While most teachers in U.S. classrooms are women, most superintendents, the highest-ranking position in school districts, are men. Somewhere during educators' trajectory to superintendent positions, the representation of women diminishes. One might think that women, who make up most of the teachers, should be at least equally represented to men as superintendents. There are some considerations that have contributed to the underrepresentation of women. A review of literature included considerations such as family responsibilities, gender bias, discrimination, access, and mentoring to name a few reasons for the lack of female representation. This study identified and extrapolated meaning from the lived experiences of women in leadership. Study participants included sitting or retired superintendents, aspiring female leaders, and board of education members. While other studies have identified barriers for women in educational leadership, this study differed in that it sought information from three groups of active participants in the journey to the superintendency. The understanding of the underrepresentation of women in the superintendent role can be used for future studies and to inform important policy change, recruitment, and mentoring of aspiring female superintendents. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]