It is clear that there are differing cultures, contexts, and complexities among the various groups within higher education, creating a “great divide” on many campuses across the globe. This includes the divide between current faculty and faculty who have transitioned into administration. This panelist has conducted in-depth research on the lived experiences of women university presidents in developing the knowledge, skills, abilities, and competencies throughout their lives that are required for success leadership in higher education. Within this larger study, data were collected, using the phenomenological research approach, on the educational backgrounds, employment positions, career paths, and related struggles and challenges. This “great divide” emerged as a critical topic of interest, and the need for additional research became clear. This panelist will discuss her insights regarding the opportunities and challenges related to this topic, particularly for women, based upon the current literature, original scholarly research, and work in the field developing women in higher educational settings. She will frame her comments around Arthur, Claman, and DeFillippi’s (1995), “Intelligent Career” idea that was based on three dimensions: knowing why, knowing how, and knowing whom. This framework will serve as a tool to engage in a discussion of why some women chose to move into administrative roles and then how they navigate the transition and ongoing “divide.”