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While increasing attention is being paid (in critical circles) to healing-centered education for students, little research has examined educators’ experiences of well-being, particularly in wellness-centered schools. This paper explores stories (through testimonio-oriented conversations) of three former educators’ experiences in an urban, public, alternative high school focused on generating regulation and wellness as the foundation for learning. Educators’ wellness and healing were supported by processes of unlearning and relearning, a school community practicing concepts of power-with, communal learning, and mutuality, and a radical acceptance of the authentic and full human selves of each person who entered the school.