This article describes and examines an Ohio State University graduate-level college teaching course that was created to address a range of intersecting questions about navigating higher education teaching and learning, research, and service. The course is required for all new graduate students in the Arts Administration, Education & Policy Department. Literature on mentoring and the voices of graduate students who took the course are synthesized to address the duality of being both a student and an instructor, academia's daily challenges, and how such reflections and experiences impact personal and professional career development. Using self-study as a methodology, the authors begin with contextual information on their involvement with the course and a genealogy of the course's development, followed by a narrative analysis to examine student feedback on the course goals. We conclude with suggestions on how other higher education visual arts departments or visual arts colleges might develop similar offerings.