Educators from across disciplines experiment with ways of developing students’ creative confidence through design thinking. In all levels of education today we hear about active, project-based, experiential, and student-centric teaching strategies. Teaching in the 21st century is not only a skill; it’s a mindset shift. Therefore, educator development needs to be long-term and continuous to be effective. An in-service teacher training workshop is great for exposing teachers to new ideas, but a true change in the classroom requires long-term work. Our experience shows, and data confirms, that long-term coaching is a powerful strategy for helping teachers shift their practice.