Part of our call as educators is to prepare students for a dynamic and complicated world. Paul Hanstedt helps us understand how vocation and pedagogy intersect. He is author of Creating Wicked Students: Designing Courses for a Complex World and directs the Houston H. Harte Center for Teaching and Learning at Washington and Lee University. Our conversation explores reflective practices, questioning, and listening in the classroom. He offers ways to disrupt patterns and discover fresh approaches for collaborative learning and exploration. Paul’s emphasis on preparing students for the difficulties of life—and engaging in big questions from the first semester through the last—ultimately challenges us to ask students, “what matters?”