In this article we examine the career paths of top-level managers in the arts. By analysing the training and work history of 23 managers in a variety of arts organisations we evaluate the utility of several existing theories for understanding careers that are characterised by low levels of initial knowledge, the absence of a clear method of entry and the influence of a central interest in artistic activity. Our findings show that while both boundaryless and protean models shed some light on the career trajectories of arts managers, theories based on personality and identity have a large part to play in explaining their choices. The factors describing patterns of movement exhibited by arts managers are likely to be applicable to other groups emerging into a less structured, rapidly changing employment context.