The analytical approach of this article is inspired by C. Wright Mills’ (1959) notion of “the sociological imagination.” Individual experience is viewed through the lens of the wider social context, particularly that of the organization. The socio-organizational context is then viewed through the lens of individual experience. The aim of this bi-directional gaze is to explore the relationship between individual experience and wider society. And in doing so, to identify and reveal the shared motifs—the significant, recurrent themes and patterns—that link and construct personal experience and social world. The aims, findings, and research processes of the original study are rooted in the instrumental epistemology of program evaluation. Specifically, a mixed-method implementation-evaluation of a local non-governmental organization’s Orphans and Vulnerable Children program. The aim of this article is to take the analyses and findings of that evaluation beyond its epistemic roots. Qualitative data were disentangled from the confines of thematic analysis and freed into their original narrative form. This allowed for a deeply reflexive “second reading,” which brings whole narratives into a dialogue with original findings, contextual factors, and sociological discourse. Key conceptual anchors are located in Vanessa May’s ideas on the self and belonging, and in Margaret Wetherell’s writings on affect and emotion. These are important aspects of working with children, particularly orphans and vulnerable children in South Africa, where many fall through the cracks of government’s social services. A second, deeper, qualitative reading of the narratives of children, their parents/caregivers, and the organization’s staff, explores three key pathways of individual and group experience that are inextricably linked to emotions and belonging, and which co-construct the social functioning of the organization itself.