Researchers have discussed the significance of Black male educators in secondary and post-secondary education for decades. While there is extensive research on the impact of Black male teachers, education administrators, and those in the professoriate, there is a noticeable gap concerning the experiences of Black male student affairs staff in higher education. This qualitative study fills that void by analyzing the experiences of Black male student affairs professionals who have transitioned out of the higher education profession at American universities within the past decade. This research utilizes counter-storytelling as its methodology to offer fresh insights and alternative viewpoints. Employing Critical Race Theory as the primary analytical framework provides a comprehensive understanding of the racialized experiences of Black men in the student affairs profession. Additionally, this research examines these experiences' impact on Black men's career trajectories, uncovering significant barriers to advancement. It explores how Black men navigate the racialization of their bodies in the student affairs workspace, allowing a glimpse into the challenges they encounter in maintaining authenticity while conforming to professional norms. The recommendations include urging university leaders to foster inclusive workspaces and providing proactive pathways for Black men to thrive in student affairs despite systemic biases. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]