Leisure activities are a source of meaning and enjoyment for individuals across the lifespan. In this study, we conducted interviews with twenty-four older adults living in four different independent living communities. We present societal and ecological factors and motivations that influenced the way people participated in and decided what constitutes leisure activities. The goal of maintaining physical and cognitive health was often intertwined with motivations to engage in leisure activities. We discuss how this fits into the broader framework of successful aging and implications for technology design. We also provide an example of how findings from this study can be applied to a specific leisure activity: watching television.