Omitted in discussions of college athletes’ use of Name, Image, and Likeness (NIL) opportunities is a focus on equity, educational issues, and transition into post-college careers. We frequently hear National Collegiate Athletic Association (NCAA) declarations stating that nearly all college athletes ‘will go pro in something other than sports,’ but little is said about the challenges faced by Black athletes as they deal with coursework and the transition into post-college careers. In this paper, we summarize how the changing contexts of collegiate sports and race relations in higher education have intensified those challenges for Black athletes. We discuss how NIL opportunities can be used by Black athletes to expand identities, create and nurture relationships with mentors from Black-owned businesses, and develop programs in Black communities and organizations that promote social justice and racial equity. We assert that NIL can be combined with Happenstance Learning Theory (HLT) to develop skills for using unanticipated NIL-related opportunities in meeting challenges in courses and the transition into post-college lives. Lessons learned from support programs for Black athletes serve as a basis for recommending that universities fund the formation of a NIL Alliance of Black Athletes on campuses and provide career counselors to guide athletes as they meet people in connection with NIL deals that involve a combination of financial and personal development benefits relevant to education and future careers.