How an unconventional path opened new doors for Dr. Calvin Cupidore

Calvin Cupidore
Dr. Calvin Cupidore
Photo credit: Brad Ziegler

Dr. Calvin Cupidore may have worked his education and career paths in reverse, but he managed to script a story with a very good ending.

The New York City native had already built a strong résumé when he decided it was time to put the finishing touches on a journey he’d begun 36 years before. And he decided the place to do it was Walden.

“People usually build their education credentials first, then pursue their career,” Cupidore says. “I did it in reverse. I built the career, then I got the diplomas. Because of its reputation and history of educating working professionals, Walden was the perfect place for me to do it.”

Cupidore earned his Master of Business Administration (MBA) in 2011, followed shortly after by his Doctor of Education (EdD) in 2017. His degrees reflected a career that had already followed two unique vocations: finance and education.

Cupidore earned his bachelor’s degree in the 1970s and then built the foundation of his career through jobs in the banking and finance industries. In the 1980s, he was recruited into education, moving from New York to the Midwest, where he spent a dozen years in financial management executive positions with the Michigan Department of Education.

“I was thrown into situations where people might think I wasn’t qualified because I didn’t have the educational credentials,” he notes. “But I did the jobs, and I did them well.”

The apex of Cupidore’s career came in 2006 when he was hired as chief financial officer (CFO) for the School District of the City of Pontiac in Michigan, an urban school system with significant financial and student achievement challenges. After a year as CFO, he was appointed interim superintendent, bringing his experience in finance and education together.

This dual role, though, would only last 1 year, as the troubled school district continued a long leadership search that resulted in the hiring of six interim superintendents over 6 years. But the job provided a perfect place for Cupidore to evaluate his career options and pursue his long-deferred higher education goals.

“I realized that you don’t meet many school district superintendents who are ‘Mr. Calvin Cupidore.’” he says. “They all have their doctorates. I’d achieved a lot in my career, but I didn’t have the academic part buttoned down. After the interim superintendent assignment was complete, it was the perfect time to cap that part of my career.”

Cupidore credits Walden for taking in a student who hadn’t been in the classroom for more than three decades, noting that his acceptance and completion in the master’s and doctoral programs sent a clear message to him and others. “You can go back to school and continue to learn any time and at any age,” he says. “I’m a perfect example.”

Now he’s ready to start again. This time, he’ll start at the beginning. He’s in the process of forming his own consulting business, though he’s reluctant to reveal its focus. “I’m early in the process,” he says. “Essentially, I’m reinventing myself.”

Cupidore has come full circle, starting at the end and working his way back. Now, with his advanced degrees and an impressive résumé, he’s looking forward to the next step in his journey.

“I’m proud of what I’ve accomplished,” he says. “Now, thanks in part to Walden and my advanced degrees, I’m ready to start again. My story’s not complete yet. Not even close.”

— Kevin C. Thornton

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