From “walking in the desert” to Escaping Flatland

Why and how Henrik Karlsson raised his ambition

Welcome to today’s installment of “Fantastic Builders and Where to Find Them.” This is likely going to be the last one for at least a few months while I really go head-down on my book. Meanwhile, you may be hearing from my husband and co-author Matt Bateman, to whom I’m basically handing the reins of The Psychology of Ambition during this time (believe me, he’s more than earned it).

Builder’s Spotlight: Henrik Karlsson

Principles on display: Raising your psychological ceiling, Your life as the yardstick, build yourself by building, Worrying on schedule

Image credit: https://x.com/phokarlsson/photo

When I stumbled into Escaping Flatland author

Henrik Karlsson

’s note about how he “decided to be more ambitious” with his writing and parenting—and his subsequent note thanking himself for that decision a year later—I had half a mind to just republish that original note verbatim, so emblematic is it of the kind of story I like to spotlight in this series. But then I realized it would be way more fun to get to talk to him about it, so I reached out for a conversation.

And what a conversation! Of all the many impressive people I’ve interviewed for this type of spotlight, Henrik left the most lasting epistemic imprint, so to speak: almost 2 weeks later, I can still hear certain fragments echoing in my head and shaping how I talk myself through writer’s block, how I think about life design for myself and my clients, what I give myself time to explore and digest (including of Henrik’s own essays!) even if I don’t yet have a tangible outcome in mind.

Below are some of those fragments, together with some exposition to put them in biographical and psychological context (with thanks to Matt for extracting an orderly narrative from the meandering chaos of the original transcript).

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Henrik’s narrative of his career as a writer is roughly as follows:

• A period of significant conventional success in his youth that he ultimately did not like

• “Seven years in a desert”, where he did miscellaneous things to make ends meet, and, most importantly, where he wrote strictly and only for himself

• The present, where he is making a living writing weird (and wonderful) essays

There are also as-yet unwritten future phases, in which he envisions being ever-weirder and more ambitious—books, large scale artistic collaborations, operas, films.

Seven years in a desert

Henrik had an unusual amount of early success as a young writer. But it was a success that that had hard limits. He increasingly felt himself encountering groupthink, and pushing into writing territory to which his audience and publishers reacted negatively. “It made it hard for me to stay connected to my curiosity,” he told me.

So he quit.

The story of my life is a lot of these very hard decisions. The decision of, like, I had a book deal, and I did a guest lecture at Harvard which was very alluring to my ego at the time. I had a very good career for a 23-year-old-poet, yeah? The decision was: blow that up because of principles. And doing that again and again.

For seven years, he did other things. He worked as a programmer, he ran an art gallery, he had children. But through it all, he was, privately and intentionally, developing himself as a writer.

“I got so sick of the publishing world, I thought I would never publish anything, so I was just writing for myself,” Henrik told me.

But it wasn’t out of general misanthropy; he was missing something.

He calls this seven-year period his “years in the desert.”

I think the years in the desert were super important, of just doing stuff for myself without compromise for seven years. You see that in the stories of a lot of people who do creative work, that they have years in the desert where they learn to trust themselves, to keep going to amuse themselves.

There is a very peculiar thing that happens when there is no expectation. You’re not even trying to get published. You're just writing things for yourself. And if you do that for years, the writing starts to change. You’re starting to develop some kind of taste that is totally unaffected by expectations of what is fundable—or anything at all.

And that also takes a long time. It’s running the kind of loss function of your mind until you figure out what it is you’re doing. I just needed a long time to figure things out, to unlearn all the things about how writing should look, and what is doable and not doable. And also building up skill, because—I was quite skilled, I could do the established things, but I had this feeling for another thing I wanted to do, but I didn't have the tools to do it.

It was a question of both: figuring out what is this other thing, and that I could only do by running hundreds and hundreds of experiments, and also gradually building up the tools to do that thing.

He had many interests in this time, most especially in education. The writing was coextensive with thinking about his parenting. In discussion with his wife, Johanna, he concluded from first principles that homeschooling was best for their children, but in Sweden, where he had lived his entire life, homeschooling is illegal. (He also had to deprogram himself from the cultural default he had internalized, that homeschooling is child abuse.) This thinking led him to another excruciatingly hard decision: that he and his family needed to leave Sweden and build an entirely new life on “a small island in the Baltic sea.”

Shortly thereafter, perhaps emboldened by the experiences of navigating and even thriving in the wake of these prior “hard decisions,” Henrik began to experiment with posting some of his writing online.

“There was also that longing for a community and belonging somewhere. But I thought that was totally impossible, because the weird combination of the things I wanted to do didn’t fit anywhere.”

At first he had “no signal whatsoever” from any audience except for his wife. And he even “deeply internalized that no one’s ever going to care about this. I had plenty of time to build up those habits of thought.”

When you’re doing something strange, there's no signal until there’s signal. If you're going into a pre-existing scene or pre-existing genre or something, there’s going to be signal. There’s going to be systems in place to move you along. But if you’re trying to stitch together like some kind of genre that will hold your voice, there will be no signal of whether you are making progress or not.

Finding signal

But Henrik did start to get glimmers of signal. His social graph was changing, and he was meeting people online who saw talent in Henrik and encouraged him to be vastly more ambitious. He started dipping his toes in the water more—he started a blog, he posted on LessWrong, he followed and engaged with interesting people on Reddit.

From there, I got in contact with some people who directed me to subreddits and so on. So I started to get some people who would see some potential in what I was doing and who were guiding me. They’re like, “Oh, you’re almost where you should be, but you should go over there.”

The internet proved connective. He found other young writers who gave him community, and others who effectively functioned as talent scouts for him.

A surprising number of these very unknown people became quite successful later. For example, Tracing Woodgrains. I think I met him very, very early on, when he was just writing comments on Reddit. There was him and there were a few others who were just totally unknown at the time, and have gone on and done things in parallel.

I remember at one point there was an early reader who I started talking to, and he explained to me how to write cold emails to people. And I was like, “Can you send me exactly what you wrote?” I used that to write to José Luis Ricón Fernández de la Puente, who writes Nintil, and he put one of my essays on his link list, and so on so. So there were people like José who helped to accelerate things, put me on the map a little bit.

It was still like a very slow first year there. But there was a process of some people coming in, and these people who have very exceptional taste and are extremely online. There were some people like that who I guess in some sense are scouting. These are VC type people. Some of them are actual VCs, but some of them are more like VCs for culture, but they are looking for new talent and giving them nudges and so on.

Importantly, the signal that he kept getting was: be weird. Be more yourself. Do more of the things that are off script.

I realized, I think that I’m good and disciplined enough that I can do this weird other thing and actually still pull it off. I’m getting some signal from that, from people I trust. I’m assuming they’re ahead of the curve. And if I just put in the hours and do the work, I could actually do that thing.

The belief that he could do it came partly from the fact that Henrik was getting signal from people he admired. And it also helped that the kind of people he admired and interacted with, the kind of people who responded to his writing, tended to be in the orbit of San Francisco culture. A core part of that culture: be more ambitious. Don’t underestimate yourself. You can do way more than you think you can.

And there’s a very different mentality than the small island life where I live. You get a lot of this very nice American thing where it’s like: you totally underestimate what you could do. To have people who have really good judgment tell you that—it’s just like, oh, yeah. Then I’m like, I trust your judgment more than mine.

Growth was slow in the first year. Henrik had 30 subscribers to his Substack when he wrote The Learning System. It didn’t explode, in Henrik’s words, but “that’s when the weird internet nerds found me—very high signal on the people who found me on that post.”

Henrik shifted his lifestyle to be able to write more. As he developed competencies and had material success in his non-writing work, he would “spend” that capital, both the literal monetary capital and his increased credibility with his employer, on working less and writing more. (More on that in Henrik’s essay: 6 lessons I learned working at an art gallery.)

What I did concretely was that I gradually lowered the amount of hours I worked. For the last two years, I’ve worked 20 hours a week whenever I wanted to write. That was my deal. Like, I traded all of my increased income toward just having more and more ridiculous demands on my employer. By being more agentic, I became so valuable to them that I could have these ridiculous demands, and that meant I could write.

Now—as of a few months ago, and two years after finding his first glimmer of signal—he can support himself and his family solely with his writing.

Ambition in all things

Since I’m writing a book on the psychology of ambition, I asked Henrik about whether his ambition in writing—his gradually changing belief that more no-compromise success was possible to him in writing—affected other areas of his life. His answer was an unambiguous “yes”.

Wait a minute, if my understanding of what is possible in writing and what I can do is so flawed, and it’s actually like 100x bigger what I can do, then that is probably true of parenting, too, and it’s probably true of all of the aspects of the things I care about.

Parenting was one obvious major domain. But it really was everything that mattered to him. “It was my exercise and my diet. And having a better diet makes me a better father. All these things are connected.”

I'm in this flywheel right now where I'm, like, getting better at things, and I'm using those resources to help me do better things. Concretely: I was able to stop working three months ago, and then I could channel that extra time into better diet and more exercise—so I can have more stamina writing. Hopefully that means I earn more money now. There’s this flywheel of getting more resources to spend more, be more ambitious around the things I care about.

It’s also notable that the form of Henrik’s ambitions is incredibly unique. He draws from the general sense of ambition in San Francisco while rejecting, at least for himself, its most common specific manifestations—e.g. growing his user base (audience) by 100x, or turning that into capital.

I have this sense in my head that I want to make something really big, much bigger than I had thought. Previously I thought that maybe I could one day publish a book, and now I’m thinking on a much grander scale than that.

That I got from the San Francisco people, in a way. But to me, it’s even more ambitious. I’m going to do that with both of my hands behind my back. I’m going to do it the hard way. I’m not going to compromise on the super weird things that I want to do, but I’m going to figure out the way of doing it at the scale that they’re talking about. To me, that’s, like, doubly ambitious.

Henrik also had unorthodox advice for people who haven’t yet built their own flywheel on their creative projects: consider separating into two phases the (1) tackling and refining your interior world and (2) development of competencies to deal with the external world.

You have to have two maps. You have to have a map of your interiority, and you have to have a map of the external world. And both of those are going to be terribly wrong by the time you’re 20, and I think trying to do both at the same time, for me, it’s just not going to work. I think it’s much easier, if you should just make a dividing line.

So—if you want to be more ambitious, right? So during the years in the desert, I was starting companies, and I’ve been running an art gallery, and I’ve been agentic there, and I’ve all the skills I’ve learned there. I was only trying to pay my bills, but I was gradually becoming better and better at doing that. I leveled up my skills at doing ambitious projects by understanding the external world kind of separately.

And [meanwhile] I was just trying to indulge myself and trying to figure out the internal map. Doing those two things separately, to sharpen both of those knives.

You need to have both an extremely deep connection to yourself and also be just like, “Okay, I've moved to Thailand, and I need to figure out the tax code, and I need to do it in two days, and I can do that, and I need to find the best helicopter pilot in Bangkok today.” You need to be able to do those things. But you can practice those things separately.

And whatever you learn there you can use over here. I was just reading the biography of Philip Glass, or his memoirs. He’s starting companies all the time when he’s young, like he’s starting a plumbing company, he’s starting a moving company, he’s doing taxi work. That is super useful for him when he’s making operas later.

Once, he becomes a famous composer, like he’s really good at negotiating, he owns all of the rights himself and runs his own publishing company. Because he’s already had four companies, and he knows how to negotiate. So once he gets to operas, he’s like, “Yeah, I’m not going to do the normal contracts, I want better pay and I keep the rights.” Because he’s done that at plumbing companies.

4 days to do whatever you want, 3 days to be “evil to yourself”

Towards the end of our conversation, I selfishly asked Henrik about his writing process.

How much of his writing makes it through to publication? He ballparked it at 10%. “90% of what I write, no one ever sees.” It’s mostly exploration, free-writing, pre-draft of any specific essay. Henrik still writes a great deal that is, in effect, for no one but himself. What about once he starts putting together material to form a specific essay? “Even when I get to a first draft, only like 50% of that gets published.”

Henrik divides his seven day week in half: 4 days and 3 days.

I do four days of the week which are total self-indulgence. My only job during those four days is to get up, get to work early in the morning, and to sit down and I ask myself: what is going on in my mind right now? What am I excited about? And my only job is to think about that. I do that for four days in a row.

Usually what happens at the end of that is that I have three half essays. That just totally unblocks me, because then I just be like, “Today, I just want to learn about grammar.” It’s just totally random things.

This is, not incidentally, his cure for writer’s block.

I try to not censor myself at all. The reason I get blocked is because I'm thinking, “Oh, this. The people aren’t going to like this a lot.” You have to separate those two things. So, yeah, I need to have a phase where I'm just totally crazy. I just trust my intuition 100% percent…

The other three days go towards sifting through the raw material generated during the first four days, and crafting essays designed to be read by an audience.

I have three days a week where I'm like, “Okay, I need to pay the bills. What in this mess could I present in a way that is meaningful to other people?” And then I take the thing that I can workshop into something that I can ship.

The fact that he gives the part of himself that is worried about money three days a week is also psychologically important to his creative process. Designating a stretch of time for that part of himself allows him to ignore it when he needs to be more freeform and exploratory.

The parts of me that are worried, they know that there will be three days where they are allowed to be totally evil toward me if they need to get work done. “Right now, I might just be following my curiosity, but you’re going to be allowed to be as evil toward yourself as you want you on Monday. There’s three days when you can just spank me all day long.” And then that part of me says, “Okay. I’ll sharpen my knives until Monday then.”

And there you have it, friends: a cutting metaphor for the very essence of the builder’s mindset, as applied to the intentional management of one’s own psychology. Thanks again, Henrik—my wanting-to-get-lost-in-cool-people’s-biographies part and my needing-to-meet-a-book-deadline part both really needed that.