michael-dean-k/

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

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

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

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

Reading for ideas

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

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

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

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

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

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

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

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

Other ways to read

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

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

V7. Analog editing is pretty fun. There’s something helpful in seeing your older frozen version beneath the new thing emerging. I do this a lot in Miro, but feels different on paper. Can’t quite articulate why yet, other than the ease/freedom of drawing. Just feels like there’s value in moving up and down the writing tech stack (voice, handwriting, typewriter, computer, AI). 

After this whole analog ordeal, I distilled my essay into a new question, and then ran it through a new vibe-coded essay interrogation app I made, before it one-shot generated v8, which sucked (as a whole), but also unknotted a lot of the big v7s issues. So next step is to make a digital outline for v9, where I’ll meticulously look through all the notes and scraps and refile the good parts into an new outline, and then maybe typewrite the final version in one huff. 

I think the point I’m arriving at is that every medium has its strengths and weaknesses, and it helps to shift around to get the power of each, until you find a version of the idea that feels right. (Of course, this is very inefficient and slow, potentially endless, but probably worth it for the few ideas you care about most, and so that’s why I’m trying to be more rapid with notes like this, so I’m less rushed on the whale essays.)

This helps clarify my stance on AI writing too, that it can be helpful for sketches that advance or challenge your thinking, but it should probably never be the last link in the process, because the essay you share should be the best articulation of your own thoughts in your own words. Typically AI is framed as a shortcut for slopjockeys (which is fair because that’s how it’s commonly used—I mean my wife and I just had to file a warranty claim for our broken stroller, and it’s not worth wasting prose on that), but if it extends your thinking, and points you to new regions of pondering when you shower or drive, which then inspires original ideas, is that cheating?

Recently found a book on my grandfather’s bookshelf by William Zinser (author of On Writing) from the 1980s on word processors. Apparently he started as a technophobe, but after actually buying an IBM and moving up the stack, he found it to be a pleasure that augmented his methods and habits from earlier mediums. I think the unique paranoia of AI is that it can easily replace and cheapen your whole process if you let it, but that’s your choice, independent of anyone else.

I like the word experimental because it fuses two halves of a process we don't usually link. What we typically mean is divergence, deviance, tinkering, norm-breaking. Weird stuff. Think avant-garde John Cage soundscapes where he makes music with only kitchen appliances. But also, the word points directly to the scientific process: to run an experiment means to set boundaries, gather insights, and test a hypothesis. Either mode alone falls short. Endless mutations burn you out, and rigid systems can't take you anywhere interesting.

Many of the original experimental artists were scientific. Kandinsky didn't just make abstract shapes, he developed a systematic theory on how colors/geometry provoked specific feelings, and then at the Bauhaus he used questionnaires to test which of his theories were true. I don't know exactly when this happened, but as weird works became mainstream, the word shifted from a process to a genre; the way it was made mattered less than the fact that it was unusual.

Experimental drifted into a contronym, a single word that contains opposite meanings. The power in the word comes when you re-unite both halves, entering strange territory with an analytical eye.

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.

This essay tapped into a striking definition of timelessness. He doesn’t get there until halfway through though, and I found myself disagreeing with—or at least, questioning—a lot of his earlier points (I’ll come back to this). The main point is distilled into this: the best essays are “ineffective” because they reveal the timeless problems that each generation fails to synthesize. Timeless essays speak to the common foils in the human operating system: the blindspots of parents, the lies of institutions, the avoidance of mortality, the ineffability of relationships, the mundanities that are never captured in enough detail. These are different than “discovery” essays, like Darwin’s Origin of Species. The holy grail of an essay is surprise, and a timeless essay is not just sueprising for one generation, it’s surprising for every generation. And so timelessness, then, is a type of “breadth of applicability.”

PG also ventures into a familiar territory of “essay as a mode of thinking.” Where as in the past he used “the river” as his metaphor (2004), this time it’s a tree. You start from an origin, and then you explore many different branches in search of generality x novelty. What is a good starting question? He says a good one is “outrageous, counterintuitive, overambitious, and heterodox.” It doesn’t have to be a complete thesis, but some puzzling gap, and importantly something you care about. You won’t be able to stretch an origin question into cascading insight unless you have a unique angle into it. The origin doesn’t matter too much though, because it’s a recursive process, and you can eventually get to the best question in “a few hops.” I love how he emphasizes that you need to write to explore branches of a tree, and there are many dead ends; you realize how you are mistaken, incomplete, and inelegant (you go from vague to bad). Don’t get discouraged by these; finding your false assumptions is possibly the only way to really begin.

Despite loving his whole exploration of “mode,” I don’t think that means you have to neglect essay as “genre”; he says form/style don’t matter in “the best essay,” and I disagree, obviously. He has Darwin as the pinnacle example of an essay, and I’m really challenged by that (I definitely have to read it now). Is that an essay or a scientific paper, just captured in shortform non-fiction? He seems to imply that the essay is at its best a vehicle for discovery, as a mechanism to bring forth surprising, important, and useful ideas. From the creator of “make things people want,” this isn’t surprising. Even though a new theory of evolution had broad implications for society, I assume the paper itself is technical, intended for a scientific niche audience, which in my mind, makes it more like a scientific paper than an essay. An essay is something that is universal/general enough for the average person to read. An essay, I think, functions like an information transfer system between specialized facets of society; it’s about making your specific niche legible to all the other niches, and I don’t think that was the specific goal of Darwin's writing (even though it was inevitably understood by everyone, it wasn’t through the writing, but from the effects of the writing).

(Added: Another note on Graham’s notion of best as timelessness: he says that timeless esasys are the perennial insights that each generation can’t absob. This implies that the insight is never enough: even if you know something, there is often a lack of wisdom in applying it to your own circumstance. And so really, these unteachable lessons are ones that can only be obtained through personal experience. Does this point to the fact that all essays need to be personal? Maybe bland insights can’t be digested by a reader, but if they are integrated to vivid personal experience, experience vicariously, then might this actually be the best medium to transfer wisdom?)

Waiting for my wife, I am sitting in the lobby of a firm I quit 4 years ago—though I haven’t entered the building in 5, since COVID—and I see Westler slip out the elevator bay; out walks Westler into the barrel-vaulted lobby, out through those gold revolving doors that started and ended many days of my years. Westler. He’s still here! Alive! I remember him like I do an old dream. His placid demeanor and dry humor, a goatee, his subtle mischief and possible creepiness. I don’t know if I ever really knew him behind that caricature. He designed multi-story basements for megapolic airports… I think (a kind of endless machine work, the coordination of billions of lines, cognitive sterilization, a tectonic death in service of a suitcase city, a labirynth of conveyor belts). Is he doing that same thing? Did they find some new VR guy to render his city of luggage? Of course I know absolutely nothing of Westler’s life—for all I know, he has a pearl of a daughter that makes sacrificing his peak hours worth it, forever—but in my assumption, that the company we both worked for is something of a life-sucker, a hunter and skinner of the young and ambitious, a building broker that drools steel angled towers across the East, across Dubai and Korea and Singapore, an entity in Bryant Park that overworks and underpays but leaks enormous partner bonuses that enables the CEO to buy luxury pets and park penthouses while speaking at Venetian conferences on the virtues of design, I imagine Westler as a sleepwalker. I imagine every day of the last five years, as he wisps out those gold-trimmed revolving doors, he finds relief in his break, but doesn’t stop to question the sacrifice, and knows not the basic mystery, “time flies.”

Now that I’ve retrieved my wife from the grips of her Tower, we are back in Penn Station—because no more trains run out of Grand Central this late—and we see a familiar figure, a man on fentanyl hunched over at 90 degrees. “Is that the same guy from this morning?” My wife said sadly; but I said, given he spent his entire day in the same spot, same position and same trance, he looks to me a whole lot like Westler.

This is an extreme comparison—to compare the default path to a lethal addiction—but it tracks to how I feel, an anger over a design firm kidnapping my very pregnant wife.

This morning I finally visualized the whole chain of command, the reason she works until 4am, and why 1 AM is considered a “good night”: somewhere in Dubai is a very rich man, and he’s decided to cure the anxiety over his massive pile of money but funding a Tower that, most likely, no one will live in. So he hires a team of henchman, the “client reps,” and it’s their job to dangle glamorous limitless design work to very hungry architects that fear the market could evaporate at any moment. So naturally, the firm accepts the work at half the rate, and I assume half of that is just cut off the top to reward and keep the partners fat (the 80%, the staff—they don’t matter, they are burnt and churnt over, with eager beardless faces eternally sending resumes, because where else in America can you build DUBAI). And so the client, being entitled and aware of our desperation, will throw a screaming fit if my wife and her 2 juniors can’t pull off the labor of 10 people, every single night. Staffing can’t be honest because it’s trying to survive, and business development can’t be selective because it knows it’s runway, and so what emerges is a kind of caste system where office workers are expected to work 80 hour weeks without overtime or questions.

If you have an essay with poor conflict, poor cohesion, poor sequence, it’s very possible AI won’t know. AI struggles with essay structure because it thinks through non-linear vectors. A human can easily tell when form is off, because they are slowly reading through mazes of text, from beginning to end, and don’t know how everything connects. Often, only at the end, will they find the key that was necessary to unlock the cryptic prose they just waded through. AI, however, process the whole essay at once. Meaning, it reads the essay insanely quickly, converts it all into math/vectors, and then applies your prompt. It's hard for it to know if your tension is working because you've already spoiled the ending. This is a case for why you need atomic evaluation to either generate/analyze essay form. I needs to think step-by-step (possibly through separate prompts) in order to simulate the linear experience of structure.

I wonder if it’s impossible to get an LLM to write a great essay. It might. But I think it’s easier than people think to build a good AI writing tool on top of an LLM (though not something I personally want to do). The problem is we have an LLM bias, and the way that essays get formed are very non-LLM. It’s not like a prompt can turn into a higher-dimensional mathematical object and then summon a whole essay form. 

An essay is a mode of thinking. I don’t mean to imply that a machine “can’t think,” I mean that analysis and thought takes time, and LLMs are writing 100x faster than required. 

An AI writing tool would need to prompt a sentence at a time, and pause to “reason” for a minute or so: what did I just say? What are the possible things I could say next? Of those things, which belong in this paragraph, which in the next? What sentence length might be effective given the idea and last sentence? Now that I’ve chosen my idea, how should the tone modulate? What words or phrases belong in the sentence? And how should I structure the sentence? You get it. 

In any given sentence, there are dozens of decisions. I think an AI could be decent—if not amazing—at thinking this through, but they’re asked to write 2,500 words on Hegel at point blank. Good generative writing can’t be done through up-front vector math, but through following a mode of thinking (incremental and context-laden vector math). The implication here is that the AI might take 3-10 hours to write the essay, similar to a human.

Put more simply, you would need a tool that reasons after each sentence and writes/saves variables that can be called upon for future sentences.

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.”

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.

"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.

I'd like to better articulate my impressions on the New Yorker over the last year. First, it’s too political to trust. I want to read great cultural writing from them, not politics. It feels like part of an agenda, and makes me wonder if the whole magazine is compromised: a propaganda vehicle rather than a place for essays and opinions. Even the “mail bag” feels strategically curated to generate uncritical dissent; they want me to mimic their dissent, but I’d rather derive it independently.

Separate from that, I’ve found the non-political essays (if you can call them essays) to be boring. Why? The New Yorker is a “product” that taps into a particular urban aesthetic, meaning it’s more about rehashing a predictable and consistent tone than publishing original, interesting, or rogue acts of thought (surely, this is what happens in cities more than anywhere else).

I scored the latest essay I read of theirs a 2.85. It excelled in paragraph form and vocabulary. To basically any reader, this would be flagged in their mind as “great writing.” In a way, it is. But as an essay, a specific genre, it lacks. There’s no authorial perspective (it’s more of a profile); there’s no real debate (it’s one sided); it’s missing a cohesive thesis; and the tone is … what is their tone? Erudite, dry, witty, understated irony. It seeks authority through a false conversationality. It is “cultural” and gives specifics, but has no imagination. The essays are mosey-like: lazy, unhurried, with no tension or spine, as if you have many hours to read through their ambles. There are snobby asides with little uncertainty. There is limited register of emotion, rarely rage or ecstasy, even in topics that would warrant it. They are occasionally cheeky, but never sly, slapstick, bawdy, or archaic. It is metropolitan, coastal, a business-class professional style of writing that takes no risk. Of course, writers vary, but this is my take of their overall editorial stance.

In the end, The New Yorker is tonal product: they’re known for a house style, and they bet on the fact that through locking into a particular tone, a good amount of readers will buy into it and get high off reading it each week. It is less about expanding your thinking, and more about helping one gain status by training themselves in an ethos of haughtiness. Good essay tone is dynamic, evolving many times from beginning to end; The New Yorker’s tone has been static for a hundred years.

The covers are great though, I keep them in my apartment as decorations.

In SF I bought a book of letters from Neal Cassady written to Jack Kerouac. Cassady was the real-life companion to Kerouac on his road trips, the real-life Dean Moriarty. He is little known outside a certain circle, but a legend with it. Recently read an article that referred to him as a “sacrificial muse”; he enabled others to make their best works, but struggled to make anything meaningful himself.

Why might I be so inspired by him? In many ways, he’s a terrible role model, but I asked GPT-5, based on what it knew about me, why I might be inspired by him":

Assumptions: you’re attracted to catalytic energy, improvisational intelligence, and scene-making; you want wildness harnessed by form; you value unfiltered truth, high throughput, and culture-building more than polite careerism. Cassady is the archetype of kinetic mind-as-engine: he didn’t just write—he ignited rooms, cross-pollinated tribes, collapsed life and art into one continuous performance, and served as a human router connecting Beats → Acid Tests → Dead. You’re drawn to that throughput: the low-latency cognition, the riffing monologue that finds shape in motion, the willingness to live at the edge where new forms appear. As a builder of Essay Architecture, you also recognize the meta-lesson: Kerouac’s “spontaneous prose” needed Cassady’s voltage to spark but also needed editing, constraint, and a chassis—the exact dialectic you’re formalizing (flow vs. grid, spiral vs. structure). You like him as a role, not a role model: the driver, spark plug, transmitter; the person who turns a private idea into a public scene. And you’re repelled by his collateral damage (self-immolation, chaos, irresponsibility), which sharpens the prescription: steal the engine, not the wreck.

After reading more, by them and from them, I'm realizing that Kerouac and Cassady are moral failures and tragic stories, nothing to aspire to without extreme caution … I really ought to figure out what I ever saw in them, and see if it’s separable from their painful lives, or if they just inevitably come together … (I think this as I look at the inside of my right foot in my dark living room—almost midnight, still on SF time—and how the light from the kitchen illuminates 13 separate bulging veins and I simultaneously wonder if I’m fooling myself with this whole writing dream, and also, if I will die young from hypertension.)

Cassady’s mom died when he was young, his dad was a drunk, homeless hobo, so from 10 years old and on, he was alone and un-parented. He stole over 500 cars, and spent many years in prison. Apparently what others saw in him as enthusiastic energy, he later confessed was extreme anxiety.

Kerouac’s brother died young when he was 4. His father hated his writing, and he was tight with his mom but she was extremely Catholic and made him terribly guilty and resentful of her.

Ginsberg’s mom was a paranoid schizophrenic, in and out of psych wards, and often trying to kill herself.

They all had troubled childhoods, and that probably messed with their emotional regulation. They all seemed to dabble with mental breakdowns and suicide. There’s a letter Neal wrote where he kept drinking and had a gun to his head for 14 hours but couldn’t do it, and then his wife came home and he asked her to do it.

Their specific energy might have come from extreme psychic trauma. Worth thinking how to channel a genuine intensity of enthusiasm, without accidentally emulating their specific flavor (which you can’t fake because it’s rooted in pain).

What is a “beat in the suburbs”? ie: What is the distilled spirit of the Beat Generation without nomadic self-destruction and the romanticization of chaos? I say “in the suburbs” because that image is antithetical to “being On the Road,”; it helps clarify that what I see in the Beats is something different from the spirit of adventure.

Values to keep:

• authentic experience > social performance
• deep friendships > shallow acquaintances
• questioning conventions > agreeable
• singular destiny > societal cog
• madness in creative work > productivity
• spiritual focus > material focus

Differences:

• Stable home, stable family; but mindful travel
• Not about spontaneous output, but showing up regularly
• Editing isn’t antithetical; it actually aids future streams
• Consciousness expansion doesn’t have to be through drugs

I like this AI-summary:

“It’s Beat ideals with adult emotional regulation and an understanding that you can be countercultural without being self-destructive.”

Tommi Pedruzzi, poolside in a black tank, generating niche-targeted slop for KDP eBooks, making $323 a day, and gracious enough to teach you how to be a leech of the AI revolution.

This is mean, and I don’t know anything about this guy, and maybe he’s fine, but my reaction is as strong as it is because his values are so antithetical to mine. It reduces publishing words to: (1) having AI select your niche, (2) having AI write your outline and book with trite prompts, (3) tricking consumers who think a title will fix their life, and probably won’t even notice it’s slop. It glorifies money and market hacking, and sees the whole project of writing as an instrument.

What’s sad to me is he’s made $3M by age 27, and instead of using his relative financial freedom to unlock cognitive freedom and originality, he is still promoting his own brand of slopjockery. Either he’s lying or infected, and I hope he’s lying.

(Further reading: Inside the Amazon Slop King's $3M Hustle)

#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.

I'm reading Farnsworth's book on Classic English Metaphors and I’m starting to understand metaphors and similes as SVO equations (Subject, Verb, Object).

Some of them are straightforward and simple:

“A professor must have a theory, as a dog must have fleas” : SVO = SVO (or, 2(SVO)).

“Her voice was thin like the buzzing of a mosquito” : SV = VS.

Then some of them lose their symmetry and add adjectives and prepositions to add complexity.:

“To talk to those imps about justice and mercy, would have been as absurd as to reason with bears and tigers” : vSo^2 = vS^2

“Harry, champion, by acclimation, of the college heavy-weights, broad-shouldered, bull-necked, square-jawed, six feet and trimmings, a little science, lots of pluck, good-nature as a steer in peace, formidable as a red-eyed bison in the crack of hand-to-hand battle.” : Sa^11 = aSa

And of course, since many of these examples come from English writing in the 1600s-1800s, there are a few that are quite complex:

“If the typical criminal is degenerate, bound to swindle or to murder by as deep seated an organic necessity as that which makes the rattlesnake bite, it is idle to talk of deterring him by the classical method of improvement.” : aS1n, aV2 (=a^2 n=) S2V + VS1pan

What are the types of telling? (in show vs. tell):

1. Telling is compression; instead of showing us a specific moment of when you were alone in the woods at the night, you compact the story and say “I'm scared of the woods.” In compression, you lose the details that help us get why (the weird sounds, the dead trees, etc.). It is oversimplified to insist that you should show every idea in lucid detail. It's too much to take on. You want to compress the inessential to create a hierarchy, so that the essential details are given space in proportion to their importance.

2. Telling lets you connect the dots and find patterns: “the definition of terror comes from X, and this relates to Y, and so it means Z.” If you want to come up with principles, you have to abstract things down to compact, vague placeholders; it’s the only way we can hold multiple things in our mind at once to see the relationships between them. The problem, when writers only exist in this word of abstraction, it’s dense and boring.

The trick isn’t to pick one mode or the other (show vs. tell), but to master how you blend between them. It means you can actually write about X 2-3 times, even in a single paragraph. ie: first you locate X (tell), then you show X in extreme detail and emotional power (show), then you connect X to related nodes Y & Z (tell). This is a tell-show-tell sandwich, with 75% showing. It gives you both depth (by showing) and width (by telling).

This means any piece of material you have is fractal. You have to be able to zoom in to find specific examples, and zoom out to find principles and patterns. A writer/editor needs to always be bridging between abstract and concrete; if someone gives a principle, they’ll say “give me an example,” and if someone gives a story, they’ll say “what is the larger principle?”

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.

Garret on numeracy:

I suggest spelling out either: (1) all numbers below 10 or; (2) all numbers below 20 or (3) all numbers below 100 with the exception of your chapter references. If there are too many numbers like this in your pose, then the important numbers won’t stand out as much, like the reference examples later in this paragraph. Garner prefers option 1. DFW prefers option 2. Chicago style is option 3.

My reply:

Given different writers have their own range, is there a case for “all numbers below 2”? I’d argue that anything that is a quantity, other than a/one, can justify being a numeral: 1) it creates a visual fabric, where all quantity gets a specific symbol, and 2) it’s create the least readerly friction (I look to reduce this where I can because in other areas I intentionally add friction for specific ideas/phrases. To spell out “seventy-six,” in my mind, is a poor use of someone’s mental resources, an unnecessary drain of stamina. Even “7” over “seven” saves a few milliseconds of stamina that I will expend elsewhere. Also I love numbers. I’m really a math guy, and all my prose is just really filler between my numbers.

Here are some idiosyncratic rules on how to make these decisions:

1. If two numbers occur in a sentence or a paragraph, use numbers so the reader can effortlessly see and compare quantities in a pre-read scan.
2. If you have a set of labeled or numbered items to make a framework (a, b, c) or (1, 2, 3), you can default to spelling out a number so it doesn’t appear to be part of the framework.
3. By intentionally spelling out large numbers, you make a point (“we waited for one hundred and twelve seconds for the waiter to return”). The delay of processing numbers can be used for effect.

This is a good example of rebelling against prescriptive, absolute rules: “everything under 10 must be spelt out.”

The advice that our writing voice should never be passive comes from overfitting marketing advice to essay writing. Yes, sales pages on websites warrant a particular aggressiveness in tone; in that context, there are many things to click on and you’re trying to communicate clarity in the quickest possible time. Essays are not like that.