Planning is a complex field, in which varied perspectives, politics, and potential actions are constantly negotiated. This is even more true in a changing world, in which climate change, war, inequalities, and injustices persist. Instead of proposing a single, homogenized response to key contemporary challenges, this book keeps apparent the divergent voices of people with varied levels and types of experience within the field of planning. The key themes explored span learning, feeling, creating, and acting: how social learning can and should be approached in planning; how important (dis)comfort can be in planning; what the role of arts and science can and should be in this field; and how closely academic planning research should be engaged in “activism” (and what that can mean). The book serves as an empowering tool for students, practitioners, academics, and lecturers in the field of planning to find distinct voices to engage with these pressing debates and question assumptions. It delves into ongoing conversations that these actors will inevitably be grappling with via an unusual format that allows dissonance to shine through. The book includes in-depth conversations per topic, key take-aways for different audiences, further reading materials, and suggestions for continued conversations and research.