jesse friedman

My grandmother trusted the evening news because she’d watched it earn that trust for decades. Nobody…

Mon, 16 Mar 2026 18:39:27 -0400

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.

Three trips to Paris. One underground conference. A question I can’t shake about what we owe the…

Mon, 09 Mar 2026 09:35:34 -0400

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

There’s something that gets lost between a screen and your eye.

Fri, 27 Feb 2026 13:35:50 -0500

There’s something that gets lost between a screen and your eye.

Not the idea — the ideas make it through fine — but something else. The weight of it. The sense that someone actually made something.

So I’m trying something different.

I write essays. Long ones, about cities and open source and the way technology changes how we move through the world. And 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.

You can read it on your porch. Fold it up. Spill coffee on it.

And if something moves you — a thought, a pushback, a story of your own — you can write me back. And I’ll write back.

It’s slower. That’s sort of the point.

jesse.blog/mail

Churchill by Paul Johnson

Wed, 28 Jan 2026 11:53:53 -0500

༺ Recommend ༻

Continue reading Churchill by Paul Johnson

Churchill by Paul Johnson

4 Hour Work-week by Tim Ferriss

Fri, 16 Jan 2026 21:32:08 -0500

༺ Recommend ༻

Continue reading 4 Hour Work-week by Tim Ferriss

4 Hour Work-week by Tim Ferriss

High tech makes big promises, but it can’t replace the human experience. My trip through San…

Wed, 17 Dec 2025 10:08:28 -0500

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 forget the people they serve.
Read the full story:

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Podcast: The Hidden Drags That Undermine Team Leadership Effectiveness

Thu, 04 Dec 2025 18:42:13 -0500

Podcast: The Hidden Drags That Undermine Team Leadership Effectiveness

Most teams don’t fail because of the big disruptions. They drift because of the subtle drag—those…

Thu, 04 Dec 2025 10:30:02 -0500

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 means learning to spot and correct the imbalance before it slows the whole ship.
Read the full piece:

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✍️ Just published: On The Sacred Act of Writing: Distraction Free – my reflections after a…

Tue, 18 Nov 2025 07:44:12 -0500

✍️ 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 distraction-free writing?

#writing #focus #distractionfree #writingritual #flow

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I didn’t think it could get any better. The warm mornings, a blank page, a hot coffee. And then I…

Sat, 05 Jul 2025 03:26:24 -0400

I didn’t think it could get any better. The warm mornings, a blank page, a hot coffee. And then I remembered, I had a box pressed Melanio Gran Reserva Limitada in my bag.

Mon, 30 Jun 2025 02:21:35 -0400

Aimez L’amour Queer à Paris

We wish for the courage to be brutally honest, forgetting to wish for the empathy to know when…

Sat, 21 Jun 2025 09:32:11 -0400

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

https://jesse.blog/from-my-journal/brutal-honesty/

Banana

Thu, 08 May 2025 13:37:01 -0400

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.

You’re surrounded on all sides by marvels of human creation. While bees race to capture portraits of themselves amongst showcases of capitalistic modernity. Characters in a play happily portray their own disconnect.

Across Broadway, coming towards me is a young man and his friends. The small tattoos his face and his short curly hair are an obvious display of confidence in it’s defiance to cultural norms. In his hand, a banana.

He peels the banana, extracts the fruit and drops the peel to the ground. He laughs, though not about the banana. It’s a natural laughter, a display of the connection he has to his friends.

I look down at the banana peel. It grew out of the earth, traveled across the globe, and was carried to this spot to adopt its new station as a natural element in an unnatural world.

Litter.

I make eye contact with the young man. He senses my response and prepares for a delivery of defiance.

“Have you never seen a cartoon?” I said.

The tension in his hands fade. His jaw unlocks. He smiles. I subverted his expectations, using humor to explain the dangers of a banana peel on a busy walkway.

He did not return to claim his litter. The banana peel remained. A natural element in an unnatural world.

It’s only a mistake if you make it twice

Thu, 27 Feb 2025 12:33:48 -0500

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…

It’s only a mistake if you make it twice

A Note on Ego

Thu, 20 Feb 2025 09:23:00 -0500

Recently I have been more in tune with, and listening to the impact of Ego on our imagination. Our early childhood was Ego-less. We felt no shame running naked through our backyards, waving our arms, and singing songs. As children we also experience no limitations in our imagination. We were in tune with nature and the universe. We stared up at the clouds and crafted beautiful worlds and…

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My creativity is literally being smothered by greed.

Tue, 18 Jun 2024 18:15:12 -0400

Fed up with being controlled by corporate tech? I share my experience with @HP’s Instant Ink — a system more about profit than user freedom. We need to demand better! #TechControl #UserExperience

It’s days like today that make me want to move to the wilderness and never return. The current state of what we call innovation is so commercially driven it’s killing real innovation and creativity. Automattic and a few other companies are exceptions to this rule but the global trends are definitely moving in the wrong direction.

There are dozens of companies focusing their R&D on ways to…

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I love working at Automattic (the company behind Tumblr), but one of the best benefits is not…

Thu, 01 Feb 2024 14:22:41 -0500

I love working at Automattic (the company behind Tumblr), but one of the best benefits is not working at Automattic. We have an unlimited vacation policy which makes it easy to work your butt off when you know you can just take a day for yourself. Today I’m literally just hanging out, unplugged, and relaxed. First stop on the day off tour is a cigar and an na Beer at Hill and Harbor. Then I have sushi and a movie planned for later today.

I’m trying out some AI generated video content. Seeing what I can do to turn some blog content into…

Sun, 28 Jan 2024 17:30:40 -0500

I’m trying out some AI generated video content. Seeing what I can do to turn some blog content into video format.

Think of this as a rough cut of what I’m trying to get done. Bear with me, it’ll get better.

Teenage Mutant Ninja Turtle ChatGPT Fun

Sat, 24 Jun 2023 18:36:11 -0400

My daughter was having some fun with ChatGPT and I absolutely loved this prompt and response. The use of metaphors and character style in this explanation is truly brilliant. I don’t know that most people understand the real genius here.

Explain the difference between a president and a prime minister. Use a comical tone of voice and use the mannerisms of Michaelangelo, the Teenage Mutant Ninja…

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#luxembourg #castle #chateau (at Château de...

Sat, 18 Mar 2023 11:22:44 -0400

#luxembourg #castle #chateau (at Château de Vianden)
https://www.instagram.com/p/Cp72VxouZlV/?igshid=NGJjMDIxMWI=