This symposium brings together 4 studies from 3 countries to examine the multiple influences shaping educational and career choices of young people. The first paper by Schoon and Jenkins focuses on career choices of young people in England born in 1990 (Millennials) and 2000 (Generation Z), examining the role of social background, individual characteristics and agency as predictors in times of social change. The second paper by Gomensoro and colleagues investigates the impact of the (mis)match of parents’ and children’s expectations on post-compulsory educational attainment in Switzerland. The third paper by Hofherr and Walper asks if aspirations before graduation mediate the associations between characteristics of the family, students’ personality and their previous school career with their career trajectories after graduation. The fourth paper by Mele, Schoon and Burger focus on individuals who are “Not in Education, Employment, or Training” (NEET) during the school-to-work transition, examining the mechanisms underpinning socioeconomic differences in NEET experiences by taking into account interactions between social origins and young people’s agentic behaviours. Together these studies provide a comprehensive understanding of the multiple influences shaping educational and career choices and attainment in different cultural contexts and countries characterised by different transition regimes, highlighting similarities and differences of challenges and opportunities and providing a more in-depth understanding of the social ecology of career development processes.