This piece was originally written in collaboration with Erin Gregory and first published on her Substack. Sharing here with her permission. I had so much fun working with Erin and I hope you enjoy this piece.
There’s a particular kind of woman who looks completely fine from the outside. She’s capable. She shows up. She carries responsibility because it’s just part of her role here on Earth. And underneath all of that, she is running on fumes she’s too proud to count.
Haley Peel was that woman. So was I. We have all been in that place.
Haley spent most of her professional life in pharmacy, first in hospitals, then in the corporate world. Precision. High pressure. Responsibility as the baseline expectation. She was good at it. She moved into leadership. She mentored people. She was, by every visible measure, succeeding.
She was also a sensitive woman in a field that didn’t have much room for that.
“I used to think something was wrong with me,” she told me. “I’d force myself to be social even when my battery was completely drained. That led to a lot of inner negative dialogue.”
She knew she needed to change something. But she didn’t find a therapist, she found a trail.
Hiking had been part of her life since childhood, family trips out West to the National Parks, but as a young pharmacist it became something else. A regulation tool. A place where the pressure could move through her instead of just sitting in her chest. She came back from the trails calmer, more grounded. Regular frustrations stopped landing as hard.
For a long time, that was enough.
When the Canyon Breaks You
Then she signed up for the Grand Canyon Rim to Rim to Rim.
I think about the version of ourselves that says yes to something enormous before we fully understand what we’re agreeing to. There’s something honest about that impulse. We know we need to be changed. We just don’t always know how much it’s going to cost.
42 miles. 20,000 feet of elevation change. Less than 24 hours.
Haley had no real frame of reference for what that meant. She chose the wrong footwear. She had no idea what she was doing. And 28 hours later, she emerged with battered feet and something worse: a broken spirit.
“I had always been the strong one. Especially in sports. I had never had to rely on others to get me out safely.”
The physical recovery was one thing. The mental spiral was something else entirely. She canceled her Kilimanjaro trip. She didn’t want to see pictures of the Grand Canyon. She questioned whether she ever wanted to attempt anything like it again. Her parents had been terrified, and she felt the weight of that.
This is the part of transformation stories that usually gets skipped. The part where it’s just wreckage, and you’re sitting in it, and you don’t know what comes next. That’s the messy middle. Most people live there longer than they ever planned to.
What I’ve come to believe, working with people in the middle of their own journey, is that the mess isn’t a detour. It’s the actual terrain. You don’t go around it. You go through it, and what you find on the other side isn’t a different version of yourself. It’s a more honest, authentic one.
Stories like Haley’s are exactly what the Self-Led Life was built for. If this one landed, start here — it’s the post that explains everything.
Two Years, One Step at a Time
Haley found her way through. It just took two years.
She didn’t return to the Grand Canyon right away. Instead she tried ice climbing, then an Ironman, then mountaineering. Each one a controlled risk. Each one building what she was actually after, even if she couldn’t name it then: self-trust.
“I fell in love with inner transformation through physical discomfort in breathtaking environments,” she said. “These trips were nervous system resets. They gave me something to look forward to, a challenge to work towards, community with like-minded people. Each one led me to feeling more grounded and more trusting of myself.”
When she finally went back to the Grand Canyon, she was different. Not fearless. Different.
She also stopped needing everyone around her to understand.
“Not everyone gets why I pursue challenging peaks or endurance hiking. They may worry about my safety. Some think it’s nuts.” She paused. “Over the years, I’ve learned to listen to my own intuition instead.”
That shift, from needing to be understood to trusting what she knows, is not a small thing. It cost her something to get there.
A Designed Life
There’s a word Haley uses that I keep coming back to: cocooning.
After a big trip or a stretch of heavy social obligation, she protects her recovery time. She doesn’t apologize for it anymore. She learned about highly sensitive people through the work of Dr. Elaine Aron, recognized herself in it, and stopped fighting her own wiring.
This is what it looks like to stop outsourcing your self-knowledge.
She frontloads her mornings now. Movement first, trail running or strength or a sauna. Then writing. Then the pharmacy job. Afternoons are for her goldendoodle, Fitz Roy, and evenings are quiet. Mobility. Meditation. Ukulele, sometimes. Dinners with friends when she has the bandwidth.
Weekends are for what she calls micro adventures. Planning the next big one.
It’s a designed life. Not perfect. Not finished. But deliberately hers.
I asked her what she wishes someone had told her when she could see what needed to change but couldn’t move yet.
She didn’t hesitate.
“You’re not behind. You’re exactly where you’re meant to be.”
And then: “Fall in love with the process. Design your life to embody the qualities you want to feel when you reach your summit. Find one small thing, even five minutes, that brings you joy each day.”
That’s not the advice of someone who skipped the hard part. That’s the advice of someone who went through it and came out knowing something real.
Haley is a pharmacist and a writer and an endurance hiker. She helps capable women prepare their bodies and nervous systems for iconic hikes. Her newsletter is called Wild Calm, which is the most accurate two-word description of who she is that I’ve encountered in a long time.
She’s working on a Rim to Rim Readiness guide ahead of the North Rim reopening this May, and she’s beginning to shape a longer story rooted in her adventure experiences.
She is, by her own admission, still in the middle of it.
Aren’t we all.
Erin Gregory is the founder of Erin Gregory Creative, a strategic communications and brand consultancy serving mission-driven organizations. She writes the Self-Led Life on Substack and hosts Notes from the Messy Middle, a podcast exploring meaningful work, pivots, and the messy reality of building something that lasts. She lives in Columbus, Ohio with her three daughters.
Stories like Haley’s are exactly what the Self-Led Life was built for. If this one landed, start here — it’s the post that explains everything.
Recommend Erin Gregory Creative to your readers
If you’re trying to build something sustainable instead of just successful, if you want work that serves your life instead of consuming it, if you’re tired of the hustle narrative and ready for something more interesting and authentic - this is for you.
 | A guest post by
|
It was wonderful collaborating on this story with you! My husband and I are excited to challenge ourselves with some new trails!