Readiness for change (or treatment readiness) is a core concept of many rehabilitation programs for adult and juvenile offenders. The present study examined the experiences of six young people aged 13 to 17 years who participated in Mindfields®, a 6-week self-regulatory intervention aimed at enhancing life skills and goal setting among youths who present with challenging and/or risky behaviour. This article investigates the extent to which: readiness for change influences individual responses to the Mindfields® program; external factors influence the achievement and maintenance of program success; and goal achievement leads to perceptions of self-efficacy and personal control over one's behaviour. Prior to, and on completion of the intervention, participants completed the Mindfields® Assessment Battery that measures goal commitment, social competence, self-regulation, life satisfaction, delinquent involvement, and readiness for change. Findings show the importance of participants’ motivation to make life-changing decisions, but this motivation and promising goals can be compromised by factors external to the individual. Our findings prompt future research into ways in which young people can maintain their motivation and readiness for change, and draw encouragement from less successful outcomes than might have been expected.