The role of public school superintendent is one of the most gendered executive positions in the United States, with men twenty times more likely than women to advance from teacher to superintendent. Although the majority of teachers and central office administrators in schools are women, the majority of superintendents are men. Women have made gains, yet under-representation continues to exist. As women break through the barriers, it is important to understand their experiences in administrative leadership as they navigate their careers. How do women in administration think and feel about working toward a male-dominated occupation? What barriers or opportunities have shaped their career choices? The review of the literature begins with a historical journey, studying the number of women superintendents from 1910 to 2017. The research dives deeper into external and internal barriers commonly found in the workplace. The literature on external barriers centers on structural barriers, discrimination, pay gaps and stereotypes. Internal barrier research examines voice and power, fear of backlash, ability to negotiate, and fear of success. A qualitative approach was used to study the experiences of six women working as public school administrators. The women all hold the proper superintendent certification, but they are not currently employed as a superintendent. Two interviews gathered the qualitative data, which was analyzed using feminist theory. Patriarchy, equality and discrimination made up the specific components of this theoretical framework. There are several conclusions derived from this study. First, women continue to face gendered stereotypes within the work environment. Second, mentors play a key role in propelling women toward administration early on in their careers. Career navigation and the concept of time were vital in these women's ability to reach the superintendent position during the course of their careers. Finally, self-confidence impacted their thoughts and feelings about various aspects of administration, including the desire to be a superintendent. This study provides insight to better prepare women administrators by providing an awareness of the barriers faced and suggestions on navigating these experiences. Rather than waiting for obstacles to occur, women can understand what might occur during the course of their careers in administration. Having prior knowledge allows women a better chance to navigate barriers rather than allowing those barriers to impact their careers and career choices. When these barriers are better understood, it may enable more women to mitigate the challenges of attaining a superintendent position. [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.]