The research reported here was funded by the UK Department for Education and Skills to consider the influence of the school on the decision by young people to participate in learning on completion of compulsory schooling. A national sample of 24 schools across England participated in this study. Research methods included focus group interviews with students aged 14 and 15 years; interviews with head teachers, heads of year and career advisors in each of the 24 schools; and parental questionnaires for each student interviewed. This article considers the findings of the project in terms of the impact of educational interventions on young peoples' decision-making processes and finds that young people require experience of, rather than "cold" information about, their post-school options. Young people seek to manage risks, by gaining first-hand experience or relying on trusted relationships and social networks. This study found that official informational sources are not trusted; they are treated as high risk, whereas experiential events are trusted and have high impact on decision making. Family, friends and social networks are trusted sources of information and influence decision making. This creates a paradox whereby a young person's trusted sources of information, guidance and support may also be treated as high risk. A challenge for the education and advisory process therefore is to produce high-trust relationships and minimize the risks associated with post-compulsory education. This article uses the conceptual work related to reflexivity to explore the issues of risk and trust in a rapidly changing world and connects these aspects of social theory directly to the experience of young people making decisions about their transitions and life course. (Contains 2 figures.)