Get Schooled: The Ultimate Guide to Michael Dean

Insights and essays from a sage of the craft

Jun 22, 2023

This is last of five essays I wrote during Write of Passage Cohort 10 (my Curation Assignment). It was originally published on my site, so you can also read it there.

He's a semantic savant, a lexical technophile, a feedback fanatic, The Clarity King. He's a sage of the craft. He's

Michael Dean

When I first found Michael's blog, I was lying on three inches of air inside a seven- by two-foot tent on a cold, rainy morning in Iceland. I flicked through every page of his site — every category of his blog, his latest logs, and his About page — drawn in by his playful, economic writing.

I remember binge-reading four or five essays and feeling a deep, cerebral connection. He was clearly curious, a proud polymath, and a self-proclaimed "niche-hobbyist." And, like me, he was an editor and a language-lover, despite not studying English. He studied architecture; I studied finance.

I felt an intense familiarity, but it wasn't because of what he wrote. It was because of how he wrote. Michael's voice resonated with the voice in my head, as if a samurai was dual-wielding drum sticks and intermittently striking two identical gongs. I felt like I could read behind his words — as if I knew which verb was in the first draft a sentence, before Michael had swapped it for one that was more apt. And I'd catch myself counting syllables and guessing at how many times he'd rewritten a paragraph to get it to flow with such a lilt. The way Michael thought about writing was the way I thought about it, and the more I read him, the more I wanted to write like him.

One of the essays I read that morning, wrapped in my sleeping bag, was "Jaywalking," from the "Auto-Fiction" section of Michael's site. This autobiographical, semi-true account of a morning in Midtown, Manhattan, is the kind of insight-dense, rhythmic prose that got me hooked on his writing:

I can’t comprehend the range of experience behind these swarms of people. I focus in on one person at a time, and visualize imaginary scenes from their life. Their first orgasm, the death of their parent, and their moments of boredom or addiction. Each moment is fabricated. It’s a caricature. It reveals my own judgment. But by visualizing fictional moments of strangers, I feel the depth and range of experience hidden behind the profanity of Times Square. It’s a lot to process. My mind is tingling, drowning in a surge of summoned empathy.

I pounce on every word Michael publishes, and I've done multiple deep dives into his archives. So, this is me sharing what I know. Below, you'll find a curated list of my favorite essays from Michael, categorized into three main areas of his writing: life as a modern writer, hallucinations and hypotheses about the future, and musings on the craft of writing.

Ding, Ding! Did you hear that? It's class time — time to get schooled on Michael, "The Dean."1

*Edward R. Rooney, Dean of Students, who resembles Michael in neither demeanor nor appearance –* Ferris Bueller's Day Off

Living Like a Modern Writer

Within the next decade or so, I expect Michael to have one of the most robust and compelling digital presences on the Internet. He hangs on the bleeding edge of new tech and immediately integrates it into his workflow, and that will serve him well. It will help him carve out his slice of the Internet and become immortal, which he's well on his way to doing.

Logloglog

This is Michael's stream-of-consciousness log. He records ideas as notes of prose then publishes them to his site in reverse-chronological order. There are some great nuggets in there for his readers, and they offer a great value to Michael, too: he remains in the habit of writing and publishing even between his long-from pieces. Logloglog would be a great habit for any writer to adopt, whether you publish the ideas or not (something I should try too).

Write for Your Grandkids

Michael riffs on the common advice to "write for one person," suggesting that you imagine your future grandkids rather than a caricature of your ideal reader. This approach engenders a new motivation for writing: write so that the present reverberates into the future — so that words, ideas, and stories connect ancestors with their descendants.

If I'm going to come up with a theoretical person to guide my writing, instead of inventing a cold stranger across the internet, they might as well be a future descendant of mine with a curiosity to learn about their past. It makes me wonder how a young person might evolve differently if they have access to unfiltered wisdom from the generations before them.

Substack or Bust

This essay is the reason I started a Substack. Michael makes a compelling, matter-of-fact argument for the merits of the platform, especially for its customization features and network effects. I bet Substack would have commissioned this piece, if Michael had pitched it.

Substack is evolving faster than I can update my model of it. It’s no longer just an ‘email newsletter’ platform. It’s the trifecta for online writers: email distribution, network effects, and a personal website. It’s an all-in-one solution.

Hallucinations and Hypotheses

Michael has a finger firmly on the pulse of the present, helping his readers predict and prepare for the next technological and cultural revolutions. Many of his best insights take this form: hallucinations and hypotheses — compelling arguments and vivid portrayals of realities we may soon be living. (For one, he's bullish on teleportation. The first version of it would be a combination of AR and VR that lets people share a hybrid, physical-digital space — like a Jedi Council meeting.)

The 1,000-Day Molt: How to Make Decisions Like an Insect

We don't have to outgrow ourselves if we don't want to. We can stay in the same shell and avoid the pains that come with psychological evolution. But maybe, instead, we should put our psyche on a molting schedule, like a praying mantis. Maybe we should schedule consistent system-reboots throughout our lives. Michael suggests exactly that, and that the ideal interval may be 1,000 days.

The psyche can outgrow itself, but it prefers not to. We’d rather feel busy, make tweaks, and drown in distractions than make the hard-to-swallow changes that have impact on our lives. The pain of metamorphosis is real, so we justify our past decisions to feel good about the shell we’re in. The ego’s one job is to preserve identity. It’s an anti-molt machine.

Margin Matchmaker

AI has writers cowering in corners or scratching the sides of their heads with the backs of ball-point pens, trying to figure out how to remain relevant. But writers are concerned about the wrong things. We shouldn't be using AI for creation but for curation. There's an approaching future where an AI will sit in the background of your word processor and, as you write, feed you relevant excerpts from your unread library and from all the notes you've ever taken. Rather than your Cursor Cavalryman, AI could serve as your Margin Matchmaker.

Resurrections On Demand: Put LSD Back in the Communion Wine

Yeah, you read that subtitle correctly. In this saga-of-an-essay, Michael traces the origins of Christian rituals back to the Eleusinian Mysteries of Greece, which he dubs "state-sponsored peak experiences." Those Greek mysteries were strong cultural events that united a people around shared beliefs, and they were likely aided by psychedelic hallucinations. So, Michael asks, "Could psychedelics be the missing ingredient in Christian ritual?"

Meta-Musings

Michael must have some version of synesthesia, where whatever he reads is simultaneously rendered as a mental model in 3-D space. He can reverse-engineer a detailed blueprint for any essay and creates revelatory visuals that break down fluid works of art into their very building blocks. He'll deconstruct paragraphs, chart the beat of a sentence by counting its syllables, and imitate his favorite writers. There's so much to learn from from Michael's musings on the craft. Below are some highlights and key insights.

My main take-aways from Michael's meta–musings have been about being playful and writing for rhythm. If you're enjoying the word choice or the flow of this essay, you can thank Michael Dean. I'm channeling him. He's inspired me to break free from my default vocabulary and to edit paragraphs for their meter as much as their meaning.

Typewriter Essays

What better medium is there for writing about writing than the clanking typebars of a 1950s typewriter? These mini-essays are home to some of my favorite lines of prose from Michael, but he's only published three to his site. (So, go comment on this post and ask him to publish more, please!)

The first mini-essay is ultra-meta; it's not just an essay about writing but an essay about writing on a typewriter, written on a typewriter:

This $525 Etsy purchase from Tony’s Typewriters is more than the splurge of a niche-hobbyist looking for another distraction. Nostalgia is just the icing. The limitations of an analog typewriter call for a stretching of the creative process. Word processors enable chicken-scratch and the infinite pondering of darlings that must be killed. A typewriter promotes a series of re-writes. This is take seven. Like a band rehearsing on loop, each march forward generates accidents and epiphanies that get carried from cut to cut.

Then, there's this potent, timely reflection on ChatGPT's colonization of the zeitgeist:

In your skull are constellations of scars and dreams, galaxies of training data, more than any algorithm pimp can conceive. I don’t care how many volumes of lore GPT-3 binged from the New York Public Library. I don’t care that AI is swallowing the Internet to the bone. Your stories are locked within you. Those family dinners, those closed door conversations with forgotten lovers, those twilight strolls in chaos town. All that material sleeps within you, waiting, yearning to erupt… And you’d rather jump into the LEX AI app? You’d rather summon the banter of a million idiots than take a straight shot from the source? Don’t ignore the mouthless ghosts within you. TUNE IN.

Wallacisms: The Art of Memorable Writing

David Foster Wallace opens Consider the Lobster with an essay called "Big Red Son," his account of an adult film conference in Las Vegas. Michael read the 50-page essay three times so that we may benefit from six clear and concise take-aways about how you can make your writing more memorable, by making unlikely associations.

An example: Unpack the meaning behind words. Here's the line from DFW's essay as evidence for this tactic:

But of course we should keep in mind that vulgar has many dictionary definitions and that only a couple of these have to do w/ lewdness or bad taste. At root, vulgar just means popular on mass scale. It is the semantic opposite of pretentious or snobby.

Beeple's Mosaic

Beeple, the digital artist who sold a single NFT for $69 million, created an art piece every day for nearly 14 years. In his story is a lesson about how quantity leads to quality and how time constraints can be liberating (and lucrative).

If your publishing routine is like a fail-proof cadence of the universe, you will become a force of nature.

Our Meet-Cute Story

Last summer, on that cold, rainy morning in Iceland, I didn't just decide that I wanted to write like Michael. I decided that I wanted to work with him. I wanted to join the writing community he was helping build: Write of Passage. So, a few months later, I sent him a cold email, then followed up with another. Eventually, we had phone call and nerded out about editing for close to an hour. He referred me to a job. I applied, and I got it!

Michael is the Editor-in-Chief at Write of Passage, and I am the Editorial Director.

Within six months of discovering Michael's blog, he and I had met for dinner and a movie in New York City.2 And now, we swap drafts and edit each other's essays. (Yes, I'm open to inquiries about the film rights to our meet-cute story.)

But don’t discount my praise of his work on account of a bias. Before Michael was my friend and co-worker, he was my favorite writer on the Internet.

And he still is.

The last thing I'll say is to The Dean himself. Michael, you've got it — the talent, the passion, the insights, the typewriter. Just keep going. I have no doubt that the rest will come. Thank you for sharing your words.

Springboard:

Who in your life does work you admire? Do they know how much you appreciate what they do?