To cultivate a culture of deep learning, a facilitator must create a positive and challenging learning environment that fully engages learners and teams (Smith & Apple, 2007). Well-designed TBL modules offer opportunities for rich discussion and feedback. To fully realize the benefits of this process, learners and teams must feel safe to collaborate and reflect within and between teams despite discomfort and disorientation. How learners choose to embrace challenge is critical to their long-term growth and transformation. Transformative Learning (Mezirow, 1996) offers a systematic approach to embracing challenge and making meaning of one's experience in order to guide future goals and action. In this workshop, we will discuss the art of prompting engagement and improving accountability to self- and team-goals through a structured discussion of regulating discontent that promotes the transformative learning process. Participants will engage in applications to: 1) Identify questions that prompt discovery, examination, and commitment of ideas toward promoting individual accountability. 2) Apply an inventory of the learning environment that builds trust and transparency for collaboration. 3) Develop a structure for teams of learners to discuss their discontent when facing challenge and plan solutions to common barriers.