This dissertation examines the transitional states of agents undergoing profound personal transformation. In each of three papers, I provide an account of a possible obstacle to stably acquiring new values: alienation, vacillation, and ambivalence. These obstacles are forms of inner conflict where our evaluative attitudes come apart, threatening our very selves. Alienation: Jacinta enrolls in a poetry course, aspiring to develop a poetic outlook. Faced with the arduous task of writing a sonnet, she would much rather go out. What reason does Jacinta have to keep working? One answer is that poetry is valuable intrinsically, i.e., for its own sake. However, Jacinta is taking the course precisely because she does not yet value poetry intrinsically. Agnes Callard argues that such cases raise a challenge for reasons internalism, a view requiring a proper connection between one’s current cares and concerns and her reasons to act. I consider several possible internalist replies. The most promising stresses that aspirants have some grasp of the relevant value, which I argue suffices to justify their aspirational actions. Ultimately, I retort that Callard’s insistence on the differences between the aspirant and her target self risks leaving the aspirant alienated from that self. Vacillation: Consider a lapsed Catholic who feels guilty about having casual sex even as she disputes that it is morally wrong or a man raised in an observant Jewish household who feels compelled to keep Kosher long after rejecting the Jewish faith. Such cases exemplify a form of inner conflict I call vacillation, which resembles Tamar Gendler’s belief-discordant aliefs. I point to vacillation as a significant psychic cost of transitioning between outlooks, or ideologically laden ways of navigating the social world. Thus, I highlight that remedying what Miranda Fricker has called hermeneutical injustice goes beyond giving people resources to make sense of their experiences. Ambivalence: Sam belongs to a community in which hunting is a major cultural practice, which he values for its own sake. However, he has also come to care deeply about animal welfare. I analyze this case as one of ambivalence, drawing and building on Harry Frankfurt’s account. I introduce the notion of a constitutive desire: a desire for something only insofar as it is an essential or constitutive part of something one values intrinsically. I defend the unificationist ideal, according to which being a psychically unified self is highly ethically and rationally important, against critics of Frankfurtian wholeheartedness.