So Alex Dobrenko started a new personal website (I will not link to it because it’s secret), but he sent it to me, so I spent some time on it and wrote him some notes, and then he wrote a reply post to me, and now I’m making a reply log to that (and upon re-reading, I realize it’s now a whole essay). It’s something like a semi-public letter exchange.
Letters, emails, same thing.
Similar to how the 20th century has books like “Virginia Woolf: The Letters,” I wonder if the 21st century will have “Alex Dobrenko: The Emails,” where his children posthumously assemble and publish all their dad’s best emails. ((Also, now that my cholesterol is borderline, and my daughter is on the way, I’m having new thoughts about preparing for my death, like “THIS IS DAD FROM THE PAST AND HERE ARE ALL THE PASSWORDS.”) Something about losing all my writing forever feels worse than dying. We eventually have to die, but you only lose your writing forever if you’re careless and lazy. Rant over.)
What I like about letters/emails over essays is that there isn’t a mass-market context, and so you’re writing for just one person. That’s good essay advice too (“write for one person”—we literally taught this in Write of Passage), but deep down, it’s hard to forget that you’re writing for all people of all times, especially if you are.
Recently I mentioned that I’ve spent 2 years nerding out on essay patterns (the objective stuff on the page), but I want to start thinking more about the process: how do I show up to write?
One idea is to start essays as letters to specific people. Eventually, that can evolve into something for the main list, but I don’t want to start with them in mind. I want to start with a specific problem in my life, and then, with a small group of people who relate to that problem. Any idea I have comes with a clear person in mind, someone who would probably be most excited to read it, and has all the context needed so I can avoid the bush beating.
If I want to write about Alternate Internet Communities and weird websites, I’ll write to Alex. If I want to write about the insanity of the Dark Enlightenment, I’ll write to Andrew. Theology to Taylor, Emerson to Will, Hope to Isabel, Fatherhood to Dan, Greeks to Chris, Dreams to Garrett, AGI to Davey, Architecture to Liz, etc. It’s also special to say, “I wrote this for you, and we should talk and get to the bottom of this,” and that could really change the nature of the essay because someone else is co-shaping it with you.
Alex brings up a good question: why doesn’t Substack feel like this? I have to think more on this, but I think the stage effect is still at play. If you have a 10k audience, it still feels like a megaphone, and when you’re on Notes, you participate in American Idol, again with new skin. It’s still the best town in town, and there are tricks (ie: set up an opt-in Section for experiments so you can have a “shadow audience” that’s 1% the size of your main one), but there’s friction in tricks like that. It’s not the main way the platform is intended to be used. It’s meant for loud, marketing-style updates, that confidently funnel readers into a paid subscription tier (I got 15 paid subs from my last one, and so I realize the value in learning to play that game, but it’s just that, a game, yet a game that determines my financial security, but it’s not the full “culture” in “culture engine” that Substack can possibly build; it’s a reward function that could make this place like LinkedIn in <3 years).
So, how do you build a “culture engine,” for real? What is it beyond a tagline or positioning? To start, I think it goes beyond revenue. Of course, Substack needs to pay bills (separate point, but once we reach the vibe code singularity, the bills might be so low that SM networks won’t have to ruthlessly optimize). I think Substack could 1) diversify their business model, so that they don’t have a single attractor that incentives every thought to be monetized, and 2) make decisions from a cultural perspective—even if there’s no explicit revenue tie-in, by creating a good culture, you retain the people and prevent a Writer’s Exodus.
But to get even more specific, a “culture engine,” sounds like the kind of place that would trigger long letters back and forth between writers, kind of like this. I used to see some of that happening, but it seemed like a performance too: “And now, here is email 6 of 7 about how to start a public email debate” or something. The core difference is that, when there’s two people writing back and forth, there’s permission to perform less and less until you’re eventually just very real with each other. This is what I love about Neal Cassady’s letters to Jack Kerouac (troubled guys, who are a topic for another time).
Why aren’t Substack comments like this? For one, they’re truncated. But two, I don’t know, sometimes comments even feel performative too? I feel it, on both the giving and receiving end. After I post, it feels like a chore to respond, even though I often love what people write and want to respond. I think it’s because, since it’s in public, and everyone can read, it feels like an obligation to respond. I wish there was an option to have “private comments,” and even “private replies to comments.” Like, other readers could see, “Michael Dean replied to this, privately” so they know I’m not a dick.
Okay, last thing, maybe: I think the real problem is that the discovery mechanics are all wrong. Like, I don’t want to blast this letter to everyone I know. But yet also, I don’t mind if everyone I know happens to stumble across it. There is a huge difference. I’ll put this in my logs, but realistically, no one is going to find it. I guess I could put it on Notes? But that feels too vulnerable too. Ideally, the right people will find it as they write about similar issues. So if some Substacker is also writing about private comments, to themselves, or to a friend, they will suddenly find a thread between Alex and Michael talking about a similar thing, and then suddenly we all have visibility into each other’s notes, letters, essays about those things. Forks merged.
The social media network I want to park in (or plug my personal website into) is one where everything is semi-public, but you only discover things through your own writing. I don’t know the right metaphor: it’s like each notes or essay is a flashlight that you use to move around this massive information cavern and you make friends along the way. It has nothing to do with engagement or revenue, but semantic similarity. This feels closer to the original vision of the Internet, to connect people based on ideas.
Sublime has some features that are adjacent to this, and Plexus was very close to this too, but I do think there’s something to owning your place. Is there some protocol where you can fuse the autonomy of your website with the connectivity of a network? I feel like AI is going to simultaneously bring us to (a) slop town, and (b) a golden age in social media experimentation; as sloptown gets neck high, people will want to move.
PS1: To clarify: I love having an audience, I just don’t love the way my writing is distributed to them, and also don’t love the way conversation is facilitated. Comments are okay, but the Chat feature feels pretty off. I wish I could write 30 essays per month, like this, and each one would get the 3 that are most relevant.
PS2: It took Alex 9 days to reply to my original notes, which is still ~2x faster than the letter cadence back in the day. That’s fast! I wonder if AIM culture poisoned letter culture. I haven’t responded to my Substack comments from 5 days ago, and I feel bad.