Leadership preparation programs find themselves in a state of flux, experiencing changing demands, and increasing scrutiny and accountability. New challenges and definitions of leadership preparation coupled with expanding demands for increased abilities of school leaders in ever larger numbers create the necessity to examine, question, revise, partner, and expand current program offerings. This paper discusses the changing context of a leadership preparation program striving toward a more ideal model while considering the realities of students' employment obligations, experience, and career aspirations. (Contains 1 table.)