'Enterprise' has increasingly become part of the United Kingdom's political grammar and efforts to develop entrepreneurial traits and activities in young people have been a key strand of this policy focus. As the 2008 economic recession saw a curtailed youth labour market, enterprise emerged as an appealing policy 'solution' to youth unemployment. Traditional measures of enterprise chart the numbers of new businesses and their survival rates. This article argues these measures tell us little about new business owners: who they are, their motivations, experiences or, own definitions of success. Further, and crucially, such measures ignore the structural constraints surrounding enterprise and the range of social factors that may determine the extent of ambition, and willingness or capacity to take risks. This article argues that although gender and life stage were contributing factors, the young people's structurally disadvantaged positions emerge as the most significant feature of why the move into self-employment did not tend to increase their economic stability as promised. This provides an important insight into the real-life experiences of young people who are engaging in enterprise activities in the contemporary economic context, as well as the role of third sector organisations in overseeing the transition from education to work.