Moral and political theories, insofar as they are based on the fragile life of human beings, usually incorporate a reflection on the role of uncertainty or contingency. The question remains however, how exactly do we experience ‘uncertainty’? Can it show us different faces, to which we then react in different ways? If so, what is the meaning of such multiplicity for the exercise of agency? Comparing Bergson’s inquiry into the modern belief in chance with Jean-Marie Guyau’s reflections on the love (...) of risk, I examine the moral significance of different ways of relating to uncertainty, and analyze their respective pedagogical purchase regarding the constitution of human freedom. When confronted with the unknown future, human agency gets easily trapped in the vicious and vertiginous circle of impotence and omnipotence. The contrast between Bergson and Guyau illuminates this problem, showing how our relation to uncertainty informs our identity, our capacity for action, and our sense of obligation. (shrink)