To challenge conformity and foster explorative and transformative pre-service arts education, students’ reflections and informed choices should be central. Drawing on Hannah Arendt’s concept of professional judgment, this philosophical study explores how such judgment might be cultivated among becoming musicians in the Western classical tradition. We propose cross-instrumental collaborative workshops on musical interpretation as a way to challenge conformity in higher music education from within. These workshops aim to foster reflective, imaginative, and socially engaged musicianship. Challenges and possibilities of implementation are discussed, with forward-looking reflections on how pre-service arts education might resist institutional inertia and embrace change from within.