The central argument of this article is that historical changes in longevity in Western societies, globalization, and the weakening of social expectations regarding the timing of developmental goals lead to a compression of the time for pursuing highly demanding developmental goals related to work and family in late young and middle adulthood. The expectation of longevity might lead adults to construct a "bucket list," postponing important leisure and social goals to the postretirement phase. Jointly, the weakening of age-related social expectations and the long postretirement phase in Western societies might result in a stronger segregation of the life course: education in "emerging adulthood," work and family in later young and middle adulthood, leisure and social goals in later adulthood. This segregation also conforms to a Western cultural script following the Protestant work ethic of delaying gratification by pursuing obligatory goals first (work, family) and only then turn to "play" after retirement (leisure, social goals), a time with relatively few obligations and social expectations. The segmentation of the life course has implications for self-regulatory demands, such that the importance of goal selection increases in emerging adulthood, the importance of managing multiple goals in late young and middle adulthood, and the importance of self-regulation for the pursuit of ill-defined goals in old age. Taken together, historical changes in the increased life expectancy in Western countries and weakened age-related expectations represent a challenge and an opportunity for developmental regulation. (PsycInfo Database Record (c) 2020 APA, all rights reserved).