There’s a particular kind of anxiety that shows up after success. You’ve done the things. The career worked. The kids are grown, or close to it. And a question that used to feel abstract starts showing up at 3 a.m.: what is all this for?
Chip Conley has a name for it. In “Do You Have Purpose Anxiety?”, posted October 28 to his Wisdom Well newsletter, Conley says he sees it constantly among the accomplished people who come to the Modern Elder Academy. They expected achievement to deliver meaning. It didn’t. Now they feel they should have a grand purpose, they don’t know what it is, and the not-knowing has become its own source of distress.
He wasn’t the only one working this ground. In a single week, four very different voices in the Trailhead Library took up the same question from different sides. They don’t fully agree. The places where they rub against each other are the useful part.
The Search Is Part of the Problem
Conley’s core claim is counterintuitive. The hunt for purpose can make things worse. He cites research by Larissa Rainey at the University of Pennsylvania, which he summarizes this way: most people want a purpose, but searching for one often produces anxiety, at any age, and that anxiety takes a toll on well-being.
His answer is to change the frame. “Purpose isn’t a treasure hunt. It’s a practice,” he writes. He separates the grand, capital-P calling from smaller purposes like mentoring someone, caring for family, or making something beautiful. He points out that purpose shifts over a lifetime, so what lit you up at 35 may not at 65. And he draws a line between purpose and legacy. Legacy is what you leave behind. Purpose is what energizes you and lets you contribute now.
Then he swaps the big question for three smaller ones. What makes me feel most alive? Who or what do I care deeply about? Where can my gifts meet a need?
That’s a relief for a lot of people. It lowers the stakes. But on its own, it could also sound like permission to settle. That’s where the next voice comes in.
When the Emptiness Is a Message
On October 31, the Substack newsletter Why & So What published “Sunk Loyalty,” a reflection on a recent conversation between the physician Rangan Chatterjee and the Jungian analyst James Hollis. Hollis has spent decades arguing that midlife emptiness isn’t a breakdown. The newsletter’s writer, who signs off as Ted Cash, sums up that view in one line: “The emptiness may not be a malfunction at all.” In Hollis’s telling, the ego builds a provisional identity early in life to earn love and safety. At some point the psyche stops supporting it. The flatness people feel in midlife is the signal.
The writer then adds two ideas Hollis doesn’t use. From the philosopher René Girard comes the notion that much of what we want is borrowed from people we admire, then experienced as our own. From economics comes path dependence: early choices build structures, like a salary, a house, and a web of obligations, that make change expensive long after the original reasons fade. Together, he argues, they explain both how a borrowed life gets built and why it’s so hard to leave. He calls the pull to stay “sunk loyalty,” a sense of duty to a life held in place by what it has already cost.
Here’s the tension with Conley. Conley says relax, purpose is smaller and more fluid than you think. Hollis, through this writer, says the discomfort is real and it’s asking for something. Both can be true. The flatness may not mean you need a grand new mission. It may mean some of what you’re doing was never yours to begin with.
The newsletter offers a practice that bridges the two, a seven-day “Vitality Audit.” Each evening, log the three activities that drained you most and mark each one as something that enlarges you or diminishes you. On day seven, name whose expectations sit behind the ones that diminish. Within 72 hours, make one small change. Reclaim one inch. The writer is careful to add that persistent depression needs medical care, not just reflection.
Take the Guitar Off the Wall
Brad Stulberg comes at it from the other side. In “It’s Not Cliché to Keep Dreaming, It’s Actually Essential,” posted October 27, he tells the story of the country singer Stephen Wilson Jr. Wilson boxed as a kid in southern Indiana, studied microbiology, and spent years in research and development at Mars. At 37 he left to make music. About a decade later he has four CMA nominations and is on a world tour. He’s 47.
Stulberg, who recently turned 40 and admits to feeling burned out, draws three lessons. Progress isn’t linear, so giving up what you love as you get older is a mistake. Don’t protect yourself into inaction. And don’t let the fear of looking foolish trade away growth for comfort. His image for all of it is Wilson’s beat-up Craigslist guitar: “Guitars are meant to be played, not hung up on a wall.”
Stulberg is the voice for dreaming bigger. Read closely, though, his story fits Conley’s. Wilson didn’t find his purpose on a vision quest. He kept playing a cheap guitar for years while doing something else. The leap at 37 came after a long practice, not instead of one.
Vivek Murthy adds a caution that keeps all this from becoming another performance project. In “Why Trying Harder Isn’t Always the Answer,” posted October 29 to his Staying Human newsletter, the former Surgeon General writes that he used to assume more effort was the answer to any difficulty. Now he sees its limits. Prolonged stress degrades judgment and flexible thinking, and rumination keeps the stress response running long after the problem has passed. He recalls an ICU attending from his residency who taught him that sometimes the right move is not to intervene, because every intervention has costs. “Sometimes, making progress requires loosening our grip,” Murthy writes.
That’s a useful warning for anyone tempted to attack purpose the way they attacked their career. You can’t grind your way to meaning. Sometimes the work is to stop, stand still, and notice what the resistance is telling you.
Trails Are Made by Walking
Read side by side, these four are saying something none of them says alone. The search for a single grand purpose tends to backfire. The emptiness that drives the search is real and worth listening to. The answer usually isn’t to push harder. It’s to practice: small acts, repeated, that show you what enlarges you and what doesn’t. A purpose found that way may end up big, like Wilson’s. It will still have been walked into, not discovered.
Robert Moor, the author of On Trails, gave that idea a picture this week. In a conversation on Michael Easter’s Two Percent podcast, posted October 27, Moor describes trails as something no single person designs. Animals and people make small choices about where to step, and over time those choices wear a path. In his words, “we are all communally creating these paths for one another.” He says finishing a long thru-hike depends less on fitness than on being able to sit with your own thoughts and not quit. And he offers a line about aging that belongs here: a tree’s character comes from all the things it survives.
That’s a fair description of purpose in the second half of life. Not a destination you locate on a map. A path worn in by steps you keep taking, shaped by what you’ve come through, and made easier by the people walking it with you.
It’s also why Trailhead spends its time where it does. An expedition doesn’t hand anyone a purpose. What it can do is strip away borrowed expectations long enough to notice what makes you feel alive, and put you next to people asking the same question. Afterward, the community gathers when it can, and the journal keeps the conversation going between trips. None of it is a treasure hunt. It’s practice, and the trail gets clearer the more of us walk it.
How this was made: Trailhead keeps a running library of the thinkers who shape our work, and each week an AI reads across what they’ve published and drafts a synthesis like this one. The ideas belong to their authors and are credited and linked above; the pattern-finding is the machine’s, and the library is curated by Scott Levine.
Photo by Hanna Lazar on Unsplash.
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