Aim We sought to understand strategies employed by ‘Baby Boomers’ to maintain well‐being and facilitate transition to later life. Method A non‐clinical cohort (n = 139) provided qualitative data about well‐being strategies. Thematic data analysis provided insights for those with high and low life satisfaction (based on Satisfaction with Life Scale) and quantitative data from previous waves provided predictors of life satisfaction decades later. Results Longitudinal predictors were depression history (cognitive trait and repeated episodes) and quality of partner's care. ‘Highly satisfied older people’ reported proactive strategies, contrasted with lack of planning by ‘dissatisfied older people’. ‘Resilient older people’, with high life satisfaction despite repeated depressive episodes reported benefit from strategies dealing with adversity, including depression. Discussion Strategies of ‘satisfied older people’ support theories of proactive coping and demonstrate the importance of developing adaptational skills to support later life satisfaction. ‘Resilient older people’ demonstrate that adaptive strategies can lead to achievement of life satisfaction despite repeated depressive episodes.