The government wants more people to start up new small enterprises. In practice, this is likely to mean more sole traders without employees, a heterogeneous group sometimes identified with, and sometimes distinguished from, small enterprises. In this paper, we confront that contradiction, drawing upon academic and policy‐oriented writing on small firms and upon a wider literature on labour markets and employment trends. Being self‐employed is not synonymous with being enterprising, but most self‐employed people will need skills associated with enterprise to survive. We overview the cultural sector, which has been identified as a key growth sector for jobs and one in which very small businesses and self‐employed individuals predominate. We explore in depth the “enterprising” behaviour of a subgroup of the cultural sector, people offering creative services to the print and broadcast media on a self‐employed basis. Our particular focus is upon how they form and manage working relationships. The expectation was that, while few would formally become employers, collaborative, colleague‐like working patterns would be adopted to avoid isolation and overcome the vulnerability of small size. This was true, but only for a very small group. For the most part, links with other self‐employed people were tentative and fraught with suspicion. Distrust was pervasive and often coexisted painfully with a desire to form new links for information seeking, sociability and to combat the commercial disadvantages of working alone. Typically, the most important working relationships were with employees of client companies, and many were determined to see these links as longterm, personal and not purely commercial. There was a marked lack of skills in negotiating and marketing.

Recognising their growing role in public services, this article draws on the notion of ‘enactment’ to argue that the internet and social media (I&SM) need to be understood in particular institutional, organisational and social contexts. Focusing on street‐level bureaucrats who deliver frontline services, we explore efforts to integrate I&SM into youth work with clients who are thought to be ‘digitally savvy’ but also in need of protection from the ‘online world’. As clients can be vulnerable and trust is a key relational component, organisation–practitioner–client boundaries are complex and under continuous renegotiation. However, the layering of new virtual channels of interaction adds extra complexity. This change necessitates the development of innovative routines, practices and protocols, but these are being developed in a wider social context where the norms of using social media have not caught up with practice and the use of these tools is still often surrounded by moral panic.