What is transformative professional development for educators? Ideally, teachers and school leaders are given multiple opportunities to revisit schemas about themselves and their learning communities, with the intent to transform practice, the school environment, and even themselves. In practice, three cohorts of teachers and school leaders completed a yearlong program of professional development retreats, offered seasonally and funded entirely by two external partners, the Fetzer Institute of Kalamazoo, Michigan, and Texas Wesleyan University, Fort Worth, Texas. Teachers and school leaders were invited to spend both quality and quantity time in order to know each other better, to understand their school cultures better, and to listen more intently to their own inner voices. Other practices followed at the retreats included giving time for journaling and silence, raising questions and metaphors for engaged thinking, and allowing ample time to grapple with the nuances of paradox. This chapter describes a model program for transformative professional development, which may contribute to greater trust, beneficial self-reflection, and community transformation for educators. (Contains 4 tables.)