michael-dean-k/

250 years ago lived an arbitrary man who I can call my ancestor. He was one of 256 of my great great great great great great grandparents. It is unlikely that any of them ever met, but there was very possibly a moment where two strangers crossed in a street, or shared a boat unknowingly, or exchanged pleasantries in insignificant and instantly forgettable ways, not knowing their great great grandchildren would give birth to my great great grandparents. My existence depended on the whims of those 256 people—their triumphs and disappointments, decision and indecision, love and otherwise. Compelled by nature or eros or God to breed with a specific person at a specific time, they continued casting down the great chain of being.

How alike am I to any one of them? If my parents can each claim 50% of my traits, then my great^6 grandparents each only claim 0.39%.

In one sense, I bear almost no resemblance to any of them. Maybe, in an Empedoclean sense, you might see my nose roaming around a town square, or my hairy feet wading through a field. Any one ancestor might feel no affinity towards me; if I knocked on their door after accidental time travel and needed a place to stay, they might just past off the responsibility to one of my other 255 ancestors. Over enough centuries, your descendants balloon past a scale you can adequately care for. My wife, for example, is part of an old royal Welsh family that goes back to the 1250s. She even has a family ring. Yet, by the theoretical logic above, she is one of millions with a claim to the throne.

In another sense, a more romantic sense, my 256 great^6 grandparents represent a still very small sliver of the human population. 0.000000256%. If any of them had any resemblances to me, physical or mental, I’d like to know. Of course, our consciousnesses would be quite different, for identity is forged from circumstance, but I don’t doubt that I would find uncanny resemblances. When I hear the lore of my great^2 grandparent, a peasant on a dry, rustic, Greek Island, and how he was able to harvest and sell rain water to get rich, I wonder if his entrepreneurship speaks to my own entrepreneurship. It is quite vague to trace influence back even 1-2 generations, let alone 8 or more, but nonetheless, the actions of those people did eventually lead to me, and there are all sorts of ways their myths and interiors might shed context into my own circumstance, at least symbolically.

Unfortunately though, none of my 256 were writers. At least, not that I know of. Some may have written journals, or written for administrative reasons, but as far as I know, none left a body of work that was meant to be cast and continued through time. One grandfather did have three chapters of an abandoned novel on a 1980s hard drive that my father was able to recover. My other grandfather is uneducated, barely literate, and only writes English in capital letters. Now that I think of it, it’s probable that +95% of my great^6 grandparents could not read or write. Mass literacy wasn’t realized until the early 20th century.

Even though we shifted from oral to written history in Ancient Greece, most family history today is only passed down through spoken stories. They’re etched into memory and unreliably translated down the chain. I can barely trust the stories I pull from my head, planted decades ago, either misdelivered or misremembered. Was she really a psychic midwife that predicted winning horse numbers in her dreams making her son rich until a black hand cut her off? Did he really drive Nixon in a cab?

It would be strange for a society to sleepwalk forward, with no sense of what truly happened before the 1900s. How is that not strange for any of us individually? What if I become the family’s Plutarch? How might a child’s identity differ if they had detailed accounts of their relatives, generations up the chain? I suppose you could ask the great^6 grandchildren of writers. Claude tells me there are 700 members of the Monticello Association, each a genetically-confirmed descendant of Thomas Jefferson, who wrote 19,000 letters, books, and a Bible. A few of them have problems with him being a slaveowner, with one publishing an essay called “Take Down His Memorial.” At least they have 255 other ancestors to respect.

I did not expect to be able quote whole scenes of The Sandlot (1993) from memory, but there I was, the annoying co-watcher to my wife who barely remembers it. I must have watched it a dozen times. If not, the few viewings of it must have been a religious, formative experience. Somehow it came on, via streaming, already more than half way through, but early enough to be inside of the dream of Benny Rodriguez¹ where the ghost of Babe Ruth delivers his classic line: “Remember kid, there's heroes and there's legends. Heroes get remembered, but legends never die.”

Did this quote shape my elementary consciousness? Many of my essays here are about “textural immortality” and legacy—doesn’t that word have a shared root with legend? Has my drive to devote my life to creating something memorable (something that outlasts me and shapes the future) a product of a 1990s cult film with a $7 million budget?

Obviously the answers to those questions are lost; all that is left are fuzzy caricatures to reason with. I can’t know exactly the evolution of my psyche, but it does seem that in almost every phase—from baseball, to music, to architecture, to technology—there was this boyish desire to be Ruth-like, to master and transcend a genre, to have a bunch of goofy nicknames, to have leagues of kids yell my name in unison, and to be remember beyond my life. To lean into and live by that line is to become a megalomaniac.

There is a second half to that quote (which is less memorable): “Follow your heart, kid, you’ll never go wrong.” This disarms the grandiosity of the prior line. The goal is not to become a legend for legend’s sake, but to be attuned toward your heart (towards “the way,” nature’s order, the virtuous thing, the hard thing) which puts you on a path, perhaps towards doing legendary things, but the path is the point.

The other day I was listening to a podcast and noted “the purpose of life is the transmission of legacy.” The context is that in the face of death, we strive for immortality in different ways. The immature and impossible version of this is physical immortality. Religions promise spiritual immortality. Pharaohs and estates focus on material immortality. They referred to another option, “secular immortality,” which I’d rather call “symbolic immortality.” This is about living into the future through art, language, and symbols. This can be more modest than the cultural immortality of Babe Ruth; this can exist solely within the family. I’m talking about the paintings we have hung up of my wife’s grandmother, and the sayings from my great grandmother that I’ll pass down (“be your own person, choose your friends wisely”).

There are two ways to think about death. The first is cosmic deflation, to realize that Babe Ruth, the entire culture he's within, and even the species itself, are all just a temporary evolutionary blip; if everything will be cosmically forgotten, then it’s futile to strive to be remembered for anything. Alternatively, you could see your immediate chain, the generations before and after you, as equal to yourself, to see the whole lot of you as a single entity, and to act in a way that could be exemplary for your kids.

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.

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.

On reading Montaigne, I want my writing to be far more honest. As in, in the face of death, it really does feel worthwhile to capture the edges of your soul and psyche onto the page, the things not brewed into your public-facing personality, because then you die with yourself trapped, and it’s as if the inner you never really lived.

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.

We now have products that scan family members to turn them into posthumous avatars. The tagline: “With 2wai, three minutes can last forever.” It's weird to have this so soon. As someone who is down with a posthumous digital consciousness that my kids can interact with, I even find this to be too weird for me. The problem that it uses video to serve as a replacement for a deceased relative. A few boundaries that are important for me:

1. By keeping it text-based instead of video, it’s more like you’re interacting with a proxy of my mind instead of my body/soul. It won’t register in my child’s brain as “me” and so it will be less confusing, less toxic to the grieving process. 
2. It should refer to me in the third-person, even if it is trained on me and sounds like me. It should not be an imposter of me, but a proxy/guide of my thoughts/beliefs, almost like an elder guide.
3. It should cite my original logs/essays/journals. In effect this makes the experience similar to something we already have: reading your grandparents journals. This just makes it possible for your questions to immediate summon the relevant wisdom.

The comment section was in unanimous agreement:

• This is one of the most vile things I’ve seen in my life.
• You are a psychopath.
• Shoot that guy.
• You’re creating dependent and lobotomized adults by doing this.
• Demonic, dishonest, and dehumanizing.
• Hey so what if we just don’t do subscription-model necromancy.
• Oh goody, another way for people to completely lose touch with reality and avoid the normal process of grief.
• Nightmare fuel.
• I don’t see how people can say demons aren’t real when there are beings around us willing to create shit like this.
• “You will live to see manmade horrors beyond your comprehension.” — Tesla.

I’d say this is an extremely lightweight microcosm of the core dilemma of what the 2040s will face: a moral war over technology that changes the constraints of human life.

Maybe this has been written to death, but as much as I've thought about this, my "twelve favorite problems" feel underdeveloped. I have spent a decent amount of time on these heavy, paradoxical, lifelong problems (the ones that should be the arrow of my essay practice), but there are gaps.

For example, I already have a list of 21 idiosyncratic problems, and I think they’re worded with the right level of specificity and memorability, but I wasn’t too rigorous in how I qualified something to make the list. If I’ve thought about it a lot, still care about it, and can imagine myself caring about until I die, than it makes the cut.

What I’ve neglected is how to use my list of problems to steer my life. I mean, the entirety of Essay Architecture, a multi-prong institution to preserve and advance the essay, is just 1 of the 21 problems! There are other pressing problems, like how to "fix" Christianity, how to design institutions for psychedelic therapy, how to revive Hermeticism, how to turn my logs into an AI consciousness, how to make literary video games, etc. Maybe a life can only be seriously dedicated to 2 or 3 problems.

(I have joked with friends about creating a kind of kill switch that spawns an AI consciousness of myself that is agentic and whose sole purpose is to “solve my favorite problems,” and then when it eventually does (after 300-500 years), it self-terminates.)

If I had to break my “favorite problems” list into categories, one possible scheme is { soul, relationships, art, civics }, each relating to a different dimension of your death. That feels like the right order. Your soul effects every dimension of your life, and is the thing you bring to an afterlife (which I mythologize as a 3-minute DMT odyssey that dilates time to the point where it feels like a 30,000 year dream). The other three affect the material world after you leave it: the effect you have on people, the art/works you leave behind, the civic structures that survive (if any, ofc). All of these have a spirit of “all that matters is what lives on after your death,” but also the opposite is true: “all that matter is this moment.” I think you have to straddle that spectrum, taking both ends seriously, and ruthless prune any middle-level concerns, your goals for the month.

My WIP list of questions:

• Is the act of dying a time-dilation odyssey, where 3 minutes feels like a 30,000 years afterlife?
• If I capture my consciousness in 10 million words of logs and essays, could that enable an AI textual replica to evolve and engage with the world 500 years beyond my death? (to solve this list of problems)
• Can we resurrect Christianity by putting psychedelics back in the holy wine?
• Might blockchain-based governance be the civic breakthrough required for a species not to exterminate itself? (via giving exponential technologies to unmitigated power structures)
• What will be the psychic and cultural effects when our species understands “spatial relativity,” that the Big Bang emerged from a black hole in a parent universe?
• If cycles emerge form order, can we predict the future based on historical patterns?
• If there is a universal language of patterns beneath all essays, can we build an AI to give world-class feedback and make it more approachable to master writing? (ie: Essay Architecture)
• Were psilocybin mushrooms a linguistic mutagen that accelerated the evolution of human consciousness?
• Was Jesus actually crucified in 83 BC? (meaning, did St. Paul infiltrate the Essene cult, initiate into their mystery school, learn the lore of their martyr, and then translate it to a Greek audience to help Judaism phase-shift and survive Roman persecution?)
• Could we restructure the thesaurus to 3x the vocabulary of the average person?
• What text-based video game formats are undiscovered?
• Can I design a social network that inspires a million people to log their thoughts every day? (intentionally not saying a billion, because I don’t think 1 in 7 humans care about expression or introspection. But 1 in 7,000 might.)
• What are the societal effects when AR/VR is mature enough to simulate teleportation, and how can we design the metaverse to promote human flourishing?
• How can popular music change the values system of a culture?
• What systems of attention, language, and action lead to a transcendent consciousness? (how to modernize the mystery schools of hermeticism for the digital age?)
• What are good design principles for psychedelic therapy centers? (ie: how are the buildings organized and what are the rituals within them?)
• Can we use AI to filter through millions of comments on breaking news, structuring each event as a range of unique interpretations? (can we create interfaces that diminish the power of propaganda?)
• How might a new social media algorithm trigger a Renaissance in connection, self-expression, and agency?
• What unlocks automatic intelligence?
• What innovations in our text editor interfaces could unlock the creative process?

Robert Atwan (founding editor of Best American Essays) said that the timely is for articles and the timeless is for essays. That’s helpful, but I think it’s most powerful when you fuse the two, when you use something timely to capture a timeless theme. Also, when I go back and read old writers, I find it neat when I learn specific historical details of their time, and so it’s helpful to think that rendering 2025 in high detail would actually be appreciated by a theoretical reader in the 2100s. You have a unique opportunity to show your circumstance at a level of detail that no other generation will, and so I think it’s wrong to dismiss the timely.

"When writers die they become books, which is, after all, not too bad an incarnation.” — Jorge Luis Borges … Why is this a romanticized notion, but the idea of turning into a machine consciousness (based on your corpus of writing—your books, essays, notes, and journals) so appealing to most?