In this thought-provoking discussion, Ian Rowe, a Senior Fellow at the American Enterprise Institute and co-founder of Vertex Partnership Academies, argues that incorporating wokeness in education might hinder rather than help students. In contrast, Altheria Caldera, a Senior Professorial Lecturer at American University, advocates for its benefits in fostering empathy and societal awareness. They explore the complexities of teaching systemic racism, the role of historical narratives, and the importance of a balanced approach to education that empowers students while promoting inclusivity.