In this article we build a theoretical framework with which to analyse trendsetting learning biographies, i.e. biographies that are prototypical realisations of a cultural script about how young people learn and live in late modernity. In the current debate on lifelong learning in knowledge-based societies learners are interpreted in an economical and psychological sense. Notions from youth, life course, and generation sociology are, however, needed to fully understand trendsetting learning biographies. We selected 14 Dutch younger adults (varying by class and gender) with these biographies, analysed their biographical narrations, and explored the importance of structure and agency in their learning biographies. Their life stories reveal a structured interrelation between an integrated life conception, special forms of social capital, and the key competence of biographicity. We conclude with some thought on the complications of theory building when interpreting learners in a biographical sense.