This article provides a detailed ethnographic description of skateboarding's main career opportunities and contributes to arguments about subculture theory and the impact of specific subcultures on cities. Professional street skateboarders perform tricks on obstacles in the urban environment and publish these tricks in magazines and videos to share with other members of the subculture. This need for documentation and dissemination of skateboard tricks, as well as the need to design and distribute subculture media, skateboards and skateboarding products, makes skateboarding a self-sustaining industry and provides skaters with an opportunity for subculture careers. These careers are in skating and also the ancillary careers necessary to support this industry. These subculture careers have a positive impact on individual skaters by providing opportunities, in many cases where none existed, and also upon the urban centers where this industry is most prominent by drawing creative, talented people to the city to participate in the subculture and quite possibly even make a career.