This article views adult development through the lens of daily life experiences and recent historical changes in these experiences. In particular, it examines whether theories that postulate general linear increases in well-being throughout adulthood still hold during times of less prosperity and more uncertainty. Descriptive analyses of the National Study of Daily Experiences chart show how stress in the daily lives of Americans may have changed from the 1990s (N = 1,499) to the 2010s (N = 782). Results revealed that adults in the 2010s reported experiencing stressors on 2% more days than in the 1990s, which translates to an additional week of stressors across a year. Participants in the 2010s also reported that stressors were more severe and posed more risks to future plans and finances and that they experienced more distress. These historical changes were particularly pronounced among middle-aged adults (e.g., proportion of stressor days increased by 19%, and perceived risks to finances and to future plans rose by 61% and 52%, respectively). As a consequence, age-related linear increases in well-being observed from young adulthood to midlife in the 1990s were no longer observed in the 2010s. If further studies continue to replicate our findings, traditional theories of adult well-being that were developed and empirically tested during times of relative economic prosperity may need to be reevaluated in light of the changes in middle adulthood currently observed in this historic period. (PsycInfo Database Record (c) 2020 APA, all rights reserved).