Although graduate preparation programs are a key entry point for the higher education and student affairs (HESA) profession, many programs fail Black women practitioners who later serve in predominantly white work environments (PWWEs). While a dominant narrative suggests Black women perform well as learners in higher education, there is limited research on their HESA advancement, status, and ambitions. The author used this study to illuminate the advice and strategies that Black women who have been pushed out or opted out of the HESA profession or workplaces seek to offer practitioners choosing to enter and remain. The author positions their advice as vital because Black women who have departed the field have unique perspectives on recruitment and retention that those remaining should consider. To complete this study, the author used Robinson and Williams' expansion of Fries-Britt and Kelly's retaining each other (REO) as a concept and practice.