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Background: Previous research has shown that tendencies to tenaciously pursue goals and flexibly adapt goals independently relate to well-being in adults in mid-to-late life, but research has not tested whether these tendencies interact. For example, tenacity may only predict well-being in combination with flexibility. This research tests whether these tendencies interact to predict changes in health-related outcomes.Methods: A large cohort of people (n = 5,666), initially aged 55–56, completed measures of flexibility, tenacity, health-related outcomes (physical health, depression, hostility), as well as demographics. Participants provided follow-up data on all measures ten years later. Moderation analysis was used to test whether flexibility and tenacity interacted to predict changes in the health-related outcomes over the period.Results: The interaction between tenacity and flexibility significantly predicted changes in depression, hostility, and physical ill-health symptoms over ten years, such that highly flexible and tenacious individuals experienced the largest decreases in symptoms of depression, hostility, and physical ill-health.Conclusions: The interaction between flexibility and tenacity predicts greater well-being, such that one is most protective when an individual also scores highly on the other. The combination of flexibility and tenacity in the pursuit of personal goals may mean individuals can enjoy gains associated with goal pursuit without the detrimental effects of persevering in blocked goals.