Ongoing behavioral research has documented the growing prevalence of adolescent health risk behaviors, such as tobacco use, sexual activity, alcohol and other substance use, nutritional behavior, physical inactivity, and intentional injury. Newer youth risk behaviors, such as pathological gambling, are emerging as threats to public health. Risk, risk taking, and risk behavior are important and relevant topics for exploring in health education classes. The goal of health educators, teachers, administrators, and parents alike should be to encourage youth to engage in constructive risk-taking behavior rather than alternative destructive behavior. In this article, the authors provide the Risky Business learning activity for students to be able to reinforce concepts and facilitate understanding of the role of risk taking in their lives.