Urban planning has evolved as a settler-colonial project and tool of White supremacy that has resulted in the systemic marginalization and exclusion of Black Indigenous and People of Colour communities. From the planning classroom to planning practice, it has become imperative for practitioners, future planners, and scholars to adopt anti-racist agendas and rethink how to facilitate system-wide transformation for Canadian cities. We will discuss our academic research, teaching, and professional practices associated with diversity and cities to interrogate how to bring planning forward and create inclusive and equitable cities. Topics including but not limited to public space, urban health, environmental justice, immigrant settlement and integration, and community engagement will be addressed. We call for a system-wide transformation taking a multi-scalar approach, critically reflecting on components of change at the personal, interpersonal, and institutional levels. A national-level task force for strategic collaboration and a coordinated shift toward the profession’s anti-racist future is recommended.