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The Paradox of Mastery

Episode 327

In 1921, an Austrian philosopher named Ludwig Wittgenstein concluded his Tractatus Logico-Philosophicus with the following passage:

“My propositions a…

1 year, 2 months ago

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7 Reflections from a “Think Week” Retreat

Episode 326

Last week, I went on my first “Think Week” retreat.


Three days. Limited connectivity. No meetings. Just reading, deep conversations, journaling, and t…

1 year, 2 months ago

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The Perspective Shift That Changes Everything

Episode 325

One of my favorite quotes comes from ​Siddhartha​ by Hermann Hesse:

“We are not going in circles, we are going upwards. The path is a spiral; we have …

1 year, 3 months ago

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The Dunning-Kruger Effect: The Psychology of Overconfidence

Episode 324

Have you ever grown frustrated by the observation that the people who know the least seem to be the most confident in their knowledge?


You're not craz…

1 year, 3 months ago

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The Speech That Changed How I See the World

Episode 323

Exactly 20 years ago, on May 21, 2005, author David Foster Wallace stood before the graduating class at Kenyon College and delivered the annual comme…

1 year, 3 months ago

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The Say-Do Gap: A Question to Reset Your Life

Episode 322

Here's a question I like to ask myself when I feel stuck:


If an outside observer watched me for a week, how serious would they say I am about achievin…

1 year, 3 months ago

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The Hidden Bias Keeping You Stuck

Episode 321

We all do it.


We stay in jobs that drain us. We cling to relationships that no longer bring us energy. We hold onto possessions, identities, and goals…

1 year, 3 months ago

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A Letter to My Son on His 3rd Birthday

Episode 320

My son turns three years old this week.


Over the last few months, I've grown increasingly excited by the idea of writing him a series of letters he ca…

1 year, 3 months ago

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The Question That May Change Your Life

Episode 319

There’s a story about Apple founder Steve Jobs that I love:


When he was 12 years old, he cold-called Bill Hewlett—co-founder of the pioneering technol…

1 year, 3 months ago

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3 Reasons to "Sell" in Life

Episode 318

Last week, investor Bill Ackman hosted a fireside chat conversation in Omaha in front of a standing room only crowd of 500+ investors.

Ackman was join…

1 year, 3 months ago

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