michael-dean-k/

The neat thing about being a "writer-coder" is that you can shape your own writing environment as you write. This is being written inside of Margin Muse. Just after cobbling together that opening sentence, I've decided something: the text is too small! (PROMPT: "can we add another slider for text size?") An easy way to get over the blank-page effect is to see lines pile downward as fast as possible. This happens faster if the text is bigger. By the time I've gotten to the end of this dreadful, placeholderly paragraph, the feature is implemented.

Alright, that increased this from 5 lines to 7 lines, but I want the font to be untastefully big. (PROMPT: "why stop at size 22? what if we went up to 48?"). [REFRESH]. Now that's big! Size 36 feels like a nice starter font; it gives me the illusion that I'm writing into a vertical mobile screen. I am a sucker for typeface and design. It feels great writing in here, even if the content is drivel. Sometimes you just need to get started before you try to make it great.

There are hundreds or thousands of little decisions that go into a writing environment. Something like Google Docs was not designed for a creative process—it's an extension of being a secretary, the ultimate tool for collaborative, real-time meeting minutes. If you make 1,000 decisions geared towards the creative process, it might have a meaningful impact on it.

Is this not the best kind of software to build? It's not productivity tooling, not a scheme, not intended for anyone else. I'm building technology for the thing I love most: writing. By taking this seriously, it will—hopefully—be inspiring enough for others use as their default. Even if I'm the only user, all that matters is that my process compounds.

As I write all this, I'm mostly focused on making sentences, but there's a subtle awareness that the container I'm writing in is gooey and bendable. And so if an idea emerges, I shoot it into Cursor and continue prosing as the feature brews. Features pour in at the same rate it takes me to finish paragraphs.

Would other writers want to write within my own idiosyncratic editor? Of course not! But every time I add a feature, I need to remember that the thing I need is just one expression of feature set. Essay-to-essay, what I want might change. Within an essay, it might change too. Already, I find myself wanting smaller font, now that I'm six paragraphs in. And yet, I'm too lazy to change the font! I'm reclined in my chair, with my legs on my desk (terrible posture), and I don't want to reach for my mouse. It would break my flow of prose...

Imagine if there were key commands in here? All I'd have to do is press the slash key twice ("//") to open up a little pill that I can type commands into: "//font-size:16//". Maybe the entire interface, and all of the margin muses, are controllable through key commands! I like the idea of calling a prompt within here without breaking flow. I could write "//prompt: Where am I going with this?//" and then AI would think for a bit, process that as I continue to write, and then leave a comment within the document.

Imagine if I develop a whole new syntax for prose writing? I mean, in the end, none of it would likely be visible to the end reader. It's more like a process language for "draft zeroes"—a meta document where you write to conceive what it is you actually want to write. There could be unique punctuation and syntax to help call upon different AIs without breaking your stream of prose. In the end, I suppose this fuses prose & prompting together into a single field, and through the appropriate syntax, you can control how much of that questioning you expose to the reader.

I've arrived at what I want to say: is prompting not the ultimate skill of the essayist? If an article is centered around an event, and a profile around a person, is an essay not centered around a question? An inquiry? Are prompts not questions and inquiries? This taps into what I think AI is most useful for: asking questions. This sounds trite, because you cannot interact with an AI without asking questions. I'm sure everyone claims to be a great prompter. But the nature of writing, of design, of art, is basically about asking a chain of great questions. Of course, Montaigne did not have a mechanical muse answer questions for him; but a striking question prefigures the answer. It takes many drafts to get to the real question we want to answer, and once we know it, it's as if the essay writes itself.

The ultimate essay composition tool is one that turns you into a lightning rod for inquiry.

Moment of truth: do my slash commands work? ("//size:13/") They do! Unreal. Signing off with legs up and the full essay in sight.

[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? ¹ ("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 digests; 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.

[V] 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.

[VI] 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.

[VII] 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.

[VIII] Here's what I mean: AI is language turned into geometry. As transformers raven through NYPL-scale archives from data centers, they slice ideas into little packets and turn them into mathematical coordinates. Imagine every Kindle highlight translated into 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.

[IX] 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's root somewhere in geometric space, drawing similar experiences to that location. So during his thousands of LSD psychotherapy sessions (before that was illegal), he noticed the drug let patient more easily follow a chain of associations, from recent experience all the way down to the origin. 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.

[X] This is the limitation of Margin Muse. It might be able to transfigure ideas into 700-sided dice, but it's numb to how something feels to the author. AI might know that 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 factoidal hyperlibrary, I am starting to dedicate more time to the irrational.

[XI] 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?

[XII] 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 lose 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 see lucid images in my mind, and in rare cases 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 are moments of drivel, and some of primal excitement, but I tried something new last month. I didn't read anything at all. Not during, and not after. 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 lines, edit them into a whole, and call it "Heatflash" (it was written during a heat wave in early July).

[XIII] 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". Some details (I imagine you may zone and want to skip ahead, so I'll mark this stream in italics): 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.

[XIV] 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).

[XV] 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 muses, to 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 (edit: soon); 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.

"You may, like Nazianzen, all your days, make a little recreation of poetry in the midst of your more painful studies. Nevertheless, I cannot but advise you, withhold thy throat from thirst. Be not so set upon poetry, as to be always poring on the passionate and measured pages. Let not what should be sauce rather than food for you, engross all your application. Beware of a boundless and sickly appetite, for the reading of the poems, which now the rickety nation swarms withal: and let not the Circaean cup intoxicate you. But especially preserve the chastity of your soul from the dangers you may incur, by a conversation with Muses that are no better than harlots: among which are others besides Ovid’s epistles, which for their tendency to excite and foment impure flames, and cast coals into your bosom, deserve rather to be thrown into the fire, than to be laid before the eye which a covenant should be made withal. Indeed, not merely for the impurities which they convey, but also on some other accounts, the powers of darkness have a library among us, whereof the poets have been the most numerous as well as the most venomous authors. Most of the modern plays, as well as the romances and novels and fictions, which are a sort of poems, do belong to the catalogue of this cursed library."

—Cotton Mather, "Of Poetry, and of Style" (1726)

We grossly over-estimate how easily we can stretch our will across time. Even the simplest action, a nightly journal—this—, which feels so achievable in the rush of inspiration, now feels impenetrable at a night’s end, while guiding at baby’s bottle at the end of my chin, typing into my phone to keep a streak, hoping to cobble some unexpected essay in the moment. I have no topic in sight; whatever lies ahead will emerge only through association.

I have a bulging vault of wisdom, but it’s all forgotten and I have little time to comb through my archives, so it lingers at the edge of my consciousness, always taunting. That is over dramatic. What I mean is I feel like I’ve grasped important truths, but let them slip away. It is not enough to hold the truth once. The moment you take your eye off it, which happens almost immediately, it’s like you never had it; even a seemingly shattering insight will slither away each day until it has to be relearned again, though I imagine each time it’s slightly easier to learn—and each time you remember how easy forgetting is, how hard it is to metabolize anything.

I suppose this is one form of overthinking. I suppose I could trust the process; the fallibility of memory is a feature—if I can’t remember something, if it doesn’t imprint on my character with ease, then it’s probably not important enough to remember. This is the default, and perhaps the personal default is the global default, applied across populations, and so in the end one’s inner nature is so consequential that it’s of no use worrying or fighting it; all cards fall into place.

The opposite approach is to build a hypnomnemata; an organized palace of insight, returned to at semi-frequent intervals, to reinforce found lessons. It’s not enough to build a writing archive of a million words; there is follow-up work in turning sap to syrup, in compressing essays into aphorisms, in categorizing them, and in returning to the right silo of thought when some new trouble looms, monthly, in endless undulations.

Returning to an idea is really a form of prayer. Prayer need not be religious or denominational; prayer internalizes meaning of any kind. I learned an idea for Iris Murdoch that sticks with me: she says that, in any moment, your decisions and actions may be predetermined, however it’s not determined by fate, but by the nature of your attention in the minutes, hours, days, and years preceding that moment—in your down time, you have autonomy in how you pay attention. She’s trying to make the case that attention itself is consequential; it shapes your character and your character shapes your decision making.

This model definitely applies to writing too. My output on any given day is contingent on what I’ve absorbed in the days and weeks before. This is often accidental, but it need not be. To improve at writing, it’s rarely about learning some rule, acquiring a meme, or purchasing a trick, but in shaping your mind through deliberate attention so that some quality emerges from the subconscious in the future.

I suppose this is all surfacing because we just read Virginia Woolf in Essay Club and I’m in awe of her technical brilliance, again. I’ve reverse engineered her, years back, and can’t quite trace how much of that, if any, sunk in—either it was foundational or it never cohered. In any case, at one point years ago it felt like I really understood her, and yet now I am again seemingly baffled. Did I forget? Do I need to reserve some hours to dissect? It feels like some percent of what I do, consciously or unconsciously, gets absorbed—but most is lost…

Or, figuring out how to retain your inspiration is perhaps the actual meta-skill to solve.

I wonder how much of my own Essay Architecture system is currently loaded in me as I write this. I am really just following the idea here, and whatever emerges, formally or stylistically, is merely accidental. I don’t doubt that my own ideas could be better loaded. There’s probably some “boot up” process, daily, weekly, and monthly, so that the right ideas continue permeating and anchoring in the subconscious. But would this be a chore?

What’s probably irking me is that I feel slightly detached from the vision of the essayist I want to become. It is natural to anchor this in heroes, the writers I admire; yet I see flaws in them; crucial differences—I know I am not them, yet in some fundamental way I don’t quite know what I am myself, either. It feels like I used to have a legible and explicit true north, but as you get better, you also realize how shallow and simplistic your old goals were. So there’s a chance I forgot and lost touch with them, but also an equal chance I just outgrew them, and now struggle to articulate what I want my writing to be.

What I strive for is a synthesis that can’t be easily prescribed into a method. I suppose this whole note is “essayistic,” in the sense that I’m barreling forward trying to answer a question—how does a self propagate and evolve through time?—yet it’s lacking in idea, form, and voice. By rational analysis, it’s missing almost every ingredient: no experience or microcosm, no references or response, a meandering structure unoptimized for reader attention, and a perhaps overly pragmatic voice with little poetry, despite some occasional metaphors and flare. I suppose I could fix this all in rounds of rewrites, but that is not in the cards for this idea; this will only ever be a captured thought stream; a true account of what’s going through my mind as I sprawl on the couch. Yet, if I my insights were “loaded,” would my first drafts be more poetic, more well-rounded?

To lob insights into the future, perhaps they need to be materialized into a totem. I look around my apartment and see nothing but my past carried forward: paintings from dead grandparents, paintings of the dead family dog who I watched get euthanized, architectural models from a summer abroad in Italy, a 1950s radio, our wedding flowers, an inherited library. Unlike my thoughts, it’s as if I couldn’t escape my past of I wanted to. While thoughts evaporate, possessions accumulate.

How can we cast our abstract epiphanies into stone? Is this reification? The totemification of everything? Where are the boundaries? What is the visual language to work within? And what is the ritual? I sense that post-it reminders fall short of emotional charge. On the contrary, I have a statue on my desk of a man with a book for a head, holding his skull in his hand, looking back at its book-head. This is symbolic and charged, yet I almost never see it. For months I walk by it with it having no effect. Even when I do see it, I see it too quickly to absorb it and for it to imprint on my consciousness. This means it’s not enough to load your inner quarters with odd assemblies, each with a story; there is an art of looking upon your collected interiors, in seeking the fixtures that blend in as something new, in remembering their message and recasting them into you.

To learn, then, is not just to behold knowledge once, but to totemize and worship it. The question is, to what degree can you achieve this? When do you know a factoid is worth totemizing? How many totems should one have, 3 or 300? How intricate of a ritual can I bear? I suppose there are mega-totems and mini-totems. A mega-totem is a larger frame that answers some foundational question, like what kind of essayist do I want to become? If the answer to that is Montaigne—it’s not, at least not quite, not in totality—then perhaps I need a framed picture of him I reflect on each morning. A mini-totem is far more granular; I notice how Woolf compressed her sentence lengths and uses rhyme in a moment of action; that’s 1 of 1,000 things to remember, and so that makes more sense in a digital hypnomnemata. For that to work, each idea needs to be like a Matryoshsa doll, where I can scan all ideas quickly before going deep on any.

It’s tempting to start making a hypnomnemata, but really I should start with the large totems, and really test how those can reverberate through my daily writing sessions.

After being a father for six months, here’s a predictable observation: days feel similar. I bring my daughter out, of course, to parks and pools, so we’re not entirely homebound. But I can’t, for example, spontaneously take a train to Manhattan the night of July 3rd to see the ball drop before the semiquincentennial—it’s not that I particularly want to do that, it’s just that every impulse to “get out” is filtered through, an is-it-worth-doing-this-with-a-stroller-and-supplies filter, or an is-this-even-possible filter, or a would-this-be-inconvenient-to-my-wife filter. There is a common groove: work bright and early, baby stuff all day, and then resetting, relaxing, and recalibrating at night.

So, at least for now, there is notable change in “experience.” Not a change in quality, but in type; it’s a lapse in variety of experience, which personally doesn’t bother me. Your mental fortitude for early parenting probably bears some resemblance to how you fared during the pandemic. There is no virus, but a similar warping in the nature of days.

But, the pearl and point of having kids is the experience of raising a child; it lacks the variety that a single nomad in Bali might have, but it is a singular channel of experience with extreme depth, meaning, and change. Once you figure out how to make your kid laugh, and how to intuitively communicate without language, and where they are ticklish, and how to guide their attention to get them to focus on books—you discover the tremendous variety within the thing that matters most.

As a writer though, it seems like I prevent myself from writing about parenting. I tend to mention it loosely, without my daughter’s name and without much detail. I always find myself not thinking linguistically in moments with my kid. Maybe I should? I just usually forget. There feels like so much nuance packed in a single event and glance, that to stop and write it both severs me from the potency of it, and sever me from them.

So, while I find myself in recent months with few “stories” I’d happily share an essay around, I do find myself reading more than I ever have in my life. Considering she sleeps a lot, on me, it’s just a space I have. I imagine when she starts walking, or gets older, this might evaporate, but for now I’m reading 1,000+ pages per month. I feel less anxious about the lapse of new experiences, knowing that in a few years it all comes back, and I’ll come back with a new head, a new constellation of nodes to bring to the variety of experiences, along with a little person who will force me to see everything anew.

Hey [ * ],

Don’t apologize for rambling; a good part of essay writing is just following a train of thought to see where it leads (and editing after). I enjoy your letters. You can articulate things well, and shouldn’t feel insecure about your words, or feel like you need to use AI.

I think your problem might be the need for certainty before you start. It sounds like you want to know your topic in advance (*), frameworks on how to make an essay, and the standards on what makes it great. These are all important, but I think you’re clinging to them pre-maturely; I don’t think you need to worry about topic, process, or quality until you’ve published 50-100 things. To start, it’s more about establishing the routine of becoming a writer, and once that is flowing, and once it’s almost guaranteed that you will publish something at your ideal interval, then you can start tinkering with other variables, testing if you can incorporate some new goal without interrupting the momentum.

I went through a very similar thing. I took a writing course, Write of Passage, published 2-3 essays, but then stalled. After it was over, I showed up for 100 days straight to my small writing group, and even though I thought, wrote, and edited every day for 1-2 hours, I didn’t publish anything. The core realization is that the process was getting in the way, and I was held back by my own standards prematurely. It’s all about publishing. Thinking and editing don’t count unless you bring a thought to a point where you’re willing to share it. Starting January 2021, I published 1 idea every single day for 45 days, and from there I’ve been publishing semi-regularly for 5.5 years (and through that time, the process continually evolves, and the quality bar varies but generally averages upwards). I’m almost at a million words now. All my thoughts from 2020 and before are mysterious and fuzzy, because I never froze them, and so I can’t know exactly what I thought back then. My most important thoughts since are all legible, and even if they’re poorly written and wrong, I’m happy I have them, for they’re a record of my own evolution.

My advice to you is to start a simple website where you can publish your thoughts every day. Daily publishing is a strong way to break out of a rut. It’s surprisingly doable, and forces you to get out of your head. You should have no expectation for it to be good, no sense of process (imagine writing a stream of consciousness letter like you did to me, but every day, on different topics), and no commitment to a topic (no more than 25-50% on X or Y). These don’t have to be good. Most of them won’t be. But by having them in public, you’ll care about them more, you’ll re-read them, maybe retroactively edit them; but of your first 30, you might have 3 that you’re really proud of, which is 3x more than if you tried to make 1 perfect piece per month.

I don’t think Substack is a conducive place to start this project, personally. If you publish 30 times and get 0-2 likes on each, it will feel like a failed project; if you do that same thing on your own website, it will feel like a massive success. If you don’t have an idea of where you would host your writing, let me know and I can offer suggestions. I’ve created my own site recently with Obsidian/Claude/Github/Netlify, but to start it’s not worth getting hung up on infrastructure. Spend no more than 15 minutes on your setup. There are plenty of minimal blogging platforms that will let you get started.

Let me know if you’re up to experiment with hyper-publishing. It’s about publishing every day, regardless of length (could be 40 words or 400 words).

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.

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

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

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

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

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

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

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

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

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

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

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

Something about hyper-logging (capturing your mind in prose) feels desacralized when I see it as the grown-up development/extension of my AIM bio, or my original Facebook bio (which had a whole series of categories, like favorite movies, books, etc.). Why keep an extremely detailed and public log of my self and thoughts? I guess I see it like a change log of my evolving identity. That was sort of Montaigne's whole thing (perpetually in transit). I imagine the norm is to burrow into your shell of self for as long as possible, to avoid the confusion of drift, but I try to harbor a non-static self. I feel a cringe in sharing this self-congratulations. There's the tension.

I think I'm doing an irregular thing by obsessively documenting thoughts, and from my own perspective it does feel like I'm continuously evolving, but an outer perspective might see this as nothing more than a frivolous blog. It's likely that my whole arc is illegible. Some degree of it comes to surface, like my ever-shifting "career," but most of how any of us feel, think, and change is illegible to each other, except in extreme rare cases of friendship, and so the more idiosyncratic your path, the less anyone can understand you.

I suppose my logs could function as a private journal, but it would lose an important quality. While, there are some consequences of writing in public (a subtle self-censorship), there's something more important you gain: the stakes of knowing that your work could be read in the future, if not by a friend or stranger, then at least a future version of yourself. Whoever it is, if they care to spend the time to read, they would understand you more than probably anyone in your life. That slight pressure snaps me into a mode where I try to be coherent, articulate, and sometimes expressive. When I look back at my old chicken scratch journals, I almost always skim and skip and hate it. But when there's a slight care in crafting the language of my thoughts, it becomes something that outlives the moment.

And so if public writing comes with self-censorship, and private writing comes with a lack of stakes, then the way to go is semi-public publishing. It gives you both freedom and stakes. You won't grow your audience this way, but I think you will forge a sense of self and voice that you can bring with you when you try to build an audience, but that's really secondary. It's the self and voice that matters.

I have some neat prototypes for a personal website, but now I actually want to build a stable backend, one that can serve me for 5-10 years, or more (100-year hosting would be ideal), and persist among many different UI or platform changes. This means I’m trying to think forward to where the Internet could be by then. This involves extrapolating a current trend to its extremes, and even if you don’t know for sure it will happen, it’s good to have comfort in knowing you’re protected from extreme edge cases.

The one top of mind is the death of the open Internet. This goes way further than “the dead Internet theory” which only covers the proliferation of bots and slop. This is about bad actors being so leveraged that it becomes dangerous to have any public content of yourself, in text, image, video, or audio. ie: Any hacker or frenemy can clone you and do what they will. Or maybe a rogue government can analyze your psyche and determine your "loyalty score" is only 35% and shadow ban you from getting a mortgage. I will not get into specifics here of the likelihood of different cloning, phishing, or surveillance schemes, because all that does little but bring you to madness, but my point is that if you want your website to be a 5 million word 1:1 representation of your mind (in all it's vulnerability), it's worth designing for the most paranoid future possible (like how engineers design bridges for earthquakes that will likely never happen).

One response to all this is cyber-defense. At the absolute minimum, this means locking most things behind a gate where only the approved can get through. A more clever, technical solution is to share encrypted “coordinates” that represent the semantic nature of an essay, and then let people surf through prompting and approval gates. An even more extreme idea is a mostly-private site with a kill switch, which involves (a) signing in once per month to mark "I'm alive," and also (b) giving my wife a secret key to type in when I die, which then releases all private material. Obviously this throttles reach, but isn’t there psychological value to limiting your audience anyway? Montaigne wrote alone in a tower for a decade, and so if the approach is to use writing to steer you life and mind, at the detriment of audience growth, then this might be the way to go: a literary labyrinth accessible to maybe your 30 closest friends and anyone else via application who can prove they are not a ghoul.

The other alternative is to embrace the weirdness, that no matter what, we will all be rendered through a schizophrenia filter, with no choice but to relinquish control over the non-canonical or rogue versions of ourselves.

For the last two years my lock screen clock has been set to Khmer, the language of Cambodia, with numerals I (still) can’t parse. The point is to not poison the flow of my day with chronos.

I started this experiment because I realized how obsessively I would check the time, as soon as I woke up, through morning and evenings and weekends for no real reason, in situations among friends where the hour was irrelevant. Time was a commodity, something to budget, forecast, control. Only when I got off the clocks did I notice a whole layer of quiet, instant calculations I’d perform to steer the immediate future (ie: it’s 9:43pm, which means I have 17 minutes until 10pm, which means I can only do 15-minute things until the 10pm-things start to happen). Chronological time alienates you from kairos, the ripeness of any given moment.

If we pick up our phone 96 times per day (the average), then we’re aware of the time every 10 minutes. We’re a society stuck in time. Lewis Mumford said that the clock (not the steam engine) is the central machine of the Industrial age, the thing that dissociates us from our natural rhythms.

Of course if I have back-to-back meetings or multiple trains to catch, then I need to be in manager mode and know time to the minute; but in all other moments, I strive to be temporally oblivious. I don’t know the time right now. I assume it’s somewhere 8-9am, and when Christine rings the doorbell I’ll assume it’s almost noon, and I’ll look outside to see the sun and shadows to confirm it’s no longer morning. When I’m hungry I’ll go eat, but unfortunately that brings me near the stove clock which breaks the spell (I’ve tried scrambling the stove clock, and that obviously annoys my wife). Whenever possible I default to removing clocks from UIs, or turning them to analog to create a second of friction, or, when iOS forces me to see ##:##, I revert to foreign numerals I can’t comprehend. Not every room in your home needs a clock. You should never know the time in the room you write.

Good voice is writing that's unchained from a single register. This is why default AI sounds so robotic: even if you prompt it with the precise style you want, it applies the same approach to every single sentence to make a monotonous caricature. No matter what it is, it’s numbingly uniform.

I find that if a writer gets caught in any register (only hilarious, only referencing Aristotle, only confessing terrible things, every sentence is a metaphor), it becomes annoying and unbelievable. We probably all have our default register. I get annoyed when I catch myself stuck in an analytical register. People don’t act like this IRL. People are 75-sided and context dependent.

As a writer skirts over different objects of focus, the tone should alternate between opposite modes: certainty and doubt, anger and love, approachability and authority, active voice and passive voice. There’s obviously no single tone that’s better than any other, but adaptive tone is better (=more organic) than drone tone. 

Organic voice is, I think, one of the halmarks of the essay. While other genres are locked into specific registers (research papers are certain, neutral, and authoritative, with terrible passive constructions to capture every nuance), essays are exciting because they capture the multitudes of expression.

I've always thought 'writing shows you what you think and editing helps you change your mind'—and maybe that’s a decent heuristic—but it’s more complicated than that. I think it’s possible for writing to do the opposite of what we hope, to lead to self-deception. A few thoughts on how:

1. Premature convergence: When you start drafting, you unlock a new stream of thoughts, but once you find a new center of gravity (a potential thesis), it’s common for all further thoughts to reinforce the thing you happened to stumble on, regardless of its substance. Beyond a point, writing can ossify & lock you into a frame.

2. Aesthetic attachment: Once you’re trying to make a ‘good’ essay around your thesis, it’s easy to become enamored by phrases, sentences, images, and sources. Expression (vibes/voice) is an entirely different thing than thinking. You can dress up a static/wrong thought to be beautiful/persuasive.

3. The sunk cost fallacy: after you spend hours on an essay and share it, it’s likely that you’ll continue to believe it. If you’re wrong, you’ll have ‘wasted’ that time. If you change your mind, your readers will have an outdated model of you (OFC, views evolve over time, but I wonder if publishing leads to short-term friction in your evolution).

One possible way around this is to, as soon as you think you found your thesis, to rigorously consider and explore the antithesis (not as a rhetorical strawman, but to really, earnestly, consider the opposite). It means a given draft will be scatter-brained and contradictory, but it’s how you find a synthesis, a more refined thesis. And once you find that, you start over, and repeat, until you end up somewhere that is far more nuanced, interesting, and weird than where you started.

The thing I’m grasping at is that thinking & expression are often at odds, and before you commit to an idea worth expressing, you need to go through rounds of unglamorous self-interrogation. There is probably a mode where thinking _is_expression, but the risk is not wanting to shed something that is elegantly said. One way through this it to get meta and explicitly express your doubt and your evolving POV; I think this is what separates essays from articles and propaganda, and it stops you from brainwashing yourself.

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.

I want to adopt a three-lane model of writing (and especially as I enter fatherhood, I’m going to have to). An essay can take 2 minutes, 2 hours, or 20 hours. 

• A 2-minute essay is a log; I can do many of those per day. More so than time, those require presence and discipline: the ability to stop in any moment, realize something is happening, and just write it down. If there is enough time for a 2-minute scroll, why not a 2-minute paragraph? 

• Next is the 2-hour essay, something you can start and finish in a single essay. The goal here is to pick “layups,” and I don’t actually mean “pick the easiest idea,” but more like, “pick the one that is fresh and active in your mind, and ready to come out now.” If you haven’t been daydreaming about it throughout the day, it’s probably not the essay you should try and write in a single sitdown. The goal is to publish before leaving the chair. 

• The final essay, the 20-hour essay, should be undertaken much more infrequently. A realistic goal would be to do 4-6 of these next year. Behind the 20 hours of “writing” is maybe another 200 hours of subconscious marinating; the goal here is to start from important, timeless questions in your life—maybe, your “12 favorite problems.”

Being a writer involves stubbornly carving out time from life so that you have the space to reflect on it. You probably miss something if you permanently retreat into your own cave of rumination, but also you miss something if you are just completely immersed in your own stream of experience with no distance to step back and process it. I think logging is that middle ground; when you take field notes from the front lines of life, you have high-res shadows or your experience that you can bring back with you into your Writer’s Cave.

I get the sense that creativity used to be seen as a form of artistic mastery, but in the 1990s, creativity turned into catharsis, therapy, self-help. It’s an “if I don’t do it, I’ll get sick,” attitude. I resonate with that—I often refer to writing as a release valve; without it, my head would get clogged and blow up—but not at the expense of technique!

Mastery is about breaking what you made, trying again, breaking it again, pushing the boundaries, and demanding an answer to “how do I make things?” Once you've made a bunch of things, you start to intuit your limitations, and the question is do you accept or interrogate why.

The process of interrogating is not only hard/heroic, but it’s rewarding in a gentle way. 1) The things you work hard on will be special to you for your whole life. 2) You slowly enhance and develop skills in and out your domain. 3) You build community through working together on hard things. 4) It reframes other elements of your life: pain is a puzzle.

I wonder if there is a Trojan Horse version of sneaking mastery into society through a self-help framework.

What would it look like to write a memoir in real-time? It would require a kind of real-time record keeping and interpretation of my activities, sensory impressions, and emotion. Even the boring moments would come through, stretches of focus on ordinary days before anticipated events. It’s tempting to say I’ll write a personal essay when I go to SF next week, but I should assume there will be no time in coming months to focus deeply on a piece of longform literary writing. The memoir is live. Prose has to happen in the moment, instantly crystallizing. My notes have not been personal. I suppose I fear someone will read them and find themselves in them. Are these risks real? Why not have logs just be the hyperlucid accounts of all conversations, regardless of who is implicated? Even if they cared, over what time frame would they care, and if they do, over what time frame will I care that they cared? All these thoughts are either 1) flimsier than paper, or 2) eternally lodged in the deep memories of an ASI, so not sure if I should loosen up or burrow.

I want to write an essay about how—starting In the 1990s—creativity advice was re-targeted for the mass public, and in the process, it got watered down.

There are three general modes that have become mantras for beginners:

1. ”Art is therapy.” This is found in Julia Cameron’s morning pages and in Stephen Pressfield’s The Resistance. It frames art as self-help, as a kind of therapy. You can’t create because you’re blocked, and once you create, you unblock. This frames the idea that art isn’t about mastery and the struggle and will to attain it, but in feeling good about yourself.

2. “Taste is all you need.” Rick Rubin is associated with this new philosophy that technique doesn’t matter; you just need strong opinions. This is a worldview that is easy to adopt, because everyone likes to believe they have good taste without having to work for it. Now with AI, doing the work won’t matter as much as having the vision for what needs to be done. There’s a weird and unfortunate ethos that craftsmanship is redundant, and all you need to know is good from bad.

3. “Just show up and it gets easier.” I think of Austin Kleon’s Show Your Work—a book that first introduced me to the idea of self-publishing online—which encourages you to just share your process. Keep showing up. It’s a philosophy that’s unique to the digital age where anyone can publish, and is probably the origin of David Perell’s Write of Passage too. It is the operating mode of newsletter writers. It helps get started. Paired with this idea is The Taste Gap by Ira Glass, that says the more you work, the closer you get to your heroes (I believe the opposite: the better you get, the better you realize your heroes actually are).

There is truth in all of these, but they are half-truths where their opposites are just as important. If you ignore the forgotten halves (analytical study, craftsmanship, embracing challenge), it might actually hold you back and frustrate you.

I am undecided to the degree that I want to write about cockroaches.

First, obviously, they are skeevy. Roach prose is definitely less gross than a Google images search, but still, it’s far from a feel-good topic. I don’t want to put my readers through thinking about them too much, let alone myself. But I feel intrigued to write about them; there’s the Burroughs-like writerly obsession with roaches in Naked Lunch—which feels like an honestly twisted curiosity that is nothing to aspire to—but it would feel insincere to mimic him. Still, experiences with roaches are uncomfortable and memory piercing and physiology altering and I guess I want to freeze them in text.

I am the exterminator because my landlords are very nonchalant and I wouldn’t be surprised if they just crushed them with their hands (I have seen them do this once, at our lease signing). I have a new habit of applying Indoxicarb near the radiator with a syringe; the theory is that, since they are scavengers, they will grab the bait, bring it back to the nest, and poison their families. I’m skeptical of this. In any case, this my 2nd time finding “roach droppings” under the radiator. Does it immediately expunge everything in their intestines? This time though, I looked at the underside of my Clorox wipe and saw what seemed like a microscopic baby roach, dead or alive I’m not sure, and I couldn’t tell if it’s legs were wiggling so I pinched hard just in case, but now I am in this ethical haze of seeing my self as a roach abortionist.

There is an intimidation in knowing you’ll never read all that you want to read and never write all that you want to write. There are nearby dimensions you could know but won’t. "βίος βραχύς, ἡ δὲ τέχνη μακρή," or "Ars longa," vita brevis," or "Life is short, the art is long." That aphorism was originally by Hippocrates about the practice of medicine, but Chaucer extended it in 1380: "The lyf so short, the craft so long to lerne." Those phrases acknowledge the fact, but not the dread or urgency behind it.

06:45 PM – By looking through this thread, you understand where ChatGPT psychosis can come from. It shows the range of ways AI can make people cry, mostly, from being validated. This isn’t inherently bad, but someone who is validation-starved is more likely to put an insane amount of trust in the praise-giver, enough that they’re willing to re-orient their whole world view around it. It’a also able to bring ideas into language in a way that a non-writer can't do on their own.

Can I make the case for writing as fundamental to the liberation of consciousness? It’s not about becoming known in the literary world, or to advance your career. It is more fundamental than that. Writing is a way to edit the source code of your mind, to rewire your perceptions.

It’s even a tool to change the world around you. Religions, governments, and company define society through prose, code, and law. There’s always been an asymmetry; the writing was done by a small cabal. What happens when anyone can make software? What about a religion that encourages writing for self-knowledge? What about a liquid democracy that let’s citizens shape policy through essays?

People who think pseudonyms are cowardly probably have no idea how much they subconsciously self-censor. They’re unaware how agent-arena relationship shapes and limits anything they say. To see what true freedom is like, you need to mask the agent in a familiar arena, or, move the agent to a foreign arena. Even someone with a pseudonym settles into a new agent-arena relationship, and needs to experiment with new pseudonyms and/or create new arenas with different constraints.

Comment on Silvio's essay:

This was great but the 4/2 entry could use a bit of editing. Kidding. Love this, and also, as you would expect, I disagree. I hope to respond to this sooner or later in detail (and it might even be fun to do some public letters back and forth).

This reminds me of Kerouac’s story; he was disgusted by the idea of editing, and remained unknown for years. On the Road was illegible, until Malcolm Crowley edited it 5 years later. By making it legible, he achieved international fame, and it ended up destroying him. There is a cost and risk of legibility, but that’s a different story I think.

“Editing is violence” is a powerful phrase, and speaks to the strength/disorientation of having your ideas/mind/self rewired. It’s something like an ego death. I personally think it’s valuable which is why I invite people to be as violent as they want with feedback (meaning, Im willing to start again from scratch if you can convince me, but I won’t just agree with anything you say so you’ll like it — I think there’s a stance to be open but extremely skeptical with all external feedback).

I think there a near-spiritual meta-ability in the learning how to detach from mental forms and be open to experience something with truly fresh eyes. Sometime this comes from within, but often it comes from time, weed, or, an editor.

I do agree with you that there’s a petty type of editing where you’re trying to appease a narrow/fleeting market need, but ultimately I think it’s up to the writer to hold their own internal vision for an idea when it makes exposure to a crowd. Maybe it’s not about total isolation/artistry and not about total market conformity/desperation, but as Emerson says, the sweetness of solitude among the madness of crowd.

I just wonder if it’s possible to honor both states: most expression deserves to be untouched, but some ideas are worth treating as a puzzle that you invite your friends to help you solve.

My logs need to become much more unhinged. I should hold back nothing and write from the perspective of death, as if every moment is fragile and fleeting and if you don’t speak honestly, in full force, with damning truth and judgement and acceptance, revealing all, then I'm betraying my own soul. The dead don’t check their metrics. The dead don’t hold grudges. If your main imperative is anything other than rendering your own consciousness, then you don’t see through the illusion of time. If you write for what you think the Substack Notes crowd wants to hear, then you are polluting your post-death corpus with drivelous digital small talk.

In my first 100 days post-WOP, I wrote every day and basically published nothing.

What helped me snap out of that rut was to take on a mindset of "single session publishing." This means I sit down for a writing session and don't stop until it goes on my site (sessions were 2-4 hours). They were effectively first drafts, and sometimes I'd come back to revise them. I didn't "blast" them to my email list, but DM'd them to specific people to start a conversation. There was something about having a body of work on my website that took the pressure off (eventually) sending essays to my larger list.

I'm 100% a perfectionist, and think it's worth having a rigorous, increasing quality standard, but it's important to also have places with much lower standards to serve as your release valve.

Also, publishing under my legal/professional identity came with all sorts of psychological blocks that were completely invisible to me until I started publishing under a pseudonym. Every situation is different, but I wonder if shifting to semi-pseudonymous Substack would help take the pressure off everyeone.

I’m sort of inspired now to create a section on my own Substack called “Drafts.” You can customize that so new subscribers by default aren’t on that list. I currently have an “Experiments” section on my site, but “Drafts” feels a lot more self-explanatory. (Some of these drafts will eventually reach “peak” form and get reposted in the Essay section, but that won’t happen with most of them).

In the spirit of experimenting, I live-streamed myself drafting on Substack Live yesterday. 50 minutes, 2,700 words, 38 viewers. It was interesting to see how that context shaped the writing process. Since I knew people were reading live, it was like I tapped into this unbreakable flow state in order to weave thought together at a rate of 54 wpm. I thought the whole thing was 10-15 minutes and almost missed my train. It’s similar to typewriter brain, but perhaps the opposite in terms of speed. Maybe it’s a mode that’s actually helpful at certain stages of drafting. TBD.

When you practice the patterns of essay writing, you don’t just become a better writer, but a better thinker. Rhythm enables you to compress ideas on command. Repetition helps you poetically elaborate. Rhyme helps you search a synonym space based on sound. Imagery enhances your associational and descriptive abilities.

What if the root of an OS was a place to just stream prose without too much concern over where it goes? If you only let yourself write in the context of logs, essay draft, memos, or typewriter one pagers, it’s constraining. I’m experimenting with a daily gDocs page that I use just to think out loud. It should be mostly a stream of consciousness—a way just to shift through ideas in my head. I realized that all morning I was stuck inside of a thought loop. Even though I got some stuff done, I didn’t have my head tuned right. It seems like a simple walk & location change fixed that, and now I’m moving forward

I discovered today that I could write a journal entry that is intentionally illegible to my future self. I’m writing letters, but blending them so loosely that it would be undecipherable to anybody. This means I can write fast and say whatever I want, and nobody will be able to return to this, which opens up a certain kind of confessional/abstract valve. It’s a way to use “writing as thinking” but encrypted in a way so the shadow can come out.

If you’re concerned that an AI will soon write better than you, it’s worth asking, why are you writing? (I mean this sincerely, not as a dig). There are so many intrinsic joys and values in slowly and meticulously crafting sentences. It doesn’t matter who’s watching, what it’s for, what technology is available, what generation I live in, or if anyone else likes it.

Through writing and editing, slowly and manually and sometimes painfully, you discover what you think, who you are, and how you express yourself. If you’re not in the pocket with language, there’s no transformation, no evolution, no humanity. It doesn’t matter how many billion parameters Claude Sonnet 3.5 has, or the prompt library you bought for $49, or whether you’re on Pro tier—it matters if you’re willing to sit alone with your own thoughts for more than 5 minutes, and for hundreds of hours more. It matters if you’re willing to shed your identity over and over.

I get the source of panic: soon enough (2025? 26?) AI and its midwives could trample out 100% of humans at the “art as commodity” game—maybe that’s a good thing. It wasn’t a great game to begin with. It distorted all the incentives of human expression. It created monsters and beggars. ASI means that the transactional, mercenary, instrumental skill of “content writing,” will no longer have value. This will create a strange, noisy Internet, and I sort of hope it drowns in pseudo-drivel so that in its ashes we can form a new one that’s less like American Idol (commerce was illegal on the Internet until 1991).

Now for the contradiction: I make money from writing online. I have a Fellowship Grant which gives me at least year of security. I have, relatively, a good number of paid subscriptions, which is currently around 1/4 of a full-time income. I live in New York (not by choice, by birth). As much as I hope and believe that I can sustain a full-time income via writing (the thing I love), I also (1) accept that ASI could wipe out the whole cultural appetite for writing and send me back to a FT role at an architecture firm, and (2) even if “Essay Architecture” is a success, I need to protect my non-legible non-optimized, non-practical writing impulses. (Ie: I hope that on “launch day” of my app, I spend 2-3 hours on a typewriter essay about thumbs, or something equally trivial, unrelated, unproductive).

So while you can make money and build influence via writing, you definitely don’t have to. Maybe it’s about to lose some of its economic function, but we shouldn’t underestimate its cultural/democratic function. If you look back through history, most of the famous essayists had other jobs—they were lawyers, doctors, publishers, physicists, architects (Frank Lloyd Wright). Essays just flowed out of them. They couldn’t help it. I really think essays are the most democratic medium of the arts. Unlike architects, you don’t need millions of dollars to start. Unlike novelists, you don’t need years of focused attention. Unlike musicians, you don’t need to learn abstract chord languages and train your finger muscles. An essay is democratic because anyone, in their own language, in a day, at almost no cost, can engage with composition and meaning-making, and share it with their culture, even if it’s a single friend. It might be our most important form of leisure.

So maybe this approaching techno-apocalypse is an opportunity. It can scare us inward. It can shatter the dream that we can be a Mr. Beast, a niche hero, a perfectly legible and distinct human wrapped in plastic. The irony is that by going inward, you might just find the thing that has outward appeal. The best kinds of extrinsic opportunities aren’t the ones you engineer, they’re the ones that knock because you tinkered with your garage door open and accidentally found a new source of gravity.

To finish with AI: I’m all for it, so long as it is my assistant and not my sentence jockey. I will never replace my document editor with a chat pane, but I will invite agents to live in my margins. I’ll let them watch my words as they form, and then offer up research, feedback, and disagreements, all of which I’ll have to manually integrate. Slowness is the theme. You don’t change without immersing yourself in an essay. AI might give you insights, but you know they’re illusions if you’re not wet—if you’re not even in the pool. You can automate the outputs, but you can’t automate the watering of mind and blooming of character.

John Irving:

“If you don’t feel that you are possibly on the edge of humiliating yourself, of losing control of the whole thing, then probably what you are doing isn’t very vital.”

The trick is finding the edge without going over the edge—arriving at the edge without seeking it, without using it as a clutch.

On Charlie Bleecker's podcast, I remember synthesizing one of her points about good memoir: "relinquish the urge to slant the reader's interpretation of you" (something like that). The idea is to show only the facts, even if they make you look bad—to feel comfortable with somebody seeing you without you explaining yourself.

In a recent draft she reflected this feedback back to me:

"What would happen if you repossessed your past Michael who lived in Miami? And left your present self off the page? Here's one more passage from the book:"

I wonder if this maxim is always the case, or if there are some cases where you want to sit in the present, cast back, and interpret. Maybe it’s 100% for memoirs, but 50/50 for essays? Either way, I find that (a) my Miami self is so distant from my current self, that I'm not even sure how to authentically recreate it, and (b) I cringe at that self, and at the idea of a reader misconstruing that past self for my present self (but in memoir, that cringe is the point. I think).

It points to a bigger question on the writer’s role of interpretation. I don’t think it’s zero. But I also think it’s annoying when writers over-interprets, or doesn’t leave any space to let the reader do some interpreting too.