michael-dean-k/

Link to one of your pieces you want to make sure we read. Why is this a good example of your writing for this progress blog-building program? Why are you proud of this piece?

Essay Writing as Personal Sovereignty was a winner of the Cosmos Institute Essay Prize, and it speaks to the importance of the manual effort of writing essays through the age of AI. It looks back to the origin of the essay, and how the early tradition of Montaigne failed to scale and integrate into our systems of mass education. I'd like to use my fellowship to go deeper onto this, to explore the history and future of writing curriculums.

What topics or areas do you want to write about? What about this is interesting to you? Why does it matter?

I've been blogging for 6 years and published over a million words. I want to study the history of education, writing, and autonomy, so that I can charter a vision for writing curricula in the 21st century. In 2024 I won a $100k O'Shaughnessy Fellowship, which enabled me to write a textbook on essay composition, and develop software that can analyze craft along a pattern language I designed. Focusing on history and progress will give me the context I need to found an institute dedicated to reviving how we teach the essay at scale.

What is your "angle" for human talent & potential? What particular areas (e.g. workforce development, adapting to AI, education, immigration, fertility, gender), challenges, or opportunities do you want to explore?

Human potential is gated less by talent and more so by the mechanical way we've taught writing at scale. AI is dismantling that system and creating a new opportunity. A new writing curriculum, grounded in autonomy, would be anchored in software that helps a writer improve how they can articulate ideas they actually care about. In this model, AI would never write for them. They would be guided by a series of "margin muses" (editors, socratic agents) both within and outside the piece. Over time it will understand a student's strengths and weaknesses, and guide them down a custom track of readings, lessons, and exercises. By compressing the arc of mastery from years into months, students will feel their rate of progress and continue toward the pursuit of their own original ideas. By fixing this, we don't just get better test scores or literary prose, but a wider pipeline of articulate, critical thinkers.

Tell us a bit about your background for the human talent & potential track. What unique knowledge, experiences, or perspective do you bring to exploring progress in human talent & potential?

1. As Editor in Chief and curriculum lead at Write of Passage, I helped thousands of writers improve their ability to write, and distilled insights from thousands of drafts into a pattern language and 25k-word textbook on essay craft;
2. I hosted a $10,000 essay prize last year that resulted in The Best Internet Essays 2025, an anthology that fused AI and human judgement. My editing system scores each essay 1-5 across 27 patterns; AI provides an objective "craft" score, while human judges cover the intangibles. Currently improving my eval system and aggregating RSS feeds so that I can scout the best essays across Substack in 2026.

My unique perspective: I've felt the dramatic rate that writers can improve, and I think we can measure and augment it too.

Share a great essay you've recently read on human talent & potential. This could be something exploring a policy question, a recent phenomenon, or an exploration of the impact of an innovation, or even a utopian vision piece. What about this essay speaks to you? Which ideas resonate? Why does this essay matter for those interested in human talent & potential? What perspectives might you add?

Check out The Age of the Essay by Paul Graham. This essay is a pillar I come back to, because it covers history, process, and future: he critiques the history of writing education (the five-paragraph essay is a hangover from medieval law schools), explains how essays are actually a multi-branched exploration to a question, and then speaks to how the Internet could enable the 21st century to become the age of the essay. I find it interesting that Graham wrote this not long before he founded Y-Combinator Sep 2004), and wonder how much of his thinking here influenced the success of that program. Many of the notable founders in cohort 1 were bloggers who used writing to think (Aaron Schwartz, Sam Altman, etc.). Related to progress, I think there's a meta-lesson in understanding how new technological networks can open up new affordances to revive old practices.

An added perspective: Graham was right in that the removal of gatekeepers opened up a new wave of writing talent, but missed the fact that it also opened a new flood of slop that would make that talent harder to find. The important lesson is that you can't remove gatekeepers without implementing a sophisticated curation system. I write about this in my essay "The Signal in the Slop," the opening of my anthology, The Best Internet Essays 2025.

Your current situation. Give us a bit of context on you--e.g., what you're working on now, at what organization, and anything else you want us to know about you.

I'm working full-time on my project Essay Architecture: writing, researching, building software, scouting essays, organizing a community, and hosting weekly calls where we deconstruct classic essays. In the last few years I built an audience of 10,000 followers, and now I'm figuring out how to formalize my efforts into an institute (sustainable income paired with mission-aligned projects).

Writing and your career. How do you see writing on progress topics fitting into your career plans over the next 5 or so years? As you envision your success as a writer, what do you want to accomplish with your writing in the next 5 years? Do you have goals on frequency of publishing, places you want to publish, or audiences you want to reach?

Within 5 years, I want Essay Architecture to function as a standalone writing institute that different groups can plug into: Substackers, students, micro schools, homeschoolers, etc. It will provide editing software, textbooks and anthologies, a library of thousands of scored/categorized essays, and the ability to guide writers down custom learning paths based on the drafts they upload.

The goal of my progress-related writing is to: 1) publish pillar pieces on the importance, history, and future of writing curriculums; 2) attract students to the institute; 3) build a network of partners who are operating within or connected to the worlds of EdTech or alternative schooling.

I'm in the process of rethinking my writing infrastructure. All essays will live on a personal website (launching in June), where Substack will serve as a weekly newsletter to redirect readers to my essays, products, etc. I believe it's important for a writer to manage different publishing velocities. In May I published 33 essays averaging ~600 words each. In the last year, I've averaged a monthly long form essay at ~3,000 words. I'd like to produce something at my peak quality that gets published in a journal or magazine around 2-6 times per year.

What are you looking to get out of this blog-building intensive?

I'm looking to immerse myself in a community of progress-minded writers, to get rigorous feedback on my ideas, and find guidance on how to formalize my project into a sustainable institute.