Published in the American Journal of Health-System Pharmacy, the following article discusses how women in work force sectors such as health care and academia, among others, are beset by an almost intransigent obstacle to their leadership aspirations. Women constitute slightly more than 50% of the U.S. population, represent approximately half of the labor force, serve as breadwinners in over 40% of homes, and control 70–80% of consumer purchasing and spending. Women earn approximately 60% of all bachelor’s and master’s degrees and approximately 50% of doctoral degrees, and they hold approximately 50% of managerial and professional-level jobs. Yet, despite their advanced degrees and ubiquitous work force presence in most professional sectors, including healthcare, business, and higher education, women are often absent from leadership roles such as chief executive officer (CEO), board member, president, and dean. The authors further concede how women are generally overrepresented in entry-level faculty positions and underrepresented in senior-level administrative positions, despite years of a strong pipeline and discuss the barriers in the path to women’s leadership