Sterling is often wrong, but always seeks truth. He teaches performing arts at SEEQS: the School for Examining Essential Questions of Sustainability. As a debater, he ranked quarterfinalist at the Yale Intervarsity, semifinalist at the United States Universities Debating Championship and runner-up at the Pan Pacific, Pan American, and U.S. Western Regional Debating Championships. Sterling holds an Ed.M. from the Arts in Education Program at the Harvard Graduate School of Education. He is currently studying for a Ph.D. at the University of Hawai‘i at Mānoa College of Education.