Over the past 25 years, the number of women graduating from medical schools in the United States and Canada has increased dramatically to the point where roughly equal numbers of men and women are graduating each year. Despite this growth, women continue to face challenges in moving into academic leadership positions. In this Commentary, the authors share lessons learned from their own careers relevant to women’s careers in academic medicine, including aspects of leadership, recruitment, editorship, promotion, and work–life balance. They provide brief synopses of current literature on the personal and social forces that affect women’s participation in academic leadership roles. They are persuaded that a deeper understanding of these realities can help create an environment in academic medicine that is generally more supportive of women’s participation, and that specifically encourages women in medicine to take on academic leadership positions.