Thinking Differently

Math prodigy Cyndi Moore brings a new perspective on problem solving to Eagle Hill.

Eagle Hill School recently welcomed Cyndi Moore, an Eagle Hill parent alum, mathematician, former finance executive, and special education advocate, to speak with Dr. Tony McCaffrey’s Unsolved Problems in Computer Science class. Drawing on her personal and professional journey, Moore shared how embracing a different way of thinking can open new approaches to solving complex challenges.

Moore began by reflecting on her own path, one that did not initially resemble a traditional mathematician’s story. As a high-achieving learner, she often could “see” the answer to a problem before understanding the steps needed to reach it, requiring her to work backward to identify the underlying formulas and processes. “I knew what the answers were, but I didn’t know how to get them,” she said. Math became a source of anxiety rather than confidence, even causing her to become physically ill at times. Over time, she came to understand that math was less about memorizing procedures and more about learning how to communicate the way she naturally thinks.

Moore came to recognize that this way of thinking was not a limitation, but a different kind of strength.

Moore came to recognize that this way of thinking was not a limitation, but a different kind of strength. While traditional classrooms emphasized memorization and procedure, she was instinctively working in images and systems—rearranging, reshaping, and exploring problems dynamically in her mind. After high school, she carried this intuitive approach into a twenty-year career in finance at Fidelity, where she eventually led an international team in work that required constant problem-solving and systems thinking. She later transitioned into special education advocacy, supporting students with disabilities.

She described moments of realization about “how things are done” and “why things are hard,” noting that these experiences strengthened her appreciation for Eagle Hill’s approach to teaching and learning.

As an Eagle Hill parent alum, Moore reflected on how her time in the EHS community has deepened her understanding of how students learn. She described moments of realization about “how things are done” and “why things are hard,” noting that these experiences strengthened her appreciation for Eagle Hill’s approach to teaching and learning. She added that she wishes she had attended a school like Eagle Hill earlier in her life, where different ways of thinking are more fully understood and supported.

Moore shared how her mathematical thinking has reemerged in unexpected ways in her life. A physicist challenged her to solve a problem that had previously been unsolved. Leaning into her intuitive, visual approach, she arrived at a solution. “That’s unbelievable,” he told her, and Moore responded, “This can’t be an unsolved math problem. This is really easy.” The experience, she explained, helped her recognize the full extent of her ability to solve complex problems that others could not, rooted in the way she thinks rather than something she learned traditionally.

Moore also invited students into some of the broader ethical questions surrounding mathematical discovery and responsibility. She asked students to consider what it means to hold solutions that could reshape industries or be applied in both constructive and harmful ways—from encryption and robotics systems to broader questions about how knowledge is shared and used. Drawing on examples from her own thinking, she emphasized that mathematical insight often carries decisions about whether and how that knowledge should be shared. She encouraged students to think about those choices through three competing values—capitalism, altruism, and protectionism—posing the question: “Are you responsible for the good or harm that other people do?”

Her message to Eagle Hill students was clear: the goal is not to think like everyone else, but to learn how to express the way you already think.

Her message to Eagle Hill students was clear: the goal is not to think like everyone else, but to learn how to express the way you already think. “I don’t need to learn how to think like everybody else. I just need to learn the language of how to communicate it,” she said. She challenged students to reconsider what feels difficult, adding, “Whatever is hard could actually just be hard because you do it differently. And the way you do it differently is actually what the world needs.”

Her visit left students with a lasting reminder that thinking differently is not something to overcome, but something to recognize, develop, and value—an idea that resonates deeply at Eagle Hill School, where learning differently is at the heart of the student experience.

Listen to Cyndi’s Moore message to Eagle Hill Students >>