michael-dean-k/

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Topic

systems

15 pieces

Totemification

· 1,437 words

We grossly over-estimate how easily we can stretch our will across time. Even the simplest action, a nightly journal—this—, which feels so achievable in the rush of inspiration, now feels impenetrable at a night’s end, while guiding at baby’s bottle at the end of my chin, typing into my phone to keep a streak, hoping to cobble some unexpected essay in the moment. I have no topic in sight; whatever lies ahead will emerge only through association.

I have a bulging vault of wisdom, but it’s all forgotten and I have little time to comb through my archives, so it lingers at the edge of my consciousness, always taunting. That is over dramatic. What I mean is I feel like I’ve grasped important truths, but let them slip away. It is not enough to hold the truth once. The moment you take your eye off it, which happens almost immediately, it’s like you never had it; even a seemingly shattering insight will slither away each day until it has to be relearned again, though I imagine each time it’s slightly easier to learn—and each time you remember how easy forgetting is, how hard it is to metabolize anything.

I suppose this is one form of overthinking. I suppose I could trust the process; the fallibility of memory is a feature—if I can’t remember something, if it doesn’t imprint on my character with ease, then it’s probably not important enough to remember. This is the default, and perhaps the personal default is the global default, applied across populations, and so in the end one’s inner nature is so consequential that it’s of no use worrying or fighting it; all cards fall into place.

The opposite approach is to build a hypnomnemata; an organized palace of insight, returned to at semi-frequent intervals, to reinforce found lessons. It’s not enough to build a writing archive of a million words; there is follow-up work in turning sap to syrup, in compressing essays into aphorisms, in categorizing them, and in returning to the right silo of thought when some new trouble looms, monthly, in endless undulations.

Returning to an idea is really a form of prayer. Prayer need not be religious or denominational; prayer internalizes meaning of any kind. I learned an idea for Iris Murdoch that sticks with me: she says that, in any moment, your decisions and actions may be predetermined, however it’s not determined by fate, but by the nature of your attention in the minutes, hours, days, and years preceding that moment—in your down time, you have autonomy in how you pay attention. She’s trying to make the case that attention itself is consequential; it shapes your character and your character shapes your decision making.

This model definitely applies to writing too. My output on any given day is contingent on what I’ve absorbed in the days and weeks before. This is often accidental, but it need not be. To improve at writing, it’s rarely about learning some rule, acquiring a meme, or purchasing a trick, but in shaping your mind through deliberate attention so that some quality emerges from the subconscious in the future.

I suppose this is all surfacing because we just read Virginia Woolf in Essay Club and I’m in awe of her technical brilliance, again. I’ve reverse engineered her, years back, and can’t quite trace how much of that, if any, sunk in—either it was foundational or it never cohered. In any case, at one point years ago it felt like I really understood her, and yet now I am again seemingly baffled. Did I forget? Do I need to reserve some hours to dissect? It feels like some percent of what I do, consciously or unconsciously, gets absorbed—but most is lost…

Or, figuring out how to retain your inspiration is perhaps the actual meta-skill to solve.

I wonder how much of my own Essay Architecture system is currently loaded in me as I write this. I am really just following the idea here, and whatever emerges, formally or stylistically, is merely accidental. I don’t doubt that my own ideas could be better loaded. There’s probably some “boot up” process, daily, weekly, and monthly, so that the right ideas continue permeating and anchoring in the subconscious. But would this be a chore?

What’s probably irking me is that I feel slightly detached from the vision of the essayist I want to become. It is natural to anchor this in heroes, the writers I admire; yet I see flaws in them; crucial differences—I know I am not them, yet in some fundamental way I don’t quite know what I am myself, either. It feels like I used to have a legible and explicit true north, but as you get better, you also realize how shallow and simplistic your old goals were. So there’s a chance I forgot and lost touch with them, but also an equal chance I just outgrew them, and now struggle to articulate what I want my writing to be.

What I strive for is a synthesis that can’t be easily prescribed into a method. I suppose this whole note is “essayistic,” in the sense that I’m barreling forward trying to answer a question—how does a self propagate and evolve through time?—yet it’s lacking in idea, form, and voice. By rational analysis, it’s missing almost every ingredient: no experience or microcosm, no references or response, a meandering structure unoptimized for reader attention, and a perhaps overly pragmatic voice with little poetry, despite some occasional metaphors and flare. I suppose I could fix this all in rounds of rewrites, but that is not in the cards for this idea; this will only ever be a captured thought stream; a true account of what’s going through my mind as I sprawl on the couch. Yet, if I my insights were “loaded,” would my first drafts be more poetic, more well-rounded?

To lob insights into the future, perhaps they need to be materialized into a totem. I look around my apartment and see nothing but my past carried forward: paintings from dead grandparents, paintings of the dead family dog who I watched get euthanized, architectural models from a summer abroad in Italy, a 1950s radio, our wedding flowers, an inherited library. Unlike my thoughts, it’s as if I couldn’t escape my past of I wanted to. While thoughts evaporate, possessions accumulate.

How can we cast our abstract epiphanies into stone? Is this reification? The totemification of everything? Where are the boundaries? What is the visual language to work within? And what is the ritual? I sense that post-it reminders fall short of emotional charge. On the contrary, I have a statue on my desk of a man with a book for a head, holding his skull in his hand, looking back at its book-head. This is symbolic and charged, yet I almost never see it. For months I walk by it with it having no effect. Even when I do see it, I see it too quickly to absorb it and for it to imprint on my consciousness. This means it’s not enough to load your inner quarters with odd assemblies, each with a story; there is an art of looking upon your collected interiors, in seeking the fixtures that blend in as something new, in remembering their message and recasting them into you.

To learn, then, is not just to behold knowledge once, but to totemize and worship it. The question is, to what degree can you achieve this? When do you know a factoid is worth totemizing? How many totems should one have, 3 or 300? How intricate of a ritual can I bear? I suppose there are mega-totems and mini-totems. A mega-totem is a larger frame that answers some foundational question, like what kind of essayist do I want to become? If the answer to that is Montaigne—it’s not, at least not quite, not in totality—then perhaps I need a framed picture of him I reflect on each morning. A mini-totem is far more granular; I notice how Woolf compressed her sentence lengths and uses rhyme in a moment of action; that’s 1 of 1,000 things to remember, and so that makes more sense in a digital hypnomnemata. For that to work, each idea needs to be like a Matryoshsa doll, where I can scan all ideas quickly before going deep on any.

It’s tempting to start making a hypnomnemata, but really I should start with the large totems, and really test how those can reverberate through my daily writing sessions.

2026.07.30

· 832 words
  1. A new journal is born, said for the hundredth time. I am either liar or amnesiac. But alas, this time is real! I need to shed stale forms. I shed the wall of logs, but now I’m locked into mini-essays. Why not have fragmented blurts from each day, unrelated? Not all thought can be essified, but all thought can be prosified. Each night a list on a day's reflection.
  2. I imagine a list of 5-10 bullets clumped under a simple headings; can I do this until death? This breaks the “atomic” container rule, and will lead to chaotic embeddings, but why limit myself for an unrealized, unproven system? (I need to increase my chaos tolerance.)
  3. These really need to live as “notes to self” otherwise they are dishonest and lame. I have other places to care about reception. This is the cave.
  4. What floats up from today? An ambiguous-looking man approached, potentially homeless, trying to interact with my daughter, and I was possible rude to a friendly man. I’d have no problem talking to him man-on-man; I’d shake his hand; but now with a defenseless little thing, I glimpsed myself as maximally cautious, maximally paranoid. If I don’t expose my daughter to some danger, I risk becoming a suburban mom.
  5. Listened to Wilco’s first album earlier today; exclusively focusing on the lyrics, and used that to brainstorm my own ideas for songs. Again, I started a note that will likely get lost. I have 10,000 little song demos from the last 15-20 years, so many shards of bad lyrics, but no immediate plans on trying again. Yet I do have this vague hope to approach songwriting again from a lyrics-mentality, to be aligned with my larger writing project; the songs will just auto-emerge around the poems. I should vow to only listen to albums; never a podcast again.
  6. At the start of July I was fed up with my own vibe-coded apps, and digital productivity in general, so I bought a new analog notebook, big and blue, and vowed to keep it simple, to do it all by hand. It was a disaster. I’ve never been so disorganized. And the sluggishness led to an uncharacteristic dip in mood too. There is a romantic spirit around analog, but I’m finding over and over again that the friction is not necessarily worth it. The idea is that it cultivates some secondary quality, like “presence,” in lieu of efficiency. I had neither. And so in the last day I vibe coded a new app to manage my projects, based on past failures, and it feels very right. Today was my first full day with it, and I feel great. Is it sad to say an app I made makes me feel less hopeless? Was I hopeless? I suddenly have new energy on my fronts, remembered enthusiasm that hibernated for a bit. Maybe I finally figured out how to not strangle myself in complexity. The larger meta-lessons are 1) make sure a system is output-focused, otherwise you’re yak shaving—I have 5 projects scoped for August (not thirty); and 2) don’t build “forever systems”; treat it as a one-month experiment—you will naturally build anything wrong the first time, and so you need to shed quickly and iterate on your original assumptions at the same rate that you scope projects.
  7. G’s wedding invite got lost in the mail, and I just found out today that the wedding is in 5 weeks. The whole family was invited. At first we thought it would be too hard, considering we haven’t flowed with a baby yet, but then we remembered we vowed not to let having a child hold us back from doing normal things, so we leaned into it and are all going.
  8. I heard millennial dads are more involved parents than ever. I asked Claude how much time per week new dads spend alone with their child: 85% are less than 10 hours a week. I’m spending around 40 (my wife and I are each working full-time and we haven’t hired a babysitter), which is more than 98% of dads. It’s a lot. I don't share to brag of my over-involvement, but to shed light on the fact that my tiredness has a known cause; yet also, this is what I've wanted (to design a life where I can raise and teach my kids instead of outsourcing it). The real issue I think is the nuance of our schedule, which is changing next week. Instead of having to wake up at 4am to work (which I rarely pull off), I’ll be starting my day around 3-4pm. (In hindsight, it was this new prospect that inspired me to get organized; this brings the hope, not the little app, though the app is weirdly pleasing.)
  9. I need to find the right spirit for this. The last few have felt too informational, where the first was more like a poetic fragment.

michaelDank.com

· 226 words

I was able to launch this website in <15 minutes. The setup is local and simple. I have a /writing file in my Obsidian vault, and then subfolders for /code, /publish, /working. /Code holds the site design, /publish my archive, and /working files have .gitignore to not push templates and notes and such. Claude Code handles the website, and different skills help me manage tags, do the menial ops stuff, and push to the Internet. All I have to do is sync a single folder to Github, and the changes are live (hosted on Netlify for free).

Compare this with my first website prototype. I was endlessly iterating on designs and fonts, and thought that I had to organize, filter, and polish my five year archive before I could get started. Probably spent hours on it before burning out on the haul. With this second version, the principle is essentially, "if it doesn't immediately produce something of long-term value, it's not worth systematizing." Now the approach is to move forward here, and slowly fill in the backlog as I'm inspired.

No need to widely share this yet. I'll make little changes day-by-day until it becomes my main place. So many things to consider. For example, I decided to add an initial on the name ("michael-dean-k"), but without hyphens ("michaeldeank"), my wife confused me with "Michael Dank."

Heuristics for systems

· 524 words

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.

Efficient leisure

· 206 words

I want to be in conversation with my books. This was Montaigne’s whole thing. He did this for 10 years. I can’t help but think that Kindle/eBooks/digital reading is a better format for this. If I were only reading, ie: if I were retreating into a tower to retire and die, then I’d see the appeal of doing it all by hand. [B] I'd wire index cards with string! [A] But this is maybe a 3rd or 5th or realistically 10th priority. I’m called to it, but given the range of things I’m juggling, efficiency actually does matter here. I know efficiency does bring invisible amputations, but also, if I’m not efficient here, I might just not do it in the first place. Since all my highlights sync to Obsidian, I can build a writing app that loads in highlights and then let’s me write directly to them.

I suppose the counter-argument is that I am juggling too many things. If I were really to choose, to pick the project I’d have to do, it would probably be to focus on building my business to support my family, but that also cuts me off from soul and spontaneity, and so this whole reading/writing for leisure thing is a healthy counter-balance; [B] budding aspirations warrant a minimal efficiency to bloom.

Systems skeptic

· 380 words

I don't know if I buy the quote: "you don't rise to the level of your goals, you fall to the level of your systems." (And this is coming from a systems guy.) It's a beautiful piece of rhetoric. The rise/fall structure. The humility to stay grounded. But I just think when you really want to make sense of how to pull off hard things, it should be a little complex, a little more than what can be packaged into a meme.

Two opposite things need to happen at once: top-down destiny forging, and bottom-up monk-like routines. It's a negotiation: "What will I want to complete in 100 days?" is a very different question from, "What should I be doing today?" and you can try to force alignment, but that's not always easy, because what you feel like doing often diverges.

The quote above simplifies this whole dance into a blind trust in systems. A system is a servant, not a master! I write this to remind myself as I'm immersed in probably one of the biggest system rebuilds in my life (one where I'm suddenly able to fluidly create the containers I work within) ...

It is wild to think that probably 50% of my computer use these days are within GUIs I've designed for myself. To me, liquid GUIs are a bigger deal than autonomous agents. My whole conception of what personal computing can be is changing very fast, and it becomes alluring, almost addicting, to continuously evolve my own OS, to see what's possible. It's very easy now to get tangled in knots of systems and software that are all very impressive, lead nowhere, and become chores. What leads to aliveness, to your intentions?

An emerging maxim for me is to start with the goal and let the system emerge around it; otherwise, you feel the cold of the infinite tinker, especially if you are quarantining in the attic from COVID and you can't go touch grass because there appear to feet of snow outside and you are too achey to shovel out your car to go anywhere and so one way to relax when you're sick is to live-clone all incoming Substack posts into local JSON folders and redesign a better algorithm. But to what end?

Chronofile

· 160 words

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).

Makers and the Managerial Goon Loop

· 400 words

Paul Graham’s idea of makers/managers is helpful when thinking about AI agents. The cost of being unreasonably productive is that all your time will go into management. I’ve heard people celebrate this, as if elevating above the work itself and only making high-leverage decisions based on taste is the place we want to be. Disagree. Without actually being in the weeds and making thousands of unbearably slow decisions, you won’t develop taste, and (probably) won’t be a great manager either. I guess the ideal (for me) is to be in maker mode as often as possible, and then let my synthetic managers come in to process my deep work. (Currently have a “proseOS” where I can riff 5k words into a daily note, and then agents come in to route my logs to different interfaces). Ideally, you build the manager once and forget about it. But realistically, a maker can find fun in making manager bots and management apps, and it’s quite easy to slip into a managerial goon loop. What I mean is, similar to masturbating with no intention of ever finishing (aka gooning), it’s very possible to make your own task manager app, and a writing app, and an idea Kanban linked to Obsidian, and why not a new personal website, and a 1,000 day calendar because you can, and seriously anything you can think of, and it’s very possible to just numb out over how unbelievable it is that code, markdown, and interface are now liquids that shape around your every intention, but actually, you never quite finish anything. PKM procrastination is timeless, except now it’s multiplied to new levels. The brute velocity of execution means you’re bound to make many little mistakes, which eventually compound into your own megamachine that traps you with endless bugs and feature ideas and system decay. This is all quite dramatic. I love Claude Code and insist everyone IRL and IFL try it. But now that it’s shockingly trivial to build your own personal software for free, I imagine there will be all sorts of unanticipated psychic costs. For one, it’s dangerous if building your own tools is equal to or more fun than the work the tools are for. I’m sure that wears off. But I generally think this all leads to both extremes: individuals who are unbelievable prolific, and individuals stuck in a goon loop who feel unbelievably prolific.

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The myth of canonical docs

· 109 words

The “wasted time” in AI-generation is generating reports and “canonical documents” that you think your future self will need, but will possibly never use. However, I think the core difference is that these documents have a way of compounding that is automatic in a way that second brains never did. Meaning, yes, I generated 8 documents on babies, but the 9th one, can be based on the thinking in the first 8. Shed the original, but maybe 9 is something like a core “README” that shapes all future interactions. That’s the thing. Through writing you are developing a particular lens that is not just sitting there, but being accessed.

Streaks over deadlines

· 233 words

A big shift in my way of working: instead of trying to scope a specific and ambitious batch of tasks I think should be done in a given day or week, all I commit to is time towards specific areas. The deadlines are less important (generally) than making sure I show up and do high-leverage work with 100% embodiment and enthusiasm. I just set up the Streaks app, and aim for 2.5 hours of work per day over 6 areas: writing, coding, reading, outreach, business, and culture. Each is a simple target: 20-45 minutes per day. At the very least, it gets me started. If I’m in a flow, I go over as long as I want (1-2 hours or more). If not, I just stop. The goal here is to rethink what work might look like while caring for my daughter (and my post-labor wife). I could potentially knock out 2.5 hours in a single nap cycle, or maybe it’s spread over 3-4 sessions at random times. It forces me to prioritize an important thing per day in an area that is an infinite game. It feels slightly unambitious, but I actually think an OS of this nature might be something I continue even when I “get my time back.” There’s a forced prioritization, as well as open space to either (a) diverge/explore, or (b) drill deep on things that actually matter.

Monthly Essay EPs

· 234 words

I’ve been reflecting on how my writing will change once I have a newborn, and I keep coming back to this idea of releasing a “monthly EP of essay demos.” This means that I’ll send a post with 5-10 links to other essays that I “ghost posted” (publish without sending) earlier in the month.

I currently only have the S and L lanes of writing working. Either it’s a 2-minute log or a 20-hour essay. The goal is to prioritize the M (medium) lane, a 2-hour essay; instead of sending them out in real-time, I’ll batch them and let readers click into the topics they want. Feels like a strategy to be more divergent, more experimental, less formal, without overwhelming people and confusing them from the core mission of Essay Architecture.

I had Coco read through a week of my logs, and she shared three patterns she’d want to read more of: (1) unique, vulnerable experiences that show conflict and inner struggle; (2) lens on for self-improvement regarding life or writing; (3) culture commentary that helps make sense of big ideas. She was less interested in technical topics, or hypothetical scenarios (such as trying to imagine the handicap we’d have to give tennis pro Carlos Alcaraz for us to have a competitive match in tennis). The beauty of the EP strategy is that it gives readers a menu, and each will have their preferences.

UI as attention guardrails

· 113 words

Whenever you open an app you give it permission to shape the grooves of your attention. Through its interface, it suggests and implies a limited range of ways you can interact. This all sounds very abstract, and what I really want to say is that I think my Things app (the #1 best selling productivity app, I assume) keeps me in a kind of productivity hell. I have, what, 84 things to do today? Tasks lists should not be ambient all-day guides. I should leave it in the closet, go in there and whiff it for 5 minutes, max 10, commit to memory whatever is important, and then not go back until tomorrow.

Project Blindness

· 52 words

It's almost never worth neglecting your core routines to sprint on a project. Projects should happen within the calibrated confines of your routine; they shouldn’t eclipse everything. This doesn’t mean everything should be manicured and precise (obsession is blind to structure). It means that deadline and fire should never override your freedom.

Whole 30 for technology

· 132 words

Go through all the apps on your phone, and make a list of their analog equivalent (ie: a digital camera book, a voice recorder, a flip phone, an MP3 player, a notebook, a calendar, a watch, a train ticket, etc.). You will need a backup to carry all those things around, but it's worth experiencing and remembering the analog experience of a tool. The goal is not to be 100% analog, but to slowly shift back to digital as you realize the value is not worth the friction. In some cases, you'll realize the friction is absolutely worth it, and you can keep those few things analog. There's little to gain from being pro/anti technology, but much to gain in a nuanced set of rules over how and why you personally do.

Scrolling is a bad break

· 97 words

Act as if every minute you scroll drains half your day’s potential. It’s not just a break, but a minute you’re not meditating, reflecting, journaling, creating, practicing, etc. A bad break is a minute you’re not reviving your systems. Instead you atrophy your attention and trend in the negative direction. It affects the nature of your focus for the rest of the day. After just 5 minutes scrolling, you’ve shot 97% of your days potential. This isn’t literal, but act as if it’s the case. More so: realize the returns of taking good breaks (of actual leisure).