This thesis attempts to test Richard Rorty's ideal character, the Liberal Ironist, against what Charles Taylor provides as various necessary but insufficient phenomenological conditions that allow for the possibility for self-reflection. In the absence of such conditions, Taylor holds, the very idea of a clear identity, a clear sense of Who one is, becomes either unintelligible or utterly trivial. After arguing that Rorty's ideal figure is likely to suffer from what we may call an identity crisis, I go on to offer some friendly amendments for Rorty. I claim that his ideal figure is one that should be replaced or augmented such that her specific characteristics and traits mesh more closely with the actual phenomenology of our moral experience. In the final chapter, I attempt to bridge what has to that point seemed like an unbridgeable methodological gulf between the descriptive, phenomenological project of Taylor and Rorty's largely prescriptive pragmatism. This reconciliation takes the form of Wittgensteinian and Deweyan reminders that should like to see both projects (Taylor's and Rorty's respectively) as diverse sets of tools. I conclude, in accordance with a meta-philosophical pragmatism that I deduce from the later Wittgenstein, that one set of tools need not trump another in any philosophically deep or a priori manner. My claim, in short, is that both philosophical strategies can be viewed as apt depending only on the philosophical work they are expected to fulfill.