This study uses a microcosmic ethnographic epistemology, critical theory (CT), critical race theory (CRT), critical ethnography (CE), and critical discourse analysis (CDA), to show the nuances of the lived experiences of a diverse group of educators as they negotiated and renegotiated their self-labeling, identity, and culture, and reflected on the importance of education across a spectrum of scales. We examined how participants negotiated and renegotiated their educator identity, as contextualized by their lived experiences and family socialization, and the impact of these on the lens through which they perceived the world. The research question investigated how self-identification affects the ways in which one operates within selected socially constructed institutions. Research findings indicated that the participants were critically conscious of their individual cultural citizenship and identities, and how these have fostered in them the ability to meaningfully respond to the diverse educational needs that they have encountered in their role as educators, with colleagues and with students.