This dissertation researches the barriers encountered and resiliency learned for Black administrators on their path to becoming superintendents in California. Using critical race theory as the lens of the conceptual framework, this research used a qualitative method. The research questions inquired about how the barriers of mentorship, career pathways, and anti-Blackness affected their career trajectories. The study used interviews with Black California superintendents. This research shed light on how the barriers impacted the journey to the seat of superintendent. The paper concludes with evidence-based recommendations to reduce barriers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]