Amy Green Deines discusses the role of architectural and design education that extends outside of the insular walls of the academy and describes how her teaching and research interests stem from an interdisciplinary approach that seeks to encompass the realities and challenges of an ever-changing society. The chapter describes projects that started with a variety of questions that generated curiosity and desire to answer these questions through design thinking and critical position: What is the word on the street? What is the word in the neighborhood and communities? How does the street affect the neighborhood or district behind or beyond? The chapter describes a variety of solutions that were driven by conversations with a large community and stakeholders. The chapter discusses how outreach and inclusion of the community expanded her ability to pursue passionate and practical solutions that defined real concerns both socially and politically with the mutual goal of improving communities through the design curriculum.