Through a comparative analysis of three case studies built on the intersection of three young adults’ trajectories and three LLL policies in Germany, Italy and Bulgaria, this chapter aims to explore the interplay between opportunity structures and subjective choices. We focus on the educational and professional dimensions, putting them in relation within the LLL policy young adults accessed with their aspirations, self-representations, the living conditions they face in the local context and the welfare (Esping-Andersen, The three worlds of welfare capitalism. Princeton, NJ: Princeton University Press, 1990) and transition (Walther, YOUNG, 14(2), 119–139, 2006) regimes characterizing their countries. Relying on the Capability Approach (Sen, Development as freedom. Oxford: Oxford University Press, 1999; Nussbaum, Women and human development. Cambridge: Cambridge University Press, 2000), we explore how young people’s capacity to cope with challenges and their ability to actively navigate obstacles are influenced by the wider discursive and institutional opportunity structures in which they unfold their life paths. The analysis reveals how youths make their choices according to their “capacity to aspire” (Appadurai 2004) and the social, cultural and economic factors at play in exercising their navigational capacities; being able (or unable) to define life plans potentially constitutes a “new” factor of inequality. The possibilities of better capturing the complex relationship between structural limits, possibilities and subjective aspirations in shaping individuals’ choices and actions within specific opportunity structures are discussed.

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