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This longitudinal narrative inquiry explores how an underprivileged secondary student in Hong Kong invested in private tutoring to overcome social and educational inequalities. Using Norton’s concept of investment, the study examines the complex interplay between learner identities and a high-stakes assessment environment. Data collection included reflective writing, multiple rounds of interviews, and classroom observations. The findings reveal how the student leveraged tutoring to progress academically, expand her social network, and improve her self-esteem. The study highlights the potential of private tutoring in addressing educational disparities while acknowledging its limited accessibility for disadvantaged students. Policy implications include government subsidies for tutoring and support for fee-free supplementary services. Further research on tutoring experiences of disadvantaged students in affluent societies is recommended.