This chapter is about how that which surrounds us and connects us—our contexts—can allow us to think more creatively in telling stories and in envisioning the future. Alex McDowell’s methodology known as World Building provides a way to collaborate in imagining a world from which stories can emerge. This chapter describes how this method was created and how it continues to evolve today as an educational platform for envisioning the future. Case study and survey data show how the educational applications work in practice. In theory and practice McDowell’s approach illustrates the natural, underlying relationship between context and collaboration. Learning about this method is an opportunity to think about the relationship between these two concepts, how they affect one another, and how they can facilitate creative thinking.