The entrepreneurial experience is not for the faint of heart. Due to the stress associated with starting a new business, it can challenge the well-being of even the best intended entrepreneurs, especially those early on in their journey, whom I call aspiring entrepreneurs (AE). It is possible for an AE to flourish, where they thrive and continue to grow through the experience, as long as they invest in certain key well-being dimensions that positive psychology researchers and practitioners have identified as foundational to entrepreneurial flourishing. This paper explores three of these dimensions, (1) purpose in life, (2) autonomy, and (3) positive relationships with others; and provides a literature review on their potential impact of the AE’s ability to flourish, even during difficult trials and challenges.