The Problem The current pipeline supplying qualified and competent leaders to the upper ranks of higher education appears to prelimit the number of Black males who reach executive status. Even though many universities and colleges remain resolute in increasing diversity, social, and structural barriers block access and restrict executive development. This study focuses on the leadership and career advancement of Black male executive leaders in predominantly White institutions (PWI’s) of higher education. The Solution This qualitative, phenomenological examination of the lived experiences of 10 Black male, executive leaders in predominantly White institutions of higher education describes what it is like for them to persist in their leadership roles despite negative experiences that are related to their social identity. The findings reveal how their existence in racialized environments has impacted their leadership approach and the trajectory of their careers. The Stakeholders The stakeholders are Black academics seeking or holding executive leadership roles in higher education; HRD scholars and practitioners.