There is a kind of anxiety of thought and action that exists between the "binaries" of Philosophy; between idealism and realism, epistemology and ontology, morality and relativism, etc; the division that is so prominent in the analytical and continental traditions.
With Rorty we get this release, this gentle pat on the shoulder and the consoling words "...we didn't get it either..." Pragmatism, a movement typically American made with Dewey and James and is wonderfully articulated in Rorty, and particularly this book (one of his later). The general thesis; Philosophy (with a big "P") as formalised by Plato, is a 2500 year failed project; this is the project of universal non-contingent truth-seeking, of developing non-historical structures and systems of thought that provide a "conditions for the possibility.." of all reality. The Pragmatists simply declare this as a rubbish set of questions to ask and answer. Pragmatists are not really saying that there is no "Truth", but, to quote from an essay in the Consequences of Pragmatism;
Pragmatists think that the history of attempts to isolate the True, the Good, or to define the word "true" or "good" supports their suspicion that there is no interesting work to be done in this area.
In Contingency, Irony, and Solidarity, Rorty considers philosophy is simply another form of literature, which prompts the question what other literary texts might we use to "change the questions" held in high regard by Philosophy--an attempt to avoid privileging one vocabulary. Here the term irony (or ironist) becomes the catch-cry for a type of thought and action that is aware that their vocabulary is just 1 possible vocabulary, that the contingency of language suggest that an ironic stance is the "best we can do". This is Nietzsche through-and-through. I think the weak point in the text is Solidarity; he seems to simply collapse and prescribe Liberalism--but then again, this might be ironic.
The problem with Rorty, I suspect, is the problem with all philosophers: a dearth of humility. But then if one had sufficient humility, would one pursue philosophy at all? Perhaps a prerequisite for philosophical pursuits is a belief in one's own ability to understand the answers and to choose the "right" ones.
I figured that out long ago, which is why I gave up on becoming a philosopher. Perhaps I've become one after all, but if so, then an "accidental" philosopher -- not through conscious or deliberate effort.