For students in undergraduate and graduate programs in health policy and management, particularly those who wish to be trained as public-health-oriented generalist health administrators, as well as those charged with the responsibility of being their teachers, it is important to consider the trajectory, tensions, and rewards of a career in health policy and management. This article begins by examining what we have learned from earlier research and writing on health policy and management careers and then moves on to analyzing the career history and professional development of 40 graduates of the generalist health policy and management program at the University of Massachusetts School of Public Health. Finally, the article reaches some conclusions about career paths for generalist health administrators trained in at least one school of public health.