Richard Rorty, in his "Consequences of Pragmatism" (1982), acknowledging the pragmatic direction taken by both modern and postmodern philosophy, declared that "James and Dewey were not only waiting at the end of the dialectical road which analytic philosophy traveled, but are waiting at the end of the road which, for example, Foucault and Deleuze are currently traveling" (Rorty, 1982, p. xviii). This paper aims to trace a common direction as a sort of pragmatic trajectory that will map a territory constituting Gilles Deleuze's new image of thought, or rather as he put it, a thought without image. By addressing some of Deleuze's ideas on thinking and learning, especially with regard to the problematics of sources of knowledge, this paper posits the convergence between his philosophical position and Dewey's philosophy of education despite the two being seemingly separated by time, place and culture. The paper further shifts the focus from the factual "knowledge" to an experimental and experiential process of "knowing" and asserts the latter's far-reaching implications for education as a developing and generative practice. (Contains 3 notes.)