Career trajectories within the academic enterprise elicit copious amounts of literature, much of which focuses on individuals who hail from faculty and rise through the academic ranks to college and university administration. However, scholarly discussions that conversely pay attention to administrators who transition to faculty roles are not as abundant even though they may possess unique skills, views, and perspectives that can positively contribute to the student experience. This reflection on practice describes challenges, opportunities, and insights for college and university administrators to make a successful transition to faculty through academic development.