This qualitative study examines the journey of females to the role of superintendent. This study is based on interviews of six female superintendents from Indiana and Illinois in cities with a population of 15,000 people or more. Three of the superintendents had more than 25 years of experience in education, and three of the superintendents had 25 years or less experience in education. Data were collected by conducting interviews in person, taking field notes, recording the interviews, transcribing the interviews, and sorting the data. The theoretical framework used in this study is phenomenology, or looking for the essence and meaning of the lived experiences of the participants of this study. The participants of this study were asked to describe their journey to the superintendency and what advice they had for aspiring female superintendents. Further probing questions were asked to stimulate dialogue if further detail was needed. As a result of the study, several themes emerged. The overarching theme under which all others fell was that of relationships. Under the theme of relationships were subthemes of female leadership, leadership style, life experience, family/balance, hiring/school boards, and mentoring. In all areas discussed the focus was on how relationships impacted the subthemes. [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/en-US/products/dissertations/individuals.shtml.]