Socrates acting as a “gadfly” in Athenian politics is one of the first descriptions of what it entails to engage in political enlightenment. The possibilities of such enlightenment, in particular to engage in critical speech, are addressed in this arti- cle by discussing the ideas of Jürgen Habermas and Michel Foucault. Habermas argues that a radical political idea was articulated in the early modern public sphere; this was the idea of the dissolution of domination through public opin- ion. This understanding is important for Habermas’ later formulations of commu- nicative action and discourse. The latter is contrasted with Foucault’s analysis of truth telling, parrēsia, and it is argued that the risk taking and courage required to speak the truth provide clues for deepening the understanding of what Habermas calls discursive problematization. Truth telling is also considered in relation to the Socratic dialogue, which gives us an idea of the reciprocal and dialogical relations between participants focused on elaborating relations to the self that enable indi- viduals to engage in critical speech and political enlightenment