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.

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.

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.

Chicago, IL — June, 2026

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.

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.

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.

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.

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.

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.

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.

We wish for the courage to be brutally honest, forgetting to wish for the empathy to know when honesty becomes brutal. - Jesse Friedman

Times Square has an unnatural resonance, one you cannot become attuned to. It hums from electrified currents pumped into sky-high advertisements. It buzzes from worker bees shuffling across cement pat...

Times Square has an unnatural resonance, one you cannot become attuned to. It hums from electrified currents pumped into sky-high advertisements. It buzzes from worker bees shuffling across cement pathways. It aches as black and yellow caravans ebb and flow through its arteries. But there is nothing natural here. Nothing grows here. It is a completely artificial hive colonized by none whom belong to it. 

I used to encourage my teams and colleagues to 'Celebrate Failures.' Otherwise, we hide shared learnings from one another when we sweep mistakes under the rug in shame. The truth is, we all know this, we all fail from time to time. What's important is learning and adapting. My idea behind celebrating failures was to remove the stigma around failing, while finding comfort in the vulnerability required to talk openly about it.

“I make plans in decades. This is not a huge deal to me,” said the WordPress founder.