Breaking stereotypes and changing generational outcomes of historically excluded students requires educators who are willing to be what civil rights leader John Lewis called "good troublemakers." Transformational, culturally competent educators can make a significant impact in the lives of students, classrooms, and communities. This research studies the impact of teaching experience of the Children's Defense Fund Freedom Schools Servant Leader Interns on young educators themselves. This study reveals how Servant Leader Interns were transformed by the process of teaching in ways that influenced their sense of self-authorship, their career aspirations, and expectations of how education should be.