Purpose <p>Self-regulated learning (SRL), as defined by Zimmerman, is a cyclical process of forethought, performance, and self-reflection through which individuals take ownership of their learning. While surgical educators have identified behavioral ways to foster SRL, residents’ motivations to regulate learning and attitudes toward self-evaluation remain less understood. This study explores these underlying drivers of SRL to better understand how residents sustain their learning and assess their development over time.</p> Methods <p>We recruited senior-level residents across multiple surgical specialties at a single academic medical center for a qualitative study using semi-structured interviews. Directed content analysis was applied to identify themes related to motivation and self-evaluation.</p> Results <p>Fourteen residents participated, representing six surgical specialties. Motivations clustered into two major themes: professional identity formation (responsibility to patients, pursuit of intraoperative autonomy, anticipation of independent practice) and personal values (personal standards of competence and intellectual curiosity). Although these factors sustained engagement in SRL, residents reported difficulty evaluating their progress due to limited peer comparison and varied perception on usefulness of faculty feedback. Hence, many developed personal benchmarks to evaluate growth over time.</p> Discussion <p>Surgical residents’ motivation to learn is driven by both personal values and professional identity formation. However, self-evaluation is perceived as challenging due to limited opportunities for peer comparison and varying impact of faculty feedback. Programs may leverage these insights to design learning environments that not only foster autonomy and competence but also provide clearer frameworks for residents to monitor and evaluate their growth over time.</p>