In higher education, design thinking is often taught as a process. Yet design cognition resides in action and design practices. Dewey’s pragmatism offers a solid epistemology for design thinking. This paper describes a design research whereby Dewey’s inquiry served as the foundation for educating students. Three extensive educational case studies are presented whereby a design inquiry was introduced and became part of the curricula. It was found that students and coaches struggled with doubts experienced as a result of the co-evolution of problem and solution, means and ends. Four coping mechanisms were observed: (1) focus on problems, risking analysis paralysis; (2) focus on creative problem-solving, risking unsubstantiated design; (3) focus on means, risking fixation; and (4) focus on future ends, risking hanging on to a dream. By establishing a joint practice and a community of learnersthrough show-and share sessions, the students establish solid ground.