Increasingly, the transitions between institutions of higher education and working life are attracting interest and becoming more important due to changes both in students’ academic “trajectories” and in the organisation and nature of working life, tasks and careers. The first part of this article discusses some experiences from a project, aiming to facilitate these transitions for students in co-called co-op education, i.e. study programmes that intersperse academic studies with internships. The project consisted of students writing cases, based on their experiences of these internships, as a way of integrating learning in the workplace with learning in the classroom. The second part of the article relates the cases and the writing of them to the concept of boundary objects in order to draw some conclusions about the nature and design of such objects. The conclusion is that such cases seem well suited as a basis for an intelligible translation between academia and working life.