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Michael Dean

Architect turned writer.

Director of Content @ Write of Passage. Edited over 500 essays last year. My personal writing aspirations: polymathic scope, battle-tested prose, untethered rants, blitz imagery.

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Featured Posts

⚡️ 85 thoughts from May'22

I need to decide how I'll distribute my logs through email. The simple route is 3-5 per week. But there's a certain wonder in peaking into someone's unedited mosaic of thought. It's hardcore, but it's distinct. It stands out from the wave of filtered, curated tidbits.

🔎 Wallacisms: The Art of Writing Memorable Observations

"Big Red Son," is an outrageous David Foster Wallace essay about a 1998 adult film conference. By dissecting it, we'll learn some (non-vulgar) tricks to help our writing jump through the page. Use relatable metaphors. Make unlikely associations. Look behind the scenes.

📩 One-click Distribution

Hello world! This is the inaugural edition of Dean's List. I've decided to transplant both my website and newsletter into Ghost (this will surprise those who know me as "the Notion guy.") Sounds drastic. It is, but let me explain.

✉️ Newsletter Junkyard

We're in a newsletter arms-race. What happens when everyone has one and they all sound the same? Overwhelm, skimming, and email fatigue. The old tricks around niches & weekly streaks are becoming predictable. What makes a newsletter exciting to open each time?

🚶‍♂️Jaywalking

I went into the city on Saturday to meet up with Isabel in person for the first time. On a walk from Penn Station to Bryant Park, I decided to write down everything I experienced. Eight blocks north, and then a few more east. It’s a great exercise to practice, “placemaking.”

Recent Posts

🎷 What's in a Kerouac sentence?

Jack Kerouac was a famous writer from 1950's, but he referred to his own practice as "sketching." Like a painter, he'd look around slowly to soak in and reflect on the details. As images and memories bubbled up, he'd scribble them into flowery, never-ending sentences. When Kerouac writes, it feels

⛳️ Is Mini Golf better in VR?

For $16, my wife and I got access to two rubber golf clubs, neon balls, and a sequence of 18 amoebic, turfed-up, basically flat holes along the side of Big Finger Boulevard. The stakes were high: loser buys lunch. I kept score with one of those miniature red pencils that

✏ When to Get Feedback?

“At what point should I share my essay with editors? Should I ask for feedback as soon as possible, or should I wait until it’s a coherent draft?” Both! The biggest misconception about feedback is that it’s a singular event. You don’t have to write in isolation