This case study examines a workshop utilizing visual art-based methodologies to support second-year medical students in their transition into clerkship. Through a series of three activities, art educators and medical faculty collaborated to facilitate student reflection on this pivotal academic transition. The workshop created a reflective space that enabled students to articulate their emotions, recognize shared challenges, and develop a sense of community and belonging. Additionally, the workshop provided insights into the importance of teamwork, the value of diverse perspectives, and the value of the visual arts. This interdisciplinary approach highlights the potential of integrating art-based education within medical training to address transitional challenges and enhance student experiences. The impact on students and the lessons learned through this implementation are discussed in detail.