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Male sex work (MSW) research has been generally limited to the examination of “social problems.” Although there have been studies on occupational aspects, pointed examinations of the occupational environment, detailing the contemporary nature of the field, are rare. Research on nuances of the occupational context of MSW, providing insight on the rapidly changing face of the field, is wanting. Semistructured interviews were conducted with 20 escorts in Brisbane, Australia. This study explored job success, indicating that success in the field was well articulated, possibly highlighting that male independent escorting is becoming a professionalized occupation, with a shift away from current stigmatized understandings.