Dawn of a listicle (Dean's List #1)
3 side effects of publishing, 11 confessions from a typewriter, and 10 logs to prove I’m still a multidimensional human before I start marketing the benefits of my paid offerings!
I’d like to quit pussyfooting and kick this Leap Year off by living up to my name: Dean’s List. “Where’s the list?” This question haunted me through the post-Christmas silence. In 2023 I published 23 essays, over 2,000 logs, but 0 lists; I’m a fraud who doesn’t know the meaning of my own name. My publication title is ambiguous; I’m not even sure what I mean by “list.” Is it simply the CSV file of my subscribers? The yet-to-be VIP tier? Is it a nod to the judgments of an academic honcho who holds a high bar? Am I destined to become the un-appointed dean of Substack, crafting ranked lists of writers they feature on Reads, holding them accountable to their promise of quality?
I’d like to put speculation to rest; this newsletter is going high-concept…
Dean’s List is now a listicle.
There’s a cosmic irony here; I set out to create timeless essays that would one day get featured in anthologies curated by Phillip Lopate, but hidden in my name is the medium known for clickbait, SEO-filler, and quizzes like “10 questions to know if your OCD is life-threatening.” I feel the call to hijack the listicle and use it to structure my creative spatters.
Plus, a monthly list is a functional move that aligns with an announcement I’m eager to share:
I’m releasing a (text)book called Essay Architecture. Instead of converging on a final form, it will be an always evolving framework of writing theory that grows with me on Substack. Starting today, paid subscribers will get new chapters, breakdowns of classic essays, Miro videos, and a glimpse into my private world of analog practice. To respect your attention, these new streams will be mostly ghost-posted: they won’t hit your inbox unless you opt-in, they’ll be curated in a monthly list–Dean’s List! (Existential crisis resolved.)
I’m grateful you’re here, and find it surreal and fulfilling to have many of you read and respond to my essays. I’m starting my 4th year of writing online, and it’s the year I make it my main thing. I consider myself fortunate to even have a chance to make an independent living writing, reading, editing, and teaching the architecture of essays.
It’s weird and significant to me that my origin point is my destination. My first published essay—Studio Culture, in July of 2020—was about what writers could learn from architecture school. Half-a-million words later, it’s now the shape of my future.
I’ll be sharing more specifics on paid subscriptions in my next post, but here’s the gist.
For $10/month (or $100 a year), you’ll get Essay Architecture, and everything in the Craft and Analog sections of my site.
For $250/year, you’ll get a Calendly link to get (live) flash feedback from me or someone in the Dean’s List community, whenever you need it.
I’m also looking to work closely with ~10 writers in 2024 to shape essays at the edge of our shared ability.
The introduction to my textbook comes out soon, and I’m offering a 20% discount if you sign up before it launches.
Save $20, support the arts, and un-fuck your first draft.
Now let’s do the listicle-from-hell thing. I’ll reflect on the ripples of some 2023 essays, introduce you to my typewriter experiment, and share 10 logs worth reading from December 2023.
3 unexpected side effects of spending too much time on long-form essays that have nothing to do with metrics (or, the consolation prizes for someone who sucks at self-promotion)
Exactly a year ago I shifted my whole website to Substack. Before that I was posting essays into the void of Squarespace, Notion, and Ghost with basically zero response, recognition, or growth. In 2023 I grew from 216 subscribers to 878. Even though I get completely absorbed in the refinement process, spend basically zero time promoting my work after I’ve essentially slaved over it, and then immediately move to a different rabbit hole, the Substack network must have given me the minimum viable juice to gain some traction.
I’d like to learn to love promoting my work. But what’s actually more amazing to me is the tangible serendipity that came into my life without having a basic handle on distribution. By existing online and trying to do the best work I possibly can, things seem to happen.
So here’s a collection of essays from 2023. Instead of focusing on the subject matter or the stats, I want to share the unexpected side effects that came from chasing great work instead of metrics. I haven’t really talked about this dimension of “opportunity,” but the point is to maybe inspire you to pursue a slower cadence, get an extra re-write in, or try something that pushes you out of your comfort zone.
Burn Down the Stage
When Facebook hit its viral moment in 2006 with the introduction of the News Feed, American Idol was the #1 show in the country and had 3x the “user base.” Now, every major platform we have, without exception, is structured like a talent show: the owners create a digital stage (a vacuum for fame) where a mass of lurkers vote to determine the fate of disposable idols.
I found the others— Just as soon as I figured out Twitter growth, I completely disappeared from the Internet and spent 50 hours in isolation working on Burn Down the Stage, shifting through 8 versions, spending a lot of time researching. I had serious tunnel vision. At a meetup someone asked me, “what do you write about?” and I just said, “American Idol.” When I first published it was anti-climactic, but over the weeks I started to hear from people in the social media counter-culture. I was emailed by writers I admire, got invited to meet with a NYC founder who is building a new feed-architecture, and got published in a physical zine. I’d been ranting about this idea for ~5 years to friends and family, but writing about it put me in contact with the others who were doing something about it.
Lucy in the Sky of Large Language Models
Technology is putting music through a process of “oozification,” a phrase coined by Venkatesh Rao. He says that technology causes stable forms to dissolve into miniature fragments that can be recombined in infinitely new ways. This challenges the things we once held sacred. The song, the catalog, and the band itself, each defined by its boundaries, its rules, and its scarcity, are all about to get oozy. This sounds scary and unfamiliar, but it’s already happened. The Grateful Dead were the “band of ooze.”
I was mentioned on Ribbonfarm— Without realizing, I published Lucy in the Sky of Large Language Models on the same day the Beatles released their AI-produced song: Now and Then. It was bizarre timing, especially since my stretch goal for Write of Passage was to meet Paul McCartney. I imagine I could’ve gone viral if I promoted myself, and naturally I froze. When I saw another AI Beatles essay get featured on Substack Reads, it confirmed that I fumbled. But weeks later, I was reading Oozy Intelligence in Slow Time, an article on Ribbonfarm by Venkatesh Rao—who I think is one of the best sense-makers of our time—and unexpectedly saw my essay linked at the bottom. I forgot I tagged him. It’s a reminder for me to not only write from experience, but to link my ideas into the conceptual currents around me. My essay wasn’t seen by a 100,000 people, but it was seen by a specific person I have extreme respect for.
The First Online Writer
Online writing today is often presented as a form of entrepreneurship: focus on a single topic (no range), for a mass-market audience (no depth), and be careful with off-brand details (no glimpse into the logs of your life). Justin Hall-who started in 1994-embodied the opposite ethos: write about a polymathic range of topics, at a depth that most people would never consider making public, and include detailed logs of your day-by-day experiences.
I connected with my hero from Internet history— My whole logging practice started in 2021 after I came across links.net, a website started by Justin Hall in 1994. Walter Isaacson wrote about him, and Justin even made his own 40-minute documentary, Overshare, but I felt compelled to write my version of his story from the angle that inspired me.
In September I spent an incalculable amount of time navigating his HTML maze, reading every single DAZE entry from his 1996 logs (probably over 100,000 words). It was more research than I’ve ever done for an essay. I ended up with The First Online Writer, a 7,900 word curation piece with 128 links.
On a call with my writing group, we were reflecting on how we’d each share our monthly essay with the world. Instead of trying to promote this, I said, “the ultimate win would be if I sent this to Justin and he started writing again.” He hasn’t been posting much since 2005, but I found his email on his website. I wrote him a fairly long message in response to something he posted in 1996–28 years ago!–and linked to my essay.
Two weeks later, he wrote back and was extremely kind. I checked his website on New Years Eve, and he said he’s itching to write in 2024. I have no idea if I had any influence on this, but either way it’s a reminder to me that an essay doesn’t have to be written for the world, it could be done just to thank one person.
11 things I may one day regret sharing, but by putting them behind a paywall I’m semi-confident I won’t get in too much trouble
Analog habits are refreshing. I’ve been writing one-page essays each morning on my typewriter from 1956. Unlike my long-form pieces that are slow and structural, these are fast and unhinged. It’s my shadow practice. It sharpens my prose and it’s a space to unpack anxieties, dreams, memories, theories, and elf languages without much of a filter. For that reason, I want as few people to see these as possible. By putting these on a paid tier, it means I know I’m speaking to people who support me and are curious to learn how writers practice outside of publishing.
Streams of consciousness for $0.22 cents a day
Dec 31st — one year I’ll piss my diaper at the center of the world as they reset the calendar
Dec 30th — my made-up word for 2024
Dec 29th — an ode to CansaFis Foote
Dec 28th — 98% of my readers…
Dec 27th — tring doobayonkie foofa foofa
Dec 26th — one-page annual review
Dec 24th — how to rewrite Infinite Jest lol
Dec 22nd — the geometry of writer’s block
Dec 21st — brief excursions in the dark arts
Dec 19th — when your destiny is a listicle
Dec 18th — heart surgery & xmas tree farmers
All my typewriting experiments can be found in the new Analog section. I’ll continue to curate these in Dean’s List, but if you want them in real-time you can opt-in here: manage your subscription.
10 logs on trash content, prompting the subconscious, editing, leap years, leap seconds, Christmas trees, career legibility at holiday parties, patience, marketing, Substack economics, and calligraphy-based New Year’s Eve celebrations.
In each edition of Dean’s List,
I’ll share some top logs from last month.
Scenes from X | Dec 13th, 6:04 pm: 1) A dead body sliding down Mount Everest, 2) the Microsoft Excel Championship tournament in Las Vegas (won by Andrew the Annihilator 3 years in a row). 3) A Congressman has cloned himself into a voice-powered AI so he can personally call each voter and have a 1:1 chat with them.
Prompting and psychedelics | Dec 18th, 7:34 am: Terence McKenna implied that he can "prompt his subconscious" during heroic-dose psilocybin trips. "Show me Art Deco," and then thousands of objects with that vernacular appear. He can cycle through aesthetic epochs. Then he says, "surprise me," to find objects that are otherworldly. There's a feeling of "my god, if I could just take a hold of this," but it's all lodged within the trip. Then he says, '"show me what you really are," and then the room darkens and everything turns ominous and he says, "alright, back to the dancing squirrels and carpet patterns." It just points to the almost identical nature between the deep reservoirs of machine intelligence and the unconscious, matched by the tiny human's ability to use small phrases to "refocus the camera," on particular regions. The implication is that everything we've ever seen gets stored and logged away into some incomprehensible system, only retrievable again through when the visual centers of the imagination are fired up: dreams, drugs, and maybe death.
The simplest way to not hate re-drafting | Dec 21, 5:55 pm: The secret hope that "this draft is it" will get you to cling. Don’t confuse a discovery medium for a final artifact. Know when a draft is a draft.
Leap years and leap seconds | Dec 22, 11:21 am: I have gone down a rabbit hole researching leap years. Did you know there are leap seconds too? The whole reason we have these units of time is to coordinate our abstract calendars with absolute solar time. Despite our insane system, we're still 26 seconds off per year, meaning this subtle solar drift over 600,000 years will result in a "solstice reversal."
Rockefeller center tree | Dec 22, 5:29 pm: The grower of the Rockefeller Center Tree doesn't get paid. Despite losing a Norway Spruce with a market value of over $1,000, the monetary value is less than the honor of being scouted and selected. It's not like this carries any kind of prestige or credential for future selections, it's more like the rare cultural honor of being the main benefactor of Christmas; you get to sacrifice a living thing on your property for the whole morale of the country.
When your relatives have no idea what online writing is | Dec 28, 8:22 pm: In those holiday exchanges with semi-distant relatives, where you're crammed in the corner of a loud kitchen–probably blocking your aunt–and you know you only have 10 back-and-forths max to fill each other in on the last year's worth of 526,000+ hours of complex human experience, there's a tragic and comic act of compression that takes place. "How's that architecture virtual reality thing, Chris?" First off, that's the name of my very-similar-looking brother, and second, I realize I've done a very bad job updating my blood-kin on my molts. "Oh actually I write essays on the Internet now." I get that familiar what-the-fuck-are-you-talking-about smile I also get from dentists, gym trainers, Uber drivers, and other acquaintance who rightfully ask, "how's work?" I've learned to accept the illegibility that comes with freedom.
The slow lane of craft | Dec 29, 2:26 pm: Internet time is measured in hours and days, and so the solutions for transformation (more creative, more productive, more fit), are presented in terms of weeks. Truth is, personal evolution takes years and decades. It's a time scale that extremely online people can't process. The web itself has only been around 30 years, still a decade shorter than Rick Ruben's whole career. Young and restless creators should shift gears, see the long game, and exist in an entirely different lane without disappearing completely. If I had a vulturic mind, I'd say it's an "arbitrage opportunity," but the whole point is that the lane of mastery is about intense intrinsic focus, and strategy gets replaced with unpredictable opportunities that emerge because of the strange lens you've cultivated.
I’ve been thinking a lot about “marketing for artists” | Dec 31, 5:01 pm: I'm skeptical that the customer first mindset of high-growth venture-backed startups entirely translates to creators. The fragile psyche of an artist is very different than that of a Delaware C-Corp. As an artist, it makes more sense to get into the infinite game of craft, follow your own intuition, be online, and see how to make your process valuable to your audience. At a certain velocity, this artist becomes an unmistakable force, and they can get by on the patronage model. Artists make things because there's a mysterious pipeline of visions filling their head and they go insane if they don't get it out. Without making things, I'd be restless and aimless.
I spend $59/month on Substack | Dec 31, 5:48 pm: 2023 was a big year for Substack, and I've noticed more writers going paid. I'm currently paying $59/month for 9 writers; if a good heuristic is to invest 2% of your expenses to artists you enjoy, then I'm under-paying. Before October, I paid $0/month for 0 writers. This is the norm. There's a certain flip where you go from, "I don't know why I'd pay for anything since there's infinite content," to, "a healthy information diet is crucial, and if I don't pay for this, it risks disappearing."
Handwriting and calligraphy on New Year Eve | Dec 31, 11:30 pm: My New Year's Eve plans got canceled (COVID/flu), and so my wife and I found ourselves watching calligraphy and handwriting videos (YouTube algo). I've put basically no thought into this in the last 25 years. My mode of handwriting has always been fast. Get the thought down. But my experience with a typewriter got me to see the value of slower transmission; what if I wrote slow too? I ended up writing out 10-11 pages by hand. My attention would shift between shaping letters, watching the grid, minding spacing, seeing the overall page, and the thought itself. Sometimes elements would blend together in synthesis. I could definitely see this leading to some mental rewiring.
Let’s riff:
What are you thinking re: cadences in the new year? (weekly/monthly, essay/log, blast/ghost)
Any stories of serendipity from publishing last year?
Share your worst listicles (looking for inspiration).
If you’re a champion of progress and would like to get involved in an “ABOLISH LEAP YEAR BY 2035” movement, reach out at michael@michaeldean.site.
Mike, I'm so glad you are leaning into the paid tier. You've provided tons of value. And your ability to deconstruct and edit essays is prodigious. It only serves right.
I'm also very happy to see the small wins from your pieces. Self-promotion is a challenge for me as well, but I'm trying to lean on the wisdom from The Mucha Method little by little, day by day.
Easiest subscription upgrade of my life.
This is awesome man. Excited for you.