In this paper, two African American administrators share their experiences navigating and negotiating the White patriarchal dominance at two large, Southern, predominately White institutions (PWIs). Analyzing and trying to make sense of their shared experiences led us to discover that their challenges navigating the patriarchal society stemmed from failing to adhere to White cultural norms that permeate the fabric of these institutions. Our understanding has also led to the development of strategies for existing Black administrators and women of color who aspire to advance within and become successful in the Academy.