Not long after I announced my own $10,000 essay prize, coined as the “world’s largest open1 essay prize,” Elon launched his own: $1,000,000 for the best article on X. Immediate deflation. I did not expect the world’s richest man to suddenly champion longform writing. A 7-figure essay prize was a ridiculous goal of mine, one I thought would take a decade to exist, but for the equivalent of 14 cents in Dean-adjusted-dollars, he launched it with the care of a whack. After the shock faded, I tried to be open. This is historic, right? An unreasonable sum of money will be granted to, not an essay, but at least a written thing over 1,000 words, a piece to “move culture,” untangled from gatekeepers, open to anyone (anyone who is a premium X subscriber…). So, I did what any fellow essay-prize host would do and burrowed into the terms and conditions, and unsurprisingly the altruism breaks down the further you dig.

The first thing to poke into is the criteria: after writing a 25,000 word textbook on what makes a good essay, and maybe another 10,000 on how we’ll determine the winner, I knew the WINNER DETERMINATION clause was where the real architecture of the prize lived. I found 16 words, summarizable in 3 points: originality (undefined), spelling (what?), and “Platform engagement (i.e., verified Home Timeline impressions).” I.E., did it go viral? Despite the terms saying “no politics,” that absolutely seemed like the deciding factor. The winners each had an Elonic nature: on the corruption of Deloitte’s government contracts, on COVID scams, on tariffs, on Minnesota. This is not abnormal though; the typical prize is after all just a scheme to promote an agenda, not writers.

However, most prizes aren’t openly evil enough to tell you they intend to steal from and destroy their own contestants. See Term 3, 118 words, but compressed here to break the shield of legalese:

“By submitting… [you] irrevocably grant… X and its respective parent companies… the right to use Entrant’s… likeness, voice, persona… (collectively, ‘Personality Rights’), in whole or in part, in perpetuity, throughout the world… for editorial, advertising, trade, promotional, and commercial purposes… without further notice or compensation.”

Similar to how the mafia operates through mattress storefronts, this looks like data acquisition dressed as patroning the arts, a scheme to train Elon’s xAI but veiled as a technoliterary prize. It’s also a bargain. OpenAI and Google are paying $60-70 million per year in licensing for trillions of unstructured, bot-infested words from Reddit. Now, here, for roughly $2.17m or so (there were bonus prizes), xAI is getting tens of millions of words of novel, human-crafted, engagement-ranked content—the exact thing you need to fine-tune a frontier LLM.

I share this to help frame a question that’s top of mind—now that The Best Internet Essays 2025 is shipped, and Essay Architecture is done with its first loop of projects (a textbook, a library, a club, an app, a prize, an anthology), it feels time to cohere this into a business—: how do you grow and sustain something that is actually mission-driven and incorruptible by the market?

Mission statements are usually a farce. After merging with SpaceX, xAI’s latest mission statement is “to build a sentient sun to understand the Universe and extend the light of consciousness to the stars!”—beautiful, but to colonize space, they first need to colonize this planet’s attention. To “elevate the world’s consciousness,” WeWork needed a few real estate scams. To “bring the world closer together,” Facebook needed to psychographically profile you and sell your data to foreign governments. When you squeeze a lofty ideal through the narrow pipes of TAM (total addressable market), TUM (total user milliseconds), and CLV (customer lifetime value), the mission doesn’t just die, it risks becoming a wretched inversion of itself: an anti-mission.

If my innocent mission2 of “let’s use technology to reinvent how we teach writing and to help discover great essays” wasn’t earnest, it could easily be twisted into “let’s steal from writers to create autocompleted slop for professionals who don’t have time to write and probably hate writing anyway,” because that’s where the money is. That’s where the market leads if you willingly blind yourself. Techniques can be spun towards many mercenary ends, but the thing to never compromise is telos, the purpose behind whatever you do. Personally I’d rather become a great essayist/teacher with a modest company that sustains me through life, creatively and financially, than a constipated aspiring unicorn with a hyperscale slopcorp that contributes even slightly to the slowrot of everything.

I think what I’m trying to build is an institute. I see this as an entity that exists to serve a particular mission, and it inverts the many modes of the growth-centric creator (contributions not content, ecosystems not niches, members not users, legacy not liquidity). The thing is, an institute is usually supported by endowments, donations, foundations, tuitions, grants, exits, and such. I wonder if an AI-enabled solo-operator can now have the civic impact of what used to require millions of dollars in old money.3

The meta-mission of Essay Architecture is something like “use AI to protect the essay through the age of AI.” It is both poison and cure. A friend called this “mithridatism,” a practice from a paranoid ancient Hellenistic king, who self-administered small doses of poison to protect himself against a lethal dose.4 AI will probably be the largest ever force of institutional collapse, but also it enables us to rebuild micro-institutes that outlast the ones already falling. It’s all about knowing the limits and edges, where to use it and when to avoid it. What is worth building towards?

Some more thoughts on institutes:

Updates and announcements

I’m starting another newsletter, a development blog that shares (1) new features and prototypes for the essay editing app I’m building, and (2) the musings, mishaps, and epiphanies of a writer-builder. If you’re interested, just sign in to the Essay Architecture website (updated on Friday BTW).

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(An example of something I’ll be shipping)

Some reading recommendations:

In the spirit of trying to keep up with writers on Substack, I figured I’d try curating some of my favorite reads published from the week:

• The Kinds of Short Stories People Really Want to Read by

• xerox’d flowers by

• I need whimsy but I also need to be taken seriously by

• A Baudelairian rube strolling down a small town sidewalk by

• Reading is magic by

• AI Populism’s Warning Shots by

• Every Resource I Use to Educate My Kids by

• How to Walk Through Walls by

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Other notes

Footnotes:

I’ve written three posts about this anthology now, but if you only read the subject lines, you might not know I’m selling a book. So, final call! It ships in 3 days, on Monday, April 6th around 5pm ET.

The Best Internet Essays 2025 is a pocket-sized paperback of 13 essays, each written in and about the year. It features the finalists of an essay prize, and each piece went through another round of edits to make them even tighter. Consider this a mosaic of well-crafted immersive experiences to make sense of our times. It’s $29 and 100% of royalties go to the writers, the judges, and the 2026 prize pool. Let’s make this an annual experiment.

This is a limited edition print, so if you’re interested you should order it now before the weekend slips away.

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I’ve always heard that creating and self-publishing a book is an all-consuming ordeal, and now I can appreciate it first-hand. Not to mention, the process here was atypical. Shifting between software and operations and editing and graphic design (all while becoming a parent!) was exhausting, but well worth it. It’s been 7 months since I first announced the Essay Architecture Prize, and I wanted to pull together all the essays that tell the story of this project’s evolution:

1. I’m giving $10,000 to the best essay of 2025, announcing the competition;

2. Essay Architecture (Table of Contents), a textbook on the criteria;

3. What’s it like to live in 2025?, the prompt;

4. $9 essay coach, the feedback tool;

5. Quality is the transcendence of categories, our judging process;

6. Winners of the $10k essay prize, announcing the book;

7. Human-shaped sensemaking, the theme of the anthology;

8. We are big floating heads looking for our bodies; a chat with the winner.

The final test print came in last night. I’ve read each of the essays several times by now, but I’ve yet to read it cover-to-cover, and so early tomorrow morning I’m going to walk over to a park and take in the full experience.

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“We’ve become inverted headless horsemen: big floating heads, drifting and disembodied, restless and searching. Looking for our bodies. Bodies that have been taken from us. Bodies we lost somewhere along the way in the big promises of convenience and what actually makes us happy.”
—Tommy Dixon, Scrolling Alone

After 3 hours of talks, a 28-part email exchange that veered between letters and logistics, and building an app to analyze his 5-year backlog, I bring to you an essay about Tommy Dixon, winner of the essay prize I recently ran. It would be futile to synthesize a whole person into a short essay, so I decided to focus on one bit: floating heads. It’s a fun image, centuries-old, and yet more salient than ever.

The theme behind the metaphor, embodiment, has been poking through Tommy’s writing for years. “Scrolling Alone” was originally published in October of 2025 but it makes sense as the latest installment of a series. It was the follow-up to his 2024 essay, “the end of our extremely online era,” written from an off-grid cabin in Newfoundland, sitting on the floor, hooked up to a solar panel battery, clearly striking a nerve with 21,000+ likes. And that original essay is part of a cluster of works, all around rejecting the pace of Internet life and becoming more rooted, all written in a 10-month stretch. You can sense the theme from the titles alone: “slowness as an ideal,” “Be an animal,” “surroundings that speak of enchantment,” “Where to live,” “Building the Log Lodge,” “Real Life,” All of this came after Tommy committed to writing full-time, after rejecting a job on Wall Street, the natural conclusion of his finance degree. From essays like “workaholic,” you can tell he’s an analytical guy trying to get off screens and out of his head, into his body and a more analog existence. He told me a line from his friend, a line that seems to sum up the quest he’s on: “the biggest distance in the world is the distance between your head and your heart.”

Something surprised me though. Considering essays have been core to Tommy’s journey, and considering he’s so intentional about designing his life (including his lifetime reading plan) I did not expect his essay, “I can’t help but feel writing about life detaches me from living it.” I was worried he was right. He says there’s a “spiritual cost” to writing. From our talks, I sensed there’s both an intrinsic and extrinsic risk:

“Writing is an act of vanity, elevating the importance of your thoughts, making it easy to begin to worship your own intelligence—you care about feedback, people thinking you’re a good writer, not wanting attention to stop or go away … There is a certain Faustian bargain writers make, where their excessive introspection and ruthless observation lends to a stunning landscape of the soul, but elevates their interiority to a dizzying height, from which all they can do is fall.”

This might explain why Tommy hides his Substack metrics, or why he said he was “somewhat horrified” to learn he won this essay prize. He knows the disorientation of attention,1 the danger of a validation spiral, and is wise enough to try to keep things small. “I just want to write thoughtful, cozy kitchen-table essays that a few people read with a coffee.”

Part of my goal here is to make sense of this paradox, that writing can be both liberating and alienating. The truth is definitely more complex than “embodiment = good, abstraction = evil,” and so I want to think it through and find the critical nuance, the way forward. When is it okay to retreat into your head?

Back to floating heads: This is the default shape for a citizen in a screen-addled culture, but it has a history in describing the shape of the writer, the artist, and the mystic too. I’m sure there are instances before Emerson, but this passage from “Nature” (1836) is my personal sense of the origin: “Standing on the bare ground,—my head bathed by the blithe air, and uplifted into infinite space, —all mean egotism vanishes. I become a transparent eye-ball; I am nothing; I see all; the currents of the Universal Being circulate through me; I am part or particle of God.” Here, he frames it as a positive: the loss of body, and the reduction of a self to a pure and total perception, can lead to transcendence. Naturally, he was criticized. His friend Christopher Pearse Cranch (another Transcendentalist), made a caricature of this idea: a sketch of a giant eyeball in a tophat, a suit, and long slender legs, levitating above and wandering through a barren landscape. In other works of the 19th century (from Hawthorne to Dickinson to Melville), you find the sentiment that reducing yourself to a disembodied gaze will corrupt, blind, and eventually kill you.

A modern incarnation of this phrase comes from David Foster Wallace in his 1997 interview with Charlie Rose: “The things in this [essay] book that most people like are the sensuous or experiential essays, which is basically an enormous eyeball floating around something, reporting what it sees.” Both Tommy and I are fans of DFW, but he noted, “he’s very sharp and critical and funny, and he’s right in a lot of ways. But in another sense, it’s just another way of abstraction. It’s another way of keeping reality at an arm’s length.” DFW defined a style of hyper-aware self-conscious writing, an anxious person in an anxious place, yearning for authentic connection but never finding it. It’s fascinating to occupy his headspace, but it’s probably not the default state you’d want to live in. I imagine he was such a great essayist because of his background (focused on fiction, educated in philosophy, raised by language snoots), but maybe his crutch was that all his essays were commissioned by magazines.2 The premise is often let’s send this extremely articulate guy into an extreme place to make sense of it. And so we see him on a cruise ship, at the lobster fair, in the porn convention, along the McCain campaign… we see his assignments, but rarely the particularities of his life on the average day (his relationships, his job as a teacher…). There is one essay written from his home in Bloomington, Illinois, but it was 9/11. We mostly know about his life through interviews, letters, and biographies. While his essays did feature highly personal, unbelievably lucid, 5/5 experiences, they were outliers: stunning and prescient portraits of our culture, but nothing he’d ever do twice. It’s even in the title of his first essay book, “A supposedly fun thing I’ll never do again.”

You can see how being extremely in your head in alienating places can be fun, shocking, legendary, but also disembodying. The opposite of this is being rooted in a sense of place, something Tommy eventually wrote his way into:

“The first three, maybe three and a half years of my writing, a lot of it was writing about abstract ideas—there was no onus or responsibility. Even my parents who love me more than anyone were like, man, you’re writing about this stuff, but we want to see you live some of this more. One of my goals for 2025 was to write more as ethos. I wanted my essays to be deeply rooted in how I lived my life, not forgotten philosophical pandering.”

There is probably something important in starting essays from the actual circumstances of your life, rather than retroactively finding stories to fit an idea, framework, theory, or phenomenon. While Essay Architecture asks what are the composition qualities of great essays?, Tommy is helping point me towards the question of which essays should you actually write? In an over-simplified and instructional way, I guess this comes down to topic selection. Are you writing about stuff that matters to you? Or are you misled by your own writerly identity, writing the things you think you should be writing?

Maybe the point of an essay isn’t to help you think better, but to help you live better. It’s a simple but radical departure from the trope. If the point of writing is to sharpen your mind, to communicate better, to make you smarter, to enable you to rotate ideas until you can effortlessly find the counterpoints, then isn’t that an exercise in expanding your already-endlessly-expanding head? Maybe essays are less about cognitive sharpening and more about navigation. Where should you be? What do you value? Who matters? When should you stop? Why bother? If you’re going to spend 10 or 20 or 100 hours expressing some idea as elegantly as you can, it might as well be a one that’s aligned to your situation, because any idea you spend so much time with is bound to slant your vision. If the point of writing is to unlock some dimension of our life, then the resulting artifact of words, the essay, is just an incidental bonus.

This might sound too pragmatic, too self-serving, but if you’re not deeply entangled in a topic, you can’t possibly know it in a way that’s specific enough to resonate. Tommy:

“In order to touch people’s lives and to actually move people’s hearts in a way that is life-giving, you kind of have to selfishly write about the things that you’re interested in and only through that can you breathe enough life into them. [ … ] Everyone wants to change the world, but no one wants to change himself. You have to start on the level of the individual... put yourself together first, then your family, then your community. That’s where change can really be effected.”

It’s very easy to get caught up in external metrics—to judge ourselves by the impact or visibility of our work—, and it’s also easy to think that spiraling through an abyss of thought is productive too, but it feels important to remember that, when we write, all we really need to do is solve our own problems, follow our own questions. This approach makes an essay practice maximally approachable, a true folk medium. You do not have to be a professional writer. The majority of the writers in The Best Internet Essays 2025—if not the entirety—are not full-time writers. As of March of 2025, Tommy got a full-time job. He originally thought he needed complete freedom over his time to write, but he’s since found the opposite: the stability of a job lets him protect his practice and stay focused on ethos. He assumed he’d only be able to write for two hours a week (probably on weekends), but he found the practice so ingrained that he couldn’t help but write a whole lot more: “I think it does become fundamental to how you process the world in a way that you can’t just rip out.”

Now that I’ve written all this, it’s helping me clarify when I should shift into abstraction, when I should embrace being a big floating head. If I’m going to retreat from life and spend a considerable amount of time in the inner caves of mind, it should be towards something that refines my character when I return, Bodhisattva style.3 Life in retrospect is a palette of fuzzy and undigested experiences, and I can’t properly process them without solitude. By logging my days at the highest resolution I can, the on-the-page abstractions will be an approximation of me. This leaves me with atomic blocks of words that I can interrogate, re-arrange, disprove, expand upon, all towards the end of finding a new insight, a lens for my future self to experiment with. Like a hot air balloon, the floating head comes back down. When writing starts and ends with the ground reality of your life, then the essay is a path towards self-guided evolution:

“In an ideal world, you as a writer and you as a human being exist in a kind of ecology. You can write your way into development, and then that more developed person can write further things, and it’s like an upwardly ascending spiral. I was thinking of Thomas Merton, a Catholic monk—in some ways, he wrote himself into faith: he wrote about his belief in God, until he started to believe in God. [ … ] As I’ve tried to put more emphasis on writing as ethos, and writing about ideas that become fundamental to the man I’m becoming and not just a kind of periphery safe intellectualizing, I’ll notice these things coming up in the day-to-day, coming up in conversations… like I find myself actually absorbing these words, and that seems a lot more meaningful to me. And it’s a more meaningful stance to take as a writer: I’m going to write my way into a beautiful existence.

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Footnotes:

This is article-brained thinking: it’s focused on external facts and authority through scale, the antithesis of the essay. David Foster Wallace said essays are “occasions to watch somebody reasonably bright but also reasonably average pay far closer attention and think at far more length about all sorts of different stuff than most of us have a chance to in our daily lives.“ An essay puts you directly into the mind and circumstance of a stranger, to the extent that language permits. The potential of an annual essay anthology, then, is in creating a human-shaped way to understand the culture these writers live in—a mosaic of experience, where each tile helps triangulate the hidden but central truths that animate and haunt us.

To be clear, The Best American Essays has made annual anthologies for forty years now, but after reading the 2024 edition, I learned 70% of the essays were memoiristic flashbacks, written in 2023, but not about it. And so this was the only constraint around my 2025 essay prize: capture the spirit of this year. Both timely and timeless, it was an open-ended prompt. All sorts of essay were submitted—personal essays, nature essays, lyrical essays, fragmented essays—around very different topics, and yet they all seem to revolve around a similar thing.

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The approximate theme of The Best Internet Essays 2025 is this: there’s a yearning for an intentional life in face of the dizzying and disembodying effects of a technocratic society trying to commoditize you, to commoditize everything. The modern world brings a slew of benefits: convenience, speed, efficiency, optionality. But secretly bundled with its many promises are invisible amputations: an erosion of place, a numbing of the senses, a hollowing of our interior. Each essay feels lodged in a modern struggle, but is defined by a writer’s earnest attempt to derive their own way to see and live through it. There are endless things to worship, to grant our attention to, and that is the most consequential choice we can make.

Personally, this collection resonates because a month or so after the prize window closed, I had my first child, my daughter. Having a kid is possibly the most out-of-the-matrix and into-your-skin experience you can have. It’s something like ego-death—to switch from a language-based reality to one of burps, farts, coos, and smiles—and it challenges me to be slower, more perceptive. Something my daughter loves doing is “the grand tour,” where I bring her up to my shoulder and walk her around the apartment, showing her all the art we’ve hung up, the art of my wife, her mother and grandmother. I’m surprised how transfixed she can get on visual objects. She stares at paintings for much longer than we usually do, and so I try to join her. I’ve started noticing all these subtle details, marks and mistakes, easter eggs, things I never truly saw on the walls surrounding me for years. In some way, that’s a metaphor for the theme of this book: we’re all tapped into a vast stream of information, a totalizing dream of work and play and doom, but even all of that is dwarfed by an infinite canvas of texture and meaning in the world around us, in the space beyond the edges of our screens, if we care to look. There are walking-distance mysteries.

Maybe it’s because I’ve read through the essays in this anthology 5 or 10 times by now, but they’re imprinting on me, and I find myself seeing through them as if they’re lenses. The essay is unique, compared to the article, because it packages insight into a scale you can relate to. It’s less about the facts and stats; more about ideas you can transpose into your own life and try out. I’m only formulating this now, but I think sensemaking is better assimilated when it’s paired with first-hand experimentation, rather than the exhausting attempt to be informed, well-read, and intellectually-versed in the happenings of a somewhere else.

Have you tried being informed recently? I’ve recently made the mistake of signing back into X to make sense of world events. Why I did this is a topic for another post, but what I want to comment on here is the nature of our biggest sensemaking apparatus. Elon criticizes the legacy media of spin, but it seems the default “For You” algorithm on X uses spin as its reward function; the more distanced from the truth, the more extreme it is, the more likely everyone will see it. It’s barely about left vs. right anymore, it’s more so aimed at Total Shock, to paralyze your mind and keep your fingers moving. A few examples: the Epstein files shifted the Overton Windows for celebrity corruption, to the point where it’s now apparently feasible for Ellen Degeneres to be a satanic cannibal that ate Stanley Kubrick in 1999 (not mentioned in TIME); real combat events are being augmented with plausible but apocalyptic CGI footage, with a thousand comments of “@grok is this true??”; AI product updates quickly spiral into predictions and bets on when a superintelligence will commandeer the entire economy. And so yes, there is a confluence of extraordinary events, but the ever-escalating media machine is refracting all of the chaos through conspiracy, fabrication, and extrapolation— a schizophrenic filter. Anyone trying to make sense is bound to get paranoid. The X feed is not just slop, it’s a strong anti-signal, a distillation of our collective fear.

A closing thought that hopefully ties this all together: articles, videos, and shortform content are more prone to bend around hysteria than essays are. Essays, of course can and do go viral, but the requirement of reading thousands of words throttles the reach. It’s an ineffective form of propaganda. More importantly, the whole point of even writing an essay is to attempt to make sense of something that matters to you. This means truth-seeking is baked into the process, and the reader is invited to join in the sensemaking.

The potential of an essay anthology is to create a cadence of timeless reflections, all anchored in the same timely moment, trying to make sense of it. If fast-paced viral news atrophies your attention, then slow-paced essays should expand it.

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The original driver of this post was really to share a small excerpt from each writer in The Best Internet Essays 2025. Each paragraph taps into the larger theme that emerged. Here they are:

"I could throw around loose and loaded terms like presence or attention or intentionality (or worse, embodiment) and we could both pretend we know what I mean. But the truth, the real answer, is something more slippery: to willingly and voluntarily and stubbornly choose a slower, sometimes boring, more inconvenient mode of living, viscerally experiencing the endless minutes inside an hour, flying in the face of what everyone else is doing and your instinctual animal impulse to be stimulated, to avoid discomfort and fear, to light up your brain's pleasure center like a 1980's pinball machine, which, as you know, is short-term rewarding and fun, but long-term not the most meaningful way to spend a life and lends a kind of flatness to your days that is indistinguishable from despair."

"What we should want is to be experientially old, not biologically young. There is a way to harmonize the two without becoming deranged by the constant measurement and management of biomarkers, without resorting to a transhuman diet, or an antisocial sleep schedule, or a fear of dying. The way we currently think about longevity mostly misses the forest for the trees. It measures age based primarily on 'biological time'—on relative organ and 'biomarker' health—a proxy for expected lifespan, which can't even guarantee a longer life. 'Experiential age,' on the other hand, can guarantee the perception of having lived for longer, through a rich abundance of memories and impressions."

"And I daresay Charlie Kirk, dead, is even riper for the picking than Charlie Kirk, alive. If Jacques Ellul lived to see his public execution, he would say the algorithm is the greatest propagandist of all, a mechanical black priest with a singular virtue: attention. It crowns what best captures our eyes, even a snuff film. It baptizes fear, shock, disgust, making us gag out of reflex even as we lick our screens clean, begging for more horror. Even though I’d avoided Charlie’s graphic murder, I’m still a “21st-century schizoid” like you: I found out just last week that Charlie wasn’t shot in front of his family. Who spread that lie? Who benefitted from spreading that lie? Perhaps you’re tempted to blame specific people, groups, foreign adversaries, as I am. But from a bird’s eye view, it’s the machine. It’s the machine that serves Charlie’s death, the machine that turns even my 5 ft 4 mom into a Dragon Lady fit to kill. We haven’t descended into 4chan or Kiwi Farms or LiveLeak; we’ve given the beasts escape velocity from quarantine. And there’s no unringing this bell. Hell is empty, and all the devils are here."

"In The Odyssey, Odysseus is held captive on an island after the Trojan war. Holding him there is the goddess, Calypso promising him eternal life, eternal youth and eternal sex. This is the image of hookup culture, in case you thought it was something new. It’s the age-old promise of never having to grow up—the ability to continuously find newness and youth in others and to therefore renew the youth in yourself. You can easily imagine how a man like Great Odysseus would be tempted to rest on his laurels. [ ... ] His wife back home, Penelope, though very beautiful, does not compare to Calypso. Worse, she will quickly become old and ugly and tired, like Odysseus himself would, if he left the island. He chooses Penelope. He chooses to go home. And he is punished for the length of the novel as a test of the graveness of that choice."

"We hadn’t told our friends yet, but now I announced both in one successive sentence: “I’m pregnant but I think I’m miscarrying.” And even as I said it, I knew I was partially saying it as a talisman: if I said it was possible, then it would not be so. And it’s a funny thing, an English teacher realizing she’s miscarrying in Parliament Hill Fields, the very place Sylvia Plath writes about wandering with her miscarriage grief. The knife of January is in her first line: “On this bald hill the new year hones its edge.” Thinking of Plath then was enough to make me second guess my intuition—I’m so impressionable, I shored myself, striding across the frost-charred grass and mud, arms stitched around my middle. But it’s a strange thing about being an organism, to know and not know our own interiors at all times, but then to have certain moments of intense understanding about exactly what’s going on in the inside, like strangers on a train suddenly kissing."

"I am released into the park. There is not a cloud in the sky. Vendors sell potato chips drenched in hot sauce by the lake, sling beverages from coolers, while kids squirt water at each other from ubiquitous Changuito Mion hats [ ... ] I’ve come to ponder this very essay, but no clarity strikes me. [ ... ] I do not know what I am trying to say. I do not know what anything means. And then, for a second, I see the kids squirting water, really see them, see them laughing and running and annoying their parents, and I see the parents, and I think of my own family, and there are so many people in the park, so many people, in this day and age, alive, and for a second I understand, I see it all—I understand what everything means, that although everything has changed everything, actually, is the same, has always been so, and this light of sameness lives on in each of us, despite the lever pullers, the power brokers, and, though we may be killed, may be broken or displaced, this spirit, this beautiful and painful constancy, will remain whole. Try as villains might, this thing, this mysterious thing, will not be broken. And I watch the parents and wonder what they’re thinking. Do they know? Do they know what they are seeing? But then the thought leaves. It simply leaves, and I am swept back into the hollow meditation of my walk. Everything returns to the way I saw it before. Essentially, I no longer see at all. I leave the park and return home on the metro, allowing my small epiphany to be blasted to the fringes of my consciousness by the news cycle."

“Brain rot,” surprisingly, was first coined in Thoreau’s Walden in 1854. It is the decline of one’s ability to concentrate, think critically, and “be in the world appropriately.” The definition hurts only because its aim is true. Go ahead and cast the first stone, those who have not experienced even a moment of this rot. Consider a girl: hunched over her heavy book, tearfully moving from one page to the next, and in the midst of it, checking her phone at the slightest hint of a dopamine lull. It’s noteworthy that “brain rot” is linked with excessive exposure to low-quality content, and one of the suggestions to combat it is engaging in non-digital activities. Thankfully, reading a physical book falls in that category.

"This convention for the sexually repressed (and just curious, or committed to improvement) boasted many workshops, but most of them boiled down to: get out of your own head, and push your boundaries. Men were instructed to stomp their feet or shove each other to be embodied. They swapped nervous system regulating techniques. They were instructed to unclench their jaws. Privately, I was taking notes. [ ... ] I like embracing perversion, the control it offers my own sexual experience and also the way it cracks open what can be considered erotic. But seduction takes risk, and the lower the risk, the lower the potential payout. If I don’t allow myself discomfort, if I eliminate risk completely and only entertain my specific predilections, how can I expect to experience the potential highs eroticism can deliver?"

"Back in the Era of Guys, you didn’t even need to actually do drugs, because merely acquiring them was an adventure in and of itself. And all the effort you’d put into getting them made you enjoy the experience that much more, IKEA-effect style. That’s all gone now, and not just for weed. Psychedelics may still technically be illegal, but they’ve fallen victim to this same process of enlameification. Ecstasy used to come in sketchy little pills with skulls or Pikachus stamped on them, and you took it at clubs so you could feel up strangers or trick yourself into liking terrible music. Now it’s called MDMA, and your stepdad takes it with his therapist to help process his divorce. LSD used to make you drop out of society, or at least get you kicked off the Harvard faculty; now it’s something you microdose so you can be 10% more productive at your job optimizing Google ads."

"The danger of all this convenience is that one begins to live inside a very narrow band of the visceral world. I believe our surroundings exert themselves on us, gently but continuously. Everything we see and touch day to day conspires to shape our moods. When places are too antiseptic, we grow unaccustomed to noticing visceral details. We start to use less of our senses. Over time, our surface for pleasure thins."

"John Keats, in his poem "Lamia," warns that analysis dispels Nature's mystery, that rationalism kills wonder: "Do not all charms fly / At the mere touch of cold philosophy?" He describes the anti-romantic business of analysis as "unweaving the rainbow." Keats means that to reduce something so awe-some and wonder-full as a rainbow to the physics of light-refraction, for instance, is to "clip an Angel's wings," to "empty the haunted air," to "conquer all mysteries by rule and line." Keats places analysis and science at odds with wonder and romance, but this has not been my experience. His theory does not hold in the case of my first encounter with a horseshoe crab. By researching this animal's anatomy and physiology and history, something that was foreign and, at first, frightening to me became more awesome and wonderful."

"There was a period in my twenties when I didn’t get art. I thought artists were trying to say something, but I felt superior because I thought there had to be better ways of getting their ideas across (and also, better ideas). But then I realized that good art—at least the art I am spontaneously drawn to—has little to do with communication. Instead, it is about crafting patterns of information that, if you feed them sustained attention, will begin to structure your consciousness in interesting ways. Art is guided meditation. The point isn’t the words, but what happens to your mind when you attend to those words (or images, or sounds). There is nothing there to understand; it is just something to experience, like sex. But the experiences can be very deep and, sometimes, transformative."

Check out the book on Metalabel

This little book, a 4.25” paperback that fits in my pocket, is the manifestation of a big, borderline extreme process I was entangled in all of last year: I wrote a textbook on essay composition, analyzed classic essays along my framework, built software to give feedback, which powered a tech-forward essay prize, creating a shortlist for our team of judges, all leading to this—an anthology. Since Essay Architecture risks veering into hyperanalysis, it’s relieving to have something much simpler I can share. It’s a book. You can read it, experience it, a single thing with a URL I can text Andrew along with “yeah here are some great internet essays written in 2025 about 2025.”

From over 900k words processed across 400 uploads, we had 10 judges (each with their own criteria) who read every essay on the shortlist. It was fascinating to read through their comments and scores: if you looked at any one essay, it seemed like there was little consensus, that quality is subjective, that there can be no “best”; but if you zoom out and compile the results, it’s clear that some essays resonated across many different lenses. Those essays are the ones we’re printing. Congrats to the winner of our first prize, Tommy Dixon, and to all the finalists who contributed powerful, personal, “unitive” essays to make a mosaic of our year. You’ll find recurring themes on rootedness, loss, wonder, vulnerability, and ultimately, the power of attention in a culture designed to hijack it.

The Best Internet Essays 2025:

• Features 13 essays from the Essay Architecture Prize;

• Limited edition: 1,000 copies;

• Available March 11th - March 31st;

• Shipping starts in April;

• Pocket-sized paperback, 4.25” x 6.875”;

• 183 pages;

• $29 (+$8 for shipping).

Most importantly, 100% of royalties go to the writers, the judges, and the 2026 prize pool. When you buy a copy, you’re directly supporting the people behind the essays, the team who helped surface them, and the future of this anthology.

Head over to our Metalabel release page to see the winners and get a copy.

Buy the anthology

If you’re a reader of Essay Architecture, it’s definitely worth having a physical book of essays within arms reach at, almost, all times. Printed essay anthologies are an underrated genre. Commercially, they basically don’t exist, usually limited to a single half-shelf in a secret corner of a Barnes & Noble. But if you’re an aspiring writer, it’s the best kind of book to own. You get a range of ideas, a range of voices, a little universe of inspiration all within one cover. If the book is well-curated and well-edited, it’s the kind of thing you can reliably pick up to get a full dose of literature in a single sitting. I scatter these across my home so I’m more likely to accidentally fall into one.

Also, this particular anthology fits in your pocket (I’d prove it but am hesitant to post crotch-adjacent photography online). There’s a collector’s mentality of seeing big, hardcover, premium books as a mark of quality. Personally, I like my essay books small and bendy. Portability is a huge asset, especially as spring nears. Bring it outside without a bag, on trains, to parks, wherever. Leave the phone home, too. The vision is to, each year, curate the best writing online, the writing the algorithm may or may not miss, the writing you’d likely flick through on your phone, the amazing writing you find and bookmark but inevitably forget—to assemble all the essays worth reading off your phone and onto a printed thing about the same size as a phone.

In the coming weeks I’ll be writing more about the anthology, the emerging themes, and the vision of this becoming an annual effort to curate Internet essays.

Get your copy before March 31st

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The deadline for the $10,000 Essay Architecture Prize is at the end of today! In addition to the grand prize, a dozen or so finalists will be published in a Metalabel anthology (which hopefully brings $1k per writer). Last call to upload or recommend your favorite essays, written in 2025, capturing the spirit of 2025.

In case you’re not aware, there is a 40-year old system that reads through all the literary essays published in North America, condenses them into a single book, a handheld thing, and then confidently claims, “these are the best American essays of the year” (it’s in the title: Best American Essays). This is a tremendous service. Do you have time to read—in addition to the torrent of your Substacks, shelves of classic books, and milieu of podcasts—several, entire publications per day? (If you do, please send me an email.1) There is comfort in knowing that, even if you fall behind your evergrowing reading queue, someone has done the hard work of collecting the essays that you wouldn’t have wanted to miss. I respect the scope, endurance, and ambition of this process. Once I heard about it, it wasn’t long before I bought the entire collection on Thriftbooks; it only costs $300 and it fits in your trunk.2

But it wasn’t until I read, scored, and reviewed the 2024 edition in full that I became suspicious of their notion of best.3 An Amazon review described the anthology as “tragic experiences communicated in artful ways.” 68% of the essays had death as its core theme, and the remaining tapped into other extreme vulnerabilities (jail, rape, gender surgery, etc.). Of course, no topic should be off limits, and a publication has the right anchor itself in a specific perspective. However, Best American Essays, at least in my mind, has a much different responsibility than The New Yorker or an indie litmag: they are the “curator of the curators.” They are the leading institute in championing the 450-year institution of the essay (a genre that has potential to become the most relevant written medium of the 21st century4—a genre not to fumble). It feels wrong to me that they’re conflating “best” with their particular agenda for the genre (an obsession with devastation).

Why does anthologizing matter? Well, what you anthologize becomes legible to the culture, and what you don’t anthologize stays unconscious. Literary movements start in the shadows and only emerge from ambitious curation schemes.5 In 2004, Paul Graham argued that the Internet—free from literary gatekeepers—would usher in “the (golden) age of the essay,6 and while I think he was incredibly right,7 he missed the fact that the whole movement might be somewhat illegible. How would you know we’re in a golden age unless you personally keep up with several thousand Substacks and review them? All year, timeless essays are casually flooding the Internet, some go viral and some go in the gutters, but everything is disaggregated, the platforms mostly care about revenue, and the word essay exists in a fuzzy limbo with its sibling genres (the article, the newsletter, the blog). If we can define WTF an essay actually is, reclaim the word, agree on what makes one high quality, build systems to discover the best ones, pay them extremely well, and assemble them into (popular) books, then we can capture where the real heart of the 21st-century essay lives.

And so the aim of the 2025 Essay Architecture Prize, in addition to paying the winner $10,000, is to assemble an anthology of high-quality writing that both captures the spirit of the year, while also showcasing what’s happening online. It’s an attempt to innovate on how you pick the winners. It’s not a single guest judge. It’s not a team of guest judges that are all slanted by the same agenda. It’s also not entirely up to my terrible8 machine. The experiment is rooted in two questions: (1) what is quality? and (2) how can we create a dynamic system of frameworks and people to agree on what makes something the best?

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The quality debate:

The quality debate is a thorny one that usually devolves into “everything is relative.” I’ve talked to non-readers and even once the head of an Oxford English department, and the consensus is that any single definition of quality is too myopic. I actually agree. We have different schools of craft, different worldviews, and readers with different tastes who adore different canons, and so in a culture that is endlessly diverging, it’s fair to assume that it’s impossible to unify everything under a single, simple criterion. Even if Essay Architecture succeeds in building software that can detect all the nuances of composition, it will never be able to compute the incomputable: ethics, soul, originality. Quality is more than being well-written. It’s more than a righteous point of view, or the ability to stir up unusual feelings inside you. It’s somehow a blend of all that.

My emerging thesis is that quality is the transcendence of categories. A simple example: lots of philosophers ignore the musicality of their prose because they’re so focused on their argument; and also, a lot of literary types are so locked into the aesthetic quality of each word that they neglect the cohesion of their thesis; but then consider G.K. Chesterton, who makes sophisticated arguments in extremely phonetic ways. He transcends a boundary that often divides writers. Even though an essay can be great along any single dimension, maybe quality is multi-dimensional, fusing things that don’t gel. It’s not just power, not just range, but range x power.

So I’ve designed our judging system to have 10 people that cover three different branches. Each branch—composition, perspective, and taste—represents an opposing way to think about quality. I use the word “branch” because I see this working somewhat like the American system of government (as designed), a triad of checks and balances. There are judicial laws that evaluate the fundamentals of essay writing (Essay Architecture), a council of people that represent different corners of the Internet (effectively, the legislative branch), and then a single executive, a well-read Internet citizen with a unique ability to interpret the intangibles. An essay that excels in one branch might be weak in the others: perfect craftsmanship might be soulless, a revolutionary perspective might have choppy prose, an original might alienate the public. And so the essays that can transcend all three branches might truly earn the title of best.

What makes this maxim interesting to me is that it’s fractal: if you zoom into any branch, you realize you can only master it by transcending the inner tensions of that branch! And so, I’ll write a quick paragraph on each one, so you understand how it works and who the judges are.

Composition:

The Essay Architecture app will score all uploads 1-5 on 27 patterns, make the longlist of the top X%, and then I’ll manually rescore to confirm accuracy and make the shortlist.

My framework is an attempt to define the essay at the genre level, but the common question is, “does every essay really need all 27 patterns?” The essay has many sub-genres that only care about a subset of patterns—the personal essay, the fragmented essay, the braided essay, the lyrical essay—but this constrains it to a particular type of reader. The essayist has the ability to touch all sides of the psyche, to fuse the soul of a memoirist, the rigor of a philosopher, the pen of a poet, the persuasion of a marketer, the research of a journalist, and the imagination of a novelist. The “unitive essay” can transcend all those archetypes into a single thing, and we should celebrate the ones that do. Here’s a library of examples, where the score represents ‘compositional well-roundedness.’

Perspective:

A team of 8 judges, each with their own speciality, will score each essay on the shortlist over three subjective criteria.

A reader is often drawn to a writer because of a worldview, a vibe, a perspective. They might care less about the craftsmanship of the writing, and more about the specific angle towards the world. Unlike the patterns in composition, this is mostly subjective. It’s hard to say if one perspective is better than another, but we could measure “inter-subjectivity,” the resonance of an essay across different judges. My goal was to assemble a team of writers and editors who each represent a distinct sphere of online writing culture. Our team has doctorates and comedians, memoirists and journalists, people with different temporal lenses, to the past, present, and future.

Judges will score each essay on the shortlist across three questions, each colored by their perspective: (a) do you like it? (b) do you think it captures the spirit of 2025? And for (c) each judge gets to shape their own question. Here are the judges (A-Z) along with their question:

1. : “Does it elicit powerful emotions?” She’s published almost 300 weeks in a row in Substack, including personal essays, newsletters, and 62 episodes of Memoir Snob, where she explores the nuances of writing from Experience (the defining pattern of the essay). She fearlessly puts her life on the page, and is becoming an expert at articulating the techniques of relatability.

2. : “Is it funny, honest, and true?” He writes Both Are True, a top comedy Substack that is a sweet mix of zaniness and vulnerability. Alex is the sensei of “platform tilt,” a technique in making and breaking frames, where you are constantly falling through the floor and laughing as you do it. In contrast to the schoolish definition of “essay as bullshit homework,” Alex shows that an essay can be a labyrinth of jokes that coax you into the heart of something real.

3. : I tried to finagle some criteria out of him, and the best9 we could agree on was “Is this essay a fusion of pensive apeman and unbarnacled starfishman using deep gazpacho technology to capture the human lotto scratch off vibes of harmonized tubular audition tape?” Said otherwise: “Does the writer bring a unique essence to the topic at hand?” Mr. Foote is a subversive essayist, a corporate jester, and eventual host of bingo night at the Sphere. I became an instant fan when I read his essay written from the perspective of a squirrel.

4. : “Does the essay bring a solutions-oriented mindset to an important problem?” Elle is the founder of the The Elysian Collective, a publication dedicated to futurism and utopian thought. Historically, the essay has been a vessel for civic imagination, and Elle is committed to use her writing to help design the future we want. In that spirit, she’s pioneering new models of crowdfunding, community, and print publishing.

5. Lellida Marinelli: “Does it have an essayistic mode of thinking?” An Italian scholar with a PhD in essayists writing about essays, she is extremely knowledgeable in the history of the medium, specifically on how writers have reflected on the genre and process. Check out her academic papers. I’m excited for her to see if century-old traits—complexity, lyricism, heresy, etc.—have organically re-emerged in online writing.

6. : “Does it grapple with the timeless human condition?” He’s the Senior Editor of Infinite Books and a digital custodian of the canon (bringing C.S. Lewis, Dostoyevsky, and ilk into our feeds). He’s ingested an incredible amount of information and has put together encyclopedic indexes on rhetorical forms and the writing life. Excited for him to bring a historical lens to essays written in 2025.

7. : “Does the essay offer a unique way to understand a world in flux?” Jasmine is an “anthropologist of disruption,” was a product manager at Substack, and co-founded a techno-optimist publication called Reboot. She’s interviewing people at the edge of culture and tech, and has a sharp sense of the forces shaping the moment.

8. Unraveled: “Is the essay grounded in hope?” Isabel is a creative guide and writer who explores the intersection of intuition and expression. She helps writers—including me—break through different layers of psychological resistance. Beneath her notes and essays is a trust in the process, a sense that through hope and action, writing is an act of personal transformation.

Taste:

A single judge, the wildcard, will rank essays however they like, ideally to capture the intangible qualities of an essay.

While composition is about timeless patterns, and perspective is about cultural vectors, taste is about the discernment of a single, trusted reader. What makes good taste? I need to think/write on this more, but for now I’d argue it has two halves. First, it requires someone to absorb a substantial amount of cultural works, which gives them both a map of what exists, along with the embodied experience of feeling and reacting to different types of things. Second, it requires an ability to notice and articulate why a small portion of what they’ve seen is particularly special, even if the culture finds it weird or difficult. Taste, then, is high exposure x high selectivity. When a well-read reader absorbs something new, it gets located in their map— consciously or intuitively—and it’s processed as familiar or strange (Harold Bloom says everything in the western canon is united by a “strangeness,” an original vision that transcended the expectations of its time). Someone with good taste is in a position to articulate intangible qualities—originality, ethics, aliveness—because they are evaluating through deep context and the depths of their experience.

I’m thrilled to announce that our guest judge for this branch is , the writer behind Escaping Flatland. Not only is he an astounding model of a modern essayist, but I think he’s the perfect counterweight to the Essay Architecture system. While he is similarly inspired by Christopher Alexander—and has even written about pattern languages in essays—he also describes essays as “forcefields of energy” on the How I Write podcast. I think he’s onto something in his latest essay on non-linguistic thinking, and hope this judging experience lets him advance his ideas on how to somatically evaluate ideas without words. Henrik recently shared his rigorous reading process along with a list of 71 books. My sense is that he is a synthesis of two very different archetypes: the topologist and the animist; his list spans poetry, systems thinking, the diaries of mathematicians, and the biographies of filmmakers. He’s curated a rare mix of inspirations, and I’m excited to see how he responds to the essays in the shortlist. I’m not asking Henrik to score anything 1-5, but to read them, to reflect on them, and then rank them according to whatever criteria feels salient.

Last push, let’s make an essay book:

What kind of essays will emerge from a system like this? The goal isn’t to define quality with an absolute or singular definition, but to create a living process where the winning essays are the ones that transcend fractal systems of interlocked tension. Each of these branches represent 1/3rd of the decision.10

The deadline to submit is today, Sunday, November 23rd, at the end of your day. The reading window will be December 1st–21st, and we’ll announce the winners and anthology in Q1 of 2026. I can’t wait to have a single artifact that (1) represents 2025 through a mosaic of essays, and (2) captures the energy of the online essay movement. Most of the people in my non-Internet life have only a fuzzy idea of the world I exist in, and so I’m excited at the prospect of handing them a book that has a decent possibility of blowing their mind (I believe great essays harbor the potency of literature in a single sitting). Hopefully, the anthology gains enough momentum to help spearhead a 2026 essay prize, too.

Some ways you can help:

• Submit essays you’ve already published this year that capture the spirit of 2025. You upload through the app, get feedback (which at this point, you can likely ignore since it’s the last day), and then you’ll see a ‘Submit’ tab on the right. You can use the code ESSAY-PRIZE-2025 to claim a free upload credit today.

• Share this, either by restacking, or by sending it to your friends and favorite writers.

• Recommend your favorite essays from the year in the comments (or feel free to message them to me directly).

Thanks for following this experiment; excited to share the results!

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Footnotes:

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Some books on ‘how to write’ will tell you that, to get good, you just need to reduce your favorite writers down to reusable formulas. This was the gist I got from Elements of Eloquence. There is a standard way people think about “rhetorical forms,” but it feels too convenient to dull down creative expression into a dictionary of mad libs. If you merely imitate the syntax of your favorite authors, you’re actually not so different from an LLM.

If you use flowery repetition because Joan Didion does, and you thought it was pretty, and it’s something you think good writers should do, but you don’t truly get when, why, or how to pull it off, you might sound more robotic than you think. It’s hard to differentiate AI writing from bad writing. They have the same problem: they replicate patterns without understanding them beyond the surface.

I bring this up because—now that I’m done with the lift of launching Essay Architecture (.com)—I’m resuming what is the infinite game of this project: reading and deconstructing great essays.1

Despite what anyone tells you—especially me—the simplest way to get good at writing essays, I think, is to read more “good” essays.2 Here’s a reading list of 100 I’ve put together.3 You really do gain a lot just from exposure, but once you get a habit going, it helps to consider how you read, too; the right analytical lens (along with deliberate practice) can unlock even more.

Let’s look at an excerpt, but we’ll go beyond “here are some repetition templates,” and into “in what situation would a writer do this?” Here’s the opening four lines of “Goodbye to All That,” a 1967 essay by Joan Didion.

“IT IS EASY to see the beginnings of things, and harder to see the ends. I can remember now, with a clarity that makes the nerves in the back of my neck constrict, when New York began for me, but I cannot lay my finger upon the moment it ended, can never cut through the ambiguities and second starts and broken resolves to the exact place on the page where the heroine is no longer as optimistic as she once was. When I first saw New York I was twenty, and it was summertime, and I got off a DC-7 at the old Idlewild temporary terminal in a new dress which had seemed very smart in Sacramento but seemed less smart already, even in the old Idlewild temporary terminal, and the warm air smelled of mildew and some instinct, programmed by all the movies I had ever seen and all the songs I had ever heard sung and all the stories I had ever read about New York, informed me that it would never be quite the same again. In fact it never was.”

This is the Hook, and hooks are hard4 because they have multiple jobs: they have to open a Tension, preview the Thesis, and establish the literary Tone. So naturally, a good hook often contains an insane density of patterns. There are 11 patterns in here, almost half the system,5 but I want to focus on the obvious one: Repetition.

I’m sure some of the loopage popped out to you, but the best way to deconstruct something is to visualize it. You only have so much bandwidth to make sense of a wall of text. By breaking sentences into vertical fragments, like a prose-poem, you see its modules. By spacing them with horizontal indents, you see how parts align, and how thought burrows inward. By overlaying shapes, lines, and colors, you comprehend the relationships almost instantly. When prose is in its natural form, the patterns are invisible; to understand something, restructure it so the patterns are obvious.

This is the practice of architectural diagramming,6 but applied to essays. Now read it again, and notice the nuances of repetition you might have missed before:

So, how do you absorb this? How would you learn to think and write like this if you want your own writing to have a similar quality? (I picked this example because it’s far too complicated to reduce to a simple equation.) It’s not about parroting rhetorical devices, but understanding how the devices help the writer articulate and augment what it is they’re trying to say.7

I love this example because it shows that repetition is more than a trick for whimsical prose-poetry, its structural rebar too. Without looping phrases to expose the logic of her lists, these elaborate ideas would collapse into complexity. A repeated phrase serves as a variable to connect two non-adjacent ideas. In sentence 2, when she says “I can,” goes on a riff, and then says “but I cannot,” you know what’s about to come will contrast what was just said. Sentence 3 is 98 words, 3x longer than her average sentence in this essay, but she uses an “and” stamp to divide it into three manageable ideas. And, in both s2 and s3, the subdivisions have their own nested repetition schemes! There are devices inside devices inside devices, all to the end of containing chaos.

If8 you find yourself in a situation where you find yourself needing to pack a significant amount of detail into a single sentence,9 then you might want to expose the structure of your ideas through repetition. This lets repetition work like a punctuation device, helping the reader get the relation between ideas in as compact a form as possible. Of these 184 words, 55 words are “looped” (30% of words repeat!). Repetition is not just a jewel, it’s a compression device. It lets you travel far without feeling tired.

There are many types10 of repetition, and also, many jobs of the pattern: to compare, to connect, to enumerate, to emphasize, to expose, to burrow, to anchor, to crown, etc.11 Within each of my 27 patterns is a whole universe of types, and the goal of my Essay Architecture book is to map everything as I read and deconstruct.

There are 2 different ways you can take part in this:

• Free subscribers will keep getting posts like this. I’ll always include links to the original essay, along with at least one visualized example of a pattern, so you can both see it and understand why you would use it.

• If you want to upgrade to a paid subscriber, you’ll be able to click into any of these pattern pages to find definitions, theory, exercises, rubrics, and a growing set of examples. From “Goodbye to All That,” I’ve already added 3 more visualized examples to the Repetition page (with more notes to upload). If you want to zoom out before committing, check out the Table of Contents, my primer on the system, or my free essay on the Voice dimension.

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Footnotes:

11

I’m inspired by Richard Serra’s—a sculptor’s—verb list, and I like the idea of classifying examples through actions that are easy to remember. I am making a conscious decision to stay away from the classical names for rhetorical devices: “anaphora,” “epizeuxis,” “polyptoton,” etc. 2 of these 3 three words are getting the red typo squiggly in the Substack editor because that’s how infrequently they’re used. Of course, all the phenomenon these Latin words describe are real, but they are as anti-mnemonic as it gets. If you’re trying to teach writers dozens of concepts, the last thing you want to do is give them multi-syllabic, pompous names. If you want these devices to be remembered and used, they should be named after common verbs, and should strive to be two-syllables or under. We have to start over. See Richard Serra:

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EssayArchitecture.com

I’ve been building an app for writers all year, and a few months ago I sent out a survey1: 95% of you said ‘essays as creative practice’ was the main reason you write, 80% said ‘improving the quality of your writing is 5/5 important,’ and the #1 thing stopping you is that ‘you don’t know the weaknesses in your craft.’

How are you supposed to find your blindspots? A writer is too close to the work—too enmeshed in every idea, too enamored by every turn of phrase, too entangled in their own context—to see it the way a stranger does. This is what feedback is for. The problem is that friends, family, and chatbots veer towards sycophancy; they flatter more than they challenge. To get critical insights into your writing, you could find a coach or developmental editor, but they’re often expensive or unavailable. My own go-to editor, the one willing to toss me feedback grenades, has disappeared into the Rocky Mountains. And as a developmental editor myself, I know the problem: a deep diagnosis can take days, and I charge upwards of $150/hour. Some college essay coaches charge $1,000/hour.

The main goal of Essay Architecture is to help you see the invisible patterns in your writing. Since it’s effectively an always-available $9 essay coach, I find myself reflecting on what exactly coaches do. How do they unlock mastery? (Is it really just motivation and accountability, or is it about technique?) What are the differences and challenges when trying to recreate a coach with AI? And what happens when society cracks Benjamin Bloom’s Two Sigma Problem and everyone suddenly gets access to infinite coaching? Naturally, I thought back to my own coaches, and there’s one that stands out: my private batting coach from high school, Fat Joe. In 9th grade I didn’t make the JV team but was offered a spot as waterboy, and so I sought professional intervention. Not only did Joe teach me how to really swing a bat, I learned the fundamentals of how to practice, and how to master technique; this applies to anything, especially writing.

Perfect practice makes perfect:

Every week my dad would drop me off at Joe’s house, and I’d walk through the side gate, back into his backyard baseball dojo, filled with mesh structures, metal contraptions, and of course, hundreds of loose baseballs. He was loud and jolly, intimidating but patient, always ready to roast me and laugh it off. He called himself Fat Joe, possibly because of his size, or possibly because of his resemblance to the rapper, Fat Joe, also Puerto Rican.

Before we started our first session, he asked me, “So Michael, practice makes perfect, right?” Not expecting the trap, I answered, “definitely.” “WRONG!—” he yelled with a grin. “Practice doesn’t make perfect, PERFECT practice makes perfect.” I didn’t know what this meant, or that it was coined by Vince Lombardi.

He explained that if you practice every day with bad technique, you don’t just fail to improve, you internalize habits that are hard to notice and even harder to change. This might explain why, after obsessing over baseball for 10 years—watching it daily, playing in multiple leagues each season, and hanging out in batting cages at summer camp—I still sucked. I may have swung a bat over 25,000 times, but with each bad swing I locked myself into mediocrity.

Fat Joe was able to diagnose my problems immediately: bat slouched, elbow down, barely stepping, lunging forward, and (worst of all) not twisting my back leg. He knew all the mechanics of a perfect swing, but more importantly, he knew specific drills to isolate and fix each part. His exercises were eccentric, but who was I to question him? I didn’t make JV and his son was in the minor leagues of the New York Yankees.

“Squish the bug!” Joe was pitching fastballs, but I wasn’t allowed to hold the bat. My arms were behind my back, the bat between them like a skewer, and my task was to keep my eye on the ball as I twisted my back right ankle as hard as I could to squish an imaginary cockroach. “C’mon, SQUISH it!” He’d tell me to imagine how gross the bug was, to put all my weight into it, to make sure it was dead. The point was not to hit the ball; the point was to isolate the part of my swing that was the weakest.

Once my ankle rotation improved, we switched to the next technique, and then the next. He seemed to have drills for everything. Sometimes he’d put the ball on a tee and make me swing with one arm. Sometimes he’d pitch from the side. Sometimes from behind. I was frequently wrapped in tension bands. If I’d slip back into bad form, he’d nudge me, taunt me, push me, or surprise peg me with a tennis ball at 50 miles per hour.

At the end of every session, he’d recite his mantra, “practice doesn’t make perfect, perfect practice makes perfect.”

In 10th grade, everyone was surprised to see the waterboy turn into Aaron Judge. That’s a gross exaggeration, but really I made the starting lineup, batted 2nd, and had the highest average on the team. It came out of nowhere; no one saw the ~300 swings per week under Fat Joe’s supervision. I never played baseball again after that breakout season—thanks to a freak snowboarding accident that broke my arm completely in half—but I learned something more valuable than a swing: mastery doesn’t come from repetition; it comes from targeted, corrective repetition. If you want to get really good at something, you don’t just show up for a scrimmage every week, you find a coach to show you what and how to practice.

The idea that 1-on-1 instruction could turn the average kid into the leader of the pack isn’t a new idea, it’s the conclusion of Benjamin Bloom’s research. In 1984, he found that students with a tutor scored better than 98% of kids who learned in a conventional classroom model. Bloom titled his paper The Two Sigma Problem to emphasize the challenge in finding a scalable, cost-effective way to replicate the effects of coaching.

For almost five years now, I’ve been a developmental editor—I work 1-on-1 with writers to bring an idea to its peak form, and to help them see the patterns in their prose—but there’s a limit to the number of people I can help. The last year has been a blitz to code everything I know about writing into a single app. Today I’m excited to announce that the Essay Architecture app is live.

Find the invisible patterns in your craft:

EssayArchitecture.com

Unlike most AI writing tools—which are inevitably slanted by markets to become autocomplete tools for businesses—the mission here is to make something that helps you improve. This is an educational tool, not a ghostwriter: you can’t talk to it, you can’t ask it questions,2 and it definitely won’t write your sentences. It does one thing: it evaluates your uploads and offers insights into your craft. This is built for a subset of writers who publish online, respect the process, and know the value in being able to compose a great essay.

Think of this like Fat-Joe-as-an-app but for essays: it gives you a holistic evaluation of your writing mechanics, it finds your weaknesses in technique, and then gives you specific guidance to improve.

This will not automate, accelerate, or simplify your process; it will guide you through the labyrinths of editing that you typically avoid. At a minimum, it gives you actionable feedback; and if you’re a paid subscriber, it gives you “editing lenses” that isolate one pattern at a time. Instead of reading from the top and hoping you’ll find ways to fix your draft, you could try squish-the-bug-style editing drills. What if you only workshop the opening sentence of each paragraph? What if you read it out loud and edit for sound? What if you put every sentence on its own line, read the right edge, and edit for rhythm? What if you scan for concreteness, making sure each paragraph has an image, a reference, or a personal experience?

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For a computer to analyze your techniques and make recommendations, it requires quantification, and I imagine that could bring up trauma from your school days. Do essays really need to be scored through a shared standard? The critical nuance here is the Paradox of Standardization: the right kind of standards enable customized learning at scale. It’s possible we all hate standardization because we’ve been trapped in boneheaded systems. A bad standard prescribes a specific form (like the ‘Five Paragraph Essay’), while a good standard describes the nature of a solution, allowing for creativity and variety. Also, a standard is only useful to the degree that it shares granular sub-scores that enable specific learning paths. It should be less about ‘judge my skills’ and more about ‘show me where to focus.’

When you try the app, you’ll notice a pattern score comes in every 45 seconds, and you’ll naturally wonder, can I trust these scores? Large language models are dubious judges of quality. Even though training runs have exposed them to trillions of words, including all of the classics, it does not know what is “good,” only what is probable. Experiment with ChatGPT, and you’ll notice that it loves slop and it can’t reproduce its scores: if you feed it the same essay multiple times (in separate windows), and ask for a 1-5 score, you’ll get scattered results: 3.25, 2.75, 3.45. However, if you significantly narrow the scope, AI is powerful at analysis. For example, if you give o4 just one paragraph and a specific rhyme analysis algorithm, it’s precise and repeatable.

Why the discrepancy? It’s counterintuitive, but the more context you give, the less reliable its judgments. Since the latest models have million-token context windows, writers are quick to upload 10,000 word style guides and example libraries—but actually, this is bad practice. The Context Rot paper (July 2025) showed that the reliability of semantic analysis dramatically drops after 1,000 tokens! This means a single essay is usually too big to meaningfully process. To address this, I built Essay Architecture in a way that’s fundamentally different from ChatGPT, Claude, or Gemini: it breaks your essay down into smaller units—paragraphs—and runs 1k-10k atomic evaluations on each upload. Each of the 27 patterns has its own algorithm, and I rigorously test these to see if it matches my own scores and intuition.

Sounds neat, but does it actually work? My goal by EOY is to have public metrics so you know exactly how much you can trust the system. For now, I have rough estimates. The Precision Score is ~96-99%, meaning you get results within +/- 0.1 if you upload the same essay twice (Claude scores ~83%). The Accuracy Score is ~73-91% (compared to Claude and ChatGPT which scores in the 60s). What this tells me is that Essay Architecture thinks in a semi-deterministic way, but there’s still a lot of tedious testing I need to do for it to match my control set more closely. I still need to establish a Feedback Score to measure the usefulness of the suggestions, along with a Slop Index for each pattern. The goal is to keep improving this until it can reliably guide anyone from a first draft to the best thing they’ve ever written, repeatedly.

What are the implications of solving Bloom’s Two Sigma Problem for writers? It could mean that someone’s slope of progress could radically increase. Less writers would give up. It would take a skill that seems impossibly difficult and make it manageably difficult; always challenged, but never confused, never hopeless. Regardless of our escalating slopfest, it is a good thing to bring more people onto a quest to master something. By approaching mastery, you cultivate a transferable skillset—including discipline, focus, presence, patience, resilience, and determination—that touches areas of life well beyond your domain. We should shift our question from ‘what happens if AI makes masterpieces?’ to ‘how can we build AI to train a new generation of masters?’

This is the mission of Essay Architecture. I’m two years into this, and there’s still so much to do, fix, and build, but it’s great to see it helping writers already. Here’s my first (unsolicited) testimonial:

“I uploaded my first essay to your software yesterday. I used a Substack post I wrote a few months ago that I was quite proud of and others enjoyed. And...your software tore it to shreds! For 2 minutes I sulked defensively...then I went into learning mode. It’s truly a great tool and you should be proud. I woke up this morning with a flood of ideas on how to improve it, which on a higher level is giving me more insights about myself. Thank you for the invitation/challenge to try it!” – Bob Gilbreath

And here’s another:

“Mind blown. I just got the best essay feedback I’ve ever received and it didn’t come from a person. It came from @MichaelDean_0’s Essay Architecture.” – James Vermillion III

If you’re curious to see the invisible architecture behind your essay, you should give Essay Architecture a try. It’s only $9. And if you like it, you can get it for as low as $2/draft when you buy upload credits in bulk.

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Thanks again for being a reader of Essay Architecture! This post marks the beginning of a platform, and so here’s the range of things you can consider doing:

• First, check out the new website.

• Buy some upload credits ($2-9) and use the app as your essay coach. If you want to share feedback (bugs, feature ideas, testimonials), you’ll find a “Contribute” icon on the right of the website’s navigation bar.

• Write the best essay you can and submit it to the Essay Architecture Prize to win $10,000. The deadline is November 23rd, 2025.

• Become a paid subscriber and unlock the textbook, which includes 24,000 words on a pattern language for essays, and will soon begin updating with examples ($10/month)

• Join Essay Club to start a long-term writing habit ($300/year)

• Read the mission statement and share feedback here to help shape it.

Leave a comment

Footnotes:

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• Two week ago, I announced I’m giving $10,000 to the best essay of 2025. The competition starts today! Below you’ll find the prompt and some details to help you get started. I’m putting some final touches on the software & submission tool, so expect that to come out by the end of this week. In the meantime, you can start brainstorming and drafting your ideas.

• The Essay Architecture textbook is live on Substack! This has been two years in the making. Paid subscribers now have 40 posts that cover every element and pattern of the system in detail. Free subscribers have access to A Pattern Language (an introductory essay) and the dimension pages, which give an overview and all the definitions.

• Check out my episode on Infinite Loops with Jim O’Shaughnessy for a conversation on Essay Architecture, this competition, writing, technology, and education. Big thanks to Jim, for the O’Shaughnessy Fellowship made this all possible (you should apply in 2026).

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The prompt:

What’s it like to live in 2025? Write an essay about a specific moment you experienced in 2025—an event, trend, media, technology, or relationship—that exemplifies both our current zeitgeist and our timeless nature.

I figured since you’ll be spending hours writing your own essay(s), I’d spend some time articulating the prompt, why I picked it, how to approach it, what we’re judging on, and a summary of the rules. There are also 50+ examples in the footnotes that might help you generate ideas. If anything isn’t clear, please leave a comment! (I’ll add a “clarifications” section at the bottom.)

Why is this the prompt?

For an essay contest to be “open,” the prompt needs to be flexible enough for any writer to enter. Something obvious we all share is this specific moment in time. 2025 can unify a big range of very different essays. Our goal here is to publish 10+ finalists into an anthology; not only will it be a collection of solid essays, but also an artifact to make sense of the spirit of our times. Sense-making is hard in 2025: the open Internet is chaotic and polarized, and institutions have fixed ideologies. The hope is to curate a collection of independent thinkers who use personal experience to make sense of our society.

How should you approach the prompt?

Approach “2025” in an angle that is most exciting for you (a prompt is really just a launch point that you should quickly abandon once you find inspiration). You do not need to tap into pop culture icons, or polarizing political ideas, or what you think everyone else collectively thinks this year is all about. Go deeper than hype and headlines. What feels significant to you this year, and what might that reveal about our culture? It’s okay if it’s extremely subtle and unexpected. Don’t feel the need to make it explicit (“I think the most defining moment of 2025 is X because…”). The prompt should be invisible. You need not even mention “2025” once. I also don’t recommend trying to summarize the entire year, month-by-month. Pick one moment and go deep.

I’ll share two general ways to approach the prompt (and really, essays in general). An essay is a personal reflection that links individual experience to socially relevant ideas. You might begin with the particulars of your own life, or, the broader patterns of culture, but eventually you have to bridge the two. An essayist fuses many genres—the pen of a poet, the imagination of novelist, the persuasion of a marketer, the research of a journalist, etc.—but most fundamentally, it fuses the soul of a memoirist with the insight of a philosopher. It’s about using your own life as a portal to understand bigger ideas.

1. Start with experience: What are some notable things that happened to you this year? These could range from obviously important life events to peculiar moments you can’t stop thinking about. What can you write about that almost no one else can? By starting here, you’re guaranteed to write something singular; the task then is to figure out how your experience is emblematic of a larger phenomena. Is it totally okay if your topic is not self-evidently symbolic of 2025. By getting into the specifics, you might reveal an unnamed current that we’re all entangled in. (Examples in footnote.1)

2. Start with culture: What are some phenomena in the larger culture that you have a unique relationship to? Whether you cover a massively mainstream moment,2 or a little-known event in an Internet subculture,3 it’s all about finding an idiosyncratic angle. It’s less about picking “the best” or most representative moment; it’s about finding one where your singular experience gives us the best lens to understand it. Whether you’re writing about politics,4 media,5 technology,6 language,7 or another domain, make it yours.

What are we judging on?

There are three ways your essays will be evaluated: (1) the Essay Architecture framework will judge how well-rounded your composition is, scoring your submission 1-5 across 27 objective patterns; (2) the best-crafted essays will be read by a panel of human readers who look at 8 subjective criteria (listed below), because the quality of a work is more than the quality of its craftsmanship; and (3) a guest judge will serve as a wildcard, ranking essays based on their own taste.

Objective criteria:

To get a basic understanding of the Essay Architecture framework, you can check out my latest posts on Idea, Form, and Voice. In each you’ll find a short essay on the dimension, along with a one-line question that defines each element and pattern. It’s around 2,700 words total (which is far more descriptive than most essay prizes).

Subjective criteria:

Now, here are some subjective qualities of a great essay. (I’m sure these will evolve with time.) A great essay is not just well-composed, it’s singular, emblematic, timeless, catalytic, essayistic, emotional, experimental, strange, etc. These are less definable through patterns on the page; they’re felt by the reader, and colored by their experiences.

1. Does the essay seem to come from a singular life circumstance?

2. Does an insight reveal something surprising about 2025?

3. Has it connected a timely moment to timeless themes?

4. Is the core insight likely to provoke change in thought or action?

5. Did it capture the essayistic spirit: a mind working through friction?

6. Does it pack powerful emotions?

7. Does it push the boundaries of prose and experiment with craft?

8. Does it make the familiar strange?

General rules:

(Detailed and boring terms coming soon)

• Open eligibility. Open to anyone 18 years or older (ages 13-17 require parental consent); open to most locations (unfortunately certain countries with US embargoes might have complications); pseudonyms welcome.

• $10k grand prize and 10+ finalists get published. There is a single cash prize, but the finalists will be featured in an anthology with a royalty split.

• Upload for $2-9 to get feedback and scores, then submit for free. Unlike traditional contests that charge a ~$24 submission fee and don’t offer feedback, the Essay Architecture software gives you a detailed analysis of anything you upload.

• Unlimited submissions. You can upload as many drafts as you want to improve it through feedback, but I recommend submitting one version per idea. But feel free to submit as many different ideas as you’d like for consideration.

• Written or published in 2025. Along with new, unpublished essays, you can submit anything you’ve written or published in 2025. Feel free to submit any of your existing Substack essays that relate to the prompt (you can edit them or submit as is).

• Flexible word count: Open to both short and long essays. The max word count is 10,000 words, but focus on quality, not length. It’s better you submit a 1,000 word essay that is dense with meaning than a 5,000 word essay that is ambitious in scope but poorly crafted. If you exceed 2,500 words, make sure the form/structure is tight.

• Blind judging: Your submission will be given a random ID number so that readers won’t be able to easily identify you. But since these essays will have personal elements, there’s a chance they might. If they think they do, they will guess who the writer is, and if they’re right, their evaluation will be down-weighted or omitted (you will not be penalized; the scores of blind judges will just have more weight than non-blind judges).

• English language: All essays are scored and judged in English. If you are writing in another language, please translate before you submit.

• AI policy: Some competitions ban all forms of AI usage. Given that Essay Architecture is an AI-powered editor, I’m more open to it. That said, the spirit of this whole project is to preserve the act of essay writing (meaning, in my opinion, you should use AI to augment your thinking, not to automate your sentences). But however you use AI, it’s welcome, as long as you disclose it. For each submission, there’s a little one-view survey that asks you to share how influential AI was in various parts of your process. Usage will not be penalized! This information will help me see aggregate stats and shape a more specific AI policy in the future.

• Data privacy: Essay Architecture uses OpenAI’s API. Data you submit through this API is not used to train their models (unlike the conversations within their product, ChatGPT). Additionally, I do not sell data or use uploads to train my own generative models. A good rule of thumb is to not upload any sensitive data you wouldn’t want on your personal website (after all, this is a tool for essays that you will be sharing in public).

• Submissions close Sunday, November 23rd, 2025: Submit early to avoid any last-minute technical issues! In case everybody procrastinates and there’s a final-hour surge that melts the server, I will provide a backup submission portal through Google Forms.

Examples

Welcome to Essay Architecture. The essay below, “A Pattern Language” is a good introduction to this framework. All of the dimension pages (Idea, Form, Voice) are available to free subscribers, while the element and pattern pages are for paid subscribers. Each pattern page includes an overview, why it matters, an example, how to implement it, scoring criteria, and related patterns. The goal is for this to be a “living book” that gets populated with new examples each month.

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An essay is consciousness frozen in words; it is an artifact that captures the thoughts, feelings, and events that transpire as you explore and makes sense of an Idea you care about. There are no rules or limits on what’s worth writing. An idea can be driven by a question or story, a dilemma or theory, a rumor, argument, confusion, war, childbirth, accidental psychedelic experience, dog euthanasia, economic indicators, toothpaste conspiracy theories, etc. It can be today’s shower-thought, yesterday’s grievance, or an idea that’s haunted you for a decade.

I hesitate to offer any prescriptive method on “how to come up with good ideas.” Sometimes they come from the belly button. My best recommendation is to write down every mild epiphany you have, ideally in prose, ideally legible enough to share with a friend, ideally 3 times per day, and if you’re crazy and jobless, 100 times per day. I’ll say this: don’t write the ideas you think you need to write about; write down what’s already passing through your mind. The best ideas come from paying attention, from patient, endless probing.

So while the idea of starting ideas is unsystematic, mystical, and mostly random, I do think there are learnable patterns in how you articulate the thing in your lap. A fisherman can go on adventures of endless variety, but there are only so many ways to skin a fish.

You can think of an essay as a collection of little ideas (your Material (1)) that all work together to support one big idea (your Thesis (2)), that you eventually compress into a crystallized idea (your Title (3)). Geometrically, ideas are about centrality. A bunch of planets orbit a central star that has to be named.

You can start at any scale. Sometimes you wake up from a dream with a Title that jingles. Sometimes you have a weird, specific Thesis (ie: the sitcom Seinfeld marked the decline of western civilization) but don’t have any evidence yet. Sometimes you collect a mosaic of Material that all seem connected through some invisible web, but you have to write to find out why.

Regardless of where you start, there are two opposite modes that help you sift through an ideascape: divergence and convergence (coined by JP Guildford in 1956). To diverge is to be open and open-minded, to chase down tangents, to imagine a world of potential in even the stupidest detail, to drop all filters and see how any thing connects to everything. To converge is to be a ruthless editor. Through divergence you discover a better center of gravity, and through convergence you let go of anything outside of its pull.

It is natural to fall in love with your own ideas, but you will have to delete a lot more than you write. An essay is not a chronological record of your thinking. Drafts are meant to be shed. Writing lets you explore the edges of your terrain; but once you’ve become a parkmaster, it’s your job to pick one landmark for someone to visit. An essay is an opportunity to share a single idea at max potency. Do not try to put the whole park in prose. You’ll kill the trees. The goal isn’t to see how much you can cram (word count is not impressive); the goal is to reach the highest possible density of meaning.

The good news is, all the ideas you cut from your current essay are seeds that can sprout into future essays. Unlike books, you’ll be able to produce many essays in your life, so have faith that each idea will have its moment. Let each one breathe, and use hyperlinks if you must. Pick one idea and take it seriously.

When ideas are properly scoped and sculpted, they become linguistic viruses that enter and change the mind of the reader, so write responsibly. By unifying a multi-dimensional range of material around a kernel of truth and giving it a name, you give somebody a new lens to their reality. The essay is folk technology that turns human experience into transferrable wisdom. We could use some of that.

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