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During their transition from lower to upper secondary education, young peoplemake educational and occupational choices driven by their aspirations. Such aspirations are shaped by the individuals’ social environment, their idea of what seems achievable and desirable, and their experiences. Therefore, aspirations can change during the transitional phase. In this article, we explore the development of educational and occupational aspirations of young people over three years. At the start of the study period, the students were attending the lower track in lower secondary education, the so‐called Neue Mittelschule (8th grade), in the city of Vienna in the 2017–2018 academic year. Drawing on the panel survey data (2018–2020) of the Pathways to the Future project, we simultaneously explore stability and change of educational and occupational aspirations. We describe different patterns of change in aspirations and analyse the influence of sociodemographic characteristics and prior achievement on these patterns. Using latent transition analysis, we identify 11 patterns of aspirations with important differences depending on social background. Most of the students have stable aspirations. However, the results show that school performance, migration background, and the level of parental education play important roles in explaining different levels and patterns of aspirations over time. These longitudinal analyses of educational and occupational aspirations provide important insights into the transition process.

In this article, we are interested in the differences in the educational pathways and subsequent labour market outcomes by social origin and gender. We apply sequence analyses to model the educational trajectories and conduct regression analyses to determine how the individual’s own social status and the salary at labour market entry differs. First, our results show that educational pathways vary by parental status and gender when controlling for reading and mathematics/science skills. Men and pupils with a lower socioeconomic background are overrepresented in vocational education, whereas women and pupils with a more privileged socioeconomic background more often pursue general and academic tracks. Second, these different trajectories lead to unequal occupational status and income. Besides these indirect effects, significant direct effects of parental status and gender on the individual’s own occupational status and salary can be found. Together, these findings provide a broad overview of the emergence of inequalities by gender and social origin over the early life course, ranging from differences in skills learned in school to labour market outcomes.

This article presents how young people in educational measures experience and discuss tensions between structural and individualised challenges they face in the transition from school to work. The findings are based on an Austrian citizen social science research project that involved conducting participatory research in Vienna with 33 young people between the ages of 15 and 23 years who are in measures for early school leavers that are preparing for further education and training. These co‐researchers struggle with constant comparisons to “norm” biographies and their accompanying social pressure as they try to meet the high expectations of school, work, and family. Additionally, mental health was a prominent issue, as the young co‐researchers experience stigma and a lack of professional support, which can impede their access to the labour market. The results of our research indicate that young people in employment measures require a more inclusive school and work environment that supports them regardless of their origin, family background, appearance, or mental health status. They negotiate the tension between individual employability and structural disadvantage and demand a recognised place in society, a request that connects to current debates concerning the individualisation of transitions from school to work.