In this essay, the author proposes that the field of Philosophy of Education is in search of its own second wind and can find guidance in the work and life of William James. This paper is meant to invite conversation on the challenges faced and provide potential solutions in the field. The goal is to find the "cash-value" of the field within the changing academic landscape through the concept of the second wind. In this paper the author suggests that in order for philosophers of education to find their second wind, they as a field must be willing to engage in more discussion and public intellectualism, as James had done throughout his life, and find the "regenerative properties" that exist in these processes that push us from the first wind to the second wind.