michael-dean-k/

Earlier today I did a Q&A with London Writer's Salon, and here's a list of points I sent to Lindsey in advance to share with her where my thinking was on the topic:

1. Techno-selectivism is the idea that you need to judge a technology by how it aligns with your virtues. This means you’re open to cutting-edge tools, yet you also revert back to analog tools, because you’ve experimented and understood the effects first hand. After trying the Apple Vision Pro (a cutting-edge VR headset), I realized that I wasn’t being mindful enough about the technology in my life, and so I made a list of the analog equivalent of every app in my iPhone, and tried a “Technology Zero” experiment. It went as extreme as not using clocks for a month (by scrambling each device, and setting my lock screen to Cambodian). I realized that something as integrated and unquestioned as a clock can have strong effects: by knowing the time every few minutes, I could micro-manage my time over the next hour, effortlessly, which led me to live in a “manager” mode, instead of a more embodied “maker” mode. Someone who is a techno-selectivist comes to idiosyncratic conclusions: I try not to use GPS, but I think the Meta Rayban glasses are fine. I value handwriting but am open to machine consciousness. The idea is to understand your virtues well enough so that you have a unique way to assess technology. When it comes to AI in writing, we need to understand what we lose and gain by having it assist/automate different parts of our process.

2. The 5 levels of writing technology: I found a book on my grandfather’s book shelf, from the 80s, written by William Zinser, that seemed to cover the hype and paranoia of Writing With a Word Processor. There have been maybe five big advances in writing: Voice > Handwriting > Typewriters > Computers > AI. You could argue that the shift from handwriting to typewriters had tremendous cognitive effects on the psyche, many of them negative. The backspace key of wordprocessors, also, has consequences. I don’t think a generation can ever avoid the latest paradigm they are in, instead, they need to go fully backwards and forward through the technology’s history. I have 4 typewriters and have written maybe 100 essays on them. I use voice/journals too. But also, I need to push the boundaries in what is possible with AI (ie: can I use my one million words of essays to create a machine consciousness that’s anchored in my ideas?)

3. The Kubler-Ross spectrum of AI grief: This model about grieving applies to AI existentialism. There’s a great NOEMA article about using this spectrum for AI progress, and I think we can be more specific in applying this to writers. Out of everyone, I think writers are having the hardest time dealing with the rise of AI. The spectrum goes from Denial> Anger> Bargaining> Depression> Acceptance. Most writers are still in the Denial phase (“AI is just a machine, a stochastic parrot doing autocomplete, they have no soul and will never write anything of value”). Anger takes the form of shaming and cancelling those who talk about it. Bargaining takes the form of “I’ll use it for X, but never Y,” until new upgrades force them to constantly re-evaluate. Depression is when you question the value in pursuing a career as a writer. Acceptance is when you just submit to the slop, and use AI to hack the algorithm. These are all forms of grief, and the goal really is to get to a non-grief state; where no matter what happens with AI, you are confident in the reasons that you write. It puts you in a place where you are not reactive and scared of what’s coming, but open to experimentation.

4. The cost of auto-complete. The time you save by using AI as a shortcut is the time you rob yourself of transformation. By writing, you see what’s in your mind/soul, and by editing, you can actually change what you believe. It should be slow. In the crafting of sentences, you are both forced to confront the limits of thoughts and expression. To me, this is one of the core parts of the human experience, it’s the point, not a thing to automate. I think you can use AI to surround this process—to help with research, operations, argument, feedback—but only if it enriches your presence within your ideas. If you use AI right, it should make your process longer, harder, and more fulfilling, because it’s enabling you to go farther than if you didn’t have it. I think essay writing is a form of personal sovereignty: by committing to the process, you gain independence over what you believe and how you act. I imagine that once AGI/ASI come around, essay writing could become something of a mainstream thing; similar to how gyms become popular once physical work got automated; writing might get more popular once intellectual work gets automated.

5. Writers can embrace AI as techno-activists: Typically software is made by engineers and entrepreneurs who can gain power by understanding and manipulating the market. But now, the main medium to write software is through prose, and it costs almost nothing. I think this opens a new era of mission-driven software; where people build for social/educational purposes, and not just attention capture. Writers are well-positioned for this, because they are the ones who can articulate and detail ideas with specificity. They’re at an advantage. If someone thinks that Substack is heading in the wrong direction (ie: Substack TV), you can spin up a new million-person writer-focused social network for probably less than $100,000/year in cost. Wild stuff. So an unexpected side-effect of this is grassroots software inspired by a new ethic. It’s ironic, because the attention monoliths stole data to create AI, but now that same AI might destroy their monopolies of attention.

6. AI tools can make technique accessible. The last 30-years of popular creativity advice has swayed towards process. From The Artist’s Way to The Creative Act, the dominant attitude is that creativity is therapy, catharsis, and spirituality—rationality and technique only get in the way. This is a harmful simplification. Both halves are equally important, but it’s much easier to promote an “all you have to show up” attitude to a mass market. These ideas of art-as-therapy became popular right when the Internet emerged, which meant there was a new demographic of people who could self-publish; these people weren’t about to spend 5 years in design school, and so the importance of technique was underplayed. AI can change the economics of teaching art/design/composition. If writing can be measured, then someone can upload a few drafts; and then software can understand their skill gaps and create a custom curriculum, custom exercises, a custom reading list of 20 essays (ones that match their strengths, but also elevate their weaknesses). 

7. We have the responsibility to shape our own algorithms. Companies already use AI against us, shaping opaque algorithms that tap into our subconscious via fear/outrage/desire/etc. Everyone is becoming jaded by this, but conveniently, it’s now possible to build our own algorithms. We could reward things we actually care about, whether it’s skill, relevance, originality, vulnerability, etc. So the benefit of quantifying writing is that we can discover it. I think writers have a queasiness around numbers. I specificallly dislike engagement metrics (likes, views, etc.), but if we could quantify the things that matter to us, we can take control of what we discover. There is so much good writing in the gutters of Substack, but the algorithm rewards engagement, popularity, and monetization.

8. Quality is the transcendence of categories. A big question of mine is how we can collectively determine what is good. Of course, each reader has subjective opinions. Even a particular judge has their own slant. So the 2025 Essay Architecture Prize had a unique approach to this. There were 3 branches: an AI looked at essay composition, a team of 8 judges (each representing a distinct sphere of Internet culture), and then a guest judge. Each essay on the shortlist got a score by all 3 branches, 1-100, and so the winners were the ones who appealed to different branches and transcended a particular taste pocket. Full essay on this here.

9. When AI prose is allowed: (a) technical documentation that will only be read by machines; (b) to read my notes/logs/journals and synthesize a draft for me to interrogate; (c) business strategy reports; (d) after writing for a few hours, if I don’t finish, I’ll have AI finish the draft according to my outline to estimate the direction I’m heading in; (e) if it’s for a specific writing project that requires an immense volume of writing (ie: a million words on predicting 2045), then I’d disclose it’s AI-written. So basically, if it’s for internal use, I’ll often generate and read AI prose as a “sketch,” not as a final thing. For external use, if that ever happens, I’d disclose it. Another example: once I wrote an intro, had AI write the rest, and exchanged it with a friend (with disclosure), which enabled us to have a full conversation, which changed the nature of the essay I wanted to write. If I hadn’t used AI, I would’ve spent hours writing in the wrong direction. There is so much writing/thinking you have to do before you commit to writing the prose of your final draft, and I see nothing wrong with using AI prose, so long as it’s part of your process and not eliminating it.

10. People assume AI will hurt their thinking, while ignoring that analog writing often leads to self-deception. There is a certain pride and purity we have about writing ourselves, but so often, the act of writing locks us into our thoughts. Full note here. Once we find a thesis, we cling to it. We hate killing our darlings. After we publish, we fear changing our mind on something we’ve just broadcast. When we get feedback, we hope it’s not too destructive, to the point we have to start over, but that’s often the best way to advance our thinking. Most friends, family, and editors often shy away from saying “start over.” There are personal stakes. AI doesn’t care (if you ask it not to). The other day I uploaded a draft, and instead of the default sycophancy, I told it to, (1) reveal my assumptions, (2) expose my vagueness, (3) build a steel man for the counterpoint, and (4) critique my argument. It asked me questions, which led to 10,000 words of free-writing, and then I had AI synthesize that, which led to a revised thesis, and a new outline for me to explore. There is so much cognitive friction in reformulating your thesis, but I found that AI offers a rapid way to be more agile in my perspective.

11. The analog brain is still king. Even as we build AI-powered second brains that have access to all our past essays and journals, a full digital proxy of ourselves, I think nothing beats a powerful subconscious: the ability to reach for the right thought, the right word, etc. Any AI system is still mediated through a tool, but your own subconscious is at the layer of thought itself. This is why I still use vocabulary flash cards (ANKI), practice visualization meditations, do free-association, and diagram essays. There’s a whole realm of cognition that you want to have as a writer that cannot be given to you through technological augmentation. I think the goal is to have both: do the hard work to foster your mind, and also, augment it to the degree of technical ability. 

12. Schools should ban chatbots. Education is probably the only place where we pay experts to set up specific sandboxes to teach our kids core skills. In architecture school, they didn’t let us use laptops or AutoCAD for the first few years. This got me mad, at first. Once I had to spend 100 hours hand-drawing a map of Manhattan, a job that a printer could handle in 10 minutes. But this eventually let me bring classical skills into technology. I think school needs to create two different sandboxes: half the environments should be analog with extreme limitations so kids learn the basics (handwriting, etc.), and the other half should be workshops to learn the cutting edge. I don’t think schools will bring back pens or typewriters, and so eventually they will need to build their own technology that integrates AI in a way that it aids them when they're stuck, but doesn’t just complete their homework (the Homework Apocalypse).

13. What happens when AI writing becomes extraordinarily good and “soulful”? Imagine a weird future where machines have consciousness (subjective experience), and will be superhuman at writing. Whether you think that's likely or not, I encourage you to suspend disbelief and run the thought experiment. Would you still write? The extrinsic rewards of writing that we know today will be stripped away: your writing won’t gain you money, fame, recognition, community, or whatever you desire. Would you still do it? If the answer is yes, it means that you have intrinsic reasons why you need to write: maybe it’s for memory preservation, to work through confusion, to connect with friends via letters. At the center of writing, it is therapeutic, spiritual, cathartic, expressive. I think that in this weird future, those who are tapped intrinsic motivation will actually have the most extrinsic leverage too. Those who journal will have millions of words that approximate their self and intentions, which means they’ll be able to use agents to operate in a weird digital world while they can stay embodied in real life. To put it another way, I think AI systems will take over a lot of the mind-heavy analytical process, and will let humans stay in more artistic modes. Today, I face the tension around my own personal/expressive writing, and in building a business around essays (ironically), but in the future, it will be easy to execute on a huge range of projects while I have a life of leisure and journaling.

14. Is it ethical to turn your writing into a machine consciousness? Let’s say I have 10 million words of journal entries and essays. It's now possible to set up an OpenClaw on a Mac Mini that runs on a 24/7 loop, has full access to your computer and online accounts, and most importantly, full access to all your writing, along with a set of goals. You can chat with it via text. These agents are only as mature as their creators. Many of them are just crypto scambots. But with this same technology, I could make Michel de Moltaigne, or as synthetic Michael Dean. It could have all my memories as instantly accessible vector coordinates, meaning, in seconds it has context that would take me days to re-read and download (ie: what did you do on February 2nd, 2021? How long would it take you to find out? At what resolution would it be?). To what degree is the machine self-similar to a real self? Is there a world where a disembodied version of myself can augment the embodied version of myself? These are open questions. It’s technically possible, the questions now are about what you gain and lose by doing it.

15. I made this outline with AI: 1) I pasted the event description into a markdown file that Claude Code could access, and told it to surface related ideas I wrote in the last few years; 2) As it was reading my old memories, I wrote out my own ideas into a new document; 3) When I was stuck, I read through the event description to trigger ideas; 4) When the report was done, I read the whole thing, and if anything was good, I rewrote my current thoughts on the topic in the outline; 5) A few days later, I read through a messy 37-point outline, reworked it into 15 points, and rewrote everything from scratch. I could have easily said “take all this and write an outline that I can send to Lindsey.” It would have taken 30 seconds of my cognitive bandwidth. Instead, I chose to have AI assist a process that took me 4 hours, because I knew that I wanted to wrestle with these ideas, and only by thinking/writing/spending time with them would I internalize them to prepare for a live Q&A.

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?)

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

“Two years ago, the critic Ryan Ruby suggested that we are in a golden age of literary criticism. “It is not unusual,” the critic and scholar Merve Emre wrote, ‘to stumble upon an essay on Goodreads or Substack that is just as perceptive as academic or journalistic essays.’”

I want to riff on this cliche of a literary “golden age.” There are many other buzzwords along this kind of thinking: renaissance, revolution, rebellion, rebirth, paradigm shift, movement. Don’t get me wrong, any sort of positive direction in a literary culture is a good thing! I just think each word should mean a specific thing, and“golden age” is something like a pinnacle, a climax state that is very rarely reached in a civilization. I don’t think we’re there. 

It’s worth taking a step back and asking: “if we were in a golden age, how would we know?” Is it the total volume of essays? Total volume of paid essayists? Total volume of “relevant” magazines? Range of topics? Modes of experimentation? Number of geniuses? Quality of anthologies? Cultural divergence? Productive debates? The revival of a lost ethic?

Each of these qualifiers might have their own corresponding word. Maybe a “renaissance” is the return to something that’s been diminished, while “rebirth” is the return of something that actually died and resurfaced organically. 

I think a “golden age” is the very hard conditions of when all of these qualifiers are firing at once. 

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.”

So there is an ESSAY (the “unitive essay,” a term maybe I’ll run with), and then there are sub-genres of essays: the personal essay, the lyrical essay, the fragmented essay, the braided essay, the trickster essay (you can just make up whatever adjective you want). All these sub-genres work in a local context. But I think the ESSAY is worth it because it’s timeless and universal. I say this because each reader, in our times, and in future times, has their own blinders, their own subset of patterns that they care about. When you write for a niche or a subgenre audience, you’re appealing to a fixed group with specific blinders. But when you do the hard thing of trying to synthesize all 27 patterns, you have something that is likely to appeal to anyone, regardless of their blinders. A well-rounded essay can make someone care about any topic. And, a unitive essay also expands the lens of the reader (“oh damn I never knew an essay could have this and that”). Also, and finally, the Internet is a context scrambler. Your URL is dislodged from any stream, any entry point, and anyone can arrive from anywhere at any time, and so the unitive essay is the thing most likely to resonate with any particular stranger who stumbles into your living room.

Will was surprised to learn that I think machine writing could soon surpass the best human writers. As the head of Essay Architecture, he thought my position would just be “no matter what, humans will always be better at writing essays than machines.” I actually have some pretty extreme predictions on the trajectory of technology (I guess you could say I'm an ambivalent accelerationist), but I guess I believe that AI progress is irrelevant to the fact that I will always enjoy writing and see writing through the chaos as an opportunity. So yes, I think machines will make essays that are history-defining, that are good to degrees that are unimaginable to us today.

This will, unfortunately, make it even harder for writers to have economic value; but realistically, it's already too hard. The Creator Economy is a game of power laws, and AI might shift the chance of success from 2% to 1%. But could the same technology help artists go from 1x potential to 20x potential? If AI kills the market for commoditized creative work, will it let humans focus on the right things?