Winners of the $10k essay prize

Congrats to Tommy Dixon and the 10 finalists in our new print anthology, The Best Internet Essays 2025

A friend texted me this weekend—“I am too addicted to Claude code and need to touch grass. You said I should read an essay book can you recommend one that I can order physical”—not knowing I was about to launch The Best Internet Essays 2025.

This little book, a 4.25” paperback that fits in my pocket, is the manifestation of a big, borderline extreme process I was entangled in all of last year: I wrote a textbook on essay composition, analyzed classic essays along my framework, built software to give feedback, which powered a tech-forward essay prize, creating a shortlist for our team of judges, all leading to this—an anthology. Since Essay Architecture risks veering into hyperanalysis, it’s relieving to have something much simpler I can share. It’s a book. You can read it, experience it, a single thing with a URL I can text Andrew along with “yeah here are some great internet essays written in 2025 about 2025.”

From over 900k words processed across 400 uploads, we had 10 judges (each with their own criteria) who read every essay on the shortlist. It was fascinating to read through their comments and scores: if you looked at any one essay, it seemed like there was little consensus, that quality is subjective, that there can be no “best”; but if you zoom out and compile the results, it’s clear that some essays resonated across many different lenses. Those essays are the ones we’re printing. Congrats to the winner of our first prize, Tommy Dixon, and to all the finalists who contributed powerful, personal, “unitive” essays to make a mosaic of our year. You’ll find recurring themes on rootedness, loss, wonder, vulnerability, and ultimately, the power of attention in a culture designed to hijack it.

The Best Internet Essays 2025:

• Features 13 essays from the Essay Architecture Prize;

• Limited edition: 1,000 copies;

• Available March 11th - March 31st;

• Shipping starts in April;

• Pocket-sized paperback, 4.25” x 6.875”;

• 183 pages;

• $29 (+$8 for shipping).

Most importantly, 100% of royalties go to the writers, the judges, and the 2026 prize pool. When you buy a copy, you’re directly supporting the people behind the essays, the team who helped surface them, and the future of this anthology.

Head over to our Metalabel release page to see the winners and get a copy.

If you’re a reader of Essay Architecture, it’s definitely worth having a physical book of essays within arms reach at, almost, all times. Printed essay anthologies are an underrated genre. Commercially, they basically don’t exist, usually limited to a single half-shelf in a secret corner of a Barnes & Noble. But if you’re an aspiring writer, it’s the best kind of book to own. You get a range of ideas, a range of voices, a little universe of inspiration all within one cover. If the book is well-curated and well-edited, it’s the kind of thing you can reliably pick up to get a full dose of literature in a single sitting. I scatter these across my home so I’m more likely to accidentally fall into one.

Also, this particular anthology fits in your pocket (I’d prove it but am hesitant to post crotch-adjacent photography online). There’s a collector’s mentality of seeing big, hardcover, premium books as a mark of quality. Personally, I like my essay books small and bendy. Portability is a huge asset, especially as spring nears. Bring it outside without a bag, on trains, to parks, wherever. Leave the phone home, too. The vision is to, each year, curate the best writing online, the writing the algorithm may or may not miss, the writing you’d likely flick through on your phone, the amazing writing you find and bookmark but inevitably forget—to assemble all the essays worth reading off your phone and onto a printed thing about the same size as a phone.

In the coming weeks I’ll be writing more about the anthology, the emerging themes, and the vision of this becoming an annual effort to curate Internet essays.