The growth of self-employed enterprise and the supposed ascendancy of the enterprising self' are commonly associated with the forces of flexibilization and individualization in contemporary work arrangements. What is driving these forces and their effects can be understood, in part, by examining what psychoanalytic theory would name desire. The focus here is upon the dynamics of desire among individuals who leave jobs to enter the growing ranks of the self-employed. Drawing from findings of a qualitative study of such new women entrepreneurs across Canada, changing concepts of the enterprising self are explored with specific attention to the relations between their desires and their conception of work. This article addresses three questions in particular: How is desire enmeshed in the development of enterprising selves? How do women come to desire work through self-employed enterprise, often entailing personal and economic pain? Do these desires configure possibilities for new alternatives in enterprise? The study findings suggest not only that contradictory desires are closely integrated with identity in the transition to enterprise, but also that some women's desires appear to form resistance to aspects of conventional models of business development. Through analysis informed by psychoanalytic theories of desire, these impulses are named 'transgressive desires' and their importance is demonstrated in their links to the new models of entrepreneurism that seem to be appearing among these women's enterprises.