Contemplative practices offer a promising lens for thinking about how people navigate change, vulnerability, and the emotional texture of later life. This article examines how such practices extend ideas of healthy aging, drawing on interviews and focus groups (n = 24) from an 8-week mind–body course. Participants reported strong satisfaction with the course, noting improvements in physical and mental health, and a notable shift towards greater kindness, openness, and curiosity towards themselves and others. Aiming to understand the key elements of contemplative training, our analysis identified three notable themes: learning to be with emotionally challenging experiences; normalizing change and vulnerability; and the ongoing development of a toolkit. Participants also reported a heightened ability to cope with challenges, make intentional life choices, and foster a positive attitude. From a gerontological perspective, the program offered helpful resources for adapting to change and embracing vulnerability as fundamental components of healthy aging. We also suggest the value of a life course perspective, which enables us to imagine contemplative practice as a form of training for aging well.