Since 2005, I Challenge Myself, has been helping high school students in underprivileged areas of New York City develop leadership and workplace skills, as well as confidence and self-esteem, through endurance cycling training and rides, including a semester-culminating Century (100 mile) bike ride. For many students, not only is it their first experience on a bike, but also their first meaningful opportunity to break the cycle of obesity and related illnesses that are prevalent in low-income communities. The program is offered as an elective class to each high school’s students, generally as an after-school extension of their existing physical education classes. In addition to coaches, ICM provides each student with a quality Cannondale or Trek road bike and arranges for the bike’s storage and overall maintenance. As one of ICM’s students, who had never ridden a bike before, wrote in a self-assessment after 3 months in the program: “Can one thing change you forever? I am not sure, but I do know that over the course of this semester cycling with I Challenge Myself has changed me into a more positive and healthy person. The more I push myself in the program, the more I want to excel in every other part of my life. The program has given me the confidence to believe in, and trust, myself.”