I resigned on a Tuesday. I remember this specifically because Tuesdays were our weekly all-hands meeting, and I had spent the prior Thursday and Friday composing and deleting drafts of my resignation letter, and by Monday I had decided the cleanest thing was to simply say the words out loud before I could talk myself out of it again.
My manager's face went through several stages — surprise, concern, professional composure, concern again — and finally settled on something like understanding. He asked if I was okay. I said I wasn't sure. He said he'd been wondering when this would happen. That was not particularly comforting, but it was honest, and at that point I needed someone to be honest with me.
I was forty-one years old. I was a Vice President at a financial services company. I was making more money than I had ever imagined making. I was also having physical symptoms — chest tightness, hair loss, persistent headaches, three separate visits to urgent care in eight months — that my doctor kept attributing to stress, and that I kept attributing to bad luck. We were both right.
The Plan
I didn't have one, initially. I had savings, which provided about fourteen months of runway, and I had the vague intention to "figure things out" and "take some time." Two weeks after I quit, the vagueness was not resolving into clarity, and I was filling the structure vacuum with anxiety.
A friend mentioned the Appalachian Trail. I had heard of it — 2,190 miles from Georgia to Maine, hiked by thousands of "thru-hikers" each year — but had always filed it under "things extremely outdoorsy people do." I was not, by any reasonable definition, an extremely outdoorsy person. I had done some weekend hiking. I owned appropriate footwear. That was approximately the extent of my wilderness credentials.
I started reading. I read every thru-hiker memoir I could find. I joined online forums. I consulted gear lists. I booked a flight to Georgia for early April — the traditional start of thru-hike season — with the understanding that I would attempt the trail and see what happened. I gave myself permission to stop whenever I needed to. This permission turned out to be essential to getting started.
The First Month: Learning to Be Small
The first month broke me in ways I had not anticipated. The physical difficulty was manageable, though challenging. The emotional difficulty was not something I had prepared for.
I had structured my entire adult life around achievement: the next promotion, the next deliverable, the next performance review. On the Appalachian Trail, the only deliverable is making it to the next shelter before dark. This is simultaneously simpler and more difficult than a corporate job, because there is nowhere to hide and no one to delegate to and no leverage point except your own legs.
By week three, something began to loosen. I stopped thinking about my former job. This had felt impossible — I had been dreaming about it, waking up composing responses to emails that no longer existed. Then one morning I woke in a shelter in Tennessee and realized I had not thought about work in two days. I sat with that for a while. It felt like putting down something very heavy that I had been carrying for so long I'd forgotten it was there.
The Trail Community
People warned me about the loneliness of long-distance hiking. They did not adequately prepare me for the opposite: the intense, accelerated community that forms between thru-hikers who share the same miles, the same weather, the same aches, the same campfires.
I met people I would never have encountered in my previous life: a twenty-two-year-old who had deferred medical school, a sixty-eight-year-old retired firefighter hiking the trail for the third time, a software engineer on sabbatical, a woman who had just completed cancer treatment and wanted to celebrate by walking to Maine. We were extraordinarily different people united by exactly one thing, which turned out to be sufficient for deep friendship.
The Moment Everything Shifted
On a ridge in Virginia, on a clear October morning with the Blue Ridge spread below me in every direction, I sat on a rock and ate a handful of trail mix and thought: I know who I am again. Not who I was before the job, not who I was during it, but who I actually am when there's nothing performing me — no role, no title, no KPIs. Just a person with tired feet and a view that went on forever.
I didn't make it to Maine. I hiked 1,340 miles — just past the Pennsylvania-New Jersey border — before a stress fracture in my left foot required me to stop. I wept. Then I accepted it with a kind of equanimity I would not have been capable of eighteen months earlier, because the trail had been teaching me, relentlessly, that not all things are within your control, and some of the best things happen in the gap between what you planned and what you got.
After the Trail
I took a different job — smaller company, different sector, lower pay, fewer hours, infinitely more sustainable. I work four days a week. I hike every weekend. I go to sleep before ten most nights. My hair has grown back. The chest tightness is gone.
People ask if I regret quitting. I regret that it took me until forty-one to understand that a career is a thing you have, not a thing you are. I do not regret walking 1,340 miles to learn it.
— Jennifer Walsh, Asheville, NC
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