This paper poses a rarely asked question--Re-engagement to where? Or to what valued social purpose for the young people concerned? Drawing from a larger project funded by the Australian Research Council, the paper analyses the "portraits" of two young people whose lives were seemingly better within a re-engagement programme, but whose lives were severely circumscribed by the narrow vocationalism offered in the programme. More concerning was the fact that the considerable natural talents and skills of these young people were neither acknowledged nor used as the basis to improve their life chances or opportunities.