During the first chapter of his career, Jim Jacoby built a successful, privately-owned agency pioneering user-centered design in finance, healthcare, tech, and manufacturing. Then, at the peak of his success, he took a step back and commissioned a world-renowned designer to build a revolutionary motorcycle. Jim studied the methods and behaviors behind the process, then codified his findings into a system that could be applied in any industry—giving a modern, 21st century twist to the idea of Craftsmanship. Jim then reimagined a user-centered design firm from the ground up, launched an executive coaching program, and established a fine-dining venue. We first met Jim a few years ago at a Sofar Sounds show in Chicago. He and his partner Molly were hosting the concert, and their home environment immediately drew us in. And the more we’ve come to know Jim, the resonance has only grown. Not only has he moved through some courageous shifts in his career and personal life, but he’s also mined some profound insights along the way. Throughout this conversation we discuss the difference between strength and courage, honoring your truth, and finding patience in the process. Jim’s life is a powerful example of the joy that’s waiting for us all on the other side of honoring one’s truth. We loved this hour with Jim and hope it sparks something in you, too.