This study examines the role of planning and plan fulfillment for retirement satisfaction using a dynamic resource theory approach. A 3-year qualitative longitudinal design was deployed with interviews conducted first on the cusp of retirement, then 1 and 2 years after retirement. The final sample comprised 41 individuals from England, 40 from Italy, and 30 from the United States. Realizing plans was found to be linked to retirement satisfaction. However, many retirees adjusted well to retirement without planning in advance, or when plans were thwarted, and sometimes retirement did not live up to expectations despite fulfillment of plans. Psychological resources and resilience were key dimensions of satisfaction regardless of planning. Retirement satisfaction was also associated with social integration, adoption of new social roles, and opportunities to be active within and beyond the private sphere, such as volunteering or participating in leisure oriented clubs or activities. Regardless of planning, the quality of family relationships was a particularly important element for retirement satisfaction or dissatisfaction.