In this essay, Jonathan D. Jansen and Samantha Kriger make visible the inner lives of the first Black principals in white-majority schools in South Africa. Through in-depth, on-site, narrative interviews with thirteen principals, and using the lens of interiority, they report on the anxieties, insecurity, and uncertainties experienced by these pioneers in the aftermath of apartheid, as well as their aspirations, commitments, and determination to transform predominately white institutions. Respondents spoke openly and candidly about their vulnerability as Black leaders in white schools, discussing the toll of school-based racism and resentment on their emotional lives, explaining the struggle between advancing and yet holding back change to avoid alienating white parents and teachers, and revealing how the racialized contexts in which they work awakened a reassessment of their own identities and of those they lead.