The paper describes my personal journey toward psychoanalytic training amidst the heightened political and cultural polarization of race and ethnicity. As a “woman of color,” I highlight the individual and institutional contradictions I encountered during my graduate studies in social work and in my exposure to the culture of two psychoanalytic training institutes. In both settings, aggressively deployed diversity initiatives intended to increase openness and inclusiveness and implement antiracist agendas often result in ideological rigidity and are antithetical to the crucial value of critical listening that is the foundation of any generative clinical encounter. These initiatives not only have the potential to erode the intellectual integrity of institutions devoted to learning, they can unwittingly reaffirm a racist narrative and further entrench the division between races.