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Conquering The Mountain, One Step At A Time

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Stories, know-how, and guidance from the experts in educating boys.

Jacqueline Keller

Conquering The Mountain, One Step At A Time

Each year at the New England Boarding School Avon Old Farms, one rising junior is offered the opportunity to attend the outward bound program of his choice through the Woodwell Leadership Award. The Award was initiated by Al O’Connor ’75, in memory of fellow classmate and friend Richard H. “Woody” Woodwell ’75, who lost his life in the terrorist attack on September 11, 2001.

Interested students are required to write an essay discussing the topic of leadership, and one student who most demonstrates the potential for community service and leadership in his essay is chosen by a committee to receive this opportunity.

The Recipient

Gentry Shamburger Outward Bound

For this year’s recipient junior Gentry Shamburger of Atlanta, Georgia, the benefit of applying for the Woodwell Leadership Award was two-fold. First, it required a written essay application, and Gentry truly enjoys writing. Second, the ‘prize’ at stake was a 15-day wilderness excursion of the recipient’s choosing which would focus on building leadership skills. This experience was familiar to him, as his older brothers often enjoy hiking and camping but, as he described in his application essay, was something he often had to pass up due to his commitment to various hockey teams.

“I am always seeking leadership opportunities, and I really felt that receiving this award would help me better myself as a leader on campus,” shared Gentry. “This year, I will take on the role of captain on the varsity hockey team and I am a junior representative on the student council. I wanted to ensure that I am serving the Avon community as best as I can.”

The Mountain

When Gentry received word that he had in fact been chosen to take the journey of a lifetime, he employed the opinions of his family on where to go. They came up with three options and ultimately decided on going to the San Juan Mountains in Colorado to hike some of the tallest peaks in the continental United States.

The program’s website describes the experience as hard-won. “The few who are willing to work hard can access secret stashes of epic wilderness mountaineering the Colorado backcountry… The San Juans are very steep and receive significant amounts of snow that can persist year round. Once hikers reach tree line, you’ll focus on more technical climbing including ascending fixed lines, belaying and rappelling.”

The Journey

From day one, Gentry knew the hike would require every inch of mental toughness he had.

“I was already dealing with a fever and a head cold, but I had been feeling better the day it was time to head out, so I decided to go for it. On our drive to base camp, a member of our group got food poisoning and turned the three-hour trip into a seven-hour one. That meant by the time we got to camp to pack our things and bunk down for the night, we had lost four hours of daylight. And it was pouring rain.”

Down one man, the group members took on extra weight in their packs to ensure they had all the essentials with them for their journey. Gentry, who carried a 65-pound pack most days, also quickly learned about the effects of sleep deprivation, exposure, and a short supply of food.

“As someone who has played hockey since I could walk and practices for hours a day, I am used to eating all the food I want. Consuming an 800-calorie diet while enduring the most physically punishing task I’ve ever experienced gave me a whole new perspective on what some people live with.”

For the first five days, the group was led by two experienced counselors who taught them how to pack their backpacks, clean drinking water, set up and break camp, dry clothing, and many other skills needed on a long hike in the wilderness.

“From day six to day 10, the counselors fell to the back of the group and let us take the lead,” Gentry explained. “We navigated the trails – which were goat paths at best – set our pace, and worked as a team to find solutions to challenges that arose. But, the counselors were always present if we needed assistance or direction. The last third of the trip, they separated from the group completely and trailed us from a distance. At that point, we really were the leaders of our own journey.”

The Lessons Learned

It was in those final days that Gentry discovered some life-changing lessons.

With a gash on the sole of his foot that required stitches and a 14,000-foot peak in front of him, he learned what it means to push through the hardship.

“I’m very competitive at heart, but facing down a mountain when I could barely force myself to take another step was the first time in my life I didn’t know if I could finish what I started,” he shared. “I can’t tell you how many times I told myself to just put one foot in front of the other. I was suffering – physically, mentally, emotionally – but I still was trying to be a leader. I think that’s when I began to understand that leading when things are going well is easy – it’s when people are low on moral and facing a huge obstacle that true leaders emerge.”

For two days, Gentry went ‘solo’ – away from the group without his journal, without his watch, without anything to keep him company but his thoughts.

“I think that was the first time in my life I’ve ever been truly alone,” he explained. “Not home alone where I had a phone, television, internet to connect. Not alone where people were around but I didn’t know anyone. I had no possessions or connection to the rest of the world. I was deserted in the wilderness. And that’s when I began to have raw, uncensored thoughts that led me to a new set of priorities.”

He went on to explain that previously, hockey was his life’s focus. But, he began to see that one day, he wouldn’t be able to play anymore. He’d be too old. He’d have other responsibilities. In the end, it didn’t really matter. Neither did his last quiz score, or whether his team won or lost.

“The people in your life are what are important,” he began to realize. “I really looked up to my hockey teammates Danny Overcash ’18 and Aaron Pinton ’18 and all they accomplished at Avon. I don’t want to mimic their path through Avon, but I hope that one day I can have the same impact on my classmates as they had on me.”

The Takeaway

After 15 days of hiking, despite all of the hardships, Gentry had some advice for this year’s sophomores who will soon have the opportunity to write an essay for the Woodwell Leadership Award: just go for it.

“In retrospect, I would do it 10 times over. It’s something I will never regret.”


About the Author

JACQUELINE KELLER

Senior Marketing and Communications Project Manager

semborj@avonoldfarms.com