The article addresses school-to-work transitions among young women in a strongly male dominated professional sphere – the transport industry. Drawing on interviews with two girls over the time span 2015–2022 and visits to their upper secondary school 2016–2019, the study focuses on how power structures related to gender play out in the positioning that takes place in school and workplaces: How the girls were positioned socially and in relation to professional qualification, and how they positioned themselves in these respects. The findings indicate significant changes in discourse and practice when the girls transitioned from students to employees, changes which in the article are discussed in the framework of ‘inequality regimes’ and through the lens of the ‘glass funnel’ metaphor. Linking the funnel metaphor to the framework of inequality regimes broadens the picture to consider how young people are exposed to generally increasing inequalities in labour markets where institutions and organisations are affected by neoliberal economic policies, weakened collective protection of workers and wider wage gaps. With individualisation and insecurity, young people like the two girls in focus in this article, are increasingly left to fend for themselves in a harsh labour market.