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They Didn’t Break. The System Did.
I want to start this journey towards empathy with a trip back to 1989 in Queens, New York. I am sitting down to eat the breakfast my grandmother, Lillian, has prepared for me. I am nearly 7. She, nearly 75. Breakfast is cottage cheese, cantaloupe, and rye toast. She thrived for almost one hundred years…
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The City That Never Finishes
In the center of Paris, at her beating heart, burns a furnace of fire and flame. A white-hot mass with a gravitational pull on those susceptible to her charm. This magnetic force draws you in, warms your soul, and if you are lucky enough to surrender to it, you become one with her. And when…
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High Tech, Low Touch
A journey through San Francisco’s transportation layers—from legacy taxis to runaway Waymos—and what it reveals about empathy, experience, and the systems we’re building
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The Hidden Drags That Undermine Team Leadership Effectiveness
In 2026, the difference between thriving and surviving will come down to efficiency. And I’m not referring to the obligatory mechanical kind powered by automation, which we are all going to have to adopt, but the human kind: the ability to lead a lightweight, focused team that cuts through challenges and adapts to challenges on…
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On The Sacred Act of Distraction Free Writing
I am back from my three-month sabbatical; an amazing benefit Automatticians receive every 5 years. I spent a significant portion of that time reading and writing (distraction free writing that is). After some accounting I put the count north of 100,000 words. Some went towards a thriller I’m writing. Others went to journal entries, reflections…
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brutally honest
We wish for the courage to be brutally honest, forgetting to wish for the empathy to know when honesty becomes brutal. – Jesse Friedman
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Banana
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…
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It’s only a mistake if you make it twice
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…
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A Note on Ego
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…
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No, I’m not that Jesse Friedman.
For over a decade, I, Jesse Friedman, have struggled with the perception of my identity. While this is not a valid identity crisis—I know who I am—it has been challenging to manage the reactions of followers who “Google me.” My efforts to shine as an expert have been overshadowed by the depravity and evil contributions…
Things I Swear By:
Things I actually use, read, eat, and carry. No paid placements. Occasionally an affiliate link — which helps keep this blog running — but the list doesn’t change based on that. If it’s here, I stand behind it.
There’s something that gets lost between the screen and the eye.
Not the idea—the ideas make it through just fine—but something else. The weight of it, maybe. The sense that someone sat down and made something, and now you’re holding it.
I’ve been thinking about that, and so I’m trying something a little different. Sending my essays in the mail. Real paper. A stamp. The whole thing.
You can read it on the 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 back, and if you do, I’ll write back.
Or, subscribe for just the newsletter:
It’s slower; that’s the point. . .