When the New York Times ran a story in 2021 about our skateboarding research, it highlighted skateboarding as a site of safety, community, and agency for youth from racially minoritized backgrounds. A faculty member at our institution, however, questioned the need to study skateboarding communities and wondered why we, the study authors, had done nothing to protect them from the perilous skateboarding students who traverse campus. Odds are Academic Leader readers have dodged a harried skater en route from one campus building to another. A few might even bristle at the idea of skateboarders meriting research attention. Understandable. We recognize that skateboarders can appear to be reckless—or under certain conditions actually be reckless. Yet deeper scrutiny of skateboarders’ dexterity reveals that their nimbleness applies to their movement not only through physical space but also through life. We posit that skateboarders offer expertise that might serve academic leaders well as they seek ways to support students’ well-being.