This episode explores the mental health challenges faced by entrepreneurs, particularly the loneliness, stress, and setbacks inherent in the entrepreneurial journey. Against this backdrop, Kevin Oldham, a certified exit planning advisor, shares his personal experiences with addiction and mental health struggles, emphasizing the importance of recognizing vulnerabilities and seeking support. More significantly, the conversation delves into practical strategies for building resilience, including the concept of "VUCA fit"—adapting to a volatile, uncertain, complex, and ambiguous world—and the power of establishing small, controllable wins to counter feelings of defeat. For instance, Kevin describes his daily ritual of collecting and sorting mail as a personal victory that boosts his confidence. The discussion also highlights the often-overlooked importance of planning for business exits, with Kevin revealing that 75% of business owners regret selling their companies within a year due to unpreparedness for the identity shift and the misconception that money alone brings happiness. Ultimately, the episode underscores the need for self-awareness, support networks, and proactive planning to navigate the emotional rollercoaster of entrepreneurship and achieve a fulfilling exit.