The relationship between academic motivation, support structures, self-esteem, and social mobility was assessed between three culturally distinct Higher Education student cohorts. Two-hundred-and-sixty-seven students took part in the study: 64 American undergraduates; 100 British undergraduates; and 103 Ugandan undergraduates. Using a number of appropriate, validated questionnaires, intergenerational upward social mobility was found to be academically motivating, both intrinsically and extrinsically. Intergenerational upward mobility was significantly positively correlated with academic self-esteem. Cultural differences were found primarily in intrinsic, extrinsic and intergenerational upward mobility scores, with Ugandan students endorsing these variables significantly more than the American students, and American students endorsing them significantly more than the British students. These findings are discussed in relation to the potential impact on student social mobility both here and abroad.