Interactive technology can support exertion activities, with many examples focusing on improving athletic performance. We see an opportunity for technology to also support extreme sports such as skateboarding, which often focus primarily on the experience of doing tricks rather than on athletic performance. However, there is little knowledge on how to design for such experiences. In response, we designed 12 basic skateboarding prototypes inspired by skateboarding theory. Using an autoethnographical approach, we skated with each of these and reflected on our experiences in order to derive four design themes: location of feedback in relation to the skater's body, timing of feedback in relation to peaks in emotions after attempts, aspects of the trick emphasized by feedback, and aesthetic fittingness of feedback. As an exemplification and elaboration of this work we designed an interactive skateboarding system called Copy Paste Skate, using the 4 themes as a guide. We hope our work will inspire and guide designers and practitioners in the field of interactive systems for skateboarding and trick-focused sports in general, and will further our understanding of how to design for the active human body.