Despite literature emphasizing the importance of their presence on college campuses to minority student success, African American administrators are severely underrepresented in higher education. The purpose of this qualitative study was to explore the lived experiences of successful African American student affairs administrators at predominantly White institutions and factors that serve as enablers of and barriers to their career success. Beginning with a conceptual framework derived from the scholarly literature, 3 constructs were identified: (a) adjustment issues, (b) institutional factors, and (c) career dynamics. Following IRB approval, the authors identified a purposive sample of 14 successful African American student affairs administrators--4 women and 10 men--from predominantly White institutions. Length of experience in the field ranged from 5 to 27 years. Long semistructured interviews were conducted with the research participants. Data were coded to the conceptual framework with a phenomenological approach used to account for unanticipated and emerging issues. Findings for adjustment issues/enablers included the importance of mentoring relationships, healthy self-image and motivation, and social networks and family support. Adjustment issues/barriers included perceptions of prejudice and feelings of separateness or difference. Institutional factor/enablers are commitment to diversity (including recruitment strategies) and compensation/work conditions/resources. The institutional factor/barrier was discrimination. Career dynamics/enablers included professional preparation and undergraduate involvement in student affairs. The career dynamics/barrier was advancement opportunity. Implications for institutions wishing to increase African American administrator representation are presented.