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One of The World's Most Under-Rated Writers — Henrik Karlsson

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David Perell1:31:53Open on YouTube
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The bottom line

Good writing grows from a deep personal need, material lived with for months, and constant checking against reality. That makes the essay wiser than its author and draws the readers who fit it.

Key takeaways

  • An essay is ready only when long-held material meets a question that matters personally. 2:00
    • The best pieces drew on years of reading and conversation, so Karlsson gives an idea about a year before writing it.
    • The question has real stakes, such as how to become a better father. That gives the essay drive, and the opening is written last, once the true point is clear.
  • Testing every claim against real cases makes the writing truer and smarter than the writer. 13:35
    • Each piece is checked against three or four cases from his life, his friends' lives or biographies. Most of that work never reaches the page.
    • He writes questions in the margin, such as "give me three examples". When an idea breaks, the confusion that follows lets in better data.
  • The order of the material is felt in the body, because an essay should put the reader in a state. 6:28
    • He lies on the sofa and moves clusters around until he feels energy release. Then he types fast to keep that momentum.
    • His ideas form a net, and the essay is one walk across it. He compares this to a spider web.
  • Courage, not technique, is the main limit on how well one writes. 1:06:18
    • His writing deepened after a friend's suicide when he was 15, and again during three lonely weeks in Bolivia.
    • The need to be liked drains energy. He quotes David Foster Wallace: 90% of a writer's effort can go to being liked, which "results in bad fiction".
  • Honest, odd writing pulls in the people who fit the writer and changes him. 1:29:23
    • In December 2021 he had about 50 readers and began getting emails from strangers who had read the same books.
    • Once he stopped simplifying for a mass audience, his writing became too weird for most people. The few who loved it shared it, and that started a flywheel.

And in that way you're sucking reality in and reality is like much smarter than you are. It's got more nuance.

Henrik Karlsson

Chapter summaries

0:00 The 5-Step Writing Method Anyone Can Use

A driving question turns a year of notes into an essay
Excitement comes first, but the essay only takes shape once a question with real stakes starts sorting the material.

An essay moves because a question drives it, and that question then pulls the material into an order that shapes the reader.

  • A question the writer must answer gives an essay its momentum. 3:15
    • In a novel, someone wants something and obstacles block them.
    • In an essay, the writer needs an answer and won't be happy until the loop closes.
    • Without an open question a text is just one thing after another.
    • Forcing excitement works a little, but it is never the same. He takes the pressure off and lets curiosity pile up.
  • The question pulls the gathered material into shape. 4:09
    • Once the energy arrives, the notes from books and journals turn into a landscape.
    • The question acts like a magnetic field. A story or an Aristotle argument gets drawn in.
    • Structure starts to appear as he moves the material around.
    • He asks what each piece can do to answer the question that drives him.
  • Order matters because an essay runs in a line and each unit sets up the next. 5:03
    • He sees an essay as a series of centers. Each is a unity, and together they form a strong wholeness.
    • In Ways of Seeing, a Van Gogh looks different once you learn it was his last painting before he killed himself.
    • He writes about deep, eternal truths that sound boring if stated flat.
    • A story first, then the insight, opens the truth up. A left-field insight can then turn it upside down, like improvisational jazz.

8:30 How to Create Tension That Hooks Readers

A first draft should be written fast and whole, and the opening is the last thing to fall into place.

  • The core is drafted in one fast pass so the essay stays a single wholeness. 9:25
    • Pieces written separately and joined later often fail to cohere.
    • Having lived with the material makes a quick pass easier.
    • He sometimes talks the essay out with his eyes closed and transcribes it, several times, until it snaps into place.
    • Heavy editing comes later. The first pass only follows the gradient of energy.
  • Writing the opening first makes it stiff, so it comes last. 11:11
    • Knowing it is the opening makes him pretentious and tense. Two or three hours of labor later, it doesn't hold.
    • In Looking for Alice, a throwaway line sat mid-essay. Asked if she was a lesbian, Gertrude Stein answered, No, I just like Alice. Moved to the top, it pulled the essay together.
    • Once the essay is on paper, the opening is often already in it.
    • He doesn't know if this holds for everyone, only that it works for him.

12:44 Why Looking Away From the Page Improves Writing

Words fix on the page what the eyes should keep checking, so the writer has to keep looking at the thing itself.

  • Ideas worked out only on the page stay brittle. 13:04
    • On Less Wrong and Reddit he was expected to have big ideas, and they got stuck on the page.
    • His sharp-eyed wife poked holes in them easily.
    • Like a painter with a still life, he writes, looks, compares and rewrites.
    • Fussing over an adjective or a metaphor makes you forget the sentence is meant to represent something.
  • Looking at the real thing beats thinking about it. 15:10
    • He quotes Wittgenstein: don't think, look.
    • Describing a plant again and again shows he never saw it. Is the flower really white? How many leaves?
    • Perell's drawing lesson: a red dress in sunlight is thousands of shades of red.
    • Delacroix's diary records daily visits to the stable. He writes that a shadow is yellow in one place and purple in another.

18:03 How to Suck Reality Into Your Writing

Questioning your own claims and testing them against real data makes a piece hold more than the writer knew.

  • Interviewing yourself pushes past habitual language. 18:28
    • He asks what a phrase like the shadow is yellow actually means.
    • When his examples don't match his claim, he writes about why.
    • While drafting he stops to ask: do I believe this? Can I give an example? A counterexample?
    • He also talks it over with his wife and friends and reads books on it.
  • The text keeps what the writer forgets. 20:09
    • A draft from March, read in June, is read by a different Henrik who has forgotten the original considerations.
    • The text remembers them and gathers feedback from others.
    • His wife doesn't cross out words. She says let's throw that out, but that's interesting and starts a conversation.
    • They check his claims against biographies and his diary.
  • Feeling something deeply while writing carries it to the reader. 21:58
    • When the subject is his own emotions, he enters a dream state, eyes closed, talking into voice transcription.
    • He can't tell whether the feeling is on the page, but it seems to come across.
    • Years of writing have made this easier. Words on a page became forces he can sense.

23:18 Why Writers Feel Compelled to Write

Writing gets messier before it gets simpler
Like his wife's cleaning, a piece has to be pulled apart and get worse before it settles into a view he never abandons.

Writing is how the writer lets reality in, so it changes him, and the feeling in a piece matters more than its advice.

  • Writing lets more of the world change him. 26:13
    • A book he only reads does not enter his body. Putting his own words to it does.
    • Status drove him when he started. What sustains him now is being transformed.
    • After about 30 hours on a piece, he may see he was thinking about it entirely the wrong way. The view snaps around and he never thinks about it the old way again.
    • He compares it to cleaning his head and putting things in order.
  • Confusion is the middle of the path, and the path ends in something simpler. 27:50
    • His wife cleans by pulling everything out first. It gets worse, then everything goes back in clean. He writes the same way.
    • He starts with a simple idea, doubts an assumption, adds an example that does not fit, and gets lost. Then it compresses into a new, simpler formulation.
    • He used to think a messy middle meant failure. A mentor told him he was halfway there and should ride through the confusion.
    • His piece "Looking for Alice" was meant as advice to a friend and leaked. Rereading it years later, he found half the advice shaky. It works because readers can feel how much he loves his wife.

29:23 How Lowering Your Promises Creates Better Essays

Small opening promises let essays roam and overdeliver
Bold promiseSmall puzzled promise
ExampleShared childhood patterns from 40 booksWhy favourite books weren't meant for publishing
Writing feelsLabor, a job to finishExploring, playful
MidwayNot delivered yet, must force onWanders into education, cognition
ResultStrained pieceOverdelivers
He still writes the big canonical pieces, but the modest ones carry more playfulness and energy.

A small, puzzled opening promise gives an essay room to roam and to overdeliver.

  • A bold promise turns writing into labor. 29:45
    • His piece on the childhoods of exceptional people promised the shared patterns from 40 books.
    • Three parts in, he would see he had not yet delivered and had to force himself on. The piece feels strained.
    • He still likes such pieces and says the labor is sometimes worth it.
    • The "big piece" feels like slay work, a job to finish rather than a place to explore.
  • A silly observation lets him explore freely. 30:51
    • One piece began only with almost all my favorite books were not meant to be published. He promised just to think about why.
    • It wandered into problems with education and into cognition. Since none of that was promised, it felt like overdelivering.
    • Playfulness and energy make these pieces much more fun to write.
    • He guards against the audience by staying offline at least half of each day. He often writes on paper or dictates while walking up and down the road.
  • Even the wish to be understood can block fragile thoughts. 34:00
    • The most interesting ideas sit at the edge of language. Forcing them to be clear can drop them.
    • He edits by feel, like playing chords. Flowing water gives way to a short snap, and an intellectual passage gets a different color beside it.

35:40 How Deep Conversations Generate Great Ideas

Good ideas come from slow feeling, rich conversation and clashing fields, and they need a life built to allow them.

  • Feeling takes time, so slow down. 35:42
    • He sits silent with eyes closed for 5 to 10 minutes. Or he walks until a word is ready to come out.
    • If he has been with a piece for a long time, he lets it simmer in the subconscious for a day or two.
  • Interesting friends and odd reading collide into ideas. 36:54
    • After he posts a rough idea, five to seven emails arrive. They bring book tips and Zoom calls, and he often surprises himself.
    • As a literary person, he pulls ideas from machine learning and mathematics and crashes them into poetry.
    • He gives the head space with four-hour walks, journaling and reading until an idea surfaces.
    • He builds his life around such experiences, for example by keeping the internet off.
  • Depth needs saying no to most things. 39:03
    • After 12 years with his wife, they are about 10,000 hours into their conversation, and it keeps getting better.
    • Around 25 he set music and programming aside to focus on family and writing.
    • Letting go takes courage because you look odd, and it is easy to sacrifice the wrong thing. Writing about it helps him rank what he values.
    • He chose writing over a car at first. Now he has both.

42:02 Why Breaking Grammar Rules Improves Your Voice

Real writing confronts a fear, and bending English grammar could give the language back some freedom.

  • His best pieces feel like a descent into a cave. 42:04
    • The writing asks him to become a better person. He has to face something scary that holds him back from being present with his wife.
    • Sometimes the need is a puzzle of how things fit. Sometimes he already knows the answer but must sit with it to let go of the fear.
  • Swedish word order is looser than English. 44:57
    • Danish and Swedish are about 70% alike, and English about 20%. English grammar is stricter, so every word has a fixed place.
    • In Swedish he moved words around like weights on a scale to set the rhythm. In English, any move reads as ungrammatical.
  • English should take in wilder forms. 45:48
    • LLMs push toward standardization. If English becomes the global language, it should borrow Turkish grammar and Persian words.
    • Borrowing from Swedish makes him look wrong, so he hesitates.
  • LLMs help him with small jobs, not with his prose. 46:36
    • About 1% of his words come from them, mostly a missing word or ten rephrasings to get him out of his head.
    • He has seen interesting images and music from LLMs but no good literature yet.
    • He stores his bad habits and overused words in a prompt and has it check each essay.

48:49 How to Write as Discovery

Writing that explores a question beats writing that hands down an answer, because readers want to watch someone think.

  • Leaving dead ends in the text makes it sincere and intimate. 50:10
    • Writers who say "wait, I'm wrong here" let the reader trace the steps of the discovery.
    • Not every false start stays. The aim is to simulate the process of finding out.
    • Perell notes that heavy editing often removes exactly this honest searching.
    • Karlsson forgives odd flaws in writers he loves, yet judges his own much smaller ones.
  • Fear of looking stupid pushes writers to rush to the point. 51:06
    • Writing exploratively takes a relaxed, letting-go state that Karlsson says feels like a different part of the body.
    • Readers rarely think a writer is dumb for lacking polish.
    • Perell finds lack of polish endearing in others, yet tries to look "all buttoned up" at the keyboard.
    • A ridiculous take is judged on the take itself, not on the writer.

52:34 Why You Should Protect Your Early Ideas

Writing walks one path through a web of ideas
Karlsson drafts around 50 linked notes in Obsidian without knowing where they start or end, then chooses the thread that touches the most important points.

Young ideas are fragile and need shelter from critique and social expectations until they have grown into something.

  • Early critique squashes an idea before it can grow. 52:36
    • Jony Ive said at Steve Jobs' funeral that young ideas are fragile, like a little bird.
    • Some of Karlsson's best ideas start as almost nothing, such as a feeling that is "pink". Said aloud, it sounds silly.
    • He keeps such ideas in his diary or in his head on long walks until they grow.
    • David Lynch catches image fragments, puts them on a hook and lowers them into his subconscious as bait for bigger pieces.
  • Writing turns a net of associations into a line. 55:16
    • Memories and feelings arrive all at once, but prose runs one word after another. Good writing then expands back into a net in the reader.
    • Karlsson writes about 50 linked notes in Obsidian, without knowing the start or end, then picks a path through them.
    • Werner Herzog wants "ecstatic truth", not an accountant's account. He invented a fake Pascal quote to raise the mood.
    • In Herzog's film about a Vietnam prisoner, the opening and closing of a door was staged. Karlsson does not invent, but sets an emotional color before the idea lands.

1:01:31 The Strange Writing Experiments That Actually Work

Trying odd methods on yourself shows how your own mind writes best.

  • Changing the conditions of writing reveals what helps. 1:01:31
    • Karlsson tests handwriting, walking while writing, different music, and very early or very late hours.
    • He once lay still for half an hour without a single word in his head, to feel an essay's emotional currents. He got the idea from the mathematician Hadamard, who found great mathematicians think in bodily intuitions.
    • His essay about misreading the people you know began with no plan. He lay on the sofa and talked aloud about his best friend, like a therapy session.
    • He spoke far more than the essay holds. Then one stretch felt like it had a border around it: that part was "a thing".
    • Perell wants to try talking through a piece in noise-cancelling headphones so he cannot hear himself.

1:06:11 How Courage Becomes Your Writing Bottleneck

Craft questions are often excuses, and the real work is staying close to lived experience and being bold with it.

  • Writers blame technique to avoid the scary work of boldness. 1:06:18
    • Karlsson tells himself he needs better metaphors or openings, but going deeper is usually the answer.
    • Grammar and adverbs are easy once a writer has a perspective and is grounded in themselves.
    • He likes Herzog's joke that film students should walk from Madrid to Kiev. Some ordeal strips away everyday social expectations.
    • In Bolivia he had no one to talk to, and every role he played at home fell away. A homemade notebook filled up, and he came back unable to return to how he had been.
  • The best writers are both porous and firm. 1:09:43
    • Loving curiosity means trusting the world and asking what is going on, not trying to prove you are smart.
    • Being porous lets reality move you. Firm values keep the world from dictating who you are.
    • He sees both traits in Jesus, who was loving yet firm about what he stood for.
    • Perell adds that beauty lies in pairings, like a chord progression or an orange slice after dark chocolate in a hot desert.

1:13:50 Why Boring Truths Make Powerful Writing

The deepest truths are obvious, so they have to be built into an experience before they land.

  • Truths about how to live can't just be stated, so the writer builds an experience. 1:14:26
    • Sequencing does what ritual does: it puts the reader in a deep state.
    • The New Testament mixes parable, poetry, images and plain statement to carry a very complex set of ideas.
    • Physics can be written down. Ethics has to be constructed.
    • Karlsson's farm passages in intellectual pieces work like the orange slice in a ritual.
    • Poet David Whyte defines poetry as language for which we have no defenses. The same thing happens in music.
  • The most alive ideas are obvious ones, and the writer must make them real. 1:17:16
    • A post that says "be kind" would fail. Writers avoid such truths because they sound boring, and say something smart instead.
    • The boring truth has to be pierced through to the heart with a piercing, poetic construction.
    • If the writer feels no surprise or excitement, the reader won't either.
    • Paul Millard wrote his memoir by walking until he cried. Perell wrote much of The Pathless Path in tears.
    • The writer is the one person they can watch closely, so their own reaction is the test. Tricks can make people cry, but that is fake.

1:19:54 How to Write From Your Subconscious

Staying uncompressed and unsure keeps the writer learning from reality instead of from their own models.

  • Writing on paper stops ideas from floating, so they can break. 1:20:06
    • In talk, a challenged idea can shift to "that's not what I meant". That saves face but doesn't improve thinking.
    • Mental models filter what we notice. Someone who thinks the left is stupid remembers only its stupid remarks.
    • Past the models, he sees in higher resolution.
  • Observing without words gives high resolution, and compression comes later. 1:21:55
    • Perell compares it to a giant photo that hasn't been compressed.
    • Labels like "the political right, tariffs" compress too much.
    • Compression happens only after a year or two of looking.
  • Deliberate confusion speeds up learning. 1:23:43
    • US military accelerated-expertise programs give trainees cases with no theory, then a case that breaks their first explanation.
    • This prevents a "knowledge shield", where a model that is good enough makes us ignore everything else.
    • Confused means a few half-working models and no stable one. It does not mean disoriented.
  • Writing, family and farm work feed each other. 1:25:38
    • With mold in the main house, the family lives above the stable. He writes in the old woodworking room.
    • When stuck, he lies on the sofa, walks the meadow or fixes a brick wall.
    • He works from 7 to 3, six days a week, then spends four or five hours with his kids.

1:27:46 How Writing Summons A Culture

A blog post is a search query for your people
Dropping the magazine habit of cutting out the weird stuff is what let the right strangers find him.

A blog post works as a search query that draws in the people who fit the writer.

  • A long title is useful, because most people read only the title. 1:28:19
    • His post title calls a blog post a very long and complex search query to find fascinating people.
    • The idea that writing is a search query blew my life wide open.
    • Posts move across the social graph to people interested in the same things.
  • Writing summons the culture that can hold the writer. 1:29:29
    • Meeting those readers changes him, so the writing makes him a different person.
    • Many people never felt at home in their hometown or job. Here the full idiosyncratic self is encouraged.
    • He wishes everyone a few posts out there so their people can find them. Being seen in your interests and values is deeply nourishing.

In the growth library

Henrik Karlsson, essayist and writer of the Substack blog Escaping Flatland. Henrik Karlsson explains how he writes essays that feel alive: he lets an idea ripen for a year, tests it against reality, and writes only once a real personal question drives him. The technique worth hearing is his five-step process, which ends with writing the opening last and drafting fast once the order of ideas feels right in his body.

Lessons that draw on this:

More from How I Write · The whole library, and ask it anything

Transcript2465 lines
The 5-Step Writing Method Anyone Can Use 0:00
0:00

Well, Henrik, you have a blog that's called Escaping Flatland, and you've written so many pieces over the years. Some of them gone mega viral to Substack. And by writing those pieces, you've developed this five-step method for writing that I think would be a really good way to start. It's basically a five-step method. Anyone can use it. And the very first one, like it just begins with exploring. But for you, exploring is something that happens over a long time. So, let's start there. and we'll go through the five-step method.

0:30

>> So, a mistake I've often done and which never ends well for me is that I'll get really excited about an idea and then I just sit down and start typing almost right away >> because that there's something that is like unmurred. It's not grounded in me yet. So, so what I found like as I was going over and like I was looking at all of the pieces I've written and like some of them I don't like and some of them are like I can't believe I wrote those pieces and like what did they the really good ones have in common and the what the really good ones had in common was that I was writing from like a deep source of knowledge and experience that were these were things that I had read about often for years that I had many conversations about. I had maybe worked on these topics like I they were alive in me in a very deep sense and and sometimes that was just accidentally I had lived but sometimes it was just I

1:23

want to understand this uh and I get excited about something but when I get excited about something I can't write about it I have to like give it a year so I'll read books >> a year. >> Yeah. Yeah. Yeah. I mean, at least like it it takes time to make something your own and to like move past like the the simplistic way of thinking about things. >> So, I'll make some notes. I'll go back a few months later and I'll question myself and I'll change how I word things. I'll see it in a different way and then I'll read a book. I'll go back again. and I'll have a conversation like over and over like until I have sort of accumulated something that becomes like urgent like at some point something coaleses into something that is driving me and often I think of that as a sort of animating question like the stakes rise and I feel like this is really important and I need to get this on paper and it's like a a question that I

2:16

need answered because it matters to me as a person. It's like maybe how could I this will help me become a better father or husband or whatever something that's really alive and important to me when I get that energy in my body then I know it's like I'm ready and the material is ready to kind of move into to writing something >> and does that process happen on its own pretty organically like one day one moment you're just like whoa there's the animating question I now I now need to write about this that's because it's the animated question and it's the stakes it's both of those paired I sometimes like because I write like professionally now I feel like I should put out pieces and I sometimes try to like force myself to have an idea force myself to get excited about something I can do that sort of but it is never the same thing so the best thing is just like take the pressure off just follow

3:06

my curiosity let it accumulate and just trust the process that it's going to arise something that just wants to be born for me >> and why is the animating question important why can't I just write about a topic >> yeah Well, a topic is a good piece of writing needs to have drive. It has to have >> drive. >> Yeah. But or like a narrative tension. It can be done in different ways. So like in a novel, it's usually done someone wants something and is trying to get it and there's obstacles, right?

3:33

That prevates provides momentum. You can do that in essays too, but usually in essays the momentum is this is a question and I really really need to know the answer of this question and until I've closed that loop, I won't be happy. That's what kind of moves you through a text. And unless you're opening those kinds of questions, there's no movement in a text. It's just one thing after another. >> So, tell me about step two. When when do you move from that to then collecting thoughts? Cuz it feels like what's going on there is you're collecting thoughts, but no, no, no. Something different is now happening in the second phase.

4:09

Once like uh that energy comes into it like then I I get like a vantage point and I have sort of accumulated all these notes from books I've read and journal notes but now like I'm seeing the landscape I'm seeing where I need to go and then I'll start kind of pull that in into a shape. It's almost like a magnetic field. The question is a magnetic field that is pulling the material in and starting to shape it and I should move have these things I need to these are things I need to answer this question that is driving me and and and kind of a structural start to sort of arise as I move the material around and like how could I this story could help me kind of go in and understand this more deeply and that argument from Aristotle could be used you know like I'm starting to see and then maybe well if these things belong together and then like I usually think of like the third step is once there's like these clusters

4:59

start forming because on an essay I like to think of essays as these almost geometrical things. It's it's like a series of centers. It's a series of of um units that are they have to form like a strong wholeness but there are made up of different centers. Uh so you're starting to feel like these things belong together. They are a unity and these things are unity and these things are unity. But when I put these three or four things next to each other, they kind of something happens between them.

5:31

So I'm starting to see like these are the units and if I put them in this order, like something comes alive between them. An essay happens linearly. So then you're ordering the ideas, which is step three. And how does how does that process work? That kind of feels like when you go from the exploratory phase to the ideas kind of snap together and then you actually begin a process of composing a piece. Is that right? >> Yeah. Yeah. It's it's and that's a sort of tricky part because like in my head as I'm seeing these ideas and these images, it all sort of happens at the same time. It's kind of a like a a net of different images and and they're all interconnected. But I need to figure out like which order to put these things so that I produce the the right kind of um state in the reader because like an on an essay is I I think of that as sort of a >> it's about it's not about committ communicating just ideas. It's about

6:30

like putting the reader in a certain emotional and cognitive state. And you have to sort of figure out like how do I sequence these images and clusters that I've amassed in such a way that like maybe I'll need to have this image this if I put this story here that's going to put the reader in a certain emotional state. So then when I go in to talk about Aristotle they're going to be emotionally ready to deal with that.

6:53

>> In uh in ways of seeing it goes something like this. There's this Van Go painting. Okay, you look at the Van Go painting and you say, "Okay, what do you think?" And you have a series of thoughts. Okay. And then you flip the page and it says, "That was the last painting that Van Go painted before he killed himself." >> Yeah. >> And then you look at the same painting again and now you see that painting completely differently because of the sequence of the thoughts.

7:24

>> Yeah. Yeah. It's that yeah that's a very wonderful passage and it's like beautifully sequenced and yeah so sequencing really matters especially for the types of topics that interest me because I'm always trying to write from like things that are like deeply human like I typically don't write about like esoteric stuff just to find something clever and new. I want to write about like deep eternal truths in a sense and they can be sometimes almost boring if I just say them right out. But I if I can sequence it in the right way and tell like a story and then I tell say that important insight after the story that that could so open something up and then I might add another insight that's coming from totally left field and turning everything upside down. But it's almost this kind of improvisational jazz kind of thing where you're trying to sort of assess. It's an emotional experience when I'm doing it. I am I'm

8:19

kind of sometimes I'm even lying down in the sofa and I kind of picture these clusters in my head like I I'm having this cluster has this kind of color and this kind of feeling and and if I put it

How to Create Tension That Hooks Readers 8:30
8:31

next to that one. No, there's no energy there. But if I put it I change the order. Wow. Like now like I felt this energy released in my body. That's the right order. Now they snapped into place. And then I but I have this third idea that I want to get in. And can I put there? No. There. I'm like moving them around in my head and and I can almost because I've written so much I can sort of visualize them almost as geometrical objects geometrical objects in my head and kind of feel the energy fields between them. It's that sounds almost woo but but that's how it feels.

9:03

So basically we have step one which is exploring and sort of waiting for the animating question. You begin to find that then you really start kind of deliberately collecting thoughts. Then you're looking as you're collecting thoughts you're looking for clusters. Then you begin to order the ideas and then you begin to write the core. That's step four. >> Yeah. Exactly. And and then you write through it. Sometimes if I'm really lucky that I can just start writing and the sequencing happens by itself. But but often I need to like sit for a long time and just feel in my body how the sequencing should be. And then once it snaps in place I can just feel this release of energy in my body.

9:43

>> Then then I'm like okay let's hit the keys here. Like let's let's type this out. And then I usually type really fast. I try to go because now there's like this uh there's stakes, there's like emotion going into it and I want to capture that energy because I know if I feel it in my body there there's going to be momentum in the text. If I'm excited, I'm just move through it and and if if I can get myself to laugh and cry like that, that's going to happen for the reader, too. So, so at this point I'm just trying to get through it and I'm going to have to edit a lot later, but I want to get that first like uh follow that kind of gradient of energy at first and get it to be like a coherent whole thing. Uh and not just because I don't want to have it be a patchwork, right? Because sometimes you'll write a little piece here, a little piece there, a little piece there, and then you put it together and

10:32

it doesn't really cohhere. A good piece is is a wholeness. It's not separate pieces next to each other. So, I I find it's easier for me to get into that if I've lived them with the material and then I just like let's go through it kind of fast. Sometimes I I even like uh transcribe it. I'll lie on the sofa, close my eyes and I just talk it out and just sometimes I'll do it several times. I'll talk my way through the essay and then I'll do it again and then I'll again until it kind of snaps in place.

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Uh and then I'll have a piece and then kind of I guess after that it's the editing. So that's step five, editing. >> Yeah. Yeah. And an important thing that I almost always do is that I write the beginning and the ending when everything is already done. And I know I don't know if that's generally true for everyone, but for me, if I start writing a an opening and I know this is going to be an opening, I get really pretentious. I get really tense.

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It's overworked. It's it takes a lot of work. I'll sit for two, three hours working on that opening and then finally I get through it and I can start writing through the piece and then I reread it and that >> it doesn't hold. >> It doesn't hold. So it's not worth it for me to do all that labor to get that opening. So usually because usually once I've written a piece like the opening is obvious. So I wrote when I wrote looking for Alice for example, I I wrote it that way and and then in the middle of the piece there was just a throw throwaway line where I said that u someone once asked Gertrude Stein if she was a lesbian and uh Stein answered no I just like Alice and I was like wait if I move that to the first line that's just going to make the whole essay kind of come together. So it just it just arrived in the writing. I didn't have to think of it because like once the essay was there and I and I could

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see clearly when I was on paper what it was about then it was obvious what the opening should be and I already had it so I just had to move it up there. Often it's like that I can just take something and move it to the top when once I've understood what the like the true insight of the piece is. So tell me

Why Looking Away From the Page Improves Writing 12:44
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this. So I want to talk about that. Okay. How do you actually write? Well, and the thing that you have picked up on that has been a shock to how I think about the craft is to spend less time looking at the page and more time looking at the thing that you're describing. >> Mhm. So I as I said I started wring on like less wrong and Reddit and there's like this intellectual thing where you're supposed to like have big ideas and and I had to sort of unlearn that because I realized um I was sort of getting stuck in the ideas was getting stuck on the page and and there was like no and the ideas were kind of brittle brittle in a way and then I realized yeah brittle they they would kind of I mean I have a wife who's very sort of sharp eyed so she would look at them and she'd very easily poke hole on them right >> and um and then What I sort of realized that I need to look at real things. I would I started writing from sort of

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case studies like not necessarily that the case studies are in the writing but every piece I have I've sort of had like three or four like case studies like examples from my life from my friend's life where I'm like testing what I'm writing against. Uh sort of like a painter doing a a still life or something. I'm I'm putting something and then I'm painting and then I can look at it like is what I'm saying does that match reality here? And I'm trying to uh and there's something about that process where cuz you're I I want to suck reality into the writing.

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>> Uh so so so when I I write something and then I look and it's like no reality actually looks a little bit different cuz what I'm saying here doesn't match. So and I go back and I rewrite and then I look again like like a painter, right? So they you look, you paint and you compare. Oh no, it's not actually like that. and you look again and and in that way you're sucking reality in and reality is like much smarter than you are. It's got more nuance. Uh and and and so so you you don't even have to have it in your head. You can just like suck it from reality.

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>> And what's the thing that most people get wrong or that you didn't understand? You might start from something like you you have a conversation, you're talking about a problem and then you write it on the page and now it's on the page and you're like I really don't like how that sentence sounds or maybe I should have a metaphor here and oh maybe this adjective oh maybe not and you start like moving the words around and you like forget that this is actually trying to uh represent something and and so so I want to I'm saying like spend more time looking at the thing right like Vitzkinstein has this line which says like uh don't think look. Uh so so it's just you don't want to get caught up in your mental models and your representations. You want to like always turn to the real thing and uh and look at it. I I actually do like these still life kind of exercises where I'll go and actually like look at a this up there's

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a plant over here. I could like stand and look at that for a long time just describing what I'm seeing and then like correcting it again and again. It's just an exercise. It gives a certain certain humility because I realize like, oh, it's a white flower, you know, like, oh, is it is it really white? No, it's actually something else going on in the middle and like how many leaves are there really? And like once you start going back and forth, you realize you I didn't really see that flower at all.

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And and it can be a quite interesting experience to just like take even a flower and just write about it and look and write. Look and write. >> Yeah. I never learned how to draw, but all the time that I spent drawing and trying to paint things, the number one realization I had is I've never actually looked at anything in my life. Like literally, I'd never actually looked at anything. Because when you draw, you just realize the most subtle details.

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Like for example, if if if like a woman is wearing like a like a red dress, just walking in the sun, that dress is actually like 10,000 shades of red. And then there's all the wrinkles on the dress and the curves of the entire thing. It's not is so much more than just a red dress. But the abstraction that we get in our head is, "Oh, it's a red dress." And I think that what ends up happening is as you look and look and look, you're reaching past your current understanding of a thing and trying to dig deeper into something that's truer and higher fidelity.

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>> Yeah. Yeah. It's it's it's such an interesting experience. I was reading um the diary of De La Cro, the French painter like yesterday and and it's so interesting to like he's always I mean going around both in writing and in painting looking at things. So it's it's just every day like today I went to the stable and looked at the horses and then like today I get went to the stable again and looked at the horses and he's just going around like that's his job.

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He's going around looking year after year looking and it's so interesting to see how he writes about it because he'll notice things about horses and leaves that I would never notice and and and the way it's almost surreal to read his description sometimes and he'll say like uh the shadow was yellow, right? like he'll say this it sounds almost bizarre like the shadow is yellow but he's actually seeing the actual color of it whereas I would just think the shadow is black or something because I haven't looked but he sees that the shadow is yellow in one part and purple in another he's like actually seeing and he's just going around all the time writing and painting and it's it's incredible to see someone take that practice really

How to Suck Reality Into Your Writing 18:03
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seriously and so tell me about your process of you have an idea something that you feel moved by compelled to write about and then you have this surface level understanding of what the thing is. You've you've glanced at it. How does the process of making your written description of it, how do you make that vivid and concrete? >> Yeah, it's it's a long process for me. I I usually I'll I'll think about something, I'll make some notes about it, then maybe a few weeks later I go back and look at those and question myself. I'll often kind of interview myself like what do you mean the the shadow is yellow or like whatever like what what does that mean I'm interviewing myself >> tell me about that >> um it's it's it's it's this way of pushing past this sort of habitual language I'll just kind of say things and then I'll I'll I'll sort of interrogate myself like what actually mean like that question like what do you

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mean what does that mean do you have an example like I I'll literally like write these questions to myself in my notebook I'll in the margin like give me three examples like I'm interviewing myself and once I start maybe okay so three examples I'll start thinking about that and then I realize oh wait like those examples doesn't actually match what I said there what's going on there and and then I'll write about that like why is that doesn't it match and you know it's so this this process of actually trying to understand it and I'll talk to my wife about it I'll talk to my friends I'll read books about it I kind of try to feel my way around until I feel like now I have it fairly well and I'll start writing and then there is a this process again like I'm writing it and I'm stopping and rereading what I've written. It's like is that do I really believe that? Is that really true? Or like can I give a concrete example of

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that? Can I think of a counter example of that? Like interrogating again but hopefully at this stage I I'm fairly solid. But also, you know, show it to my wife. She'll do the same. It's this process of I'm try again. I'm trying to suck intelligence into the piece. I want the piece to end up smarter than I am, you know, because >> by doing this, that's the beautiful thing about writing, right? Because you have this artifact. So, I'll sit like, let's say in March, I'll write something down and then in June I'll go back to it and now I'm actually like it's to Henrik have written on that piece and it's and and >> cuz you're a different person now.

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>> Yeah, I'm a different person and I don't even remember all of the considerations that went into the first draft. that's kind of forgotten, but the text remembers them and the text starts to sort of accumulate more than I have and it starts accumulating feedback from other people. So, the text end up like carrying more wisdom than I have over time. >> Can you make concrete for me the idea of like sucking in the wisdom of reality?

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Like how does that sucking process happen? >> Um, so when I work with my wife as the editor, so she's like not a normal editor who goes around like crossing out a word or something. She'll she'll read a piece and then she'll say like, "Let's throw that out, but that's interesting. Let's have a conversation about that." And then we'll start, okay, so what's a concrete example of this? Or maybe we'll go like get some biographies and we'll try to kind of match what I said against the biography and look at like, does it fit here? Does it not fit? and and like interviewing and and and so testing it against like real data from the real world like either things I'm looking at from my life, things in my diary, data, biographies, like different kind of I'm trying to find some kind of data source from reality that I can can test my ideas against and and then often like some some of that ends up in the essay.

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Like I'll oh that's a good example. I'm going to use it in essay, but a lot of it is not even in the essay. It's like this iceberg underneath that the reader doesn't even see, >> right? How do you feel like your writing is different when you're trying to describe an emotion or a sensation like a looking for Alice piece versus something more practical and concrete. >> Yeah, it's it's very strange when the reality you're using as your own emotions or your own subconscious or something. But >> yeah, >> um that's harder to talk about. But it's just it's almost entering this kind of dream state. Sometimes I'll lie on the like I have a sofa in my writing studio and I'll just lie down like close my eyes and just put on like voice transcription and I'll just talk and I'm feeling the energy in my body and I'm kind of >> moving around. Um, and I think that gets easier with time as well cuz like now I

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used to writing used to be um words on a page for me and and now I've done it so much that it's kind of become internalized. I can I can sort of visualize a piece as like these force fields of energy almost like I can feel if I that that uh metaphor has a very interesting energy and when I put next to oh that's a good like I feel the energy of pieces and I'm kind of moving around and feeling where I get excited and and then I can uh either talk it out or type it down but like if I'm feeling the fe what seems to happen like if I feel the feeling really deeply and and and and write it rapidly when I'm in the feeling somehow seems to come across to the reader. Um, like it's hard for me to tell is it there, but it seems to work.

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>> I mean, I totally know what you mean and and and I think you you're capturing

Why Writers Feel Compelled to Write 23:18
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something deeply. So, I'll explain what I've learned through podcasts. I used to think of what one of these podcasts was is I would sit down and I'd say, "Dear guest, I want you to give me the most concrete and vivid teaching description of exactly how I write." And it was almost as if I was optimizing for the transcript and the takeaways. Like what are the six things that a listener could learn? And then over time I started thinking, okay, what is a conversation like this? A lot of it is a exchange of energy like our energy gets shared with who's ever listening or watching or tuning in, right? And I think it's the same thing that's true in in in writing.

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So many of my favorite writers, it's not like there's like this logic logical perfection that they're giving me. Wow. The the framework is perfectly packaged. It's actually just I feel like I step into some sort of energy field that they have, whatever it is, and I really enjoy being in it. Maybe it inspires awe and wonder. Maybe I just feel like there's a kindness about them that I find very sweet and endearing, whatever it is. And that's a bit of what I'm hearing you say is to trust that deeper level of language that we can feel but is harder to pin down into language.

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>> And there's almost at least like in the where I move um sort of in the intellectual part of the internet there sometimes even some shame around that like it's soft in some way like at least for me felt like almost hard. I remember like I wrote a piece called Looking for Alice about how I met my wife and I didn't even intend to publish that. I published it because it leaked because it felt like I I can write like emotional soft stuff like that. Is that not how you're supposed to do it? Maybe that's just me, but but it was like like almost embarrassing to go down so deep into an emotion and and it's interesting with that piece too uh what you're saying because I remember at the time because it was my first like big hit that I wrote and I thought like oh it's because it's has such good advice in it and and and and now it's been like two and a half years and I reread it and I was like at least half of this advice is

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kind of shady and maybe not good. Like half of it I think is pretty good, but half of it is ah, you know, maybe not so good. Uh, but what makes this piece work is actually instead that you can feel how much I love my wife. >> And it's it's and and maybe a lot of people haven't seen like an man express very deeply love for his wife. And that was and that's really beautiful. But I didn't even know that was what I was doing. I was trying to give some advice to a friend and that was what I I wrote a piece as advice to a friend. He leaked it and and I put like, "Oh, it's such good advice. That's why people like it."

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No, it's because I kind of let the emotion through. So So that was uh sometimes you don't even know why your writing works. >> Why do you feel compelled to write? >> The thing I like to tell myself is that it makes me feel more alive. >> Makes you feel more alive. >> Yeah. Yeah. But it's it's bringing the world into me. Like I I guess I Yeah, it's it's again like not paying attention. I'm reading a book and it's it's interesting, but unless I stop and like actually write about it and put my own words to it, I'm not going to make it into my body and become part of my uh uh I'm not going to be transformed by it. And I want to like I don't want to I want to be changed by life. I want to to to like grow and change all the time and become let I want to be affected by life and and somehow by writing I I can sort of lower the barrier and let more of reality in and be more changed by it. I think that's the the main drive for me

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now. Obviously like when I was younger started I was I wanted the status and all of these things. So there's a complex set of reasons, but but the thing that sustains me is is this how transformative it is to to really give yourself time to sit with something and turn it over and turn it over and put your own words to it and even like and you write about something and like after 30 hours I'll realize this is the entirely wrong way of thinking about it and then it will just snap around and and I'll change my opinion and I'll like do something completely different and then from that on my life is changed like I'm never going to think about that in the same way. So it's it's almost like I'm cleaning my head and putting things in order and and it tell me about that sensation cleaning putting things in order.

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>> So my wife um has a way of cleaning which I don't really understand is she'll just start by kind of oh this needs to be moved to the garage and this needs to removed and she'll bring everything out and it just gets worse and worse. just moving out the sofa and I only need to vacuum under here and it just I I I get like I don't know how anyone could clean that way but it just gets worse and worse and then suddenly everything moves back and now everything is clean. So that's the way she she cleans and that's the way I write to. uh I'll start with like a simple idea and then I'm like wait I don't know if that assumption is true and now I'm a little confused and maybe I should bring in another example and why that example doesn't fit at all and I get more and more confused and more and more confused and it's just really weird and then we'll talk about it and this doesn't make sense. I I I thought I knew how

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this worked and I don't understand it at all anymore. And then wait a minute, it's actually and then it snaps and then it's like a it compresses down into another simple formulation which is different but it's I have to go through the confusion to get to the simpler thing. >> Yeah. >> Uh and I used to struggle with that because I used to feel like this is just getting worse, man. Like this is this is not going the way it should. Uh but then I I remember talking to uh a mentor about it and he's like, "No, no, you're halfway there. You're supposed to like ride through the confusion." Like you'll start with something simple, you get more and more confused and just trust it. Like eventually it will like collapse down into simplicity again, but you have to ride through it. How do you

How Lowering Your Promises Creates Better Essays 29:23
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think about introductions? And specifically, there's a kind of bar lowering that you've embraced in terms of making lesser and lesser promises at the beginning of the piece, which then give you a kind of permission to almost explore more freely as you write the piece. >> Yeah. So, I I like both kinds of pieces. I like the big sort of canonical piece where you have like a bold promise and like this is I like I have a piece called childhoods of exceptional people and where where I make a really bold promise as I say I'm I've read 40 books about the childhoods of various people have gone on to do exceptional work and I'm going to like catalog like the main patterns they all share like that's a really bold big promise I like a piece like that but they're also incredibly painful to write because the problem when it's you make a really bold big promise like that is that you have to deliver on it and then it just became

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becomes this like almost slay work because I'll start writing a piece like that and I've written now I've written three parts and I look at it and I think I've not actually done what I promised to do this is not still and so I need to do another one is it no it's not done yet either like I have to like force myself to deliver on the promise and there can be a sort of strained feeling to a piece like that it's It's like uh you're doing the labor and sometimes it's worth it. But I really really like another kind of piece where I kind of start with like an almost silly observation like I had a recent piece which just starts with observation uh almost all my favorite books were not meant to be published like it's an interesting observation like what like why would why is that I don't know myself like why is that the case but but it's not like a big promise you're not like oh now this is the big

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piece about why Hendrickk does not >> you're just puzzled by this question. Yeah, the only thing I promise I'm going to think a little bit about why I like unpublished books. That that's everything I promised. But then I can start like going, okay, where do I want to go? This is interesting. Oh, wait, that's even more interesting. And then I can uh sort of move for the landscape more freely and there's like a playfulness and energy to that and and often I end up going to some really interesting places. So in that piece I kind of go into some problems with education and it goes into cognition and it goes into all these different areas and and quite big topics quite interesting observations but I didn't promise it. So when you get to those that feels like overd delivering so there's um and they're yeah they're much more fun to write the thing that comes to mind is that people's actual thoughts

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are more detailed more alive more true than often what they'll say out loud. And I dug up this David Foster Wallace quote where he says, "At some point you find that 90% of the stuff you're writing is motivated and informed by an overwhelming need to be liked and this results in bad fiction." And now not everyone is at 90%, but at some at some level there's this feeling of I'm writing in order to convey something other than just the pure and honest truth. Mhm.

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>> So, so that's one I mean why why it can be so refreshing to read unpublished works, things that people didn't know others would read, right? >> Like when I write, I try to be honest. I try to just like write the simple truth. >> But there's a difference of I'm trying, right? But when I'm writing in my journal, I'm not even trying, right? It's just easy. And even if you succeed, you kind of have to sort of pu push through those incentives that are pushing you to be likable and pushing you like there there are all these forces and that kind of >> saps some energy from the from the writing cuz like I when I'm writing like I I'll notice, wait a minute, I just wrote that because it's cute. Like I wrote that because I know people think I'm cute and likable and then I have to stop and scratch that out and go on. But they are just lost some momentum, some energy. Even if you want to write truly,

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it's hard to do it when you know it will be seen. Uh so so I try to find various ways of of like shielding myself from that influence. Like I spend most of my at least half of my days with no internet connection on. I do a lot of my writing while kind of walking up and down the road like I'm writing on paper or dictating. I'm trying to put myself in situations where I don't remember that anyone would read it. like so I have to do all these hacks to like uh silence that things I don't have to fight against it. Uh but still I I kind of do not always succeed because it's like it's so deep in us that like need to be liked like even the need to be comprehensible like that can even be a problem some like sometimes >> by feeling like I need people to understand what I'm saying here because sometimes the really interesting things you don't really even know how to express. It's like right at the edge of language and

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and if you want to be understandable, you you you'll kind of drop that and you want I want to be able to stay with the really fragile thoughts, too. >> Yeah. >> How do you think about the rhythm of your writing now and editing? >> Yeah, it's so important. Um >> I I really don't like it when I've had a I've written a piece and then I have to take some pieces out and move things and then oh, the rhythm is off, you know?

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>> Yes. and and awful feeling. >> Yeah. And then I and then I just have to ride it through again, you know, like it's hard to say what it is, but it's just this energy in your body. And I feel like here I want it to be like water and flow. And now it's been flowing for a bit. So now I want to short sentence and snap and and it's it's both the rhythm and like what kind of images I think a lot about like it's playing chords. Like if I'm if I'm writing something that's very intellectual, I think it's quite nice to maybe add something about the form like like bring in a different chord. I really like the sort of the justosition of different colors.

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>> That that's something I think a lot about like how to >> sort of bring elements that seemingly seemingly doesn't work together like and bring them together. So like you it's rhythm. It's it's mixing different elements. But but yeah, it's all part of like just listening with the full body

How Deep Conversations Generate Great Ideas 35:40
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and like how does this feel? >> Tell me about that. Learning to pay close attention to your thoughts, to your feelings. >> How do you cultivate that? >> Feeling takes time. You have to >> you can't just write and then read it rapidly. You have to like actually just sit there and like maybe close your eyes and and just be silent for 5 minutes, 10 minutes maybe. Sometimes I'll sometimes I'll write a piece when I'm out walking.

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I'll just walk and I'll get a rhythm in my body and I'll just listen to it until I feel now it's ready. Right now there's there's that word that wants to come out. like it's very hard to talk about but but but it's just uh trusting that if you sit you don't have to labor your way through it. Like sometimes it's so tempting to just sit there and fix things and move things around, but just like it's okay to stop sometimes and just sit with it or just let it or maybe if you've s been with it for a long time, maybe just let it simmer in your subconscious for a day or two. Like various ways of slowing down.

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>> How do you get better at finding interesting ideas? A really good idea is to have good friends that are interesting like because conversations are and and that gets back to what I was saying in the beginning like uh it's gotten so much easier with time because I'll write a piece now where I have maybe a first rough sense of an idea and then I'll get like five, six, seven emails from interesting people and I'll talk and that oh you should read this book and I'll read that and then we'll jump on a Zoom call and talk about it and there's like something in this kind of playful full back and forth with other people where I I often surprise myself reading odd books. Uh books that uh are kind of off the beaten path are usually good because I feel good ideas often come from this kind of collision between different areas. So so I so I'm I'm really nerdy in sort of machine learning >> uh for example and I find that to be

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because I'm a sort of a literary guy. It's interesting to go to a very different field to go into like machine learning or mathematics and like pull ideas from there and like crash that into like poetry or something else and there's these strange connections often generate ideas. So by reading kind of widely and in strange directions uh usually sparks a lot of ideas for me. Uh and again patience, patience all the time. Just like allowing the head some space, just like going for a four-hour walk, like having a lot of good conversations, writing in my journal, reading some books, and then just going for a long walk, and just seeing all of those things kind of slowly collide and merge in my subconscious until something just like, wow, that's a good idea. like after a while I've felt like I'm almost kind of constructing my life around how can I have more of those experiences. So like for example not having internet on

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and uh spending more time talking with certain people like trying to shape a life um that enables this kind of left field thinking. >> Yeah. It seems like a big part of shaping that life too is just giving up >> Yeah. so much so that you can really focus on the thing that you value. Giving up things in music, in programming, in inerson connection so that you can really just focus on family and writing. Those seem to really just be the two things, right?

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>> Yeah. He said this well of if you're going to be really successful at something, you need a good theory for what you're going to give up and not do. >> Yeah. My experiences li in life is that things get better the deeper you go >> because there's like more and more richness if I've been with my wife for 12 years and we've spent so much time talking and we were like 10,000 hours into our conversation now and it just gets better and better like I mean it's really fun to talk to you here but I'd love to know where we would be 5,000 hours from now cuz I I bet that would be even better and more interesting.

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>> Yeah. So, so I that's my experience like whenever I stay longer go deeper on a craft on a relationship. So, and and and once I had that realization maybe at 25 or something I realized okay so that means if I want to be able to do that I need to say no to a lot of things because either I spread myself in or I go deep and I want to go deep. So, so I I decided to like focus really hard on my family and my wife and and uh after some soularching I figured like writing is the thing that just gets to the deepest place in me. So I I put music mostly to the side. I put programming mostly to the side and just decided to go really deep. And um it takes some courage to let go of those things because you look weird when you do that. It's really easy to sacrifice the wrong thing because you haven't actually sort of sat with yourself and like uh figure out like what's the hierarchy of values in your life. Uh and um and when I say

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hierarchy of values so of course like like now finally we have a car like of course I want to have a car that's really nice to have a car when you're kids and drive them around. But at an earlier point like when I had to decide should I write or have a car then I pick right and and now I don't have to make that choice now I have a car and I write but but like what's the hierarchy here and and it's very easy to be confused about the hierarchy and like end up putting things in the wrong order and like sacrificing the thing that really makes you alive and the thing where and I guess that's one of the good things about writing because writing is the practice of sitting down with things I probably helped me like figure out my ranking of things by actually writing about it like what do I actually care about like where where did I feel alive what am I willing to compromise on and where are my like strict ethical

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boundaries all that when you talk about

Why Breaking Grammar Rules Improves Your Voice 42:02
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the work of writing we've spoken about paying attention looking but then there's the other part of it of figuring out what something is asking of you what do you mean by that well I I always try to write from from from a deep personal need. Um so so I I I never like pick a topic because I think this is going to be people are going to like this or this is going to be anything like that. I always bring from like how could like there's it was always rooted in some deep personal needs like how could I become a better father? How could I >> how could I uh like I I've been feeling overwhelmed recently. Like how can I think about that? Like it's it's it's I'm starting from some thing that if I could get clarity on this, it would improve my life or it would let me serve my loved ones better. So I'm always trying to start from that place. Like the writing that I want to do is asking me to become a better person. It's it's

43:08

like it's I feel some some something almost scary that I have to confront like I have to grow and change and that the the writing is sort of um it's almost like this metaphor like the hero is journey like going down into the cave. I almost feel like >> at least with all my big good pieces it's like I'm going down the cave. There's like some fear I have. I have to go down because I need I know I need to confront this. there's something that is kind of holding me back from maybe experiencing things more deeply or like being more present with my wife or whatever and I like I there's something here that I don't understand I need to go down and >> is a puzzle the right word or is it something else a puzzle compulsion how would you describe that >> yeah it could be a posture but also a need sometimes the answer is obvious but you're I I need to sit with it to kind of uh let go of the fear so sometimes

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like I it's like that with a lot of wisdom, right? You know what to do already, but you're afraid for some reason or you are confused and sometimes it's just so sometimes it's a puzzle. I like how should I get all these things to fit together. But but sometimes it's just I it's time to confront that fear and like uh get clarity here so I can um like shoulder my responsibilities better. And when you're doing that, you're trying to create language and describe whatever it is that you're trying to describe. How do you feel like Danish is different as a language from English?

44:43

>> So, I speak Danish and Swedish. Uh, >> are Danish and Swedish pretty similar? >> Yeah, they're like 70% the same and like English is more like 20% the same. >> Okay. Okay. So one thing I miss uh when I write in English is that English grammar is much stricter and the word order matters a lot more. So you have to put things in like a precise order in English whereas in in Swedish it feels like I can just move the words around.

45:11

>> Whoa. >> In whatever order I want to. So if I want to say like the the boy held the ball that had been thrown through the window, I could also say the boy held through the window from ball. uh or like I can change the order in almost whatever way I want or not not whatever way but it's much more freer and and I remember like when I wrote in Swedish I really loved you doing that just like oh I don't want to have this word here I'm just going to move it over here and then that like I could just move things around like like on a scale and like I want the rhythm to be more like this I'm going to move the words and in English it's like I can't like if I move it here it's ungrammatical if I move it there it's ungrammatical >> I think we should all be just way crazier with grammar >> especially in LLM age.

45:52

>> Yeah. >> Cuz like LLMs >> are just another force for standardization. >> Yeah. And one of the things I often think about like if English is poised to become like the global language, then we should like make an effort to like bring in all the weird innovations from all the other languages. Like bring in the like the weird grammar from Turkish and the like the cool words from Persian and like everything should come in. We should allow oursel to be wilder. But it's hard to do because I have some things I could do like I could bring in from Swedish. But whenever I do it looks like I'm wrong and you look stupid when you do it. It's it's like a hard thing to do cuz you don't want to be ungrammatical because that looks stupid.

46:36

>> Are you excited about what LLMs are doing to writing or are you annoyed by it? Do you use LLMs in your writing? >> Very little of what I put in the essays have been touched by LLMs. I might do things like uh because I I'm a second language, I don't know English all that well. So sometimes I'll just be like I mean that word I'll describe a word and then they'll give me the word because I don't know the word or I'll ask it is this grammatical or whatever. I'll do things like that to help me talk English. And sometimes I'm not happy with a way something is phrased and I'll be like, "Give me 10 versions of this with different words to just kind of get me out of my head and like see different possibilities." So that's basically the only time I actually like end up putting something into the and that's maybe like 1% of my words. Uh, but I do really love using them and playing around. I'm really nerdy with LLMs and have been

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like I've been a power user of LLM since like at least a year before SHA GPT. So I'm like really nerdy uh like back when you had to like get like a special access from OpenAI and go into this like really weird looking interface and play around. Um yeah, I found it find them to be incredibly interesting. I've been somewhat underwhelmed in what they've delivered so far. It feels like they they should be able to do something really interesting >> and I haven't seen it yet. Like I've seen some interesting images being made.

48:08

I've seen some interesting music being made, but I've not yet seen any good literature be made and it feels like we should be able to do that. But they are incredible tools for uh things like research. I they're starting to get to the point where they can do some basic editing. So I like have a prompt where I ask it to go through like uh these are some words that I overuse. Can you point out when I use them? These are other things I want to think about just to help it remind me so I don't have to keep all of the things I should look out for in my head so I can just store some of my like bad habits in a prompt and like ask it to look through my essay to see if I'm doing the bad habits.

How to Write as Discovery 48:49
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>> There's one version of writing which is you're writing to give an answer. are saying here's how you find an interesting partner or the right partner for you whereas the other one is how do you do that and it's more exploratory >> I don't know if you have strong thoughts on this >> I've definitely been trying to move toward a second kind where this kind of reflective uh um kind of vulnerable searching through the space I don't have the answers I find that type of writing to be much more invigorating to read I also find it to be.

49:25

There's something really interesting about seeing another person grapple with something. I I I've learned so much by by reading some of my favorite writers and just seeing them grapple in real time. Like they'll start somewhere and then they'll realize they're going down a dead end, but they'll leave that in and say, "Wait a minute. I'm wrong here. I I'm confused. Like I feel And >> I love it when writers do that. They kind of keep it in and they almost like we got our turn the car back and go back down the road. Okay, that one didn't work. Okay, here we go over here. But there's something about it that feels very it feels very sincere. And this is the problem with editing. Sometimes people edit that stuff out.

50:09

>> And there's a certain kind of writing when you're writing to answer a question that you're asking. we can kind of go on the process of exploration and discovery with you and by definition the part that process has a lot of fits and starts and you don't want to keep all of them in but you do want to simulate the process of discovery for your reader and when you do that it's sort of like hey come here come here come here hold my hand I'm going to show you this and we're going to go trace the steps of my discovery >> and it's it's intimate Yeah, it's almost like two different mental states. Like when I write, as I've been like moving more and more toward like trusting the reader, being more or reflecting honestly and deeply and like allowing dead ends to hang in there. I've had to almost like move to a different part of my body.

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>> Oh, to to to write in that way because it's like that's very vague. It's hard to say what it is, but it's like I have to go to some place where I relax a little bit, like where I let go. I'm not afraid because a lot of that like trying to be smart and like trying to be like going straight to the point is is is is fear of looking stupid for me. I think uh where like or oh people are going to get bored or like >> it's funny that you talk about this fear of looking stupid because I have that too. But I rarely read writing and think, "Oh, that person looks dumb."

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I'll sometimes say, "Oh, that's a ridiculous take." But it's actually just the take itself that I think is stupid. But it's rarely like the lack of polish that makes me think that person is stupid. Actually, I often find that the lack of polish is quite endearing to me. But then I sometimes get get at the keyboard and then I'm like, "Oh, I need to look so smart and all buttoned up." >> Yeah. You know, it's it's it's really interesting. Yeah. I mean, I'm super forgiving. Like people can be like almost monsters. Like like sometimes like some of the things that Carlo Vnowskirt does in his books, I'm like that's you shouldn't have done that. But it's like when I read it like I don't like that's okay. Like I'll keep read like so I I don't even judge when he does like really stupid things but then I'll judge myself for something bal in comparison.

52:33

>> Yeah. Yeah. Tell me about the fragility

Why You Should Protect Your Early Ideas 52:34
52:36

of young ideas. >> Yeah. There's this beautiful line where Johnny IV is speaking at Steve Jobs funeral and he in his beautifully eloquent voice talks about says that the thing that Steve Jobs understood better than anybody else is that young ideas are so are so fragile and he starts referring to them like a like almost like a little bird, >> you know, so precious. And there's definitely room for critique in the writing process, but when critique comes too early, it squishes >> the ideas. And that's what Johnny says that ideas are so easily squished. Yeah.

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>> You have to honor them early on. >> Yeah. You have to shield them, right? from and and often the thing that kills ideas are like social expectations. M >> some of my best ideas when they come to me they're like almost nothing could be just like sometimes almost like just a color or something like and if I were to come to you call you David I have such a good idea I want to write an essay that's going to be like has a feeling that it's pink and you're like what are you talking about you know but that might end up being a really good cuz like maybe like I'll sit with that feeling pink or like what does that you know whatever and that might lead to a really good essay but if I tell it to you I'll be like that's not even an idea like pink like uh so and if once you say that I'm going to be yeah yeah yeah sorry like and and it's going to be really hard for me to be excited about that idea after you've told me it's

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stupid I mean someone like you >> but uh so so I find that like often I need to really give ideas space to just like uh live like in my diary or just like live in my head as I go on long walks and just like trust that this is going to grow into some something it's just like I was like talking about like these dreamy dream images especially with poetry but also with essays it's just like often like it's like a small image and you just kind of like David Lynch has this wonderful thing where he talks about when he comes up with his films it's he's talking about like he gets these like fragments of images and then he'll put them on a hook and then like lower them down into his subconscious and then he'll catch another piece and then another piece and you just have to trust that process cuz if you just show that first piece like That's nothing. But but that's the bait for the big >> Would you say that it's like turning

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a net into a line? >> Yeah. >> What does that mean? >> Ideas in our head, feelings, images are not linear. So, so if you are thinking about like where you grew up or whatever, you're not like seeing that as a story like, oh, I grew up on this street and that. It's not one thing after the other. It's it's it's everything at the same time. There's the like this maybe the smell of your room and then maybe it's like things you did and and then these things are like superimposed. It's it's like and especially like in the subconscious it's like everything at the same time. So it's like a net a network.

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It's like nodes connected. And then when you're writing, you somehow have to make a really tricky transition cuz you're going to take this thing that is actually like a cloud or a net or a network in your head and then you're going to turn it into a string, a line because writing is one word after the other and that's very different. And then if you do really well once you read it, it expands back into this this net in your head which cuz good writing is is not just what is on the page. It just starts these reactions in you and it sets off thoughts and emotions, right? This cloud of associations in you. So so that's and that step to go through that like making it linear is really hard. So, it's like you could imagine it almost like sometimes the process I do is that I I'll literally like make a a cloud. Like I'll write notes and link them together.

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Like I I use obsidian. So I'll I'll write like 50 different notes and there links between them and I don't know like which is the start and which is the end but I'm just getting everything down the whole kind of network of ideas. And then when I write I have to decide okay I'm going to start there and move for this link here and there and and try to find a path through this network which is like how can I find a good path through this thing that's actually like a spider web uh like which thread should I walk on because I want to walk across the spider net on the the the web in such a way that I like hit all the most important points so you get the feeling for the whole net but I can't give you the whole net. can only give you one walk across the net, but like what's the right walk to like do justice to the full net >> and make that come alive inside of you?

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>> What's the role of mystery in your writing and thinking process? >> Mystery. Wer Horog has this like wonderful way of talking about it. He says that you you want to have like ecstatic truth like not like a an account >> ecstatic truth. >> Yeah. cuz like he he says too many like documentary filmmakers for example they're just like they just want to capture the truth like like an accountant and this and that and he's like no but sometimes you you might have to frame things and maybe invent a little bit like and you can argue the ethics of inventing things in documentaries or whatever but but what he's saying is that like by by inventing a little bit and adding things sometimes he'll add like a fake Pascal quote like it's not Pascal he's he wrote it himself but he says it's Pascal because when you see it's Pascal, it's this old quote.

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Then it kind of that elevates it so you're ready to hear what's said and he's like playing on these kind of emotional things and and sometimes like he has a documentary called Little Deer Needs to Fly and and like uh there's a it's this guy who's been he was captured in Vietnam and and he had to run through the jungle for months and like it's incredible story and then in the documentary you follow him to his house and then he gets to the door and then he opens and closes and opens and closes the door again and again, right? and and he says like most people take this for granted like but for me like opening and closing a door is a big thing because like I've been in prison camps I like this is such a big thing and it's it's a very strange moment and you're like but it's a very affecting because then you kind of feel wow like a door being able to just walk out of your house it's it's a privilege and

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>> and there's like a deep emotional moment there but it's nonsense like he he doesn't actually do that that's Verog like I told you to open and close the doors. It's just totally fake. He that's not like it's a documentary, but like he doesn't do that in real life. But Hersog says like maybe you should open close the door because that's going to create this resonance in the movie that's going to make people more able to see the deeper truth of the idea here. And I I usually don't invent stuff in my writing, but I like to like add these colors in a way to like set up a certain emotional color so that when the idea comes, it just like hits you in a different way.

1:00:11

>> I can't believe how much sesthesia is in the way that you talk about writing. You know, so much has been in color and in >> Yeah. >> in sound. I see it. I mean, I see it. I feel it in your writing. I read um a book called u the psychology of invention in the mathematical field by a mathematician called Hadamar. Incredible book. It was written maybe early 1900s and uh and he made made an observation that like the greatest mathematicians do not think in words or symbols. They they think like in kinetically they feel it in their hands. They feel energy fields in their body. And it's only once they are kind of fairly far along in in solving a mathematical problem that they actually write it down because it's too clumsy to work with words. It's much faster to move with these kind of intuitions in your body. And I was like, "Wow, that's so strange. I wonder if I can write an essay without words." And so I I know

1:01:12

that was hard. as I I lay down and like close my eyes and like lay for like half an hour, like I'm not going to say a single word in my head. I'm try to like keep my voice out and see if I can just feel the emotional currents of of of the piece. It took some practice, but like those are just kind of weird things you have to do, right?

The Strange Writing Experiments That Actually Work 1:01:31
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>> What other weird things have you done? >> But I'm always like playing around with things like can I what happened? Like if I how does my writing change if I wrap by hand, if I walk as I write, if I listen to this music or that music or if I uh write really early in the morning or really late at night? Like I'm trying different things all the time and like running some experiments on myself sort of to get a feel for how it affects me.

1:01:55

You know what you're making me want to try is when you do um if you ever do like assisted MDMA therapy, what what'll happen is you'll wear these big headphones and you'll listen to some, you know, beautiful nature sounds or sort of like kind of tribal fluy music >> and then you have this eye mask and you lie down >> and you're making me just want to do this. And what's fun is if you really have good noiseancelling headphones, you actually can't even hear yourself talk.

1:02:26

So like what would it be like to talk out a piece, but you can't even hear yourself talking? >> I don't know what would emerge from that. It's just I kind of want to try that. >> Be fun to do things like that. I'm I'm doing things like that all the time. I'm not so much with MDMA, but >> I mean I I'm not saying you need to be on MDMA. It's just doing speaking out of piece is one thing. That's a great trick, but I've never thought about speaking in a way where I can't even hear myself speaking. And then >> who knows, you almost enter um it's sort of like what Salvador Dolli would do when he was painting. He would enter a kind of dreamlike state and then I think I don't know if it's apocryphal, but would have an apple. Then the apple would fall. He'd hear it. He'd wake up and then right in the second of waking up, >> well, what are the ideas that emerge?

1:03:14

>> Yeah. I think like the my two favorite pieces I've written this year. So, one was um I wrote a piece, what was it called? It was called uh sometimes the reason uh you can't find the people you like is because you misread the people you know or something like that. >> Yeah. Yeah. >> Uh and which is about like my best friend. >> Your best friend. Yeah. >> And and the and the way I wrote that piece was this was when I was kind of into exploring how my cognition work as I write. So, so I I just lay down on my sofa and I thought like let's just just think about my friend. I had no like idea for the piece. I was just like I'm just going to think about my friend. So I lay down like close my eyes and I started talking aloud and just like almost like a psychotherapy session. A lot of writing feels like psychotherapy in a way. just kind of walking through my thoughts and feelings and I was just

1:04:03

thinking about what I felt about him associating and and I talked for a long time a lot more material than in the essay but then at some point I felt like this um energy like the there's something like I felt like a border around like there was a part of a section of what I was saying that felt like this feels like a thing because like sometimes something just feels like a It's hard to explain, but I know what you mean cuz like I was saying a lot of things, but I felt like what that part that part of the conversation if I cut away everything else and just keeps that part that's actually a thing.

1:04:40

>> If you were to teach a class on writing, how would you structure the curriculum? You got a whole semester. Like what are the core things, the core lessons that you would impart on people? >> Becoming a person who writes well, it's it's like it's not a skill set. It's it's about like um it's it's deeper than that. It's a become becoming a certain type person and like being connected to yourself and so on. So I think uh I know like Verer Herszog when he did his film school like one of the things he would say is that like to apply you have to walk from Madrid to Kiev uh by foot or like he didn't actually do that but I was like a joke and I think that's a pretty good idea like cuz I think you have to do some kind of ordeal almost to like shed a lot of um everyday mentality cuz we have all these expectations of social expectations and just going out there and maybe like being alone on a really long walk or

1:05:43

like doing something really hard going to war or whatever like something like that sometimes is needed to it's not it's not if you have that if you have a perspective and if you have like a groundedness in yourself then like figuring this out the stuff with adverbs and all that is kind of easy. The hard thing is like having a connection to your lived experience and a certain boldness in pursuing that and like not caring too much.

How Courage Becomes Your Writing Bottleneck 1:06:11
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>> Yeah. How much do you feel like your ability to write well is limited by boldness and courage? >> Yeah. Yeah. That's Yeah. That's probably always the biggest bottleneck. >> Always. >> Yeah. I think so. I mean I I often like try to tell myself it's some other thing because it's really painful to work on boldness because it's scary. I mean uh so so I often tell myself, oh I need to get like better at coming up with metaphors or I need to get better at openings or whatever. But that's usually an excuse cuz if I can go deeper uh that that's usually the better place. um when writing became like a serious practice for me or there are like some moments in my life where where I can see that uh the realness of the writing has been dialed up and like the first was when I was 15 and a friend of mine committed suicide.

1:07:04

>> Um and that just like obviously blew me wide open and and the way I kind of reacted to that was by writing music. So I I just like before that I'd been a kid and playing around. But like when that happened I I just felt I need to write and I I started writing music and then that evolved into poetry and evolved into essays and it was just because it came from such a raw place such it like once you realize like you could as well be dead. uh it doesn't matter like like it's it became so real like I it helped strip away a lot of the nonsense because could as well be dead you know and then >> and then the second kind of point where it deepened in a substantial way was when I was 21 or 22 I went to Bolivia and uh and I was I went up in into the mountains and um I was staying like three weeks uh in in this village with some IA Indians and and like they didn't we didn't speak the same language that

1:08:09

like they would play some abba music for me and like Sweden, you know, and >> like dancing queen. >> Yeah. Yeah. Exactly. They love that stuff. Uh they're obsessed about ABA and and but I had no one to talk to for 3 weeks up in these like really arid mountains. And when I was there, that was like then I remember like I got like a a notebook like that someone had made like a homemade notebook and I I started writing and just obsessively writing and before that writing had been still sort of playful. I'd been making music and making some poems but then it was just like something flooded through me and that I think was because like I was alone. I was there was no expectations like every every role I was supposed to play at home like how I was supposed to feel all of that fell away and when there was nothing left the thing that kind of bubbled up to the surface that I I need to write >> and that writing also and then if you do

1:09:07

that for 3 weeks if you sit alone in a mountain and write for three weeks you're going to be a little crazy afterwards because you're going to go to different parts of yourself and you're going to like train different parts of your brain almost like short new paths in your head. So like uh when I came back I was like I ne I couldn't never really get back in fault because it was like I'd seen another thing and then so so there's like these moments where it kind of deepens uh and and and I think like loneliness is a important thing like >> I asked you earlier about mystery but the word that you use is loving curiosity and cultivating that sense.

1:09:51

>> Yeah. Yeah. I think you need to sort of trust the world. >> Trust the world. >> Yeah. Huh. If you can like get to that place where you Yeah. Yeah. You feel like I'm really curious and in a very warm way. Like I'm not I'm not like looking at this puzzle because I I want to win. I'm not going to prove to others how smart I am. I'm just like, what's going on here? This >> It's like making yourself porous. >> Yeah. And the thing about porousness is there's just holes and anything can get in, including bacteria.

1:10:27

Yeah. Virus, whatever it is. But also when you're porous, something can move you. You're you're you're giving reality an invitation to get in the front seat of the car. And you're kind of in the passenger seat now saying, "All right, >> I'll go with you." >> Yeah. Yeah. Exactly. Exactly. And it's it's it's hard and because it's this strange combination of being very porous and very firm at the same time. >> What do you mean by firm?

1:11:00

>> I mean, you you have to have a really kind of bold conviction in in your values. There's this is almost like paradoxical, but but you see that with like great poets or great artists of any kind is they're they're very open to the world, but they're also like not going to let the world dictate who they are and where they're going. So, so it's it's cuz it's very easy to be like very loving and just like inviting everything in and being agreeable. That's because that's not what we're talking about.

1:11:32

there's this other strange combination of mental states where you're like um given this and I guess like I mean you're Christians like I think Jesus had a lot of that cuz he was like seeing everyone he was like very loving but he's also like very firm in in a sense like he knows what he stands for right heck yeah >> and that combination it's it's a very odd combination uh and uh I think that's probably why why Jesus is such an interesting archetype uh one of many reasons like but he embodies this very complex uh set of characteristics uh that makes him into like an interesting character to meditate on because he's combining these traits.

1:12:18

>> Yeah. People always say, "Oh, Jesus such a sweet, loving guy." It's like, "Have you read the Gospels?" I mean, of course, he has that, but Jesus goes hard. Yeah. >> You brood of vipers. And yeah, you're right. There's a there's a tension. It's it's neither this thing or that thing. It's the two of them in harmony. >> Yeah. Yeah. Yeah. >> That it really comes together. Right. Like even in music, it's not a chord that's beautiful. It's a chord progression that's beautiful. It's not a word that's beautiful. It's words together that's beautiful. And that's the art. That's what's so beautiful about life is it isn't just like you just do this one thing and then it all works out. I wouldn't even say that it's necessarily like the golden mean. I'd say it's the pairing of things together. Like you know you ever one time I was in a desert and I had some chocolate had some dark some dark chocolate hot Mayday in the

1:13:20

Texas desert. Sweltering heat. I'm sweating and the dark chocolate made my mouth so dry. So dry. I mean to the point where you just want to hit the eject the eject button on life. And someone handed me an orange slice and I put the orange slice in my mouth and I was like, "Wow." And that's kind of what it's like of the the the orange slice is so much better as a reaction to the chocolate. And you were

Why Boring Truths Make Powerful Writing 1:13:50
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talking earlier about how in your more intellectual pieces, you you'll often write about the farm. >> Mhm. >> That's exactly what you're saying. The farm is the orange slice. >> It's the sequencing of things that kind of produces it's um and that's what ritual does too, right? Ritual. >> Ritual. Yeah. So, so you'll you'll sequence things in such a way that it kind of produces some deep state or deep insight or whatever. And uh and and I I mean I haven't read the Bible much, so you're probably much better at this than I am, but out but but but but but I it's really interesting to think about like um the New Testament as a sort of um as an essay or whatever. It's like it's trying to convey certain truths.

1:14:34

>> Yeah. >> H but it's using a parable. that's using but it's some of the things are written out I imagine like uh literally word by word but it's kind of framed in stories and there's and it's it's but and it's really is trying to construct because the idea that is trying to be sent over to the reader or or or the believer is is very very complex and it's this again this web very complex set of ideas and and how do you like compress press it down into uh even like it's a fairly long book, but it's still a short book for the set of ideas that is trying to be committed. And so they're they've found this really powerful way of like combining poetry and images and uh straight truth and and all these in a in a sequencing that will produce an effect in the reader. And then of course there's the whole kind of community around it and how you read it and the structure. But it's really interesting. It's you can't just when it

1:15:34

comes to these really deep truth about how to live, you can't just say them. They're not like uh physics or whatever. You can just like write it down. You have to construct a sort of some kind of experience. >> Well, uh David White, the poet has a line where he tries to define poetry and he says that his definition of poetry is language. Poetry is language for which we have no defenses. >> H M okay. So what does that mean? It means that with certain kinds of writing we know how to deal with it. It can't sort of overwhelm us. And then every now and then you'll read something, you'll hear something that just strikes you. It just strikes you. It just takes you back. It's the same thing in music, right? And so what's going on there?

1:16:25

Something about the sequencing of the ideas, the way a story is told, the way a sentence is written, it is somehow pierced into the core of who you are and touch something. And when we have like a visceral resonance with something, I think that that's what's going on. It's poetry is language for which we have no defenses. >> Yeah. and and and the way you do that it's it connects to the kind of stuck in reality, but in this case it's the subconscious like what what artists uh are really good at doing is they they're they're able to tap into sort of the subconscious or like these em deep emotional states and like capture that >> yes very strange thing and like find some combination of words that that produces that effect and um I find the most interesting ideas to me, the most alive ideas are in some ways truism, some ways obvious. Uh I I like to write about ideas that are kind of obvious because um

1:17:31

because like the deep truths are somewhat obvious like you should like be try to be a good father, you should be kind, you should uh honor your commitments, whatever. Like these are kind of obvious. Like if I wrote a post that said you should be kind, like that wouldn't work. But but it's a much more but and and something that often happens is that like people don't write about these obvious things because they sound boring. So they end up saying something smart instead, but it's not as important as the boring thing. And but but the boring the boring thing needs to be pierced through to your heart. So, so when you write about the boring things or the obvious things like you should be kind or whatever, then you have to really construct those complex like piercing poetical ways to just make that thing alive in you. It's it's like you might know it, but you have to like make it real inside of you.

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And that's that's the kind of writing I'm going for. >> Yeah. And the thing is you can feel as a writer if you're doing that because often when you say to someone, hey, what are you writing about? It can feel trit, but somehow the the way that you're writing about it just feels so alive. And often that's a story or whatever it is that now makes it feel fresh and vivid. And if there's no surprise for you as the writer, no excitement for you as the writer, then there's no surprise and excitement for >> Yeah.

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>> for the reader. >> Yeah. Yeah. I want to laugh and cry and like be elated when I write. >> Yeah. My friend Paul Millard, he I once asked him how he wrote his his his memoir. And he said, "I just went on a walk until I started crying." And basically what the pathless path is is it's a collection of things that I kind of just wrote in tears. >> Yeah. >> Yes. Exactly. Because until you How do you expect somebody else to be moved by a piece of writing if you aren't moved by a piece of writing >> Yeah.

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>> yourself? you are the only person you can observe that closely. So, just like wait until you see a reaction and then that's that's the writing. Uh um cuz you can't like if you're it's really I mean you can with some tricks. I could probably figure out some ways of like making some people cry by doing some tricks, but but that's the fake, right? The re really real stuff. You just like you feel it and and you get it on the page. You talked about a little bit

How to Write From Your Subconscious 1:19:54
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earlier about ideas being brittle, but you also used the word crumbling, that ideas can crumble and then after the crumbling, the light comes in. >> When you're just having a conversation or when you're just thinking about things, uh, ideas kind of tend to float a little bit >> and and um >> and if I say something and you say, "Well, what about this?" Then I can say, "Oh, that wasn't what I meant." it's just kind of floating and and and that might be a good like social strategy for never losing your face, but it's not a good idea for improving your thinking.

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And and and what I like about writing because when I write it down on paper, like I can't fool myself like that's that's what it says. That's what I wrote. I can't pretend like I was something else and because it's on paper and and that means instead of it like morphing a little bit or changing a little bit and what I said now it's wrong instead and and it breaks when when once I like critique it and say it breaks and and and when I've written something down I've critiqued it it's fallen apart that's again like I enter this zone of confusion and that's where where light comes in because in the confusion it's sort of I'm letting go of my preconceptions. I'm kind of moving beyond my mental models and I'm confused. And now when I'm confused, it's like I'm taking in data in a more raw form from reality. And >> and and and when I do that, I can learn because when we have our mental models, we're filtering all the time.

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>> All the time. >> Because like if you have decided that everyone who's on the political left are stupid, like you're going to like filter any anytime someone on the left says something smart, you're going to filter that. And every time they say something stupid, you're going to remember that. But if you can like get to this point where you're you've left your mental models, you're going to see things in a more high resolution way. A lot of if you were to say like go to dinner tonight and someone says, "Hey, what'd you learn from Henrik?" The number one thing I'd say right now is that you spend a lot of time in your writing process getting to a pre-linguistic state. Yeah.

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>> How much have we spoken about bodily feelings and color? And when you're pre-linguistic, you're not operating inside of a mode of category. And because of that, what you're doing is you're getting much higher resolution. You're getting it's like a giant photo that hasn't been compressed. The compression comes later. And most of the way that people speak is in a lot of compression, right? Like if you say, "Oh, the political right, tariffs."

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You have compressed so much. But what you're trying to do is get to a pre-compressed state as you observe reality and look and look and look and look and then just let that process of observation happen over a long amount of time, >> sometimes a year. You say it needs to live inside my body for a year. >> And then after a year or two years, then you'll do the work of compression. And I think that's really distinguishes you from how most people think.

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Yeah. Yeah. It's it's really important. Yeah. I feel like my my sort of toolkit is like a series of exercises for like breaking my own mental models. Like I'm I'm trying to so so I write things down and I critique it and I I have uh I have various sort of questions I ask to com like I want to confuse myself. I want to like find counter examples. I'm I'm doing all these sorts of things to make myself more confused to get the C. Yeah.

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and and um >> is more confused. Is that the right way to say it? Why confused? >> Um so when they do um like accelerated accelerated expertise training like in in the US military like when they want to get people to become really good soldiers very very fast like they have these programs where they get people up to like a elite level in like a few months. uh what they do there is they're trying to make them sort of maximally confused.

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Uh so so so they'll do case studies, they'll put them in simulations and case studies and uh they'll not give them like any theory or any explanations of what's going to happen or how to interpret it and they have to sort of interpret it themselves. And once they like and then they throw another case on them which is like totally breaks whatever they came up with on the first one and they're like trying to like avoid because we we have this tendency of forming what's called like a knowledge shield because certain types of mental models there are they're good enough to explain most of the data we see and once that they're good enough they we start to sort of ignore everything else and you want to and and like the if you want to have like a accelerated ated learning curve. You want to avoid forming knowledge shields.

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And the way to do that is to like put yourself in situations where where you get so confused that you can't like really form any coherent stable mental models. So that's what I mean by confused. It's it's like you don't have really any stable mental models. You have maybe like a half working mental model here and another here. It's like this kind of unstable state. there's not a like a full coherence yet. So, so that's that's what I mean by confused maybe like no I I don't mean like you've done a lot of drugs and everything is upside down. It's it's this sense of >> I don't really know. I have a rough sense maybe what's going on, but I I can't explain what's going on here. That that's a like a good state to be in if you want to be open.

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Can you describe for me just where you live and where you write? Like, break that down for me concretely. I mean, I know that you live on a remote island in Denmark on a farm. I imagine there's your wife there. There's two kids. Paint the scene for me. We have like two houses and right now we have like mold in the main house. We're living in the stable. Uh so so we're living in a stable on the upper floor but we've put some uh nice house and then in the morning so I get up in the morning I walk down into >> What time you wake up?

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>> Uh well I used to be very disciplined and go up at 5 but uh and start working at 5:00 but that was when I had a job because that was the only way I could fit in. Right. >> Was this when you work at the art gallery? >> Yeah. Yeah. Exactly. So then I would write in the morning until maybe from 5 until 9:00 and then I'd go into work. Uh but now I work full-time. So I start at 7:00 and uh so yeah, I go down and I sit there in um what would used to be like the woodworking room uh in in in the stable and I and I write or if I'm sort of stuck, I'll lay down on the sofa or I'll we have a fairly big farm, I'll start walking on the meadow and up and down the road or go walk in some nature reserve. I like to do a lot of walking.

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So, so it's um so I I usually do that between like seven and three six days a week or something like that. And then in the afternoons I usually hang out with my kids for four or five hours and like try to be a very present dad because that's like a very grounding thing for me. But it's really nice integrated. I mean, it's a enormous privilege to be allowed to live like that because it's everything is integrated in everything else because like I'm sitting on the farm writing and if I get stuck, I'll go out and like fix uh some brick wall that needs to be fixed or I'll hang with the kids and like the writing feeds into me being a better dad and like being with the kids gives me ideas for the writing.

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So, it's a very kind of integrated thing. But yeah, it's a beautiful place with like almost two small houses and we have a little wood with beach trees.

How Writing Summons A Culture 1:27:46
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>> Well, I want to close with why write, why you write. And what I really think is fun about your writing is sometimes you'll just completely break the rules. But there's no place that you broke the rules more than the title that you have of a piece, which is both the thing I want to talk about, but also just make a comment that you just had the audacity to title a piece this, which is a blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox.

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>> Yeah, I think long titles are underrated. like most people only read the title, you know, so you could might as well, you know, be useful and put all of the important information in the title. So then they get that at least. Um and uh and that insight in itself, that post, this idea that what you're writing is a search query. That was one of the things that has just blown my life wide open because >> I mean I started I mean as we talked about a lot today I'm writing because I'm trying to sort of process my own life. But then like when you once you put that on the internet it starts it can sort of move out like across the social graph and find other people who are into the same thing. And all of a sudden, like I remember it was this time like in in December 2021, I at that time I had like 50 readers and I was starting to get like emails from really interesting strangers from all over the world, you know, who were had

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read the same books as me and had done that and and and I started talking to them and it's almost surreal because like you I'm putting these words out and they are summoning like a culture, a friend group like and then once I have met these people that I start get changed by them. So like I write something that pulls people in and then I I become like a different person through meeting them. So, so writing becomes this almost a process of like summoning a culture like the the specific culture that can hold me because I think a lot of people myself included like never maybe felt truly at home in the cultures they were in like oh my small hometown it's not really mine this job I have is not really me and to be able to summon a place where being your full idiosyncratic authentic self is just like the way to be which is like encouraged. It's a a very lovely feeling to have a space like that where you can

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feel like safe in exploring the parts of yourself that feel alive and and then having these conversations and growing and and and changing. So, so that was like the big big gift and in retrospect I mean I'd written for a long time before this happened and but I had been following sort of a conventional logic before this which was I I mean I'd written for magazines and so on and and I had been taught to sort of write for a mass audience that you should kind of simplify things a little bit. you should take out the weird stuff. And once I let go of that, the interesting thing is that then my writing became weird and too long for most people. So most people read it and were like, what is this?

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>> But the few people who read it, they they were my people, right? They really loved it. And then they started sending it to their friends and it became this kind of flywheel. And it's I it's something I wish for everyone like to have. I mean, not like a big successful blog, but just like have a few blog posts out there so your people can find you and like have these meetings because I think there's something so deeply nourishing about being seen in your interests, in your curiosities, in your values and like being held in that and like being able to rest in that and and grow in that sort of relationship. So that has been like the biggest gift of writing.

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It's Thank you. >> Yeah. Thank you.