Change at Cary Academy doesn’t always arrive with fanfare. At a school where innovation is a core value, change is expected. It often begins quietly: with a good question, a thoughtful conversation, and an open mind. And that’s just how Dr. Donna Eason is approaching her new role as Head of Upper School—with curiosity, creativity, and a bold eye toward the future.
A longtime CA educator with nearly two decades of experience across roles, Eason is uniquely positioned to ask questions: What’s working? What could be better? And how do we evolve, together, to prepare our students for the world ahead? With the school’s new strategic plan launching this fall, she’s focused on aligning everyday practices with CA’s long-term aspirations—ensuring the systems that shape school life reflect our values and support our boldest goals.
Whether in a college classroom, a counselor’s office, or the halls of Cary Academy, Eason has built a career helping others feel seen and supported. Now, she draws on those same instincts—listening deeply, leading with empathy, and fostering collaborative growth. For Eason, it all starts with relationships—and a deep belief in the people she serves, students and faculty alike.
Rooted in Relationships
Born in Chapel Hill and raised in Greensboro, North Carolina, Eason grew up in a household where learning wasn’t just valued—but celebrated. A childhood immersed in books—especially speculative science fiction and horror (“I was probably reading ones too mature for me at the time,” she laughs)—sparked a love of storytelling and curiosity about the world and its possibilities. “Books opened up the world,” she says. “They helped me find my place in it.”
Her mother, a lawyer, hosted annual teacher brunches, welcoming dozens of educators who had taught her six children. “It showed us what it meant to really invest in education, to build relationships,” she reflects. “Our teachers cared deeply, and that care made all the difference.”
Though she initially considered following her parents into law or medicine, her path shifted. After attending Howard University, earning a BA and MA in English from North Carolina A&T—and later adding a second master’s in counseling and an EdE in Curriculum Instruction for good measure—she found herself, often the youngest in the room, at the front of a college classroom. At first it was daunting. But in the act of designing lessons and sharing them with students, something clicked. “I realized, this isn’t a stopgap—this is who I am.”
That realization eventually led her back to North Carolina—and to CA, where she joined the faculty in 2005. Since then, she has worn many hats: English teacher, grade-level leader, Dean of Students, and Assistant Head of Upper School. With each role, her perspective deepened. “With every new position,” she says, “I’ve asked: how can I make things clearer, more collaborative, more compassionate?”
Now, as Head of Upper School, she’s clear-eyed about the work ahead—and energized by it. “This job has asked me to dig deeper into who I am. It’s pushed me to grow, to get comfortable with discomfort, and to lead in my own voice.”
A Vision for the Future
Eason’s vision? A thriving Upper School that’s innovative, connected, and future-focused. One where interdisciplinary learning—like the worldbuilding class she designed years ago—is more of the norm, rather than the exception. “That class changed everything for me,” she says. “Students were tasked with creating entire worlds from scratch—narratives, histories, ecosystems. It blurred the line, not only between disciplines, but also between teacher and student. We built things together. We learned together. That’s the kind of community I want to keep building.”
Her leadership is already taking shape, rooted in listening, reflection, and a commitment to sustainable growth. Her immediate priorities are practical: “I’m taking a close look at our policies and processes,” she explains. “Are they working as intended? Are they meeting our needs and goals?”
She is eager to expand faculty leadership and growth opportunities.
“There’s so much expertise and creativity in our community,” she notes. “I want to explore ways to tap into that—to create space for shared growth and innovation.”
And she’s focused on bridging disciplines and divisions, breaking down silos and fostering continuity between the Upper and Middle School to create a more cohesive student experience.
Eason acknowledges the creative tension at the heart of CA’s ethos: the balance between flexibility and structure, innovation, and consistency. “We’re trying to walk a line between being responsive and interest-driven, while offering a dependable, exceptional academic experience,” she explains. “X Days, field trips, competitions, and our many experiential and expeditionary learning opportunities—they are integral to the CA experience. They may complicate the calendar, but the payoff is profound.”
When it comes to building community, Eason brings both experience and humility. “I don’t want to assume I know what people want,” she says. “So the first step is to ask.” From one-on-one check-ins with faculty to biweekly student lunches, she’s tuning in to the moments that shape school culture.
She believes a stronger Upper School community comes from shared ownership of our mission, where students and faculty alike feel empowered to lead, connect, and innovate as co-creators of a meaningful learning experience.
A Vision Grounded in Care
Behind Eason’s leadership is a determination to ensure every student feels seen, supported, and challenged. “My hope is that parents trust that I will take care of their child, not just protect them, but push them to lean into challenges.”
That trust is especially important when it comes to student wellness, a long-standing priority at CA and a cornerstone of the forthcoming strategic plan. “Being a teenager can be hard, especially in today’s world. Thankfully, we have an incredible team in Student Support Services doing vital, compassionate work every day,” she affirms. “I see my role as a partner—elevating what’s already strong and exploring new ways to help students lead healthy, balanced lives.”
She’s careful not to conflate wellness with happiness. “Resilience matters,” she says. “We don’t want to shield students from struggle. We want to help them grow through it so that they are prepared for the real world.”
Ask Eason what student success looks like, and she won’t start with test scores or college lists. For her, it’s about engagement, agency, and transformation. “Success is when a student lights up about something they learned in class. When they produce something—an idea, a project, a shift in thinking—that goes beyond the grade.”
It’s also about voice. “When students can speak confidently to adults, when they can advocate for themselves—that’s success. And not just for the extroverts. Everyone deserves that skill.”
An Experience Like No Other
Eason deeply values what makes CA’s Upper School extraordinary: the freedom to explore, the abundance of opportunity, and the people who make it happen. “The opportunities here are unparalleled. Our students get to design experiences based on what excites them,” she says. “From X Days and global trips to electives and independent studies—it’s amazing. I’ve heard so many parents say, ‘I wish I had this when I was in school.’ And I say it, too.”
But what really sets CA apart, in her eyes, is the care. “We have a whole network of adults who are watching out for students—and each other. From our faculty to our school front office staff, our incredible counselors and learning specialists, to the team at the Center for Community Engagement, it’s not just one person. It’s a community. That makes a big difference. It’s something special.”
That holistic view of education—where well-being, authenticity, and curiosity are central alongside academics—shapes how she advises students and parents alike. For students: find balance. “Your life isn’t something that starts after graduation. It’s happening now,” she says. “Grades matter, sure. But so do your friendships, your passions, and your peace of mind.”
And for parents: listen. “Ask questions that extend beyond academic outcomes. Be present. But know that sometimes your child doesn’t need a fix—they just need a safe place to land.”
A Call for Collaboration
Looking ahead, Eason envisions even more collaboration—across disciplines, among faculty, and between divisions.
“In life, you don’t operate in one lane. So why should learning?” she asks. “When we bring different lenses together—STEM with humanities, science with art, math with social justice—the outcomes are richer. The work becomes real. And the learning sticks.” That’s the kind of school she wants to lead. A school where silos give way to synergy. Where students learn not just for a test, but for the world. Where community isn’t assumed, it’s intentionally built.
Leading With Heart
Eason doesn’t shy away from the challenges ahead. From evolving college pressures to the rise of AI to the erosion of student resilience, she knows the path ahead is complex. But she faces it with openness and resolve.
“I’ve learned that leading means being honest, being compassionate, and growing thicker skin,” she says with a smile. “And knowing when to give people what they need—not to make life easier, but to help them shine.”
Ask what defines her most as an educator, and she doesn’t hesitate. “If something doesn’t exist and I think it should—I start it,” she says. “And I don’t need to be the one to finish it. But I’ll get it going.”
That mindset—equal parts initiative and care—drives her approach. She’s not just launching new ideas; she’s building the trust and structures that help them take root. Whether it’s a redesigned student schedule or a quiet, steady moment of support, she finds meaning in the work that connects intention to impact.
“The kids,” she says, “are always the bright spot. But helping a teacher feel supported or giving a parent peace of mind—those moments matter. That’s when I know I’m doing the work I’m meant to do, that I am leading with purpose.”
