This paper explores singing as a practice that opens spaces to reflect on the emotional and social costs of ‘failure’ in our roles as advocates for nonviolent social change. Inspired by autoethnographic research on singing and songwriting as reflective practice, I ask: Can singing create spaces to re-imagine ‘failure’ as a catalyst for renewed thinking on nonviolent social change in times of social conflict? This question leverages my own experiences as a ‘failed’ singer and advocate committed to teaching and researching nonviolent social change at a small Canadian university. The connection between singing and nonviolence is not new; however, I argue that creating and documenting singing practices can open up reflections on the ways in which these practices shift perceptions of ‘failure’ that can accompany the work of advocating for change at multiple levels: individual, communal and institutional. Addressing these perceptions can encourage creative engagements with failure as a stigmatised, yet productive space that bridges theory and practice. Such creative engagements include conceptualising critical self-reflexivity as a fundamental dimension of restoring trust in our own capacities to advance nonviolence in our classrooms and communities.