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.



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.