A focus of human-computer interaction work and a central principle of user experience is that design should avoid discomfort and aim to craft positive experiences for individuals. However, for contexts in which an uncomfortable reaction is intended, instrumental, or indeed inevitable, we recognize that it is inappropriate to design for a positive or "feel good" experience. Herein we describe an investigation into the use of interactive technologies to support transformative learning, a process through which individuals engage with feelings of discomfort. The project is grounded by work with graduate students enrolled in a course that employed decolonizing pedagogies. Throughout the course students responded to uncomfortable, problematic scenarios through interactive tools. We present our analysis of students' learning experiences, their interactions with technologies and their reflections on the effectiveness of these engagements in terms of supporting opportunities for critical reflection, a crucial stage of the transformative learning process.