Magazine of CA

Character Construction

January 31, 2023

For the last 13 years, Upper School English teacher Kara Caccuitto has been shepherding CA students toward their best selves by way of literary exploration. Her approach— reflecting a carefully struck balance between challenge and support and heartfelt compassion coupled with unyielding high standards—is designed with a thoughtfully considered goal in mind: student empowerment.

Caccuitto has been a voracious reader and lover of literature since childhood. (She waxes nostalgic about birthday excursions to her local bookstore and the Scholastic book fairs of her youth. “That was party time for me!” she laughs.)

In her high school English class in New Jersey, a teenage Caccuitto found her enthusiasm for literary exploration—for teasing out the nuanced meanings of stories, exploring worlds different than her own, or feeling the emotional gut-punch of a powerful narrative—mirrored by teachers who found her perspective and voice valuable despite her young age.

It was an empowering feeling, life- altering, even: the recognition that her contributions and opinions could excite others, inspire deeper conversation, and yield better understanding.

Now—in spirited classroom discussions about the nature of humanity as evidenced in Camus’s The Stranger, or thoughtful considerations of the evolution of individual identity in Lahiri’s The Namesake, or perhaps while drawing parallels between McCarthyism and the Salem witch trials in Miller’s The Crucible—she ushers students toward similar self-actualizing discoveries. Along the way, she challenges them to engage thoughtfully, not only with the text at hand, but also with the world and each other.

“I want my students to step into who they are, into their power. I want them to ask questions and draw their own conclusions, to be thoughtful consumers of media, to be critical thinkers and empathetic participants in the world,” she explains. “I hold my students to a high standard because I respect them. I want them to know that they can meet it, to know that I believe—that I know—they can.”


At the heart of Caccuitto’s passion is a deep appreciation of literature’s power to challenge, inspire, and connect.

“Great literature can challenge us to think about things we may not otherwise ever experience. It can allow us to be in uncomfortable places and address challenging issues and themes with a little distance. It’s a powerful tool for self- reflection, one that fosters empathy and a deeper appreciation of the human condition, a better understanding of ourselves and each other,” she offers.

She’s aware that the introspective work she fosters in her classroom requires a vulnerability and authenticity that can be challenging, even uncomfortable, to some students. To bolster students against that discomfort, Caccuitto offers compassion and a diligent commitment to establishing an environment of trust and respect.

“Nothing in my own experience— no really worthwhile growth—has ever come without a little challenge, a little discomfort. I want students to learn how to lean into that, to embrace it. But to do so knowing that they have my full support and that I care about them as people. You can’t ask someone to be uncomfortable with you if they don’t trust you.”


As an educator that places a high value on the relationships she forms with students, it is perhaps no wonder that Caccuitto has emerged as a leading voice in CA’s advisory program. (In the Upper School, advisory is home base, a ready-made community where students can come together with a trusted adult to parse through any issues they may be having, in or out of the classroom.)

In addition to helming her own advisory group, Caccuitto also serves as lead advisor for the larger program, a responsibility that offers her the opportunity to get to know students with whom she might not otherwise interact. She values the mentorship opportunities it affords, whether coaching Student Council officers in leadership, helping an advisee process a thorny social interaction, or offering practical stress reduction tips to make life feel more manageable for an overwhelmed junior.

Her work provides a unique perspective into the overall character and pulse of a grade—the things that make them tick, or the unique worries and stresses that may be preoccupying the group consciousness. She shares these insights with grade-level leaders as part of an ongoing evaluation process designed to continually improve the overarching program and fine-tune it to meet the needs of an ever-evolving student body.

Those insights have been instrumental in shaping the advisory program into the CA signature that it is today. Caccuitto is particularly proud of two key changes made in recent years: the creation of a designated advisory time in the academic schedule and the continuity of advisory for a student’s entire Upper School experience. She credits them for building the requisite space to form meaningful bonds between not only a student and their advisor, but also between advisors and parents as well.

“These changes are important public declarations of the value CA puts on these relationships and the important work that is done during advisory,” offers Caccuitto. And that work is critical—creating a foundation of trust that is requisite for social-emotional learning and student mental health.

“It’s important for students to have someone to confide in, someone to process with, someone to whom they feel comfortable saying, ‘I’m having this issue.’ They are more likely to reach out to me now, having developed a relationship over the course of years.”


Given her evident passion and talent, in hindsight, teaching seems an obvious career choice for Caccuitto, but it wasn’t always so. Ultimately, it was a serendipitous assignment during graduate school at Boston College— teaching a first-year undergraduate writing class—that set her on the path to the high school classroom. (She would go on to earn a Master in English Literature and Letters and a Master in Secondary Education.

“That experience lit the fire,” says Caccuitto. “I realized that my future was about teaching instead of just being a literary scholar. As much as I loved literature or reading or stories, I realized I loved interacting with young people and teenagers the most.

“Planning lessons, diving into a new book, figuring out how to draw students in, determining what themes to explore, how to share the parts I love with them, and how to get them to share their thoughts with me? That’s what I love doing.”

At CA, Caccuitto puts that passion to good use. Most recently, she collaborated with her colleagues in the thoughtful restructuring of CA’s English elective program, a project driven by the realization that the traditional way junior and senior English classes had been structured was increasingly out of sync with CA’s mandate for student-centered learning that is personal, relevant, and flexible.

In place of more traditional year-long seminars in American literature or “Great Books,” students can opt instead for semester- long courses whose titles and themes—like “Evil and Villainy in Literature,” “Literature and Censorship,” or “Women in Literature,” also known as “Wonder Women,” where Kate Chopin is read alongside Alice Walker and Warsan Shire—read like those you might find in a college course catalog.

“We wanted to give students more choice in their learning, and faculty the flexibility to teach something about which they are passionate. It’s about giving students ownership over what they are learning and offering subjects and works that can invite them in and engage them in ways that maybe traditional classes might not,” offers Caccuitto.

And engaging a wider swath of students is key. In a STEM-obsessed world where the humanities are often under attack, Caccuitto is quick to point out the universal value of literature studies.

“Literary analysis—taking a piece of literature and breaking it apart and peeling back the layers to figure out what is really going on under the surface—is a transferrable skill that our students will use no matter what they go on to do.”

Recent CA alum Emily Wang, ’22, agrees. “Ms. Caccuitto taught me to be keen about asking ‘why?’ and ‘how?’ To not just accept things for what they seem, but to probe deeper and consider the broader social context. I’ve found myself using this mindset in my classes in college, in book discussions about the university’s role in facilitating democracy, during seminars on political theory, and while writing midterm papers on language and identity.”


Over the years, Caccuitto’s abiding love of stories has grown beyond those found between the covers of a book to extend more broadly to humanity: to the stories contained within each of us and to those that connect us.

“Talking to people about their lives, learning about their relationships, about how they see the world—that’s what makes life worthwhile to me,” she explains.

At CA, she has leveraged that curiosity in service of inclusivity as a leading voice for equity work. Caccuitto was instrumental in introducing some of the earlier iterations of CA’s equity programming—the National SEED Project (Seeking Educational Equity and Diversity). It was a humbling experience that has led to ongoing thoughtful consideration of her identity and how it operates in interactions with students and colleagues.

“I grew up in a fairly diverse area. I had a lot of friends who were different from me in a lot of ways. I think that naturally put me in a position of curiosity and maybe some discomfort,” reflects Caccuitto.

“But equity work has made me much more deliberate and thoughtful. It’s made me consider what my identity means and how I bring it to the table without even realizing it. To ask how I show up for students, or what I am not doing, or maybe more importantly, what I might be doing that could be inadvertently hurtful.”

More recently, Caccuitto co-founded and co-leads CA’s Anti-Racist White Teachers Affinity Group. The group creates a space for CA faculty to discuss whiteness, white supremacy, and their role as anti-racist allies/ disrupters in the larger community through deep dives into anti-racist resources and pedagogical practices.

For Caccuitto, it represents a lifelong learning commitment that honors her students, reflecting what is always top of her mind: how she can better show up, connect, and lead for their benefit.


Twenty-six years in the classroom, and Caccuitto still marvels at her good fortune.

“It’s amazing. After all these years, I still have moments where I think, ‘I am so lucky. What a privilege, what a delight, to be in this room with all these young adults working through this book.’ I mean, that’s my job!” she exclaims, a note of wonder in her voice. “That’s so cool.”

Her delight is evident—in the joy reflected in shared discoveries of a beloved story, in lightbulbs of recognition, and laughter that you can hear down the hall.

“That’s what comes to mind first,” shares alum Sidney Tai, ’22, fondly remembering her time in Caccuitto’s classroom. “A familiar image of Ms. Caccuitto—her laughing freely, with her head thrown back, as the sound of it echoes through the room. I saw it nearly every day of class. It was a constant reminder of how her energy creates a comfortable, nurturing environment for students to challenge themselves, struggle, and ultimately succeed.”

Written by Mandy Dailey, Director of Communications


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