Implicating oneself in oppression provokes uncertainty, shame and anxiety, and identity destabilizations. Yet anti-oppressive texts often denigrate these experiences, participating in forces I call “compulsory sound-mindedness.” Narratives of three women confronting their complicity illustrate the workings of compulsory sound-mindedness: a white Canadian recognizing the racism in her development work and both a white woman and a racialized Muslim reflecting on their complicity in ongoing Canadian colonization. The three narratives devalue affect, uncertainty, and destabilized identity. They also reveal these denigrated experiences as fundamental to personal-is-political ethical transformation. Compulsory sound-mindedness cannot consistently prevent people from journeying with pain, uncertainty, and coming undone. But when people undertake such journeys, compulsory sound-mindedness frames pain, identity destabilization, and uncertainty as regrettable and without value. I advocate that people cultivate a “troubled consciousness” by journeying with internalized accountability narratives, uncertainties, painful feelings, and destabilizations of a straightforwardly moral self.