In his later lectures, published as "The Hermeneutics of the Subject," Michel Foucault surveys different modalities of obtaining "truth" about one's self and the world: from Socrates to the Cynics, Stoics, Epicureans and early church writers. Genealogically tracing this opposition between knowing "self and world," he occasionally invites phenomenological enquiry into how this epistemic couplet bears on education. Drawing on three vignettes familiar to educators, my investigation explores modes of discovering self and world through counselling (truth-telling), distributed governance in the classroom and the arts of writing. In each case we confront a paradox of freedom, in that agency is needed, already, to liberate the self from the world. An exegetical task is to show how Foucault worked through this philosophical problem, of relevance to many situations in education, by re-reading Kant, Nietzsche and Heidegger.