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Chicago is frequently portrayed as a city of deficits: gang violence and homicides capture the attention of media outlets and the entertainment industry alike; bond-rating firms label the city’s credit as “junk;” and schools are portrayed as “crumbling” and “failing” despite academic gains. As previous sections of this report have emphasized, these challenges are real and worthy of scrutiny. However, addressing these topics in the detail they deserve risks painting a unidimensional portrait of the city. One study finds that many Chicagoans feel that media coverage of the city is too negative and does a poor job of capturing what is actually happening in their neighborhoods. This is especially true among residents living on the city’s South and West Sides. Our conversations with young Chicagoans allow us to identify stories that typically go unrecognized. Young people of color in particular are well aware of the challenges facing the city. However, they also remind us that individuals living on the city’s South and West Sides continue to experience joy, exercise agency, and possess a great deal of pride in their communities even in the face of harsh inequities. Alternative representations of what it is like to live on the South and West sides of the city not only complicate our image of Chicago but lend important insights to policymakers. As the city grapples with continued population loss, city leadership should be attuned to the emotions young people ascribe to their communities. Freedom, agency, and feelings of safety and joy play an important role in how young adults envision their futures in Chicago.