The article introduces the problematics of the classical two-valued logic on which Western thought is generally based, outlining that under the conditions of its logical assumptions the subject I is situated in a world that it cannot address. In this context, the article outlines a short history of cybernetics and the shift from first- to second-order cybernetics. The basic principles of Gordon Pask’s 1976 Conversation Theory are introduced. It is argued that this second-order theory grants agency to others through a re-conception of living beings as You logically transcending the I. The key principles of Conversation Theory are set in relation to the poetic forms of discourse that played a key role in art as well as philosophical thinking in China in the past. Second-order thinking, the article argues, is essentially poetic. It foregoes prediction in favour of the potentiality of encountering tomorrow’s delights.