High-stakes testing that became the norm after the No Child Left Behind Act of 2001 helped condition students to strive for correct answers for clear problems, all on the first try. However, the iterative process inherent in designing requires risk-taking to conduct a trial-and-error process of defining problems and exploring possible solutions. This design research project was operated with Miami University Graphic Design students to test their willingness to take risks in their coursework to achieve their self-defined measures of success. Students identified that improving their skills was how they defined success. An interaction design assignment involving front-end coding was modified to test students’ comfort taking risks to grow their skills. Most students took risks in the assignment to grow their interaction design skills. The project revealed that closer attention to student motivation when developing learning experiences could help students make the transition to practicing design as an iterative process fraught with risk.