This chapter explores the intricate relationship between entrepreneurial success and personal well-being, highlighting the interplay between ambition, mental health, and fulfilment. It examines how psychological resilience, coping mechanisms, and support systems contribute to both personal and professional outcomes for entrepreneurs. By emphasizing the significance of work-life balance and community networks, the chapter argues that well-being is integral to sustainable entrepreneurial success. Furthermore, it identifies future research directions that can deepen our understanding of this relationship, including the need for longitudinal studies and interdisciplinary approaches. Ultimately, this exploration underscores that personal fulfilment and entrepreneurial achievement are interdependent, advocating for a holistic view that nurtures both aspects to foster a thriving entrepreneurial landscape.