As he reflected on his upcoming 60th birthday, Rob LaZebnik, a writer for The Simpsons, saw his worst fear coming true: He was becoming boring. Rather than embracing the challenge and growth that comes from novel experiences, he found himself settling into the comfort of routine and predictability. To break this downward spiral toward tedium, he challenged himself to try 60 new things in his 60th year. Both The Wall Street Journal and Inc.com have documented his experience. Reading these articles collided almost perfectly with a project I had been trying to launch in one of my classes: experiential learning. For the past couple of years, I had challenged my students to choose something new that they wanted to learn over the course of the semester and document their experience. As they trudged through the ambiguity of learning something new, I struggled to frame this project in a way that was, all at once, personally meaningful, academically rigorous, and sufficiently scaffolded. In a moment that felt like a deus ex machina, LaZebnik’s perspective provided me with a new way of structuring this assignment, which I now call the Risk Challenge.