A man sets out to draw the world. As the years go by, he peoples a space with images of provinces, kingdoms, mountains, bays, ships, islands, fishes, rooms, instruments, stars, horses, and individuals. A short time before he dies, he discovers that the patient labyrinth of lines traces the lineaments of his own face.
—Jorge Luis Borges, The Aleph and Other Stories
This is what writing is like to me. I’ll work on a topic until it bores me, then I pick something else, unrelated. I’m just piling random observations. But then, in December, I skim what I’ve published during the year and realize: the essays are shadows thrown at different angles from the same object.
Let me summarize what I wrote on Escaping Flatland in 2024, so we can glimpse the outline of that object. After the summary, I will share some reflections about how it was to run the blog and grow it into my full-time job, as it became on November 23. I wrote a summary like this last year, too, which you can read here.
These were the ten most popular1 essays in 2024
Everything that turned out well in my life followed the same design process
Almost everyone I've met would be well-served thinking more about what to focus on
The third chair ← My favorite
Also, in case you haven’t read the most popular posts from 2023, here are the top 5:
Dostoevsky as lover ← My favorite
What were the themes?
Self-cultivation
As a rule of thumb, I like to write about topics that have practical consequences in my life, or in the lives of people I care about. It helps me fool myself less: if I’m wrong, reality will hit me over my head as I practice the ideas I write about. (When I think about problems where I can’t affect the outcomes directly, such as politics, the lack of feedback makes it harder for me to calibrate my judgment. I don’t trust that I have the skill to say anything useful in such domains.)
This bias toward the local means my writing borders on self-help—and I’ve been confused by that since I don’t like self-help. First, because, again, I don’t trust myself to have much useful advice to give to people who live in contexts very different than mine. (I think, however, it is important to articulate different points of view and experiments in living so people can use that to see a larger slice of the possibility space). And, second, because the image of human flourishing that animates modern self-help feels off to me. It feels limited, self-centered, and unambitious. It doesn’t feel serious. And I like serious.
What I do feel aligned with is the classical ideal of self-cultivation, or bildung. It is more well-rounded and focused on a rich conception of human flourishing. I care deeply about agency and rationality, but I also care about the capacity for feeling, cultivated through encounters with art and by opening yourself up dialogically to Otherness. I like to push hard in both directions at the same time.
As I wrote in “Thoughts about agency,” I think that “talking about agency and introspection separately is misguided. People who emphasize how to get things done, and move faster, and reach higher levels of mastery—agency without introspection—tend to get pulled into fierce yet boring status competitions. People who emphasize introspection and emotions but without a problem-solving mentality tend to get stuck, and painfully aware of being stuck.”
And (as my wife Johanna pointed out to me) that is what I’ve been writing about: self-cultivation, not self-help. Nine of the posts in the top ten are about how to live a more full life, either by becoming more agentic, or more connected to a rich experience of reality. In particular the series that started with “Everything that turned out well in my life followed the same design pattern” and was followed by “Becoming perceptive” and “Reason is an underrated way to be authentic.”
Writing as a tool for thought and emotion
A useful consequence of writing seriously for 3.5 years is that I’ve become notably more intelligent. Not the underlying hardware, of course—that is slowly falling apart; I have, statistically speaking, lost about ~5 grams of brain mass since I started Escaping Flatland. But as OpenAI demonstrated this year: you can improve the performance of an LLM by letting it reflect in writing. The longer it writes, the smarter it gets. The same is true for me: by putting my thoughts on paper, so I can critique and rewrite them, I have put my thoughts in order.2 By burning more cycles on reviewing my thoughts, I can wring more out of my shrinking hardware. When I read what I wrote five years ago, and when I look at the decisions I made back then, I seem a standard deviation more stupid than now.
The most important essay I wrote about this was “How to think in writing.” There, I used Lakatos’s Proofs and Refutation to articulate a language that helped me write in a more structured and useful way. I read Lakatos in September 2023, after a few months of frustration at how uneven the thinking was in my essays. After about six months, when I had digested what Lakatos is saying, my thinking got more generative.
I also wrote an essay about how Plutarch and others used writing as a method to turn important ideas into an ethos, something engrained in our character. And I wrote about how structured writing helps you be more true to yourself in a holistic way.
I wish someone had taught me how to think in writing sooner! It is vastly underrated, and it is going to become even more valuable as AI systems gain more capacity and can do our bidding as long as we can explain ourselves, or ask good questions. Yet none of the writing instruction I’ve experienced or observed teaches you have to do it. (What resources or educators, teach this at an exceptional level?)
Relationships and parenting
A core, recurring pattern in my writing has been the idea that other people (and the rest of reality) are too complex to fit in our heads. We have to approach it in open dialogue. This topic was more in the backseat in 2024 compared to 2023 (when I was working on the “Looking for Alice” series (which I hope to wrap up next year!)). But I wrote two essays about relationships: “On feeling connected” and “Self-help for cocoons,” which, in many ways, marked a shift in the way I articulate this topic. The essays last year focused on how relationships and dialogicity help us grow and discover ourselves. But this felt instrumental in a way that didn’t feel true to what I wanted to say. The essays this year focused more on generosity and relationships as something valuable in itself. I prefer that framing.
I also really like “On limitations that hide in your blindspot” which is, among other things, a detailed portrait of how Johanna and I work together.
I also wrote two essays about parenting/education. The core thesis of my thinking on this subject is that to promote human flourishing and rapid skill acquisition, we need to foster cultures that effectively scaffold our learning. Pursuing this line of thinking, I wrote a piece about how Johanna and I (sometimes) read complex books (like Animal Farm) with our seven-year-old, Maud, so she can apprentice herself to our reading practices. I also wrote a comparative history of Jesuit education and Montessori, in an attempt to figure out how we can scale cultures that support agency and human flourishing beyond families and small groups.
Zooming out even more, it is clear that these topics are all the same:
I care about human flourishing;
I think that is largely about increasing your inner complexity so that you can see and interact with reality and other people more deeply; and
writing is a powerful tool in this pursuit.
What was it like to write Escaping Flatland in 2024?
Thank you for asking.
While 2023 was emotionally intense and bewildering—after the blog suddenly blew up in January following 18 months of obscurity—2024 felt more stable and productively boring.
After 2023, I felt somewhat confident that I could string 3,000 words together in a compelling way, without thinking too hard about grammar or style. (In 2022, I was still so unskilled at writing English that I used Google Translate for large chunks of the essays!) This meant I was, in 2024, freed up to think more about the ideas.
I set up a routine where I got up at 5 am every morning and wrote and studied for four hours before work. I was a bit tired of my blogger’s habit of reinventing ideas that have already been articulated more nuanced by others, so I worked hard to fill in the gaps in my intellectual education this year. I spent more time reading philosophy—doing serious reads of Aristotle and John Stuart Mill and superficial reads of Kant, Hume, Arendt, Kierkegaard, and Heidegger. (I’m currently doing late Wittgenstein if someone wants to share notes.) I also read my way through the collected works of several essayists: Samuel Johnson, Joseph Addison, Arthur Schopenhauer, and Ralph Waldo Emerson. It has been exciting to finally be good enough at English that I felt like I could read whatever I want, without getting a headache.
Funding
At the start of the year, I made an Excel model that projected that I could turn Escaping Flatland into my main income by summer.3 I wasn’t, however, sure if I wanted to do that.
I didn’t want to rush ahead into writing full-time if it meant that I risked putting myself in a position that would limit myself later. I’ve seen friends get caught in that trap and waste their talents. The important thing, to me, is the expected value of the full body of work I can produce over the next 50 years.
This was another reason why I spent so much time reading philosophy this year: it felt prudent to redirect more of my energy into doing things that will help me do good work long-term. Getting bogged down with Aristotle, I managed to flatten the growth curve enough that I missed the chance to become a full-time writer in July. But by November, the blog earned enough to cover rent and food, and since we had put aside previous earnings from the blog as savings, I quit my job on the 23rd.
Also, on the note of funding: I was on a podcast recently and was asked where I would get funding to do the kind of writing I do (before Substack), and my answer is, “I have no idea.” When I tried to pitch my type of essays to magazines, I got zero replies (though I’ve sold other kinds of writing), and I have never been able to convince grantmakers to fund me (though I’ve been successful in fundraising for others). So, Substack really changed the playing field for me.
Each new funding mechanism we invent allows us to uncover a new part of the possibility space. Magazines enable one kind of writing; grantmakers another; university tenure a third. None of them enabled what I do. But you did!
It will be interesting to see what kinds of writing Substack and other crowdfunding mechanisms can uncover if we run this experiment for a decade more. I expect that having more time and fewer intellectual constraints will compound in interesting ways (for those who manage to stay out of the numbers-go-up game), and I’m curious to see what comes out of it. I turned 35 this year, and I have no plan to ever retire, so we have—depending on how AI pans out—between . . . five and 500 years to go.
Finally, if the work I’ve done in 2024 has been meaningful to you, send some gratitude to the readers who fund it. It couldn’t be done without them.
I have unlocked two samples of paywalled essays (here and here) in case you are curious what they are like. If you want this to keep going, consider signing up.
As always, my main goal with the subscriptions is to fund public goods that are free for everyone, so if you want to read the paywalled essays but lack resources: just reply to this email. I can give discounts and free passes.
Thank you for coming along on the journey.
Henrik
I asked Claude to make the ranking based on a weighted sum of the number of likes, reads, and subscriptions generated by the essay. If you look at the ranking Substack does, it looks slightly different.
This point was inspired by a tweet by Nabeel Quereshi.
I get a lot of questions from people who wonder how I grow the blog, and honestly, you see it all. I write essays. I publish them. They get shared word of mouth. If you can get your writing in front of 20 people and they like it enough to tell their friends, you are set. The only conscious marketing I do is that 2-4 times per month I printscreen a quote from one of my older essay and put it on socials, so people discover the back catalogue. To be clear, I don’t think it is depraved to think about growth. Having reach brings new friends into your life, and sometimes you need scale to fund the work you want to do: let’s not be naive about that. But it is self-defeating to focus too much on marketing. The right proportion is probably to spend at least ~95 percent of your time getting better at the thing you actually care about.
Usually, I take at least a day or two to make purchasing decisions but I could not wait to pay for a full-year subscription to Escaping Flatland. The singularity and thoughtfulness of your writing are clear as daylight. Hoping 2025 is equally stable, productive and richer in depth.
Your thinking expressed through your writing on here is singular and has such clarity. Self-help is not a word that ever crossed my mind. I see the deep contemplative thought of a lover of wisdom, i.e., a philosopher, in the truest sense of the word. It seems as though you are living the life of a philosopher and sharing the riches with all of us. Thanks!