Entrepreneurs in their 50s and beyond face significant identity shifts and well-being challenges as they transition out of the businesses they have built. Grounded in Super’s career-development framework and utilizing the Eisenhardt Method for case study analysis, this research explores the entrepreneurial exit process during the maturity and decline stages. With an average business tenure of 11 years, these entrepreneurs encounter emotional and practical hurdles, such as health concerns, financial pressures, and shifting priorities. The study highlights valuing identity diversification and social support in easing the transition, revealing that financial success alone does not guarantee positive post-exit well-being. Gender differences show women prioritize sustainability and family, while men focus on growth and professional identity. These insights underscore the need for early exit planning and holistic support for successful entrepreneurial succession and retirement strategies. JEL CLASSIFICATION: L26: Entrepreneurship; D91: Intertemporal Household Choice; Life Cycle Models and Saving; M14: Corporate Culture; Diversity; Social Responsibility; J14: Economics of the Elderly; Economics of the Handicapped; Non-labor Market Discrimination; I31: General Welfare, Well-being