Lessons from Hell on the Hill

“Tomorrow, an hour into the race, the hill is going silent. We will continue to run, but observe a 20-minute silence. During that period, I invite you to think about why you are running this race and who you are running for besides yourself. Tonight, I encourage you to consider those questions. Because tomorrow, when it gets hard, and it hurts, and you want to quit, you can call upon that source of inspiration to push further and finish what you started.” 

I was all in on the post-dinner prompt from All Day Running Co-Founder and host Jesse Itzler on the eve of Hell on The Hill, the world’s hilliest half-marathon. My brother and I had arrived in South Berwick, Maine, midweek to conquer the hill. This was a bucket list item for him. It was a grueling test of will and perseverance for me. As I retired for the night, I committed to myself: “I am going to finish what I started.” 

Who Are You Running for?

Before the starting gun sounded on race day, Jesse invited a few willing participants to share their reasons for running and who they would remember during the silent 20 minutes. Soon after the shares started, there wasn’t a dry eye on the hill. I was moved, inspired, emotional, overwhelmed and grateful to be a part of this immersive experience unfolding. 

I leaned over to my brother Chad and casually asked, “who are you running for, man?” 

He didn’t hesitate. “I am running for you, bro. That’s why we are here. I am running for brotherhood.” I nodded in the affirmative. I understood. So did he. We were going to finish what we started. Together. 

We both hit our limit on the hill that day. In truth, we both under-trained. But through it, we found a way to finish what we started. Together. 

Pushing Past Your Perceived Limits

Jesse shared during his opening remarks that he had three hopes for everyone participating in this event. He hoped that each person would:

  1. Meet someone new.
  2. Learn something new.
  3. Try something new. 

I’ve realized that just about everyone has something to teach us — and I learned a whole lot from this community on that hill. It is extraordinary to be surrounded by a group of people, each of whom is pushing beyond what they think their limits are in the service of something larger than themselves. 

Hell on the Hill served as a potent reminder that there are times in life when you think you’ve hit your limit. What you discover on the other side is that you have more to give than you think you did, that you can keep going, and that part of the reason you keep going is for those around you.

Some of my most profound learning occurs when I am willing to look deep inside myself. I am better for it, and I am reminded (again) to keep showing up, trying my best and chipping away. I couldn’t have done it alone — I needed my brother. I also know he needed me. That shared understanding means everything. 

I encourage you to think about why you are running and who you are running for. When it gets hard, borrow that inspiration and the belief and support of someone else who cares enough to run right along with you. 

Read More personal growth

And join our email community to receive bi-weekly insights with actionable tips and videos, new research, and inspiration and ideas for cultivating growth in business and life.