Life Is a Journey: An Interview with Roger Cheever '57

Kevin Bowen
Recently Nick Papps ’95 had a chance to sit down with DCD alumnus Roger Cheever ’57 to talk about Cheever’s time at DCD and the effect of that experience on his life over the years. The video, edited for length, was featured as part of this year’s annual meeting on October 25. Those fortunate enough to see the interview thought it well-worth sharing a few out-takes in print with the greater DCD community.

Reflecting on his journey, opened by pointing out that when his family moved from their farm where he’d been raised in Dennis up to Dedham, DCD was not on the first stop in his schooling.

“I was first enrolled in a school that was a great deal of fun but wasn’t very helpful. It was a place where I wasn’t achieving anything. It was a fill-in-the-blanks type of learning. I wasn’t challenged or encouraged to express myself, never given assurances I could take risks, or examine my feelings about things. You moved from A to B to C without deviating without reflecting on other possibilities.”

Cheever’s parents soon saw the problem and enrolled him at DCD, a decision that led to an experience he describes as “transformational.” 
“I know people often don’t believe me when I tell them I was shy as a kid. But I was. DCD changed that. It brought about a big change in my life. It allowed me to do things I never would have dared. While my other school taught me good penmanship and gave me a scripted curriculum, it never gave me the chance to take risks.”

Asked how this change came about, Cheever cited the rich opportunity for growth and exploration at DCD.

“For the first time I shared a classroom and classes with a single group of classmates. For the first time I was able to play organized sports and participate in extra-curricular activities. I began to realize academics were interesting and fun, to enjoy the camaraderie of team sports, the importance of learning to trust people.”

“One great memory I have is of my classmate Frank Owen, a gifted athlete who could throw a pass like no one could, he could put it right there. I think back on that feeling of trust I had playing football with him, knowing I could turn and trust the ball would be there right there falling into my arms.”

“It sounds simple, but it wasn’t. I had a long distance to travel. If DCD hadn’t taken the steps it took with me, I believe I would never have come out of my shell. Before I had felt quite alone, had never felt there were people at the school there cheering me on, but at DCD that changed.”

Cheever remembers one day when it all seemed to come together.“I was riding my bicycle up the hill on my way to school. It was a spring day, and I felt an incredible sense of liberation and freedom.”

But it was only after leaving DCD that he came to realize the value of that experience. “It was when I graduated that I realized how far I had come. I had been given the building blocks. I had developed confidence in myself. I had learned as a student to step forward and to learn things at deeper levels. I had the important experience of working collaboratively with others.”

“I was lucky,” said Cheever, noting things could have worked out differently, that he was most fortunate in finding his way to DCD, that the burden of failure lies not with the individual. “If in your life you didn’t have the possibility to feel you were empowered to take step forward in a meaningful way, the fault would not be yours, it would be the fault of your circumstances, a family situation, a school experience that lacks nurturing and support. If schools today don’t do that, provide support, encouragement, holding students accountable, they will not bring out the full potential of students.”

Cheever moved on to Milton Academy after DCD, then Harvard, and Cambridge University. Graduating, facing the prospect of conscription like many of his classmates, he volunteered, serving in the Navy for three years and four months, serving three tours in waters off Vietnam.

“That required taking on lots of responsibility,” he points out. “I worked with people I had never met before, people from all different backgrounds and walks of life, steering an aircraft carrier carrying four-thousand men on board.”

Cheever postponed going back to school after completing his service, instead taking the time to travel across the globe on his way home from Vietnam. Back home he returned to his studies at Harvard and Northeastern Business School and formed a company with a few friends. Here, too, he cites the value of his experience at DCD.

“I honestly believe life is a journey. Each step is important. You encounter things and you ask, does this look interesting? What is the potential good side? What is the potential bad side? It’s the way you grow. It took me two decades to decide who I was and what I wanted to do. It was never a straightforward line. Never a straight track to law or med school.”

“I was always appreciative of DCD for encouraging the over-the-edge steps I took. It’s sad if an individual never has a chance to really test their abilities. Taking steps, even if they’re wrong, prepares you to take on responsibilities later on. You don’t always win, you don’t always lose, usually it’s something in between. It’s like when building your blocks, you need to identify something that would be meaningful to you and find people to work with you who share the enthusiasm and make the work fun.”

“Often, I fear people try to go out too fast, jumping ahead. But life is not a sprint, it’s a marathon. Often circumstances make them think that the wisest course is just follow what the books says. It’s not enough to just say, this is what I’m going to do, to say, I’m going to be pre-med, you need to be willing and perceptive enough to know that you’re choosing because you want to make a change. You have to bring heart and soul along with right energy and attitude and all you learned in school to these choices.”

It is this same energy and spirit that Roger Cheever brings to his work every day as a Development Associate at Harvard, working at things, he suggests he would never have dreamed possible those first days at DCD. And though on his journey, Cheever has spent more years at Harvard and Milton than at DCD, DCD remains his favorite.

“I graduated in 1957 and the values I learned haven’t changed; they are about community, doing right thing with classmates and peers, working hard, playing hard, being a good citizen, having good listening skills and strengths.”

Cheever draws great satisfaction in seeing these same values passed on to the third generation of Cheevers at DCD.

“I’ve got two grandchildren now at DCD,” he says. 

“And I love the way the school makes grandparents feel important. I love returning to DCD with Chris and the grandchildren, to see them going through same things as I did, from the jungle gym to the plays. We all wear our DCD hats, me, Chris, and the grandchildren. Being there with them brings it back, reminds me that it was not so long ago I was that young boy riding that bicycle up the hill.”
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