Category: Uncategorized

  • 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.

    Falling Upward, Slowly
  • 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.

    What Are You Choosing Not to See?
  • 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.

    The Second Sunrise
  • 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 it in the Northwoods.

    In Defense of Discomfort
  • 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.

    The Quiet Distance
  • 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.

    The Permission You’re Not Giving Yourself

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