Meet Michael Dowling, the President and CEO of Northwell Health, the biggest healthcare provider in the State of New York. Their hospitals, like many around the country, battled against COVID-19, and are now responding to the variants spreading rapidly across the country. Michael has fascinating leadership observations from COVID-19 that translate well to every challenge. In the conversation, he shares his own personal story of resilience, differentiates having a title from being a leader, and explains why rule-breaking is critical to innovation. Michael also tells us why hurling, an (often violent) Gaelic Irish sport, has affected his own leadership. Seldom do Stan and Chris speak to a leader with a challenge like the one Michael Dowling faced leading the massive healthcare system during the pandemic. The conversation provides wisdom, offers humor, and a refreshing honesty and perspective that gives us much to think about as the pandemic continues.