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Islands of the Caribbean region share a specific sociohistorical and geographical legacy that impacts how educational work is conceived of and executed in local contexts. Particularly, school leadership in Grenada is challenged on several fronts, including fiscal shortages, susceptibility to natural disasters, and inadequate teacher and principal preparation. This paper reports on a qualitative study with eight practising school principals in public primary and secondary schools in Grenada. Using a relational approach, the study examined work as a social construct, revealing how principals understood and approached their work as spiritual, altruistic, and charitable imperatives. The paper depicts the substantive challenges of educational work in a Caribbean Island, a fundamental step in cultivating more equitable education systems in this region.