The number of women in academic medicine has steadily increased, although gender parity still does not exist and women leave academics at somewhat higher rates than men. The authors investigated the reasons why women leave careers in academic medicine. Semistructured, one-on-one interviews were conducted in 2007-2008 with 20 women physicians who had left a single academic institution to explore their reasons for opting out of academic careers. Data analysis was iterative, and an editing analysis style was used to derive themes. A lack of role models for combining career and family responsibilities, frustrations with research (funding difficulties, poor mentorship, competition), work-life balance, and the institutional environment (described as noncollaborative and biased in favor of male faculty) emerged as key factors associated with a decision to leave academic medicine for respondents. Faced with these challenges, respondents reevaluated their priorities and concluded that a discrepancy existed between their own and institutional priorities. Many respondents expressed divergent views with the institutional norms on how to measure success and, as a consequence, felt that they were undervalued at work. Participants report a disconnection between their own priorities and those of the dominant culture in academic medicine. Efforts to retain women faculty in academic medicine may include exploring the aspects of an academic career that they value most and providing support and recognition accordingly.