This essay examines how the disappointment of ex-resistance fighters can illuminate the grey zone of founding—the ambiguity of beginning anew against the background of systemic violence that eludes the predominant linear visions of transition. For a theoretical framework, I draw on Hannah Arendt’s insights into the ambiguity of beginning anew as a practice of attunement that takes oppressive practices as points of departure for democratizing political action. I explore how the ex-resisters’ stories of disappointment can invigorate this practice, focusing on their ability to reorient political action towards reframing unjust relationships in a way that guards against systematic exclusions in the future. This essay demonstrates the political relevance of disappointment on the example of a South African ex-resister’s memoir, Pregs Govender’s Love and Courage. Govender’s narrative discloses how experiences of disappointment can orient the ex-resisters’ efforts to confront the complexities of founding obscured from the official story.