This qualitative study considers the development of adolescent offending and examines a range of potential causes rooted in the issues of truancy, peer pressure, and educational and parental disengagement. Ten adult offenders recently released from prison were accessed through a probation service in the North West of England. Participants (M age = 35.2, S.D = 8.51) were interviewed about the indictable offences that they perpetrated between the ages of 12–16. Thematic analysis uncovered several key themes related to substance misuse and broader enjoyment of risk-taking behaviours, financial gain and the desire to develop a recognised criminal status, alongside fear and rejection of authority. In general, educational disengagement led to stronger associations with anti-social peers from whom acceptance was sought and offending identities were constructed around. Longer-term consequences of time spent with anti-social peers included substance abuse, more serious criminality, and increased risk-taking behaviour. The implications of the findings are discussed in the context of early interventions.