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The Chinese Mathematical Olympiad has served as a key pathway for mathematical talent development. However, previous research has primarily relied on quantitative methods, with limited attention to the developmental process from competition to career. This study adopts a qualitative design to examine motivational transitions and differentiation among 20 former Olympians at three key decision points: Olympiad participation, academic major selection, and career decision-making. Drawing on self-determination theory, interview data were coded into six types of motivational regulation and categorized into cross-stage trajectories. The study draws three key findings: (1) motivational regulation is dynamic and stage-specific; (2) regulatory styles are shaped by both personal and contextual factors; and (3) four typical trajectories emerged-upward, downward, stable, and U-shaped.