The Heartland Alliance Writing Group convened weekly at the Leland Apartments in Uptown, Chicago, during January and February of 2017. The group consisted of residents in a Heartland Alliance Permanent Supportive Housing (PSH) program. PSH combines affordable housing with wraparound services for people who are at risk of or have experienced homelessness. The authors came together once a week for two months to talk, reflect, and write about their lives. They shared insights about struggling to deal with mental illness, life in and out of emergency shelters, childhood memories, trying to connect (or reconnect) with their families, and overcoming addiction. Almost everyone spoke about wanting to tell their stories so that people could better understand them, their lives, and what it’s like to live through struggles like theirs—reminding us that stories are a powerful way to challenge stereotypes and transform perceptions.