In this chapter, the authors seek to unsettle a number of the community, academic, and policy investments in the problems of young people, education and training, and work. To trouble the character and forms of education and training that can support young people in developing the forms of personhood. Building a biographical account provides a somewhat time sensitive/specific window into the life of the individual that can also record movement and change as it happens, and relationships to larger stories of education, training, work, labour markets. The structured Vocational Education and Training conducted at program by William Angliss was more intense than Kate thought it would be. The authors discuss number of research projects that they have led/participated in that have had a primary interest in exploring the ways in which social enterprise-based Transitional Labour Market Programs structure interventions into the lives of the most marginalised young people, to develop the attributes, and skills that promise to make them employable.