In this Invited Commentary, the author applies a historical lens to explore a fundamental paradox in U.S. medical education: the fact that long after women gained parity with men in matriculation to medical school, women remain highly underrepresented in leadership positions in academic medicine. The reasons for this are many and complex, but at the core are the subtle but hurtful indignities ("microinequities") experienced by women physicians and an academic culture that expects single-minded dedication to work, regardless of the costs to faculty members' personal lives. Achieving parity for women in academic leadership will require changing the culture of medical schools and teaching hospitals to correct these 2 fundamental obstacles. In recent years, many medical schools and teaching hospitals have made efforts to improve opportunities and satisfaction for women trainees and physicians, enacting reforms to improve work-life balance for all faculty. It is plausible to imagine a future in which flexible time frames to achieve tenure and promotion are universally available to both women and men, with high scholarly standards firmly maintained. If this occurs, it will represent a profound legacy for women in academic medicine, for their generations of professional sacrifice and advocacy for a more equitable culture will have changed its culture.