A plethora of competing ideological versions of enterprise are currently being promoted in pre‐ and post‐16 education and training. Dominant among these models is enterprise as self‐employment in small business. While moves to transform the educational system (and, indeed, whole regions of the country) in the name of economic enterprise proceed apace, there has been little in the way of independent, critical analysis of the consequences of the rise of this enterprise movement for young people. This paper explores the experience of youth enterprise for young adults in a depressed area of Britain: Cleveland. It draws on ethnographic interviews with 100 18‐ to 25‐year‐olds who have attempted to join the enterprise culture with their new, small businesses. The paper concentrates on the experiences of ‘runners’, ‘fallers’ and ‘plodders’ in the enterprise stakes and highlights some of the contradictions in current small‐business revivalism and enterprise promotion policies.