In this paper I examine problems besetting forms of philosophical and social critique that are motivated by the ‘hermeneutics of suspicion’ and normatively oriented to the goal of ‘unmasking’. I argue that there is an urgent need to correct the one-sided emphasis on ‘unmasking’, and we can do this by reorienting critique to the practice of individual and social transformation. The argument goes like this. The practice of unmasking critique has split off from utopian projects in whose service it was originally placed, and has become the vehicle of a self-consuming, practice-crippling skepticism that – from Friedrich von Schlegel to Paul de Man and Richard Rorty – goes by the name of irony or ironist theory. Postmodernism, in one of its aspects, is the latest form of this skepticism. I interpret postmodernism as the manifestation of a crisis of confidence (in our ideals and in our agency) and as an ironization of critique. Drawing upon Kant, Hegel, Nietzsche, Heidegger and Foucault, I reformulate the normative demands of critique such that its practice avoids the problem of self-reference while responding to the problem of self-reassurance.