It is a common but not unrealistic stereotype of Asian students that educational success is a matter of personal identity and status. As such, achieving distinctions in as many subjects as possible (the popular target of becoming a 'straight A' student) is usually a non-negotiable objective nurtured by both parents and educators. However, unfortunately, such an obsessive pursuit of academic excellence produces both laudable outcomes (e.g., the tendency of Asian students to outperform their counterparts) and dangerous ones (e.g., worrying rates of mental health problems). This theoretical paper hopes to apply the concept of anti-fragility developed by Nassim Nicholas Taleb, one of its methods known as the Barbell Strategy, towards student learning in the hope of a) maintaining a trajectory of academic excellence while b) avoiding the psychological pressures which usually accompany Asian students.