This qualitative study utilized one-on-one interviews to examine the lived experience of Black males who have successfully joined the teaching profession and moved into school administration. Their experiences shed light on factors that help attract African American males to the profession and continue to be educators. This study's research is based on Herzberg et al.'s (1959) motivation-hygiene theory. This theory addresses which factors impact job satisfaction and dissatisfaction. Participants in the study expressed that they are motivated by their desire to impact students and make a difference. They emphasized the importance of representation and shared that relationships with school and district staff influenced their decision to become educators and remain in the profession. Participants expressed that the current teaching demographics could be improved by providing quality support to educators, improving financial compensation, and developing leaders. [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.]