This book presents an in-depth look, from entry to retirement, at all aspects of the administrative career. It uses the case-method teaching approach to discuss critical issues in education, specifically, cases of entry, equity, and endurance dilemmas. A total of 133 fictional cases are presented, based on interviews with school administrators and discussions with students. Particular attention is focused on the strengths of administrators willing to take risks, on women and minorities in administration, and on the assistant principalship. Chapter 1 introduces the study of professional socialization with a focus on the profession of school administration. Chapter 2 describes the steps of formal case analysis: (1) state the central problem; (2) identify important assumptions; (3) identify options; and (4) select the preferred option and defend the choice. Guidelines are presented for using the cases for the discussion of practical and theoretical issues in educational administration. Chapters 3 through 5 offer cases that deal with the issues of entry, equity, and endurance. The chapters examine the array of challenges that most administrators face, such as striking a balance between career and family, making transitions, planning for retirement, handling inequities and professional pressures, and cultivating mentors and sponsors. A matrix of cases and their central issues is provided. (Contains 132 references.) (LMI)