This empirical qualitative study of 62 new principals was conducted over several years to determine what challenges they face, how the principalship compares with their expectations, and what their long-term career aspirations are. The findings indicate that the challenges experienced by new principals pertain to instructional leadership; managerial issues such as budgeting and human resources; and community issues involving climate, politics, and differing expectations from parents. New principals' job expectations depended on the experiences they had as assistant or vice principals. Finally, few new principals anticipated long-term careers as principals. Most new principals desired district-level positions within 10 years. Implications for preparation and professional development are provided. (Contains 5 figures and 1 table.)