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Health professionals are expected to routinely assess their weaknesses, set learning goals, and monitor their achievement. Unfortunately, it is well known that these professionals often struggle with effectively integrating external data and self-perceptions. To know how best to intervene, it is critical that the health professionals community understand the cues students and practitioners use to assess their abilities. Here the authors aimed to gain insights into how and why medical students set learning goals, monitor their progress, and demonstrate their learning.In 2012, the authors conducted semistructured interviews with Year 2 students (n = 20), applying an inductive approach to data analysis by iteratively developing, refining, and testing coding structures.Themes were constructed through discussion and consensus: (1) Students were diverse in how they set learning goals, (2) they used a range of approaches to monitor their progress, and (3) they struggled to balance studying for exams with preparation for clinical training. Tensions observed highlight assumptions embedded in medical curricula that can be problematic.Educators often treat medical students as a cohesive whole, thereby creating a mismatch between assessments that are intended to be formative and information students use to monitor their progress. Despite limited exposure to clinical contexts, goal generation and monitoring often stem from a desire to prepare for clinical practice. In grappling with these tensions, it is important to be mindful that students are individualistic in how they balance their commitment to prepare for clinical work and the need to concentrate on exams.