The journey of professional musicians traditionally focuses on the mastery of artistic and technical skills in preparation for performance demands. However, research suggests that over 90% percent of artists will teach at some point in their career. For many, the role of professional musician expands beyond performer and into educator or teaching artist. As many musicians transition into roles as teaching artists, they face the unique challenge of adapting their performance expertise to educational environments without the benefit of formal pedagogical education. This leads to many teaching artists feeling unprepared to teach and artificial barriers being drawn between certified educators and performers. This conflict highlights a critical gap in the professional development of professional musicians and the field’s ability to not only educate professional musicians as performers but as educators.This study examined curricular designs and professional development for teaching artistry. Drawing on the work of Kolb (2015) and Brookfield (2017) as theoretical frameworks, the study examined how professional development experiences can be created for professional musicians and undergraduate performance majors to better prepare them for work as teaching artists. Over the course of three years, the author taught and refined an undergraduate teaching artist course offered to performance majors. The students taught in a large, diverse metropolitan high school and individually and collectively reflected each time after their teaching. The study found that by fostering reflective practice, the teaching artists could better navigate the complexities of classroom dynamics, align their artistry with educational goals, and effectively collaborate with certified educators. Suggestions for future curriculum and professional development opportunities for teaching artists are offered. Situating teaching artistry within the broader context of the professional musician’s educational journey underscores the importance of integrating skill development, not only in performance but also in reflective teaching practices, to prepare musicians for the dual demands of artistry and education.