Despite the call for instructional designers to employ design thinking as a means to foster creativity in problem-solving, many students struggle with enacting creative risk. While several studies have been conducted studying how instructional designers engage in problem-solving to contend with project constraints, few have addressed whether this is due to their confidence and abilities to engage in creative risk. This paper discusses how instructional designers can promote creative risk in instructional design pedagogy through three constructs: ideation, dynamic decision-making, and failure-based learning. Implications and future research are also discussed.