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Wisdom Well has

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Chip's daily reflections on midlife and the questions that matter most in this chapter now live at chipconley.substack.com. The archive of all his previous posts stays right here. Join us on Substack for a daily dose of perspective on the life you're actually living.

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Want to Become “Boommates”?

Several generations living under one roof would help ease the housing crunch and the loneliness epidemic affecting half of U.S. adults. It would also cut global warming emissions. Denser living

Chip Conley

April 29, 2025

Rolling with Rich

You can watch and listen to it HERE. It was inspiring to ask Rich a few questions since he’s normally doing all the inquiries to his guests. Here are the

Chip Conley

April 28, 2025

Becoming Un:Stuck

Why I Wrote “Un:Stuck: Helping Teens and Young People Flourish in an Age of Anxiety” ‘What makes you feel most alive?’ is a question I continue to ask my children.

Kate O’Brien O’Brien

April 27, 2025

The Liberation of Creative Potential: Exploring the New Frontier of the Bonus Round

Our cultural assumptions about creativity tend to lionize youth—think of Mozart composing at the age of five or how we celebrate the disruptive energy of Silicon Valley’s “under 30s.” Yet

Pam McLean, Ph.D

April 26, 2025

How Might You Celebrate Your Next Birthday Differently?

I love this recent Huffington Post article about Megan Vered who wrote to a wide circle of friends that she’d like to celebrate her 70th birthday doing 70 really interesting

Chip Conley

April 25, 2025

Two Conservatives Offer Some New York Times Wisdom

But, I found Ross Douthat’s column from this past weekend, An Age of Extinction is Coming, and David Brooks’ What’s Happening Is Not Normal. America Needs an Uprising That Is

Chip Conley

April 24, 2025

Why You Flourish in Your 50s

There’s social science evidence showing that younger people consistently and markedly overestimate how satisfied they will be in five years, while older people underestimate future satisfaction. Researchers have found that

Chip Conley

April 23, 2025

How Are You Training to Become a Modern Elder?

Steven replied, “If we’re lucky, we’ll all get older, but only a few of us will become a true elder.” I laughed it off, but within a half-dozen years, I

Chip Conley

April 22, 2025

A Window into Your Wisdom

The eyes may be the window to one’s soul, but the gut is the window to one’s wisdom. The gut is often called our “second brain” for good reason—it holds

Chip Conley

April 21, 2025

Are You Having a Near-Life Experience?

I see them everywhere: people standing in elevators, at bus stops, in line at grocery stores—their eyes fixated on their phones. And yes, I’m guilty of this too. I call

Karen Salmansohn

April 20, 2025

What Does It Mean to Truly Listen? It Means Listening With Our Eyes.

There’s an old story of a child who comes home and says, “mom, mom mom…” (for those of us with kids, we’ve been there). Mom, of course, is busy with

Daniel Gropper

April 19, 2025

Before Death, Depth

We don’t need to live longer. We need to live deeper. And that doesn’t require a plane ticket or a new guru. It starts with this moment. This breath. This

Chip Conley

April 18, 2025

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Wisdom Well has

moved to Substack

Want to Become “Boommates”?

Rolling with Rich

Becoming Un:Stuck

The Liberation of Creative Potential: Exploring the New Frontier of the Bonus Round

How Might You Celebrate Your Next Birthday Differently?

Two Conservatives Offer Some New York Times Wisdom

Why You Flourish in Your 50s

How Are You Training to Become a Modern Elder?

A Window into Your Wisdom

Are You Having a Near-Life Experience?

What Does It Mean to Truly Listen? It Means Listening With Our Eyes.

Before Death, Depth

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