michael-dean-k/

What is the texture of a day these days? As our life’s inevitably mutate across the decades, we never stop changing, our condition never stops changing: projects die, people die, we learn to look people in the eye, we move, we read and marry and birth. We lose grip of our iterating selves, compress them down to caricatures, characters who also destabilize with time, slightly warping each time we retrieve them from memory; my post-college self is a copy of a copy of a copy, that original self in full-fidelity, irretrievable. Unless, I wrote. Which I didn’t. Will my current self be an equal mystery? Will I know what it was like to get out of bed in July of 2026?

What even is my current self? As fresh and live as it is, it too is ineffable, shaped by cliches that won’t hold if interrogated. It is too dynamic, too complex and thousand-headed to contain in one photograph, or mere words. It takes real effort and skill to see clearly into your own situation, to capture the right essence in the right words. Perspicacity is a depleting resource. If your life is “busy,” as most are, as most new parents definitely are, then the unbroken time to yourself gets thinner and thinner. Those two hours in the morning before the day escapes is met with decision paralysis. I am behind on countless threads; which thing do I save from ruin? Or, do you I use that time to reflect and write, like this, and let everything continue to burn, instead of finding some consolation in it all?

I’m using dramatic words here for what is actually a special and wonderful time. I feel bad to have not put proper words to my love for my daughter. That will come. I’ve had in mind a long letter I want to write her in her first year, but we’re already half way through and nothing is penned. Naturally, I’ve had so little bandwidth this week to write anything. Between consulting work, maintaining Essay Club, watching my daughter full-time, and reading the Odyssey, (all things I cherish) there are little hours left to tend to my hydra of interest and ideas, to keep up with basic responsibilities, to be a good friend and husband, to unpack from New Hampshire, etc.

The reason I wrote this is because I woke up at 6:45 am with a familiar texture, a feeling I’ve been waking up with but not naming, a feeling endemic to this present phase. It’s a guilt for not waking up two hours earlier. Now it’s 7am, and I know not exactly when the day will start, when obligations kick in, when I will have to go to Target to buy children’s Benadryl, more formula, my nephew’s birthday present, etc. It’s this subtle feeling of starting with defeat, which can’t help but color and tamper my energy for the day. I yearn for a 15-hour chunk of focus, just for a single day, to blitz through and catch up on everything, but that then creates a load on my wife. I am becoming more selfless and yet also yearn for selfishness.

The other possibility here is that I’m continuing to fail at understanding prioritization. I just found an essay competition for $50,000, on defining the “new axial age” we are entering. I am intrigued, but deciding to do that would sacrifice everything else. The decision to read the Odyssey already led to a strange kind of obsession that has eclipsed so much else in this last week. I feel guilty for not directing all available attention to my business; I currently make a livable “salary” between consulting and my Essay Architecture project, and while I could just maintain what I have and be “fine,” there is the financial pressure to grow my business around 5-10x in the next 3 years to build the life we envision for our family (without growing it, a simple hiccup could financially destabilize the whole project and kill years of momentum, forcing me to get a regular job). Yet, prioritizing only professional strains feels like creative stasis, the death of mind and spirit, which is probably a normal thing that all adults have to play out. I resist it. I resist it like I resist death, probably since that near-death freak car accident, when I emerged from flipped metal, completely untouched, with a new commitment to take risks (there’s a chance the two are unrelated, but that’s how I mythologized it to myself). I am resisting it in strange ways, which yesterday took the form of rewriting the Odyssey with an opening scene where the cyclops gets castrated.

I still sit cross-legged in bed, writing this, which satisfies my “daily post” obligation that has withered. I want to change my mind before my feet hit the floor. Similar to how the first sentence of an essay sets you in a direction which you cannot retreat from (Didion), so too do your first steps into the day, determine the unfolding of that entire day (the proverbial “right side of the bed”). I know the wisdom I need, I’ve written about it at length, but it’s so easy to forget, to bring the right ideas to the right moment (maybe I need a hypnomnemata). But now I’m seeing a fuzzy outline of what I should remember: escape time, escape chronos (chronological time), and enter kairos. This is my version of “get out of your head.” I find that it’s not my head that traps me, but time itself. I am often trapped in recountings and projections, in personal and societal abstractions, and I derive identity from them without realizing, calcifying into stoned eyes that wake up with me. All issues point back to some version of being stuck in the illusion of time. And so really, my issue is that I’m not “praying” to it; I’m not “meditating” to it; both those terms aren’t quite right; what I mean is that I am not holding that idea freshly in my mind, repeating it and refocusing it throughout the day, to the extent that it shapes my perception. All moods are downstream of past frames of attention. And so this rut I feel is simply the product of not being attentive of the right ideas in the prior days; a forgivable offense when still synthesizing the shards of a new era.

I look to my left and notice this beige mat I bought in Portland, Oregon in 2015. It’s an 18” carpeted square composed of five squares, one in the middle, and then a single line that interlocks and weaves through the middle, creating the illusion of four corned squares. It’s a short step away from my bed. The goal is to wake up, stand on, and meditate on. I forget that I put this here, to remind me to start the day right. I’ve ignored it for the last 200 days. And so despite the chaos and business, perhaps the only thing you can do is take seriously a few simple rituals. And now the babe cries.

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 pray 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 an ARR target 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.

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. But this is maybe a 3rd of 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 in the first place, and so this whole reading/writing for leisure thing is a healthy counter-balance.

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.