How to account for the interplay of change and permanence in human identity? I discuss Peirce's contribution to solve a paradox: the certainty of humans of always being themselves, always the same person, despite the overtly evolving nature of the self. Intriguingly, what epitomizes the regular and predictable nature of habit and of habit-taking centrally involves the incidence of the most volatile element in Peirce's theory, namely, Orience ("free originality"), spontaneity. To describe the emergence of change in identity construed as a process of habit-taking, this chapter examines three decades of Peircean writings on habit (1878–1908). A conclusion of this study is how fundamental in his account is the role of the imagination when it comes to the shaping of habits. That elusive element in humanity bears tangible consequences, since imaginary considerations "will affect my real action should those circumstances be realized" (CP 2.148). Phaneroscopy provides an essential support to Peirce's mature account of habit.