Popular education tools can be utilized to address complex urban regulations and unequal power relationships within urban planning. Guided by Friedman’s argument that planning needs to have utopian thinking (2000), this research proposes what planning ought to be, rather than only focusing on what is. Using street vendor education as a catalyst for popular education models related to planning regulations, this thesis centers on the Vendor Power Guide in New York City as a main case study, and explores the components of the guide that made it such a successful tool for transforming community awareness around unfair vending regulations and supporting vendor interactions with law enforcement. Ultimately, this project identifies the ways in which urban planners should use popular education within their work to encourage citizen power and democracy.