Leave When They Want You to Stay: Leadership Lessons from Former United Way Worldwide CEO Brian Gallagher

“Leave when they want you to stay.”That’s a lesson most leaders learn quietly—if at all.In this episode of Who Moved My Career?!, Nicole McNamara sits down with Brian Gallagher, former CEO of United Way Worldwide, for a rare, deeply personal conversation about a career he doesn’t often unpack publicly.Over more than three decades at United Way, Brian helped reshape the organization’s mission, brand, and global impact. Here, he shares the inside story—what it’s like to stay in one role for a long time, how leadership slowly changes you, and the moment he knew it was time to leave, even when others wanted him to stay.Brian opens up about imposter syndrome, early life experiences that shaped his leadership, and why building a portfolio career after United Way—now at Leargas Group—brought clarity, purpose, and renewed fulfillment.This episode is for leaders, nonprofit professionals, and high performers navigating career pivots, wrestling with identity beyond a title, or wondering what legacy really means when the work evolves.🎧 Listen for an honest look behind a remarkable career—and the courage it takes to turn the page.