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This paper explores school principals’ work in postcolonial Grenada, highlighting how three particular understandings principals hold about their work, namely as spiritual caretakers, building managers, and chief custodians, shape a set of interesting work practices in attendant ways. The paper engages postcolonial theory, social learning theory, and theories of social and cultural reproduction in painting a picture of the link between socialization, thinking and enactment in the context of the work of school principals. The paper invites scholars to reconsider, from the perspective of the Grenadian postcolonial context, the lens through which we conceive of and conceptualize work for Grenadian school leaders, and (re)imagine how we might better support principal preparation in former colonized and marginalized territories.