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Michael Dean
michael-dean-k/

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

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#creator-economy20 pieces
Michael Dean
michael-dean-k/

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Essay Club ↗
Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Essay Club ↗
Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

A Paradigm for Frameworks

· 1,792 words

Every online creator these days has a proprietary framework—they are catchy, dead-simple, sometimes flimsy, and often wrong. Somewhere exists a marketplace of mental models. Maybe Farnam Street. Is a mental model a framework? What even is a framework, and what makes a good one?

Consider the "frame-" prefix. A frame is a vantage point, a particular angle, a way of looking at something. Imagine holding out a picture frame that gives you a little glimpse of a vast national park. You can't hold an entire hyperobject in your mind, and so a frame compresses noise and gives you a shortcut for understanding. You can't see the whole park, but you can see a map. A framework is a system of lenses to decipher complexity. It lets you leapfrog in understanding.

By creator-economy logic, a framework is a valuable asset. Unlike a vague mush of regurgitated ideas, a framework is discernible, seemingly original, and something you can call your own—you can coin it as a phrase and repeat it over and over until you're known by it. This is a useful tactic! The evolutionary pressures of Internet feeds have forced conceptual ideas to become salient, simple, and tangible. Unlike the abstract frameworks of a physicist, these are fit for a TED talk, primed to leak into the memeplex and anchor your name in the annals of Internet-niche-celebrity history. This is, overall, good—it democratizes conceptual knowledge; the problem is when, beyond the positioning, it's intellectually flaccid.

You've probably seen frameworks pitched as "The Six Types of X," or "The Y Method." These are pseudo-frameworks; they are more like sets or lists. They assemble things within a domain, and increase their memorability through alliteration and metaphor. Maybe this helps with recall, but it doesn't reveal the inner structure of a domain. A real framework would give you a schema to classify incoming data in an unfamiliar field; but a set/list only refers to itself ... Compare this to something like "POP Writing," a simple concept that classifies writing as personal, observational, or playful; this acts a lens to help you analyze any piece of writing.

For something to be a framework, it need generalizability: the ability to explain things beyond itself. The earlier examples are merely "collections"—things are presented, but we don't understand what Aristotle calls "the four causes": what it's made of, how it's arranged and interconnected, why it exists, and what's it's purpose? When Plato writes about conceptual forms, he says there are collections and divisions. Making frameworks are a matter of dividing; a framework's goal is to divide an incomprehensible whole into human-sized parts.

I spent some time this morning thinking through a "framework of frameworks." The first thing to grok about this meta-architecture is that it's broken into three levels of escalating sophistication. After that I'll explain how levels have shapes, and how any shape can be evaluated through a set of qualities.

So it's level, shapes, and qualities—that's the gist.

To expand on levels: a framework can be a heuristic, a model, or a paradigm. Now that I think about, I suppose HMP (not quite meme-ready) is an attempt at making a "paradigm for frameworks," which will soon make more sense, and sound less like bashed buzzwords.

The three levels of frameworks:


Heuristics—mental-shortcuts that lets you decipher complexity through a single property. When Aristotle was classifying animals, he'd offer differentiate them across single properties: blood or bloodless, horned or hornless. A heuristic is something you derive a posteriori, from experience, from empirical facts. You might observe a bunch of essays, or companies, or girlfriends, and notice that you can compare and contrast items in a set based on single attributes. There are many shapes a heuristic can take: it can be a classifier (type A, B, or C), a boolean (on/off), a spectrum (A<>B), a rubric (I, II, III, IV, V), a score (1-100).

The benefit of a heuristic is that, since it's often anchored on a single property, it's simple and easy to learn. The downside is that it's a very limited frame on the scope and purpose of your domain. For example, if you're trying teach craft (purpose) for online nonfiction writers (scope), then POP writing is an excellent heuristic to classify writing voice, but it doesn't teach you how to scope ideas or structure an essay. A heuristic is a shortcut to understand one facet of a domain, but it's not an attempt to model the whole domain. 

Models—a series of interlocking properties, all organized with a larger frame. Write of Passage was set up like a cabinet of heuristics (POP writing, Shiny Dime, Write from Conversation, etc.), but they weren't organized within a single higher-order framework. Think of a model as a group of heuristics organized in hierarchy, where each one is named (what is it's essence?), labeled (what other concepts is it similar to?), located (what is it's parent concept?), interlinked (who are it's cousins?), and excavated (if we go infinitely deep, what are the variations?). Models can take many shapes: an XY graph, a taxonomy, a multi-step recursive workflow (like an OODA loop).

Models cover far more than any heuristic can, but it risks collapsing into complexity. Conceptual schemas can bloom, sprawl, and contradict—becoming illegible or incoherent. To solve this, you have to shift from empiricism to rationality; you can notice infinite ways to subdivide a thing, but to make an elegant model, you need to shift to abstraction and question the fundamental truths behind it. Why might one set of properties be more elegant than another? Ultimately you have to make a hypothesis, test it across dozens of examples, and see if it holds. If some foreign object can't be reconciled into the schema, you have an issue. Consider how the taxonomy of Carl Linnaeus was able to classify the animal world into kingdom, class, order, genus, and species, but it wasn't unable to find a home for the platypus. Even though it works across thousands of animals, the original assumptions aren't able to handle edge-cases.

Paradigms—comprehensive systems that can explain or predict any phenomenon within a domain. How is this possible? I think you achieve this when (1) you find enough instances to represent the domain; (2) you analyze them deeply enough to understand their underlying nature; and (3) you can arrange all your findings into a coherent architecture with maximum explainability. Consider how Darwin improved over Linnaeus: he shifted us from a static taxonomy to a dynamic model, a new paradigm that explains the origin of species, and even the potential future of a species. Paradigms can also take on many shapes, from living systems, to digital networks, to compositional pattern languages.

A good paradigm often finds simple root causes underneath complexity. For example, even though Essay Architecture has 27 patterns (3 patterns within the 3 elements of 3 dimensions), every tier is explained through the rhetorical appeals of ethos, logos, pathos—the whole thing can be summarized as "Aristotle all the way down." Maximum compression has a degree of a recursion: a single heuristic works as a fractal and organizes complexity at multiple scales.

Regardless of how you simplify and package a paradigm, it's still as hard to learn as a language; it's the least accessible, but it's the level that enables mastery of a domain, and the level most suitable to build a school around.1

No matter how confident you are around a paradigm, it's always fragile. It's explainability is limited by the data set you test it against. As society develops new tools, it brings new data that eventually breaks a paradigm, even if it's held true for centuries. The telescope cracked the geocentric paradigm. A shattered paradigm is disorienting, but fundamentally good—it means you've discovered some new heuristic of reality, and humanity has to restart from new axioms.


So that's a first attempt to map the three levels, and it might help to think of them as geometric dimensions. A heuristic is like a one-dimensional line, a ray of insight that you perceive in a field. A model is a two-dimensional plane to understand a multi-property condition within a domain. But a paradigm is the three-dimensional totality of a field. A paradigm contains all possible heuristics and models, and so when you can think in 3D, you're able to match any circumstance with the correct solution.

But a paradigm isn't necessarily a great framework! It might be the most successful in compressing reality into a particular shape, but it might fail along other qualities. (To reiterate, levels are about  "compression sophistication," where shape is the particular form of compression...) Qualities capture how a compression framework interacts with society as a whole (the point of a framework is, in the end, to spread understanding).

Regardless of the level or shape, some qualities to consider:

  • Tangibility: have you made it graspable through metaphor and lexicality?
  • Salience: is it rewarding or effective to understand?
  • Transferability: does it explain things in other domains?
  • Correctness: is it actually right?
  • Approachability: how would you walk someone through it via curriculum?

Are these the right qualities? Are these all the qualities? Can I reduce these into more fundamental qualities? I don't know. Realistically, this isn't a "paradigm of framework" yet; it's more so a "model of frameworks." I only conceived of this today, and so naturally it's sprawled into a series of properties:

A framework compresses complexity in a domain, exists at a level of explainability, taking on a particular shape to achieve a purpose within a scope, and can be judged along a set of qualities on how well it's memed.

To properly turn this into a paradigm, I'd have to test this hypothesis against hundreds of frameworks—ie: creator economy memes, among other disciplines—to see if it holds up. I imagine the concepts would melt and reform several times until it's simpler, sharper, and better at explaining a wide range of frameworks. A paradigm isn't solid until it's a domain has run through its pipes. A paradigm is really just a reflection of a domain's dataset and the mind making sense of it.

Footnotes

  1. I aspired for Essay Architecture to be a modern, technology-forward school. My pattern language feels totalizing: if you give me any one of the hundreds of Latin rhetorical concepts, I believe I could locate it within my paradigm. Yet I still don't fully know the inner-working of every pattern. My latest AI system can match my own judgment with 97% accuracy, yet, it can't yet convert that judgment into concise feedback that will improve the essay. Feels like I've nailed decoding, but haven't yet touched on encoding.

Avoid shipping logistics

· 460 words

I resonate with the vision of Metalabel—artists collaborating and splitting royalties—but after finishing a project with it (The Best Internet Essays 2025), I’m not sure if I’d use it again for a self-published print book. I imagine this works so much better with a digital product, but for a physical deliverable, I found the convenience of automating the royalty split to not be worth the friction of handling shipping. (I’ll describe my process, and if I did something wrong, please correct me.)

All purchases happen through the Metalabel storefront, and from there you can export a CSV that you can bulk upload into a tool like Lulu (an online printer). I decided to offer the anthology (The Best Internet Essays 2025) for a limited window, otherwise I’d have to handle shipping logistics at a daily/weekly level. But even with a single shipment, I ran into trouble. The first issue is that a lot of countries require a phone number for shipping. Metalabel didn’t collect that, so I had to put 1-111-111-1111, which got flagged for some countries, requiring me to use my personal cell phone. Other countries required a tax ID, and I’m still waiting to hear back from the buyers so I can ship them their copy. Another thing I didn’t think through is the return addresses. I assumed that the printer would provide their own address, but instead they used the name/address from my credit card, which I did not intend to share! I’ve been writing under a pseudonym, and this doxxed my last name to anyone who purchased.

The other problem was that so many people—in real life and online—were confused why the sale had an end date. Books don't typically have deadlines. Even those who knew the deadline procrastinated, and were bummed when they remembered they forgot. Again, my decision, specifically because I do not want to be regularly porting over CSVs and manually handling the edge cases that are inevitable.

In the future, I’ll likely set up a storefront where a reader can purchase it themselves, input their address and any required information for their country, and then get their own unique tracking ID. And, considering so much effort goes into making a book, I wouldn't want to limit it to a one-month window; I'd want it open forever, or for years, at least. If I do a royalty split again, I can set some interval, maybe once per quarter or year, and then ask the contributors to invoice me. None of my friction above was specific to Metalabel functionality (the whole platform as it is was very pleasant to use, and it's Lulu that I'm frustrated with), but because they aren't integrated with a shipping platform, it requires logistics that are annoying and avoidable.

Do paid subscribers influence discovery on Substack?

· 538 words

Chris Best, founder of Substack, posted that they caught “President Plump,” the #1 growing account on Substack, for using fake subscriptions to boost discovery. I think this was intended to comfort everyone that they caught a scammer (justice!), but actually it confirmed what many were starting to notice: discovery is contingent on you making money. If you have paid subscribers turned off, no algorithmic wind will blow your way. But if you have a spike of paid subscribers in a month, suddenly your old posts will start to go viral, in hopes that even more paid subscribers will bring the platform 10% (this has happened to me before). This isn’t inherently bad. For every President Plump, there is an earnest person trying to finance their creative project.

But at scale I fear it creates a bad pattern, because the accounts that everyone sees will be the ones making the most, and generally these will be marketers and growth hackers more than artists. I think you will find better writing in the gutters of Substack than on their rising leaderboard. If authentic culture emerges outside of monetization, then there’s a real rift between what Substack wants to be (“an engine for culture”) and what it actually is (an algorithm that only rewards monetization).

I think the best we can do is use this information to our advantage. For example, I could have new Essay Club members pay directly through Stripe, but by handling payments through my Founding Members tier on Substack, I get a discovery boost, which is worth the 10% fee. Similarly, if you make small digital products, it might make sense to bundle them into a subscription instead of charging per item.

Should you use a credit card masking service to give yourself 20 paid subscriptions for $5 each? Depends. Basically, for $10/month, you can pay for a probably noticeable increase in discovery. The question is, will you get caught? Maybe they are on the lookout now, but my guess is they would only penalize it at a certain scale. Sam Kriss speculated that President Plump was paying himself around $5,000 per month to reach #1. I’ve never done this, and wouldn’t necessarily recommend it unless you have a hacker mentality and really need the growth. 

At the very least, you should consider having paid subscriptions turned on. Cate Hall found success in charging $1/month and getting to #1 rising. Our very own Yehudis Milchtein also set up $1/month subscriptions and is now #91 rising in literature.

However you approach this, it brings up a bigger question for me on how to build a real engine for culture. It seems like you can’t have an algorithm for a single reward (popularity or money) or else they will be gamed; instead you could give everyone curatorial power relative to their cultural reputation, however you measure that. For example, if we all trust Ted Gioia, then somehow Ted’s like should count more than 10,000 bot likes or $1,000 in fake subscriptions.

I hope this triggers more transparency from Substack on how their algorithm works, and also hope for a new generation of platforms where each person has visibility into and control of the thing that is routing them information.

Medusa of Marketing

· 29 words

It is important to avoid learning best practices for marketing, for that’s like seeing a Medusa that turns your tongue to stone and never lets you be real again.

Why doesn't Substack create funds for it's on-platform creators?

· 222 words

I didn’t realize that Substack is open about paying off-platform creators to join their platform. See their $20m accelerator fund. My quick understanding is that, if you make $X revenue/year elsewhere, they guarantee you’ll make that, and will make up the difference if after a year, you don’t. A friend thinks there’s an additional secret fund that pays bonuses for celebrities to join (ie: Dolly Parton, Charlie XCX). I was surprised by how articulate Charlie XCX was—I only have a meme-level understanding of her—but I suppose it’s possibly ghostwritten. Idk.

I don’t have problems with this, but what doesn’t register to me is why they wouldn’t allocate money to help the on-platform, original writers. Obviously, these kinds of things piss of 95% of their userbase. Even if there was something like $100-$1m for on-platform writers with audiences under 1,000, that would build a tremendous amount of goodwill. My guess (and fear) is that they have a business model blindness, and aren’t thinking along the planes of “what actually builds organic culture?” Instead, there’s a lot of rationalizing: “here’s why bringing Derek Thompson on platform is good for you” (but the obvious benefit comes from the 10% they get from DT).

It’s weird to me that in some sense I’m giving more to it’s existing writers ($10,000), than the platform that raised $100,000,000.

Substack's business model blinders

· 200 words

Just heard Hamish (on a livestream) say that Substack is a revolution, a “found economy,” that materialized 5 million paid subscriptions that wouldn’t have existed otherwise. What is a revolution though? I think I want to zoom into this positioning, because many words are being used interchangeably. Yes, it’s a new business model for monetization, but is that a “cultural revolution”?

It feels like there’s a bit of a fixation on the 10% mechanism, and the risk is that this reward function turns Substack into LinkedIn in the next 3 years. If the goal is to make a “culture engine,” you need to really ask what a culture is. If you’re culture is limited to paid subscriptions, it’s a small, unrepresentative, utilitarian culture, much more slanted to journalism and business tactics, regardless of an editorial attempt to bring a flair of literature.

We need to define culture (in terms of taste, values, and quality), and then make platform design decisions that have nothing to do with revenue. Of course, I’m not saying to abandon revenue focus; I’m saying that they need to allocate some percent of their attention to “doing weird things” to prevent a writer exodus as enshittifcation strengthens.

Despite the superwriters...

· 186 words

Will was surprised to learn that I think machine writing could soon surpass the best human writers. As the head of Essay Architecture, he thought my position would just be “no matter what, humans will always be better at writing essays than machines.” I actually have some pretty extreme predictions on the trajectory of technology (I guess you could say I'm an ambivalent accelerationist), but I guess I believe that AI progress is irrelevant to the fact that I will always enjoy writing and see writing through the chaos as an opportunity. So yes, I think machines will make essays that are history-defining, that are good to degrees that are unimaginable to us today.

This will, unfortunately, make it even harder for writers to have economic value; but realistically, it's already too hard. The Creator Economy is a game of power laws, and AI might shift the chance of success from 2% to 1%. But could the same technology help artists go from 1x potential to 20x potential? If AI kills the market for commoditized creative work, will it let humans focus on the right things?

Swarm virtues

· 274 words

"The Death of the Corporate Job" went viral on Substack: 3.3k likes in a few days (eventually went up to 20k, I think). I am pretty sure this was AI-generated. I don’t feel like posting about it though. It’s clear to me that this is a kid in his 20s, building an AI tool for career discovery; he sees this essay as marketing. It will probably bring him a lot of customers. He might possibly help a lot people. I’m sure he believes in his mission.

What irks me is that the essay has been instrumentalized. There are fake I’s with vague personal details. Intellectually, it’s a ripoff of Bullshit Jobs. There’s no structural clarity, and it loops through the same points multiple times. No tension. Flat voice. Awkward repetition. I understand why the writer did this, but I’m more concerned about the state of readers, because this piece’s popularity is really a reflection of mass readers.

It shows that most people care about the topic, and barely notice or care about how it’s written. What thye care about is having their pain validated. To go viral, write about mainstream pain. So if this is what the masses want, shouldn’t we not care about composition and just write psychology-targeted think pieces? I mean, if you want to just build an audience at the expenses of your own satisfaction, then yes, possibility. But the quality of your thinking, and the friction to derive something original and independent, gives you something more than fleeting popularity, it actually shapes your lens for the longterm, and you earn something that is transferrable outside of narrow social status games.

Contradiction as core value

· 222 words

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.

The incentives to plagiarize

· 411 words

#5 in science recently went viral for sharing that #2 in technology plagiarized her a year ago (right after #2 just went 10k-like viral, again). Substack is freaking. Plagiarism is obviously bad, and I think everyone is shocked to learn that #2 got away with blatant copy-paste work, but I want to focus on the nature of what was plagiarized along with why platforms reward cheap writing.

If someone else can put their name on your writing and almost get away with it, it means you haven’t written something only can you write. The plagiarized post was digital cultural journalism: mostly facts and studies, with only a few “I” mentions that are too vague to be anchored to any specific writer. Obviously it hurts to see your hard work get celebrated under someone else’s name—I’d be pissed too— but research is becoming hyper-commoditized. You have to assume it will be coincidentally/accidentally/purposefully refactored by hucksters, bots parrots, friends, and rivals. If #5 had integrated her research with singular, relevant moments of her life, it would be hard—if not impossible—to rip off. Personal experience is the last moat.

This situation feels like a predictable consequence of engagement-based competition. Among us are people willing to sacrifice craft for clout, at various tiers of insanity. I’ve been noticing high-volume accounts in the Top 10 with obviously AI-generated notes and essays. I wonder who actually reads/likes this stuff, until I look in the comments and realize it’s, likely, all bots. Is Substack status that easily hackable? I guess this is a growth hack that brings you an algorithmic edge in getting discovered by humans, so you can eventually replace the slop with your own writing?

As extrinsic games get increasingly weird, the status of winning them will get decreasingly valuable, I think. If #2 is a slopjockey, I don’t care to reach #1 because the whole game is now polluted (I’m actually a fan of leaderboards, but they need to be merit-based and unhackable). I just don’t know if platforms care to systematically fix this, because status-hackers create volume and speed that make a platform look vibrant to an undiscerning eye/investor.

Over enough time, I think misaligned platforms and those who hack them will eventually lose. The internally-driven writers have to put up with a lot of noise and chaos, but since they aren’t anchored in hacks, they’re less likely to have their means of validation suddenly disappear. It’s OK to be a tortoise in hell.

→ source

Vanity audiences

· 96 words

This Influencer Does Not Exist. Opening hook: “Anyone can be a hot girl online now.” The fact that AI characters are getting 100k followers, and 600k views per post is going to devalue audiences. I still think “who” is more important than “how much.” Sure, any guy can create a fake viral account, but what do they do with that audience other than the vanity metric of “big audience?” Better to have 1k followers of high-trust high-value people who support your every direction than 100k who want you for a single false thing that you’re not.

Artists online

· 75 words

To what degree is being personal online a form of commodifying the self into a product? I think it depends if you have freedom to evolve and have contradictory, wide-ranging ideas, or if you are niched-down, monetized, and benefitting the platform more than yourself. It’s cynical to say “cyberspace is a blackhole”; there’ room to be an artist online without getting sucked into the machine, it just requires a diligent adherence to the right values.

Illegibility vs. Hyper-legibility

· 95 words

Soda bottle and startups need to be hyper legible, but humans are inherently illegible: multi-faceted, contradictory, complex. In a lot of ways, the medium of the Internet requires you to be hyper legible. But I think there’s an interesting paradox where you can be both. You can simultaneously pass the 10-second test before someone subscribes, but then you can offer a cavern of complexity that some choose to wander through. If you’re over-optimized for marketing, you risk becoming over-optimized, perpetually delivering on an old, stale promise. Instead, you can set the expectation to break expectations.

The Replica Economy

· 153 words

I imagine there will be two kinds of agent companies: 1) for modular services (ie: generic SaaS coderbots for $1k/month), but also, 2) for replicating identity. In a world where everyone gets access to swarms of modular agents that move at unimaginable speeds, I think those with a “replica” will have the edge. A replica is like a centralized manager entity—one that has your corpus of principles, lessons, memories, ideas, taste, libraries, etc.)—to coordinate between all the agents.

If this comes true, it brings new leverage to writing out your thoughts in detail. Maybe for every 10k words I write, my agent swarm is 2x more aligned to my specific goals. However, it also inverts the norms of data privacy. There’s a trade-off: the more you use writing for distribution and audience-building, the more clonable you become. It’s causing me to think harder about when a piece of content is public/gated/private.

So if models, apps, and infrastructure become too cheap to matter, then the only thing left that’s scarce is personal data / personal perspective. You’d think Notion/Google are positioned to solve this, but it’s interesting to watch people use Cursor as their PKM system because it’s so easy to connect personal context with an array of models.

Podcast Jitters

· 158 words

The Jitters. How will this go? I think I’m imagining a storm of 100,000 haters. Or, at least, will the required process of editing and memeification invert what I believe?

Essay Architecture is all about complexity. In a way, it doesn’t require me to translate ideas or make them digestible and catchy; it’s about training machines with infinite patience to create a piece of software that is—to the user—simple and profoundly useful.

I guess this is a test to see how well the idea can be meme’d. Is this something you can enjoy listening to while you wash the dishes? It’s a hard constraint. A fun problem.

To tie this in with David’s tweet on how managers prompt people, an interview is something like a host promoting their guest to package their ideas according to the taste of the host. So in some ways this will be like my ideas through David’s vision for his channel.

20th vs. 21st Century Education

· 89 words

20th century college/career:

  • linear
  • singular focus
  • credential based
  • one income source
  • work in private
  • up front learning
  • declare major up front
  • exams is proof of success
  • hierarchy of teacher/student
  • go into debt to attend

21st century college/career:

  • non-linear
  • polymathic
  • portfolio based
  • multiple income streams
  • work in public
  • continuous learning
  • emergent major
  • market is proof of success
  • everyone teaches and learns
  • get paid to contribute to school

Institutional voice

· 187 words

Marketing emails from software comes across to me like polite begging. The desperation is veiled. They speak in modern idioms, wishing my family well while using exclamation points. Email broadcasting is already unnatural, and so instead of pretending to masses with the pleasantries of a 1:1 coffee date, have the courage to be yourself.

And isn’t “being yourself,” the thing a company can’t be? It’s inherently not a self, but a conglomerate. Who is speaking? Who is “team”? A more honest way is to “share the process,” to give people the glimpse of what it’s like in a company. But still, I think there’s something corrupting about letting a market dictate your decisions.

Of course, that’s what venture requires. But we’re entering a paradigm where software can be so easily made, that all of our ratios can flip. Someone can make tools for themself. If I’m making a tool for myself, I can not only show you the process of making tool, but the things my tool makes. That’s the ultimate proof. I don’t want to just share screenshots of text-editor features and shill you benefits; I just want to share the fruits.

If the founder isn’t actively engaged in the product, then why should we believe them? And so, that might be how to make a niche products long-term sustainable. Serve yourself, and let the small selection of overlapping others have access to it.

Why Write

· 769 words

If you’re concerned that an AI will soon write better than you, it’s worth asking, why are you writing? (I mean this sincerely, not as a dig). There are so many intrinsic joys and values in slowly and meticulously crafting sentences. It doesn’t matter who’s watching, what it’s for, what technology is available, what generation I live in, or if anyone else likes it.

Through writing and editing, slowly and manually and sometimes painfully, you discover what you think, who you are, and how you express yourself. If you’re not in the pocket with language, there’s no transformation, no evolution, no humanity. It doesn’t matter how many billion parameters Claude Sonnet 3.5 has, or the prompt library you bought for $49, or whether you’re on Pro tier—it matters if you’re willing to sit alone with your own thoughts for more than 5 minutes, and for hundreds of hours more. It matters if you’re willing to shed your identity over and over.

I get the source of panic: soon enough (2025? 26?) AI and its midwives could trample out 100% of humans at the “art as commodity” game—maybe that’s a good thing. It wasn’t a great game to begin with. It distorted all the incentives of human expression. It created monsters and beggars. ASI means that the transactional, mercenary, instrumental skill of “content writing,” will no longer have value. This will create a strange, noisy Internet, and I sort of hope it drowns in pseudo-drivel so that in its ashes we can form a new one that’s less like American Idol (commerce was illegal on the Internet until 1991).

Now for the contradiction: I make money from writing online. I have a Fellowship Grant which gives me at least year of security. I have, relatively, a good number of paid subscriptions, which is currently around 1/4 of a full-time income. I live in New York (not by choice, by birth). As much as I hope and believe that I can sustain a full-time income via writing (the thing I love), I also (1) accept that ASI could wipe out the whole cultural appetite for writing and send me back to a FT role at an architecture firm, and (2) even if “Essay Architecture” is a success, I need to protect my non-legible non-optimized, non-practical writing impulses. (Ie: I hope that on “launch day” of my app, I spend 2-3 hours on a typewriter essay about thumbs, or something equally trivial, unrelated, unproductive).

So while you can make money and build influence via writing, you definitely don’t have to. Maybe it’s about to lose some of its economic function, but we shouldn’t underestimate its cultural/democratic function. If you look back through history, most of the famous essayists had other jobs—they were lawyers, doctors, publishers, physicists, architects (Frank Lloyd Wright). Essays just flowed out of them. They couldn’t help it. I really think essays are the most democratic medium of the arts. Unlike architects, you don’t need millions of dollars to start. Unlike novelists, you don’t need years of focused attention. Unlike musicians, you don’t need to learn abstract chord languages and train your finger muscles. An essay is democratic because anyone, in their own language, in a day, at almost no cost, can engage with composition and meaning-making, and share it with their culture, even if it’s a single friend. It might be our most important form of leisure.

So maybe this approaching techno-apocalypse is an opportunity. It can scare us inward. It can shatter the dream that we can be a Mr. Beast, a niche hero, a perfectly legible and distinct human wrapped in plastic. The irony is that by going inward, you might just find the thing that has outward appeal. The best kinds of extrinsic opportunities aren’t the ones you engineer, they’re the ones that knock because you tinkered with your garage door open and accidentally found a new source of gravity.

To finish with AI: I’m all for it, so long as it is my assistant and not my sentence jockey. I will never replace my document editor with a chat pane, but I will invite agents to live in my margins. I’ll let them watch my words as they form, and then offer up research, feedback, and disagreements, all of which I’ll have to manually integrate. Slowness is the theme. You don’t change without immersing yourself in an essay. AI might give you insights, but you know they’re illusions if you’re not wet—if you’re not even in the pool. You can automate the outputs, but you can’t automate the watering of mind and blooming of character.