After serving 31 years as a school administrator, the last 16 as a superintendent, the author entered a career transformation by pursuing a tenure-track position in a research university. Following a calling to share acquired field experiences with the next cadre of school administrators, the writer outlines the process used to successfully compete for a university position. How-to preparation strategies, interview skills, and career decision-making processes are detailed. The article concludes with descriptions of differences encountered between being a prestigious superintendent and being a neophyte assistant professor. Demographics indicate that the number of retiring school executives may exceed the number of interested entering administrators. The latter need the experiential knowledge base of the former and the university seems ideally suited for such teacher/learner exchanges.