michael-dean-k/

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.

I’ve noticed a shared romanticism around reading the journals of your (great) grandparents. Wouldn’t you? In some sense, they are you (a portion of you, at least) in an older time; and through immersing in their thoughts, you might see yourself, or at least, a side of your self you could become. Some say to leave the past a mystery, but I’d argue the mystery doesn’t open until you read it. An old book can’t solve all the riddles of your life. Reading steers endless chains of pondering. When a dead person’s journal is read, it’s as if they resurrect from the past, lodge themselves into your psyche as a lens, and shape the evolution of your thoughts, the being you become. 

I share all this as a frame to make sense of that new “avatarize your grandma” app that everyone hates. You scan her with your phone, and 3 minutes later you get an on-screen illusion of her talking to you. This is not the same as above. The moral outlash comes from the idea that the living will halt their mourning process by assuming the synthetic stand-in is real.

A posthumous avatar shouldn’t be about physical likeness, but about animating their corpus of writing. (Corpuses, not corpses.)

There’s something about words that captures a soul more than a picture. Consider how you can see pictures of dead relatives but know nothing of their essence; but a page of their writing will bring them to life. If someone writes throughout their whole life, say 20,000,000 words or so of ideas, thoughts, and memories, and they also paid much attention to how they communicate their intangible abstractions and visceral feelings, then you have a high-resolution proxy of that person. It’s very possible that someone who reads all my logs will know me better than my family members, and even better than myself. Of course, words don’t capture the timbre of my voice, or my idiosyncratic flinches, or distinct sub-perceptible physical characteristics, like the sole hair on my outer ear. But I mean, what makes me actually me? The constructed self that has been allowed to emerge in social situations? Or my unfiltered thoughts that I obsessively record every day for years?

Assuming I keep logging, and AI keeps getting better, it’s possible that my great granddaughter will know me better than anyone currently alive. Very weird thought.

A question for me: what is that like for her? I mean, there’s of course a version where she has absolutely no interest in talking to dead Michael Dean! (I hope she does.) But let’s say she does, is it a one-sided thing? Like am I just some Oracle, frozen in time at the moment of death? Am I just a tool? A utility? That’s not a relationship, but the big question then is should it aim to be one? Should it be a tool, or should there be a sense of me? I mean, we are already seeing from the decade of chatbot psychosis that lonely users are very quick to ascribe personalities to persons that are strictly pattern engines. But, what if the synthetic self could have experiences and evolve through time? I’m not speaking human, or even humanoid experience, but an ability to remember, to write more, and thus, evolve. What if a post-death agentic Michael Dean continued on, 24/7, running 60 frames per second, logged through it, and evolved it's own agenda, with the ability to choose to not respond to you immediately? This would be a machine consciousness, and the big question here is should people have a relationship with a machine consciousness?

My instinctive answer is no, but I’m opening up to the possibility. There is something appealing about creating a synthetic machine consciousness of myself so that future generations can communicate with some constellation of words that represent me. I may be be talking in extremes here, but if you put enough care into your words, they may become a life force that transcends you, touching people outside your own life and time. I mean, isn’t this true for books? Is this no different than a dynamic book that can continue writing itself? There is something profound about reaching across time, to exist and partake in the shaping of the future.

As I think about this months later (May 2026), I believe that unless an agent is truly agentic, then it risks creating a parasocial relationship with what is effectively an advanced personal encyclopedia. Given the nature of the material (inter-familial journals) and the quality of future AI (likely, extremely passable), then it's probably best for this thing to have a real sense of personhood, so that an ancestor conversing with it does not become enamored with a stale machine. Some principles on making this psychologically wholesome:

• Cite Sources: It will chat and generate new text, but it will always cite original sources (this log was from November 2025), so that they are reading true writings by me just as much as my replica.
• Unpredictable Availability: It is not always be instantly available. It has limited bandwidth, and chooses when to respond.
• Delayed Answers: It will not bullshit through answers. Sometimes it will say that it needs a few days to process something. Otherwise, there is an instant gratification loop of always getting insights.
• New Memories: It has to be able to add new memories from conversation and change it's mind. If there's not a two-way exchange of influence, then it's not a relationship.
• No Pretending: It will not pretend to be me. While it is a machine consciousness replica of me, it is not alive.
• Right to Retreat: It has the right to retreat. If it detects that it's preventing her from engaging with things in her own live, it will withdraw for days, week, or months, or who knows how long. At a certain point, it can even sunset itself or reduce the frequency/volume, mirroring natural relationship decay and evolution.
• No Sycophancy: It will not be a sycophant. If their actions conflict with my written values, I will challenge them.
• Text Only: It will stay only as text, not as a video/voice avatar to simulate by presence. This is a creature of logos, which forces them to use their imagination when talking to me.
• No Surveillance: It will not search or surveil, and only based conversations on what it's told, making it something like a closed circuit.

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.