Teaching artists typically work as solo agents, without the comradery of a like-minded community. After a year of focus groups, teaching observations, and conversations with school and arts administrators, we identified a need for experienced teaching artists to have a chance to reflect upon, renew, and reconsider their teaching practices with others. We designed a 10-month professional development program delivered on-line (framed by in-person introductory and concluding sessions). For curriculum design, we drew upon several perspectives and practices including flow experience, responsive pedagogy, community, and self-study. Honoring the importance of seeing ourselves in others and the power of being seen, we describe specific experiences that contributed to the outcomes of the program. Questions around how, what, who, and where we teach are addressed vis-à-vis examples of student artistry. Implications for policy include attending to the symbiosis of theory and practice, the consideration of local needs, and the use of meaningful assessments.