This paper is a collation of the vicarious experiences of four Black women, all senior-level educational leaders in the United States of America. Considering the predominance of White males in educational leadership, our paper furthers the conversation around increasing race-gender diversification in this realm. We employed the tenets of hermeneutic phenomenology, focusing on the intersections of race and gender, in the effort to challenge extant epistemologies manifested within this context. Using in-depth, timed, semi-structured interviews, participants reflected on their journeys, experiences, and perceptions as non-archetypal leaders in education. In highlighting contributors’ perspectives, our objective was to bring the matter of race-gender underrepresentation in educational leadership to the forefront. Study participants revealed the importance of visibility, education, collaboration, exposure, mentorship, pursuit, authenticity, and living one’s truth in the move towards diversifying the educational leadership sphere. Participants’ recollections revealed the need for more research specific to the journeys of non-typical educational leaders in the context of the United States.