Past research has posited that occupations are distinct and exclusive communities of workers and used single-entry questions in surveys to measure occupational self-identification. Our study challenges that view by reporting the existence of polyoccupationalism, or workers’ simultaneous identification with multiple occupations. We predict this phenomenon co-occurs with postindustrial forms of work organization and that its expression varies with workers’ position in the occupational structure. Using a survey on creative workers that uniquely allowed respondents to identify with multiple occupations, we find individuals report higher levels of polyoccupationalism when their work is more contract- and project-based, net of other individual and occupational attributes. We further show that polyoccupationalism takes different forms at the top and the bottom of the occupational hierarchy: whereas the polyoccupationalism of high-status “entrepreneurs” stretches expertise—they identify with occupations that are similar in status but functionally distinct—that of lower-status “hustlers” stretches status—the occupations they report involve similar tasks but stand farther apart on the occupational status scale. We discuss the implications of these findings for understanding workers’ occupational identities and the dynamics of occupational hierarchies.