There is now overwhelming evidence that daily actions and habits profoundly influence short-term and long-term health and quality of life. Helping individuals make more positive choices in the areas of physical activity, weight management, nutritional practices, and not using tobacco products is a shared responsibility among physicians, other health care workers, health care systems, and the individual patients themselves. Although some progress has been made in these areas, health care systems have been slow to respond to this important imperative. This article describes one health care system, Orlando Health, and its initiative to incorporate lifestyle medicine concepts into its core operating principles. Great progress has been made in the past 18 months in this initiative although numerous challenges remain. The authors enumerate both progress and challenges. They hope the experience at Orlando Health will challenge and inspire other health care systems to also take a more proactive stance in incorporating lifestyle medicine into their culture and core operating principles.