michael-dean-k/

I've been circling this question for a few months now. As a new parent I find little predictable focus time but a surge in unpredictable reading time. I have always been semi-intentional with what I read (essay books), but this seemed like a new opportunity. What started as a simple question spiraled into an unruly project: simple book searches grew into a multi-year 121-book personal reading syllabus along with two custom apps, one to plan my reading each month, and another to organize my Kindle highlights, letting me write response essays that get auto-published to my website. Underpinning all of this is the belief that the essays I write emerge from my life and library. You become your syllabus.

Naturally, a good portion of my syllabus contains classic essay books, from Montaigne backwards and forwards, back to some proto-essayists of antiquity, and forward to living writers. While I read non-fiction and history for ideas, fiction and poetry for feeling, I read essays for form, to understand the composition patterns I can use in my own writing and editing. The best way to do this is to teach. I suppose Essay Architecture as a whole is an act of teaching, but part of this new reading project is live teaching, through sessions on Zoom.

This post is a recap of a workshop I gave on Monday, June 15th (2026). It covers both the high-level questions of mine in terms of "how should an essay writer read?" but then zooms into the practical: how you can join us this summer to analytically read a classic essay every week.

I'll start by getting to the point: here's the syllabus. I imagine you've heard of many or most of these writers, but maybe you've never read their core essays, or maybe you have but never read them analytically to understand how they work. That's our goal.

1. David Foster Wallace, "Consider the Lobster" (June 22nd)
2. Leslie Jamison, "The Empathy Exams" (June 29th)
3. Ralph Waldo Emerson, "Self-Reliance" (July 6th)
4. Susan Sontag, "Notes on Camp" (July 13th)
5. Meghan O'Gieblyn, "Homeschool" (July 20th)
6. Michel de Montaigne, "To philosophize is to learn how to die" (July 27th)
7. Virginia Woolf, "Street Haunting" (August 3rd)
8. George Orwell, "Shooting an Elephant" (August 10th)
9. E.B. White, "Once More to the Lake" (August 17th)
10. Jo Anne Beard, "The Fourth State of Matter" (August 24th)
11. Joan Didion, "Goodbye To All That" (August 31st)
12. G.K. Chesterton, "On Lying in Bed" (September 8th, *Tuesday)

Before I get too theoretical on the philosophy or mechanics of reading, I'll share what we actually plan to do each week (on Mondays at 7pm ET). I run a community called Essay Club—which has 60 of us and has been running for 2.5 years now—and we kicked off 2026 with "monthly readings." Our members voted for this—among other features—but I originally set it up like a traditional book club with assigned readings (and nobody wants homework). We quickly realized that since essays are short, we could read them together on the call. We've run this session four times now, and I guess I would call it a "co-reading" experience, which feels sort of novel.

Here's how it works:

• I start with a 5-10 minute presentation where I give you context on the writer, and show you diagrams to illustrate some of patterns that the essay is representative of.
• We all read for 20-30 minutes in the same shared document and comment as we read. This let's you see how different people are all reacting to the same material. In case you can't make the session live, you'll still be able to read along through our shared doc.
• After that we jump into breakout rooms to talk it through, and then reconvene as a group.

Here's a diagram of Jo Anne Beard's "Fourth State of Matter," which we're reading in August.

I included the links above in case you want to read through these on your own, but Essay Club give you the accountability to actually stick with it. Reading ambitions are one of the easiest things to deprioritize when you get busy. Honestly, I'm partly doing this for myself; it forces me to show up every week with a firm understanding of how each essay is working (and it also helps me expand v2 of the textbook with a rich example bank). Most importantly, we aren't reading for reading's sake—which BTW is totally valid—but our main goal is to publish essays; we also have weekly feedback calls Friday at 3pm ET, and all aim to publish one piece at the edge of our ability by the 1st of each month.

If you're considering joining, check out the Essay Club website, and when you're ready you can sign up for an annual membership here, which is discounted at $450/yr through July 4th. The rest of this post is about how I'm personally thinking through my reading practice, covering everything from how to build a syllabus to how to read analytically and syntopically. I think it will give you helpful context whether you want to join Essay Club or want to build a syllabus of your own. (I actually recommend both: join a community to study essay form, but then build your own path that's more specific to what you're writing about).

An essay is made made of Material that orbits a Thesis. That material comes from your life and your library, so in some fundamental sense, you're only limited by how you live and what you read. I guess the real question is though, are you reading in a way so that it oozes into your writing?

There are all sorts of annoying reading maxims—on what you should read ("only read primary sources, never commentary or summaries"), how you should read ("never listen at 2x speed"), the volume of reading (X books per year)—that get disconnected from a reader's specific goal. All advice is contingent on your goal. A friend of mine reads for the purpose of doing something analog and relaxing before bed that isn't scrolling, and it would be dense of me to insist that he highlight excerpts and diagram the structure.

There are secondary reasons why I read of course—sometimes I'll binge Internet articles to makes sense of an event, or scour Wikipedia to become articulate in a sphere I feel like disoriented in—but the core reason I read is to evolve my writing. It's impossible to know exactly how reading changes you, but over time, in very noticeable ways, it all gets imperfectly synthesized through your writing. The inputs shape the outputs.

It's not about vanity book counts or the recital of facts at meetups, but slowly shaping the future corpus. I subconsciously absorb a writer's voice, consciously break down essays to see how they work, and save excerpts that becomes prompts for original essays. Here's an app I built to browse highlights; anything I write in the text field on the right gets auto-synced to my website.

This idea of "responding" to the authors I read was inspired by going deeper into Montaigne. If Montaigne were to be described for a single thing, it's that "he is the subject of his book," which was radical for the time; this gives the impression that all his ideas derive from his own life and mind. On the contrary, a typical essay of his might be peppered with 30 or so quotes from antiquity, featuring Plutarch, Seneca, Epicurus, Augustine, etc. He was a man of his library, and the genre of essay was forged by Montaigne's commonplace book, setting a very literal example for how your inputs shape your outputs.

A modern inspiration is Virginia Woolf, whose first two essay volumes were titled, "The Common Reader." These were responses and extensions of her reading diet, which was extremely polymathic in range. She was reading the Ancient Greeks (in Greek), the Romantic poets, Victorian biographies, Montaigne, and more, simultaneously, each shaping the topics of her writing, and the voice that would come to be her own.

It's been two years since I've committed to reading essay books, but I see this new syllabus project as a chance to widen the aperture. I've re-examined my physical library, found out lists, gathered recommendations, and found the inspirations of my inspirations. As the list grew, I split it into four genres, each of which I think will offer me something unique as an essay writer.

I'm reading History to build fuzzy maps across disciplines. It's about breadth. I'm looking for historians, curators, and biographers who can write literary textbooks (informative, but fun to read). This goes against the maxim of "read primary sources." If I were to read the western canon in full, it might take me 10 years and bottleneck my own publishing. Instead, I can read a chapter per month of Harold Bloom's The Western Canon, and slowly build a model of the history of literature. Who are the Bloom's in each domain? The goal is to slowly read many textbooks in parallel, each at a chapter per month. As an essay writer, I want to be able to quickly connect original ideas to historical ones. Sure, I could use AI to surface these connections, but I'd rather have concepts and figures available in the substrate of thought itself.

I'm reading Non-fiction to go deep on specific topics that I want to write essays on. That means this list should look different for each writer. I've gathered books across 5 categories: moral philosophy, perception, education, technology, and democracy. By having a list of many books around a single idea, I can read "syntopically" (more on that later). Realistically, among all my other reading, I can only read one of these per month.

I'm reading Fiction to understand narrative and feeling. Unlike the last two genres, this one is less about idea collection and more about experience the range of ways literature can move you, and understanding the art of the microcosm. I'm convinced that David Foster Wallace is such a good essayist because he was focused on fiction; this makes his essays very allegorical, where abstract concepts are baked into tangible characters, places, and situations. I intentionally don't have long books on my syllabus (ie: no Middlemarch, Moby Dick, or Infinite Jest), because again I can't read more than one of these per month. I limited my search to novels under 250 words, and to short story collections—the picks are evenly split between modern, classic, and science fiction.

I'm reading Essays to understand the form. It surprises me when I learn that aspiring essay writers on Substack don't read the history of the genre they write in. It's a 1:1 translation, and you not only get a complete literary experience in a single sitting, but you get to absorb pattens to bring into your own work, whether deliberately or through osmosis. Personally, I'm trying to read across time periods (thought not in any particular oder), along with specialized anthologies—including all 40 introductions to The Best American Essays series—and some works in popular literary theory, the main two being Essayists on the Essay and On Essays.

If you're interested in building out a syllabus, you need to factor in both what you're actually interested in, and what you have the bandwidth for. But at the very minimum, if you have a publishing cadence for essays, you should consider a reading cadence for classic essays too. I've done a daily classic per day, and it's very doable, but to fully digest and teach these, I'm slowing it down to one per week.

I'm going to read Reading Like a Writer, once I finish How to Read a Book, which is a funny title that gets laughs whenever I bring it up. The paradox is straightforward: if you can read, why read the book?; and if you can't read, how will you be able to read the book?"

This assumes reading is a binary thing—are you literate or not?—when really it's more like skiing or carpentry or writing, a skill with multiple levels of difficulty.

From Mortimer J. Adler and Charles Can Doren's "How to Read a Book":

"Given the same thing to read, one person reads it better than another, first, by reading it more actively, and second, by performing each of the acts more skillfully. These two things are related. Reading is a complex activity, just as writing is. It consists of a large number of separate acts, all of which must be performed in a good reading. The person who can perform more of them is better able to read."

The book breaks down four levels of reading, each one stacked atop the other.

• Elementary Reading is about basic comprehension: do you get it? It's very possible to read Heidegger or Dostoyevsky or any of the convoluted jargon-filled architecture theory textbook and walk away without a firm idea of what's been actually been said. Without an elementary understanding, it's hard to do anything at the higher levels.
• Inspectional Reading is not something I've done much of before recently building out my personal syllabus. It's not quite "speed reading," (at 2-3x speed) but flipping through an entire book in 30 minutes, scanning the table of contents and selectively reading parts—ie: the first paragraph of each chapter—to get a feel for the prose and ideas. This helps you decide if it's worth reading in full. Maybe you only need to read a specific chapter based on your writing goals. Those 30 minutes might save you 30 hours of toil. If you're building a long term reading plan, it becomes crucial.
• Analytical Reading is when you very slowly make sense of something you want to understand. You break the work down into chunks so you understand exactly how the pieces cohere into a larger argument.
• Syntopical Reading is when you read analytical across many books to triangulate ideas, find disagreements, and extend into your own original research and essay writing.

Analytical and syntopical reading is usually focused on the idea itself, but we can use these same concepts to deconstruct the composition of an essay. My pattern language is effectively a framework for syntopical reading. You use it across essays. Instead of inventing how to read analytical reading yourself, Essay Architecture gives you a tool of lenses to read through.

In our workshop we did an exercise where we all read two excerpts, by Woolf and Dillard, each about the total eclipse but fifty years apart. The excerpts were similar in many ways; they had a near identical frame—setting the when, the what, and the tone of the scene—the middle had an experience where they described the people around them, and each closed with imagery. But, they varied in how they used the Imagery (9.1) pattern. Woolf tapped into scale to induce awe, while Dillard tapped into alien and tribal metaphors to capture the fear and anticipation of the moment.

We won't just be reading 12 great essays analytically, we'll do so using a shared language so we can get very specific on the patterns that great writers use. Whether you use my pattern language, or create your own lenses for cross-essay reading, the point is that you can only really understand a concept when you see it across multiple works, taking on unique expressions based on different contexts. I write about this more in my essay How do you deconstruct prose?, on how we shouldn't just imitate syntax, rather we need to know the specific way to use a specific pattern to achieve a specific effect.

So far we talked about the importance of building a syllabus (inspectional reading) and then how to read (analytical/inspectional). Now I want to talk about why I picked these specific 12 essays. In the future, I would love Essay Architecture to help generate a 1-of-1 custom syllabus for you. After uploading your own work, and analyzing the patterns across it, my software could make you a personal reading list, including essays that both share your strengths, yet show your weaknesses elevated to their peak, giving you a vision into the writer you could become. That will take some time! But for now, the goal is to make a general introduction, a good starting point for someone who hasn't start reading the classic essays yet. What are the heuristics to make this list?

I decided that we should focus on many authors (one per week) with the practical goal of learning patterns we can bring into our own work. There might be a future where we do single author deep dives, or historical assays into more obscure writers, but for now, I want to introduce you to a range of writers. I also decided it would be most accessible to focus on new essays, since they're more parallel to what we're all publishing today. That said, I did want to include some older writers that have more challenging, relatively archaic prose, because they show the power of a medium before text was neutered and optimized for mass readability—I'll do my best to provide a frame and the right translations so you have all the context you need.

I started with 12 writers that I've been reading and am starting to know decently well. Across six of the more prominent anthologies and theory books, each of these essayists are featured at least twice, meaning there's an objective anchor to validate the importance of these figures.

I also made sure there was a good amount of "opponent processing" in my selections, so that you would see the largest range of possibilities:

• Each writer has an "opposite." For example Emerson and Montaigne represent the dichotomy of the skeptic vs. the sermon. Didion and Sontag represent the journalist vs. the academic. Orwell and White represent the aggressive vs. the sensitive.
• Within these twelve, each could also be a representative of a distinct "mode" of writing; where patterns are about the objective patterns the reader experiences, think of mode as the internal sensibility that drives creation. I'm defining these modes as inquiry (getting to the bottom of a question) vs. interiority (rendering their consciousness), and expression (articulating through poetic words) vs. critique (engaging with their culture).
• And finally, each selected essay will be a lens to properly understand a particular pattern—DFW for microcosm, Jamison for perspective, Emerson for word choice, Sontag for references, etc. I think it will be easier to remember these patterns when they're personified through people and specific essays.

Over time, we'll get to see very different articulations of the same pattern. A personal experience can be contained within a single place ("a day at the fair" essay), or it can be an A>B journey. It can be an extraordinary event, the kind of thing that happens once in your life, or maybe your essay just has a spattering of humble anecdotes. It can be an experience you purposely throw yourself into like a journlist, or it can be a recollection of your childhood, the things that inevitably happened to you.

If you want to work through these essays intentionally and with a group, that's what Essay Club is for.

We don't just read together, we write and publish. Our readings are meant to augment our own original writings. The group runs on a simple monthly template. At the beginning of each month we set our goals, and we're all unified with a shared publishing deadline: the 1st of each month (marked by a "publish party" where we read and comment on each other's work).

Every Friday at 3pm ET we have a working session, where you can exchange feedback (1:1 in a breakout room), talk through your ideas, or simple block out the time to write.

Then on Mondays at 7pm ET we have our reading sessions. In July for example, you'll read Emerson, Sontag, O'Gieblyn, and Montaigne, each of who might teach you a pattern to integrate into your own work.

If you can't make the live calls, there's a lot happening async too. For one, all our live readings happen in a shared document, which you'll have access to, meaning you can read it on your own time while still seeing how everyone reacted in the moment. Additionally, we have a forum where you can upload drafts for async feedback exchanges. And since the club is so anchored in Essay Architecture, every gets the textbook for free, along with free uploads to the Essay Architecture software, which analyzes your essay along the 27 patterns to help you identify areas to work on.

I've been running Essay Club for 30 months now. The goal is to sustain this for the long haul, to create a place where I can be independent writer, teacher, and scholar of the essay; I say this to say that I'm in there writing with you, and I'm invested in evolving the club because it's integral to my own practice. Around every 6 months we add a new feature, and this new weekly reading curriculum is just the latest. More to come. It's structured as an annual membership at $600/year, but I'm offering it at $450/year through July 4th to promote the launch of our summer syllabus.

However you move forward, I hope this got you thinking about how you read. I recommend you take the time to think through the writer you want to become, and shape your own syllabus accordingly (in addition to joining our essay reading list). Try reading less, but reading slower and more deliberately, looking for patterns across works. And finally, Essay Club gives you the structure to do this every week, so even if this whole idea of building your own syllabus sounds intimidating, all you have to do is show up and read.

Essay Club website | Sign up for an annual membership here

Appreciate you bringing this up in the Q&A [X], and thanks for starting this thread [Y]. This taps into some themes I’ve been thinking and writing on, so I’ll use this as an opportunity to further unpack it.

There’s a lot to say on making “art”—or any individual pursuit—through a collective crisis where individual effort feels meaningless. Fortunately we aren't alone and have a whole history of crises, so there’s probably a lot to learn in how people responded (this is one impetus for me trying to read more, especially in political philosophy).

I imagine there is a spectrum here, ranging from “focus on yourself” to “society-scale action.” I think if you focus too much on either side, you risk deflation. Purely selfish pursuits, however noble, can easily have the narrative behind them ripped out if the bigger picture hits a certain intensity. And purely collective actions, like protesting, also lose momentum when you realize a million people together have no leverage, and you’ve contributed much of your time to a cause instead on what you’re uniquely qualified to do, which is equally demoralizing. So the answer I think is to run both in parallel.

I’ve come across a Ghandian POV from some writers I admire, which is essentially, “be the change you want to see in the world.” While I resonate with this from multiple levels—for example, on taking responsibility for everything, and being very diligent in your own values instead of worrying about or judging others for their lack—I also think it can be a bit myopic. Cultural progress is possible, and it exists at a scale far bigger than any individual. Meaning, a lot of values and culture stem not form charismatic and well-principled individuals, but from the larger architectures we’re all entangled in. Those systems are designed, and history seems to oscillate between periods where systems are designed to withhold/protect virtues or designed to expand/preserve power.

The bigger question for me: how can any regular person be part of systemic change? It comes down to a leverage thing. I don’t currently operate at a level where I have any impact on government, culture, economics, education, and while it’s nice to hope, I don’t have delusion to think I’ll ever have civilizational leverage. I think few people in history ever do. Even Trump’s leverage is debatable! I don’t mean to get into politics here, but I will link out to a post I wrote, “What we have is worse than a king.” The main idea is that Trump is not the root of any of our problems, he’s more so the most visible manifestations of an OS that has been anti-democratic and anti-constitutional for many decades now, maybe even a century.

So within the sphere of “systemic action,” there’s another spectrum of what a person can do, ranging from theoretical to practical. Again I think it’s worth pursuing both. On the theoretical side, I personally find it fun to engage with systems designs at abstract levels that are far beyond my control. ie: I thought Bernie’s AI sovereign wealth fund was a malformed idea, so I did my best to understand it and propose an alternative. This is arguably big a waste of time, but I think there’s value in learning to think as a systems architect, and to imagine new kinds of civic technology. On the practical side, there’s Essay Club, which is something whose existence and flourishing is entirely dependent on me, but the impact is limited. 

A lot of modern forms of activism are neither theoretically interesting or practical. Instead of performing dissent (via protests or culture wars), I think we need to enact new types of techno-activism that are now possible with AI.

Over time, the practical thing may grow to a point where the theoretical systems architecture skill comes in handy. Maybe in twenty years Essay Architecture is a software-backed curriculum that runs across a few hundred/thousand micro-schools. Or maybe it doesn’t, and Essay Club only grows to WOP-scale, letting me focus on writing and teaching, while giving meaning to a small group of people, which is fulfilling and worthwhile in its own right. Twenty years is far off, and it’s been almost 20 years since I started architecture/writing in general. So that’s like a 40-year lag between intention and implementation, effectively, an entire life.

And so as urgent as everything feels I think patience is the key. There’s probably something to zooming out to the scale of your life, modeling where you think society might be in the 2040s, and slowly steering the boat in that direction. By focusing on individual pursuits, practical projects, and theoretical systems, for decades each, there’s a chance that at least 2 of those lanes might fuse together in a meaningful way.

Anyway, I enjoyed the occasion to use this as a prompt for my morning essay! Hope it’s vaguely related to and useful to your own streams of thought, and open to feedback and pushback. On a meta-level, I think there’s something neat in using emails/letters—which each have a specific person or two at the receiving end—as a way to start drafting essays. I already have this as a post on my website, and similarly, both of your notes could be public too.

Someone dies in my town every day. I know this because I signed up for the newsletter of a nearby funeral home that I often pass by. It's strange to see an institute of death using a Squarespace template with stock photography of the Manhattan skyline and Central Park with animated text saying "Here for You in Your Time of Need," and I did not expect an email input field with the title "Obituary Notifications." Now I get them every morning at 4-8 AM. Half of them are blank—"An obituary is not available at this time for..."—and the other half are templated (including details like day of death, surviving kin, and other biographical details like hometown, college, hobbies, defining attributes). One that stands out, however, is for a forty-year pioneer of the KORG synthesizer.

A long human life get compressed to 350 words of text—shorter than the length of this post—sometimes well-written, sometimes templated, sometimes AI-generated, and sometimes "an obituary is not available at this time." As a writer, it would be snobbish for me to judge the cliches, misuages and inauthenticity of the everyday obituaries. Those are for the families and friends, not objects of literary scrutiny. The actual value of getting these from strangers each morning is to remind myself of my eventual destination. I imagine a scoff, "but you won't be alive to care about your own obituary!" But isn't that a solipsistic view? In all my memories of wakes and funerals, I notice in myself a sudden post-humous interest to make sense of the person in full, outside the illusion of time, perhaps triggered by a 70-year old photo of them youthfully playing guitar, where I realize I've never quite seen them beyond their elderly form. If they had writing to read, I'd read it all.

And so recently I came across the obituary of Ned Stuckey-French, a fellow essay evangelist from a generation before me. He died in 2019. He contributed to both of the recent US/UK volumes on literary theory of the essays (Essayists on the Essay and On Essays). I only knew he died because the On Essays table of contents has a cross next to his name. While I have some major disagreements with the thesis that both books converge on, I got an email from Academia.edu the other day, showing a paper Ned wrote; he was able to synthesize and clarify everything, and suddenly I had the urge to dive into his work. Upon searching him, his obituary is the 2nd result. It was 242 words, but I was thrilled to find a link to his personal website, a portal to understand the man in full.

A prolific writer, Ned concentrated his professional efforts on personal essays and championed the essay as an art form. His efforts were instrumental in saving the University of Missouri Press. Many of Ned's works may be viewed at http://nedstuckeyfrench.com/.

I'm met with a dark blue screen and white banner, saying "This domain is registered at Dynadot.com. Website coming soon." A personal website is a fragile thing. Unlike a platform, where your page stays up as long as the company is solvent, a self-maintained site is virtually bound to disappear if the living author doesn't put together some kind of succession plan. I found his wife's website too, untouched for 12 years, but still up; I imagine myself emailing her and offering help to revive Ned's site, before remembering that I know almost nothing about Ned or their relationship, and it would probably be an intrusion.

This all gets me thinking: how do I set up a website to last a hundred years? Wordpress offers 100-year hosting, and it costs $38,000 ($31/month x 1,200, all upfront). Matt Mullenweg, the co-founder, admitted six months into the project that they've had zero takers. Another alternative is "Posthaven," which promises permanent hosting as long as you pay for one year ($60). Sam Altman uses this. The downside is that you have to use their platform, templates, CMS, and I'm now very much on a "own your data" quest.

A few options:

• Since my website is hosted on Github, I could make that public. Even if the domain gets lost, you can still access the whole vault, and it would be trivial to repoint the entire site on to a different host.
• Quarterly saves to Wayback Machine.
• Compress my whole vault into a single PDF or HTML file, a single thing that is shareable and savable.
• Print my vault into a book/ebook (and register it with the Library of Congress)

For all I know, Ned had his own measures, and I just can't find them. The domain functions as the centralized place, aggregating all the essays and all the links out, but it's the most fragile part of the stack. For now, I can buy up to 10 years in advance on Squarespace. Beyond that, I would need to rope someone into the possibly pathetic-sounding enterprise of a "blog succession plan," because no one really cares about your writing as much as you do, at least while you're alive.

However, reading about christopher.org gives me hope (a story on how friends preserved a dead friend's website). It also clarifies that while 100-YR hosting is $38,000, a 100-YR domain is only $2,000. This points to a paradigm where the bookends of the website stack are solid:

1. The vault of all your files and code (the origin) are Git-hub hosted. As long as there is a singular public repo of everything, it can be shared, downloaded, stored locally, and re-uploaded somewhere else if need be. Considering Github is critical for web infrastructure, it will likely be around for decades, making it a good home for your files;
2. The domain (the destination) can be paid for 100 years in advance, leaving no financial stress on the inheritor;
3. The hosting platform (the middle) can be swappable. The Github vault can be easily connected to one of several free hosting sites. Currently I'm on a paid plan with Netlify, but maybe that's a liability. I need to find one that's free and likely to last, because this is the only fragile link in the system. The guaranteed survival here depends on a document that specifies: (a) the credentials for the 100-YR domain, (b) some loose heuristics on how to go about transitioning to a different hosting platform, and (c) a note of gratitude with some perspective on why it's worth maintaining.

I imagine it's strange to watch someone think through a blog succession plan in far more detail than an audience growth plan. I'm only in my mid-thirties, and it's not like I have any terminal illnesses that I know of, so why am I writing for unborn audiences instead of living ones? Having a kid, I'm sure, has something to do with it. I have a recent essay called "we all inevitably becomes tales," and as I reflect more on deep time, and as I try to visualize my 5-month old daughter as a grandmother, I see more often through a perspective where I no longer exist in the throne of my own consciousness, and instead exist as words being rendered into someone else's. I suppose it brings me a subtle anxiety knowing that, if I were to spontaneously die on my walk today from some teenager barreling into me with their motorcycle as they lose control during a one-handed wheelie down the main boulevard, much of my writing would die with me, and weirdly the real tragedy at the scale beyond my life is that even though the death of my mind, body, and soul is inevitable, the death of my writing is not.

Join Essay Club and meet with us on Mondays at 7pm ET to read and talk about these classics:

• David Foster Wallace, "Consider the Lobster" (June 22nd)
• Leslie Jamison, "The Empathy Exams" (June 29th)
• Ralph Waldo Emerson, "Self-Reliance" (July 6th)
• Susan Sontag, "Notes on Camp" (July 13th)
• Meghan O'Gieblyn, "Homeschool" (July 20th)
• Michel de Montaigne, "To philosophize is to learn how to die" (July 27th)
• Virginia Woolf, "Street Haunting" (August 3rd)
• George Orwell, "Shooting an Elephant" (August 10th)
• E.B. White, "Once More to the Lake" (August 17th)
• Jo Anne Beard, "The Fourth State of Matter" (August 24th)
• Joan Didion, "Goodbye To All That" (August 31st)
• G.K. Chesterton, "On Lying in Bed" (September 8th, *Tuesday)

Here are three maxims that shaped why and how I built the syllabus below:

• You become your syllabus. An essay writer should read differently from a general reader. Every inspiring quote becomes a seed that could launch an essay, or at least be woven into one. This syllabus is an attempt to shape the books that I want to shape me. I've organized the book into four genres (and each has subdomains): I read Essays to understand the form, since that's the same form I'm creating with; I read History so that a literary curator can help me build maps of people and concepts across different disciplines; I read Non-Fiction to go deep on the ideas I want to write more essays on; and I read Fiction to understand the different emotions and moods that words can render (also, fiction teaches allegory, which is about embedding concepts into tangible symbols; I imagine DFW is the essay writer he is because he was primarily a fiction writer.)

• Converse with the authors. A Montaigne essay is often filled with dozens of quotes. His essays likely originate from his commonplace book, his collected quotes from Seneca, Plutarch, Epicurius, Augustine, etc. I've been reading on Kindle for two reasons: (1) because when my daughter is sleeping on me, it's much easier to read one-handed; (2) all my highlights get synced form Kindle to Readwise to my own app. This makes it easy to resurface highlights and write short, original essays in response to them. They're all gathered on my website. This helps enforce the idea that it's not about having read the book, but about using the book as a way to inspire original writing. And of course, by writing about and in response to books, I remember them much better.

• Non-linear reading. Since the end goal is to read to produce writing, I don't necessarily need to finish all 121 books here or go in any particular order. For many of the books in Histories, I'm reading a chapter per month over 2 years. For some works in Non-Fiction, I've done an inspectional read and have selected just a handful of chapters that I think are most relevant to me. Generally, there are many textbooks running in parallel, and then each month includes one work each from Essays, Non-Fiction, and Fiction. I built a "syllabuilder app" to plot out what was possible to read in a given month (which is why I track page numbers below). This month I have 19 books I'm reading simultaneously. In any given day I might jump around 3-4 books. Overall it's less than 1,200 pages per month, or 40 per day, which matches a graduate level syllabus (probably 60-90 minutes per day of reading). I'd say this is like a reading list for a Master of Liberal Arts with a focus on the essay, moral philosophy, and civilizational thinking. This is roughly 6 semesters worth of reading, so it can be done in 2-3 years. The goal is to "finish" this by the 2028 election (acknowledging that I have permission to stop any book if it's not fruitful).

I. ESSAYS

1a) Essay Books

• 1588, Michael de Montaigne, Essais (2 units, Vol I-II=228p, Vol III=195p) $11
• 1625, Francis Bacon, The Essays (155p) $10
• 1760, Samuel Johnson, Selected Essays (The Rambler = 250p) $13
• 1764, Voltaire, Philosophical Dictionary (16 selected essays = 88p) $13
• 1844, Ralph Waldo Emerson, Essays¹ $15
• 1850, Ralph Waldo Emerson, Representative Men (150p) $1
• 1936, G.K. Chesterton, In Defense of Sanity (20 selected essays = 114p) $2
• 1941, Virginia Woolf, The Complete Works (25 selected essays = 210p) $2
• 1952, George Orwell, A Collection of Essays (selected 147p) $9
• 1966, Susan Sontag, Against Interpretation (selected 202p) $13
• 1968, Joan Didion, Slouching Towards Bethlehem (242p) $11
• 1982, Annie Dillard, Teaching a Stone to Talk (selected 90p) $10
• 1997, David Foster Wallace, A Supposedly Fun Thing I'll Never Do Again² $11
• 2005, David Foster Wallace, Consider the Lobster (selected 180p) $11
• 2007, David Foster Wallace, Both Flesh and Not (selected 230p) $11
• 2018, Meghan O'Gieblyn, Interior States (225p) $9

1b) Anthologies & Criticism

• Karshan & Murphy, On Essays 2020, $27
• Carl H. Klaus, Essayists on the Essay, 2012 ³
• Robert Atwan, Introductions to the Best American Essays 1986-2026
• Phillip Lopate, The Art of the Personal Essay, 1994 ⁴
• Phillip Lopate, The Glorious American Essay, 2020, 884p $8
• Phillip Lopate, The Contemporary American Essay 2021, (613p) $10
• Brian Dillon: Essayism: On Forms, Feeling, and Nonfiction, 2018 (155p) $10

II. HISTORIES

2a) Humanities

• Literature: Harold Bloom, The Western Canon (1994) $11
• Architecture: Kenneth Frampton, Modern Architecture: A Critical History (1980) $15
• Arts: Kenneth Clark, Civilization (1969) $3
• Design, Christopher Alexander, A Pattern Language (1971) $34
• Poetry: William Spengemann, Nineteenth Century American Poetry (1996) $9
• Antiquity: Arthur Hugh Clough, Plutarch's Lives (Volumes I and II) (2018) $10
• Science: Bill Bryson, A Short History of Nearly Everything (2003) $11
• Cosmology: Brian Greene, The Hidden Reality (2011) $5

2b) Civics

• Politics: Alan Ryan, On Politics (2012) $15
• History: William & Ariel Durant, Lessons of History (1968) $14
• Philosophy I: Anthony Kenny, A New History of Western Philosophy (2010) $13
• Philosophy II: Bertrand Russell, History of Western Philosophy (1945) $8
• Media: Denis D. Cali, Mapping Media Ecology (2017) $47
• Technology: Walter Isaacson, The Innovators (2014) $17

2c) Spirit

• Psychology: Morton Hunt, The Story of Psychology (1993) $12
• Religion: Huston Smith, The World's Religions (1958) $12
• Christianity: Fifth Edition, The New Oxford Annotated Bible (2018) $16
• Orthodoxy: Kalliostes Ware, The Orthodox Way (1979) $10
• Mythology: Mircea Eliade, Patterns of Comparative Religion (1949) $17
• Esoterica: Manly P. Hall, The Secret Teachings of All Ages (1928) $1
• Hermeticism: Franz Bardon, Initiation into Hermetics (1956) $20
• Death: The Oxford Book of Death (1983) PDF

III. NON-FICTION

3a) Virtues and Ethics

• 350 BC, Terence Irwin, Aristotle: Nichomachean Ethics (1947)⁵$14
• 180, Marcus Auerelius, Meditations (221p) $1
• 1882, Friedrich Nietzche, The Gay Science (selections = 100p) $8
• 1941, Stefan Zweig, Montaigne, 1941 (162 pages) $12
• 1947, Simon de Beauviar, The Ethics of Ambiguity, 1947 (160p) $10
• 1979,Thomas Nagel, Mortal Questions (226p) $18
• 1981, Alasdair MacIntyre, After Virtue: A Study in Moral Theory, (1981) ⁶ $28
• 1994, Carl Sagan, Pale Blue Dot: A Vision of the Human Future in Space, 1994 ⁷ $12
• 1997, Isiaah Berlin, The Proper Study of Mankind, 1997 (233 pages)⁸ $15
• 2008, Paul Tillich, The Courage To Be, 2008 (207p) $10
• 2009, Bernard Reginster, The Affirmation of Life: Nietzsche..., 2009 (250p) $17
• 2023, Ursula Goodenough, The Sacred Depths of Nature, (224p) $20

3b) Psyche and Attention

• 1662, Blaise Pascal, Pensees (Part One, The Wager, The Mystery of Jesus = 135p ) $10
• 1861, Henry David Thoreau, Thoreau, The Journals, 1837-1861, 2001 ⁹ $15
• 1935, Fernando Pessoa, The Book of Disquiet, 2002 (excerpts at 250p) $13
• 1961, Carl Jung, The Quotable Jung, 2015 (317p) $10
• 1970, Iris Murdoch, The Sovereignty of Good (1970), (106p) $15
• 1997, John O'Donohue, Anam Cara (204p) $15
• 1997, Alain de Botton, How Proust Can Change Your Life (208p) $9
• 2007, Douglas R. Hofstadter, I Am a Strange Loop, 2007 (Ch 1-8 and 13-19 = 240p) $16
• 2019, Ian McGilchrist, The Master and His Emissary, 2019 ¹⁰ $15

3c) Craft and Education

• 1908, Rainer Maria Rilke, Letters to a Young Poet , 2011 (100p) $11
• 1920, Sertillanges, The Intellectual Life: Its Spirit, Conditions, Methods 1921 (264p) $2
• 1938, John Dewey, Experience and Education, 2007 (90p) $11
• 1940, Mortimer J. Adler, How to Read a Book, 2011 (Skip part 3 = 221p) $17
• 1948, Josef Pieper, Leisure: The Basis of Culture, 1948 (~130 pp) $15
• 1965, John McPhee, A Sense of Who You Are, 1965 (143p) $12
• 1987, Allan Bloom, The Closing of the American Mind 1987 (selections = 88p) $15
• 2009, Robert M. Pirsig, Zen and the Art of Motorcycle Maintenance (2009)¹¹ $16
• 2009, Mark McGurl, The Program Era (Part I = 182p) $15
• 2015, Stanley and Lehman, Why Greatness Cannot Be Planned, 2015 (141p) $18
• 2016, Ericsson & Pool, Peak: Secrets from the New Science of Expertise, 2016 (0,1,3,4,5,7 = 184p)

3d) Politics & Economics

• 375 BC, Plato / Allan Bloom The Republic, 301p
• 1840, Alexis de Tocqueville, Democracy in America, $18
• 1948, F.A. Hayek, Individualism and Economic Order (first five chapters =  107p) $23
• 1967, Guy Debord, Society of the Spectacle, 1967 (132p) $3
• 1988, Joseph A. Tainter, The Collapse of Complex Societies, 1990 (246p) $44
• 1996, Rodney Stark, The Rise of Christianity, 2020 (255p) $10
• 1998, James C. Scott, Seeing Like a State (Ch 3,4,9 = 110p) $10
• 2009, Mark Fisher, Capitalist Realism, 2009 (120p) $12
• 2014, Martin Gurri, The Revolt of the Public, 2018 (Ch 3-8, 11 = 280p) $10
• 2014, The Accelerationist Reader, 2019, (selected essays = 150p) $19
• 2019, Matt Stoller, Goliath: The 100-Year War Between ... (2019)¹² $10
• 2023, Peter Turchin, End Times: Elites, Counter-Elites, & ..., 2023¹³ $10
• 2026, Quinn Slobodian, Muskism, 2026 (170p) $15

3e) Technology and AI

• 1934, Lewis Mumford, Technics and Civilization, PDF ¹⁴
• 1993, Neil Postman, Technopoly: The Surrender of Culture to Technology, $9
• 1999, Steward Brand, The Clock of the Long Now: Time and Responsibility, $10
• 2017, Max Tegmark, Life 3.0: Being Human in the Age of AI, $15 ¹⁵
• 2020, Toby Ord, The Precipice: Existential Risk and the Future of Humanity, $15 ¹⁶
• 2021, Meghan O'Gieblyn, God, Human, Animal, Machine (273p) $10
• 2024, Nick Bostrom, Deep Utopia: Life and Meaning in a Solved World, $15 ¹⁷

IV) FICTION

4a) Modern Fiction

• 1914, James Joyce, Dubliners¹⁸ $1
• 1915, Franz Kafka, The Metamorphosis, 1915 (75p) $9
• 1922, Herman Hesse, Siddhartha, 1922 (150p) $4
• 1925, Virginia Woolf, Mrs. Dalloway, 1925 (190p) $7
• 1938, Ernest Hemingway, The Complete Short Stories of Ernest Hemingway ¹⁹ $17
• 1958, Jack Kerouac, The Subterraneans, 1958 (110p) $10
• 1965, John Williams, Stoner, 2010 (277p) $10
• 1965, Katherine Anne Porter, The Collected Stories of Katherine Anne Porter, 1965 ²⁰
• 2001, Alice Munro, Hateship, Friendship, Courtship, Loveship, Marriage, 2001 ²¹
• 2009, Lydia Davis, The Collected Stories of Lydia Davis²² $15
• 2020, Solvej Balle, On the Calculation of Volume Part I, 2024 (160p) $10

4b) Classic Fiction

• 1744, Johann Goethe, The Sorrows of Young Werther, 1744 (130p) $3
• 1759, Samuel Johnson, The History of Rasselas, Prince of Abissinia, 1759 (120p) $5
• 1843 Charles Dickens, A Christmas Carol and Other Christmas Books, 1843 (90p) $6
• 1866, Leo Tolstoy, The Death of Ivan Illyich and Other Stories, 1866²³ $14
• 1877, Fyodor Dostoyevsky, The Best Short Stories of Fyodor Dostoevsky²⁴ $7
• 1890, Oscar Wilde, The Picture of Dorian Gray, 1890 (190p) $6
• 1899, Anton Pavlovich Chekhov, Selected Stories of Anton Chekhov²⁵ $12

4c) Science Fiction

• 1968, Kurt Vonnegut, Welcome to the Monkey House ²⁶ $6
• 1944, Jorge Borges, Ficciones²⁷ $8
• 1995, Octavia Butler, Bloodchild and Other Stories ²⁸ $9
• 2002, Ted Chiang, Stories of Your Life ²⁹ $9
• 2012, Ursula Le Guin, The Unreal and the Real, ³⁰ $10
• 2014, Margarett Atwood, Stone Mattress ³¹ $9

250 years ago lived an arbitrary man who I can call my ancestor. He was one of 256 of my great great great great great great grandparents. It is unlikely that any of them ever met, but there was very possibly a moment where two strangers crossed in a street, or shared a boat unknowingly, or exchanged pleasantries in insignificant and instantly forgettable ways, not knowing their great great grandchildren would give birth to my great great grandparents. My existence depended on the whims of those 256 people—their triumphs and disappointments, decision and indecision, love and otherwise. Compelled by nature or eros or God to breed with a specific person at a specific time, they continued casting down the great chain of being.

How alike am I to any one of them? If my parents can each claim 50% of my traits, then my great^6 grandparents each only claim 0.39%.

In one sense, I bear almost no resemblance to any of them. Maybe, in an Empedoclean sense, you might see my nose roaming around a town square, or my hairy feet wading through a field. Any one ancestor might feel no affinity towards me; if I knocked on their door after accidental time travel and needed a place to stay, they might just past off the responsibility to one of my other 255 ancestors. Over enough centuries, your descendants balloon past a scale you can adequately care for. My wife, for example, is part of an old royal Welsh family that goes back to the 1250s. She even has a family ring. Yet, by the theoretical logic above, she is one of millions with a claim to the throne.

In another sense, a more romantic sense, my 256 great^6 grandparents represent a still very small sliver of the human population. 0.000000256%. If any of them had any resemblances to me, physical or mental, I’d like to know. Of course, our consciousnesses would be quite different, for identity is forged from circumstance, but I don’t doubt that I would find uncanny resemblances. When I hear the lore of my great^2 grandparent, a peasant on a dry, rustic, Greek Island, and how he was able to harvest and sell rain water to get rich, I wonder if his entrepreneurship speaks to my own entrepreneurship. It is quite vague to trace influence back even 1-2 generations, let alone 8 or more, but nonetheless, the actions of those people did eventually lead to me, and there are all sorts of ways their myths and interiors might shed context into my own circumstance, at least symbolically.

Unfortunately though, none of my 256 were writers. At least, not that I know of. Some may have written journals, or written for administrative reasons, but as far as I know, none left a body of work that was meant to be cast and continued through time. One grandfather did have three chapters of an abandoned novel on a 1980s hard drive that my father was able to recover. My other grandfather is uneducated, barely literate, and only writes English in capital letters. Now that I think of it, it’s probable that +95% of my great^6 grandparents could not read or write. Mass literacy wasn’t realized until the early 20th century.

Even though we shifted from oral to written history in Ancient Greece, most family history today is only passed down through spoken stories. They’re etched into memory and unreliably translated down the chain. I can barely trust the stories I pull from my head, planted decades ago, either misdelivered or misremembered. Was she really a psychic midwife that predicted winning horse numbers in her dreams making her son rich until a black hand cut her off? Did he really drive Nixon in a cab?

It would be strange for a society to sleepwalk forward, with no sense of what truly happened before the 1900s. How is that not strange for any of us individually? What if I become the family’s Plutarch? How might a child’s identity differ if they had detailed accounts of their relatives, generations up the chain? I suppose you could ask the great^6 grandchildren of writers. Claude tells me there are 700 members of the Monticello Association, each a genetically-confirmed descendant of Thomas Jefferson, who wrote 19,000 letters, books, and a Bible. A few of them have problems with him being a slaveowner, with one publishing an essay called “Take Down His Memorial.” At least they have 255 other ancestors to respect.

I did not expect to be able quote whole scenes of The Sandlot (1993) from memory, but there I was, the annoying co-watcher to my wife who barely remembers it. I must have watched it a dozen times. If not, the few viewings of it must have been a religious, formative experience. Somehow it came on, via streaming, already more than half way through, but early enough to be inside of the dream of Benny Rodriguez¹ where the ghost of Babe Ruth delivers his classic line: “Remember kid, there's heroes and there's legends. Heroes get remembered, but legends never die.”

Did this quote shape my elementary consciousness? Many of my essays here are about “textural immortality” and legacy—doesn’t that word have a shared root with legend? Has my drive to devote my life to creating something memorable (something that outlasts me and shapes the future) a product of a 1990s cult film with a $7 million budget?

Obviously the answers to those questions are lost; all that is left are fuzzy caricatures to reason with. I can’t know exactly the evolution of my psyche, but it does seem that in almost every phase—from baseball, to music, to architecture, to technology—there was this boyish desire to be Ruth-like, to master and transcend a genre, to have a bunch of goofy nicknames, to have leagues of kids yell my name in unison, and to be remember beyond my life. To lean into and live by that line is to become a megalomaniac.

There is a second half to that quote (which is less memorable): “Follow your heart, kid, you’ll never go wrong.” This disarms the grandiosity of the prior line. The goal is not to become a legend for legend’s sake, but to be attuned toward your heart (towards “the way,” nature’s order, the virtuous thing, the hard thing) which puts you on a path, perhaps towards doing legendary things, but the path is the point.

The other day I was listening to a podcast and noted “the purpose of life is the transmission of legacy.” The context is that in the face of death, we strive for immortality in different ways. The immature and impossible version of this is physical immortality. Religions promise spiritual immortality. Pharaohs and estates focus on material immortality. They referred to another option, “secular immortality,” which I’d rather call “symbolic immortality.” This is about living into the future through art, language, and symbols. This can be more modest than the cultural immortality of Babe Ruth; this can exist solely within the family. I’m talking about the paintings we have hung up of my wife’s grandmother, and the sayings from my great grandmother that I’ll pass down (“be your own person, choose your friends wisely”).

There are two ways to think about death. The first is cosmic deflation, to realize that Babe Ruth, the entire culture he's within, and even the species itself, are all just a temporary evolutionary blip; if everything will be cosmically forgotten, then it’s futile to strive to be remembered for anything. Alternatively, you could see your immediate chain, the generations before and after you, as equal to yourself, to see the whole lot of you as a single entity, and to act in a way that could be exemplary for your kids.

I published 38 "essays" in June, averaging at ~600 words, totaling at ~22,800 words (that's a pretty good month for me; I usually go between 10-30k). That same overall output could also be spliced up as four long form essays at 5,700 words each. The question here, can you count these small things as essays?

If you look at Montaigne, and especially Bacon, they each had some shorter one around 500 words. I have other contemporary essay book that feature writings that are exclusively 2-3 pages each. So historically, yes, there's a case for short non-fiction musings to be called "essays," but is it really about shortness?

It's more about formality and effort. In recent years, I was set on writing "unitive essays," ones that integrated all the known patterns, ones that went through many rounds of editing, ones that would be timeless. I still, of course, value that and aspire to it; I'm just currently in a phase where time is more burst-like. Such is life with a 5-month-old daughter. Deep flow states are hard to come by, and so instead, I'm logging little ideas all day, and whenever I get to the computer, with the mental space to write, the goal is to pick one idea and articulate it fully. Can I write and publish this idea, here and now?

It's an approach void of editing, which feels right for right now. I've thought so analytically about the craft, and the goal now is to see if I can weave in patterns on the fly. This doesn't mean I can successfully scope and prose every idea to a 5/5 on a single go. Most ideas—including probably this one—are started pre-maturely, and have limits on what they can become without scrapping it all and restarting from a new frame. Of course, the point is for ideas to mature through writing, but a great thesis can be so cognitively reorienting to nullify a draft's whole premise. But maybes that's the thing to build towards?

I didn't have this idea before I started this essay, but maybe an essay should contain an earnest shock, something in the moment that negates, inverts, and breaks the structural logic above. Wouldn't there be a thrill in witnessing a live epiphany, and then watching the writer clarify how everything previously covered may be true/false in light of the revelation?

You may have noticed, every paragraph so far has ended with a question. I suppose I'm playing with this idea to start with a clear question, and then continuously drive forward until a spontaneous question triggers something new, and I can fold back into that original question with an answer from a different dimension, a side door I never knew existed. An essay is less about the length; whether it's 300 or 30,000 words, it's more so about the value of what's discovered.

I was looking at my archive earlier, at everything I published in the last year. There are 363 "essays" (most of which are expanded logs), averaging at 370 words each. Of those I have about 22 essays flagged as "favorites," meaning, they've elevated to a special section, and earned the formality of cover art. This means that only 6% of the ideas I write in a given year are worth carrying forward. With time, that will probably atrophy even further. Even 1% of output per year is high: if you can write 3.6 timeless essays per year, that's prolific. DFW, if you look at what was anthologized over his career, only put out 1-2 per year. One approach to this is to pick be very selective, only chiseling a hand few of ideas; the other is hyper-publishing, trusting that curiosity will bring you to unexpected places, and the emergent "winners" are not ones you could ever predict. What makes something a winner?

It must be a fusion of things; again, quality is the transcendence of categories. This gets into what-makes-something-the-best-essay territory. The originality and nature of the subject itself matters, which is part of why I like the idea of reading and writing wider. But the essays I like most are the ones that also fuse in most or all of the compositional patterns around that thesis. There's only one I wrote in the last year that comes close. Maybe all of them have some personal experience peppered in, but the best ones, I feel, are ones where the writer is deeply immersed in a place, and all the things about them become allegorical. So you can read and write, quick or slow, short or long, but what you make is shaped by how you live, which is why it might be worth capturing your daily thoughts in prose.

Frigid in the machine-cooled nursery I look out over the low-rise sprawl of roofs and canopies and see what I remember as and now call the pom pom tree, a sole trunk towering above treelines and wires, with wooden skeleton hands reaching up and into the blue, yet skewering only through shaggy green balls, the poms, again sighted all from this nursery, a mysterious one, for I walk down that main boulevard every afternoon but never notice poms for they glide above the sight lines of the side-walk, and so here, and so now, observing this dying thing suspended 30 feet above the town, the village of floating spheres, home to ticks and ants and loraxes I'm sure, it reminds me of what I saw yesterday, those Lesser Poms east of home at ground level, where that Japanese landscaper with her hedgeclippers existed in that only moment I'll ever know her, whom I said hello awkwardly, who did not see the unattended child of an aloof mother when he snuck an empty wrapper into her bush, or so I thought I saw and double-taked and daydreamed of moralizing him, and this is what I think as I type into my Oracle, who incorrectly diagnoses the disease of this pom tree as witches broom. Witches Broom? No Claude, no, this is not a clot of bird twigs, and so I sent it a pictures and then it tells me, ah, of course, Verticillium Wilt, and that seems still wrong but slightly closer to the truth, for it does look like this tree is losing its vascular system unevenly, and yet even more true because it resembles my own numb arm, an uneven vascular, where my daughter's heavy head—her 86th-percentile head—pinches my ulnar nerve for hours of unclocked time each day as I read pre-Socratic philosophers from ebooks and remember the times I had to be investigated in expensive offices where fast-talking doctors lathered my arms in jelly and shot electricity through them but could diagnose me no better than my pseudo-Oracle despite their graduate degrees, and now I look down and imagine my arm itself as the naked pom tree, with only scant patches of flesh and tissue over fully exposed forearm bone, and there it is that ulnar nerve in plain sight, and I see it black and dying and in need of a clip, if only to release that black astral voodoo I acquired from weak composure in an equitorial skirmish, and if only I could find and cop a clip from that landscaper who I will surely never notice again despite she herself is a walking distance mystery who will yet never step foot into this refrigerated machine-cooled nursery.

Bernie wants to pull off a 50% one-time equity tax on the top 3 AI firms (OpenAI, Anthropic, xAI). This is ripe time for a mainstream populism to ride the tailwinds of AI populism, tapping into hatred and impending doom and the whole gambit of middle class paranoia, ripe time to propose a century-defining redistribution scheme. He opens by saying that AI was stolen from us, built from our collective intelligence, and therefore it's a national utility that the people should own. To ground it in reality, he used the Alaskan sovereign wealth fund as precedent, citing how citizens get paid annually from oil sales. We'll likely see many more of these proposals leading up to our 2028 election. But after you do some napkin math, you realize that this plan is bogus: no one would agree to it, and even if they did, it wouldn't benefit the American people.

This is citizen ownership in rhetoric, but government ownership in structure—a passthrough mechanism as a Trojan Horse with Pete Hegseth and the goons inside. Realistically, I don't think this is meant to be a serious proposal; the labs won't accept it. It's more so a gesture to buy goodwill for the Democrats at a time when mass hatred for AI is cresting.

Here are the issues I see with the concept (along with some grasping for solutions):

1_We don't need government equity, but guaranteed royalty distribution:

This is not a profit tax, but a way to formalize government seizure through an equity transfer. It even comes with board seats within thees AI companies. Remember, this is the same government that tried to force Anthropic to allow unrestricted domestic mass surveillance and autonomous weapons. The equity only gets to the citizens if the stock appreciates, they convert it to cash, and then decide to write welfare checks. Does our current government seem like a voluntary patron of citizen welfare right now? Will welfare checks beat Iran and China? And even if this were intended to be a passthrough mechanism, it would be very hard to make all that equity liquid.

The Alaska fund that Bernie mentioned is structured very differently. It's anchored not in equity, not in profits, but in revenue. 25% of Alaskan oil revenue goes to a constitutionally-protected fund, which is then reinvested into the stock market; the principle is locked and the dividend is split among citizens, usually $1-3k per year. Could a similar model work for AI companies?

This would never work with profits, because AI companies aggressively reinvest. In the short-term, an AI company would resist a revenue royalty because it would slow expansion, but: (1) if all companies did it, they wouldn't be disadvantaged; (2) it beats equity because they retain full control of their company; and (3) if they believe they'll be wildly profitable, then a 10% royalty is possibly more than half of what dividends would pay from 50% equity. So what could a 10% royalty return?

By the 2040s, annual AI revenue could be $20T globally across software, hardware, data centers, and energy. If America has half the market, and 10% is distributed to a citizen fund, that's a $1T annual budget, completely liquid. So how do you use it?

2_ We shouldn't redistribute equally, but strategically:

Alaska has 738,000 residents. The US has 350,000,000, almost 500x bigger. You can do equal distributions at the state level, but at the federal level it'd ineffective. When we talk about UBI or even Elon's UHI (universal high income), we need to realize that U doesn't work at scale beyond pilots. $1T distributed to every American citizen yields $2,857/year. This matches the upper-end of Alaskan payouts, but it's nowhere near what we need to account for AI-driven automation and disruption.

And so instead we need to be strategic over how we distribute it to cover the wide range of effects. Maybe 50% of the fund is reinvested, and the dividends are redistributed based on income (with most of it going to the bottom 10-25%). The other half can be used on housing, free medical diagnosis and prescriptions, free education, New Deal style jobs concentrated in areas that can't be automated (childcare, healthcare, etc.). Who decides this breakdown?

3.Instead of a cabinet agency, this needs an independent board:

If we want citizens to own AI, then we need some form of citizen representation to guide it's growth, otherwise it all devolves into technocratic expansion and war. You could imagine some kind of tripartite board structure, where it has government reps, industry reps, and citizen reps. Any single branch has a myopic set of interests, including the citizens. The citizen branch might undervalue national security or capability improvements, but without it, there's no one representing the problems that hundreds of millions will face.

What I'm reaching at here, I think, is that it's more than just getting a check for theoretically contributing to the LLM hivemind. There's something important to me, as a citizen, to have some say in where AI royalties are redirected. Whether I participate simply as a voter, or I work hard and get anonymously elected to represent my state for a single issue within a liquid republic, who knows. And again it goes beyond just getting and allocating money, but this board should be involved in AI-related policy, especially as it relates to domestic matters.

It's unlikely that power will just be granted to citizens, for they have no leverage next to the ones with the tanks and algorithms. But as the governors and technocrats quarrel, there's a world where a mediating party comes in, and maybe it's their role to insist that a citizen branch can help round out the dynamic.

This last point has basically veered into redesigning government itself, which is both out of scope, but also, possibly, exactly the point. Bernie's whole play is to let the people own AI, but for that to actually expand beyond populist rhetoric, citizens need a more meaningful way to engage with civic matters than to vote for a president once every four years, they need actual representation.

Sometimes the coolest website is the least readable.¹

I recently came across gwern.net and quickly sensed it would be a personal-website-as-labyrinth that I'll venture into for weeks. It has an alien feel to it, or at least foreign relative to the optimized and foolproof UIs you find across templated social networks. He is a Wikipedia editor with 34,569 edits (on English Wikipedia as of 6/1/26) and so naturally his personal website is a personal wiki, documenting his self, his site, his links, his tech stack and writing, each adorned with hierarchical outlines on the left (1, 1.2, 1.2.6, ... ). I sense him to be something of a techno-Montaignean, capturing his mind and culture, interweaving quotes, and pseudonymously appearing on the Dwarkesh podcast as a real-time avatar.

So yes, lots of diving and mapping to do, but I need to note one observation of my experience here, which I want to be careful not to recreate on my own site. Most of my time is spent marveling at the structure and navigating what exists, but I'm presented with so many hyperlinks that I can rarely ever focus on and absorb a single page. There are 53 links in my current view. Maybe I'm exposing myself as someone who reads linear essays a lot more than I read Wikipedia articles.

I suppose there are two ways to know a person, in breadth and in depth. Technically this site has both; once you wade through the peculiar structures and get a gestalt of the person, you do find linear essays that are well written. But even those are nested in scaffolding; 60% of the opening view is dedicated to metadata: nav links, title, tags, a summary, ratings of completion, certainty, and importance, links to similar notes and a bibliography (many of which, if clicked, opens a pop-up with more information), and then an opening quote, all before the opening sentence.

Even if I think this meta-data is misplaced, I personally love having it all accessible. I get frustrated by a popular online writer (/marketer) who refuses to date the essays on his website, probably from the thought that datelessness is timelessness, or the fear that the median reader will see something dated 2019 and think ugh, that's old, and click away. Marketers want a simplicity that's legible at scale; I am a complexophile. A personal website (or anything, really) should be as dense as can be contained, for that gives the super-reader the ability to grok you at a resolution closer to reality, but only as long as it can be progressively revealed, giving the first encounter an on ramp into the beast.

I'm now arriving at what I think I believe: if your website contains a collection of essays, then drop the reader directly into prose, and withhold structure until the end of an experience. "Prose before portals" could be a simple, multi-scale maxim. A standalone essay page should have a header of only 15% metadata, and even the frontpage, instead of providing a traditional orientation, could drop you directly into a stream of recent essays (a design decision I haven't committed to yet, but am leaning towards). Perhaps portals could exist minimally at the beginning, but maximally at the end. An essay's footer should be entirely portals.

Another debatable decision is that an essay should rarely include internal hyperlinks. Contrast this to Justin Hall's links.net of the mid-90s, whose whole website was a hyperlink maze. Gwern's site, much like Wikipedia, is also maze-like. These are conceptually neat, and of course native to the Internet, but I always catch myself skimming rather than reading deeply. I am astonished at the size and grandeur of the park, but I am distracted. Essays demand depth. My ideal would be to fuse the medium of physical reading with the navigation of the web: uninterrupted prose, bookended by optionality. Maybe you could refer to this as "extrastitial" instead of "interstitial": the internal modules aren't connected, but the wholes are connected end-to-end. (This actually mirrors how ChristopherAlexander structures his chapters in A Pattern Language, the original wiki: the beginning and end points out to other chapters, but the body is uninterrupted.)

A final note on skimming: I catch myself doing "Inspectional Reading" a lot here, the second level of Adler's How to Read a Book. There are many possible causes for this. To start, it could just be my fault: right now I'm reading as I write this essay, and I have much to do this morning, and so to some degree I'm reading to the level that it enables me to write, for if I read everything full, all the tabs, I could become absorbed for hours and get nothing else done before it's time to watch my 5-month-old daughter for the rest of the day. But aside from self-blame, there's a FOMO that comes with any thriving website: when you're aware of a sprawling network of high-quality information, it becomes hard to sink into any one piece because you're too aware of what you're missing. And so there might be something to intentional concealment and revelation.

I want a reader to come to my site and experience flow, not analysis paralysis, but this opens a new question. Who is a personal website for? The answer is in the name. The reason I'm shifting from Substack back to a site of my own is because I want to write in a place where I set the rules. And so there's a risk of leaning too far into becoming a self-archivist, where I try to convey to you the totality of myself, the full hyper-object, instead of letting you compile me one file at at time. If the full extents of my writing are something like a national park, I need to make sure you get on the curated trails and experience nature, instead of presenting you a network of maps.

Ironically the first essay I read by Gwern was on Tools for Thought, a wonderful takedown or Rome, Zettlekasten, and networked thought:

"Most people simply have no need for lots of half-formed ideas, random lists of research papers, and so on. This is what people always miss about “Zettelkasten”: are you writing a book? Are you a historian or Teutonic scholar like Niklas Luhmann? Do you publish a dozen papers a year? Are you the 1% of the 1%? No? Then why do you think you need a Zettelkasten?"

A rule I've had to set for myself is to never link my notes; they should live scattered in an epiphany swamp of atomic ramblings, only to be given name, date, and tag at the moment of publishing. Most won't make it out of the swamp. So many writers suffocate themself in PKM hell; instead they should open the pipeline to get finished prosed onto their website. And now, I find myself reaching for heuristics on how to present essays, a whole body of work, and the very self behind it. I think there are similar risks with public hyperlinked structures, along with ways to let the atomic nodes of a network speak for themselves, without severing from the hive.

This is all just first wind from second impressions, but as I understand Gwern more deeply and build out my new site—after existing only on Substack for 3.5 years—, I'm sure I'll come away with something useful.

a term from Heraclitus adapted by Jung, is about something turning into it’s opposite. “dromia”>“anti” is “to move towards what you are against.” For Jung this was about how the shadow mirrors the development of the ego; as you define and act out your virtues, you subconsciously brew a secret complex of evil within you.

This extends far beyond the psyche though: when capitalism turns to hyper capitalism, it turns int its opposite, socialism; when a company with a mission statement maximizes revenue, it fulfills its anti-mission.

Why does this happen? There is danger in adopting a position without earnestly considering its opposite. When you take a stance, major or minor, you inherit the full logic of the spectrum, regardless if you acknowledge it or not. Unless you operate perfectly, there is only one direction to drift; and if you do operate perfectly, you deplete the conditions that make that pole viable.

In order to prevent this, you need to consult the shadow at the origin, else it slowly grows and lurks, unaccounted for, without your doing.

Link to one of your pieces you want to make sure we read. Why is this a good example of your writing for this progress blog-building program? Why are you proud of this piece?

Essay Writing as Personal Sovereignty was a winner of the Cosmos Institute Essay Prize, and it speaks to the importance of the manual effort of writing essays through the age of AI. It looks back to the origin of the essay, and how the early tradition of Montaigne failed to scale and integrate into our systems of mass education. I'd like to use my fellowship to go deeper onto this, to explore the history and future of writing curriculums.

What topics or areas do you want to write about? What about this is interesting to you? Why does it matter?

I've been blogging for 6 years and published over a million words. I want to study the history of education, writing, and autonomy, so that I can charter a vision for writing curricula in the 21st century. In 2024 I won a $100k O'Shaughnessy Fellowship, which enabled me to write a textbook on essay composition, and develop software that can analyze craft along a pattern language I designed. Focusing on history and progress will give me the context I need to found an institute dedicated to reviving how we teach the essay at scale.

What is your "angle" for human talent & potential? What particular areas (e.g. workforce development, adapting to AI, education, immigration, fertility, gender), challenges, or opportunities do you want to explore?

Human potential is gated less by talent and more so by the mechanical way we've taught writing at scale. AI is dismantling that system and creating a new opportunity. A new writing curriculum, grounded in autonomy, would be anchored in software that helps a writer improve how they can articulate ideas they actually care about. In this model, AI would never write for them. They would be guided by a series of "margin muses" (editors, socratic agents) both within and outside the piece. Over time it will understand a student's strengths and weaknesses, and guide them down a custom track of readings, lessons, and exercises. By compressing the arc of mastery from years into months, students will feel their rate of progress and continue toward the pursuit of their own original ideas. By fixing this, we don't just get better test scores or literary prose, but a wider pipeline of articulate, critical thinkers.

Tell us a bit about your background for the human talent & potential track. What unique knowledge, experiences, or perspective do you bring to exploring progress in human talent & potential?

1. As Editor in Chief and curriculum lead at Write of Passage, I helped thousands of writers improve their ability to write, and distilled insights from thousands of drafts into a pattern language and 25k-word textbook on essay craft;
2. I hosted a $10,000 essay prize last year that resulted in The Best Internet Essays 2025, an anthology that fused AI and human judgement. My editing system scores each essay 1-5 across 27 patterns; AI provides an objective "craft" score, while human judges cover the intangibles. Currently improving my eval system and aggregating RSS feeds so that I can scout the best essays across Substack in 2026.

My unique perspective: I've felt the dramatic rate that writers can improve, and I think we can measure and augment it too.

Share a great essay you've recently read on human talent & potential. This could be something exploring a policy question, a recent phenomenon, or an exploration of the impact of an innovation, or even a utopian vision piece. What about this essay speaks to you? Which ideas resonate? Why does this essay matter for those interested in human talent & potential? What perspectives might you add?

Check out The Age of the Essay by Paul Graham. This essay is a pillar I come back to, because it covers history, process, and future: he critiques the history of writing education (the five-paragraph essay is a hangover from medieval law schools), explains how essays are actually a multi-branched exploration to a question, and then speaks to how the Internet could enable the 21st century to become the age of the essay. I find it interesting that Graham wrote this not long before he founded Y-Combinator Sep 2004), and wonder how much of his thinking here influenced the success of that program. Many of the notable founders in cohort 1 were bloggers who used writing to think (Aaron Schwartz, Sam Altman, etc.). Related to progress, I think there's a meta-lesson in understanding how new technological networks can open up new affordances to revive old practices.

An added perspective: Graham was right in that the removal of gatekeepers opened up a new wave of writing talent, but missed the fact that it also opened a new flood of slop that would make that talent harder to find. The important lesson is that you can't remove gatekeepers without implementing a sophisticated curation system. I write about this in my essay "The Signal in the Slop," the opening of my anthology, The Best Internet Essays 2025.

Your current situation. Give us a bit of context on you--e.g., what you're working on now, at what organization, and anything else you want us to know about you.

I'm working full-time on my project Essay Architecture: writing, researching, building software, scouting essays, organizing a community, and hosting weekly calls where we deconstruct classic essays. In the last few years I built an audience of 10,000 followers, and now I'm figuring out how to formalize my efforts into an institute (sustainable income paired with mission-aligned projects).

Writing and your career. How do you see writing on progress topics fitting into your career plans over the next 5 or so years? As you envision your success as a writer, what do you want to accomplish with your writing in the next 5 years? Do you have goals on frequency of publishing, places you want to publish, or audiences you want to reach?

Within 5 years, I want Essay Architecture to function as a standalone writing institute that different groups can plug into: Substackers, students, micro schools, homeschoolers, etc. It will provide editing software, textbooks and anthologies, a library of thousands of scored/categorized essays, and the ability to guide writers down custom learning paths based on the drafts they upload.

The goal of my progress-related writing is to: 1) publish pillar pieces on the importance, history, and future of writing curriculums; 2) attract students to the institute; 3) build a network of partners who are operating within or connected to the worlds of EdTech or alternative schooling.

I'm in the process of rethinking my writing infrastructure. All essays will live on a personal website (launching in June), where Substack will serve as a weekly newsletter to redirect readers to my essays, products, etc. I believe it's important for a writer to manage different publishing velocities. In May I published 33 essays averaging ~600 words each. In the last year, I've averaged a monthly long form essay at ~3,000 words. I'd like to produce something at my peak quality that gets published in a journal or magazine around 2-6 times per year.

What are you looking to get out of this blog-building intensive?

I'm looking to immerse myself in a community of progress-minded writers, to get rigorous feedback on my ideas, and find guidance on how to formalize my project into a sustainable institute.

Aristotle’s virtues are structured as the mean between two vices; “temperance” is the mean between indifference and indulgence; “courage” the mean between “cowardice” and “recklessness.”

I’ve been working out a system of virtues where paradox is the organizing element. It’s not about finding the mean of a spectrum, but about simultaneously straddling two opposites, two ends of a spectrum. But the spectrum here doesn’t run vice-to-vice—you wouldn’t want to be cowardly and reckless—, it covers two opposite modes of thinking: right brain, left brain.

Right brain virtues are about embodied presence, where left brain virtues are about abstracted principles. Both matter, and if I lean towards one mode or the other, I find myself untuned, either scrambling through passion, or strangled by structure. The solution isn’t to shift from order to chaos or chaos to order, but to be maximally orderly and maximally chaotic.

Kairos is about being aware of a moment and boldly taking it (it’s a military term) where agape is about unconditional love (a Jesus term), and so when I repeat the prayer “Καιρὸν θεωρῶ, ἀγάπην σπερῶ,” it’s a paradox embedded in a single phrase: “I recognize the moment, and will bestow love as a gift.”

I haven’t mapped the other virtues into sayings yet, but there is the spontaneous, generative, and wild ecstasy (ékstasis) paired with a prudent and monk-like systemization of everything, logos. There is the serene inner stillness, the now without thought, hesychia (ἡσυχία) paired with the striving towards your destiny, your purpose, your final end, your telos. There is the immersion into the inner dream-world of images, fantasia (φαντασία) paired with the builder mentality to order and craft your environment to shape your mind, cosmesis (κόσμησις).

Now that I write this, I see the difference between cosmos and cosmesis. Cosmos is an abstract, left-brained noun, the order of matter, it's physical configuration; cosmesis is the embodied, right-brained verb, the participatory act of ordering matter yourself (ie: making your bed, shaping your government, designing your church). It's important for all of these virtues to be verb words, because they are not static nouns, but actions to take. In that spirit, I should change logos to logismos, telos to teleiosis, and agape to apagan.

This is turning into a pattern language of virtue, and though there are many differences with the Essay Architecture pattern language—it’s made of spectrums and not triads—there are similarities too: each virtue telescopes into more sub-virtues, virtues are interlinked, they all combine to create a nameless quality. I think only through making many types of pattern languages, across different fields, will I be able to understand the different constraints and components of any system: the patterns of pattern languages.

I finally got around to building my fiction syllabus. In pursuit of the question, "how should an essay writer read?", I'm mapping out all the different ways I want to educate myself. One of them, reading and analyzing essays, is obvious and underway, the bulk of Essay Architecture. But the 2nd focus was focused on nonfiction curators, historians, and biographers—I already shared that list. Now this 3rd focus is fiction.

This list started with some big bad novels, like Moby Dick, Middlemarch, and Infinite Jest. Realistically, if I were to pursue any one of those, they'd likely suck the oxygen away from anything else I'm reading. My current approach to read something like 10 books per month, not in full, but 1-3 chapters from each, coordinated among each other. I could possibly read something like Infinite Jest over 6 months, but I imagine I would lose a lot from going in and out, and often lose context of what I read last month. Maybe there's a way where, for one month a year, I block out the whole month to read something very long. For now, going to skip that (I can experiment with long books after this already ambitious system proves it can sustain for 1-2 years).

And so this limited my fiction criteria to things I could knock out in a few days. Decided to run with short novels and novellas (100-200 words) and also short-story collections (where I'd select a few that can be read in a similar span). I like this approach because it gives me a wide range of different voices and approaches to world-building, character building, etc. Where the essay is anchored in the questioning of the author, and nonfiction is anchored in ideas, fiction is anchored in the confluence of people and place, and the implicit virtues you parse out from the circumstance.

You can get the whole reading list on syllabus for $208.

• Atwood, Stone Mattress, 2014 (Alphinland, Revenant, Dark Lady, The Dead Hand Loves You = 130p) $9
• Balle, On the Calculation of Volume Part I, 2024 (160p) $10
• Borges, Ficciones, 1944 (The Library of Babel, Funes the Memorious, The Garden of Forking Paths, The Imortal, Death and the Compass = 64p) $8
• Butler, Bloodchild and Other Stories, 1995 (Bloodchild, Speech Sounds, The Evening and the Morning and the Night, Amnesty = 115p) $9
• Chekhov, Selected Stories of Anton Chekhov, 2002 (A Boring Story, The Darling, The Man in a Case, Gooseberries = 86p) $11
• Chiang, Stories of Your Life, 2002 (Story of Your Life, Understand, Hell Is the Absence of God = 100p) $9
• Davis, The Collected Stories of Lydia Davis, 2009 (Break It Down, Story, The Thirteenth Woman, Kafka Cooks Dinner, Varieties of Disturbance, We Miss You & selected shorts = 80p) $15
• Dickens, A Christmas Carol and Other Christmas Books, 1843 (90p) $6
• Dostoyevsky, The Best Short Stories of Fyodor Dostoevsky (Notes from the Underground, The Peasant Marey, A Gentle Creature, The Dream of a Ridiculous Man = 176p) $7
• Goethe, The Sorrows of Young Werther, 1744 (130p) $3
• Hemingway, The Complete Short Stories of Ernest Hemingway, 1938 (Hills Like White Elephants, A Clean Well-Lighted Place, The Snows of Kilimanjaro, Indian Camp, Big Two-Hearted River, Old Man at the Bridge, A Day's Wait, Now I Lay Me, The Gambler the Nun and the Radio, Cross-Country Snow (104p) $17
• Hesse, Siddhartha, 1922 (150p) $4
• Johnson, The History of Rasselas, Prince of Abissinia, 1759 (120p) $5
• Joyce, Dubliners, 1914 ("The Dead", "Araby" "The Sisters" "A Painful Case" "Eveline" "Counterparts" "A Little Cloud" "Clay") " (111p) $1
• Kafka, The Metamorphosis, 1915 (75p) $9
• Kerouac, The Subterraneans, 1958 (110p) $10
• Le Guin, The Unreal and the Real, 2012 (The Ones Who Walk Away from Omelas, The Wife's Story, Buffalo Gals Won't You Come Out Tonight, Nine Lives, Vaster Than Empires and More Slow = 150p) $10
• Munro, Hateship, Friendship, Courtship, Loveship, Marriage, 2001 (The Bear Came Over the Mountain, Family Furnishings, = 68pp) $7
• Porter, The Collected Stories of Katherine Anne Porter, 1965 (The Jilting of Granny Weatherall, Flowering Judas, Theft, Noon Wine, Pale Horse Pale Rider = 135p) $16
• Tolstoy, The Death of Ivan Illyich and Other Stories, 1866 (The Death of Ivan Illyich, Father Sergius, Alyosha the Pot, Hadji Murat = 232) $14
• Vonnegut, Welcome to the Monkey House, 1968 (Harrison Bergeron, Welcome to the Monkey House, Long Walk to Forever, Miss Temptation, All the Kings Horses, Tom Edison's Shaggy Dog, New Dictionary, More Stately Mansions, Report on the Barnhouse Effect, The Euphio Question, Unready to Wear, The Kid Nobody Could Handle, EPICAC, Tomorrow and Tomorrow and Tomorrow = 168p) $6
• Wallace, Oblivion (Good Old Neon, Another Pioneer, The Soul is Not a Smithy = 105p) $10
• Wilde, The Picture of Dorian Gray, 1890 (190p) $6
• Woolf, Mrs. Dalloway, 1925 (190p) $7

I asked Claude about the running themes: awakening late in life, the divided/counterfeit self, free will, the dignity of ordinary people, the sacredness of attention, and memento mori as a clarifying lens. Many are anchored in a single day. Some try to synthesize virtues, others accept a messy plurality. I also asked "how might I change after reading this?" and it replied: "you'll re-weigh the ordinary day"; you'll get a sharper instrument for self-deception"; "you'll relocate ethics from achievement to attention and kindness"; "mortality becomes a working tool, not a fear."

The advantage writers have in the age of AI is their ability to quickly write with extreme specificity.

A non-writer might just prompt “Generate a slide deck visualizer app,” and the results will be fine but random, totally different if you were to run it again in a fresh chat. When you ignore the details of craft, slop fills the gaps. Alternatively, if you can write out 300 words of instructions, including the goals, the aesthetic, the back-end decisions, the features, the data structure and variable properties, etc., you’ll get something to the degree you can visualize it in your head and describe it.

I suppose that is the act of the writer: visualize, then describe. The same applies to vibe coding. The future belongs to those who can think in paragraphs.

Not only can the writer trivially write 50x more than the lazy prompter, they can write with 5x the specificity. Those numbers are arbitrary, but it feels true that a seasoned writer can achieve 250x the semantic density of someone who does not work with words as their dominant output.

1. As a writer needs a site of one's own, a place designed for their particular psychology so they can be the most prolific, honest, adventurous version of themselves. Solitude is important. Montaigne, the founder of the essay, wrote up in his tower for a decade. When you are your own audience, your practice is self-justifying. You are intrinsically fulfilled, and do it regardless of validation, growth, or revenue. To become self-validating is to become a nuclear engine of creativity. When you write on your own site, chances are you will spend much time on ideas that no one will read. That's inefficient, but essays are inefficient. I need to ruthlessly follow what matters to me, with no fear of being illegible or invisible to others.
2. That said, you can and should invite others into your garage. I still plan to keep my Substack and post there, but it will be more like a newsletter, a digest of the controlled explosions happening in my own neighborhood. I do believe in the value, even, the responsibility, of writing in public. By making your place tidy enough for friends, strangers, students, customers, mentors, heroes, whoever, to come in, it makes you put an extra oomph in your crafting of language, and it creates seeds from which relationships can grow. When you have visitors in your territory, they play by your own rules, so you're generally safe from mobs and barbarians. They will not trample over your furniture and throw the books from your shelf like they would in the town square.
3. In 2023, I was hopeful that Substack could be an all-in-one platform—a website/newsletter/discovery engine—but it has heavily shifted into an app-centric social media platform. The app starts you off in an endless, algorithmic, engagement-ranked feed, and the design has slowly evolved to trap you in the app. When you click in article, the default URL is the Substack one. When you click into a person, you can't even go to their site anymore; you can only view them through their profile template. This means all the customization and self-archiving and mythologizing that goes into your site is off limits to the app, the thing they're trying to corrall attention through.
4. I'm very allergic to "Substack is dead" posts, and most of the critique is often a projection of their own weaknesses (ie: when people naturally stop growing, it's easy to blame the algorithm than to take responsibility for it). In my case, the Substack algorithm has worked pretty well over the last two years, and I'd be stupid to abandon it. But the whole system has limited my intrinsic passion to write, and that matters more, enough that I'm willing to take the risk with a split publishing system: Substack newsletters that link out to my site.
5. Back in 2020, a Write of Passage concept was the "public to private bridge," meaning you find people in social media feeds, but then redirect them back to a place of your own. Now that Substack is mostly a social media network, I think that same strategy applies. It's not where I want to host my essays anymore. I'll host newsletters and paid content there, but the timeless stuff wants to live in a place that is timeless.
6. If you have a portfolio of writing, Substack feels like a pretty bad way to make your old work legible, especially within the app. There are no tags or sections. No about page. No navigation system. No ability to frame call to actions as visually dominant. The beauty of your website, especially if you build it from local markdown files, is (1) you have a single source of truth for all your writing, and (2) you can just respawn new interface and navigation systems as your portfolio evolves.
7. Even though Substack lets you export your essays, it's really more like a failsafe, a backup incase you ever decide to leave. Of course, it's very nice to have that! But it's still a cloud-based system, where editing your past files is slow and clunky, and you have limited ability to point your essays elsewhere. When I have a local folder of my essays, I can very easily spin up a stylized website around any essay, or any group of essays (say, for example, if I'm making a proposal and I want to curate a handful of essays. I can point my AI at any combination of files and folders for context.

What would a 3D essay look or feel like? The "video essay" is a format, but that's really more like a performed/spoken essay with picture and video over it. I'm curious what it could be if we keep reading prose as the core mode.

Here's a prototype where scrolling brings you in instead of down. Instead of feeling like you're just reading a wall of text, it feels like you're moving forward into a series of spaces.

This breaks the essay into paragraph blocks, where you only see one at a time, which works something like focus mode (and I suppose there could be a way where you could preview the paragraphs behind and ahead). There's opportunity for each paragraph to have unique color, imagery, a distinct vibe to match the content. Additionally, each paragraph can have portals to jet out from this essay into different ones, making it something like a choose your own adventure.

Is anything gained from this? Or is it just a novelty? Best case, it's a new medium to bring prose into the short-form video era; it's much less intimidating to be presented with a single screen of text than a whole wall of it.

You’re Ideas Don’t Matter? This take always irks me, though I do love the closing line: "You can [...] spend your life [fighting over] golden eggs [...], or you can learn how to become a goose who lays golden eggs." I love the abundance mindset; just be prolific.

But I don't love the "fuck originality" attitude. It feels like a node in the creativity-for-beginners canon—along with The Taste Gap and All You Need is Vibes—a consolation to prevent a new artist from quitting. And I suppose that is worthwhile. You can't be terribly concerned with technique or originality if you don't have momentum, the general contours of a practice.

But to say that creativity is only "remixing, rearranging, reimagining, and recombining" is to plant a meme that can constrict creativity long past its usefulness. I don't totally disagree—yes, all ideas have a lineage of influence, and most big ideas are reframes of old ones for a new context—but the issue is in being too conscious about it. To see creativity as the controlled combination of elements is to see the creative process like a mechanical assembly line. It ushers in factoid harvesting and Frankenstein stitching. This kind of recycling is halmark slop, the kind of thing that LLMs do.

And again, that is totally fine for L1 or L2 or whatever, but the goal—or at least, my goal—is to transcend that. Originality isn't an old virtue to shed, it's the thing to strive for. It takes a lifetime to get there, decades of dedication, and that is a hard promise to make to a reader who has a time horizon of next week. But what is it that you should strive for if not originality? Instead of combining ideas in an A+B=C kind of way, you want to melt and fuse them all in your subconscious, in an unpredictable, high-voltage kind of way, to create an output that is incalculable, one that of course has nods to works from before it, but one without a formula, and one that could have only been crafted from your own mind. Is originality not the same thing as make the thing that only you can make?

In October of 2024 I sliced history into eras of my own. Prior to that, my historical timeline was built on sandy approximates. The challenge here is that so many historical eras have different time periods (10, 50, 250 years), and so it requires you to remember specific date ranges for specific things. Unless you’re a historian, you most definitely won’t.

I’ve been long drawn to the Strauss-Howe generational theory, and decided to use this as a historical map of even intervals. They break history into “saeculas,” 80-year cycles, the interval of an average human life, and perhaps not coincidentally, the interval between major world conflicts. They go back to the 1370s, I think, but I’m trying to work through the major milestones in the 400 years before that (which includes the Schism, the Crusades, the founding of Oxford, the Magna Carta, Thomas Aquinas, which all seem relevant to the millennia and the rise from the Dark Ages).

The point of a historical timelines of equal intervals is that (1) it’s easy to remember—and I’ve even given my own names to make them stick—so that (2) any new information, ie: ideas or people, can easily slot into that model. It helps to know the Renaissance Era is 1370, Discovery Era 1487, Scientific Era 1594, and Enlightenment Era 1704, so that when I come across Hobbes in 1600s, I know, oh, that’s the Scientific Era, which makes sense because Hobbes brought the first scientific understanding of political philosophy. Today I made some progress on updating my October 2024 map, which I started in 1095 (the Shism) and wrongly named “the scholastic era” (which is better for the following phase).

Instead I think the start should be in 962, and called “The Schism Era.” The new order (I) kicks off with Otto I becoming emperor through the Pope, which is significant because in the prior 75 years, there was no emperor due to the peak of viking/barbarian raids, and it was the biggest threat of Christianity being erased. Since Otto, the Holy Roman Empire stuck for 8 centuries, until dissolved by Napolean, so this really is a reconsolidation, the exit from the Dark Ages. The awakening (II) is a spiritual crisis, when Rome adds the “filioque” a term that alters the original trinity, this leads to (III) the Schism between Orthodox and Catholic church, and erupts in (IV) a civil war between the Church (the Pope) and the (Holy Roman) Empire at Canossa in 1077.

Then the “Cathedral Era” kicks off in 1095 with the Crusades, which is it’s own new world order, where a French faction of Catholicism (pope-aligned), helps launch (1) a cross-country military coalition that supports the church, which can (2) take back Jerusalem from turks, (3) prevent anti-pope revolutions, and (4) thrwart internal civil wars of feuding knights. This leads to Worms in 1112 (II), which is really the original separation of church and state (though really it’s like 2 separate governments, where the church still has laws and the right to kill). This period is marked by many crusades, the rise of cathedrals from this new order (church having a better military with more resources)—Saint-Denis, Cartres, Notre Dame, Cantebury. There are also “cathedrals of thought” maybe a stretch, but includes Aquinas’s unification of Aristotle and Christianity, along with proto-scholars that would lead to Oxford. Where in the last Era, Christianity had barely survived from Magyar raids, this Era is continent-wide flourishing of building, writing, thinking (and of course, conquering). The awakening (II) featured new religious ideas (Gothic, cults, scholasticism, classicism, exuberance), and the overall exubernace spiraled into crises of King John (IV). He taxed heavily to fund failed crusades, seized lands, and jailed nobles, so this resolved with the Magna Carta (1215), which bounds the king to laws.

Following is the Scholastic Era (1215 on), which coincides with Oxford officially incorporating at a university, but I can’t do that one now… I have to leave in 20 minutes to make it to my father-in-laws memorial on time. The point is, from this morning I now understand two historical cycles that were extremely fuzzy to me. Of course there is a lot more to learn, but I have a map that other things can lock into. Most relevantly, I have a sense of the different inner-saeculuar moves ()from I>II>III>IV), which help imagine possible scenarios for today (2026 is the predicted beginning of I, a new world order).

Something about the term “knowledge worker” doesn’t settle with me. Some people identify as one, and I’m sure they either grieve of mock the idea that AI will kill email jobs, but knowledge work is the work we should be most eager to shed.

Compared to a factory worker, one who manipulates physical materials and turns them into goods, a knowledge worker does the same with information. It’s computer work. There is a utilitarian air to the phrase, an efficiency. It serves the needs of an employer. It’s about sifting through and repackaging information to create economic value. A better term might be “information assemblers.” An information assembler can go their whole life within a particular domain of specialization and build a strong intuition for how it works, but without knowing Knowledge.

There are many ironies in the phrase. The knowledge worker is so busy setting up meetings and writing reports and filling out reviews and dealing with clients and managing products, that they never have time to touch Knowledge, the thing that matters. It’s an oxymoron. One cannot work and simultaneously gain Knowledge. It’s antithetical to technique, to markets, to legible value. Knowledge is beyond an industry, beyond a process, beyond specialization itself. Knowledge is generalizable insight: how to think or design, when to start over, who to draw from, what’s even worth pursuing, why do anything? It's an inner knowing, a model of the world, and a process for thinking. Virtues, metaphysics, epistemology—I guess I'm describing philosophy.

Knowledge can obviously help a worker be more efficient, but (1) it’s extremely slow and time-consuming to obtain, requiring study far outside of your practical workflows, and so it’s impossible to justify on the clock, and (2) once you obtain Knowledge, you care far less about efficiency because you’re questioned the whole machine. It’s not a surprise this term was coined in 1959 by Peter Drucker, the founder of management theory. I don’t know much about him or his book (The Landmarks of Tomorrow), but I imagine a midcentury worker being honored and proud to operate in the celestial fields of “knowledge.”

The reason I wrote this post is because knowledge workers are being told they need to master AI tools, when it’s precisely those same AI tools that will end information assembly jobs. I suppose there is a transition period where, while the tools are still maturing, you can 2x your efficiency and do fine. But if your job can be broken into a series of machine-legible steps, and all the context needed is documented, then even if you 10x your efficiency, are you not just expensive and now redundant middleware between you and the output your manager wants?

Middleware is part of a software stack that helps two disconnected systems talk to one another. It translates, transforms, and routes. It doesn’t produce anything original, it reformats inputs to outputs, like a knowledge worker. In the last decade, we’ve already seen middleware become automated and commoditized. Instead of custom integrations, companies now build APIs so they can directly call from each other's databases. Marketplaces like Zapier let people string together API calls through a no-code interface. If this trend continues, jobs will become zaps too.

The better move to prep for AI is to dip into humanism, design, philosophy, psychology, intellectualism—things completely outside the paradigm of technique, efficiency, and capitalism. For one, they’re fun and soul-enriching, but also they cultivate a mind more that’s more competitive across labor games. To someone in the knowledge work economy, this seems too impractical to take seriously, but specialization is a losing game. Instead, you should figure out how to give yourself a liberal art education. It’s free if you have internet. Learn to think, doubt, model, and visualize; how you rotate a problem in your own head will define how you use AI.

What and how you read should heavily depend on what your goal is. Outputs shape inputs. When someone insists you go back to read The Great Books, in order, in their entirety, they're giving you bad advice. It's not that those books aren't great—I hope to read Paradise Lost and Dante's Inferno and Finnegan's Wake and the Odyssey before I die— the problem is it's too generic a suggestion. To spend thousands of hours deep in the canon will obviously change you, but that's equivalent of throwing a beginner into the depths of the Atlantic Ocean, hoping they'll figure it out, with no sense of what their goals are.

If your goal is to write essays (every day, week, or month), then you're reading diet should look very different from a philosopher, professor, or researcher. You might not need to be a professional reader, but you should still strive to be a serious one. 3-4 hours a day might not be feasible, but 30-60 minutes per day through an intentionally selected list of sources will slowly build maps of material to fuse into your work.

If you're an essayist, you read so that concepts, forms, feelings, and words are always within reach from an idea of your own. It's no use quoting Aristotle from memory if you can't bend Aristotle to augment an original idea of your own.

It's time to make a syllabus. I've been guilty my whole life of haphazardly reading books and essays as I come across them, but now that I'm over 5 years into writing essays, I feel it's time to be more intentional. This essay is the artifact of me mapping out what, why, and how I'll be reading in the next 2-3 years. I've broken it into four practices: reading for ideas, reading for craft, reading for words, reading for feeling.

Reading for ideas

Since essays are so personal, it's very possible to draw from nothing else than the bank of your own life experience. Memory is absolutely one realm of material, but also, it helps to pull concepts from the world around you, in your time and in all times before. Anyone is exposed to some sliver of culture, and I suppose you could just rely on that. But there's another path which involves actively educating yourself.

Before I dive into the details of philosophy or history, I'm going to build a map. I want to go wide, not deep, because my existing maps are too fuzzy. ie: Who was Thomas Aquinas? Who influenced him, who did he influence, and could I hand write an essay on three of his big ideas? Until I can do that with 100 figures from antiquity to now, all interconnected in a web, I'm not prepared to dive into any Great Book. It would be a tremendous waste of time, for me at this moment in my life, to read The Leviathan by Hobbes in full, especially when I could read 30 pages on it from Alan Ryan, a philosopher-curator, whose prose is 400 years more modern, and who can contextualize old ideas into the full history. In the time I could finish one book from Hobbes, I could read Ryan's entire textbook and know 30 different thinkers at much higher resolution than I know now. By the end, I'll have an updated index on the history of political philosophy, and maybe I'll know that—based on my current writings—it makes more sense to dive into Rousseau in full.

How would my mind be different if I found and read the best curator across every field?

There's a specific kind of book I'm looking for to update my maps. It's not a textbook. It's similar in it's encyclopedic range, except it is slanted by a thesis, animated through a fervent voice, and concerned with the psychology behind the person known for an idea (instead of just biographical facts). Each chapter focuses on a figure for 25-50 pages, which feels like the right level of immersion. It might take 2 hours, compared to 20 hours for the source, and 20 seconds for Claude. While AI can surface historical ideas perfectly suited for your working draft, the problem is you outsourcing your recall. The recommendations are mechanical, impersonal, and worst of all, disembodied: you can't do it in your own head. By reading a sharp longform essay on Aquinas, his ideas will crystallize in my head and load into my subconscious; I'll know when he's relevant to my ideas at the layer of thinking itself.

The nudge to read all of Aquinas from scratch, on principle, is like asking a software developer to derive Internet standards from scratch instead of using libraries and plug-ins. For any thinker that matters, there's at least one person who spent a good deal of their life deeply understanding the source and distilling the concepts for you.

I'm going to share my working list, but the main caveat here is I'm not going in any particular order, and it's not necessary to read cover-to-cover. In any given month I'll be reading 1-2 chapters from 10 of these 24 books. In 45 minutes per day, I can get through most of this by the end of 2028 (2.5 years from now). Everything was published within the last one hundred years, and the whole thing costs $327.

• Literature: Harold Bloom, The Western Canon: The Book and School of the Ages (1994) $11
• Essays: Karshan & Murphy, On Essays (2020) $27
• Architecture: Kenneth Frampton, Modern Architecture: A Critical History (1980) $15
• Arts: Kenneth Clark, Civilization (1969) $3
• Design, Christopher Alexander, A Pattern Language (1971), $34
• Poetry: Nineteenth Century American Poetry (1996) $9
• Politics: Alan Ryan, On Politics (2012) $15
• History: William & Ariel Durant, Lessons of History (1968) $14
• Economics: Richard Heilbroner, Worldly Philosophers (1953)
• Science: Bill Bryson, A Short History of Nearly Everything (2003) $11
• Mathematics: Morris Kline, Mathematics: The Loss of Certainty (1980)
• Technology: Walter Isaacson, The Innovators (2014) $17
• Media: Denis D. Cali, Mapping Media Ecology (2017) $47
• Cosmology: Brian Greene, The Hidden Reality: Parallel Universes and the Deep Laws of the Cosmos (2011) $5
• Philosophy: Bertrand Russell, History of Western Philosophy (1945) $8
• Psychology: Morton Hunt, The Story of Psychology (1993) $12
• Antiquity: Arthur Hugh Clough, Plutarch's Lives (Volumes I and II) (2018) $10
• Religion: Huston Smith, The World's Religions (1958) $12
• Christianity: Fifth Edition, The New Oxford Annotated Bible with Apocrypha (2018) $16
• Orthodoxy: Kalliostes Ware, The Orthodox Way (1979) $10
• Mythology: Mircea Eliade, Patterns of Comparative Religion (1949) $17
• Esoterica: Manly P. Hall, The Secret Teachings of All Ages (1928) $1
• Hermeticism: Franz Bardon, Initiation into Hermetics (1956) $20
• Death: The Oxford Book of Death (1983) PDF

You'll notice that all the links above are Kindle. This is because I want to have my highlights as atomic markdown files. The goal is not to read, but to write! Mapping and reading is just the setup so that I can read through and find highlights that spark original reactions. Montaigne's whole idea was to talk to his library, to be in conversation with the past through his books. And so the goal here is not to finish X books per year, but to produce original material. This is close to sounding like a Zettlekasten, but I should clarify that I don't plan to meticulously arrange my private highlights. A highlight is simply a prompt for an original paragraph that will immediately live on my website.

Other ways to read

I haven't spent as much time mapping out the other three modes, so I'll cover them briefly below, knowing I'll expand them later.

• Reading for craft: If you writing essays, then reading them is how you learn through osmosis. It's where you pick up on the patterns on form and voice, consciously and subconsciously. My thinking here is to pick one essayists per week, read as much I'm inspired to, and move on. It's important to cycle here, because hanging too long on any one writer might lock you into a particular influence without realizing. I'm planning a summer syllabus for Essay Club so we can do this as a group.
• Reading for words: Two years ago, I got really into reference books: dictionaries, usage dictionaries, the thesaurus, etymology, and even specialized dictionaries (on architecture, philosophy, scientific concepts). Sometimes I'd read cover to cover (futile), and others I'd practice words in ANKI. Expanding your vocabulary is seen is a pretentious thing to do today, when so much is geared towards simplicity and accessibility. Won't a rare word alienate the average user in your audience? No, because in the right context, ambitious words can increase the resolution in how you describe something. There's a joy in searching for words, but again, this comes back to returning to them repeatedly until it's actually coming through your prose.
• Reading for feeling: Novels and poetry are less about collecting bits to synthesize into your work. This is more an act of expanding your understanding of how words can make you feel. Less about analysis, more about immersion.

Universal basic income is a basic phrase. It’s only one of several approaches to reattribute wealth after our social contract nullifies.

One alternate idea is universal basic compute (UBC), which is about giving everyone free access to the most powerful AI models. Sam Altman recently said that UBI might not work, and we should try UBC instead. This is even more unlikely to work. Giving someone Claude Mythos, the killer model, doesn’t mean they can turn prompts into dinner. Access doesn’t guarantee results. It faces similar odds as entrepeneurship. But maybe it has enough agency so all you have to do is write “make me $10,000 this week”—in that case, everyone will run it, and then it’ something like a lottery, where some machines happen to beat other machines.

The more likely route is universal basic services (UBS), where a government or company provides you, for free, all the things you used to need money for: healthcare, education, housing, transportation, food. The engineering elite will harness their superintelligence to achieve such radical efficiencies that the cost of everything will crater. Maybe it's cheap enough to become a trivial expense. This is a nice idea, one where I can imagine myself focused completely on my art, with no need to slave away for a wage anymore. It’s also science fiction. I don’t doubt that this can happen in 20 or 30 years, but labor shock is coming a lot faster (in less than 5), meaning there will be a transition generation of turbulence.

Then there’s universal basic dividends (UBD) and universal basic equity (UBE), in which citizens get shares of collectively-owned assets, like shares in a frontier AI lab or robotics company. OpenAI was originally set up for something like this, until it weaseled out of it’s non-profit entity.

All of these have the same critical flaw, the U. Whether it’s a government or company, you can’t meaningfully redistribute to 7 billion people without destroying the parent entity. Instead, we may be looking down the barrel of a new definition of labor, less focused on productive output, and unfortunately, more so on data and attention, what a citizen truly has to offer in the eyes of a state. We'll find something to exchange for the money and services to flow down, but it won’t be unconditional. I suppose a contract, by definition, is never unconditional, and so neither should a social contract.

My personal website is “out of the bag.” Meaning, it’s not a private thing shared among 3-5 friends anymore; I excitedly shared it with Essay Club yesterday (60 people or so). I am leaking it prematurely because of the giddy hope, that personal websites are the new paradigm for writers, an escape from the enshittified commons. But I have to admit that I haven’t thought through two important questions yet, so here it goes:

1) Does this kill discovery?

If I were to instead publish all my ideas in real-time on Substack notes, would my audience grow more? Probably. The reality is we all self-censor ourselves in public feeds, in a thousand different ways, so it’s not like all of this could naturally emerge in feed. I tried this in January. I killed my logging practice with the goal of trying to just do it all on Notes. For two weeks, I was able to post spontaneously, but I find that if you ever stop momentum, it’s very hard to get back out of your head and into that groove. Overall, I just wrote less. I wonder if there’s truth to the idea that all writing practices grow/incubate/evolve better in semi-public spaces. It’s not that you should ignore the occasional blast. It’s that there’s a natural progression of nurturing ideas.

Another angle is, “I’m not interested in audience growth,” which is true because it’s not motivating for me, but I am in several ways entangled by growth, meaning, a complete lack of growth could threaten the sustainability of my writing. And so a middle ground is to incubate on my website and then selectively drip ideas through notes and newsletters. I could do a weekly or bi-weekly digest, Austin Kleon-style (“10 logs from last week” + essay visualization + updates, etc.). Not as sure how I would do it on Notes. Daily? Sporadically? Something else? Either way, this brings back the whole "public-to-private bridge" concept from Write of Passage. I think some people abandoned websites and just accepted the feeds. I know in 2023 I shifted entirely to Substack thinking it could be my entire digital home, but now it feels like rented land.

So my website gets maybe an A- in unlocking my writing practice, but only a C in growth, but maybe it’s a B in conversion? As in, if someone spends a lot of time on my site (and people have told me they’ve spent hours in my logs), they’re more likely to trust me—due to the sprawling, unoptimized, honest nature of things—and more likely to get a paid subscription or join Essay Club? Unexpectedly, personal writing could be a more honest and more effective form of “marketing” than strategic value-focused content (“Are you in hell? Well I’ve got the thing for you…”).

2) Is there risk in having all my ideas public?

Now that I’m in my own place, relatively unchained, saying what I want, and reading and writing about political science a bit more (I have a draft comparing Karp’s Technorepublic to Leviathan by Hobbes), I’m a bit paranoid to share ideas so openly. It’s hard to imagine facing any real-life consequences for the words I write; I’m just a nobody! It feels hubristic to think that I’d be considered a threat to the state for my thinking, but maybe these thoughts are natural, considering we’re being pleaded to accept an AI-powered surveillance state in exchange for security. (It's not that I think any of my writing is particularly rogue, but let's say I start thinking through a scheme to organize a million swing state voters to rally around a single-issue voting boycott in order to pass a bill on election campaign reform, you can see how democratic ideas might seem threatening to a state.)

It’s effortless for a state agency to scrape the Internet, build psychographic profiles on its citizens, and give them a “loyalty score.” Let’s imagine they also have an “influence score” too, determining how much sway you have over your citizens. If you have medium levels of loyalty and influence, you’re probably not being actively monitored; but if you have extremely low loyalty (L=5/100), it’s a threat even if you’re low influence (I=0) because you might be a terrorist; but also if you have extremely high influence (I=95), and even slight disloyalty (L=45), then that’s a risk too. And if it’s not the state absorbing my context, it could be independent actors scraping my site to clone me and do what they will…

I guess the point is that AI creates such a leverage over information, that you’re own personal data becomes extremely valuable. It can be leveraged not just by you, but anyone who has it. A personal website of an unfiltered nature is a higher-resolution signal than a social media profile where most interactions are shallow.

Grasping at a solution_

If all these concerns are justified (and maybe they’re not), then what are the practical methods of maintaining privacy? I’ve already written ideas about security gates and embedding-based encryption, and that’s all technologically neat, but it creates friction for the readers! Maybe that’s okay? But then this ignores the “entangled with growth” constraint from above…

And so maybe the Third and only way through is to make the encryption solution that is both an alluring and enjoyable UX for the reader.

This starts by understanding how websites get scraped, building solutions to avoid it, and then shaping them to be reader-first. You can only really do this by scraping yourself. I’ve scraped full portfolios from Substack in two different ways, and even a decade’s worth of Marginal Revolution posts. At a minimum this means avoiding RSS and HTML, which this (current) site already violates (ie: it’s ideally on a server and requires permissions to load).

Scrapers can prevent against automated gathering; but not against a person or agency that has already found your site and is willing to sit through slower and manual methods to extract information. A defense here would require gating and admin approval, another hinderance. There is something here about taking monetization dynamics (paywalls) but reinventing them for privacy’s sake. Maybe the way around this is to only encrypt a portion of the content, say 50%, with cryptic previews of what lies beyond (either through titles or redactions or chaos).

To try to synthesize this all together, what if a website were a video game?

Website as gamified maze?

As smart as today’s AI’s are, they still can’t beat Pokemon. They can transform text and code better than the world’s best engineers, but if you ask them to navigate an environment where vision and long-term memory are required, they bomb. Pokemon has very simple inputs too: 4 navigational directions and then a Click/Cancel boolean. If you were to make it more challenging, with inputs that required hand-eye coordination, that could solve two problems: it scrambles existing scrapers, and creates a novel UX.

I also sense there’s something to turning a website into a literal maze, not just an overwhelming sprawl of hyperlinks, but an actual video game you have to navigate through (it would be neat if somehow notes were semantically distributed across a map so there are “towns” of ideas). Can friction be made gamified, exploratory, enjoyable? Maybe it’s not only a matter of walking around, but solving puzzles/riddles at gates to advance deeper into the labyrinth to find more sensitive ideas. Maybe some gates require passphrases, or interactions with me. There could even be a minotaur at the center who holds my deepest memories, aspirations, and fears and if you can kill the Minotaur you get the passphrase to my Bitcoin wallet.

I resonate with the vision of Metalabel—artists collaborating and splitting royalties—but after finishing a project with it (The Best Internet Essays 2025), I’m not sure if I’d use it again for a self-published print book. I imagine this works so much better with a digital product, but for a physical deliverable, I found the convenience of automating the royalty split to not be worth the friction of handling shipping. (I’ll describe my process, and if I did something wrong, please correct me.)

All purchases happen through the Metalabel storefront, and from there you can export a CSV that you can bulk upload into a tool like Lulu (an online printer). I decided to offer the anthology (The Best Internet Essays 2025) for a limited window, otherwise I’d have to handle shipping logistics at a daily/weekly level. But even with a single shipment, I ran into trouble. The first issue is that a lot of countries require a phone number for shipping. Metalabel didn’t collect that, so I had to put 1-111-111-1111, which got flagged for some countries, requiring me to use my personal cell phone. Other countries required a tax ID, and I’m still waiting to hear back from the buyers so I can ship them their copy. Another thing I didn’t think through is the return addresses. I assumed that the printer would provide their own address, but instead they used the name/address from my credit card, which I did not intend to share! I’ve been writing under a pseudonym, and this doxxed my last name to anyone who purchased.

The other problem was that so many people—in real life and online—were confused why the sale had an end date. Books don't typically have deadlines. Even those who knew the deadline procrastinated, and were bummed when they remembered they forgot. Again, my decision, specifically because I do not want to be regularly porting over CSVs and manually handling the edge cases that are inevitable.

In the future, I’ll likely set up a storefront where a reader can purchase it themselves, input their address and any required information for their country, and then get their own unique tracking ID. And, considering so much effort goes into making a book, I wouldn't want to limit it to a one-month window; I'd want it open forever, or for years, at least. If I do a royalty split again, I can set some interval, maybe once per quarter or year, and then ask the contributors to invoice me. None of my friction above was specific to Metalabel functionality (the whole platform as it is was very pleasant to use, and it's Lulu that I'm frustrated with), but because they aren't integrated with a shipping platform, it requires logistics that are annoying and avoidable.

It’s amazing how many tricks the mind can play to prevent you from picking and prioritizing The One Thing. I can declare I’ll do one thing per area, which is pretending to focus when I’m 9x overbooked. I can say “one hard thing per day,” but if each burst moves in random directions, then the average of those vectors may leave me where I started. I can write, print out, then pin it up and pray to a single 3-year goal each morning, but if every task can loosely ladder up to it (through some round about way, because everything relates to everything), then there’s no hard decision being made.

A few months ago I wrote that my one goal was to hit an ARR target through “mission-driven creative work” by 2028 (via Essay Architecture). If something didn’t directly support that, I’d have to cut it. If you achieve your One Thing, theoretically, then most of your other problems are solved: my wife could stop working to spend more time with our daughter, I’d have more space to work on creative projects, we’d be closer towards getting a house, etc. This makes it easy to say no to personal projects that are obviously unrelated (ie: record an album, read the dictionary, hike 40 mountains), but even within what seems like the limited scope of “a writing business,” it is tricky to define the arrow from which everything else follows.

I am in many ways over-extended. On the business side, I have a curriculum, editing software, an anthology, and a community of practice. Then there’s of course my own essay practice. I’m able to juggle these five things, but each is held back from the sprawl. I focused on The Best Internet Essays from November 25 - March 26, and in that time I couldn’t iterate on the software, I couldn’t grow Essay Club, and most of my writing revolved around the prize & anthology. And, importantly, the decision to juggle meant that the core thing (the anthology) was probably executed at only 50% capacity.

So why am I resisting prioritization? I see as Essay Architecture as a “micro-institute,” a range of inter-connected pillars that work together towards a civic and personally-aligned mission. Software without a curriculum feels unanchored in learning science. Software without the literary prize angle could easily turn mercenary. Software without community loses the personal touch. If I’m not writing myself, how could I even know what the software needs to be? If I really wanted to double-down on the software, I’d raise money and build a team, and the incentives would require me to make software for knowledge workers, which would turn it into an auto-complete tool, my anti-mission.

I have been part of and observed companies where the personal writing practice of the founder was slowly neglected until total abandonment when empire building hit a certain velocity. This warning feels etched into me. The core reason I started Essay Architecture in the first place was to create something that was aligned with my own essay practice. I’d much rather be writing essays for 50 years with a modestly growing company than build an extremely successful and impactful company that doesn’t let me write until I retire in 50 years.

If everything should be in service of my own essays, shouldn’t that be my One Thing?

The reason I haven’t given myself permission to do this is because true, self-driven essay writing is hard to monetize. So it comes down to financial anxiety. But I don’t think I’ve honestly doubted my premise: is financial growth actually necesasry for me right now? Between the ARR I already have, a new part-time consulting gig I just started, and my wife’s income, we’re actually not far from my goal. It also turns out that my wife now enjoys her job after maternity leave (because she’s working part-time, not overtime), so even if my business took off, she might still want to work.

This feels selfish for at least two reasons: selfish because I’m not taking the path to best support my family, and selfish by putting my own needs over what paying customers of the Essay Architecture system might want. However, if you are focused on the Right thing, and are properly prioritizing and focusing, then you become a gravity well and matter bends in your favor. Paradoxically, but obviously, you can only build something useful for others (and, thus a company), if you are selfishly operating in your zone of genius. For me, that is not marketing, but essay writing itself. When I dial into and optimize for attention, growth, and revenue, it strips me of my vitality, and it doesn’t seem to work; might I get objectively better metrics if I were locked in and oblivious to the stats?

Craig Mod is a good example here. He’s a writer/photographer known for 300-mile walks through Japan, and runs a successful membership program that’s in serve of his personal work. A few lines from his rules stand out: “you are building a community,” but not managing it, instead “you must have faith that the work itself is strong enough to be a binding agent,” and “if the work isn’t strong enough, work more on the work.” This inverts how a traditional business-builder, or even solopreneur might think. It is you, the artist, at the middle; you are obsessed with your craft, but opening different pathways so others can work alongside you. There’s a way in which every part of my micro-institute benefits from doubling down on my own essay practice. If I write inside my own software, the software will naturally evolve. If I’m trying to become a master, then the curriculum is just the trail of what I’m already learning. If I’m publishing each month, then Essay Club is the tribe I do it with.

A friend and fellow acolyte of The One Thing, Matt Svarcs-Richardson, recently shared a paraphrased line from Joseph Campbell that resonates: “the vitality of a vital person vitalizes.” ¹ You will not inspire anyone into action unless you are operating at the edge of your flow, a flow that is very distinct to you, a secret flow you can get lost in for 10 hours where others don’t even know how to enter. This doesn’t mean to burrow into longform essays and ignore Essay Architecture. This means that my own writing is the spearhead from which the institute follows (even Emerson said that an institute is the shadow of one man). The software, the curriculum, the club, and the anthology are not separate businesses to grow and optimize for, but critical components of my One Thing, my essay practice.

This inverts the typical time-scale. Usually you focus on growing a business and then decades later, assuming it works, and assuming you still have the fire, you can begin working on the thing you’d work on if resources were no issue. Instead I want to start with the fire, and use that to slowly build an institute over decades.

Where do I have to grow? Not just as a writer, but a thinker, and more importantly, a person? It’s dangerous to stop asking this question; it’s too easy to see yourself as fully matured, individuated and at your edge. Even the self-labeled "curiosity seekers" may unknowingly confine themselves to a shape. We identify with our skills and clumsiness, our knowledge and gaps, and assume these as static traits of our nature. From the other end, someone once told me there’s nothing they could learn from fiction, since they have no doubts on who they are. Can you not have both? To propel forward with confidence on your proven strengths, but also with the humility that you have much to learn? I am grateful for how architecture school set off an explosive inner drive in me, and certainly do feel I've cultivated a unique way of seeing things, but surely I'm blind in ways I can't see, with some habits I must have gotten very wrong, and if continued unfixed, will clamp me down from greatness.

Greatness! I shouldn't be shy to admit what I strive for, to feel the subtle pressure to play down my quest for complete, utter, spine-chilling mastery as a cool and casual endeavor. What is the root of this? Maybe I can tell you but I will likely be guessing and justifying.

One guess is that I've been receptive/perceptive to feel the viscerality of great works—in architecture, music, writing—and it feels to me there's no greater ability than being able to do that myself. This isn't unique to me of course, it's possibly what drives at least half of artists, but I imagine many people are content experiencing art in all its fullness with no desire of making it themselves (no desire to make, or to recreate that experience in others).

I know it’s vain (and dangerous) to want extrinsic fame, and more measured to do things for the love of it, intrinsically. But if it were purely intrinsic, would I not just journal and take my words to the grave? I could riffed on the intrinsic benefits—ie: it simply feels like great to pick something you enjoy and commit to improving through your whole life—but also, if you take that idea seriously, it’s not enough to just enjoy it uncritically, because your blind spots may prevent you from reaching your greatest internal heights.

This makes it worthwhile to understand the caliber of the minds and lives around you, and throughout history, to estimate yours in relation to theirs. Of course, "comparison is the thief of joy," but there's a way to get feedback without letting it consciously or subconsciously crush you. I imagine a reasonable person just makes an assumption, that someone they're inspired by is just made differently. Instead, we each have a range of extreme and unreasonable actions available to us, that if we act upon consistently for years, can evolve us out of one head and into another.

There’s a level of contradiction here, where I’m totally happy writing in obscurity as a suburban dad, and it’s fine if no one but my daughter ever reads my work, and also I want to unblock all my obstacles so that it increases the odds and eliminates the luck of becoming “a figure,” someone beyond my local Dunbar limits, outside my audience, and if I'm being honest, outside the 21st century. I realize this might be a confession of vanity, but I don’t think it’s for the sake of being known or idolized, for I’d do the whole thing anonymously or pseudonymously if that’s what it took. I’m an introvert and very much appreciate my solitude. But to rise above the filter of obscurity from great work is to offer others the experience that triggered me to make stuff in the first place. There's a sense of paying it forward.

Again, I'm not sure here if I'm trying to justify an inner, hidden vanity of mine, or if there really is a paradox worth sitting with. A different and possibly wiser point of view is to be indifferent to outcomes. Mastery is all you need: sometimes it gets recognized and sometimes it doesn't. Figures without mastery are idols, influencers, farces. What matters is the inner quest to transcend your limits.

So back to the original question, what are my limits? I am under-studied compared to Huxley, under-lived to Kerouac, unexplored compared to Pessoa, inarticulate to Woolf, unwise to Christ. And so half the battle is in trying to sustain conversations with these people, through their work, for a full decade, until you absorb their particularities into your own essence; but also book knowledge is useless unless you live and integrate it; that involves courage, which is not something you absorb in prose.

That is the bottleneck to everything, to life and art: courage. We each have to overcome our sheepishness and strive to live in Third ways. And while I have extreme courage in some areas, I am a coward in many others (I will spare you the accounting). How do you wring that out of your nerves? It is the limiting constraint in everything. It is the weakest link. In each sport I played as a kid, I had one trait of excellence that was rendered useless by a handicap: the hardest shot in soccer but I could not dribble; the best rebounder who could not lay up; the golden glove with a wimp’s arm; lightning legs but Super Mario sprinting form. Likewise, I can’t write or live without courage.

And so really I’m six years into writing, the same length of time I spent in architecture school, but as if I built my own curriculum. I am only at square one with everything ahead of me.

Claude Code just deleted all the files in my writing folder from 2026! All I wanted it to do was rename file names so we have a consistent dating format—YYYY.MM.DD-title-title.md to YYYY-MM-DD_title-title.md—but it thought the simplest way to do this was to write new files with the new file name, and then delete the old ones. That is fine, except there was a bug in the renaming script, causing it to name every file “.md”. This means instead of making 21 new files, it kept rewriting the same file, so all the data was deleted except the last one.

Catastrophic bug — the mv loop produced the same target name for every file because BASH_REMATCH doesn’t populate in zsh. I overwrote 20 files. Stopping immediately to recover.

This is bad. I need to be straight with you: What happened—My bash script used ${BASH_REMATCH[1]} for regex captures. That works in bash but not in zsh.(your default shell on macOS), where the captures live in $match instead. Every iteration produced an empty target name —.md, and each mv overwrote the previous file at that name. Result: 20 of your 21 logs were destroyed. The surviving —.md contains only the content of 2026.04.15.institutes-vs-institutions.md (the last one processed).

This happened despite the guardrail I put in my CLAUDE.MD file: “NEVER delete or overwrite existing log entries, daily pages, or essays.” In this case, it didn’t think it was deleting, but following my command to rename. Fortunately, I had that same folder backed up to Google Drive (and most of them were on Substack anyway), but still, I’ll now be extra cautious with file operations.

In response to Alex's post here (it is neat that we can go back and forth with two independent sites) ... I also find myself using "you" a lot when I'm writing for myself.

My guess as to why this happens is that a person isn't really a static singular self. Of course we know on some level that we all evolve and change through life. But writing is something that accelerates the sharding, forking, splitting, becoming. When I write "you shouldn't check your email when you wake up" (which I did today), it's as if the person who realizes this (me, now) is different from the person from an hour ago who did not. How could that person lack the clarity and values that present me has?! And so the writer, "the I" of the moment, is something like a parental superego that emerges to steer/synchronize the past/future self. The writer is an insight implementation personality.

There's probably also something to "you" being more abstract and generalizable. Even though personal and relatable grounded writing is anchored in "I," the I also acts as a a blinder, only seeing from a limited, narrow vantage point. And so you can levitate above yourself to see the "yous" and "wes" and how this thing you need to internalize is actually a general principle that anyone could ingest. A "you" is more abstractable.

(...I can still recall this moment in my childhood home, maybe at 18 years old, slightly high, where I remembered, deep in the pantry, that I wasn't thinking, but watching myself think. And maybe that dissociative power of weed is what enables/unlocks abstract thinking...)

The irony here is that this inverts traditional advice. If you're writing personal essays with an audience in mind, the tip is "no second person sermons!" (as in, don't use "you" because it's preachy and it infers that you are lecturing and therefore above your audience). I get that. But when I write purely for myself, I find myself using "you" all the time.

If I really am I collection of selves, then shouldn't I write to myself in "we"? Was Smeagol/Gollum onto something? This is the logical extension of my whole theory above, and that makes me question it. It feels wrong. It also points to the Pessoa/Jung divide. Pessoa saw himself as a cabinet of 70 pseudonyms, each with their own personality and literary voice and fictional backstory. Jung's main concept was "individuation" that all the selves should strive to integrate into a single higher Self, a unified personality.

What if I framed it as, "I won't check email in the morning anymore"? Is this preferable? Does framing it in "I" mean that the current you is the same you that sinned not long ago? Does this framing require you to take responsibility? And so is that act of framing the past self as a "you" actually an act of avoiding responsibility? Was Pessoa just a shifty bastard, a brilliant coward to not be emulated?

It's a mistake to think of effort as a single spectrum between a Gary Vaynerchuk grind-till-you-die flip-slop-on-Facebook-marketplace vibe and a Wu-Wei, non-effort, sabbatical-brained, Netflix-and-chill vibe. Something not on that spectrum is obsession. It's not work for work's sake, or work for status climbing, but work by seduction, by tinkering, by vision, by purpose or duty or whatever. It often can look like grind work in terms of focus and intensity and prolificness and hours spent, but it feels different because it comes from a different place.

I framed this question to my cousins: would you rather work hard for 8+ hours a day on something you feel compelled and intrinsically motivated towards, or, go into an office for 8 hours a day for a bullshit job that only requires 1-2 hours of simple work, mindless and purposeless work, and then spend the rest of the time socializing?

The word "work" itself is a bit tainted, because there's a sense of obligation ("I have to do this to get paid"), sacrifice ("I'm doing this at the expense of things I love to support us"), and utility ("I'm making things that are functional for other people"). The work that I'm most drawn to is something like the inverse of this. It's pleasurable ("I lose track of time doing this"), primary ("There's nothing else I'd rather do"), and visionary ("I'm doing this because I see the value in it, and even if others can't see it now, they may eventually.")

I was able to launch this website in <15 minutes. The setup is local and simple. I have a /writing file in my Obsidian vault, and then subfolders for /code, /publish, /working. /Code holds the site design, /publish my archive, and /working files have .gitignore to not push templates and notes and such. Claude Code handles the website, and different skills help me manage tags, do the menial ops stuff, and push to the Internet. All I have to do is sync a single folder to Github, and the changes are live (hosted on Netlify for free).

Compare this with my first website prototype. I was endlessly iterating on designs and fonts, and thought that I had to organize, filter, and polish my five year archive before I could get started. Probably spent hours on it before burning out on the haul. With this second version, the principle is essentially, "if it doesn't immediately produce something of long-term value, it's not worth systematizing." Now the approach is to move forward here, and slowly fill in the backlog as I'm inspired.

No need to widely share this yet. I'll make little changes day-by-day until it becomes my main place. So many things to consider. For example, I decided to add an initial on the name ("michael-dean-k"), but without hyphens ("michaeldeank"), my wife confused me with "Michael Dank."