Using personal narratives as a form of inquiry, the author describes the learning experience of colonized subjects being educated in colonial-based school systems. The author goes on to juxtapose such experiences with the challenge of teaching racialized, culturally, and linguistically diverse students in a standardized test-driven driven school context such as that of the United States. Further, the author talks about the way and the extent to which the colonial legacy, sustained by western neocolonial and neoliberal policies, has continued to influence the teaching practices of teachers as well as the learning of students both in the West and so-called Third World countries like Haiti. Drawing on these experiences, the author makes suggestions as to how one can counter neo-colonial and hegemonic practices affecting the learning, the well-being, and the teaching practices of both students and teachers.