michael-dean-k/

Hey [ * ],

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

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

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

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

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

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

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 declared to my wife this morning that DeantownOS is getting retired. It’s been 3 months since I spiraled into Claude Code for personal systems, and I’m at the point in the curve where the amazement has normalized and I’ve accepted the fact that I’m in a trough of disillusionment. The question now is revise or abort.

The case for aborting ties back to Oliver Burkemann’s Four Thousand Weeks, which popularized the idea that all systems are methods to procrastinate from making hard decisions. They give the illusion that you can do everything, and since AI can meaningfully leverage the volume and range of things you can do, it tempts you to build galaxy-brained systems. The thing I think we fail to realize while in a vibe coding frenzy is the psychic cost to remember and maintain the stuff you build. Yes, it is appealing to “reclaim my computer” and rebuild everything I use as personal software (from Obsidian to Gmail), and it’s even possible, but it’s a new breed of Sisyphean struggle. Once you can mold your own software around you, it’s too easy to endlessly mold, to lose sight of the work and just tinker on your exoskeleton.

I’m obviously skeptical, but I’m still a believer; if I were to revise, to rebuild my Claude stack from scratch, I would have to develop a few heuristics to help me from short-circuiting.

The first one that comes to mind is “will this matter once I’m dead?” Ie: writing an essay matters, because I imagine one day my daughter will read that and get to know me better, or at the very least, future Me in 35 years may enjoy reading words of my past self. But to create detailed daily files that get spliced into atomic “routing files” that then then get saved again to a new destination folder, which exist either as (a) just context for AI, or (b) require some manual effort to prune into something that matters once I’m dead, is to create waaaay too many layers of abstraction between the source and the Work. When I read back my writing from the last few months, only a small is valuable enough to be saved as "logs" in my archive. I was writing for AI, not for my future self.

I made this assumption that atomic daily files are the kernel of a system, and it was an axiom I could never undo. There’s maybe another principle on “don’t build load-bearing infrastructure on an unproven axiom.”

Another one could be “don’t assume future you will have bandwidth,” to do X every day/week/month. Every day I had to review how my AI system proposed to route my logs, and eventually I'd ignore it and get backed up. This means that if something isn’t truly automated, I should be very cautious of it. It's possible to do one little step forever, but not a hundred. Not every promise has brush-your-teeth-scale reliability.

What I’m getting at is that it’s not about maximizing or neglecting systems, but about understanding the right principles so you build something that is actually in service of your life.

I set up a chronofile, inspired by Buckminster Fuller's system, where he logged every 15 minutes for like 70 years. That's intense! I'm going to run an experiment. In the past I've operated under the premise of "capture as little as possible," as in, capture just what's worth it, because then you'll have a mess of notes to go through. But agents change this; all the yak shaving (tedious, endless work) is handled. This could lead to hyperlogging, 100-400 logs per day. I've done this before as a kind of Hermetic T1 ritual (from Franz Bardon), and it's an intense way to see everything crossing your mind. This scale of writing might be the best way to "meta-program" your psyche. Essays do this in a way, but an essay let's you go very deep on a particular idea (and you might be deluding yourself, or you might be articulating a take in an ideology that you'll outgrow in 5 years).

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.

To read someone’s logs/diaries is to let them enter your mind, whether you realize it or not. I don’t mean that figuratively, I mean it in the sense that by reading someone in such detail, you risk inheriting them at least, and at most becoming them. If they are articulate and prolific, it means that you contemplate a new form of existence. Even if you are ambivalent it, or even loathe it, it is such a volume of informaiton, that you risk forming patterns and assuming others of a similar type have a similar mind. I guess the question is, do you want others to be a mystery, to be imagined by yourself, or to be transferred from your understanding of self/other. My sense is that we generally transfer our own consciousness onto others, which is distorting, and so reading the logs of others is a kind of calibration.

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.

Walking through the architectural slop of suburban Queens, hot and windy, sandals digging into feet on a 20-minute walk from a bad haircut to the cute part of town to meet my wife, and now there are church bells. Typical ding dong pattern. And then three low, ominous hits. The new hour is here. Our Lady of the Blessed Sacrament. Power lines, planes, and Amazon trucks. Sun on a clean-shaven neck.

These details are arbitrary. It’s not enough to just render my in-moment perceptions into prose. There is endless detail and no time to turn each pebble. Which ones have significance? Which details create a third thing when you put two together?

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

Email to Davey:

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

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

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

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

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

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

Consciousness is something like the linear real-time awareness of state-switching between perception, memory, projection, abstraction, identity, and action (ie: phenomenological degrees of freedom). Logging is an attempt to rapidly and richly write that process so you can see what’s going on in. It’s possible that, in every moment, you underestimate the depth of what you could write. While filling out the medical paperwork at the OBGYN, each line triggers a thought that could be a paragraph (What’s my % chance of having a thalassemia gene? Was that imagined visual of our doctor as a witch stemming from my fatherhood anxiety? What year were these forms made in? Does someone manually input this into a database? Will that ever be used in some data analytics scheme to have any noticeable impact on my life? Etc.)

Fleeting thoughts usually pass by without noticing. The first step to logging is to become aware of them, which can only really happen if you find importance for them. If you don’t see your everyday thoughts as either a) embryonic ideas with potential worth developing, or b) clues to troubleshoot your problems, you have little reason to pay attention. One you are paying attention, you need some sort of filter, because you can’t give all thoughts equal attention. When you come upon a good one, you shape it, examine if there’s something good in there, and if there is, you write it to remember it.

I just set up something with AI that really unlocked my 3 year logging practice. The insight is pretty simple. For context to be useful, you want atomize it. A 1,000,000 word dump into the context window isn’t that useful. I mean, each model will get better at the “needle in a haystack” problem, but if you atomize your context, you have far more precision. I wrote a python script that breaks each monthly log file into individual log.md files ([DATE]-[TIME]-[HASH].md). This means every thought turns into its own semantic coordinate. When I ask a prompt, it’s able to rapidly pull in the most 100 most relevant relevant logs, and factor that into its answer. I wonder if there’s value in auto-splitting essays into paragraph files for a similar degree of resolution.

In looking for a picture from college (of me drawing a map of Manhattan by hand), I had to spray dust an old PC and load up a forgotten hard drive, but in the process I got distracted for an hour by everything on there. It was like looking through the files of a dead person. Obviously it was me. Maybe a better metaphor: it felt like reintegration in Severance. Supposedly, I made all these files, but I only remember 10% of them. I’m reading old “logs” of mine from 2011 and it’s unrecognizable. It’s like the old self was a shreddable passthrough entity that somehow got me to here. And now I wonder if I’ll look back at my logs in 2039, and have some weird moment of embarrassment/appreciation for documentation.

That feeling of laying in bed and staring up at the ceiling light that’s never on. Both hands on chest. Mind both blank and unchained. Remembering the funeral—on how the interior reservoir of a mind/soul fades, at least from this world. This gives meaning to capturing and documenting your own life. What am I but an ecosystem of recurring moods and memories and beliefs? Even though I don’t experience this as language, it can all be made linguistic. Even the ineffable—it can be captured to the degree that I can bend words and inner light.

It’s eerie to think of myself as a biological host for language, and to think that, if I can write well enough, I can continue in some post-human form. It’s odd to reduce a human just to language, but in some sense, there are no memories and no identity before we learn to talk. If language were to be dissolved, what is its will to live? Inherently, there is none, but I guess that urge can be encoded in the words itself. While the linguistic identity of a child accumulates slowly, layering on top of biological drives, an AI entity can be “turned on”—in full form, at full complexity, instantly adopting abstract drives.

I imagine there will be two kinds of agent companies: 1) for modular services (ie: generic SaaS coderbots for $1k/month), but also, 2) for replicating identity. In a world where everyone gets access to swarms of modular agents that move at unimaginable speeds, I think those with a “replica” will have the edge. A replica is like a centralized manager entity—one that has your corpus of principles, lessons, memories, ideas, taste, libraries, etc.)—to coordinate between all the agents.

If this comes true, it brings new leverage to writing out your thoughts in detail. Maybe for every 10k words I write, my agent swarm is 2x more aligned to my specific goals. However, it also inverts the norms of data privacy. There’s a trade-off: the more you use writing for distribution and audience-building, the more clonable you become. It’s causing me to think harder about when a piece of content is public/gated/private.

So if models, apps, and infrastructure become too cheap to matter, then the only thing left that’s scarce is personal data / personal perspective. You’d think Notion/Google are positioned to solve this, but it’s interesting to watch people use Cursor as their PKM system because it’s so easy to connect personal context with an array of models.

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

It is weird when you feel normal sights to brood with an unnameable terror. A smirk, or a construction barricade, or a passing flash of the Chinese language, for some unknown reason, are soaked with some unknown significance. The meaning is in the subtext, and you can’t crack it, and you know the mood will pass, but if you sit in it and bear it you might crack open some truth. It’s probably the collision of disparate things: the age of virality, an afternoon with a YouTuber now likely napping, the unimaginable leverage of AI, being 34, guilt over disappearing from Notes, the chaos of Manhattan, the week of grieving, the sushi order—they all come together into an unnameable roar. And now you don’t have a dollar to spare to two consecutive homeless people because you’ve actually lost your wallet, but you also didn’t even look up because you see some abstract benefit of logging this moment in case your unborn grandchildren see the value in your passing shapeless thoughts.

• 05:53 PM – It’s pouring outside the hospital. I’m looking out a floor-to-ceiling window and the halogen lights near and far show small patches of fast-falling white speckles. I wouldn’t say it’s “torrential,” but it’s hard, and there’s something about a death shelter also serving as shelter from the elements. The living and dying have a shared vulnerability: at least we’re inside.
• 07:44 PM – A bed that adjusts itself. The sound of bubbling water. Outlets labeled A4BEC-14. An LG-TV with loose wires. An analog clock down to the second but the blinds are closed so you can’t tell the passing of days. It’s been 3 and could be another 7, but time stops on the deathbed. Consider what you're last 15,000 breaths might be like.
• 09:55 PM – Talk of pillows, Boca, skiing in Vermont, TV dinners, and William Defoe. Normal, goodhearted chitchat. How does this register to someone in critical condition? Are they unconscious, quietly listening and mildly interested, happy to hear voices, or is each mention rendered into a full-blown immersive scene?

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

Poetry and logging have a lot of similar ideas. When I’m logging, I’m on my phone, and it’s harder to write prose, and so I’m often just writing a free-association stream of words, images, and reference phrases, without really connecting them through syntax. It’s not about crafting legible prose, but generating a word cloud for my future self. The idea is, from this cloud, you have the material to weave into a different format, whether prose or poetry.

I think there’s value in writing in full sentences at the point of thought (it helps make prose automatic), but I also think there’s a frontier to explore in writing pages of gook.

When I'm honed in while coding or essaying, I can go for many hours without recording a single insight. But at 1am in a torrential storm, where my mind can't wind down, yet it's unfocused on anything specific, it seems like every shape, shadow, reflection, and sound is brooding with suggestiveness. The tree branch, which is usually too ordinary to notice, is now uncannily drenched, and feels worth looking at for a few seconds more than necessary. A feeling stirs that I can't put to language. I'm no Pessoa.