James T. Robilotta (Leading Imperfectly, TEDx) is now a life coach and public speaker, but it took a lot of ups and downs to get there. We talk about how writing his book was the most polarizing thing he has done in his life, why the brain always feels stupid for letting the heart steer, chewing on his own words about authenticity and vulnerability as his marriage was crumbling, starting the first hip hop improv team in NY - North Coast, and how his whole life he was taught to be kind to other people, but it took 32 years to be kind to himself.