The purpose of this qualitative research guided by resilience theory was to investigate the experiences of four Black women senior student affairs administrators at predominantly White institutions in order to understand the strategies for success that led to their advancement to senior level positions. Participants included four deans of students and/or vice presidents for student affairs (reporting directly to the president of the institution) at four-year small private predominantly White institutions (enrollment under 5,000). The participants' recounted experiences of tokenism, perceptions of the appearance, perceptions of communication styles, and inequitable compensation. They also reported support systems such as mentors, giving back, and spirituality that influence their thoughts, actions, reactions, decisions, and motivation to continue in the field, in their position, and ultimately in higher education. The implications of the study encourages institutions to provide funding, personnel resources, and training for all employees as well as encourages current Black women administrators to discuss their professional experiences to continue to inform scholarship and practice.