This article was designed to provide an in-depth perspective of a virtual simulated city utilized in a doctoral program to engage learners in the critical elements of risk taking and decision making. The distance learning course promotes critical thinking and real-world application within a safe and artificial environment. Students’ collaborative efforts created a mission and vision to base their decisions for the future landscape of the city. This simulation hones effective leadership skills in a distance learning platform. Two perspectives from both student and faculty illustrate the effectiveness of group dynamics, communication, collaboration and leadership used in a systems thinking approach.