As health care reform strategists increasingly recognize the critically important potential of effective everyday self-care decision making for reducing the burden of illness and the strain on health service systems, we must find ways to understand and support it. In this study, the authors investigate persons with expertise in self-care management of type 2 diabetes, HIV/AIDS, and multiple sclerosis to understand how everyday self-care decision making is learned and experienced. They used interview, think-aloud, and focus groups to construct an account of how persons affected by these chronic diseases make decisions in relation to the choices in their everyday lives and learn to manage the untoward effects of these conditions according to their unique contexts and values. The findings form a conceptual foundation for ongoing inquiry into this complex phenomenon and provide insights that might assist clinicians to understand more fully the responses and attitudes of those they serve.