This paper explores how employment and labor are situated within the lives of homeless youth and is based upon the findings emerging from in-depth interviews with 34 youth in Halifax, Canada. The findings suggest that street-involved and homeless young people are straddling formal and informal work economies while mediating layers of external and internal motivations and tensions. For the most part, youth interviewed engaged in informal money-making activities including panhandling, squeegeeing, busking, making and selling art, performing poetry and/or jokes, among many other creative pursuits. The diversity of these activities demonstrates the entrepreneurial spirit and creativity/resilience of street-involved young people. They are willing to undertake any number of often undesirable tasks to survive. The reality is that the participants in this study could not very easily engage in formal work. In addition, their stories showed how society takes particular effort to criminalize certain types of poverty – in this case much of the informal work in which homeless youth engage.