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There is a strong relationship between success in education and success in the knowledge economy. However, educational achievements do not translate into commensurate rewards in the labor-market for everyone. Drawing on an idea from Robert Nozick, I propose a model in which individuals acquire expectations about their future social position based on their performance in education. Subsequently, they develop grievances toward the market economy if it fails to meet these expectations, and therefore exhibit a greater preference for wealth redistribution. To explore these dynamics, this study utilizes panel data from the 1970 British Cohort Study, which follows students as they transition into the labor-market and includes comprehensive information about their performance in education. The study tests two hypotheses: (1) individuals whose expectations about labor-market success are not met are more inclined toward left-leaning economic policies, and (2) this effect is even more pronounced among individuals in low-status occupations. The study underscores that the political implications of social mobility depend on the status an individual strives to attain by increasing her skills.