--- - |2 Abstract This paper examines the affective dimensions of new forms of informal entrepreneurial work carried out in spaces of unemployment. Situating the analysis within contemporary scholarship on deservingness and on affect and labour, I shed light on the forms of entrepreneurial labour that rely upon affect‐driven economies of exchange underpinned by moral judgements of deservingness, value and worth. In particular, this paper draws on a multi‐city (Melbourne, London, San Francisco) study of homeless street press sellers (The Big Issue and Street Sheet) to explore the ways in which contemporary practices of charity and care are carried out through individualized market‐place exchanges. Sellers’ accounts of their work reveal how smiling and being (or looking) happy is a performative expectation that must be managed in the face of poverty and precarity. - The British Journal of Sociology, EarlyView.