Only two percent of teachers in the United States are African American males (Wallace & Gagen, 2019). If this trend continues, the vast majority of students in America will never encounter an African American male teacher (Burns Thomas, 2020). The purpose of this research study was to explore the motivations and obstacles that African American males encounter as they enter the teaching profession. This qualitative study consisted of interviewing eight African American male educators regarding their motivations and obstacles on their journey to the classroom. Participants were asked open ended questions to afford them an opportunity to share their lived experiences. A narrative analysis was conducted of participants? interviews. The major findings of this study revealed that African American males are motivated to become teachers by family, by wanting to become role models, as an extension of coaching, and through the influence of teachers throughout their educational experience. Participants shared that lacking a support system, not pursuing rigorous college preparatory coursework, and isolation and exclusion were major obstacles they had to overcome. This study suggest that stakeholders have to be intentional in the recruitment and support of potential African American male teachers. Stakeholders can use the information gained from this study to create policies, provide academic and financial supports, and mentoring opportunities that are tailored to the recruitment of African American male teachers. [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.]