Using the bicycle as a catalyst, SHIFT proposes a number of design interventions to help raise Philadelphia’s quality of life. To facilitate this proposed shift, this thesis leverages the Human Centered Design Process through ethnographic field studies, visual data synthesis and an iterative design approach. The meaning of “interested but concerned” was juxtaposed against the theories of latent demand to highlight and unpack the economic benefits that a 3% shift in ridership could afford this fair city. Finally, a semantic view on the role of politics and communities inPhiladelphia is unraveled. Focusing on the wickedness of the encountered problem and expressing how design solutions are but a small piece of the puzzle.