Older adult health is often defined in clinical terms. Research has demonstrated that many older adults self-report aging successfully regardless of clinical health status. This qualitative study used claims data to identify older adults on three levels of health status: healthy and active, managing diseases, or very sick, to better understand how health is defined and maintained. In total, 32 participants from two cities were interviewed. Interviews were audio- and video-recorded and then transcribed. Thematic analysis identified five themes: disconnectedness between objective and subjective health; health defined to include psychological and social components; resilience and coping mechanisms indicative of successful aging; social support systems integral to health; and the goal of maintaining functioning. These results indicate the importance of individual perceptions of health rather than just counts of chronic diseases. Health management programs should provide holistic approaches to maximize health outcomes and to promote successful aging.