How have the immediate school-to-work transition and the early career changed in different labour market entry regimes since the early 1980s? How do institutional frameworks differ with regard to insecurity perception? Ellen Ebralidze investigates these topics from a cross-national perspective while focusing on Denmark, the darling of flexicurity literature. The results show that in all the labour market entry regimes, the school-towork transition has become increasingly difficult, and flexible forms of work are more typical in the first job. Furthermore, the liberal institutional framework of the United States seems to produce a similarly low degree of job-loss worry among young people in their early career as the Danish paradigm.