Women in the field of education are strongly represented in the classroom but are much less likely to become school district superintendents. For decades, women have continued to attain the top district leadership role at a rate of slightly less than one to four, compared to their male counterparts. The purpose of this study was to understand how women who have been superintendents for at least three years experienced mentoring and role preparation as they aspired to the position. Participants were female superintendents in Washington State who served in the role for different tenure lengths, in a variety of school district sizes, and across different geographical areas. Social role theory and social network theory were the theoretical foundations for this investigation, providing a framework for understanding the unique experiences and career pathways of female superintendents. A transcendental phenomenological research methodology was selected to amplify and highlight the voices of the women interviewed for this investigation. Prominent themes included the glass ceiling, family influence, career pathways, mentoring and sponsorship, representation, volition, and personality characteristics. Finding life balance to promote sustainability in the role was a common concern, as was focus on practices that support the wellbeing of female leaders. The underrepresentation of women in the superintendency is a serious concern that is not changing quickly enough and perpetuates gender inequality in a system responsible for the development of young people. Implications for practice and future research are explored. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]