere. Then I had kids. If I calculate really closely, I'm working, I have kids, I have, in the best of worlds, 20 hours a week that I could carve out for other stuff. Okay, so I own that. That's not much. Once I see that 20 hours, that's almost nothing. Then you're like, okay, so I can only do maybe, I can talk to my parents maybe every 10 days. Then I talk to a friend once a week. Okay, so now I have 17 hours left. Then I can only do one thing. Then I realized I can only do one thing. So then I'm going to write 17 hours a week. **Jackson:** But that starts actually with honesty. **Henrik:** Yeah. **Jackson:** About what? **Henrik:** You have to face that down. You can only do one thing. It's fine, whatever you want to get better at, cooking or whatever. But I think it's really nice to just pick a few things and do them well. Or rather, I think life goes through eras. There are going to be some eras where you're exploring. Then you should be clear about that. Say, now I'm in a phase. I don't know what my next chapter is going to be. I feel like I've been doing this thing for a few years. I'm still feeling stuck in a rut. Now I'm going to optimize for finding the next thing. So I'm going to try three new things every week, and I'm going to spend 20 hours a week trying new things, talking to new people. I'm going to do that for six months. It's good to be clear about what's the problem in your life and then using the limited resources to work on that. **Jackson:** Yes. **Henrik:** It makes such a difference. If you get reasonably good at figuring out what's the bottleneck, what's the real problem—I don't have money, I don't have time, I don't have the right habits. If you can figure out what's the biggest thing, and then you always work on improving one of your weakest spots, then you can move really fast. If you're addicted to your phone and then you get a Nokia, **Jackson:** Overnight, there's 40 hours. **Henrik:** : Overnight, that's a lot. Then you have all those hours, and you can start working on running and getting into a riding habit. It becomes this positive loop where you get more resources and more time to put into things. It's so easy to get into these modes—I'm talking about myself. It's easy for me to get into these things where I tell myself that I'm working and I make up fake bullshit things. I'll think, 'Maybe I should change my color background on my blog,' and I'll sit and spend three hours doing it. **Jackson:** Try a new note-taking tool. **Henrik:** : Is this really the bottleneck in your life right now? Usually, the bottleneck is painful in some way. If you can—and you don't need to spend every waking hour working on the bottleneck—but if you make some progress on the bottlenecks; if the bottleneck is your discipline, if you get a little better every week on that thing, then you solve that bottleneck. Then the bottleneck is something else, and you move to that, trying to be a little bit brutal about: 'Now I'm just doing bullshit work, and the real thing I should be doing is this.' **Jackson:** Anytime you have pressure on either end—either the end of constraint, deadline, necessity, or pressure on the end of how bad you want to do something—it starts to happen. That was true of what you're making. **Henrik:** : That's one of the good things about meeting interesting, cool people that I've met through the blog: you realize a lot of the stories that I've been telling myself are bullshit. I used to think, 'Oh, I need three months to write an essay.' No, you don't. You just don't have a good method. You there is a 10x improvement in most domains that could be done. It's really nice to see that could be done. Once you see it, you think, 'Oh, wait.' Then you did a backwards induction: 'Wait, how could I write an essay that is the best essay I've ever written, but write it in three days instead of 30 days? What would need to happen for that to be true?' I think I'm getting close to that. I used to need—if you look at the first year of the blog, I had a baby then also, so I should blame her—but I wrote five or six pieces. Now, I'm going to write maybe 40 pieces this year. So I'm making progress in building that muscle. You realize I have some more time, but it's mostly the muscle. It's mostly that I've optimized my prices, I've grown, so that's at least a 5x improvement. The pieces are better, too. I write them five times faster, and they're at least twice as good. So the roof is high. ## [01:57:05] Initial Spark and Connecting with People **Jackson:** One of my favorite pieces of yours, the first I ever read, \*Looking for Alice\*, is where you talk about meeting your wife and give some good advice for finding a person rather than a category. Just one excerpt from it, you say: "That is perhaps the most solid dating advice I have, by the way. Show the inside of your head in public so that people can see if they would like to live in there." The type of person I'm assuming we're looking for here is: one, someone that you will find fascinating to talk to after you've talked for 20,000 hours. Two, you feel comfortable with them talking through the hardest and most painful decisions you will face in your life. And three, the conversation is wildly generative for both of you, and that it brings you out, helps you become. I think so much of other stuff we were talking about earlier in the conversation hits there. My question here is perhaps a little bit selfish, which is I'm single. What does this feel like at the beginning? And how much do you think about the initial spark and excitement? Put another way, how obvious should it be? There are people, maybe along the lines of what we were talking about earlier, who take much longer to see them in the ways that really make them shine. But at least in this context specifically, and it seems for you it was pretty quick and obvious. I'm curious how you think about that. **Henrik:** Later pieces I've written, like the Torbjorn piece you mentioned, try to compensate. I notice some people read \*Looking for Alice\* and take away: just find a Manic Pixie Dream Girl. And everything's going to be magic, you deserve everything, and you shouldn't work at all. That's not the point. For me, it was obvious. It wasn't obvious for my wife, so I'm an example; then she was. And it goes back to, it's interesting, the thing I quoted about showing the inside of my head. What happened was we met in a bookstore. I fairly quickly figured out that she was really cool and interesting, and she didn't understand that. I guess I was doing the usual thing—the way you talk if you meet someone in public. And I guess I was trying to be courteous and funny, and I didn't show other sides of myself. Then she read an essay I wrote: a really long essay about a poem by Adrian Rich, which is a very nerdy topic. It's a very emotional and deep piece. And she said, "Wow." Yeah, I bet it is. It's in Swedish. It's in a magazine somewhere. Then she realized; she saw a different perspective of me. Because if you meet someone—say, we'd run into each other in the supermarket—you won't go into a 15-minute monologue about poetry. So she didn't have the chance to see that side. That's the good thing about writing things down: it's giving people the space to go into your head at their own leisure. And if they want to listen to what you're saying, you can be super obsessed and deep in a way that you just can't be with strangers around town. That's a really useful thing. But that was a side note. For me, it was obvious with her. But as I said, with my best friend, that took me 15 years to figure out. I think it really can. It's a skill issue. I think I had built a muscle when it came to romantic relationships at that point. And I guess I figured out that Torbjorn, my best friend, was cool around the same time. So I guess I had matured. **Jackson:** More to do with you than them. **Henrik:** I had matured into a certain level of capacity of reading people. During my poet year, I was out doing readings. When you do readings, you're going around shaking hands and talking to people. I was on stage; maybe I did 100 or 120 readings. Let's say I talked to 30 people at every reading. That adds up to 3,000 people I had talked to, and then in other contexts too. I went around exposing myself to ridiculous amounts of people and talking. Since it was poetry readings, it was a little bit like the blog because I went up and read very emotional, deep, and intellectual poetry. Then I had these deep conversations. I got a lot of training data during that time where I was just talking to people. It gets back to what we talked an hour ago about intuition. I talked to enough people that I was building the muscle, the skill to pattern match. When I met my wife, I only had to speak to her for five minutes to notice the way her face looked when she was thinking, that she was really listening before she articulated a question. I thought, 'That's rare. Another really good trait.' When I was 19, I wouldn't have noticed that. I don't think I could have put words to it then either. But I had talked to enough people that I could notice that was a good sign. I could notice that her questions were very specific and trim to what I was saying, and all these sort of subtle things and subtle cues for kindness. Some people know how to do this when they're 12. I figured out how to do it when I was 22, which was probably pretty fast. It depends on skill, and it depends on what kind of virtues you're drawn to. Some people will be easier than others. I don't think you can necessarily tell right away if you don't know what it's supposed to look like. You might need more time. But the simple and boring answer is to just talk to a lot of people in a non-goal-oriented way. Go around and talk to people, like you're doing here. Us talking right now probably helps on some part per million. **Jackson:** More resolution. **Henrik:** Yes, getting some. Go around and talk to people. I think a mistake people make is they go around in a too goal-oriented way, and you just evaluate: "Is this the right person? Does it check my boxes?" **Jackson:** Yes. **Henrik:** That doesn't matter; it's totally irrelevant. Ask, "What is this person like? What's going on with this person here?" Just be curious. Because if it's the kind of person you should date, you'll notice that too. You don't need to look for that. You'll notice if you just go around and are curious: How's this person feeling? What are they into? How can I support them? If you do that to every old lady and every kid and everyone. **Jackson:** Yeah. **Henrik:** You do that over and over again. One day you're going to talk to someone, and you're just going to be supporting them in conversation and being curious. And then, wow. Maybe it's the first time you talk to that person, or maybe you just enjoy talking to this person. It was really cool. We booked another meeting. I'm going to coach them on leadership or whatever. And then you talk, and that's also a good conversation. Maybe you do that for four months, and then you figure out this is actually someone I should date. My best friend from high school had somewhat bad taste in women, so he struggled until sometime in his early 30s meeting different people. It always ended up being very dramatic relationships that fell to pieces in dramatic and painful ways, so he didn't know what to look for. But then eventually, he was living with a roommate. They lived together for three years. And she wasn't his type—that dramatic type. But she was. They really liked each other. They started working together and had such humor together. He was just so stupid about it. And everyone else started talking, "Why are they not dating? Are they stupid?" And then eventually, after three years, now they're dating. **Jackson:** Blind spot again. **Henrik:** Yeah. **Jackson:** You have an amazing little story in one of your pieces about the daughter of, the mother maybe of Heli. Or maybe Heli was the... **Henrik:** Heli is the daughter. **Jackson:** She, after 20 years or something... **Henrik:** Yeah. **Jackson:** She and her friends she got dinner with went on some trip and found. Many such cases. **Henrik:** Yeah. I think your answer is you don't know. She just talked to people. **Jackson:** Be interested in people. **Henrik:** Yeah. **Jackson:** This is the other thing that comes through. ## [02:05:58] Collaborating with Henrik's Wife Johanna **Jackson:** You have a line somewhere, "As usual, the best ideas were Johannes." Why is she such a wonderful collaborator to you? **Henrik:** Our minds are similar and dissimilar in productive ways. We have very deeply similar values. That's really important; we both value integrity and an open-ended search for life and all those sorts of things. If we didn't, imagine me dating someone who wanted someone with a normal career—that just wouldn't work. So you have to have certain basic values together. But when it comes to our cognitive styles, we are very different, and that's a complementarity. I am more on the generative side. As we were talking about earlier, don't throw shit in the head of the person who is generating a new take. That's me saying, "Don't throw shit at me," because that's what I like to do. I'm really good at that. I'm always having new ideas. I'm too fast. But I'm also a bit credulous. You could probably swindle me on money if you wanted because I trust people. I trust the world. And that's a superpower in seeing things, in meeting people, and growing connections. She is more reserved, more analytical. I can't relate to it, but it's really cool. She will not have a stance on something unless she has thought it through; I can't relate at all to that. If I ask her about something, she'll say, "I don't know" about almost everything if she's not prepared. She'll say, "Do you want to know what I think about that? Then I'll have to go sit down and think about it for two hours. Is it that important to you that I have a take on that?" And I'd say, "No, no, you don't have to sit for two hours. I just wanted to know if you like the flowers." But she's like that. I saw an interview with Geoffrey Hinton, who was one of the fathers of deep learning, and he's like that too. He's for never letting anything into your head unless you've wedded it. You know that this piece, I trust this LEGO piece in my head, and that makes this very robust. You can build very robust structures. My way of associating really rapidly is kind of soft and mushy, and I use writing to hammer that. But I also use Johanna a lot. She is just very tuned into finding flaws. So we have that: I'm generating ideas, and she's evaluating them. **Jackson:** If you think she was listening in on this conversation, is there anything you think she would have most critically chimed in on, added, or corrected? **Henrik:** Oh, there's probably a bunch of things where she'd say, "Now you're just generalizing from a single case," or that something doesn't quite add up. She'd probably, in a bunch of places, say, "You're missing details here." I don't know. **Jackson:** I need one of those. That's a good person. **Henrik:** The thing is, I never know where those things are. If I knew, I'd probably correct myself. I've gotten better, so I'm correcting myself more now. But I don't know. **Jackson:** Well, if she's kind enough to listen, maybe I can get her notes. ## [02:09:46] Living a Barbell Live Inside and Outside of the Computer and Henrik's Scale of Ambition **Jackson:** You, in a sense, are living two types of lives at the same time. One is in some sense small, but incredibly deep and rich: this island life with your wife and your two daughters on a farm, pretty remote, with your Nokia phone. And then the other is big and wide: so much of what we talked about in this world on the internet, writing pieces that thousands of people will read, and maybe a niche, little corner of the world, sort of internet fame. It's highly social. What does that contrast look like? One, is that characterization even correct? And two, what does it look like? **Henrik:** : I think it's correct. It's a very sort of barbell approach. My Internet, it's probably 50/50. The part you see online, that's half my life. I put a lot of effort into what I'm doing with my writing, so it takes a lot of my mental energy. And that's extremely social, extremely out there, putting myself out. Then I switch off the computer and I go out into nature with my kids. It's really nice to have these. I like having very extremely barbelled situations. I have friends who are bloggers and they live in San Francisco. That to me sounds like, oh. Because they go out to parties and everyone knows them from their blog, and they all, oh, that sounds like. Because I go out, I turn off my computer, and then no one knows that I'll go talk to my neighbor about a tractor. **Jackson:** What do you say you do? Do you say you're an Internet writer? **Henrik:** : It depends on who I'm talking to, how strange I want to sound. Sometimes I say I'm a freelance journalist. If they don't understand it, or if it's old people, or I'm a rider. Yeah, it depends. I have various explanations, but mostly a lot of people are not asking that much. Usually I don't. I'm just that guy. I have my yellow bike that I ride, and they're like, it's that weird. Hopefully they think I'm kind. I ride around, talk to people. It's just like the guy in the village who used to work at the art gallery. I don't know. You don't have to. I've really tried. It's getting harder. I'm starting to have more people in my real life that know I'm a writer, and it's starting to bleed out because it's getting big enough. For a long time, it was just totally separate. No one knew, and that was really nice. Just go down and talk about tractors or things like that and just have that very simple life. It's a really nice counterbalance to the whole San Francisco super agency. Everyone is young, and everyone is going to build an AGI and buy a Galaxy when they're 40. It's just really nice to. I especially hang a lot with old people. That's one of my things. Probably most of my friends on the island are 70-plus. It's a very nice counterbalance to just have these conversations about life from someone who's lived for a long time. It's a really nice, really strange barbell. It's so interesting to just see those two worlds, and they are thinking about such different things. When you're hanging out with people who are in their 70s and 80s, all of their friends are dying, and they have opinions about how to have a funeral in the best way. You're not endured gossiping about funerals and stuff. It's a very different world, but I find it balancing to spend time in that world and not get fully caught up in that other world. **Jackson:** There's a thread there that I want to pull on a little, which is, it actually came out. I was listening to some other interview, and you were talking about Ioanna's gardening and how she was studying all the world-class gardeners. It made me think of ambition and the bounds of ambition. It's interesting to think about gardening, maybe specifically, and it sits inside the contrast you were just describing, which is it's small, at least in one definition. Yet she could absolutely, on your little island, on your little farm, build a world-class garden. It being world-class has nothing to do with the scale of its reach. Obviously, writing is not quite so simple in that way. But I'm curious how you relate to scale and ambition, maybe as those sit next to the quality of your work. **Henrik:** Quality every day. I need a certain scale so I can give my kids food and pay for a new roof on our farm. Beyond that, I don't think scale for what I'm interested in matters at all. There are certain things where scale matters. You need a lot of capital because you're building some AI or you're a car company. You need scale to get economies of scale. But that's not how it works with art and with essays. Now, when I'm at the point where I can pay myself a salary, scale does not matter at all anymore. The only thing that matters is the integrity of the work, how far I can push my taste and my skills, and the internal complexity of the objects that I create. I like the idea that it's meaningful for other people. I try to put some thought into making sure that it's a good experience for people and meaningful for them. But optimizing for that now—an average peace of mind is read by maybe 20,000 people. That's a lot of people. It doesn't matter if it's 30,000; another 10,000 doesn't matter at all. Why would I care about that? But if I could make pieces better, and hopefully downstream of that, the emotional and cognitive states that I induce in the reader become richer, more transformative, more useful, and lead to rippling effects of good lives. That matters. **Jackson:** I ## [02:16:48] Sacrifice **Jackson:** have a handful of lightning-round, miscellaneous questions before we wrap up. We've talked about it a bit. You clearly have a deep ability to focus and, inside of that, you've verbalized this as being ultimately about sacrifice. Does anything come to mind as the most painful thing you've had to sacrifice, at least within the bounds of choosing to prioritize and focus on the writing? **Henrik:** I don't think I've felt any genuine pain for the sacrifices I've done for writing. Writing is always second in order for me, after my responsibilities to my loved ones. When it comes to the kids, there I've made real, painful sacrifices. I'm very close to my grandparents; they're my best friends. We had to leave Sweden to homeschool to care for our kids. There was a real, painful tension between caring for my grandparents and caring for my kids. I chose my kids. So there, I've made real, painful sacrifices. But when it comes to writing, I've had a complicated life. I didn't have a car for four years and lived on a farm. I had a bike and biked and biked and biked to get stuff. I biked in so many snowstorms and things like that. But to me, that's not painful. It sucks a little bit, but it's not pain. Not painful the way leaving behind my grandparents was painful. I think a lot of people think that was a sacrifice they could never do: not having a car and biking for hours in a snowstorm. But I think they just haven't tried. It's not that bad. A lot of things that we are afraid of sacrificing are kind of okay. **Jackson:** Little conveniences. **Henrik:** It's not painful. ## [02:18:57] Pseudonymity and Playing with Identities **Jackson:** We were talking about it a little bit before we started recording. You have a great piece on pseudonymity: playing with identity can actually be a path to more authenticity, not less. If you had the time—speaking of which, you clearly don't—but if you had the time to pick up a new mask [to use your language] and write on some totally orthogonal topic for a little while with a different set of expectations, is there anything that would be fun, aside from the diary? **Henrik:** One direction where I'm going with my writing, and where I might be a little bit limited, is that I am trying to go more and more toward personal and highly high-resolution writing about my relationships and so on. There is a limit to how far I can go there because I don't want to be Karl Ove Knausgård and hurt my loved ones. That limits what I can do. Writing fiction or having a pseudonym where I could go into more painful things, or maybe write things that are painful for loved ones, would be one thing. I think that's probably an undersupplied niche: people writing with love in their heart and an intention for clarity and insight, but willing to wrestle deeply with the flaws and shortcomings of themselves and their loved ones in a very deep and serious way. It would be really interesting to read a blog like that. But I can't do it. I've been trying to push as close to that as I can. That's something I would love to do if I had the time. But now I've said it. Now if one arises, everyone's going to have to figure out who it is. **Jackson:** Now we know you're not Karl. I can attest that you are not. The Henrik Karlsson that you describe in the blog does seem to exist. ## [02:20:57] Self-Organizing Systems **Jackson:** It could have been a whole separate podcast, and maybe someday. But you've written and you clearly think deeply about what you call self-organizing systems and the way that framework applies to so many things, maybe especially education. You've thought a lot about school, both given your guys' backgrounds as teachers and now homeschooling your daughters. You talk specifically about interventions that strengthen the system's ability to self-organize, and that being the path to better systems. Why is self-organization so important to good systems in the broad sense? **Henrik:** It comes down to a Hayekian point: most of the knowledge in a system exists at the edges or at the grassroots of a system. If you're building an education system, there's going to be all sorts of knowledge that the child has, or that the parent has, or that the teacher who works closest to them has. Higher levels of the hierarchy just can't ever get that knowledge because it's too complex to compress. If you're able to design systems that can better leverage the information that can't be centralized, you are going to have a more efficient system. But there are obviously trade-offs, because there are things that are good about centralizing things too. You want the information to flow as freely as possible and to use as much of the information as possible. And self-organizing systems, when they work well... **Jackson:** Capture that intelligence from the edges. **Henrik:** Exactly. ## [02:22:51] Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold **Jackson:** I mentioned it briefly. You've spent a lot of time thinking about learning and education. Somewhere along the line, to tie it back to the unfolding stuff, you said school systems are centered around visions, not unfolding. It's a central critique. Open-ended, but maybe it ties in: What's the most important thing you've learned from homeschooling your daughters? **Henrik:** : There are a bunch of things I take into homeschooling that I knew from beforehand and are maybe obvious: you want to have concrete feedback loops with reality when you're learning. You want work to be meaningful, to interact with reality, and to run your own projects. That sort of thing, if done right, is incredibly powerful as a way of learning. A lot of people know that, and I knew that even before I had kids. Then it's a whole skill stack of how to do that well. But I'm not a big fan of sequential curricula where first you learn this. It's interesting; when they do accelerated expertise training in the military, they don't do it like that. They start with complex, messy case studies. **Jackson:** In the deep end. **Henrik:** : Then you're overwhelmed, and it's chaotic. Then you have to start to pattern match. Then, for certain things, obviously, you can do some deliberate practice on specific sub-skills and so on, but you can move so fast if you jump in the deep end. So that's something I have with me into having kids and trying to organize. **Jackson:** You also read pretty intense adult fiction to your seven-year-old or eight-year-old. **Henrik:** When Maud was three, when we just moved to the island, she came to me and said, "I'm looking at reading the human book." I asked, "What are you talking about? The human book?" Then she went out while I was doing the dishes. She came back with \*Spring\* by Karl Ove Knausgård. She opened it to an abstract green painting on one of the pages and said, "That's it. Look, it's the human." I said, "That's an abstract green painting." But then I asked her, "Do you want me to read it for you?" So we started reading that Knausgård book, \*Spring\*, which is a really good book for kids, actually. I think it's about a dad and his baby and a day in their life. They're wrestling with things, and it was really interesting to read. A three-year-old starts with Karl Ove, who wakes up in the morning, and the baby is lying in the crib and screaming. Our kids have never screamed at night, luckily, when we've had them co-sleep with us, so that was really alien. Why is the baby in a crib? Why is it screaming at night? What is the baby feeling that she's screaming? So we could actually have these conversations around Knausgård because he writes in this very concrete way. Now he's going into the kitchen, he's making tea, he's carrying the baby, and now he's putting the baby in the car, and they're driving. We were reading books like that. that was her idea to start reading that book. And that turned out to be a really fun, interesting challenge: how do I reinterpret Knausgård in a way that fits a three-year-old? But it was really interesting. We kept going like that. Now she mostly reads alone; she's seven now. She's reading the Harry Potter books, so she's getting pretty good at reading. The nice thing about reading hard adult books—we also retold \*War and Peace\* for her when she was four. It's a brilliant book for kids: princesses, love stories, and wars. It's a brilliant book for four-year-olds. Someone should write a good children's book version of it. But the nice thing when you do that is that you have to reinterpret it and vocalize the things that are between the lines. Because if I read it straight out, she won't understand it. So I have to stop and say, "Oh, I think he's writing that, but he means this." Or, "Well, I think what's going to happen now is this." When you're doing that, you're forced to verbalize all these strategies you yourself are doing, which can be really hard to explain to someone. Now, I think when she was five, she was at the level where she could perfectly understand Harry Potter, which is quite good for a five-year-old. But it was because she had apprenticed herself to my way of analyzing text. So she's doing all of those things that I was doing aloud when I was reading books that were ridiculously hard for her. Mostly, it wasn't something I pushed on her; it was just fun. She thought that was fun. That was her idea. I just like playing around like that. To get back to your question, what I've learned is that education really is a matter of culture. If you grow up in a culture of reading... Our daughter has grown up with us reading, writing, and obsessing about words all the time. So obviously, she is reading at a very high level really soon. We haven't really had to teach her how to do that. **Jackson:** Right. **Henrik:** So that means the thing to optimize for is to become a competent role model. How do we become the kind of person that will, by osmosis, turn her into the kind of person we want her to be? **Jackson:** You want her to apprentice to as well. **Henrik:** And that's a good forcing function to just deal with your own shit and grow. **Jackson:** You mentioned Steve Krause in one of the spheres, who I think you wrote about in part four of \*Looking Brows\*. I was browsing around, and he had a tweet recently. There's a notion that Harvard lectures being online and education being democratized or accessible is proof it is motivation that is scarce for learning. Krauss's argument was that this is totally wrong. It's not desire, motivation, or willpower, but positive contexts that are scarce. When you're in France, you speak French. When you're in Cambridge, you go to class. When you're at a hackathon, you code. We need to scale the right kinds of contexts to inculcate the kinds of brilliant people we want in the world. Krauss's argument made me wonder. It certainly shows how being critical of school can create a context you don't want. I'm curious how you create context, especially as you're creating multiple contexts for her. For example, she's learning at home, and home is different—she's not going into a school. And how that context changes between reading books, studying math, or studying other things. Perhaps that's something you don't have to think about because it's so much about apprenticeship. But I'm curious how, if at all, you think about that, or if it was a motivating factor in deciding to homeschool her in the first place. **Henrik:** It was, definitely. I don't think I had this language to talk about it at that time, but I definitely had the language of that—that I wanted to individualize what she's doing. Then gradually, I started to see it more as the project of curating a milieu. It comes back to this: many people think it must be so hard to homeschool and that there are so many things you need to do, but you don't need to know everything when you start out. It's the same thing we've been talking about all day regarding self-cultivation and unfolding. I am simply being her mentor in her unfolding. What I'm doing all the time is figuring out what her bottleneck is and how we can remove that. We put a lot of effort into cultivating Amelia where she would read a lot, and we would spend an enormous amount of time reading aloud to her, apprenticing, and doing all sorts of fun things. We were really disciplined about reading in front of her and all these things because we knew that if she could start reading on her own at a high level, that would free up a lot of time for us. Now we can just put it through Harry Potter, and she's happy for three hours. That was a big win for us to get over that. Now we've done that, so we don't have to think so much about reading for maybe a few years because she's doing well there. In a few years, maybe we'll go back and do a hardcore deep dive on note-taking systems or whatever. But right now, that's fine. Then we think about what thing, if we helped her overcome it, would make her life really powerful. We're always looking for the bottleneck. For example, we're not focused super much on mathematics. She's doing fine in mathematics, probably about a year ahead of her level. I don't think I've had a math lesson with her in two months or so because that's not a bottleneck. She's doing fine; it's okay. But with other things, I can see that if we could do a boot camp on her challenges, on things she's working on... If I can do a boot camp and help her overcome her big bottleneck, that's going to transform her life totally. And then again, and then again. It's just moving from bottleneck to bottleneck and amassing skills along the way. **Jackson:** That's a really powerful frame for what education, I think, could or should look like. Not a point to overdo, but one of the ways I think some of this LLM stuff could actually be really helpful for kids is actually an up-close person. Hopefully, they have a dad like you or a mom, but in some cases, it's amazing to have that kind of attention. **Henrik:** Yeah. ## [02:33:13] Writers Who Help Us See Ourselves **Jackson:** In one of your pieces about agency, being attuned to yourself, and introspection, you talk about writing as giving other people a service. It helps them see in you what they do not dare see in themselves, which I thought was really beautiful. Is there anyone who immediately comes to mind whose writing has done this for you? **Henrik:** : Of many writers, reading Thomas Transtromer when I was waiting for you earlier today. I've read him so many times. He embodies a certain kind of loving connection to reality, ethical integrity, and presence to life. I read him again and again as a way of revitalizing that part of me and growing that part of me. I can be a friendly, kind, soft person. Surprisingly, many of the authors I resonate with are quite aggressive. I get to experience that side of me. I love Thomas Bernhard, for example, who writes these crazy, over-the-top rants for 300 pages where he just hates on everything and everyone. For me, that can be so nice to go into that and get to experience and hold that feeling of "sometimes people suck," and just to sit with that and get to go on and on with it. All sorts of authors provide me a space for exploring different feelings and reflecting back. Sometimes it's just an emotional discharge. Sometimes there's a wisdom I could bring back, some concrete thing I could say. It's just so interesting with all these different perspectives. ## [02:35:13] Writing and Thinking in Swedish vs. English **Jackson:** We talked about it a little bit earlier, but I'd be curious for you to reflect on, across all three: writing, reading, and thinking in Swedish versus English. Obviously, so much of that was just a hurdle to overcome initially. **Henrik:** : It would be interesting to go back and write in Swedish. I sometimes write notes in Swedish, but I haven't written seriously in Swedish. It is the language of home. There's a certain earthiness, and it feels very different from English. English feels like a machine language. I think that has to do with the influence from Latin. When the English had such Latin envies, they modeled their grammar on Latin, which doesn't make sense, so the grammar is odd. It's added on top of the language, a logical system added on top. Swedish, whereas, is much more fluid and organic in its grammar. The words to me—and that might just be because it's the language of childhood—feel more earthy. It's an emotional landscape I can only access in Swedish. There's a certain sadness that English is increasingly the language of my thoughts. I'm training my brain to think in English because I'm writing in English all the time. But it's really interesting to be able to move between languages. Since I moved to Denmark, I can understand and speak Danish fairly competently. Danish and Norwegian are very similar, so I can do that. It's really fun that I can move between multiple languages, and they all have their vibe. There are differences. From your perspective, maybe Danish and Swedish would be very similar, but if you get down to the details, they're different mentalities. You can see the traces of history and the decisions made through history embedded in the language. You get a sense for the evolution of history when you look at languages. **Jackson:** Fascinating. ## [02:37:44] Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves - And Modeling That For Others **Jackson:** My final question. There's a section of one of your pieces where you talk about a commitment you and Johanna made a long time ago. You say, "In our 20s, Johanna and I stared for a long time into our souls and concluded that three things matter to us over everything else: our relationship, being able to honor our curiosity, and giving our children the opportunity to do the same." There's another excerpt. You say, "We have the same responsibility to the people we will be a year from now. Looking for Limitations is about extending care to your future self." There's this theme that has come up in several places around our past and future selves. Then a piece that I hope everyone will go read, I hadn't read until I was preparing for this, called "The Third Chair." It's very, very brief, I read it on the plane here and had chills. **My question is:** How are you being kind and grateful to your past self? How are you being generous to your future self? And to what extent can you, or are you trying to, model that orientation to your daughters? **Henrik:** The first part we've talked about. This training, seeing mistakes as the first step to growth, and rewiring myself by doing it over and over again has changed my relationship to my past self. I feel immense gratitude for all of his mistakes and successes. The interesting consequence is if I feel so much gratitude for what he sacrificed and did for me, then I... My mom usually tells me when she does something to help me, "You don't pay back to me; pay back to your kids." I can't pay back the person I was when I was 20; he's gone. But I can pay back the person I'll be when I'm 70, and so on. It comes to a commitment to always embrace a little discomfort in pushing my limits and staring at my flaws. Yes, that's a short-term pain. Even though I feel less pain around that now than I used to, it's still a certain amount of pain. By putting a few of my hours every week into doing that, I'm giving a gift to my future self. If I am able to overcome this limitation or grow as a person, I know some future version of me will bear the fruit of that. All sorts of things, like exercising and taking care of my relationships. All of these things are nice to me now. But it's also a way of—it can be quite useful to visualize your future self, not as a goal, not as "I'm going there," but as a person I'm going to be and that I should project some love toward. What kinds of things would make his life... It could be small things, like I can do the dishes tonight, and tomorrow Henrik is not going to have a terrible morning. It's small things and big things, just by remembering that person. Often, the sacrifices you make now can be quite small, and the return is amplified by compounding. So you can make a small effort. **Jackson:** They're leveraged. **Henrik:** If you think about explore, exploit: if you go around, and you're single, you might think, "I don't feel like going out and talking to people." But if you go out, talk to people, and find the right person, the payoff for your future self is immense. There's perhaps some social anxiety you have to deal with that night, and the payoff can be unbounded. Tyler Cohen has this line: when you decide what to work on first thing in the morning, you should have a zero discount rate. Meaning, you should work. If you value all the future equally as much as today, what would you do? If you can make the first one or two hours every day to work on things that are not putting out fires or gratifying yourself right now, but are making some progress on the thing that's going to pay off in 100 years, do that. Take a few of the best hours every day to move a little bit there. One of the things I feel very privileged in getting to write full-time now is that I can work from home. This means I'm a much more high-fidelity role model for my kids because my work is very much in this vein. A big part of my work is me reading books, doing my Anki cards, and pushing myself. My kids get to see that, and they get to see the fruit of my labor. That's important to me, just modeling it. We also talk about it a lot with the kids: the importance of removing her bottlenecks and overcoming friction. This is going to be painful. With the seven-year-old, she's starting to get big enough that she understands these things and is starting to have the experience herself. We can start to talk about it. It's really interesting to have a very conscious decision. She and her friends love to ride on stick horses, and they do stick horse competitions where they compete with each other. The first time she was going to do that, she was super nervous and didn't want to be a part of it. We said, "No, this is probably going to be fun if you overcome this, at least." It's a small thing; she's a seven-year-old. But the experience for her was talking through that and then going through all of the exercise. We talked about how the way to move past the fear she's feeling is to prepare herself. We told her, "You're going to be the most prepared person when you come to the competition. Then you can't fail because you've prepared so well." She did that. She said, "I prepared, and I wasn't afraid. Then I could do it really well." It's a small win. **Jackson:** But I set future me up to succeed. **Henrik:** Exactly. Then we can talk about it now that she has a real, lived experience of consciously going through the process of being afraid of something, overcoming it, and then getting a reward: finding this new fun activity and community with her friends. Then we can reference that. "Okay, with this other thing you're afraid of, the same thing will happen if you do that." Keep going, keep going. **Jackson:** Powerful stuff. That's all I got. **Henrik:** Thank you. **Jackson:** Thank you very much.