This article elaborates and defends a thesis prominent in my recent book, "The Formation of Reason"; namely, that "a human being gets to be free in the distinctive way that human beings are free through the acquisition of second nature". My treatment of this thesis in The Formation of Reason is much influenced by the philosophy of John McDowell. McDowell himself, however, is notoriously reluctant to offer a theory of second nature. In this article, I explain his reasons for taking this stance and show how, for all that, his work contains much that illuminates the idea of second nature and its relation to freedom. I make this argument by focusing on a number of McDowell's papers on Aristotle and Wittgenstein that I do not discuss in detail in my book. Finally, I consider the objection that although McDowell recognizes second nature as a property of individuals, he mistakenly rejects the idea of second nature in external form. I argue that his works do in fact contain resources to countenance second nature externalized, so long as we keep that idea insulated from the constructivist theories of normativity that McDowell rightly rejects. Understanding our thesis aright is, I maintain, a necessary condition of a compelling conception of the social dimensions of mind and of the end of education. (Contains 18 footnotes.)