In this paper we explore young peoples’ normative representations of work. In particular we are interested in the ways young people view work roles which could be considered ‘atypical’ such as young caring or language brokering. Interviewed were 46 young people (15-18 years) some who did, and some who did not engage in the ‘atypical’ work roles of language brokering or young caring. Findings indicated that young people have a strong representation of what a ‘normal’ childhood comprises and that friends, teachers and parents play a mediational role in cementing this contextually. However, respondents presented two alternative representations around engagement in ‘atypical’ roles, with some individuals holding both views at the same time. On the one hand they felt that engagement in ‘atypical’ activities would be experienced as a loss of ‘normal’ childhood. On the other hand a more positive representation of ‘atypical’ childhoods was also drawn on, in which engagement in ‘atypical’ activities was seen as a source of pride and a contributor of additional skills to a child’s development. This opinion was evidenced by both those who had, and those who had not engaged in ‘atypical’ work.