The Portuguese crisis affected the country’s collective identity, and ‘the timing of life’ at which it struck individual lives in this case is also significant. Quantitative figures show that young people were particularly affected by this crisis. However, a long-run qualitative approach provides a multilayered and quite complex view of what this crisis is embedding in young people’s lives and minds. In qualitative research on ‘middle class’ transitions to adulthood carried out in 2009, 52 young adults were interviewed about their educational, residential, occupational and romantic lives. In a follow-up study, these individuals’ trajectories, plans and expectations are now updated; their past and present confronted; and effects of the crisis on their lives questioned. The discussion is held in the form of a critical approach to the theories of individualisation, and goes to the heart of the ‘generation in itself’ vs. ‘generation for itself’ and ‘biographies of choice’ vs. ‘discourses of choice’ debates.