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Most postsecondary students have to deal with academic disappointments at some point in time, with many of them succumbing to their anxieties and failing to learn from these lived experiences. Our study aimed to understand why and how disappointments unfolded in a sample of 20 undergraduate students, using a design whereby interview text was concurrently analyzed across the continuum of learned resourcefulness measured using Rosenbaum’s Self-Control Schedule in conjunction with an inductive, data-driven coding and theme-generation perspective. Reasons for attending university, attributional style, coping and learning, and perceptions of others markedly differed for high- and low- resourcefulness scorers. Whereas high-resourceful scorers used academic disappointments as a motivator to engage in more effort and problem-solving strategies, low scorers ruminated and tried to forget about them. Suggestions are provided on ways to effectively help students become more resourceful and in control of their studies.