Although people's outlook on the future tends to be characterized by hope and optimism, over time this outlook often becomes more dire. We review multiple theoretical accounts of this tendency to "sober up" as feedback about outcomes draws near, and we explicate factors critical to promoting these temporal declines in expectations. We then meta-analytically test the impact of these factors on temporal shifts in people's expectations about self-relevant outcomes. The findings reveal a robust and ubiquitous tendency to lower one's expectations as the moment of feedback draws near and implicate multiple contributing processes (declining control, changing accountability pressures, construal level changes, and affect management concerns) as important for this shift. Furthermore, the results reveal important differences in the methodological approaches used to examine temporal shifts in predictions and suggest that timing of predictions relative to outcomes and feedback plays a critical role in the nature of the phenomenon. Overall, the analysis reveals an important exception to positive illusions about the future and suggests that a time-sensitive turn toward pessimism has adaptive functions.