In and out of school technology uses present themselves differently. Namely, outside structures more often than not reflect distributed knowledge models, while inside structures mirror hierarchical ones. Drawing upon theoretical frames of cultural sociology and critical pedagogy, the paper aims to contrast the structures of participation outside and inside school walls. We illustrate that looking outside the classroom gives us insight into how teachers might more readily and actively engage youth in meaningful applications activity. Specifically, we use the former to inform the later. We conclude with implication for using outside technology participation to reconceptualize inside learning designs.