Heffernans up the Hill
Guiding my first mountain climb and witnessing what really matters
I went to All Day Running Company’s Hell on the Hill in May 2023 as a 27th birthday present to myself. It was expensive, but at the time, I had recently moved from Pennsylvania to Colorado, started coaching outside my 9-5, and was seeking connection.
Even as a finance guy who values the power of compounding, I’ve come to realize the best investments are those we make in ourselves. As such, I eagerly flew from Denver to Atlanta without knowing a soul, hoping to meet like-minded individuals.
We all go through seasons in our lives when our social circle shrinks. We lose touch with friends from high school, then college, then our first job post-grad, and so on. I used to fight against this uncomfortable reality; however, in recent years, while still unsettling, I’ve learned to embrace it.
Not everyone is meant to be in our lives forever. Most come and go, but hopefully they’re there long enough to teach us lessons we needed to learn. Or to understand what we actually want in a friend or significant other. Knowing what we don’t want is just as important.
As we age, our social circles change. Instead of resisting and insecurely holding on to doomed relationships, understand you’re growing and recognize that the other person is changing too.
For 48 hours, on a farm in the middle of Georgia, I felt alive and present. I shared a tent with strangers, ate with different people every meal, and while I introduced myself to many new faces, I aimed to have quality and meaningful conversations.
Not having cell service was a blessing in disguise, providing an opportunity to connect in real life and removing the temptation to stay within my comfort zone. I left with four photos in my camera roll, but forty contacts.
One of those contacts was Dee Heffernan, a fellow Pennsylvania native. Dee was a final finisher of Hell on the Hill, one of world’s hilliest half marathons, which required us runners to complete 60 laps on a 0.2 mile course. As the time cutoff closed in, other athletes rallied around Dee, cheering her name and pushing her in the final minutes to get the job done.
While working incredibly hard, physically pushing more than she ever had in her life, she kept a smile on her face—something I’ve always remembered.
For months, a group of us from the event met weekly for virtual calls, wanting to hold onto the magic we all felt that weekend. Not long after, Dee and I began working together 1-1 as she wanted to break into triathlon and improve her endurance.
Later in 2023, she ran the furthest she ever had at the inaugural Runningman Festival. In 2024, she completed her first 70.3 in Western Massachusetts. Now, in 2025, after winning her age group and landing on the podium for the first time, she’s setting her sights on her first Ironman!
Her family owns a Chick-fil-A franchise and is opening a second location next month in Pennsylvania. Last week, the Heffernans flew out to Denver for a conference for entrepreneurs and small business owners.
In March, when making their Colorado plans and knowing they’d have an open weekend in the Rockies, Pikes Peak came to mind. They attempted to climb the famous 14,115 ft peak 18 years ago but failed. They wanted redemption and asked if I could help.
Looking to expand my coaching offerings, I jumped on the opportunity. I organized a call on planning, logistics, gear, training, and protocols to set them up for success.
While I’ve climbed 20 different 14,000 ft peaks in Colorado alone, in all seasons, I had never hit Pikes. My girlfriend
and I scouted the northwest slopes the week before to familiarize myself with the route and ensure it was safe. While we summited, it was a long, stormy day for us, two experienced hikers and athletes who live at altitude.I communicated our findings and expectations to the Heffernans, reminding them that this is a serious alpine challenge not to be taken lightly. We targeted May 22 for our adventure, but the weather had other plans. As a result, we pushed to the following day, giving us the most time to hike in clear conditions, increasing our summit chances.
Because Pikes is 150 miles from Boulder and we were getting an alpine start, I stayed at my friends’ apartment in Colorado Springs, still 45 minutes from Crags Trailhead. Thanks for the hospitality,
and Kaitlin.At 3 AM, my alarm rang, I made a Nespresso, then hit the road for Divide, CO to meet the Heffernans—Dee, her sister Danielle, her mom Debbie, and father Dave. Because the road was closed a mile from Crags, we agreed to start at 4:30 AM to give ourselves seven and a half hours to climb before the 12 PM turnaround I set for safety.
In the predawn hours, we gazed at the stars, miles away from any light pollution. Dee led a beautiful prayer before we turned on our headlamps and began our journey. As we cherished the sacred twilight, I shared tips on movement efficiency, fueling and hydrating, and energy management.
Shortly after we turned for Devil’s Playground, we encountered a stream crossing. After taking one look at it, Mrs. Heffernan quickly said, “I can’t do do that”, similar to my mom on Mt. Sanitas the previous week. We encouraged her, I pointed out which rocks to place her feet on, and she made it to the other side. She smiled, her confidence boosted, and it set the tone for the rest of the day. “I can do this.”
I made Mrs. Heffernan lead to ensure we were going at a sustainable pace for all of us. If she wasn’t out front, she was right behind Dee or Danielle to follow their footsteps. We navigated steady switchbacks and rocky terrain before we stopped to put on our microspikes and lightened Mrs. Heffernan’s load near 11,800’. We continued east up the snow-covered slope for another four hundred vertical feet, until Mrs. Heffernan’s 72-year-old legs no longer had the strength to continue.
Here, at 12,150’ and 10:00AM, Mrs. Heffernan felt defeated and guilty, wanting her family to continue in her absence as she accepted she was the limiting factor. Also here, a beautiful show of affection was conveyed. Dee, Danielle and Dave rallied behind Debbie, similar to how All Day Running Company rallied behind Dee at Hell on the Hill. They reinforced they wanted to share the experience, regardless of the outcome.
On and off mountains, it’s important to stay together. It’s also important that we set internal and external goals—subjective and objective metrics to define our “success.” If we judge ourselves, our loved ones, or an outing based on a time, reading on an altimeter, or reaching a peak, we’re setting ourselves up for failure.
As I shared with the Heffernans at our highpoint just above treeline, the summit is never guaranteed. Reaching the top is optional. Getting down safely as a group is not. As I shared with my mom just days earlier, it’s about doing this, whatever this is or ends up being, together. Even if the girls decided to push on, they didn’t want to summit without their mom—something with which I deeply resonated and was heartwarming to witness.
While we stopped to enjoy our peanut butter sandwiches for lunch, we were passed by two sets of men, both asking for beta. It was obvious one of the groups was dangerously unprepared for the task ahead—in shorts, tee shirts, road-running shoes, no packs, no poles, no water, no calories. I advised them to turn around, but they couldn’t be convinced and continued up the slushy trail. Shaking my head, I was reminded how people die in the mountains and why Search and Rescue exists.
On our descent, we were passed by the other set of men. While well-trained and prepared, they reached 12,800’, found themselves stuck in knee-deep snow, and bailed. Although not easy, it was clear we had made the right decision to turn around. As we made our way down, I learned about operating a restaurant from Dave, the pains of aging from Debbie, and shared jokes, goals, and conspiracy theories with Dee and Danielle.
With a mile to go, after she took a spill on scree, Mrs. Heffernan gave me her pack and we walked back to the car together. As we cruised downhill on dirt, she expressed her gratitude for the role I’ve played in Dee’s life—providing a sense of direction and helping her achieve more than she thought possible. Sometimes we need someone to believe in us before we can believe in ourselves.
As Sir Edmund Hillary once said, “It is not the mountain we conquer, but ourselves.” It can be on Mount Everest or Pikes Peak, but the mountains have a way of humbling us, reminding us mere mortals that we’ve never in control.
As we said our goodbyes, tears streamed from my face—honored they trusted me to guide and invited me on their intimate excursion they’ll remember forever. I was grateful to witness their beautiful family dynamic, which in turn, made me even more appreciative of the time I recently shared with my aging parents.
Coaching and guiding is not an easy business, but it’s certainly rewarding. Despite a 3 AM wakeup, ten and a half hours in the wilderness, and two more in the car back to Boulder, I felt invigorated and in flow. I called Candice, excited to share the details of my awesome day—better than any day I had in my six years in financial services.
wherever I live you're always welcome and kaitlin was stoked about the flowers and I'm stoked you enjoyed your stay. Longs and many more 14ers in our future. Theres a good chance I'll have a week in mid july to knock of some 14ers and I'm thinking maroon bells potentially but would love to have you join me for some random Wednesday adventures
What a cool experience for all! ❤️