Institutions of higher education have a glass ceiling: women are underrepresented in the college presidency with 30% of college presidents as women, 83% white and 17% women of color. By nature, the culture of higher education has been traditionally male centered, with female professors and researchers struggling to advance in their careers. Contributing factors that may lead to the lack of women college presidents may be linked to long-held systemic views of women and gender biases that create barriers in career advancement. The objective of this qualitative study is to explore the ways in which women, from their perceptions, navigated opportunities and managed obstacles as they advanced into the college presidency. For the women who did advance to the highest level of leadership in IHE---the college presidency---what did they experience as they advanced in their career, and what enabled them to navigate the system and transcend the barriers? Qualitative data were analyzed using an inductive thematic analysis process through convergent and divergent coding tools. Four key findings emerged from this study: (1) Women were intelligent, talented, successful, savvy, and brave; (2) Servant Leadership; (3) Gender Fluid Characteristics; and (4) Support and Well-Being for current college presidents. This study offers an increased awareness of barriers that are limiting women from progressing to the college presidency in institutions of higher education. It also offers an increased awareness of the phenomenology of women college presidents and the ways that they managed obstacles and took advantage of opportunities as they advanced in their careers. [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.]