Peaks & Valleys

Trey Whitaker
2 min readNov 14, 2022

Written: 2016

I began working in the financial services industry in 1981 and eventually walked through the doors of MassMutual in 2008.

From a personal standpoint, it has been a tumultuous 8 years. During that time, I’ve had two bouts with cancer, both my parents passed away, I survived a Jeep rollover and my beloved golden retriever Ben died.

Despite all of that, I feel very fortunate.

One reason is that I really appreciate the work that I do. Being part of the MassMutual Way Center of Excellence for the past three years has been an educational experience. It has been a privilege to meet hundreds of people from across the enterprise and learn from their efforts and ideas. I have been continually amazed by their energetic and innovative spirit.

I have also benefited greatly from the support shown to me by my leaders, co-workers and people that I’ve met through ERGs, Toastmasters, TEDx Springfield and volunteer activities.

An example of this support was demonstrated during my mother’s final days this past November. I will never forget the consideration and compassion shown by my leaders and co-workers across MassMutual.

We will all face our share of life’s valleys but with support and a forward-thinking focus, we can have just as many peaks in our lives.

When I recovered from cancer in 2012, I was able to earn a black belt in jujitsu. My mother was there to witness my test. A peak after a valley.

My mother’s passing before this past Thanksgiving made the holidays feel a bit empty. During the holiday season, I registered for a CrossFit competition. I’ve always found that setting new goals keeps your eyes focused toward the future.

On January 23rd, during a shoreline blizzard, I ventured down to Danbury, CT and competed in the ‘Masters Throwdown’. Masters is a nice term for older, slightly gimpy athletes.

It wasn’t easy but, after 4 grueling events, I ended up placing third and earning my first podium spot. Another peak after a valley.

Inevitably, there will be another valley in store for me but I’m not waiting on that. I’m focused on building the next peak.

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Trey Whitaker

Former CrossFit gym owner, corporate manager, paratrooper, youth sports coach and jujitsu black belt. Now a trail steward at Haleakala National Park on Maui.