In this episode of That Pivotal Moment of Change, I sit down with Tim Gilligan, whose career has taken him from immersive theater productions in New York to the world of design operations at Capital One. Tim’s story challenges the idea of linear career paths and explores how each chapter—no matter how unexpected—can become a powerful building block. We talk about the transition from stagecraft to systems thinking, the importance of resilience as a resource rather than a mindset, and the value of asking for help when the way forward feels uncertain. Tim opens up about learning to close chapters without clean endings, how community and coalition-building have shaped his leadership, and why storytelling remains central to his work. This is a conversation about integration over reinvention, purpose over titles, and how the most meaningful careers are often the ones we never saw coming.