We know that real world contexts can help students see the use of mathematics in their lives. Current mathematics textbooks and open source curriculum situate problem solving in the real world, but do so in very different ways. In this workshop, we look at different ways of leveraging real world contexts to design lessons. Participants will learn specific design principles used to develop problems that support students in using their everyday understanding of the real world. Participants will engage with tasks as learners and learn a process for writing or adapting instructional sequences.