The Journal

Essays on the work of the second half of life. Honest, sometimes hard to hear, always written from inside the climb. Alongside them, weekly Field Notes read across the thinkers who shape our work.


  • Field Notes: Care Hard, Hold Loose

    Field Notes: Care Hard, Hold Loose

    Brad Stulberg says stop playing it cool and care out loud. Steve Magness says caring too hard can choke you. Read with Michael Easter’s guest Ravi Gupta and Rich Roll’s conversation with Jim Morrison, they add up to one idea: care fully, and hold it loosely enough to…

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  • Field Notes: Stop Auditioning for Your Purpose

    Field Notes: Stop Auditioning for Your Purpose

    Chip Conley, Brad Stulberg, Vivek Murthy, and a newsletter writer working through James Hollis all took on the same midlife itch this week: the feeling that you should know what your life is for by now. Read together, they suggest purpose isn’t found by searching harder. It’s walked…

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  • Field Notes: Witnessed, Not Fixed

    Field Notes: Witnessed, Not Fixed

    This week, Scott Galloway, Esther Perel, psychologist Sam Carr, and poet Mark Nepo all circled the same problem: men surrounded by people and still alone. They disagree about whether loneliness can be cured, and the disagreement is the useful part.

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  • Falling Upward, Slowly

    Falling Upward, Slowly

    Richard Rohr says the two halves of life are separated not by age but by a fall. Something stops working, and the failure turns out to be the doorway. A report from the far side of a year spent falling on purpose.

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  • What Are You Choosing Not to See?

    What Are You Choosing Not to See?

    I planned to ask a room of accomplished people what they’d do if they gave themselves permission to take risks. A week before the retreat, I realized it was the wrong question. These were people who’d taken risks their whole lives. The right question was harder.

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  • The Second Sunrise

    The Second Sunrise

    Last week, seventeen of us drove north to a summer camp on a lake in Wisconsin and spent five days asking each other questions we’d stopped asking ourselves. I can’t tell you what was said in the circle. I can tell you what the place did to us.

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  • In Defense of Discomfort

    In Defense of Discomfort

    We’ve engineered difficulty out of our lives so completely that we now pay to get it back. That’s not a joke about exercise bikes. It’s the most practical insight I know about staying alive in the second half of life. Next month, a group of us is testing…

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  • The Quiet Distance

    The Quiet Distance

    The dangerous season of midlife doesn’t announce itself with a crisis. It arrives as a gap between the life you built and how it feels to live it. Most of us respond by building more. That’s the one move guaranteed not to work.

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  • The Permission You’re Not Giving Yourself

    The Permission You’re Not Giving Yourself

    I’m fifty-five years old. I’m the managing partner of a national law firm. And every July, I spend a month as a summer camp counselor in the north woods of Wisconsin. Everyone thought I’d lost my mind. It was the sanest thing I’d done in years.

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The Trailhead Letter

Each new essay, delivered to your inbox. Nothing said in a Trailhead circle, and nothing for sale.

Every transition has a trailhead.

Trailhead is a nonprofit. No one is paid, and expedition costs are shared at cost among campers. What is said in a Trailhead circle stays in the circle.

Go Trailhead, Inc. · St. Louis, Missouri