This qualitative case study investigates how service-learning may enable self-direction and the development of a critical consciousness for marginalized high school students by exploring the dynamics of service-learning through a theoretical framework of critical theory. Service-learning is theorized to counter the oppressive nature of schooling as defined by critical theorists; however, little research exists to clarify the implications of the pedagogy on student empowerment. I consider the negotiation of power and knowledge that may empower students, redefining their experience of schooling and their identities as learners. By exploring processes of empowerment and the social structures created through service-learning, I document three marginalized, male, urban high school students' self-authorship as they negotiate learning spaces within community. Data analysis revealed how service-learning legitimized lived experience and enabled the re-writing of self through the construction of new social/intellectual spaces. Participants' experiences offer insight into the pedagogy of service-learning for encountering transformational moments between self, society, and other.