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We're in a newsletter arms-race. What happens when everyone has one and they all sound the same? Overwhelm, skimming, and email fatigue. What makes a newsletter exciting to open each time?
I’ll start my first edition with a confession.
If you have a newsletter that I’ve subscribed to, I most likely don’t read it. It’s nothing personal. My inbox in 2021 was a cluster-fuck, so I auto-routed all my subscriptions into aggressively named folders, like: “Hucksters,” “Robots,” and ”Slang Parrots.” Most of the mail in here deserves to rot for ten eternities in a server in Colorado.
But there is one folder that I hold in higher regard than the others: The “Newsletter Junkyard.” This is the folder where all my Internet friends are trapped. One day I’ll make the time for it, because some seriously cool people live in there. But for now, my inbox is as minimal as it gets, and I wake up each morning into Cal Newport’s wet dream.
The first edition of my newsletter opens with a paradox:
Why start a newsletter if I don’t even read them?
I believe in the power of writers using email, but we’re caught in a newsletter arms-race. The game has changed— it’s crowded. The go-to strategy has been to pin down a niche with a weekly cadence. But what happens when everyone does this? I’ll kick off this edition with my observations as a reader of the newsletter phenomenon.
After I’m done roasting my Internet friends (with love), I’ll share the strategy I plan to follow as a writer. My question is simple: what would I want to personally receive in my inbox? I’ll walk you through my line of thinking, and the risky implications. My conclusion: I want to write a newsletter that foams at the mouth.
Email can be a tidal wave if you’re not careful. It’s hard to maintain a sane inbox when you dive face-first into Internet communities. Almost anyone you meet online has a newsletter these days. (Do you even remember how you got on my email list?)
Unchecked curiosity leads to commitment, in Bulk. Before you know it you’ve got a three-digit subscription list and a fleet of Substack mailmen trying to cram into a single-frame door at the same time.
Given my current bandwidth, I realistically have room for two newsletters in my life. Three tops. But unsubscribing from people I see on the regular is rude, so to hell with ranking my friends— everybody goes into the Newsletter Junkyard by default.
What happens when I meet new people I want to keep up with? Well, after I subscribe, I hunt down the confirmation email like a model citizen, and then immediately funnel all future correspondence down into the Rancor Dungeon. There are no words to properly explain the serenity of a virgin inbox.
One day I’ll change. One day I’ll get my life together and turn my Newsletter Junkyard into a blossoming oasis of Internet ecstasy. I’ll skip church, and block out 3 hours each Sunday morning to plunge into a renamed folder called “Newsletter Heaven.” To the sound of birds and the scent of morning coffee, I’ll reply– to everyone! I’ll fulfill the social contract inherent to my subscription. My conscience will be clear; my after-life, redeemed.
Realistically though, the only chance I have to peek into the Newsletter Junkyard is when I’m taking a shit.
Why did my once-favorite newsletters turn sour?
Why do I skim and archive every week without fully reading?
Why have I banished newsletters to the peripheries of my life?
My theory: when readers quickly recognize patterns, they become numb.
Most newsletters I read have weekly cadences and stick to their niche. After ~30 days, I know what to expect. Many regard this as a good thing. I’m not so sure. In the next two sections I’ll unpack the dark side of cadences and niches in detail.
What are the negative effects of consistency?
1) Weekly cadences lead to “tolerance”
When you get a repeated dose of the same thing (beer, cat memes, heroin), you build a tolerance. You need a higher dose to reach the initial shock of wonder. When a newsletter comes the same day every week– with the same title, template, tone, and topic– you know what to expect. The more editions sent, the less urgency to read it:
“Look, another edition of Fuck-My-Life Fridays— I can’t open this because it’s April 8th and I literally haven’t started my taxes yet, but I probably won’t miss much if I just catch it next week.”
Consistency is useful for writers, but it can have a negative effect on readers: predictability. We should keep our audience on their toes. As soon as they recognize a pattern, they tune it out. It becomes a background process. It loses its magic.
Here’s an example: in an alternate reality where Christmas occurs every Thursday, all gifts come in identical boxes, and each week you get a fortune cookie, two lottery tickets, and three bags of Crunch bars, I’m pretty sure you’d break the habit of throwing yourself down the stairs to check what you got.
We need surprise. The behavioral psychologist and OG-dog-whisperer, B.F. Skinner, coined the term “variable rewards”— let’s use them. We need to breach our reader’s expectations. Otherwise, each edition of our newsletter becomes optional, landing straight in the Junkyard.
Just because we can use robots to automate the jobs of a thousand messenger pigeons, doesn’t mean we should deliver writing like a robot. Switch it up. Break your streak. Send something when you have something worth saying.
2) Niches lose their luster
The zeitgeist of the Creator Economy is simple: optimize a narrow value-proposition based on market analytics, until you niche down so far that you’re recording high-quality ASMR videos of yourself eating lobsters with a YouTube audience of 3.1 million followers. Product-market fit. A niche newsletter can seize attention and grow incredibly fast, but like a one-trick pony, they are (by definition)— predictable.
A newsletter with a restrictive niche is potentially a lose-lose— for both the reader and the writer. For the reader, it’s predictable— the patterns are clear and it can quickly lose its luster. For the writer, a niche can become a prison. Imagine if you built an audience around the premise of lobster “mukbang” (a Korean phrase for eating on camera). Out of your full pantheon of interests, you now have the expectation to somehow tie everything back to lobsters.
The faulty premise of the Creator Economy is the need to filter yourself and provide intentional value for a faceless, obscure, but significant corner of the Web. This thinking is clear in Gary Vaynerchuk’s mantra: “Jab, jab, jab, right hook!” In English, this translates to: numb your readers with value before you punch them in the face with a product offering.
Now don’t get me wrong, audience building is no sin. I’d love to make it. I’d love 9,010 subscribers and a plaque that says, “you’ve achieved low-key Internet fame without Brittney-Spears-grade psychological damage.” I just think we over-index on the need to cater to social markets. This may be the fastest way to build an audience, but it’s not the only way.
The best case scenario is a win-win. Writers can have the freedom to explore, while also providing something that is valuable, engaging, and unpredictable for the reader. These audiences are slower to build, but they’ll follow you down any road you go.
So don’t give me value, give me a secret glimpse into your life and mind. Let me into your fan club. I give you permission to rant, to rave, and to confess. I want vulnerability. I want a pulse. That’s where the real “value” lies. If every newsletter gave me a behind-the-scenes glimpse of its author, then the Newsletter Junkyard wouldn’t exist.
The goal with Dean’s List is to put out good, but unpredictable writing— so you have a reason to open it when it lands in your inbox.
Each edition will be a curveball— a plot twist— a chocolate in Gump’s box. I want this newsletter to dance between humor and horror, irreverence and beauty, truth and fiction. One edition will make you spit out your coffee, another will give you the chills. Sometimes it’ll come on a Sunday. Sometimes every day. Sometimes it won’t come at all.
Dean’s List will rant and rave about the Great Online Game— about VR, MarioKart, and shitcoins— sex, nukes, and rock-and-roll— drugs and the origins of Christianity— neighbors and pets, apples and oranges— the interior of Will Mannon’s apartment— run-on sentences, rumors, and possibly, writing.
I want a newsletter that shows you the skeletons under the bed. I want a newsletter that introduces you to my wife and dog. I want a newsletter that opens the curtains of the Universe.
Like a chameleon, this newsletter is a shape-shifter: it warps its face, shifts its voice, contorts its body, with an untethered gaze. Always hungry, always rigorous, but unhinged from identity. Sometimes this newsletter will come from Michael Dean, other days, Delirious Dean.
But most of all, I want a newsletter that scares the living shit out of me. If I’m not nervous to publish an edition, that means it isn’t worth your time to read. I used to cower at this fear. I still do. But now I realize it’s the thing to chase. The invisible fear of being incorrect, exposed, alienated, or damned is the kind of fear that chokes the life out of a newsletter.
Many think that fear is reserved for new and inexperienced writers— something you get over after you publish a few times. This is only true if you’re coasting— putting out writing of a nature that’s already tested and safe. But each essay is an opportunity to break into new ground you’ve never entered before. If I fear I’ve gone too far, it means I’m writing at the edge of where I’ve been, and it means I won’t be boring you.
I want a newsletter that is soaked in imagery. I want a newsletter that tears a hole in your Gmail. I want a newsletter like a highway wreck you slow down to look at every time.
I want a newsletter that avoids the Newsletter Junkyard.
Until next time,
PS: Thank you to my feedback givers: Isabel Hazan, Aditya Verma, Arthur Plainview, Anthony Polanco, Simone Silverstein, Will Mannon, Charlie Becker, Nic Hurrell, Tommy Lee, Ken Rice, Salman Ansari, Henk Bruinsma, Karena de Souza, Chris Wong, Rik van den Berge, Leo Ariel, Promeet Mansata
PSS, True Story:
When I wrote, “I want to write a newsletter that foams at the mouth,” I heard loud shrieking outside.. Is an animal being mutilated, or are these noises from my neighbor Wilbur Doyle’s scrapyard? I investigate different corners of the house to find the source .. the front! I sprint outside, barefoot with an IPA, look to my left, and see a pack of raccoons. Four of them sprint up a tree; one is being chased by the other three. It’s a brawl. There’s beef. A raccoon is dangling. Which one has rabies? Do they all have rabies? “Cut it out!” I yelled, before eight glowing eyes appeared in the 10pm darkness. This is surreal. Either my writing summoned these beasts, my subconscious is tuned into the animal energies of Big Finger, or. it’s all a beautiful coincidence. I want my newsletter subscribers to be hardcore, but a telepathic raccoon fight club is a bit much.