In China’s evolving social and economic landscape, private enterprises and entrepreneurs face significant challenges stemming from an unpredictable regulatory environment, the gradual shift toward a state-driven economy, and escalating U.S.-China geopolitical tensions. High-net-worth entrepreneurs represent an increasingly significant portion of the world’s wealthy individuals, but little is known about the factors that shape their life trajectories in midlife. By examining their conceptualizations of life trajectories and future planning, this study sought to uncover the key factors that have influenced their past experiences and their personal and developmental objectives for the future. This information can serve as a reference for designing learning programs that meet the developmental needs of midlife entrepreneurs in China. This qualitative, exploratory study examines the life trajectories and future planning of midlife high-net-worth private entrepreneurs in China. Data were collected through in-depth, semi-structured interviews with 30 participants. Thematic analysis, combining both deductive and inductive approaches, was conducted to identify patterns and influential factors in their personal and professional development. The study reveals that, within the research group, life trajectories are shaped by a dynamic interplay of external and internal factors. Key external influences include social and historical forces, unexpected events, and family foundations, while focus, persistence, and a commitment to continuous learning emerge as critical internal drivers of success. Participants prioritize personal growth through learning, new experiences, and maintaining good health, alongside career goals of business longevity and stability. The findings offer a preliminary understanding of this group’s perceptions of midlife, uncovering connections between past experiences and current perspectives, along with their learning aspirations and preferred methods. This study also underscores the distinct needs of this demographic, emphasizing the importance of reevaluating existing learning programs to better address these requirements. Additionally, it calls for further research on the midlife population and the development of a theoretical framework for midlife development that reflects the evolving characteristics of this group across diverse cultural contexts. Keywords: Midlife, high-net-worth, Chinese entrepreneur, life course, developmental influences, future planning, personal development, professional development