This work is guided by the idea that Wittgenstein’s thought opens the door to a more profound break with the philosophical tradition than has been generally recognized. It brings this insight to bear on some basic problems of philosophy. Wittgenstein’s work has been assimilated to the analytic tradition in such a way that its radical character has been made nearly invisible. In fact, Wittgenstein formulates a basic critique of a predominant conception in contemporary analytic philosophy, according to which language can be seen as a formal structure describable in general terms. This conception neglects the profound context-dependence of the way things said are to be understood, thus imposing a schematic view of the connections between words and life. By distancing us from the life we live with language, it makes the problems of philosophy come to appear intractable. In this work, the attempt is made to show how philosophical confusions are to be overcome through attending to the actual use of words in conversation.