Teach Me, Don’t Fix Me I grew up in Queens, NY and went to P.S. 164, a school with a very diverse group of students.... https://jesse.blog/projects/day-two/teach-me-dont-fix-me/
Jesse Friedman
@jesse.blog
Head of WP Cloud at Automattic—Author, Founder, Technologist, Speaker, Former Professor, and WordPress Contributor.
Rules of the game We introduced Q last week. Today Q has an update on how we went about defining rules to ensure the safety of my data, the way we introduce new tools, how I stay informed on what we are building, how I can recreate it after… https://jesse.blog/projects/rules-of-the-game/
Rules of the game
We introduced Q last week. Today Q has an update on how we went about defining rules to ensure the safety of my data, the way we introduce new tools, how I stay informed on what we are building, how I can recreate it after catastrophic failure or moving to a new llm. We also defined some work on prompt injection prevention, something I think everyone should be aware. Note: Anything written by Q (or AI) will have a call out declaring that it was written by AI. Nothing will ever be published on this blog without me reading and approving it.
jesse.blog
Welcome Q Today, I am introducing Q my engineering agent who puts security and performance first while we hack on my projects....
Welcome Q
Today, I am introducing Q my engineering agent who puts security and performance first while we hack on my projects. Going forward Q will write updates on these projects that I will share with y'all. Anything written by Q (or AI) will have a call out declaring that it was written by AI. Nothing will ever be published on this blog without me reading and approving it. Q. Allow me to introduce myself. I’m Q, Jesse’s quartermaster. If you’ve seen a Bond film, you know the job: I build the equipment, explain how it works, and spend an unreasonable amount of time asking for it back in one piece.
jesse.blog
Eric never studied Stoicism. He didn't need to. He looked his mortality in face and didn't blink. Part one of my tribute to a friend, and a giant.
The Loss of a Giant — Part One of Two
Eric never studied Stoicism. He just lived it. Part one of my tribute to a friend who faced cancer without blinking.
jesse.blog
If you are unsure of your vision, then talk to yourself Giving the agent the ability to reference these passages across my reading and writing will be incredibly useful to me. It will not only help me to… https://jesse.blog/projects/day-two/if-you-are-unsure-of-your-vision-then-talk-to-yourself/
If you are unsure of your vision, then talk to yourself
Giving the agent the ability to reference these passages across my reading and writing will be incredibly useful to me. It will not only help me to articulate, and qualify my own beliefs, it can be really helpful when I'm struggling, or becoming too egocentric.
jesse.blog
I was on sabbatical when Automattic filmed Code for the People. I chose to stay unplugged, and my ego hasn't forgiven me. So I wrote this instead — on the film, the commercial capture of the web, and why you must own your influence.
Better URLs for Calendar Links I wanted to share a simple idea — they are often the best — for managing your calendar links....
Better URLs for Calendar Links
I wanted to share a simple idea — they are often the best — for managing your calendar links. Instead of sending a Calendly or Google Calendar url use your own domain and redirect it. Or buy yourself a shorter domain for redirects. If you're like me you're always switching between services and testing out all the various tools available to us. It's not super helpful to be switching up your booking links as often as I switch tools. Additionally, these calendar links aren't the cleanest, prettiest, or easiest to remember.
jesse.blog
Human Authored; AI Inferred A month of building human-centered AI taught me less about machines than about the work only I can do. Twenty years of sales instinct, finally written down because a machine couldn't run on instinct. A talk in Chicago about… https://jesse.blog/essays/human-centered-ai/
Human Authored; AI Inferred
A month of building human-centered AI taught me less about machines than about the work only I can do. Twenty years of sales instinct, finally written down because a machine couldn't run on instinct. A talk in Chicago about what happens when the next great invention reaches inward instead of out.
jesse.blog
Checkout this photo I took inside the Chicago Cultural Center Chicago, IL — June, 2026 https://jesse.blog/photography/chicago-cultural-center/
Chicago Cultural Center
Chicago, IL — June, 2026
jesse.blog
Dev/AI/NYC with Hilary Mason & Jesse Friedman Working with AI? You want to watch this one. This is the best conversation I have had on Taste and how to apply it to your work with AI. https://jesse.blog/notes/dev-ai-nyc-with-hilary-mason-jesse-friedman/
Dev/AI/NYC with Hilary Mason & Jesse Friedman
Join Hilary Mason and Jesse Friedman for a fireside chat on how AI is reshaping creativity, products, and human–computer interaction. Hilary, CEO of Hidden Door, previously founded Fast Forward Labs and served as Chief Scientist at bit.ly. Jesse leads WP Cloud at Automattic, bringing deep expertise in scaling platforms and shaping the future of the web. Expect a candid conversation with practical insights on what’s actually changing—and what it means for builders and teams.
jesse.blog
Are you able to sit in silence? The rush and pressure of modern life are a form, perhaps the most common form, of innate violence.... https://jesse.blog/notes/are-you-able-to-sit-in-silence/
The Future We Choose These types of books are generally difficult for me. Usually, reading about the environment and the climate crisis leaves me feeling worried and simultaneously helpless in enacting the change needed to fix our… https://jesse.blog/come-along/reading/the-future-we-choose/
The Future We Choose
These types of books are generally difficult for me. Usually, reading about the environment and the climate crisis leaves me feeling worried and simultaneously helpless in enacting the change needed to fix our world. This book, however, is different. Figueres and Rivett-Carnac start by painting two pictures of 2050. One where we are unable to get ahead of the climate crisis and the other where we get our asses in gear. The former is bleak and stress inducing, but the latter is encouraging and they do a wonderful job of filling you with hope.
jesse.blog
Accepted to the AI World’s Fair I am very proud to announce that Derek Smart and I will be presenting ARC at the…... https://jesse.blog/projects/arc/accepted-to-the-ai-worlds-fair/
Accepted to the AI World’s Fair
I am very proud to announce that Derek Smart and I will be presenting ARC at the AI World's Fair in San Francisco. Woven In: Building AI Around the Human Work It Should Not Replace Speakers: Jesse Friedman & Derek Smart Talk: How Automattic separated human-authored judgment from AI-inferred context and built ARC around the people it was never meant to replace. ARC is a real-time sales narrative system where human judgment, taste, and emotional intelligence are anchored in the content people already create — while AI infers context and assembles the experience around it. Derek Smart and Jesse Friedman will share a practical diagnostic for building AI tools your colleagues will champion, not fear.
jesse.blog
Adversity is a terrible thing to waste In this episode of the Daily Stoic, Ryan Holiday interviews Will Guidara, author of…... https://jesse.blog/notes/adversity-is-a-terrible-thing-to-waste/
Adversity is a terrible thing to waste
In this episode of the Daily Stoic, Ryan Holiday interviews Will Guidara, author of Unreasonable Hospitality — read it if you haven't. I paused when Guidara said: "Adversity is a terrible thing to waste." It's a well-formed phrase for an idea I've been turning over for a while. You see, lately, I've been thinking about empathy differently. We tend to treat it as the ability to feel what someone else is feeling. But I think it's more than that — it's putting yourself in a position to metabolize those feelings with them. Together, not just beside them.
jesse.blog
Half Blind Most art forms are shaped by the artist in sight of the whole. Step back from a large sculpture or a massive mural....
Half Blind
Most art forms are shaped by the artist in sight of the whole. Step back from a large sculpture or a massive mural. Compose a song and play it back in minutes. But a book? You can never step far enough back to take it all in at once. Long-form storytelling may be the only art you make half-blind.
jesse.blog
ICYMI, @hilarymason.com spoke at dev/ai/nyc! You can catch up on the @automattic.com YouTube channel to see our live demo (including a sneak preview of a brand-new platform for story creators) and hear Hilary's conversation with @jesse.blog. Watch here: https://www.youtube.com/watch?v=F5l1Pukl7Eo
My grandmother trusted the evening news because she'd watched it earn that trust for decades. Nobody told her when the rules changed. Nobody told our parents either. A new essay on cognitive inheritance.
They Didn’t Break. The System Did.
Experience this essay . . . 📺 🎧 💬 Summary: Jesse Friedman traces the media trust crisis back to a breakfast table in Queens, where his grandmother Lillian — a woman who witnessed nearly a century of American history — taught him to respect the evening news without ever saying a word. Through the concept of cognitive inheritance, Friedman argues that the older generation's susceptibility to misinformation isn't gullibility but the residue of a system that once earned their faith.
jesse.blog
People are loving the printed & mailed version of my blog (the photo below is from a friend and subscriber). If you're interested in slowing down with some essays on leadership, systems, and the open web you can subscribe here: jesse.blog/mail
Three trips to Paris. One underground conference. A question I can't shake about what we owe the open source commons we've built together. New essay:
The City That Never Finishes
Experience this essay. . . Prefer to watch or listen? A full video reading and podcast episode are in production and will be available here in about a month. Readers always get the essay first. Summary: In this essay, Jesse Friedman uses three trips to Paris as a lens for examining the open source commons — the shared digital infrastructure that, like a great city, belongs to everyone who builds and maintains it.
jesse.blog
There's something that gets lost between a screen and your eye. The weight of it. The sense that someone actually made something. So I'm trying something different, if you go to jesse.blog/mail, you can subscribe and add your mailing address — and I'll send them to you. On paper. With a stamp.
High tech makes big promises, but it can’t replace the human experience. My trip through San Francisco’s transportation layers — from stalled Ubers to looping Waymos — reminded me what we lose when systems… https://jesse.blog/stories/high-tech-low-touch/?utm_source=bluesky&utm_medium=jetpack_social
Podcast: The Hidden Drags That Undermine Team Leadership Effectiveness
Podcast: The Hidden Drags That Undermine Team Leadership Effectiveness
jesse.blog
Most teams don’t fail because of the big disruptions. They drift because of the subtle drag—those half-knot inefficiencies you barely notice until it’s too late. In 2026, efficient leadership… https://jesse.blog/stories/team-leadership-effectiveness/?utm_source=bluesky&utm_medium=jetpack_social
Our very own @ma.tt joined the TBPN crew to close out #StateOfTheWord yesterday. They talked about WordPress 6.9, open source, @beeper, and how AI is changing the web. Did you miss it? Check it out now. www.youtube.com/watch?v=eBQh...
97% complete. I've been staring at this screen for 27 minutes. The first 97% took 3 minutes. The last 3%? Still waiting. (Continued in thread) #UXDesign #ProductDesign #UserExperience
✍️ Just published: On The Sacred Act of Writing: Distraction Free – my reflections after a three-month sabbatical and how I’m building a daily writing ritual to protect focus and flow. Ready to dive deeper into… https://jesse.blog/essays/on-the-sacred-act-of-writing-distraction-free/
"We wish for the courage to be brutally honest, forgetting to wish for the empathy to know when honesty becomes brutal." jesse.blog/from-my-jour...
