Nobody belongs anymore
The belonging crisis is real. And structural.
Published Essays
Get to know members by reading and commenting on their essays.
Loop #19 April 2026
Loop #18 March 2026
When I fell in love with a married man
Not all mistress stories follow the same script
The Fetch Problem
Why most people are using AI like a very impressive dog and what the shift actually looks like
I had a kernel of an idea and polished the idea with input from the larger group. However, unlike my last essay, I did not iterate on the essay enough. I am not really pleased with the output but decided …
We are big floating heads looking for our bodies
A conversation with Tommy Dixon
Published an essay based on my interview with Tommy Dixon. Made a good dent in "The Signal in the Slop" draft too, which will be the introduction of The Best Internet Essays 2025.
Goodbye Friend
On my strange eulogy for a best friend breakup
I wrote it in basically one day! Like 6-ish hours for 1300 words. Not bad, flowed mostly well.
Guilty Grief
Delayed Revelations and Learning Discerning
The weight of things
The manosphere, men without chests, and the training no one gave us
You Really Can Just Do Things
My psychotic trip down the rabbit hole with Claude
When I started writing this, I didn't know where it would go. Realizing I was afraid of what might happen if I actually made these things real was strange.
The humanities revolution has already begun
Why the contemplative life is making a comeback
Opinions are like assholes
An enema for your thoughts
I battled with this one for a long time! I wrote 5 other essays worth of material and am still grieving all the things I lost. Your thoughts welcome.
Loop #17 February 2026
Winners of the $10k essay prize
Congrats to Tommy Dixon and the 10 finalists in our new print anthology, The Best Internet Essays 2025
I ended up pausing my work on "micro-institutes" and published the annoucement for Best Internet Essays 2025. This is maybe a good example of future weekly essays I could post, around 800 words, with a clear CTA. For the longer …
Everyone has a plan until you get punched in the face
On birth plans and the illusion of control
I was mostly trying to just break the seal and post something! I enjoyed the process :)
I Say I Want A Revolution
I’ve got a lot of problems with music, but who’s counting?
A Dance with Chance
Tilting luck in your favor without the delusion of control
The highest thing in the room
Against the horizontal life
An Update on Direction 2026
This is what I am doing now, and why.
This was a big deal for me as it marked a pivot point in content, commitment, and lifestyle.
The Chinese Mentality
and a peaceful acceptance of the authority
"Some Things Are Just Shit"
Choking down reality and finding a way forward in grief
Indian Royal Fast Food
I heard mashallah more times than I could count over lunch.
What AI is really doing to work
A one month retrospective from the frontier at Fractal Tech NYC
Very useful to have written much of it through daily little Notes/posts throughout the month
How To Finally Remember the Books You Read
Stop chasing book counts. Start designing a revisit system that actually sticks.
It took me a long time to write this piece. It was difficult to find a way to write an easy-to-follow story without making it too technical. (Not sure if the link already works. I submitted it to a Medium …
The importance of thinking
Value the process as much as the product.
Trying to write a long essay about opinions but it's been murdering me. Here is one of my weekly newsletters which contained an excerpt from one of the essay drafts.
Neither Here Nor There
A reflection on an immigrant's journey
Is human control over AI even possible?
Lingering questions about AI, democracy, and what we mean by human control
Towards a New Understanding of Being
Rebuilding meaning based on a truth we all have experienced
Loop #16 January 2026
Notes #1
An experiment in ghost-posting notes that I’ve posted in the past month
I've been trying to do more notes, to do more casual writing and grease the groove, lower the bar for publishing. Per Michael's suggestion, I've gathered and ghost-posted these three notes, which are brief but I think do represent a …
Taking the Stairs Won't Fix It
Sometimes you need someone to send the elevator
I had too many ideas and competing metaphors and the feedback from Matt really helped me, pick something.
Heart Pillow
A meditation on the loves we do not celebrate
I am trying to be more vulnerable in my writing. Hope this resonates.
When Dayenu Isn’t Enough
An essay about a love that isn’t romantic, friendly, familial, or anything else I know.
I used the Essay Analysis tool to work through this draft, and it felt so satisfying to see the score rise from 3.16 to 3.25 to 3.37!
Signs of Humanity No. 3 - Thank You In-Laws
Thank you for helping me unpack my dead sister’s boxes of clothes
Icons of a different kingdom
Technology and the theft of conscious participation
33 and NYC
Tech bro'ing out in the city of dreams
Somehow managed even to publish a blog post at the last minute, sigh. It's hard to write a little bit at a time! Or maybe I needed to really move to NYC to feel it, so that I could write …
Developing Discernment
How can we see what works when we move so fast and we’re not making the decisions?
I tried to respond to the feedback from essay architecture software, but I find it so challenging. I was trying to rework the essay to include more perspective specifically but in the end I gave up and published it anyways! …
Notes for when I overthink
Becoming the person who just does things
A piece about how to stop overthinking.
Baby-Induced Life Reflections
The Drawing Board #22
A newsletter post of questions that will prompt future posts for my maternity leave reflections.
You’re always closest to what you build
Work is where life is, my orientation for 2026
When Meaning Breaks Bad
William James on why religion persists and what it costs.
This piece was a reflection on one of the most profound books I've read recently: the Varieties of Religious Experience by William James. I intended it to be an essayistic book review, synthesizing three things William James brought to the …
The long boomer farewell
This will not be a clean handoff. It will be an extended interregnum.
When Meaning Breaks Bad
William James on why religion persists and what it costs.
This piece was a reflection on one of the most profound books I've read recently: the Varieties of Religious Experience by William James. I intended it to be an essayistic book review, synthesizing three things William James brought to the …
When Meaning Breaks Bad
William James on why religion persists and what it costs.
This piece was a reflection on one of the most profound books I've read recently: the Varieties of Religious Experience by William James. I intended it to be an essayistic book review, synthesizing three things William James brought to the …
When Meaning Breaks Bad
William James on why religion persists and what it costs.
This piece was a reflection on one of the most profound books I've read recently: the Varieties of Religious Experience by William James. I intended it to be an essayistic book review, synthesizing three things William James brought to the …
User-Directed Experimentation (or, Experimentation for Human Flourishing)
Today, companies experiment on users. Tomorrow, users will experiment on companies too - with very different goals.
Notes after fatherhood
I posted 5 Notes in January, between 200-800 words. I wrote a draft of the essay I wanted to publish, but it didn't make it through. I have a better idea of what it should be, but will take me …
Loop #15 December 2025
You Are Not a Tree
"How long are you going to wait before you demand the best for yourself?" — Epictetus
With These Two Songs I’ll Be Alright
Listening for voices to lead me through resistance
logloglog
December 2025
Reflections on newborns, Bauhaus, timelessness, infinite, robots, Voltaire, male nesting, Claude, TetherOS, Harada method, techno-activism, corporate architecture, Santa, Kenya, formaldehyde, epistemic adverbs, etc.
Sweetbitter Love
Letting go by never letting go
Death of a Peacemaker
Death as permission
Roughly Three Homes
Musing on what home means to me
What Love is Not
For anyone else stuck in love. Here’s my story.
Loop #15
How To Improve Your Brain By Talking to LLMs
Married to the hustle, trying to date happiness
My ambition keeps crowding out joy
Boomer caregiving will wreck our politics
We have maybe five years to escape gerontocratic capture
Loop #14 November 2025
The forbidden grief of white America
Norman Rockwell and the grief that dare not speak its name
1 Year of Writing
On Substack, Statistics, and Sentimentality
Quality is the Transcendence of Categories
Announcing the judges for the 2025 Essay Architecture Prize & the judging system that will shape the anthology
Very happy with the thesis that emerged from this: there isn't a single metric that can determine quality, but you can see up a bunch of categories, and notice which ones excel int he most. Yet, this was posted WAY …
Loop #13 October 2025
$9 essay coach
The feedback you won't get from your friends, family, and chatbots
Loop #12 September 2025
Essay Architecture Textbook
Posts for 27 patterns, 9 elements, 3 dimensions
Loop #11 August 2025
I'm giving $10,000 to the best essay of 2025
And the finalists will get published in a printed Metalabel anthology (submit by 11/23/2025)
Loop #10 July 2025
Burn Down Your Architecture
https://www.michaeldean.site/p/burn-down-your-architecture
Loop #9 June 2025
Atomic evaluations, NYC, Dia browser, UBI speculation, essay culture, cranky neighbors, "For you, for all of humanity!", Hiromi, usage, AI horror, Montaigne in a vat, etc.
logloglog | 2025-06-June (137)
Loop #8 May 2025
The Babbling Idiot and the Tribe
Did psychedelics guide human evolution, or is the Stoned Ape Theory just for stoners?
Loop #7 April 2025
Logbot, Sphere Hype, Prompt engineering, Kanye, Go, Galactic Years, Gibhli Slop, Holy Week, Black Mirror, SEARS mattresses, The zoo, Guitar, Some nuances on roach poison, Counterclockwise clocks
logloglog | 2025-04-April (155)
Loop #6 March 2025
Severance, Slop, Grateful Dead, Death, Agents
logloglog | 2025-03-March (155)
Loop #5 February 2025
Thank you for the roses
TikTok, NPCs, and the pitfalls of agency gambling
Loop #4 January 2025
Best American Essays?
Let's analyze composition across the 2024 anthology
Loop #3 December 2024
obisdian, XMAS, futurism
logloglog | 2024-12-December (126)
Loop #2 November 2024
post-election hangover
goals for 2028
Loop #1 October 2024
Essay Writing as Personal Sovereignty
Shaping AI to preserve the slow craft of critical thought