michael-dean-k/

It’s amazing how many tricks the mind can play to prevent you from picking and prioritizing The One Thing. I can declare I’ll do one thing per area, which is pretending to focus when I’m 9x overbooked. I can say “one hard thing per day,” but if each burst moves in random directions, then the average of those vectors may leave me where I started. I can write, print out, then pin it up and prayer to a single 3-year goal each morning, but if every task can loosely ladder up to it (through some round about way, because everything relates to everything), then there’s no hard decision being made.

A few months ago I wrote that my one goal was to hit $250k in ARR through “mission-driven creative work” by 2028 (via Essay Architecture). If something didn’t directly support that, I’d have to cut it. If you achieve your One Thing, theoretically, then most of your other problems are solved: my wife could stop working to spend more time with our daughter, I’d have more space to work on creative projects, we’d be closer towards getting a house, etc. This makes it easy to say no to personal projects that are obviously unrelated (ie: record an album, read the dictionary, hike 40 mountains), but even within what seems like the limited scope of “a writing business,” it is tricky to define the arrow from which everything else follows.

I am in many ways over-extended. On the business side, I have a curriculum, editing software, an anthology, and a community of practice. Then there’s of course my own essay practice. I’m able to juggle these five things, but each is held back from the sprawl. I focused on The Best Internet Essays from November 25 - March 26, and in that time I couldn’t iterate on the software, I couldn’t grow Essay Club, and most of my writing revolved around the prize & anthology. And, importantly, the decision to juggle meant that the core thing (the anthology) was probably executed at only 50% capacity.

So why am I resisting prioritization? I see as Essay Architecture as a “micro-institute,” a range of inter-connected pillars that work together towards a civic and personally-aligned mission. Software without a curriculum feels unanchored in learning science. Software without the literary prize angle could easily turn mercenary. Software without community loses the personal touch. If I’m not writing myself, how could I even know what the software needs to be? If I really wanted to double-down on the software, I’d raise money and build a team, and the incentives would require me to make software for knowledge workers, which would turn it into an auto-complete tool, my anti-mission.

I have been part of and observed companies where the personal writing practice of the founder was slowly neglected until total abandonment when empire building hit a certain velocity. This warning feels etched into me. The core reason I started Essay Architecture in the first place was to create something that was aligned with my own essay practice. I’d much rather be writing essays for 50 years with a modestly growing company than build an extremely successful and impactful company that doesn’t let me write until I retire in 50 years.

If everything should be in service of my own essays, shouldn’t that be my One Thing?

The reason I haven’t given myself permission to do this is because true, self-driven essay writing is hard to monetize. So it comes down to financial anxiety. But I don’t think I’ve honestly doubted my premise: is financial growth actually necesasry for me right now? Between the ARR I already have, a new part-time consulting gig I just started, and my wife’s income, we’re actually not far from my goal. It also turns out that my wife now enjoys her job after maternity leave (because she’s working part-time, not overtime), so even if my business took off, she might still want to work.

This feels selfish for at least two reasons: selfish because I’m not taking the path to best support my family, and selfish by putting my own needs over what paying customers of the Essay Architecture system might want. However, if you are focused on the Right thing, and are properly prioritizing and focusing, then you become a gravity well and matter bends in your favor. Paradoxically, but obviously, you can only build something useful for others (and, thus a company), if you are selfishly operating in your zone of genius. For me, that is not marketing, but essay writing itself. When I dial into and optimize for attention, growth, and revenue, it strips me of my vitality, and it doesn’t seem to work; might I get objectively better metrics if I were locked in and oblivious to the stats?

Craig Mod is a good example here. He’s a writer/photographer known for 300-mile walks through Japan, and runs a successful membership program that’s in serve of his personal work. A few lines from his rules stand out: “you are building a community,” but not managing it, instead “you must have faith that the work itself is strong enough to be a binding agent,” and “if the work isn’t strong enough, work more on the work.” This inverts how a traditional business-builder, or even solopreneur might think. It is you, the artist, at the middle; you are obsessed with your craft, but opening different pathways so others can work alongside you. There’s a way in which every part of my micro-institute benefits from doubling down on my own essay practice. If I write inside my own software, the software will naturally evolve. If I’m trying to become a master, then the curriculum is just the trail of what I’m already learning. If I’m publishing each month, then Essay Club is the tribe I do it with.

A friend and fellow acolyte of The One Thing, Matt Svarcs-Richardson, recently shared a paraphrased line from Joseph Campbell that resonates: “the vitality of a vital person vitalizes.” ¹ You will not inspire anyone into action unless you are operating at the edge of your flow, a flow that is very distinct to you, a secret flow you can get lost in for 10 hours where others don’t even know how to enter. This doesn’t mean to burrow into longform essays and ignore Essay Architecture. This means that my own writing is the spearhead from which the institute follows (even Emerson said that an institute is the shadow of one man). The software, the curriculum, the club, and the anthology are not separate businesses to grow and optimize for, but critical components of my One Thing, my essay practice.

This inverts the typical time-scale. Usually you focus on growing a business and then decades later, assuming it works, and assuming you still have the fire, you can begin working on the thing you’d work on if resources were no issue. Instead I want to start with the fire, and use that to slowly build an institute over decades.

Just prototyped an essay theme visualizer. This one is for braided essays, so you can see how the main focus shifts around, yet still references other threads to keep the whole thing cohesive. Then you can click into any paragraph and see how those themes weave in at the sentence/word level. I’ve done stuff like this with static images, but it’s a different thing to read an essay with animated overlays and full context. Now realizing that I could go through classic essays and make unique interfaces for each, to focus on different patterns. And then maybe, those same interfaces could help you see things in your own work? I have a lot of experimenting to do; feels like I need to enter a divergence phase, and then see what I can bring back into the Essay Architecture core app.

This essay tapped into a striking definition of timelessness. He doesn’t get there until halfway through though, and I found myself disagreeing with—or at least, questioning—a lot of his earlier points (I’ll come back to this). The main point is distilled into this: the best essays are “ineffective” because they reveal the timeless problems that each generation fails to synthesize. Timeless essays speak to the common foils in the human operating system: the blindspots of parents, the lies of institutions, the avoidance of mortality, the ineffability of relationships, the mundanities that are never captured in enough detail. These are different than “discovery” essays, like Darwin’s Origin of Species. The holy grail of an essay is surprise, and a timeless essay is not just sueprising for one generation, it’s surprising for every generation. And so timelessness, then, is a type of “breadth of applicability.”

PG also ventures into a familiar territory of “essay as a mode of thinking.” Where as in the past he used “the river” as his metaphor (2004), this time it’s a tree. You start from an origin, and then you explore many different branches in search of generality x novelty. What is a good starting question? He says a good one is “outrageous, counterintuitive, overambitious, and heterodox.” It doesn’t have to be a complete thesis, but some puzzling gap, and importantly something you care about. You won’t be able to stretch an origin question into cascading insight unless you have a unique angle into it. The origin doesn’t matter too much though, because it’s a recursive process, and you can eventually get to the best question in “a few hops.” I love how he emphasizes that you need to write to explore branches of a tree, and there are many dead ends; you realize how you are mistaken, incomplete, and inelegant (you go from vague to bad). Don’t get discouraged by these; finding your false assumptions is possibly the only way to really begin.

Despite loving his whole exploration of “mode,” I don’t think that means you have to neglect essay as “genre”; he says form/style don’t matter in “the best essay,” and I disagree, obviously. He has Darwin as the pinnacle example of an essay, and I’m really challenged by that (I definitely have to read it now). Is that an essay or a scientific paper, just captured in shortform non-fiction? He seems to imply that the essay is at its best a vehicle for discovery, as a mechanism to bring forth surprising, important, and useful ideas. From the creator of “make things people want,” this isn’t surprising. Even though a new theory of evolution had broad implications for society, I assume the paper itself is technical, intended for a scientific niche audience, which in my mind, makes it more like a scientific paper than an essay. An essay is something that is universal/general enough for the average person to read. An essay, I think, functions like an information transfer system between specialized facets of society; it’s about making your specific niche legible to all the other niches, and I don’t think that was the specific goal of Darwin's writing (even though it was inevitably understood by everyone, it wasn’t through the writing, but from the effects of the writing).

(Added: Another note on Graham’s notion of best as timelessness: he says that timeless esasys are the perennial insights that each generation can’t absob. This implies that the insight is never enough: even if you know something, there is often a lack of wisdom in applying it to your own circumstance. And so really, these unteachable lessons are ones that can only be obtained through personal experience. Does this point to the fact that all essays need to be personal? Maybe bland insights can’t be digested by a reader, but if they are integrated to vivid personal experience, experience vicariously, then might this actually be the best medium to transfer wisdom?)

This is a memo I wrote after a talk with Will at the diner, about startups vs. institutes, in the general vibe of Emerson (grandiosity, certainty, metaphorical lushness):

I want to understand the different range of “social organizations,” and so I’ll use the domain of writing to paint the differences between types.

The “institution” of writing is the centuries-old, intergenerational norms, traditions, and constraints that are inherent to practice, medium, and distribution. One does not simply “start” an institution; it is an abstract, ancient entity; an “institute,” on the other hand, is a concrete group with a specific purpose, aiming to steer or reform the behemothic institution. We are in a ruthless river of progress, and the cost of civilizational acceleration is the endless erosion of institutions, and so it’s the near-holy responsibility of each generation to build institutes that inject vitality into their dying fathers.

An institute is born from a “dream” in one man’s head, but they’re not on a “mission” until they step out of the stream of circumstance and act. An “institute” is not a planted flag from the fumes of excitement—I refer to a friend who, on an acid trip, claimed to have founded The United States of Brooklyn, right then and there—, but the ripcurrents created by decades of stubborn action. It is not a name nor brand, but the systematization of one man’s unreasonableness.

It all starts with a “project,” a spasm of effort, a groping forward to find leverage towards their purpose. The visionary will find projects drooling out of their mouth like the blood of life; many will fail, some will hurt, but once a cluster of projects start spiraling around a central spine, you have an “embryonic institute.” I use the word embryonic because institute mortality rates are high. It is far easier to start projects than to nurture them past infancy. The hallmark of an institute is stability through time. 5.4 years, I’d guess (+2,000 days, spanning 3 molts).

In the case of Essay Architecture, I am stretched across (6) verticals: a curriculum (the 24,000 word textbook), a school (the AI app), a library (the 100 essay archive), a club of shared practice (Essay Club), an economy (the $10k prize), and media (the anthology). In a single year I’ve planted these seeds, and you can see the buds poking through the soil. There is something happening, you can see, but it will not be a force of authority in the eyes of me or the world unless it all survives and feeds society through several winters.

An institute, then, in its dizzying scope, contains interconnected “objects”: (a) knowledge, (b) services, (c) events, (d) activities, (e) opportunities, (f) people, etc. It is a fractal version of society; it contains all its parts, but all dedicated towards a single thrust of mission. This is hard to maintain! So in comes the money.

The question is, how does the structure of the institute not get corrupted by the cannibalizing incentives of capitalism? How can you sustain the mission without it becoming a cog of the market, the mission reduced to a dress?

Unless an institute has an endowment, it needs a for-profit wing. A “startup” is about discovering new market opportunities, while a “company” is about operationalizing, scaling, and extracting from a known opportunity. Startups, companies, and institutes can all have “missions,” but only the institute is “mission-driven.” An institute will take money, but never compromises. If you cow to the market, a drip turns to a torrent, and the mission will be gutted, twisted, used as a narrative mask to help you lie to the world and yourself. It is a common and tempting line of logic to say, “once I make all the money, then I’ll do good.” Meta thinks that once it conquers the entire economy, it can finally focus on doing the good work of helping people “connect.”

The year one actions cannot be only tangentially tied to the mission; they need to be the mission itself. Building an enterprise-grade API for Grammarly and Brown will make me rich but tired; having spent my years spawning my anti-mission, the death of the essay, I would move on to some other project, maybe music.

When I look at all the writing technology startups, you can see how, in their first years, they’ve completely oriented towards business writing, towards the automating of prose, towards things that betray the ancient institute of writing. They either don’t get it or don’t care or just really need the money, but writers see their slogans of “helping writers write” as marketing drivel.

The insanity of a true institute is the stubbornness to put the mission before everything: before markets, before investors, before people, before ego, before legibility, before reason. This sacks your own speed, and is only fueled by heroic effort and the faith that, with time, it will find a real, timeless form.

The fruit of this insanity is trust: the various guilds of people that orbit an institute can sniff beyond the rhetoric and see what’s really driving its actions. If there is no track record of humility, or of “doing things that don’t scale,” or of “doing things without revenue potential,” or of “directing resources towards weird ideas because they advance the purpose,” then trust is lost, and all the mission-driven rhetoric is seen as the wolfish guile of someone who can no longer notice their own animotronic limbs and memes.

I believe the will, hope, and talent of an institute’s founder are the pre-requisite to birth a society-scale entity, but once you operate at abstract scales, architecture matters, extremely. Has Christ not been bastardized? Did the American experiment not get wrecked by the hyper-capitalistic invention of trains? Our very best religions and governments did not have the foresight or civic inventions to prevent them from getting sacked by barbarians and wolves. What I’m getting at is that we need some sort of 21st century constitution for institutes, an immune system to enable the virtue-driven founder to build something that has a chance to make it in an exponential landscape of virtueless technocapitalism.

I imagine it should look more like a loose collection of protocols than a single canon. For what it should contain, I can’t sketch right now, but I think it has something to do with mediating power, money, status, people, etc. My intuition is that the playbook is possibly the opposite of a startup.

The institute is the inversion of the startup. Where startups are designed to accrue all of the upside, an institute is sacrificial: it should be designed so that society gets the upside, even at its own peril. Really, it’s quite Christian. Of course, this shouldn’t prevent the founder of the institute from getting wealthy, but if the primary goal is personal wealth, then it’s not, definitionally, “mission-driven.” Instead of saying, “I need a $10 million valuation so I can open up $250,000 in grants for writers,” I want to say, “through paying writers $10 million, I will somehow make $500,000 a year for myself.” The idea is to become potentially wealthy through spearheading a radical mission, one that is worth it for itself—an adventure of a lifetime—, and one that is also, a magnet for capital.

This maybe gives some context to my goal for the next 1,000 days: “become financially independent through a mission-driven company and non-convergent artistic practice.”

To close with some specific examples, here are “acts of institute” (for Essay Architecture) that a startup would never make:

• No demographic optimization: The curriculum is not tailored for the biggest demographic (beginners). It starts at the edge of my knowledge (301), and then radiates in each direction (towards 501 and 101). Eventually, it will touch all demographics, so I need to start where my energy is, and never stop.
• Virtue-driven development: Even though people want the AI to write for them, and they want to use this for fiction and books and business memos, this is squarely an app to advance the genre of the essay, and it will never write for you. Even though more and more people will automate as AI gets better, this will be the go-to app for anyone who wants to engage with the process.
• Community voting: Any big decisions about the format of Essay Club are presented to the community as votes, which treats them like shareholders instead of customers. Of course, the founder won’t present options that contradict the mission, but instead of assuming which specific form is best, or choosing the one that is best for me, the community will sustain if it is co-shaped by them.
• Checks and balances: To promote the Essay Architecture tool most directly, I would have made the app the sole determinant of the prize winner, but instead 2/3 of the vote is determined by external judges. In some areas, my own perspective and taste is required, but it’s important to know when I need to systematically remove my own ego and preferences. An institute is not about scaling my taste, but in creating scalable systems that help achieve an ideal that I couldn’t reach on my own.
• Paying the public: At the start of 2026 (Q1), I want to crowdfund $100,000 for the next essay prize. I think this creates even more buzz and intrigue in the institute. It’s not at all what I would do if I were a startup: I’d be fundraising to build a team and scale the app. The goal is to create an ambitious cultural magnet that gets writers paid, while simultaneously catching the tailwinds so that I can get paid for my tool and curriculum.

Instead of spending 5 hours per day mad at trending social justice issues (20,000 hours per decade), I want to focus on building an institution for the essay. It’s a sort of illegible, seemingly irrelevant, idiosyncratic thing to do. But if it works, and if it somehow has any affect on how writing is taught in schools, and that improves the critical thinking of a generation, it will have way more influence than if I spent all that time protesting and howling for nothing. This just taps into a core belief of mine that the only way you can possibly help anyone outside of you and your immediate circle is to pick something dear to you and approach it with unreasonable fervor. If someone were to criticize me for ignoring a genocide, I’d say that all you can do is intensely dedicate your life to a single vector for multiple decades in the hope that you can tilt the scale away from next generation’s genocides.