Despite the fact that women now comprise half of the medical student and resident populations, women remain underrepresented in prominent leadership positions in academia. Women are challenging themselves to live up to the expectations of their professional peers, society, and their patients in order to ‘have it all.’ These pressures are leading to professional and personal dissatisfaction. Is this a problem that will resolve itself as the younger generations of female physicians graduate into faculty positions, or does it require more attention from both male and female medical professionals?