In this conversation, Doug Crowe and Cynthia Kay dig into one of the hardest questions business owners face: Do I stay, or is it time to move on? Cynthia reflects on her path from investigative journalism to entrepreneurship, sharing how each chapter of her career taught her to recognize when something had run its course. Drawing on her background in broadcasting, she explains how curiosity, pattern recognition, and self-awareness shaped her decision-making over time. Together, they explore what emotional readiness really looks like, why peer-to-peer learning matters so much to entrepreneurs, and how reinvention isn’t a single leap but a ...
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