Seniors strive to achieve aging well by engaging in entrepreneurial activities subsequent to ceasing their organizational employment. While this is a common practice in many societies, scant research exists on what motivates seniors to engage in entrepreneurial activities once they end their formal employment. We adopt the self-determination theory (SDT) to investigate the effects of goal contents and motives on the well-being among seniors who launch their entrepreneurship journeys. Based on in-depth interviews with senior entrepreneurs in China, India, and Turkey, we contribute to extant knowledge by linking separate paradigms. These are as follows: goal contents and intrinsic motivation-driven entrepreneurship, management of inner and outer challenges, and achievement of the eventual outcome of aging well. We also investigate the culture-specific drivers of senior entrepreneurship in a comparative framework.