Alisa Berger was the founding principal at both the NYC iSchool, a New York City public high school, and the Mott Hall II school, a NYC public middle school. Devon Larosa is the former principal of La Follette High School in Madison, Wisconsin and currently works as the Deputy Chief of Schools - High School Network for the Chicago public school system. This robust conversation covers several topics including: lessons we can take from the virtual classroom and integrate into traditional teaching; how to create real spaces for student healing and mental health; what is needed to make the classroom more relevant to students; how to better prepare students so they can pursue their passions; balancing teaching critical issues even when teacher biases are present; and how care, compassion and empathy should be at the core of all education systems.