We Were Never Meant to Climb Alone
“Are you having fun?”
I must have asked that question a hundred times over the course of one weekend.
Most people laughed.
A few looked at me as if I had completely lost my mind.
One man smiled and said, “It depends on how you define fun.”
After all, it’s an unusual question to ask someone whose legs are cramping, whose lungs are burning, and who has been climbing a mountain for over 20 hours.
But I wasn’t asking whether they were comfortable.
I was asking whether they understood what a privilege it was to be there. To be healthy enough to take on an extraordinary challenge. To be surrounded by a community that wanted nothing more than to see each other succeed.
Last weekend, I took on 29029 at Mont Tremblant, a challenge that required fifteen ascents, 29,029 vertical feet, and 29 hours on the mountain. I expected to come home with sore legs and a sense of accomplishment. Instead, I came home with something much more meaningful.
I came home believing, more deeply than ever, that we were never meant to climb life’s mountains alone.
After I finished, I rested for a few hours before taking the gondola back to the summit. I wanted to experience the final hours of the event and watch people complete their journey. It became one of the most emotionally powerful experiences of my life.
One by one, exhausted participants emerged over the crest of the mountain. Some raised their hands in triumph. Some embraced family members waiting at the top. Many simply broke down in tears, overwhelmed by everything they had endured to get there. Each time another climber reached the summit, complete strangers erupted into applause. Hugs were exchanged. Tears flowed freely. It was impossible not to get emotional watching person after person conquer something they had once doubted was possible.
Standing there, I realized I wasn’t watching people finish a mountain. I was watching people finish deeply personal journeys.
Throughout the weekend, I had the privilege of talking with people from all walks of life. Every conversation revealed another powerful story. One participant was determined to earn the coveted “Red Hat” after falling short in a previous attempt. Another was climbing in honor of someone they had lost, carrying photographs of loved ones on every ascent. Others had overcome serious illnesses or were still battling cancer. Many were sharing the experience with spouses, children, parents, or lifelong friends. One participant had quit, convinced the challenge was over, only to wake up in the middle of the night, decide they weren’t done, and climb back onto the mountain to finish what they had started.
One story, however, has stayed with me.
A woman I met had attempted 29029 before and returned determined to finish. She fought for every single climb. I found myself rooting for her as though we had known each other for years. As the deadline approached, everyone around her rallied with encouragement, hoping she would reach that fifteenth and final ascent. I offered to climb the final summit with her. However, time expired after her fourteenth climb.
I didn’t see this as a failure. I saw extraordinary courage, remarkable resilience, and someone willing to risk disappointment in pursuit of something meaningful. I also saw hundreds of people rooting for her as if she were family.
One of the principles I write about in The Life Is Too Short Guy is Can’t Make It Alone, and I’ve never believed it more strongly than I do today. Throughout those 29 hours, my phone buzzed constantly with messages from friends, family, clients, former colleagues, and many of you who receive this newsletter. Every text, every note of encouragement, and every reminder that people were following along gave me another lift when I needed it most. Thank you.
The mountain reminded me that our greatest achievements are rarely individual achievements. Behind every summit are people who encouraged us, believed in us, picked us up, or simply reminded us to keep taking the next step.
In a world where too many people feel disconnected, where conversations are replaced by texts and community is replaced by screens, perhaps the greatest challenge isn’t climbing another mountain.
Perhaps it’s finding our people. Building real relationships. Showing up for one another. Celebrating someone else’s summit with the same enthusiasm we celebrate our own.
Maybe that’s what I really meant every time I asked, “Are you having fun?”
Because real joy isn’t found in comfort.
It’s found in shared struggle, shared purpose, and shared victories.
Because here’s what I learned on that mountain.
Life is simply better when we climb it together.
Keep smiling,
Scott
The Life Is Too Short Guy