This paper deals with Praxis as the central paradigm in Richard Rorty's philosophy. Considering philosophy as praxis transforms the way we understand philosophy and draws our attention to literature that is more practical. Is truth the purpose of philosophy? How can philosophy as praxis and literary works contribute to the improvement of human condition? The study asserts that Richard Rorty was not able to justify his views on philosophy and literature, and develop a new value, irony, until he extricated the practical paradigm from its antithesis (the theoretical paradigm). By embodying the value of irony, philosophy and literature can fulfil their potential to disavow the theoretical and foundational paradigm, to become devoted to hope and to moral and social progress.