Dale Caldwell '78 on Finding and Amplifying Your Voice

Dr. Dale Caldwell '78, the Hopkins School Distinguished Alumnus for 2024, stood at the podium for just a few seconds before breaking from tradition. 

After being introduced at an all-school assembly this past winter, Caldwell chose to walk across the gym floor, delivering his presentation just a few feet from the front row. The significance of this confident gesture might not have been immediately apparent to the students in the bleachers, but for the small group of Caldwell’s former classmates who returned to Hopkins to see their friend's presentation, this moment marked a profound transformation. When Caldwell began his journey at Hopkins as an eighth grader, such confidence would have been unfathomable.

“They would have never imagined the quiet Dale they knew would one day become a confident public speaker,” Caldwell reflected.

Now a well-respected author, speaker, and business leader with decades of achievements, Caldwell returned to the Hill to inspire students. He encouraged them to push through discomfort, become positive influences on others, live purposeful lives, and create meaningful change in the world. His core message was to find one’s voice and use it for good.

These themes were not just abstract ideas; they were reflections of Caldwell’s lived experiences. Back in the mid-70s, when he walked the halls of Hopkins, Caldwell struggled to find his own voice. As a self-described introvert, he found it difficult to adapt to his new environment, rarely speaking in class and mostly keeping to himself. 

“I was one of only a few African American students in my class, and I just didn’t have the confidence to speak,” Caldwell recalled.

Two key experiences at Hopkins—one academic and one athletic—helped Caldwell break out of his shell. The first came through the school’s demanding writing curriculum. Writing gave him the opportunity to communicate his thoughts and express himself in ways he couldn’t in social or academic settings. Encouraged by his teachers to continue honing his skills, Caldwell gradually built up his confidence.

“Hopkins was truly transformational,” Caldwell said.

Outside the classroom, tennis provided Caldwell with a sense of belonging. Exceptionally talented on the court, he was named captain of the Hopkins boys’ tennis team in high school.

“Being pushed by Hopkins, both in tennis and academics, was really what I needed," Caldwell said.

Before long, he began to thrive in the "supportive, loving, and encouraging environment” that Hopkins offered. He started to socialize on campus and increasingly felt like a leader. Caldwell fondly remembers faculty members like Bill Ewen, his seventh and eighth-grade math teacher and legendary tennis instructor, who retired after a 44-year coaching career, as key figures in his development.

"The words of affirmation that I got at Hopkins made me say, 'If they think I'm that good, then I better be that good,’” Caldwell recalled.

Caldwell credits Hopkins with teaching him the importance of feeling “comfortable being uncomfortable,” a mindset that he carried with him after graduation, approaching future endeavors with curiosity and excitement in the face of uncertainty.

After Hopkins, Caldwell graduated from Princeton University with a BA in economics; from the Wharton School of the University of Pennsylvania with an MBA in finance; and received his Doctorate in Education Administration from Seton Hall University. At Princeton, Caldwell continued to build on his leadership skills, working his way up in the school’s dining hall from mopping floors to becoming the CEO.

"Hopkins opened up that door of leadership," Caldwell said. 

Much of the academic skills and lessons Caldwell took away from Hopkins have defined his life and career. Those writing skills he built on the Hill clearly paid off as he has now published eight books. In addition to touring the country as a motivational speaker, Caldwell is currently the President of Centenary University in Hackettstown, New Jersey, and the Pastor of Covenant United Methodist Church in Plainfield, New Jersey. He is also the Founder and Board President of the Dale Caldwell Foundation, whose mission is to reduce poverty through education and entrepreneurship. He has more than 33 years of experience as K-12 public school board president and is also the founder of management consulting firm, Strategic Influence LLC and Founding Executive Director of the nonprofit, Newark Alliance. 

Caldwell also enjoyed a remarkable tennis career after his Hopkins playing days. He was nationally ranked by both the United States Tennis Association (USTA) and the American Tennis Association (ATA). His influence on the sport continues today. He is the author of Tennis in New York: The History of the Most Influential Sport in the Most Influential City in the World, and has served on the Board of Directors of the USTA. He was the first Black president of the USTA Eastern Section and founded the Black Tennis Hall of Fame to permanently recognize individuals overlooked by history because of their race. In 2010, he received the Tennis Educational Merit Award from the International Tennis Hall of Fame. In 2021, he was inducted into the Eastern Tennis Hall of Fame.

At the assembly, Caldwell discussed how successful individuals, teams, and organizations are able to break through the boundaries that are limiting in order to accomplish goals and eventually give back to their communities. Drawing from his own experiences, Caldwell emphasized that true happiness comes from how one deals with life's difficulties. These were core themes in one of his books, Intelligent Influence: The 4 Steps of Highly Successful Leaders and Organizations. Caldwell also enthusiastically discussed his current work at Centenary University, where he oversees a Master's program in Happiness Studies.

"The secret to happiness is anti-fragility. It's how you deal with the downsides in life," he explained.

After his speech, Caldwell visited classrooms and hosted two Q&A sessions.. He said he enjoyed engaging with current students, answering their questions and sharing life lessons. Caldwell expressed admiration for the current students at Hopkins, noting their intelligence, capability, and kindness. He contrasted this with his observations from serving on various public school boards, highlighting the unique advantages of the Hopkins environment. 

"Places like Hopkins develop the brain. The faculty here really help people develop their thought process," he stated.

Caldwell also spoke to students about the responsibility that comes with attending Hopkins.

"Going to Hopkins is a privilege and should never be taken for granted," he said, urging students to remember the importance of helping others. 

Returning to Hopkins as a distinguished alumnus was a deeply meaningful experience for Caldwell. The full-circle moment he experienced back on campus was not lost on him.

"It was a big accomplishment for me to be one of the faces in the crowd and then to be the distinguished alumnus today," he remarked.

The Distinguished Alumni Award, established in 1991, honors alums who have demonstrated extraordinary accomplishment in their chosen fields, and service to their communities. Hopkins continues to be an institution committed to fostering those qualities that come from a liberal arts education: learning how to learn, how to think clearly, how to express ideas effectively and how to work independently. Today, as throughout the school’s history, students learn that knowledge should be tempered by ethical judgment, consideration for others and aesthetic sensibility; that far greater than academic achievement and preparation for college are a sense of curiosity and a love of learning; that intelligence and training carry with them the obligation to serve others. The Distinguished Alumni/ae Award salutes individuals who exemplify these qualities.