Although voluntary departures are frequent among new professional student affairs staff members at small colleges and universities, there is little systematic study of the processes involved in departing a job at one campus to accept a student affairs position at another. Potentially awkward dynamics surrounding staff departures can complicate professional relationships and reputations, and unanticipated staff departures often result in increased work demands for staff members who remain. This study explored professional and developmental dimensions of voluntary departures of student affairs staff members at small colleges and universities using aspects of the transitions model (Schlossberg, Waters, & Goodman, 1995) and the synergistic supervision model (Winston & Creamer, 1997) as principal theoretical frameworks. Findings indicate that supervisors and graduate faculty members can assist new professionals and junior colleagues to regard voluntary departures as predictable occurrences related to career advancement and/or personal fulfillment that, in cooperation with dedicated supervisors, can be professionally managed. Ideally, supervisors and supervisees should have early discussions about departure expectations and processes. (Contains 1 table.)