Previous research has shown that Canadian municipalities have lower visible minority proportionality rates among elected officials than other levels of government. To understand why, six visible minority city councillors and candidates from Toronto and Vancouver were interviewed. Respondents contributed their personal experiences and perspectives on issues of mirror, symbolic, and substantive representation of visible minorities. They discussed their initial involvement or interest in elite politics, their role models, and their understanding of the term “visible minority.” A broad narrative describes the complexities of political representation in practice and revealed that there were fewer entry points into elite municipal politics for individuals from marginalized groups. These entry points are further obscured by systemic barriers. Barriers were common for both cities despite differences in electoral systems and council structure. This paper recommends reimagining the “visible minority” categorization, and a policy framework that promotes the democratic ideal through institutional evaluations and acclaim for advancements.