We discuss the major processes involved in individuals' motivation and self-regulation of goal striving throughout the life course. While much is regulated based on the biological and societal scaffolding of lifespan development, certain challenges for motivation and self-regulation are more substantial and need to be managed by the individual, providing opportunities for researchers for testing the limits of individual capacities in developmental regulation. These challenging circumstances include major changes in age-graded opportunities for goal pursuit, uncertain or obfuscated opportunities, and major unexpected losses of control. Under such challenging circumstances, the consequences of individual differences in motivational self-regulation, such as optimism, action vs. state orientation, and goal-disengagement capacity are enhanced and may contribute to adaptive patterns of developmental regulation.