This article will explore two potentially disruptive developmental phenomena that occur during life transitions. One is the role of anticipatory haunting during adolescence, and the other is the strict adherence to an already defined life narrative at the gate to young adulthood (Levy-Warren, 2016a, 2016b). Historically, in psychoanalytic theory, we have looked at flaws in an adolescent’s foundation as causal in adolescent paralysis. Anticipatory haunting, fearing what is to come, also can be traumatic enough to disrupt an adolescent’s development. Similarly, in the transition from late adolescence to young adulthood, we have assumed that the past must be left behind for the youth to progress in development and that focusing on the past can inhibit the envisioning of a future. In this instance, the necessity for a particular kind of reworking of the young adult’s history so that a future can be envisioned is articulated. Each of these points of view represents a departure from traditional ways of understanding and treating developmental disruptions.