This work explores the aspirations of young people in a youth training programme and how structure and agency shape their aspirations. Transition policy is currently based on the pathways framework which provides many different educational and training ‘pathways’ to assist young people to move from school to work. For youth in Youth Training their ‘pathway’ is often non-linear and complex; not having followed conventional or mainstream transitional markers they are easily labelled problem-youth and ‘at-risk’ or vulnerable to failure. This study endeavoured to move beyond the labels of young in Youth Training to explore their stories in the context of the lived-experiences. It gave them the opportunity to voice their aspirations for the future and considered the structure or societal constraints associated with their transitional experience.