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The developmental path of the transformative self is not straightforward, easy, or uniform. This chapter charts how the transformative self itself develops over time, from the theoretical perspectives of Eriksonian identity development and eudaimonic growth. The chapter provides an overview of how one’s degrees of identity exploration and commitment in a world of others shape one’s development over time. High versus low degrees of exploration and commitment yield four identity statuses or pathways: searchers, traditionalists, pathmakers, and drifters. This chapter surveys recent research and theoretical adjustments on the Eriksonian ideal, notably regarding non-idealized pathways of development. Excerpts from the bildungsroman genre illustrate the internal and interpersonal conflicts of eudaimonic growth that arise along all four pathways, plus non-ideal developments, from the perspectives of male and female characters, and then in the contexts of relationships, work, and religious views.