In this week’s episode of Better Business, Better Life, Debra Chantry-Taylor is joined by Kerry Boulton, an experienced exit planner, business coach, and investor, for a candid conversation about what really happens when business owners don’t plan their exit.

Drawing on decades of lived experience, Kerry shares her journey from running a major division in the 1980s to owning, exiting, and reinvesting in multiple businesses. She unpacks a confronting statistic from the Exit Planning Institute: 73% of business owners regret selling their business, largely because they failed to plan both the exit itself and what comes next.

Together, Debra and Kerry explore what it truly means to be exit-ready, from strong financials, systems, and succession planning, to reducing owner dependency and thinking deeply about purpose beyond the business. The conversation also dives into family business succession, the emotional realities of exiting, and why starting at least three years early can make all the difference.

This episode is a powerful reminder that exiting a business isn’t a single transaction, it’s a transition. And done well, it can set you up not just for financial security, but for a meaningful and intentional next chapter of life.