In this episode of The Five Regrets to Avoid in Life, Doug Holladay and host Jamie Haith take on one of the most pervasive traps in modern life: a narrow definition of success. Together, they unpack how chasing status, wealth, or achievement—while culturally celebrated—can leave us feeling empty or off-course.

Doug shares stories from decades of working with high-performing leaders who, despite their accomplishments, often feel a quiet sense of disillusionment. What happens when you reach the top of the ladder only to realize it was leaning against the wrong wall?

This episode challenges listeners to redefine success on their own terms—anchored in meaning, relationships, and personal values—rather than external benchmarks. With wisdom and humility, Doug offers a vision of success that is expansive, human, and deeply fulfilling.