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?

Having a baby reminds me of the infinite well of inner goofiness I have within me. There is an endless ensemble of voices and characters, songs and dances, that can be conjured in every moment if it keeps her smiling. This is the unselfconscious self coming through, because of course a baby can't judge. It's also not necessary a performance, for her, but it's your own expression that a child enables. A reminder that this could be the default state at all times if you have the courage to be labeled as truly and insanely weird.

The book Four Thousand Weeks references the average lifespan (76.71 years). This is also 27,999.15 days, which almost exactly lines up with the 1,000 day cycle. A life is 28,000 days. I’m currently starting my 13k cycle. This means by 14k, early 2028, I will be statistically midlife. It is a potentially grueling realization, but something about the 1k cycle makes it seem like NBD. 1,000 days is a long time, especially if you are chase epic things. It is effectively a whole life, a distinct identity. Of course, there is part of you that persists through each molting cycle, but it helps to see each as a rebirth. To think I have 15 more molts ahead of me is to realize I have 15 lives left, more than I know what to do with.

Starring out into a baseball field in late November, puddled and unkept, it struck me how, at one point in life, baseball was the whole frame of my existence: watching it, talking about it, playing it, traveling for it, dreaming about it, collecting cards, making Excel spreadsheets for those cards, memorizing the statistics of every starting player on every team, etc. Obviously, I’m nostalgic about it. That was just what I was into. I do wonder though, was that whole phase of my life a natural part of childhood that I was meant to get stuck in and grow out of? Or, was it mostly a big waste of time, spirit, and attention? I guess what I’m questioning is, is there a version of my childhood where baseball only took up 20% of my psyche instead of 100%, and would I be better off for it today? Would I be similarly nostalgic? Would a lesser obsession have freed up more bandwidth to develop in other areas? Or am I who I am today because of that obsession?

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?

Years ago I met a writer I admired at an event and it was a 45-second dud of an interaction. Recently I spent a few hours reading, understanding, writing to them, and it was warmly received.

I’ve been described as a slow-twitch thinker, and I think the same might be true for socializing. If I meet you at a party, and have a fuzzy sense about who you are and what you do, and I have to read your body language, and guess how to steer our conversation, the chances of it leading anywhere (unless we can find an uncanny amount of shared context in minutes) is low. But if you give me an hour or two to read your writing and really understand you, and then I write out a letter, or something like a mini-essay, specifically to you, the chances that we can connect are, I feel, virtually guaranteed.

The insight I’m fumbling towards here is that I enjoy and excel at slower forms of relationship building, and don’t need to feel guilty for not enjoying notes, or in-person networking events. Of course, I should still try both, but the real takeaway is that I should take seriously and systematize the practice of writing private essays dedicated towards specific people, for all sorts of reasons.

I’ve lived in New York my whole life, but I have nothing to say about it. Meaning, in Manhattan at least, I have no recommended pizza spots, no bagel stores, no upscale restauraunts. Almost every out of towner I meet seems to know the city better than me. I am willfully and unwillingly, an idiot in my own home. I stumbled in and just gawk at the mystery, still, every time. I mean of course I know some trivial facts (like how the skyline mirrors the bedrock), and I show them off when I can so my national and international friends don't get suspicious. 

Really, New York is a metropolis, a city of cities of cities. Austin is equivalent to Astoria, just one of several downtowns in Queens, one of five Burroughs. And so you’ll find whatever you need here, meaning, aside from the obvious places, you can surrender to the city and get swept into some odd and novel experience each time (alternatively, you can get caught in identical loops, only going to the same places). When I was in the psychedelic society I found myself in Gowanus, Brooklyn in the apartment of a 70-year philosopher with cancer as he took LSD and hallucinated St. Teresa Avila. When I was trying to start a virtual reality company, I was in Zillow’s headquarters putting headsets on executives, telling them we’d “put Manhattan in a briefcase.” When I needed money, I walked the same path every morning through Bryant Park, to the same corporate job. Now, as I start a family, I’m in a suburb at the edge, moving a little farther east every 3 years, and now I take the LIRR in to meet traveling writers. After many years, you realize New York isn’t one thing. Your take on New York is a reflection of yourself at that phase in life, and the city changes a lot less than you do.

When someone tells me New York is this particular thing or that, they're telling me who they are.

In SF I bought a book of letters from Neal Cassady written to Jack Kerouac. Cassady was the real-life companion to Kerouac on his road trips, the real-life Dean Moriarty. He is little known outside a certain circle, but a legend with it. Recently read an article that referred to him as a “sacrificial muse”; he enabled others to make their best works, but struggled to make anything meaningful himself.

Why might I be so inspired by him? In many ways, he’s a terrible role model, but I asked GPT-5, based on what it knew about me, why I might be inspired by him":

Assumptions: you’re attracted to catalytic energy, improvisational intelligence, and scene-making; you want wildness harnessed by form; you value unfiltered truth, high throughput, and culture-building more than polite careerism. Cassady is the archetype of kinetic mind-as-engine: he didn’t just write—he ignited rooms, cross-pollinated tribes, collapsed life and art into one continuous performance, and served as a human router connecting Beats → Acid Tests → Dead. You’re drawn to that throughput: the low-latency cognition, the riffing monologue that finds shape in motion, the willingness to live at the edge where new forms appear. As a builder of Essay Architecture, you also recognize the meta-lesson: Kerouac’s “spontaneous prose” needed Cassady’s voltage to spark but also needed editing, constraint, and a chassis—the exact dialectic you’re formalizing (flow vs. grid, spiral vs. structure). You like him as a role, not a role model: the driver, spark plug, transmitter; the person who turns a private idea into a public scene. And you’re repelled by his collateral damage (self-immolation, chaos, irresponsibility), which sharpens the prescription: steal the engine, not the wreck.

After reading more, by them and from them, I'm realizing that Kerouac and Cassady are moral failures and tragic stories, nothing to aspire to without extreme caution … I really ought to figure out what I ever saw in them, and see if it’s separable from their painful lives, or if they just inevitably come together … (I think this as I look at the inside of my right foot in my dark living room—almost midnight, still on SF time—and how the light from the kitchen illuminates 13 separate bulging veins and I simultaneously wonder if I’m fooling myself with this whole writing dream, and also, if I will die young from hypertension.)

Cassady’s mom died when he was young, his dad was a drunk, homeless hobo, so from 10 years old and on, he was alone and un-parented. He stole over 500 cars, and spent many years in prison. Apparently what others saw in him as enthusiastic energy, he later confessed was extreme anxiety.

Kerouac’s brother died young when he was 4. His father hated his writing, and he was tight with his mom but she was extremely Catholic and made him terribly guilty and resentful of her.

Ginsberg’s mom was a paranoid schizophrenic, in and out of psych wards, and often trying to kill herself.

They all had troubled childhoods, and that probably messed with their emotional regulation. They all seemed to dabble with mental breakdowns and suicide. There’s a letter Neal wrote where he kept drinking and had a gun to his head for 14 hours but couldn’t do it, and then his wife came home and he asked her to do it.

Their specific energy might have come from extreme psychic trauma. Worth thinking how to channel a genuine intensity of enthusiasm, without accidentally emulating their specific flavor (which you can’t fake because it’s rooted in pain).

What is a “beat in the suburbs”? ie: What is the distilled spirit of the Beat Generation without nomadic self-destruction and the romanticization of chaos? I say “in the suburbs” because that image is antithetical to “being On the Road,”; it helps clarify that what I see in the Beats is something different from the spirit of adventure.

Values to keep:

• authentic experience > social performance
• deep friendships > shallow acquaintances
• questioning conventions > agreeable
• singular destiny > societal cog
• madness in creative work > productivity
• spiritual focus > material focus

Differences:

• Stable home, stable family; but mindful travel
• Not about spontaneous output, but showing up regularly
• Editing isn’t antithetical; it actually aids future streams
• Consciousness expansion doesn’t have to be through drugs

I like this AI-summary:

“It’s Beat ideals with adult emotional regulation and an understanding that you can be countercultural without being self-destructive.”

My core value is contradiction, for there’s no other trait that leads to freer-thinking. If you are so stable in your beliefs, you run on auto-pilot. But if you are a Christian atheist, a Luddite technologist, a scrappy perfectionist, or any other kind of walking-paradox, a legless man, then you really have some explaining to do. In resolving the conditions between the two true but opposite things you harbor in one body, you think to make sense, and write to speak truth. This is where you find the work that matters. 

Why am I so inspired by the reckless and irresponsible Neal Cassady? It will take me years to find that out, if ever, but in that pursuit I invent some value system that is uniquely my own. This sort of embrace is, by the way, brand suicide. Your consumers are slow to update their mental model of you, and in the high-speed pizza counters of the Internet there is only small talk and one identity per person. To write for a niche, to stay on brand, to hit the same message, to do the things required for you to dominate the soul-gutting mediasphere is to mistake banal desperation for your alien soul. Do not trade oneiromancy for efficiency. Do not have one mind across all essays, let alone in one essay.

Re: to Veraeke's tweet … Purpose should come from virtues, not achievements. Don't have your self-worth contingent on realizing a specific hard thing. Rather, tie your self-worth in developing meta-traits that can be used towards any goal. This doesn't mean to NOT pursue ambitious goals, but it means to pay more attention to how your virtues can help you achieve it; and not the attainment of the thing. In fact, pursuing hard things generates the circumstances where you actually get to develop, test, and bolster your virtues.

I’m fascinated with the idea of being an “atheistic Christian.” It’s a paradox, and this stance makes you ideologically homeless. A Christian would likely say, “well if you don’t believe in God, and that Christ is His son, then you’re not Christian.” They will not accept you. An atheist who scoffs at God has no respect for esoteric ritual, talks of destiny, Christ worship, etc. and so they will deem you a loon.

Mainstream religions package everything together—theology, mysticism, history, ritual, etc.—and you have to subscribe to the whole ecosystem. In that way, Christianity is like Apple. I think a person is more engaged with religious ideas if they’re skeptical and free-thinking within each branch, while still operating within and respecting a traditional faith.

I’ve heard some people say “God is whatever you want it to be, it’s your relation to Him.” I don’t find that useful. I’d say that I’m actually more a theist than atheist, but theism comes with certain assumptions—God as an omnipotent, omniscient, benevolent “agent”—where as I’d say God is the entire arena and therefore not conscious, though still baked with intelligence.

My fuzzy notion: it’s not that God has a kingdom of heaven, but God is the kingdom of heaven, but also unfortunately, this kingdom isn’t some place your soul goes to; I think two things happen at death: (1) you lose your individuality and biologically merge back into the arena, fueling other evolutionary processes over millions of years, and (2) the monent of death is an experience of time dilation that, experientially, feels like a rather Christian afterlife, and also demands proper ethics in our waking life).