Trail Sisters Half Marathon & 10k

September 14th • Buena Vista, CO

Regrets, I’ve Had a Few

In 2016, Allison traded Prada heels, a Manhattan high-rise, and a decade-long pursuit of law firm partnership for running shoes, a used car, and an adventure in the American West. During her travels, she fell in love with Colorado’s San Juan Mountains, where she now writes, runs and explores. Follow her on Instagram (@liveuntethered) or at

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Outside, darkness blanketed my car.

Inside, my legs stretched over a crumb-dusted eggplant mattress while my back rested on a bag stuffed with outerwear. Relics of the prior days littered the bins that lined the car’s interior—empty water bottles, half-eaten boxes of Triscuits, and crinkled maps. As I surveyed my home’s chaos, I thought about the road I’d traveled to arrive at this particular trailhead on the eve of my thirty-fifth birthday.

My dad loves to say, “I have no regrets.” When pushed, he confesses two regrets, but no more. He’ll claim that every mistake, every wrong turn led him to wherever he is on the day he’s extolling this wisdom. And wherever that is, it is exactly where he wants to be.

Over the prior months, I had thought about his claim often.

If I could have repeated the prior seventeen years, the list of what I would have done different was so long it would fill the dark void that blanketed my car. Sure, I was glad to be at the trailhead at that particular moment, but to get there, I had stood hundreds of places I wished I had not. How could I not regret the detours?

Sunrise on the approach. PC Kim Bessler

For years, I’d traveled a road I’d long expected to follow to the end. It was a road lined with what I thought I should want—a swanky Manhattan apartment, designer heels, and law firm partnership. Plus, that road seemed safe.

But in traveling that path, I was hiding. I muffled the creative, the imaginative, and the simple. Hid the girl who spent her days writing, directing and starring in plays. Hid the teenager who found freedom in the sound of her feet on dirt trails. And hid the woman who couldn’t understand why, after years of following all the rules, she was so unhappy. 

Six months ago, I had walked away from that life. I downsized to a car, and I drove west with no plan other than to chase what excited me in America’s wilds.

During those six months, I had thought about my younger self often. I wished I could slap her and say, “Living a life afraid of dark will extinguish light!” Or shake her and scream, “Walking a path not your own will one day break your heart!”

Of course I couldn’t. But that didn’t stop me from thinking about it.

As I tallied all the advice I’d bestow on her, two stark beams slithered along the gravel drive. I peered through the piles on the bins as if I were peeking through an overgrown jungle. Then, I halted the hypothetical banter to meet tomorrow’s climbing partner—Kim.  

I’d been introduced to Kim through a woman I’d met on my recent stay in Wyoming. Kim lived in Colorado and climbed mountains every chance she got. My arrival to the state coincided with Kim’s planned climb of Ellingwood Point and Blanca Peak, two 14,000-foot mountains that loom over rolling sand dunes in the Sangre De Cristo Range. Kim invited me to join.

Kim traverses the ridge to Blanca Peak

I swung open my car door and plunked my feet on the gravel as her red two-door sedan halted next to me. With the car still running, a woman dressed in tattered cut-off jeans—the kind that would prompt my grandma to ask, “Where are the rest of those?”—and a cropped tank top that revealed no expense had been spared at the tattoo parlor tumbled out of the sedan.

She landed with hurricane force winds.

“Oh my God. My car barely made it up that road! It was slow going. I picked up some 20-something German hitchhiker. Dropped him at the other trailhead. He wanted to join us. But I said, sorry dude, these are some serious mountains we’re gonna climb.” She crossed her arms over her chest. “I don’t climb with just anyone. I know you’re legit cause I saw you just ran forty miles through the Tetons, but I don’t think that guy had ever climbed a mountain before.”

She reached in her car, yanked out the keys and then adjusted the Colorado flag buff she wore as a headband over silky dark brown hair. “I’m so excited for this! It’s gonna be gnaaar. The couloir we have to get up is super loose. It’s pretty much the couloir of doom.”

Allison laughs at Kim’s jokes. PC Kim Bessler

Her upper body swayed as she spoke, and her legs moved side to side. She talked as if someone had cranked her speech up to double the speed. (I later learned that was exactly how she listened to podcasts.)

“Oh my God, I’m so psyched you can do this. So you’re living on the road?” She flung open her arms and we hugged. “I did that about a year ago. I can’t wait to hear about it.”

She jolted to the rear of her car and popped the trunk. “Okay, you have an ace bandage and helmet right?”


“Have you looked at the route? We can go over it. But first, I gotta pee.” She whipped around and jogged to the pit toilet. Halfway across the parking lot she spun back. “Oh yeah, weather looks decent for tomorrow. I’m thinking we leave by 4 a.m. sharp. I can be up and on the trail fast. I don’t drink coffee, I just eat what I can and go. I’m thinking a 3:30 wake up.”

Based on our first two minutes together, I understood why she didn’t drink coffee.

I combed my hand through my curls, as if to check on whether Hurricane Kim had tussled my locks. No obvious aftermath, other than a beaming grin and a forgotten list of regrets.


The last time I was awake during the 3 a.m. hour on my birthday, I was ending the night, not beginning the day. And the only stars I saw dance across the sky were the artificial twinkles of skyscrapers.

Kim traverses the ridge from Ellingwood Point.

As we sauntered to the trail in the pre-dawn hours, it seemed that Hurricane Kim had been downgraded to a tropical storm. Under the dim glow of a cloud-covered moon and the streams of our headlamps, Kim told me of her mountain rebirth.

Like me, Kim grew up in the rolling hills of upstate New York and fled the idyllic suburban life just after high school. Unlike me, Kim did not chase the shoulds. She chased rebellion. For a decade, she chain-smoked, downed pills, slipped into alcohol-induced hazes, and dated vile men. Then, sitting in the passenger seat next to one such man, she had a moment of clarity and knew she had to change her life. She looked at the man and said, “I’m moving to Denver.” The words tumbled from her mouth, much like she had tumbled from her car on arrival at the trailhead. He told her he had no plans to leave the ski town where they shared a home. To which she said, “I know.”

Two months later, she packed up her things and moved to Denver. She enrolled in community college leaving the man and pills she had come to depend on behind. Nine months later, she flushed the cigarettes and booze too. Twelve months later, she stood at the rim of the Grand Canyon. Short on time, she decided to travel the rugged terrain on foot donning a pair of tennis shoes. Three years later, she had climbed all but a handful of Colorado’s 14,000-foot peaks, plus countless other mountains, competed in multiple ultra trail runs, and transferred to Colorado’s School of Mines, where she was earning an engineering degree.   

By the time we reached the summit of Ellingwood Point, the titled towers of rubble we traveled, the rays of sun seeping through wind-whisked clouds and the woman at my side filled me with a trust in the world, and a trust in my path.

We didn’t linger long. We wanted to traverse to Blanca Peak before the wind-whisked clouds bloomed upward and threatened storms.

An hour later, we stood on Blanca enshrined in mist—a timely reminder that there is a beauty in what cannot be seen. After a few photos on the summit, we retraced our steps over the ridges and down the “couloir of doom.”

This particular couloir looked as if an assortment of boulders had been dropped from a helicopter and each boulder selected a random spot on the slope to halt. Adding to the challenge, these large stones rested on loose granular rock and dirt so one step could send you skidding down several feet.

Allison and Kim on Ellingwood Point.

As we made our way to the grassy meadow at the couloir’s base, Kim sank onto the blanket of lush green next to a meandering stream. “I need a snack.”

“Me too.” I plunked at her side, and slid my helmet off.  “It’s my birthday today.” I scooped a handful of potato chips into my mouth. 

“What!! Why didn’t you tell me?” She smacked the side of my arm.    

“Guess I just wanted to be in the mountains.” I gazed back at the couloir, which led to the summits we stood atop moments ago.

“I get it. But, Happy Birthday!”

Around this time, Hurricane Kim was upgraded to a Category 2 Storm and as we traveled back to the trailhead, questions about my life gusted in and near toppled me.

I steadied my footing as I tossed my life story along the trail.

I rehashed the heartbreak of a failed collegiate running career. Told her of my struggle with bulimia, the struggle I blamed for the broken dream, the struggle I had since buried deep in the archives of my memory.

I told her how my fear of another heartbreak pushed me onto a path that was not my own. I recounted the decade-long pursuit of law firm partnership that had left me unsure of who I was. Told her how I worried that after years cloaked in the familiar, I’d lack the buoyancy to risk, to chance failure.

Allison gazes at the Sangres. PC Kim Bessler

I revealed my dreams to write. But confessed not knowing what to write or where to start.

And I admitted that I feared I would never find what I was looking for.

As I scattered my story along the trail, I looked down at pieces.

I don’t know if it was the way Kim listened with an understanding born out of years hiding from her own potential.  Or the enduring euphoria of standing atop two summits. Or the wisdom of age. But for the first time in my life, I weaved a tale of love, forgiveness, and pride when I told of my flawed journey.

When we reached the trailhead, we tucked ourselves in the shade of my car where I unwrapped birthday gifts my family had sent. When I tore into an air freshener, we tumbled into laughter. We both knew, from first-hand experience, that there was no hope of keeping a lived-in car smelling good.

As I listened to her laugh and looked at her smile, I had no doubt that I was exactly where I wanted to be on the first day of my thirty-fifth year.




About the Author

In 2016, Allison traded Prada heels, a Manhattan high-rise, and a decade-long pursuit of law firm partnership for running shoes, a used car, and an adventure in the American West. During her travels, she fell in love with Colorado’s San Juan Mountains, where she now writes, runs and explores. Follow her on Instagram (@liveuntethered) or at

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4 Responses

  1. Great job! Sounds like a lovely day of release in the mountains! Reminds me of my fav quote- There is only one of you for all time, fearlessly be yourself.

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Sept. 14th 2024

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Half-Marathon & 10k

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