Men continue to dominate the superintendency in the United States, even though more than half of the specialized degrees needed to be a superintendent are earned by women (National Center for Education Statistics, 2019; Warner & Corley, 2017). Nationwide, 26.7% of the superintendents are women, while 27.75% of the superintendents in Illinois are women (Heffernan & Wasonga, 2017; Tienken, 2021). This study examined the lived experiences of five women superintendents from Illinois regarding their access to the superintendency and what they perceived to be significant factors along their trajectories. Data for this study was collected through one-on-one interviews using Seidman's (2006) three interview approach. Based on the data of this study, women's access to the superintendency is restricted. Barriers that seem to restrict women's access to leadership positions are a mobilization of bias and shaping of consciousness. Because of these barriers, women's paths to the superintendency are not linear, but resemble what Eagly and Carli (2007) have called a "labyrinth"; a career path filled with twists and turns as they find ways to overcome the barriers specific to their gender. Significant factors the study participants believed to be imperative to their career paths are navigating their career trajectories through the "labyrinth", managing role conflict and role commitment through balanced leadership, and their concepts of power and leadership. The findings from this study have implications for those responsible for the recruitment and selection of superintendents, mentors of women leaders, and aspiring women leaders. For those responsible for the recruitment and selection of superintendents, they should receive professional development to help uncover implicit biases they may have and examine hiring practices that are biased, restricting women from accessing leadership roles. Mentors may not be aware of the barriers women face along their trajectories and should receive training to help them understand the barriers that are unique to women's trajectories in order to better support aspiring women leaders. For aspiring women leaders, if they become knowledgeable of the barriers they may encounter along their trajectories, they can develop a plan to overcome potential barriers; thus, increasing their chances of accessing the superintendency. Due to the small number of participants for this study, further studies that examine the lived experiences of women superintendents should be considered. [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.]