This short paper is a response to Richard Smith's "Abstraction and finitude: education, chance and democracy". In his paper Smith contends that a rationalist agenda dominates education and democracy today, and that this agenda by rendering us insensitive to the tragic dimension of life, breeds a sense of "hubris", or arrogance towards fate which is fuelled by an inordinate confidence in our knowledge. In the worlds of education and politics it has led to an obsession with management and transparency, and to students who fear to take risks. As a specific example of this, he takes up the recent fixation in universities with learning how to learn, which he says leads to an over-emphasis on skills in the curriculum, and to an "audit" culture. While sympathising with much of his analysis of the latter, my counter-suggestion is that the contemporary world lacks anything but a sense of the contingency of things, to the contrary, that at the heart of its mangerialist culture and its performatist ethos lies the need for reassurance. My response focuses on the politics of the self-directed learner that lies at the heart of the lifelong learning literature, on learning how to learn, on the notion of transparency and on the transparent society, and on the politics of contingency and scepticism.