Changing labour markets, increased calls for selection and excellence, and increased diversity and individualisation have repercussions on how educational systems can prepare youth for work, optimise knowledge production, achieve equality of opportunity, and socialise students into active civic engagement. This paper discusses four central tasks of schooling and examines to what extent societal developments challenge education policy to deliver on the tasks at hand. Particular attention is given to the challenges Europe’s strongly diversified educational systems are currently facing. Both the Netherlands and Germany, for example, have been offering vocationally oriented pathways alongside traditional academic higher education for some time. But today’s ongoing changes in job descriptions, mainly due to ever-accelerating technological developments, are causing a risk of skills obsolescence which can only be avoided by continuous upskilling and/or reskilling of a sufficiently flexible workforce. Overcoming differences of intelligence as well as differences of diverse socioeconomic, ethnic and linguistic backgrounds by way of education is another challenge, as is fostering “soft” skills and political awareness. This paper investigates the effectiveness of current education systems in preparing citizens for a functioning modern society.