This study evaluates the career paths of student affairs administrators (deans and vice presidents) in the California community college system. Top administrators are retiring at alarming rates and there are not enough potential leaders in the pipeline to fill these vacancies. Charting the career paths of individuals who have obtained top-level positions provides perspectives to help aspiring professionals plan their futures. In addition, institutions will need to rethink the current recruiting processes in order to identify potential candidates for these leadership roles. This body of research is important for both institutions to understand how they can fill future administrative openings when there is an apparent lack of potential candidates in the current pipeline, and for potential candidates to know what characteristics are most common for those who have attained administrative positions in the California community college system.