michael-dean-k/

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.

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.

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.