One of the most pressing concerns identified in current European educational discourse is about the transitions of students from school to higher education and from educational institutions to the labour market. Government anxieties over the precariousness of the future has led to increasing regulation and measurement of ‘skills’ and ‘competences’ for students in an attempt to suture over these transitions. However, in doing so, policies risk further alienating and dehumanizing students in turning classrooms into testing zones and places of high risk assessment that pigeonhole students into limited futures. I argue in this paper that if youth are to contribute meaningfully to a future that is, by definition, not something that is certain or knowable in advance, a more appropriate response will be to think about the kinds of sensibility that would help students orient themselves toward a changing and unpredictable world. This paper outlines how a project of facing uncertainty (what the poet John Keats referred to as ‘negative capability’) actually shifts the terms upon which policies and curricular reform can be constructed.