Increased deployments to combat operation areas have resulted in veterans transitioning from the military in more significant numbers. Likewise, African American veterans are also leaving the military in higher numbers. Transition assistance training is necessary to prepare these veterans for higher education and civilian employment since these are the most likely destinations for the successful transition of this population of veterans. Transition Goals, Plans, Success Program (Transition GPS) prepares military personnel for the transition back to civilian life. Transition GPS focuses on helping military personnel to become career-ready through mandatory curriculum-based training in a classroom setting before departing the military for civilian life. This study aims to understand better the transition experiences of African American veterans, their participation in the Transition GPS program, and the challenges they face obtaining employment and higher education after military service. Moreover, higher education is vital for the self-improvement and economic stability of African American veterans. The participants for this study were six African American veterans who served in the United States Army, Navy, Air Force, and Army National Guard. Each participant served in their respective branch of the military for 20 years or more. Veterans in this study highlighted the challenges they faced during their transition from the military to civilian life and acknowledged the importance of higher education. The themes that emerged are representative of the participants’ life experiences, military transition experiences, and demonstrates higher education’s role in a successful transition. The participants expressed the importance of family during their transitions, but they need help to better understand civilian careers and employment before leaving the military. Furthermore, African American veterans need career counseling to help them understand their transition experiences and help to prepare an adequate resume that translates their military skills into a civilian job match.