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 thoughtful, often uncomfortable process.
Key Takeaways
- You always have the option to choose differently or to walk away.
- A fading sense of passion is often the first signal that something needs to change.
- Emotional readiness is just as important as financial readiness when making a move.
- Peer-to-peer learning is one of the most powerful tools for business owners.
- Reinvention is a process, not a single decision and it’s more accessible than ever.
Get your copy of “Should You Stay or Should You Go” on Amazon: https://a.co/d/2P4wVuo