The term ￜlifestyle enterpriseￜ is often used to describe enterprising in small enterprises, and particularly those small enterprises involved in tourism. Although this lifestyle enterprising phenomenon has been the subject of scholarly investigations since at least the late 1980s, conceptual and theoretical development remains lacking. Typically conceived in objectivist terms as a form of entrepreneurship, much of the research has proceeded from positivist point of views, with interpretivist and, especially, constructionist perspectives only lately emerging. Taking this latter perspective as the point of departure, this study investigates the social construction of lifestyle enterprise from sites in Southern Sweden and Australia. Adopting a sociological perspective, inspired by the social theory of Pierre Bourdieu and borrowing concepts from institutional theory, the study aims to gain insight into the meanings that inform, and thus constitute, lifestyle enterprising practice. Utilising grounded theory methodology, gathering materials through ethnographic observation and open and active interviews, the study offers insights into the meanings that constitute lifestyle enterprising. Findings portray lifestyle enterprising as a contested social field wherein contestation centres on the meaning of products. Enterprisers contest the constitution of products as commodities to negotiate their relation to markets.