The background of this paper is the political action programme initiated by the Swedish government aiming at increasing the cooperation between school and working life. The idea of closer connections between school and working life is not uncontroversial. This paper presents two different perspectives on the subject. One perspective argues that the social context is vital for learning in order to create meaningful learning in real-life settings as learning is rooted in practice and social participation. From this perspective close connections between school and working life is desired. Seen from another perspective school is supposed to be a separate practice in order to acculturate learning to make it applicable in a variety of contexts. Closer connections with working life are therefore not needed. The political idea of closer connections between school and working life can be found within a neoliberal discourse talking about the role of schooling as fostering self-directed lifelong learners within the so-called knowledge society. That raises the question of what kind of learning and knowledge that is regarded as useful, both in society in general and in working life, today and for the future and whether a closer connection between school and working life will serve that purpose.