While the majority of creative, performing and literary artists are self-employed, relatively few tertiary arts schools attempt to develop capabilities for venture creation and management (and entrepreneurship more broadly) and still fewer do so effectively. This article asks why this is the case. It addresses underlying conceptual and philosophical issues encountered by arts educators, arguing that in all three senses of the term – new venture creation, career self-management, and being enterprising – entrepreneurship is essential to career success in the arts. However, the practice of entrepreneurship in the arts is significantly different from the practice of entrepreneurship in business, in terms of the artist’s drivers and aims, as well as the nature of entrepreneurial opportunities, contexts and processes. These differences mean that entrepreneurship curricula cannot simply be imported from business schools. This article also examines the arts-idiosyncratic challenge of negotiating distinctive and potentially conflicting entrepreneurial aims, using career identity theory. It concludes by suggesting strategies by which adaptive entrepreneurial artist identities can be developed through higher education programs.