This paper analyzes the symbolism of George Kennan’s famous “X” article relative to the challenges of contemporary post-socialist and post-conflict transitions. It unpacks recent developments in the field of contemporary political discourse, discussing the critical application of practices such as thinking with your heart, parrhesis, and pathos, as well as Kennan’s suggestion of the significance of uncertainty and reflection for global relations. The central question is: What would Kennan write in an X Article to the societies and states in transition? While various definitions of the term “parrhesis” exist, this paper employs both the definition suggested by Michel Foucault who understood it as “fearless speech” and Eric Voegelin who closely follows Plato’s meaning linking it with “heart”, i.e. vision of the spiritual, an existential (dis)order of representatives of a society.