Category: Essays

September 2, 2025

How to Read More Books

A recent headline has been bouncing around the internet: reading books for fun is down 40% over the past 20 years. That’s as unsurprising as it is sad. Because books…
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August 25, 2025

I Got to Say Goodbye: Practical Musings on Mortality

On Friday August 15th, my grandma passed away peacefully in her sleep at the age of 95. I had driven to Massachusetts a few days earlier, and my father and…
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August 10, 2025

Keep Changing, You Just Get More Who You Really Are

“Well, it’s easy. I just threw away all the parts that weren’t ‘Steve.’” I had been sitting with my friend Josh Kaufman in Colorado. I was struggling to make progress…
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August 4, 2025

Be Careful of the Past You Never Knew (Nostalgia vs. Anemoia)

Ever looked at a photo from a bygone era and wondered what it would be like to live in that moment? Congratulations, you experienced something called “anemoia.” It’s kind of…
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May 27, 2025

Via Negativa: Addition by Subtraction

In a recent newsletter, I talked about how life has become “unbundled” (split into individual parts like cable TV becoming a dozen streaming services). We now have separated work, exercise,…
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May 19, 2025

5 Short Stories from My Life: Hope, Fear, and Technology

Here are 5 short stories from my adventures over the past month that perfectly encapsulate my hopes, dreams, fears, and concerns about where we’re at as a society in 2025……
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April 20, 2025

The Beauty of Being Broken: Kintsugi

Sometimes, I stumble across a concept that’s so beautiful it moves me to tears. I can’t quite remember how or when I found this particular concept initially… But let me…
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February 25, 2025

Why You NEED a Big Why

Entrepreneur Peter Barton was on top of the world. Until he wasn’t. Barton lived a life everybody dreamed of, took pretty damn good care of himself, and was a great…
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February 18, 2025

Mobsters, Knights, and Samurai, oh my! What’s YOUR Code?

In 2007, Italian police arrested Salvatore Lo Piccolo. This dude was an actual boss from the real life Sicilian Mafia. As they explored his house, they stumbled across what they…
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February 13, 2025

Choose Uncomfortable Growth over Comfort

Stephen Wilson Jr. was a scientist working for Mars, Inc. (Yeah, the Candy company). One day, his boss pulled him into an office and said something that changed his life:…
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