This study, inspired by phenomenological and narrative methods, explored the question, "What does it mean to be a progressive educator in the 21st century?" Rather than a prescriptive piece about what progressive educators should or should not do, this study uses the experiences of three self-identified progressive educators to build a new understanding of this term. The participants, two heads of private school and one public school district superintendent, shared stories of their backgrounds, their current schools, and a time when they felt particularly successful in their work as progressive educators. Their stories reveal a commitment to risk taking, to achieving a balance between individual student and social needs, and to finding meaning in their connection with students and colleagues.