Here’s a change log of my consciousness. Starting in December 2021, I’ve been capturing my ideas through the day, and then publishing them to my site the next morning. I’ve written about the benefits, its origins, and a 2-year reflection. Here are the log archives (WIP).

July 16th, 2024

Here’s the tldr of my update:

  1. I’m writing a textbook called Essay Architecture, which is based on a 27-part framework (it’s a 3x3x3, with the root 3 being idea, structure, and voice).

  2. Dean’s List” is now a public list of ranked essays that I’ve scored using this framework.

  3. I’m developing an AI app that can score your draft, give you feedback, and point you to the chapters to start with based on your weaknesses. “Think of it like Grammarly, but instead of neutering your prose through line-edits, it asks you profound questions to help you formulate Draft #2.”

I'm interested in how Dan Shipper shifted his stance on the Apple Vision Pro. The subject of today’s Every email is “What I got wrong about VR,” and the last header is “These devices might be spiritual death.” It supports the idea that emerging, exotic tech can be extremely powerful on first use, but overtime it presents a moral dilemma.

July 15th, 2024

An essay about the selection of the cover band for the RNC.

On the power of syntax-loose, image-first stream-of-consciousness (or, “prose poetry”) to cause a trance state.

“Apocalypse” doesn’t mean the end of the world, but the unveiling of truth. It’s the shock that comes from the end of a paradigm. I forget where I’ve heard this metaphor (Douglas Rushkoff?), but imagine that in your childhood home, in a hatch above your closet ceiling, you find a secret attic compartment where a team of 8 elves have been technologically monitoring your entire life and relaying commands to everyone in your life, Truman-show style. It would be radically disorienting.

I think Trump’s failed assassination attempt could unleash a radical chapter of disorientation in America’s consciousness. I think it’s more than likely that this was a lone-wolf shooter, but regardless of what actually happened, Trump is a conspiracy peddler. He’s memed “the deep state” into Netflix existence. He’s teased the JFK files. Trump has been uncharacteristically reserved since the attempt, and we’ve yet to see his freewheeling interpretation of what happened. What if he likens himself to JFK and turns more than half the country on to a radical—true or not—conspiracy? What if, on the dime, the whole left vs. right axis shifts to become about the state vs. the rebel?

When we think of the person who will reveal unjust power, we imagine a noble hero. Trump is an anti-hero. He is his own ball of deep corruption, colliding with another one, unraveling it. There are no good guys, just chaos in an imbroglio of a power crisis.

July 14th, 2024

Hiked 7 miles at Harriman State Park.

Drove by two indoor skydiving facilities in one day.

July 13th, 2024

I’d define a “conspiratard” as someone who defaults to seeing collusion behind every event. It’s max paranoia for every news story. There’s a foolish certainty that the shadow story is always correct, and this strips the main value of conspiracy thinking.

I’ll make the stretch of a claim that conspiracy thinking is actually a value meta-skill, if and only, you never commit to any conclusion. The conspiratard is as dogmatic as the person who trusts the news, but the agnostic who’s open to 16-possible explanations is able to swim in ambiguity.

A truly critical thinker can map out any event in a probability cloud; they don’t find comfort in something that’s 80% true, nor do they find comfort in counter-narratives. They are permanently uncomfortable, and that’s a superpower.

July 12th, 2024

Paul Graham’s essay “The Age of the Essay” (2004), doesn’t fully live up to the promise of its title. It gave a fascinating backstory on why English class is as tormented as it is, and he gives a good sense of what an essay is and how to write one. But he has only a few paragraphs at the end about how the Internet will revive this medium. That could have been—as the title suggested—80% of the essay, but it was less than 8%. That essay is—to my knowledge—yet to be written.

Paul Graham, on essays, from “The Age of the Essay,” in his section, “The River.”

Fundamentally an essay is a train of thought—but a cleaned-up train of thought, as dialogue is cleaned-up conversation. Real thought, like real conversation, is full of false starts. It would be exhausting to read. You need to cut and fill to emphasize the central thread, like an illustrator inking over a pencil drawing. But don't change so much that you lose the spontaneity of the original.

“Here is New York,” is the title of EB White’s famous NY essay, but the title doesn’t capture his thesis, which is about the mysteries of extreme density.

July 12th, 2024

Imagine a dystopian app that’s a fake social network. Everything you post goes viral and gets flooded with love and attention from bots. Here.

Starting a club of essayists who all publish essays on the 1st of each month.

Press release:

Michael Dean Will Use His Grant to Develop Essay Architecture, a Textbook and AI-Powered Editing Tool for Writers

GREENWICH, Conn., July 12, 2024 /PRNewswire/ -- O'Shaughnessy Ventures LLC (OSV), an investment firm that empowers creators, has awarded an O'Shaughnessy Fellowship to Michael Dean, an editor and writer based in New York.

Dean will continue to develop Essay Architecture: a 27-point framework, based on hundreds of classic essays that Dean is deconstructing, which will serve as the foundation for a textbook and an AI-powered editing tool. Dean will finish writing the Essay Architecture textbook before switching focus to the AI-powered editing tool, which will instantly generate an in-depth report based on any draft the user uploads—identifying both strengths and weaknesses, as well as providing stylistic and structural feedback.

An architect by training, Dean has spent the past four years obsessively reading, writing, and editing essays. Now, with Essay Architecture, Dean is combining his passions in order to uncover the secret architecture of great essays. He regularly publishes his own writing on his Substack.

OSV's founder and CEO, Jim O'Shaughnessy, commented, "Despite the influx of new and exciting technologies, writing—one of our oldest technologies—has remained as central to our civilization as ever, and while AI alone will never fulfill our need for great writing, it has the potential to be an incredibly valuable tool for the writers of the future. We were immensely impressed with Michael's interdisciplinary expertise, and look forward to supporting him usher in a new era of essay writing."

"The OSV Fellowship will give me the momentum and support to create something that could elevate the quality of writing across the Internet," said Dean. "I'm excited to be immersed in a network of thinkers and technologists that fuse analytical and creative thinking."

July 11th, 2024

Trump is presenting at the Bitcoin conference in Nashville.

Boondoggle is a new favorite word of mind. Here’s the formal definition: “work or activity that is wasteful or pointless but gives the appearance of having value.” But so you know, a "doggle" is a pair of sunglasses that stop dogs from staring at the sun, so a boon-doggle is something like “blinding hype” that is occasionally dogshit.

July 10th, 2024


  • Live the question, not the answer.

  • Consciousness might exist to grapple with paradox.

  • Love the strangeness, tolerate chaos.

  • Measure your play, play with your systems.

  • Good systems disappear.

Whether we look in or out, up or down, we find infinite complexity. As you jet ski towards the horizons of minds or stars, it goes on and on with no ends or absolutes, just the same pattern recursively looping on itself. We get paralyzed with cosmic angst. We wonder if we have free will. We ask why build another house if the last 100 collapsed. Maybe we’ll never find the end, but we can stretch in each direction of infinite, down to the minutes and up to years, and create signposts at different scales of loopage. We can arrange mirrors in specific ways so that actions of the day reflect through mazes of intent, to illuminate the future.

In Leaves of Grass, the root mystery is that the inside of the house is bigger than the outside of the house.

Solving the Ps of P:

  • Paradox of Plenty (find a trusted curator who opens a portal).

  • Paradox of Pre-destiny (short-term agency, long-term destiny).

  • Paradox of Passion (peaks stabilize into new defaults).

  • Paradox of Providence (the walking distance mysteries).

Shallow vs. deep systems

In 1729, Jonathan Swift (of Gulliver’s Travels) posted A Modest Proposal. It was a satirical essay published anonymously. To criticize Irish/English economic relations, he proposed that the Irish sell their babies to the wealthy English as food. Perhaps this could be an example of how you can study the form of the essay independently from the content (in this case, not even the author agrees with the literal content).

TikTok NPCs streamers are at the frontier of audience capture. It’s optimization turned circus.

While mastery is the road to masterpieces, the infinite approach of mastery breeds other traits that have nothing to do with art: it brings confidence, it teaches meta-skills, it forges identity, and it cultivates your lens to the world. Mastery shapes the soul, making it a worthy pursuit, even if masterpieces can be generated on demand.

July 9th, 2024

The Marginalian on mantras:

“Unlike a prayer — which channels a hope at some imagined entity capable of interceding in favor of that hope and has only as a side benefit (though arguably its only real and robust benefit) the psychological self-clarification that comes from honing our hopes in language — a mantra is not addressed at anything or anyone external and is entirely devoted to distilling the object of hope to its clearest essence. This, in and of itself, transforms the hope into an intent, making it more actionable — but also saving it from the particular complacency against which Descartes admonished as he considered the vital relationship between fear and hope. A mantra is therefore not a form of magical thinking, for while there is a sense of magic to how such distillation seems to shift the situation by its very utterance, it is an entirely practical sort of magic, for a mantra simply clarifies, concentrates, and consecrates intent, and all meaningful transformation springs from purposeful, devoted intent.”

July 8th, 2024

July nights in a rented house in the Catskills. You know the neighbors name is Ned, but you don’t know if he’s actually the neighbor. No air-conditioning, so sounds of fans bleed into the sounds of vinyl. It’s rickety. Every flush creates a crashing sound after 10 seconds. Hard beds. No mice, but moths.

I’m not sure how this dragonfly got indoors, but the reward for saving it was watching it vanish into a pixel in the sky.

July 7th, 2024

When you’re driving west through mountains and the sun is setting, you get all these extreme patches of light and dark as you zig around bends. There are moments of extreme glare, where you can’t see anything in the shadows ahead, and all you can do is follow the road markings. There’s a metaphor in there.


Far left or far right, fundamentalist or work—what if the whole spectrum is part of the same phenomenon: a fear of ambiguity. We can’t tolerate not knowing who we are, or whether an afterlife exists, and so it’s comfortable to cling hard to one answer, and fight the others. This is an ego glitch. The ego is a control freak and is desperate for solid ground. Uncertainty is worse than death.

This could be why public speaking is the greatest fear, it’s a social society where you transmit an idea beyond a social scale you can read, and you have no idea how your ideas rae being received.

Instead of using words like “certain” or “various,” you can show the range so your reader gets it. Instead of “various topics,” list them: “topics like X, Y, Z.”

A short story about a birthday convention. It’s the same event everyday, except a new crowd each time. Today, everyone born on July 7th, of all ages, gather. Everyone is celebrated. It’s manic. What is something unexpected that might happen?

We’re entering a “virtual” reality, meaning our virtues are becoming more consequential than ever. We are in a slippery, frictionless sensorium, where every impulse is leveraged to its ultimate realization. If we aren’t rigorous about our character, then we’ll all escape into cheap palaces.

July 6th, 2024

Just like only 1 in 200 million sperm will go on to fertilize an egg, maybe a similar radical filter applies to the number of intelligent species that can escape their planet.

5:05 am — There are—at least—two kinds of logs I write: some come through as breadcrumbs from a busy life, expanded into prose one or many days later, while others come from stillness. When I read Pessoa, I remember the second kind. There’s no perception or emotion too ordinary to transclude into prose.

5:00 am — Pessoa writes, “I know it philosophically and in my flesh, through a hazy, gladiolated* foreglimpse.” I look up the word gladiolated, and the first search result is from “italki,” a language learning platform. Zhanghongxiang asks, “what does gladiolated mean?” R. Griffiths snarks back, “Not a word!”

A gladiolus is a plant noted for being brightly covered, and the word itself stems from “gladius” which means “sword” (sharp colors on a sharp plant). The suffix “-ated” turns the noun into an adjective.

There are more latent neologisms than any dictionary can contain.

4:36 am — Some words from Pessoa:

  • peregrination: A long journey or period of wandering from place to place.

  • drawling: Speaking in a slow, lazy way with prolonged vowel sounds.

  • moribund: In a dying state, near death, or in terminal decline.

July 5th, 2024

9:11 pm — This line from “Self-Reliance,” might be sticking more than any other line: “My vice and virtue is not only communicated by overt actions, but in every breathe emitted.” It speaks to real-time awareness, to never lapse into unconsciousness or automaticity.

The arena of “character” (honor, virtue, personality) is sometimes considered too far out, to life-defining moments. But there are not just 3 or 4 appraisals per year that are used to weigh your honor; there are over a hundred per day. Half of them are illegible to all but you. The other half are legible to everyone BUT you.

I’m not endorsing a pervasive moral paranoia in every action. There are forms of self-consciousness that are so intense that you forget how to breathe automatically (this can happen to new meditators; it is attention over-harvested). But, I’m inspired to “stay in the pocket,” where my virtues escape their sheen of abstraction and percolate every frame of embodiment.

I’d extend Emerson’s quote so say “every breathe and bite.” I’ve been trying to eat more consciously. I am usually a wolf. I’d win competitions. I’m trying not to just slow down, but to embody a form of prayer where every fork transport, bite, and swallow have a symbolic meaning. This is part of hermetic ritual, and I’m sure it’s a part of Christianity, Judaism, and all religions. (FWIW, prayer is not just a poem recited before you eat, it’s a sustained awareness AS you eat.)

The thing I like about hermeticism is that it doesn’t impose language upon you. It shares the same attentional practices as all religions, but—almost like an adlib—hermeticism lets you fill in the blanks.

I will be thinking of this Emerson line while I chew.

5:57 pm — It’s settled. Going to change my Substack name from “Dean’s List” to “Essay Architecture.” Dean’s List is going to refer to my list of ranked essays.

Essay Architecture is something like a synecdoche, where the part and whole equal each other. It is both the master umbrella, and also one of several projects within it.

4:04 pm — I’m basically always focused on the writing of my book instead of the theoretical success of it, but for a brief moment, I was plagued/graced with the I’m-going-to-sell-a-million-copies energy.

3:52 pm — Zero to one.

3:41 pm — When you let AI do you writing for you, it reverts to the mean and becomes bland. Instead, AI can be trained to ask you amazing questions that unlock epiphanies for you to say in your own words.

3:37 pm — One way to tank the trust of your customers is to over-hype new AI features that are unreliable. This happened to me with Notion. You get the sense that some product manager had to hit a deadline and throw the feature again, regardless of how often it delivered the intended results.

I could ship an AI editor TOMORROW, but it would have a 30% margin error, which is way too high. On a 2nd generation, 2/3 of the scores would be different. I feel a responsibility to exhaustively test and verify that what I put out closely matches my own taste and standard.

My solution is to have a “confidence score” for each pattern. Some patterns will be easier than others to make deterministic, and transparency here will go a long way.

3:28 pm — An Ur pattern is a primordial design archetype. Different medium have different rules. I’m making a case for 27 Ur patterns of the essay.

These are so hard to detect because each pattern has multiple expressions. It takes an archaeologist to look at 10 disparate things and say, “those 5 are different instances of Pattern X, these 4 Y, the last one is Z.” It’s a game of taxonomizing what appears to be noise.

My sense is that there is some universal resonance between each medium and the human psyche. Unique to the medium of writing is linear text; when you combine this with a species that has limited bandwidth, processes event casually, and yearns to see, hear, and feel, you get all the nuanced varieties of prose.

3:23 pm — It hit me that the 4th of July in America is the opposite of a total solar eclipse. Both involve the mass phenomenon of necks turned up coast to coast, but the spirit couldn’t be more different.

The fireworks in Bethpage go on for 3 hours, but the eclipse is 3 minutes. One is loud and raucous, the other is silent. One features multiple points of powder rapidly exploding in random directions, the other features a slow moving space rock. One fosters country music, the other Pink Floyd. One is about exuberant patriotic freedom, the other is about contemplating a cosmic mystery.

As a kid, and even as a teenager, I remember hazy mid-year nights and looking up to explosions of color with a sense of wonder, but after seeing two totalities I can’t help but see fireworks as a monkeyish drunken spectacle.

The worst is when people set off fireworks during the eclipse.

3:18 pm — I started architecture school in a Classical program, but quickly transferred to a Modern one. Most importantly, it wasn’t Postmodern. Modern architecture is (regrettably) stripped of ornament, but it’s still in tune with the fundamentals of space and composition (where post-modern architecture has drifted into delirium, schmaltz, and what Tuzz called “formal masturbation,” sometimes facilitated by kids playing with algorithms they can’t quite control).

2:59 pm — Writing essays on the Internet over the span of many years is how you break out of circumstance to do your life’s work.

2:51 pm — My goal is to understand limits of how our canonical rules of writing can become machine legible.

2:43 pm — The COCA (Corpus of Contemporary American usage) is a database of 1 billion words, collected from 8 evenly-sized sources (from movies, speeches, novels, etc.). It is a proxy for what is familiar.

The word “love” is used 250,000 times in a billion (1 in 40). “Confuse” is used 2,500 times, while one of its synonyms “addle” is only used 25 in a billion word. Notice the multiples of 100? Confuse is a “familiar” word, where something 100x more used than that risks being cliche, and a word 100x more rare than that risks being pretentious.

When it comes to word choice, a writers wants to default to this middle band of familiarity, but they don’t want to be stuck there. They should make cliche word foreign, and foreign words familiar.

This can all be statistically measured. You can download the COCA database and reference it. Imagine turning a draft from words into numbers. Each word gets a score: how many times is your word used in the billion-word corpus? A sentence might look like: 4529 29 450293 39208 4900 4921 12 4920 4 … From this set, you can find the mean, the standard deviations, and the outliers.

10:12 am — Note from Henry Oliver:

“When my kids ask why we have education I say that you have to spend your whole life with your own mind—better make sure it’s an interesting place to be.”

8:34 am — The Flescher-Kincaid readability score only measures averages. It’s based on your average sentence length and average syllables-per-word over the entire piece. This standard makes sense for instruction manuals, but not for literature.

According to Wikipedia, Reader’s Digest has a 65, Times Magazine has a 52 (6th grade), and Harvard Law Review is in the low 30s. The highest possible score (max readability) is 121.22, which would require sentences with only one-syllable words, but there’s no floor to how hard something can be.

In Moby Dick, “one particularly long sentence about sharks in chapter 64 has a readability score of −146.77.” I’m not sure if this is the record, but Marcel Proust has one sentence that scored −515.1.

July 4th, 2024

Don’t look at the fireworks, but the way the faces of houses flicker in light, to the exploding sounds over endless suburbs that have never heard the thunder of war.

After editing thousands of essays, editors build an intuition about the essay’s hyper-object. The question is, can you build that same intuition into a script?

Here’s my metaphor for why ChatGPT prompts lose their luster over time.

An LLM is spatialized language. Every prompt is like a vector that goes into a maze of mirrors, and comes out in a random direction. By knowing the end result you want, you can keep adjusting your prompt until it becomes useful. The problem is, every few days, all the mirror shift. Only slightly, but that’s enough for once reliable vectors to shoot in random directions.

This is known as “latent space shift” or “vector space drift,” or even, “prompt drift.”

Can AI write jokes?

Reading about computational criticism, here and here.

Instead of a scholar reading 200 books, a machine can read 200,000 books. These studies are trying to find “morphological signature” in the canon. They say that “patterns are the shadows of forms over data.”

I’ll need to write more on this, but some of the conclusions here feel targeted towards, “look what we can do with data,” as opposed to practical insights around writing.

Rhythm isn’t just about sentence length. It also includes syllables, sentence types, and the patterns between dependent and independent clauses.

From Randall’s draft:

“It took me this long to gain the deepest form of self-confidence, the Ancient Greek term κυβερνητικός (kubernētikos, ‘(good at) steering’). This is faith in your own judgment--accepting the responsibility of choosing and choosing well. Not what to die for, but what to live for. The courage of conviction.”

  • Claude Shannon: information theory

  • Stafford Beer: cybernetic theory

July 3rd, 2024

What if I made a yearly printed anthology of my best published essays?

Virginia Woolf:

“The eyes of others our prisons; their thoughts our cages.”


“Music is liquid architecture;
Architecture is frozen music.”

DFW on The Marginalian, and the circled words in his dictionary.

July 2nd, 2024

In the back of a supermarket in Flushing I saw a dozen live crabs stuffed into a brown grocery bag.

Everyone has the capacity for free will, but we underestimate the forces of the currents that pull us towards likely predestinations.



“The most beautiful thing we can experience is the mysterious. It is the source of all true art and science. He to whom the emotion is a stranger, who can no longer pause to wonder and stand wrapped in awe, is as good as dead; his eyes are closed.”

Wordcels, shape rotators, and symbol manipulators.

While searching for a book on Aristotle, I got a sponsored ad for Meditations, which featured an AI-generated talking statue head, saying, “think of what a privilege it is to be alive,” which feels like an appropriate thing for a non-human to say to a human.

Hermeticism is a fusion of Ancient Egyptian religion, classic Greek philosophy, Christianity, alchemy, gnosticism, and Islamic mysticism.

Romantics vs. realists.

July 1st, 2024

Your subconscious projects a hologram of a lesson you failed to learn during a traumatic experience, and plays it over and over until that disturbed part of yourself resolves the loop. It doesn’t matter if the “wise self” (from IFS and other models) knows the lesson; it has to enable the older complex to integrate it.

America as civic technology. It established an architecture to leverage and balance power. Over centuries of oozification, it became the thing it escaped, and is now calling for new civic inventions.

The blackhole as a metaphor in consciousness. Despite an infinite interior, the blackhole is something like an escape hatch; the obliteration of ego into a new paradigm. On the other side is madness or reinvention.

Rogue runway (a bizarre AI-generated fashion show).

An essay that analyzes the marketing copy of Trump Cards, which features snippets of the suit he wore for his mugshot. The website refers to the opportunity as a "very, very special deal."


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