Built myself a personal app that pulls from the Readwise API so that highlights could sync to my computer (unlike the Obsidian app which groups them per book, mine has a markdown file per highlight). Built an interface around it so that I could write responses to each highlight and give them metadata (title, date, etc.), and then they're pushed to my website. I called it "Frequentation" (because a personal doesn't need a simple title, just a meaningful), because it's a word Montaigne uses for returning to books he loves repeatedly, which is the goal of this project.

Setting up a personal website as the new place for where my writing lives. I'll still publish to Substack, but the format there is TBD. Currently, writing and building this is too fun to ignore, so I'm going to see where it leads. I wrote a little guide on how I built this. In additional to it being a full archive of my logs, essays, definitions, and notes, I'm excited for a few features, especially the fact that people can comment without accounts.

Building a list of 12-14 classic essays for Essay Club to read each week. Unlike a book club, we can read the full work together on the call, in 10-30 minutes. After that we'll do breakouts, discussion, and some annotated visuals using the Essay Architecture patterns. Starts Memorial Day.

Hosted a workshop with the London Writer's Salon that looked into essays as both a genre and a mode of thinking, from Montaigne to Substack, and closed with some exercises.

I've been building out the scaffolding for a v2 of the Essay Architecture software. The core change is that it's evolving from a reporting tool to an editor, where AI agents leave comments in the margins. I'm starting a starting a devBlog to share the musings and mishaps of building this. First one is here.

Launched an anthology called The Best Internet Essays 2025, which features the winner and finalists from the $10,000 essay prize I hosted last year. We sold 350 copies through Metalabel, where 100% of the profits went to the writers, the judges, and the 2026 prize pool. I wrote about essay anthologies, the emergent theme, and interviewed the winner, Tommy Dixon.

Had a chat with Lindsay about different issues in AI ethics.

Vibe-coded a new home base for our 60 members in Essay Club. After using community tools like this for year, it was fun to build one specific for our needs, which includes monthly goal setting, feedback exchange, publishing tracking, etc.

Launched an app where you can upload your draft and get analyzed on 27 patterns. It identifies your strengths and weaknesses in craft, and gives you feedback ideas which you can add to an editing checklist. Currently live at essayarchitecture.com. Check out $9 Essay Coach.

Check out I'm giving $10,000 to the best essay of 2025. The goal was to make an Internet native essay prize, one without any entry constraints (ie: no rules around location, age, or prompt), one with transparent and detailed judging criteria, and one that writers own (no exclusive publishing rights, and winners get royalties).

Published about 25,000 words on Substack of essay composition theory for paid subscribers. There's an essay for each dimension, and then each pattern includes a definition, why it matters, examples, exercises, and related concepts. Here's the table of contents.

My episode with Jim O'Shaughnessy , where we get into writing, editing, and how schools should deal with AI in education.

A chat with Charlie Bleecker on the writer/editor relationship, and on Show vs. Tell, after working together for 18 months on several drafts of her memoir.

Published an essay, "Burn Down Your Architecture," on a new method of aligning my essay evaluator scores with my control set. Even though context windows are growing, an LLM will randomly pick a different excerpt of an essay each time and base the analysis on that. By going granular, slicing each essay into a paragraphs, running granular evals, and then aggregating the results, you can get much higher precision.

Edited essays for Cosmos Institute, including The Philosopher-Builder.

A fun chat with Michael Garfield, titled "The Architecture of the Next Creative Economy."

Podcast episode with David Perell on and reflected on it a bit here. We deconstructed two essays ("Consider the Lobsters" by David Foster Wallace and "Shooting an Elephant" by George Orwell), and then got into process, patterns, and technology.

A fun chat with Matt Trinetti from LWS. Here's the link.

Read and scored the whole BAE '24 anthology along the Essay Architecture framework. Published an essay with the results. The top 3-5 scoring essays were excellent, among the best I've read, but the average was below bar (I believe a 3.7 of 5). It seems the anthology is filtering for vulnerability, trauma, and personal experience, and ignores other core qualities of the essay. This was part of the inspiration in starting my own prize and anthology with a more holistic definition of an essay.

Judged a prize for "Writer's Hour Magazine," where the prompt was One Great Paragraph, focusing on three Essay Architecture patterns. "

Wrote the essay that introduces how and why my pattern language was designed, which ended up becoming the introduction for my textbook.

Won the Cosmo Institute essay prize with "Essay Writing as Personal Sovereignty," which argued that even in face of superintelligent essay writers, the act of writing and editing is how we come to make up our mind. Was invited to Oxford to attend a lecture and dinner.

Launched a community with a monthly publishing interval. We publish by the 1st. We meet weekly on Fridays at 3pm ET to exchange drafts and ideas, or even just to block out the time to write.

Built an early version of the Essay Architecture app, both for prompt evaluations and for user-facing feedback via spider graphs. Beta testing started in January.

Found my grandfather's typewriter from the 60s in my grandfather's basement. The inside was filled with mold and I did my best to clean it, but probably still need to get it professionally done.

Won $100,000 for an OSV Fellowship to develop a textbook and software for Essay Architecture.

First published my list of scored essays, which now has turned into essayarchitecture.com/library. Launched this with a review of "On Interpretation" by Susan Sontag and "Here is New York" by EB White.

Previously called "Dean's List," this title is more legible and aligned with what I do, and noticed a spike in audience growth from this moment on.

Reviewed the book Food of the Gods by Terence McKenna for the Astral Codex Ten book review but didn't place as a finalist. Here are the winners. Still happy with my essay, "The Babbling Idiot and the Tribe," not just for the output, but because it let me dig into, disprove, and extend the stoned ape theory.

Second typewriter, no earplugs required, and so now my default.

Turned these on.

First viral essay on Substack, and the launch of Essay Architecture.

Worked with Davey Morse on some design-related ideas for Plexus.

Built a prototype for a text editor where an AI reads your sentences as you type and surfaces related notes via embeddings.

Redesigned the Write of Passage curriculum from scratch so that the concepts were more aligned with student assignments and publishing.

Started the new year on a new platform with the essay "Substack or bust." At the time I was excited by the idea of having a website, newsletter, and social media platform all in one.

Helped David Perell structure and edit The Ultimate Guide to Writing Online which is a distillation of the Write of Passage curriculum.

Built out an editor test by writing out an essay draft that was broken in multiple dimensions, and then built a 60-point to system to see how well editors would pick up on them. It looked at both an editor's ability to find compositional holes, and also the way in which they delivered the feedback.

First typewriter. Way louder than I expected.

Worked with Write of Passage alumni 1-on-1 to publish essays that would live on the company's website. Essays: A Pilgrimage for Book People by Charlie Becker, IKEA Words by Andrew Plainview, Pseudonymous Cape by Charlie Bleecker, Metaphors by Camilo Moreno-Salamance, Why Editing Sucks and What To Do About It by Christin Chong, From Fear to Thriving by Angie Wang, Summoning the Muses by Lyssa Menard, The Dance of the Bees by Chris Wong, The Comedian's Guide to Feedback by Raza Jafri.

Launched a website on Ghost, originally called "Dean's List," for the sake of combining my website and newsletter into one thing (at the time I was publishing on Notion, but never sending via email). It only survived for 7 months, probably because there was too much friction in having people comment compared to Substack (each Ghost site needs it's own account system).

Started working full-time for Write of Passage (1.5 years).

Started a new practice on a private Notion page where I'd document my reflections throughout the day. Partly inspired by Justin Hall's website (links.net) and by recently reading Fernando Pessoa's "The Book of Disquiet."

Set the quality standard for Write of Passage, a training program around it, and systems to we could manage hundreds of drafts across cohorts.

Launched and ran 5 cohort-based courses in between Write of Passage seasons. Each one had 10-20 writers, featured 1-2 calls per week of writing exercises, and 1:1 meetings to help them publish one great essay by the end of the month.

After going dormant with writing for a few months after my first Write of Passage cohort, I found new momentum by shifting to a public Notion site. Unlike Squarespace which had a whole uploading ritual, Notion fused my drafting/publishing environment, which let something become public by clicking a checkmark.

Took Write of Passage cohort 5 in the summer of the pandemic to start writing online. My first essay published was "Studio Culture."