Sara Kaplan

Sara Kaplan is a three-time high school dropout who would have been happy to succeed the first time.  She rejects the notion that failure is chic and takes every opportunity to tell CEOs that they really don’t know what it’s like to be dyslexic—or learning disabled or female or gluten free.  For Sara, grit was a tenuous but unavoidable project, the only way forward but not a sure path to success.


In 2006, she earned her B.A. in Literature from Hampshire College and joined the tiny ranks of learning disabled students with college degrees.  With a 120-page thesis documenting Otherness in 19th British Gothic literature and a passion for alternative education, Sara moved to East Haddam, Connecticut to teach at Franklin Academy, a school for students with Asperger’s Syndrome and Nonverbal Learning Disabilities. Sara currently teaches at Eagle Hill School in Hardwick, Massachusetts, and serves as both an academic advisor and the President of the Alumni/ae Association.


Additionally, Sara is the editor of, a website devoted to reimagining education as the intersection of personal and community passions, as an endeavor that need not be about failure for an educational underclass. Instead, she sees failure in its best form as an unfortunate situation that can be handled with grace and determination.


Sara is currently pursuing her Master’s degree in a Creative and Critical Theory program at the University of Massachusetts, Boston and is passionate about working with students and teachers to develop creative and exploratory methods of promoting experiential education.  Her greatest achievements to date are having supported a student in realizing his vision of a colossal self-portrait in gumballs and keeping her dog Sputnik alive for ten years.  Her favorite conversation with her former students inevitably begins, “Hey, Ms. Kaplan, this is really hard—can you help me?”