The purpose of this study was to investigate the lived experiences of women who successfully navigated the trajectory to the upper levels of administration in the public K-12 school districts, and how they leveraged opportunities and barriers to achieve their goals. Following a review of the research literature, a semi-structured interview protocol was developed to interview participants, regarding their lived experiences to attain the leadership positions. The themes that emerged from the interviews drew attention to the qualities of an effective leader, the importance of mentors, challenges women face in leadership roles, the transferability of the skills obtained from the classroom teaching experiences, and gender differences. The information in this study contributed to understanding the career path of those women who have successfully pursued and attained upper leadership positions. I hope this study will provide insight to inform more women about the internal and external barriers they are likely to encounter along their path to top administrative positions in education.