The A.S.S. Model for Internet Writing

No one really reads anymore.

In part, I think this is because we’re all flooded with memes, messages, and internet chaos every day, so our attention spans have been whittled down to nothing. In part, I think this is because there is so much quality content out there to consume. Like, why would you read when you could spend your free time scrolling social media, binging TV shows with decamillion dollar budgets, or shuffling through all music ever made?

Now, I don’t think it’s totally over for writing. At least I hope it’s not. But one thing is clear to me: if you want real humans to read what you have to say in the internet era, it has to be ferociously high quality. You need to figure out how to hook people who have broken (and waning) attention spans, then keep their attention while competing against the entire entertainment-industrial complex for a slice of their time. Hard to do, but not impossible.

I think three things matter if you want to publish work at this level i.e. writing that gets people reading… not skimming, not reading the opening 5 sentences and closing the tab, reading, whether it’s a tweet, an email, a thought piece, whatever. It comes down to understanding your audience, having a coherent structure, and writing with your own style. Let’s riff on each.

Audience. All good writers have an opinionated view of who they’re writing for.

This could be high level, like writing for all basketball fans. It could also be hyper specific, like writing for people who are obsessed with Tubby Cat NFTs. The point is: having something to say when you write isn’t enough. You have to adapt content to a particular audience because those constraints are what make the writing come alive.

Let’s take Anthony Bourdain’s memoir Kitchen Confidential as an example. The book hits so hard because he wrote it for the restaurant industry, and he did it with an insider’s tone, quirks and sense of humor. What made it so high quality was it was so high context.

The main writing lesson from that book is to be clear who your readers are. If you can write about whatever your topic is with relevant references, experiences, and terminology then other similar-minded folks will be drawn in. Ultimately, attuning what you say to a specific audience is relevant for everything from low register shitposting on Twitter to high register research for academic journals.

One way I try to integrate this thinking into my essays is by obsessing over accessibility. I know I’m writing for busy people in tech, finance, and creative industries who (maybe) trust me with 5-7 minutes of their time while procrastinating at work, so everything has to be casual otherwise most of you won’t bother reading.

Structure. All the best writing presents ideas in an order that just makes sense.

In his book Draft No. 4, John McPhee says, “a piece of writing has to start somewhere, go somewhere, and sit down when it gets there.” What I take from that quote is, in all cases, good writing is a game of creating good structure. The challenging thing about structure in writing though is it’s not a math equation. There is no single correct way to write anything, and writers need to figure out what to say, when, and why.

In wrestling with those trade-offs, there is one “rule” that I come back to (also from McPhee) which is letting your ideas about a topic create a structure for you instead of trying to force something from the top down. For example, I’ll collect ideas about a topic, compile them into digital bullet points, and pull those ideas around until something makes sense. This story works here, this anecdote works below that, this joke needs to get cut… it’s an emergent process. Eventually, you hack out a rough outline, and voilà.

One caveat: people can for sure shoot from the hip and just write. Often the best work comes out in fits of emotion, inspiration, or good vibes. But even then, you can usually triage your rambling with some restructuring and make it more coherent.

Style. All elite writers have a unique voice. It’s what separates the great from the good.

Take a second and think of a book or essay that stands out in your memory. If I had to bet, it probably got stuck there because of the author’s style. It’s the way David Foster Wallace talks about tennis and the way Joan Didion talks about illness that makes their work so electric to read, less the subject matter itself.

I think cultivating your own writing style is a lifetime journey for everyone who likes to move words around on a screen for fun, and it’s impossible to really tell other people how they should create something that is so personal, but beyond just reading and writing a lot and getting the reps in there are two things I’ve personally found helpful here.

First, focus on being authentic. Consume content you like, then filter ideas about those topics through your own voice. Whatever you can do to inject more personality into your writing will help it stand out. Second, have fun on the page. No one wants to read another eye-bleedingly boring ChatGPT output, and people can tell when writers are jazzed about their own work. It pulls you in.

To close out here, I want to say that I’m confident writing has its place in the digital age. People will always be readers because writing is just thinking on paper (or screens), and good thinking always has an audience.

That said, it’s already tricky to compete for attention in the social media era, and over time the torrent of content we all consume daily is just going to get more insane, so writing has to get a lot right to cut through the noise.

The best way I know how to execute at that level is by obsessing over who you’re writing for, what order your ideas are presented in, and how your content is filtered through your own voice and life experience. Audience, structure, style. A.S.S. I think if you get those three parts right, everything else falls into place.