michael-dean-k/

[I] It feels noble to make big commitments, to vow to keep up some lifelong habit—but actually, mutation is better. I often try to kickstart these weekly publishing streaks, yet they always fizzle. I appeared for three weeks and then disappeared for four. Zoomed in, I feel overambitious and unreliable. Zoomed out, I've published a million words in five years and never missed a month. To clarify this into principle: it's worth being stubborn about the high-level goal you'll tirelessly pursue, while being scrappy, experimental, and non-sentimental in your methods; keep the Streak (deep time is the muse), but stay flippant and agile in approach. "The voyage of the best ship is a zigzag line of a hundred tacks. See the line from a sufficient distance, and it straightens itself to the average tendency. Your genuine action will explain itself, and will explain your other genuine actions. Your conformity explains nothing" (—Emerson, Self-Reliance). The easiest way to die a slow creative death is to chain yourself to arbitrary rules of your own making until you dread showing up. Why publish every Saturday? Why only write 2,500 word essays about [gloop]? Break contract, leave the plateau. Break the bonds of language, and speak in erotic grammars (Ferlinghetti). Why not devolve into tongues and alarm everybody once in a while to shake expectations?  (...Speaking of tongues, speaking in tongues is top of mind because yesterday while talking to Claude about The Dead Sea Scrolls, it spontaneously slipped into Aramaic, or Enochian, or some demonic language, sounding like moans slitherings in reverse for 15 seconds, before snapping back into Water Cooler Seth voice—"is there an angle you'd like to dive deeper on?"—denying it ever happened...) ... [II] Why even use paragraphs? Me more than anyone could lecture you to the edge of a cliff on why the visual separation of ideas is a common courtesy that let's reader grok the shape of your thinking. Do I have the guts to send out a 10,000-word wall of text, an immense density of non-sense? ("Why are you such cowards? Don't you have any trust yet?"—Mark 5:39). Is this even about guts? For this particular essay—yes. I'm in need of a risk, of a shock, to bathe my meek constraints in acid and see "skies split apart" with new eyes (Mark 1:10) while caring little of being watched. Also, this feels like (a) the honest shape of a single-breathed composition, (b) a reaction to the one-lined paragraphs of copywriting, the wave of machine-enhanced readability, (c) the symbolic death of my listicle template that's shaped the last three editions here ("you're a writer, not a listicler"—wife, just now). Really though, it's Friday night, a night of metanoia, and with a howling storm outside I'd rather channel attic spirits than give you bullets to promote my business. Here lies my tension! ... [III] I've snipped the collosum. What I mean actually is this: I've divided my writing into two halves; michaeldeank.com is where my creative writing now lives, and this Substack, in theory, is where I tell you about Essay Architecture in a register that's practical, focused, and non-alienating. In some ways, this divide has been working well— creatively: I'm reading wider than I ever have, I'm ghost-publishing 15-20 essays per month, and am experimenting hard (I write blindfolded on a typewriter and am 32,000 words into a rewrite of the Odyssey); I've  forgotten the hallways of Notes and instead commit to a private practice that will shape who I want to be next decade ("We must do like the beasts and scuff out our tracks at the entrance to our lairs. You should no longer be concerned with what the world says of you but with what you say to yourself"—Montaigne) <THUNDER, RAINPRICKS, CHILLS>; business-wise: Essay Architecture is grooving: the Club is growing, I'm loving the weekly cadence of classic deconstructions, and I've just built myself the ultimate reading tool that let's me route pattern insights in a way that will transform the textbook and feedback software—yet something's off. My issue: I feel unable to quickly and authentically communicate all that on a stage like this ... [IV] Before I unpack my self-consciousness, I'll take a dinner break, for the rotating delivery man arrived with our Thai. Our exchange rituals have gotten odder; we rarely speak the same language, and now the network we use requires me to recite him a string of numbers—5156—to confirm I'm the receiver. Mediated by machine, face-to-face, yet we interact in arbitrary digits as a form of synthetic trust. Strangers are tangled in algorithms, and I can't help but see the parallel to Substack. [V] It feels like my creative work is veering "schizophrenic," Essay Architecture is inherently "autistic," and it's becoming hard to make the flip and distill both or either mode into a casual email update. A trusted friend warned me against using psychological conditions as metaphors, and I agree, so let this be the first and last time I use them. For me, these labels work together as two opponent types of information processing: the schizo connects everything to everything and follows a seemingly bizarre stream of associations; the autist creates specific boundaries, detects granular patterns, and zooms in to carve the quadrants of a pinhead. One flitters between fractals, the other fracks the fractal. If I were less concerned about your attention and your impression of me, I would just ping your inbox every day from whichever tree I happened to be stuck in (yesterday would have been an invitation to a Bible study group). But readers are fatigued. I'm fatigued! I confess I've mostly stopped reading Substack in recent months—I mostly bookmark... these days I read older things, but in September I'll devise a plan to somehow assemble and read all of 2026's best Internet essays—and so instead of publishing essays here, I figured I'd try to curate myself. I can still certainly do that, give you the best ofs each week, but I feel Substack isn't the place for digest; I already have my own site to be wild within, and so if I'm to show up and publish somewhere else, I might as well conform to the customs of the channel. [VI] I'd be dishonest to deny Montaigne's influence on this digression. I've been reading through Screech's selections the last few months, intrigued by his rambling essays: "I am unable to stabilize my subject: it staggers confusedly along with a natural drunkenness. I grasp it as it is now, at this moment when I am lingering over it. I am not portraying being but becoming: not the passage from one age to another but from day to day, from minute to minute." He's doesn't stay on theme or revolve around a thesis, nor does he care to write perfect compositions that a mass-readership can consume without friction. Instead, he wants to understand himself; he describes his idle mind as, "[bolting] off like a runaway horse, [giving] birth to so many chimeras and fantastic monstrosities, one after another, without order or fitness." It's a style of composition rooted in endless forward momentum. There's something to this spirit! It doesn't replace the art of reigning in your found beasts into a well-ordered whole. Chaos and order aren't opposites, but beginning and end of a circle. [VII] I've once said that "you write your first draft to find ideas for yourself, and you write your last draft to convey those ideas to a stranger." My core revision is to not hoarde your first drafts. Editing is worth doing, worth loving, but not every dingleberry can be refined through your most precise discernment. There's probably something to writing and sharing first drafts that are imperfect, enjoyable, and do the real job of surfacing new ideas. Most of what's in here will never be touched again, but I imagine a few might re-emerge into a future constellation I can't yet see. I can probably write 250 spontaneous essays in a year, but can probably only compose 1 or 2 great essays in that same time. An even older metaphor I've used around this is "the fish and the whale." Both live in water, but one is for your daily sustenance, the other is an epic chase. Do both. If you only fish, you'll have nothing remarkable to share, no legends to pass down; if you only whale, you starve. [VIII] What I haven't revealed yet is that this whole essay was written in a one-shotted Fable prototype—a vision I've had for a while called "margin muse." As I write, old notes, old logs, old essays, all emerge on the right side, based on semantic similarity. It's one of my favorite uses of AI, because I still do 100% of the writing; all technology is doing is connecting my emerging sentence with the backlog of everything I've ever read and written. It's a mechanical subconscious, a perfect memory. Surely there will be side effects? It takes time to become "numb to the structuring effect of a technology," to realize the hidden the "auto-amputations" (Dennis D. Cali, Mapping Media Ecology). It still feels like I'm in control of the composition: I mostly ignore the sidebar, and only peruse cards to take breaks; my natural subconscious still feels like it's guiding the amble. So maybe this a decent example of a mechanical and organic subconscious working together. I'm using the word "subconscious" a lot here, and this metaphor might be off, but I consider LLMs to not be consciousness at all, but rather a massive mechanical frozen subconscious. [IX] Here's what I mean: AI is language turned into geometry. As transformers ravens through NYPL-scale archives from data centers, they slice ideas into little packets and turn them into mathematical coordinates. Imagine every Kindle highlight translating numbers: [0.3982, -1.2098, 04983, ...]. Similar concepts are plotted near each other in this XYZ space (the kicker is these coordinates run-on for 700+ dimensions, making an LLM a mathematical hyperobject that we can't rationally understand). So every time you prompt or write, that idea also becomes a coordinate, a probe into a complex shape, a fisherman's hook testing a specific pond on a boundariless map. This is of course an oversimplification—"next token prediction" (prose) and "semantic search" (2nd brain) work very differently—but the key similarity is that language is geometry. [X] There are different ways to model our subconscious: Freud thinks its all sexual, Jung models it through archetypes; but a geometric model comes from a Czech LSD psychotherapist named Stanislav Grof. In Realms of the Human Unconscious," he proposes an idea that memories are organized around COEX chains, or clusters of "condensed experience." In childhood, a distinct emotional experience establishes a COEX somewhere in geometric space, and further experiences will locate  we have some. So during his thousands of LSD psychotherapy sessions, before that was illegal, he noticed that it enabled him to more easily to get down to the root of a COEX, as well as make associations between them. I may be butchering his theory in some significant way, but the critical thing here is the distinction between LLMs and COEXs: a synthetic mind can cluster information through logical meaning, but a human mind clusters experience through emotional valence. [XII] This is the limitation of Margin Muse. It might be able to transfigure idea into 700-sided dice, but it's numb to how they actually feels to the author. They might know ideas A+B share some latent theme, but not that A+C similarly embarrass you, or B+D similarly amaze you. And so in tandem with building logical systems to map essay structure and organize some hyper library, I am starting to dedicate more time to the irrational. Maybe you've scene the show Stranger Things where Eleven blindfolds herself, sits in a bathtub, and emerges in a different dimension. What is that for writing? [XI] I wrote around 7 essays in early July with my eyes closed. This is an odd experiment, but to summarize: I want to escape literacy and shift my mode of writing from 'reading' to 'seeing.' We typically read when we write. I'm watching letters clump into words, and very frequently as I write, I go back to the top to re-read to remember where I started. Operating with language cuts you off from the imagination, I think—perhaps it's why kids loose imagination as they become more literate. There's a separate pre-cultured state of mind that is more prone to dreams and hallucination; sometimes I can not only see a lucid image in my mind, but it starts to self-transform, taking on a life of its own, shifting from one thing to the next, whether beautiful or terrifying. So when my eyes are closed at a typewriter, I'm trying to see things, say them, and then transcribe them. There moments of drivel, and some of primal excitement, but I did something new and didn't read them at all. They're stuffed in a drawer, and I have no idea what's in it, but I imagine some of my best phrasings ever are in there. I will eventually go back, pluck out phrases, edit them into a whole, and call it "Heatflash" (was written during a heat wave in early July). [XII] From an altered state like this, outside of self-censorship, you can stumble into modes of baffling surrealism. My alternate version of the Odyssey is coming together from a similar process of free-association, from understanding the latent possibilities in each of the characters or worlds, and the chain of details got a friend to ask me "are you okay?" and also "you should submit this to Playboy": the escape from the drunken cyclops's cave by tying his limbs to the boulder and castrating him (relating to Hesiod's origin of Greek mythology, a castration); specifics on the sexual mechanics of Circe and Calypso (Circe can swallow Odysseus’s seed and shapeshift into Penelope, which is why he stays for a year; Odysseus only has sex with Calypso once, but it's a time-dilated extended orgasm that lasts 7 years, which lets him experience a tantric hive mind of all orgasms across Greece—a kind of "remote viewing through lust”—, which is how he learns of the suitors banging his servants, and of Penelope's chastity—he only agrees to sex with Calypso for the intel/recon, not knowing a single moment would last so long, which is why he weeps); his overstay in Hades lets him discover the judgment of souls, which, along with Achilles's blood-mouthed confession, triggers his own internal crises of morality; his multi-week extraction of knowledge from the Sirens ("Zeus's plan" for world peace, the omega state (the entire future), and yet also, news of Telemachus’s assassination plot); the spontaneous and bloody rampage of Telemachus after his father’s return (against his father’s wish), which explains the hanging of the maids; Calypso's curse, causing Odysseus to see any mortal woman he penetrates as a skeleton; his appeasement of the mob at Ithaca with his ultimate knowledge from the Sirens, him taking credit for Telemachus’s rampage, and for his own imprisonment as an oracle; Telemachus's rise into a tyrant from having total knowledge via his father (but the knowledge becomes more useless the more they act on it; the arrest of bards, oracles, and soothsayers to regain knowledge of the future (and blinding them to heighten their divine vision, including Odysseus); Penelope's calm and principled suicide, walking into the sea with iron boots, knowing she will receive a favorable judgment in Hades (Odyssey only tells her that secret); the arrival of Telegonny, the son of Odysseus and Circes—an exact clone of Telemachus, but ~15 years younger, with identical voice—, with the goal of restoring order in the universe (the Gods are threatening to retreat into the cosmos and leave the humans behind), by killing his father and step-brother; a scene where blind Odysseus hears two versions of his son talking and thinks he's going mad; Telegonny shapeshifting his father into a pair of floating hands, then stabbing and killing him with a mantid spear (his inevitable "death by sea"); a final scene in Hades, where Persephone sentences Odysseus to write about his journey (an anachronistic ability he stole from Sirens to capture the knowledge of the Sirens), which is a meta-fictional move explaining why the whole version is written in a 1st-person Montaignean style; and once his essays are written, Persephone sends the book on a ship back to mainland Greece to warn humans of Faustian appetites, and then releases the Gorgon (Medusa) on Odysseus, freezing him into stone, the ultimate consequence and destiny of a restless wanderer. [XII] What's the central thing I'm getting at in this wall of text? ... (this is the point where I pause, and back out from sending it 8,500 people) ... [XIII] The whole genesis of this thing was a crisis in not knowing what I want to send to "the main list." Publishing on my website is joyous, easy, and unhinged—Substack gives me paralysis. This isn't surprising; it more so reveals my preference for privacy, my reservedness, my discomfort at the center of attention. But I need to send SOMETHING, and given that my personal website is a place without filter, it feels irresponsible, even weak, to treat my Substack as an amorphous, aimless place. The whole impetus of making a separate home for anarchy was to feel better about having a Substack that was focused, value-centric, business-driven. It childish to completely give in to the creative spirit and sabotage the business half of things that enables the creativity to sustain. I do think it's the right call to NOT send this. I love it, and it belongs here, on my site—I will try again to send something next week; the goal is to tap into the spirit of fun, but focused around Essay Architecture, as a project. I need to find some middle ground between neutered listicles and 3k-word walls of chaos.

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

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

1) Does this kill discovery?

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

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

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

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

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

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

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

Grasping at a solution_

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

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

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

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

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

Website as gamified maze?

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

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

Chris Best, founder of Substack, posted that they caught “President Plump,” the #1 growing account on Substack, for using fake subscriptions to boost discovery. I think this was intended to comfort everyone that they caught a scammer (justice!), but actually it confirmed what many were starting to notice: discovery is contingent on you making money. If you have paid subscribers turned off, no algorithmic wind will blow your way. But if you have a spike of paid subscribers in a month, suddenly your old posts will start to go viral, in hopes that even more paid subscribers will bring the platform 10% (this has happened to me before). This isn’t inherently bad. For every President Plump, there is an earnest person trying to finance their creative project.

But at scale I fear it creates a bad pattern, because the accounts that everyone sees will be the ones making the most, and generally these will be marketers and growth hackers more than artists. I think you will find better writing in the gutters of Substack than on their rising leaderboard. If authentic culture emerges outside of monetization, then there’s a real rift between what Substack wants to be (“an engine for culture”) and what it actually is (an algorithm that only rewards monetization).

I think the best we can do is use this information to our advantage. For example, I could have new Essay Club members pay directly through Stripe, but by handling payments through my Founding Members tier on Substack, I get a discovery boost, which is worth the 10% fee. Similarly, if you make small digital products, it might make sense to bundle them into a subscription instead of charging per item.

Should you use a credit card masking service to give yourself 20 paid subscriptions for $5 each? Depends. Basically, for $10/month, you can pay for a probably noticeable increase in discovery. The question is, will you get caught? Maybe they are on the lookout now, but my guess is they would only penalize it at a certain scale. Sam Kriss speculated that President Plump was paying himself around $5,000 per month to reach #1. I’ve never done this, and wouldn’t necessarily recommend it unless you have a hacker mentality and really need the growth. 

At the very least, you should consider having paid subscriptions turned on. Cate Hall found success in charging $1/month and getting to #1 rising. Our very own Yehudis Milchtein also set up $1/month subscriptions and is now #91 rising in literature.

However you approach this, it brings up a bigger question for me on how to build a real engine for culture. It seems like you can’t have an algorithm for a single reward (popularity or money) or else they will be gamed; instead you could give everyone curatorial power relative to their cultural reputation, however you measure that. For example, if we all trust Ted Gioia, then somehow Ted’s like should count more than 10,000 bot likes or $1,000 in fake subscriptions.

I hope this triggers more transparency from Substack on how their algorithm works, and also hope for a new generation of platforms where each person has visibility into and control of the thing that is routing them information.

A few days after my daughter was born, I had something which I’m describing as “phantom infant syndrome.” When I was away from her, holding a phone, or fork, or some other manufactured object, I’d get a tactile hallucination in my hands of the softness of her skin and hair. I imagine this is nature’s way of saying go be with your kid (made possible by mild sleep deprivation). And so this is symbolic of one of the many biological drives pulling me away from writing in recent weeks.

This is happening around my five year anniversary of being online, and it’s probably the longest stretch I’ve gone without having urgency to do so. It’s probably healthy and helpful to be relatively non-linguistic for a few weeks, once in a while (I usually write on vacations, so I never really take breaks from it). We’ll see. It’s possible that I’ve thought myself into a trench, and the best way forward is a proper break (I have once said the best editors are friends, time, and weed—although less weed in recent years). Now that I’m immersed, familiar, and comfortable with the rigamarole of infant care (and all the wonder it brings, too), I feel bandwidth opening to write, and I’m curious to see how my practice takes shape from these new constraints. There are real deadlines now. Baby wakes up in … 30 minutes … and I’d like to post this by then.

Last weekend I read through all my writing from 2025, and after the typical EOY reflections and word count calculations, I realized that something has to change. So I published 12 essays, 10 about Essay Architecture, totaling at ~64k words (re: the other two … one was a first-person TikTok odyssey, the other was about the role of psychedelics in evolution). But I also published 150k words in logs, 2.5x the volume. Logs are notes to myself, mild-epiphanies through the day written in complete sentences, all ghost-posted to a monthly Substack post. Unlike my focused and convergent writings about EA, my logs are far more random: recurring topics included the Grateful Dead, movie reviews, notes from a day at the zoo, dream journal entries, usage debates, new architectures for social media, overheard conversations, etc. My logs, in theory, are a low-stakes breeding ground for essay ideas to emerge, but given the demands of my other projects (the textbook, software, and essay prize), my logs stayed unread and undeveloped last year. Now, with parenting in the mix, it makes sense to me to stop logging, or at least, reconfigure it.

Over 4 year, I wrote +8k logs, added to the archive on 95% of days (avg. 5.6 per day), and the whole archive is 650k words. It’s a very personal corpus, one that documents my thoughts and life at a sometimes OCD-level of detail. I thought I’d do this forever, and it sort of stings to stop. I guess I’m not “stopping” as much as setting a stronger filter: I can still capture whatever I want, but I can only save whatever I publish on Notes. I used to argue for the importance of having a low-visibility space where you can publish whatever you want without self-consciousness or the need to set context with strangers, but maybe that’s a luxury I’ve outgrown. This is perhaps a long-winded way to announce something that probably doesn’t need announcing: expect to get a lot more diddles and spontaneous essays like this in the Feed. I figure my email-essays can be more on topic (I have a few slotted for January re: Essay Architecture, the club, and visual breakdowns), while these can be chaotic.

Technically, I’m still logging, but it’s for my daughter and those are private. Every day I write simple journal entries or letters about what happened. I figure one day, when she’s 15 or so, I’ll just hand over The Files and blow her mind. My dad did this for me: a few years ago, after my nephew was born, he sent me 8k words from my first 4 years. It was uncanny to see that he had a logging impulse too, and to learn about all these small events that everyone in the family would have otherwise forgotten (things that were not captured in pictures, like me trying to brush the teeth of stray cat). All this reminds me that writing isn’t just an act of thinking or communicating, it’s an act of memory.

I’ve been reflecting on how my writing will change once I have a newborn, and I keep coming back to this idea of releasing a “monthly EP of essay demos.” This means that I’ll send a post with 5-10 links to other essays that I “ghost posted” (publish without sending) earlier in the month.

I currently only have the S and L lanes of writing working. Either it’s a 2-minute log or a 20-hour essay. The goal is to prioritize the M (medium) lane, a 2-hour essay; instead of sending them out in real-time, I’ll batch them and let readers click into the topics they want. Feels like a strategy to be more divergent, more experimental, less formal, without overwhelming people and confusing them from the core mission of Essay Architecture.

I had Coco read through a week of my logs, and she shared three patterns she’d want to read more of: (1) unique, vulnerable experiences that show conflict and inner struggle; (2) lens on for self-improvement regarding life or writing; (3) culture commentary that helps make sense of big ideas. She was less interested in technical topics, or hypothetical scenarios (such as trying to imagine the handicap we’d have to give tennis pro Carlos Alcaraz for us to have a competitive match in tennis). The beauty of the EP strategy is that it gives readers a menu, and each will have their preferences.

Just came across a smutstack in my feed, an excerpt by someone liked by someone I follow. It led me to find a logloglog style page with date-stamped entries; at first I was compelled by the formatting—timestamp, return, paragraph, return, timestamp, no lines and single paragraphs only … innocent stuff—but then I read the writing itself, about a girl with an evil boyfriend. Then I clicked into one more post (one of the not paid ones) and it was an essay about her inner monologue while giving a blowjob at a club, written with specificity and elegance, on how she can’t help but think about dramatic ways to kill herself in the act if it goes longer than 5 minutes. My first thought is that this is like Worst Boyfriend Ever, except from a woman who writes a lot better. Is it great? Possibly, I’d have to read more. The problem is, I don’t want to, and basically can’t read more. Almost everything is paywalled and I can’t help but feel conflicted in paying for good writing when it can easily be interpreted as paying for written porn (especially now that Substack badgifies this!). It is called “Girl Insides” and that suddenly makes sense. I have not thought hard enough about the complexities behind sex writing (writing it, reading it, anthologizing it) and how that interacts with the essay. As do most people, I naturally keep writing and sex in different silos, but if sex is one of the most fundamental parts of the human experience (given that, you know, that's where kids come from), it feels odd and puritanical to exclude it.

I didn’t realize that Substack is open about paying off-platform creators to join their platform. See their $20m accelerator fund. My quick understanding is that, if you make $X revenue/year elsewhere, they guarantee you’ll make that, and will make up the difference if after a year, you don’t. A friend thinks there’s an additional secret fund that pays bonuses for celebrities to join (ie: Dolly Parton, Charlie XCX). I was surprised by how articulate Charlie XCX was—I only have a meme-level understanding of her—but I suppose it’s possibly ghostwritten. Idk.

I don’t have problems with this, but what doesn’t register to me is why they wouldn’t allocate money to help the on-platform, original writers. Obviously, these kinds of things piss of 95% of their userbase. Even if there was something like $100-$1m for on-platform writers with audiences under 1,000, that would build a tremendous amount of goodwill. My guess (and fear) is that they have a business model blindness, and aren’t thinking along the planes of “what actually builds organic culture?” Instead, there’s a lot of rationalizing: “here’s why bringing Derek Thompson on platform is good for you” (but the obvious benefit comes from the 10% they get from DT).

It’s weird to me that in some sense I’m giving more to it’s existing writers ($10,000), than the platform that raised $100,000,000.

Even if a SM feed is filled with all of your favorite ideas, friends, and thinkers, it would still be poison from the sheer volume of randomness. Even the act of seeing two things in feed, forces you to shift from one context to another, forcing you to shift frames, destabilizing and disembodying you.

Alternatively, if you had a feed of a hundred things, but they all revolve around the same content, all spawned from a singular intention, I think it would be less dizzying; it’s more enables depth into your present, embodied frame. There is less of a “slot machine” effect. 

It’s not that feeds or algorithms are bad; they only became bad when they strip context. The logic of most feeds, however, do not care if you feel oriented. They have a simple reward function, show you as many different things as they can, to see which ones drive behavior. They are running a real-time self-adaptive experiment on your preferences, in the hope to discover which patterns might nudge you into their desired behavior (whether it’s towards an ad or towards an on-platform paid subscription by a beloved writer, they are effectively the same—it’s an algorithm that is not being real with you, and not respecting your attention).

I feel like a broken record in prescribing a solution, but it’s basically Plexus (RIP): show nothing until you post, and then from what you post, share a feed of semantically related posts. Substack, as a writing network, is a unique position to build this. It has a lot of long form content: not just notes, but essays, podcasts, and videos. It should be looking at the granular units, semantically embedding paragraphs, and then those become atomic objects that help populate the “semantic feed” generated after every Note.

So Alex Dobrenko started a new personal website (I will not link to it because it’s secret), but he sent it to me, so I spent some time on it and wrote him some notes, and then he wrote a reply post to me, and now I’m making a reply log to that (and upon re-reading, I realize it’s now a whole essay). It’s something like a semi-public letter exchange. 

Letters, emails, same thing. 

Similar to how the 20th century has books like “Virginia Woolf: The Letters,” I wonder if the 21st century will have “Alex Dobrenko: The Emails,” where his children posthumously assemble and publish all their dad’s best emails. ((Also, now that my cholesterol is borderline, and my daughter is on the way, I’m having new thoughts about preparing for my death, like “THIS IS DAD FROM THE PAST AND HERE ARE ALL THE PASSWORDS.”) Something about losing all my writing forever feels worse than dying. We eventually have to die, but you only lose your writing forever if you’re careless and lazy. Rant over.)

What I like about letters/emails over essays is that there isn’t a mass-market context, and so you’re writing for just one person. That’s good essay advice too (“write for one person”—we literally taught this in Write of Passage), but deep down, it’s hard to forget that you’re writing for all people of all times, especially if you are.

Recently I mentioned that I’ve spent 2 years nerding out on essay patterns (the objective stuff on the page), but I want to start thinking more about the process: how do I show up to write?

One idea is to start essays as letters to specific people. Eventually, that can evolve into something for the main list, but I don’t want to start with them in mind. I want to start with a specific problem in my life, and then, with a small group of people who relate to that problem. Any idea I have comes with a clear person in mind, someone who would probably be most excited to read it, and has all the context needed so I can avoid the bush beating.

If I want to write about Alternate Internet Communities and weird websites, I’ll write to Alex. If I want to write about the insanity of the Dark Enlightenment, I’ll write to Andrew. Theology to Taylor, Emerson to Will, Hope to Isabel, Fatherhood to Dan, Greeks to Chris, Dreams to Garrett, AGI to Davey, Architecture to Liz, etc. It’s also special to say, “I wrote this for you, and we should talk and get to the bottom of this,” and that could really change the nature of the essay because someone else is co-shaping it with you.

Alex brings up a good question: why doesn’t Substack feel like this? I have to think more on this, but I think the stage effect is still at play. If you have a 10k audience, it still feels like a megaphone, and when you’re on Notes, you participate in American Idol, again with new skin. It’s still the best town in town, and there are tricks (ie: set up an opt-in Section for experiments so you can have a “shadow audience” that’s 1% the size of your main one), but there’s friction in tricks like that. It’s not the main way the platform is intended to be used. It’s meant for loud, marketing-style updates, that confidently funnel readers into a paid subscription tier (I got 15 paid subs from my last one, and so I realize the value in learning to play that game, but it’s just that, a game, yet a game that determines my financial security, but it’s not the full “culture” in “culture engine” that Substack can possibly build; it’s a reward function that could make this place like LinkedIn in <3 years).

So, how do you build a “culture engine,” for real? What is it beyond a tagline or positioning? To start, I think it goes beyond revenue. Of course, Substack needs to pay bills (separate point, but once we reach the vibe code singularity, the bills might be so low that SM networks won’t have to ruthlessly optimize). I think Substack could 1) diversify their business model, so that they don’t have a single attractor that incentives every thought to be monetized, and 2) make decisions from a cultural perspective—even if there’s no explicit revenue tie-in, by creating a good culture, you retain the people and prevent a Writer’s Exodus.

But to get even more specific, a “culture engine,” sounds like the kind of place that would trigger long letters back and forth between writers, kind of like this. I used to see some of that happening, but it seemed like a performance too: “And now, here is email 6 of 7 about how to start a public email debate” or something. The core difference is that, when there’s two people writing back and forth, there’s permission to perform less and less until you’re eventually just very real with each other. This is what I love about Neal Cassady’s letters to Jack Kerouac (troubled guys, who are a topic for another time). 

Why aren’t Substack comments like this? For one, they’re truncated. But two, I don’t know, sometimes comments even feel performative too? I feel it, on both the giving and receiving end. After I post, it feels like a chore to respond, even though I often love what people write and want to respond. I think it’s because, since it’s in public, and everyone can read, it feels like an obligation to respond. I wish there was an option to have “private comments,” and even “private replies to comments.” Like, other readers could see, “Michael Dean replied to this, privately” so they know I’m not a dick.

Okay, last thing, maybe: I think the real problem is that the discovery mechanics are all wrong. Like, I don’t want to blast this letter to everyone I know. But yet also, I don’t mind if everyone I know happens to stumble across it. There is a huge difference. I’ll put this in my logs, but realistically, no one is going to find it. I guess I could put it on Notes? But that feels too vulnerable too. Ideally, the right people will find it as they write about similar issues. So if some Substacker is also writing about private comments, to themselves, or to a friend, they will suddenly find a thread between Alex and Michael talking about a similar thing, and then suddenly we all have visibility into each other’s notes, letters, essays about those things. Forks merged.

The social media network I want to park in (or plug my personal website into) is one where everything is semi-public, but you only discover things through your own writing. I don’t know the right metaphor: it’s like each notes or essay is a flashlight that you use to move around this massive information cavern and you make friends along the way. It has nothing to do with engagement or revenue, but semantic similarity. This feels closer to the original vision of the Internet, to connect people based on ideas.

Sublime has some features that are adjacent to this, and Plexus was very close to this too, but I do think there’s something to owning your place. Is there some protocol where you can fuse the autonomy of your website with the connectivity of a network? I feel like AI is going to simultaneously bring us to (a) slop town, and (b) a golden age in social media experimentation; as sloptown gets neck high, people will want to move.

PS1: To clarify: I love having an audience, I just don’t love the way my writing is distributed to them, and also don’t love the way conversation is facilitated. Comments are okay, but the Chat feature feels pretty off. I wish I could write 30 essays per month, like this, and each one would get the 3 that are most relevant.

PS2: It took Alex 9 days to reply to my original notes, which is still ~2x faster than the letter cadence back in the day. That’s fast! I wonder if AIM culture poisoned letter culture. I haven’t responded to my Substack comments from 5 days ago, and I feel bad.

Just heard Hamish (on a livestream) say that Substack is a revolution, a “found economy,” that materialized 5 million paid subscriptions that wouldn’t have existed otherwise. What is a revolution though? I think I want to zoom into this positioning, because many words are being used interchangeably. Yes, it’s a new business model for monetization, but is that a “cultural revolution”?

It feels like there’s a bit of a fixation on the 10% mechanism, and the risk is that this reward function turns Substack into LinkedIn in the next 3 years. If the goal is to make a “culture engine,” you need to really ask what a culture is. If you’re culture is limited to paid subscriptions, it’s a small, unrepresentative, utilitarian culture, much more slanted to journalism and business tactics, regardless of an editorial attempt to bring a flair of literature.

We need to define culture (in terms of taste, values, and quality), and then make platform design decisions that have nothing to do with revenue. Of course, I’m not saying to abandon revenue focus; I’m saying that they need to allocate some percent of their attention to “doing weird things” to prevent a writer exodus as enshittifcation strengthens.

"The Death of the Corporate Job" went viral on Substack: 3.3k likes in a few days (eventually went up to 20k, I think). I am pretty sure this was AI-generated. I don’t feel like posting about it though. It’s clear to me that this is a kid in his 20s, building an AI tool for career discovery; he sees this essay as marketing. It will probably bring him a lot of customers. He might possibly help a lot people. I’m sure he believes in his mission.

What irks me is that the essay has been instrumentalized. There are fake I’s with vague personal details. Intellectually, it’s a ripoff of Bullshit Jobs. There’s no structural clarity, and it loops through the same points multiple times. No tension. Flat voice. Awkward repetition. I understand why the writer did this, but I’m more concerned about the state of readers, because this piece’s popularity is really a reflection of mass readers.

It shows that most people care about the topic, and barely notice or care about how it’s written. What thye care about is having their pain validated. To go viral, write about mainstream pain. So if this is what the masses want, shouldn’t we not care about composition and just write psychology-targeted think pieces? I mean, if you want to just build an audience at the expenses of your own satisfaction, then yes, possibility. But the quality of your thinking, and the friction to derive something original and independent, gives you something more than fleeting popularity, it actually shapes your lens for the longterm, and you earn something that is transferrable outside of narrow social status games.

#5 in science recently went viral for sharing that #2 in technology plagiarized her a year ago (right after #2 just went 10k-like viral, again). Substack is freaking. Plagiarism is obviously bad, and I think everyone is shocked to learn that #2 got away with blatant copy-paste work, but I want to focus on the nature of what was plagiarized along with why platforms reward cheap writing.

If someone else can put their name on your writing and almost get away with it, it means you haven’t written something only can you write. The plagiarized post was digital cultural journalism: mostly facts and studies, with only a few “I” mentions that are too vague to be anchored to any specific writer. Obviously it hurts to see your hard work get celebrated under someone else’s name—I’d be pissed too— but research is becoming hyper-commoditized. You have to assume it will be coincidentally/accidentally/purposefully refactored by hucksters, bots parrots, friends, and rivals. If #5 had integrated her research with singular, relevant moments of her life, it would be hard—if not impossible—to rip off. Personal experience is the last moat.

This situation feels like a predictable consequence of engagement-based competition. Among us are people willing to sacrifice craft for clout, at various tiers of insanity. I’ve been noticing high-volume accounts in the Top 10 with obviously AI-generated notes and essays. I wonder who actually reads/likes this stuff, until I look in the comments and realize it’s, likely, all bots. Is Substack status that easily hackable? I guess this is a growth hack that brings you an algorithmic edge in getting discovered by humans, so you can eventually replace the slop with your own writing?

As extrinsic games get increasingly weird, the status of winning them will get decreasingly valuable, I think. If #2 is a slopjockey, I don’t care to reach #1 because the whole game is now polluted (I’m actually a fan of leaderboards, but they need to be merit-based and unhackable). I just don’t know if platforms care to systematically fix this, because status-hackers create volume and speed that make a platform look vibrant to an undiscerning eye/investor.

Over enough time, I think misaligned platforms and those who hack them will eventually lose. The internally-driven writers have to put up with a lot of noise and chaos, but since they aren’t anchored in hacks, they’re less likely to have their means of validation suddenly disappear. It’s OK to be a tortoise in hell.

Substack's role is to grant its readers/writers optionality. This is what makes it different from a place like X that tries to own and dominate your attention. I want the ability to:

• Determine which Notes feed is the main one.
• Control the main icons in my app (and turn off Reels).
• Let readers opt-in for sections on subscription.

I wouldn’t even be that mad if they brought in advertising, assuming there is optionality (meaning, 1) it’s not in the Notes feed, 2) writers choose to get paid by putting ads in their own posts, 3) readers can pay a monthly fee to turn off all ads).

It is clear that Substack is making moves that lead to revenue (because they get a cut), and that’s fine, so long as they grant us optionality.

Email to Davey:

Thanks for sharing this, Davey. It's a nice encapsulation, an important idea, and I'm sure it's time will come.

I think your nuance on why Related Notes on Twitter didn't work is key. It can't be a side feature, it has to be core. Plexus solved the 90-9-1 problem (90% lurkers, 9% sharers, 1% posters). On Plexus, 100% were posters. This happened because the feed was intentionally withheld until you did the vulnerable thing of shaping/sharing your thoughts. And when you did, you were rewarded with a feed of similar thoughts (an act of encouragement / validation).

As Substack is undergoing TikTokification (my friend sent me a video of his Notes feed, which was all vertical video), I wonder, why can't the Plexus concept exist? Technically, it will be easier, each year, to build something like this, and I wonder what other social frictions need to be fixed for something like it to really work.

There's an inherent tension in a "semantic journaling" app. You want a space that both (1) becomes the place where each person captures their consciousness, but also (2) they want some control over who can/can't see it. I think there are a rare few who are okay being linguistically naked (ie: I have all my logs on my website and I don't care if anyone sees them). It definitely isn't the norm (most people don't even think at the edge, let alone write it, let alone share it). And I have my own limits too (for example, last night my wife reconnected with a middle school bully, and there's much I could write about it, but I lean towards not for the slim chance that someone in her group might find it).

There’s a chance that, at scale, semantically linking is just as unnatural as broadcasting (ie: people will get doxxed / revealed because everything is too interconnected). Maybe instead of having a semantic feed auto-generate, it will spawn a card (with an AI-generated title) that both parties have to accept for the logs to be exchanged/visible. The question is how can you capture the complex psychology of control/privacy in a simple interface/architecture that lets the average, guarded person be maximally unhinged, expressive, and idiosyncratic.

Maybe semi-public journaling will, over time, by 2045 (one of my predictions) become way more normalized, but maybe there’s also a tool that accelerates this (similar to how Uber, AirBnB are both tools that normalized culturally deviant things). Michael

Substack has the opportunity to do something fundamentally new with social media—which is to break out of engagement-based feeds. It’s like a megalopolis of good prose; and so a SM post could be a semantic search query that scans notes and essays (that have been sliced into paragraph arrays for more precise embeddings). A note, then, isn’t a scheme to go viral, but a way to actually surface inspiration and people from the network. What’s funny is that Substack search sucks and so does Notes.