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Wisdom Well

Chip Conley's daily blog:
Thoughts on the art of living

The Blessing of Your Chosen Torture

There’s a moment in an interview between Jerry Seinfeld and Howard Stern where Seinfeld offers a line that has been rattling around in my head ever since author Dan Pink mentioned it in a recent MEA workshop: “The blessing in life is when you find the torture you’re comfortable with.” It’s funny. It’s uncomfortable. And ...

Chip Conley
Chip Conley
May 4th, 2026

The Blessing of Your Chosen Torture

Chip's Tips

Chip’s posts on midlife wisdom

Explore Chip Conley's insightful reflections on navigating midlife challenges with grace and resilience. His posts offer practical advice and empowering perspectives for thriving during life's pivotal transitions.

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Most Personal Stories

Delve into the deeply moving narratives that capture the essence of human experience. These intimate stories offer a window into life's most poignant moments and personal triumphs.

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Most Popular Wisdom Well Post

Discover the essential advice from Chip Conley that has resonated the most with readers navigating midlife transitions. Tap into a wellspring of wisdom to transform challenges into growth and newfound clarity.

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The Three Kinds of Snobbery (and the One You’re Most Prone To)

David Brooks offers a helpful framework when he describes three kinds of snobbery that quietly organize modern life: dominance, success, and virtue. The uncomfortable truth is that almost all of

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Chip Conley

January 12, 2026

Guest Post: The Alchemy of Becoming: What Medieval Gold-Seekers Knew About Becoming Human

This morning, coffee in hand and watching the light change outside my window, I found myself thinking about alchemy—that ancient pursuit of transforming base metals into gold. Most dismiss it

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Ray Kennedy

January 11, 2026

Guest Post: The Future You has the Answers

There’s a moment in midlife when the old maps stop working. All the strategies that got us here (striving, accumulating, proving, optimising) don’t seem to point us anywhere meaningful. We

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Carlos Saba

January 10, 2026

Is This The Year You Commit to a Meditation Practice?

Meditating in the sun after swimming laps in Baja. “All of humanity’s problems stem from man’s inability to sit quietly in a room alone.” – Blaise Pascal As our first

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Chip Conley

January 9, 2026

“That’s a Wrap!” Highlights of the 2nd Annual MEA Film Fest

I came face-to-face with my passionate ambition last month. When I love something, I throw all of my being into it – whether that be my dog, a political belief,

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Chip Conley

January 8, 2026

It’s Time for You to Become a Beginner Again

Today, we published the 44th episode of my podcast The Midlife Chrysalis with one of our Wisdom Wednesday conversations with me and MEA’s CEO Derek Gehl (my interviews with thought

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Chip Conley

January 7, 2026

Meditation and Yoga Went Mainstream – Is Co-Living Ready to go Mainstream?

But, today, it seems every Tom, Dick, and Sally have taste-tested mindfulness with a side of psychedelics. And, yet, where and how we reside is still stuck in the time

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Chip Conley

January 6, 2026

Celebrating 8 Years of MEA: From Idea to Global Movement

This photo in Baja was taken nine years ago when Oren and I’d just finished renovating our hacienda home and the idea of MEA wasn’t even in my consciousness. You

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Chip Conley

January 5, 2026

Guest Post: The Hardest Transition Can be the Most Beautiful

It was a treat getting to know Adriana at the Liz Gilbert and Tererai Trent workshop in 2024 and I appreciated her vulnerability in this post. Liz and Tererai are

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Adriana Haas

January 4, 2026

Guest Post: What I Learned Writing the Book I Never Thought I’d Write

Hell, I barely thought I was allowed to. I’m not famous. I haven’t cured cancer. I haven’t built a Fortune 500 company (yet). I’m just a regular woman who’s survived

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Michelle Marquis

January 3, 2026

Guest Post: A Five-Star Life and What It Teaches Us About Wealth

I recently attended the celebration of life for a high school friend, Jim. He was the kind of person who made rooms brighter—warm, lovable, laughing, courageous. Everyone had a “Jim

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Tim Croak

January 2, 2026

Guest Post: The Real Cost of Playing it Safe in Midlife

 I’ve chosen Susan’s catalytic guest post as a great way to start the new year, a time meant for action, not just contemplation. Hope you get to listen to the

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Susan Cole

January 1, 2026

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