Experiencing meaningfulness at work is important for employee engagement, individual performance, and personal fulfilment. However, research surrounding meaningful employment has predominantly focused upon the experiences of well-educated, adult professionals. To expand theoretical understanding of this concept, this paper investigates perceptions of meaningful employment among youths from Northern England (aged 16–18) with a history of involvement in crime. Interviews demonstrate that young offenders’ criteria for ‘meaningful work’ differ from existing research and is influenced by their self-concept and inherent values as youths from chaotic and impoverished backgrounds. This highlights the subjectivity of this concept. Nonetheless, the findings also indicate that there are instances where work itself makes a broader contribution in discovering meaning, and therefore, certain organisational practices are experienced as meaningful by both young offenders and adult professionals. Thus, this study demonstrates the importance of surveying diverse populations to reach a more comprehensive understanding of meaningful employment.