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The transitional phase leading from late adolescence to the establishment of identity as an adult is filled with the potential for peril or promise. Several late adolescent journeys will be recounted in this chapter, narrated in different voices, and drawn from diverse sources. In particular, I will consider a literary text, written on the eve of the author's 21st birthday, as well as presenting clinical material drawn from analytic work with an adolescent in crisis. By employing a Winnicottian lens, I will consider these journeys as creative attempts to project the self through potential space and potential time. Creativity and the capacity for play enable some late adolescents to begin successfully assuming the responsibilities of adulthood; for others, the attempt breaks down, is aborted, or takes a malignant course. Thus, adolescent dreams can come to chart the path toward an establishment of secure adult identity, or they may evolve into a nightmare, engendering fragmentation and possible antisocial behavior. Within the therapeutic setting, the establishment of vital, mutual engagement, as well as the provision of a secure play space, in which creative, productive dreams can emerge, has significant positive implications for analytic work with troubled late adolescents and young adults.