On the basis of a survey of the classical learning paradox (as first described by Plato and given its modern formulation by Fodor ), I argue that a kind of professional learning paradox holds, in particular for professionals and professional peer groups attempting to learn new content. Given Wittgenstein's notions of training and "logical grammar" (following Shanker (1986) in this latter formulation) and the situation of professionals who are essentially on their own in learning new things, it is difficult to see how professionals could bootstrap their own understanding. I suggest that the set of practices or language games constitutive of inquiry may serve to help to some degree in this matter. However, this is not a (dis)solution to the learning paradox—especially given that the professional learning paradox is not a philosophical problem. Finally I point out that this proposal connects to political issues concerning the relationship between institutions and professionals, with regard to the kind of environment entailed by the needs of professional learning .