For Black women faculty members and student affairs personnel, this book delineates the needed skills and the range of possible pathways for attaining administrative positions in higher education.This book uses a survey that identifies the skills and knowledge that Black women administrators report as most critical at different stages of their careers as a foundation for the personal narratives of individual administrators’ career progressions. The contributors address barriers, strategies, and considerations such as the comparative merits of starting a career at an HBCU or PWI, or at a public or private institution.Their stories shine light on how to develop the most effective leadership style, how to communicate, and the importance of leading with credibility. They dwell on the necessity of listening to one’s inner voice in guiding decisions, of maintaining integrity and having a clear sense of values, and of developing a realistic sense of personal limitations and abilities. They illustrate how to combine institutional and personal priorities with service to the community; share how the authors carved out their distinct and purposeful career paths; and demonstrate the importance of the mentoring they received and provided along the way. A theoretical chapter provides a frame for reflecting on the paths traveled. These accounts and reflections provide enlightenment, inspiration, and nuggets of wisdom for all Black women who want to advance their careers in higher education.