Throughout history, women have faced numerous career barriers. Although significant progress has made it possible to break through the "glass ceiling," there remains a disproportionate percentage of women at the higher educational administrative positions, specifically the superintendent and high school principal roles. This study will look at one aspect of climbing a career ladder: self-imposed barriers of the journey to rise to an administrative position in public school systems. This study examines the commonalities and differences between and among gender specific Florida administrators. The study explores administrators at the educational levels: elementary, middle school, high school, and district office, more specifically at administrative positions of superintendents, assistant superintendents, principals, and assistant principals within the Florida public school system. Common themes were extracted from the participants' responses. These themes were used to develop recommendations that schools and universities may implement in order to continue fostering the upward progression of women within education. Acknowledging differences and recognizing barriers, while learning to balance personal and professional career roles will make that climb on the career ladder easier for leaders that wear heels. (Contains 4 tables.)