Alumni Voices: How One Citizen Schools Teacher’s Journey Inspires a New Generation
At Citizen Schools, we celebrate teachers as catalysts for curiosity, confidence, and change—champions who turn everyday moments into opportunities for students to discover who they are and who they can become.
This Teacher Appreciation Month, we’re honored to celebrate Sydney Chaffee, whose journey from Teaching Fellow to National Teacher of the Year shows how transformative educators—and the organizations that support them—can be.
Sydney’s first teaching experience with Citizen Schools’ 8th Grade Academy shaped her view of what education should be: rooted in relationships, fueled by creativity, and built on community.
“More than anything, being at Citizen Schools taught me about community, and about how to form relationships with kids and work with them in a way that is loving and caring and joyful.””
Sydney worked alongside students as a “warm demander”—a philosophy modeled by her Campus Director Tony Dugas and inspired by educator Lisa Delpit: challenge kids with high expectations while showing them they are loved. That balance between joy and rigor defined her experience.
“We somehow convinced kids to spend their April vacation doing MCAS prep... and then go outside and pie Tony in the face. That’s what Citizen Schools got right—serious academics and joyful community.”
The foundation she built at Citizen Schools helped pave the way for her career in education. In 2017, Sydney was named National Teacher of the Year—the first Boston Public Schools educator to receive this honor.
Today, Sydney continues to bring that spirit into her classroom. She urges new teachers to prioritize self-care and build strong peer communities—and calls on supporters to push for systemic change, especially gun violence prevention - an issue that impacts Syndeys’ students every day. Sydney also reminds us that community support is key for teachers:
“A note from a student or their family member means more than any piece of swag or free meal, to me. It's that moment of authentic connection and appreciation-- that moment of being seen and acknowledged.”
This month, your gift to Citizen Schools helps us support educators like Sydney—and inspire the next generation of students to dream big, give back, and transform the world around them. Let’s honor teachers not just with thanks, but with action.
“Working at Citizen Schools showed me how important community is to fostering an educational environment where kids can learn and grow and, if we’re lucky, change the world.”
