Life span psychological and life course sociological perspectives have long acknowledged the role of historical and sociocultural contexts for individuals’ functioning and development. Secular increases favoring older adults in later born cohorts are widely documented for fluid cognitive performance and well-being. However, less is known about secular trends in further key resources of psychosocial functioning, such as perceptions of constraints, and how these are driven by and associated with well-established and probably interrelated secular trends in several individual difference characteristics, including sociodemographic, religiosity, physical health, cognitive, and social variables. To examine these questions, we compared data from 2 independent local samples of the Longitudinal Aging Study Amsterdam (LASA) obtained 20 years apart, in 1992–1993 (n1992–1993 = 795; age = 55–65 years) versus in 2012–2013 (n2012–2013 = 819; age = 55–65 years). Results revealed that in late midlife, people today perceive fewer constraints than did same-aged peers 20 years ago. These secular trends remained after covarying for individual and cohort differences in physical health, performance-based measures of cognitive functioning (memory), quantitative and qualitative indicators of social support, and self-esteem. The effect size was in the moderate range (d = −.20). We conclude that secular trends such as perceptions of constraints in people’s lives generalize to key psychosocial resources across adulthood and old age. We discuss potential underlying mechanisms and consider practical implications of our findings.