Is it possible to make the world well without looking deep within, without making yourself well, so to speak? This chapter emphasizes the power of inner work for sustainable, outer transformation by sharing the author’s incredibly personal story, as an award-winning social entrepreneur, inner development advocate, a driver of change, and as a woman committed to standing up for her truth. Her heartfelt account illuminates the impact of understanding how traumatic events shape our lives and responses, how cultivating awareness of personal and professional drivers helps pave a clearer path, and how healing the world within facilitates healing the world beyond. The author is convinced that sustainable entrepreneurship is not a career choice; it’s a call to adventure and depth. And she invites those who are embarking on the journey of sustainable entrepreneurship to grow deeper in their impact while finding their way to wellbeing, through insightful prompts as part of a practical, developmental set of tools.