This longitudinal study followed the clinical learning journey of 20 medical students over 4 years, from the beginning of their clinical immersion, through one of the three different clinical placement models: block rotation, longitudinal integrated clerkship, or community- and hospital-integrated learning, and then into Year 4 and the intern year postgraduation. This study explored how these different contexts can influence the process of transformative learning. The results identified six well-defined changes to their ways of seeing the world which participants described as insights shaped by their clinical training. These themes were self-awareness, patient centeredness, systems thinking, self-care, clinical skepticism, and understanding diversity. Further analysis explored how changes in worldview can be instrumental, communicative, and emancipatory. This study demonstrates that context matters and that longitudinal models of clinical education may facilitate emancipatory learning.