In the Greek myth of Psyche and Eros, Psyche must fulfill four seemingly impossible tasks to achieve full consciousness before she can be reunited with her bridegroom, Eros. From early childhood, girls and women can encounter gender stereotyping, sexual harassment and assault, and other gender-related challenges. Although both men and women can face mistreatment in medical school, female students experience sexual harassment and sexual assault at higher rates than male students. In medical training and career advancement, women often face additional obstacles unrelated to the formal education of physicians, such as salary and promotional disparities, and lack of mentorship, sponsorship, or role models. The suicide rate for male physicians is nearly 1.5 times higher than the general population; for female physicians, it is more than twice as high. Parenthood can pose additional challenges for mothers and fathers early in their academic careers, and women are vastly underrepresented as they try to move past the "gatekeepers" into leadership roles. Using the framework of the Psyche and Eros myth to examine the trajectory of a female physician's career, this article provides insights into these challenges, as well as strategies to address some of these inequities, such as programs to support female promotion and leadership, expanded mentorship and mentor models, sponsorship opportunities, leadership accountability, implicit bias training, and others. The authors call for the participation of both men and women as essential in ventures to create a more humane environment for the training and practice of medicine.