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Sustainable development is often taken to mean development that improves human well being subject to natural constraints over time, but in practice quantifying sustainability outcomes is often difficult. In this dissertation I seek to better elucidate the relationship between sustainable development and its natural constraints by focusing on human capital outcomes, which I argue provide one of our best summary statistics for “human well being” in general. Whether the constraints are imposed by natural systems (Chapters 2 and 3) or human ones (Chapter 4) I find strong evidence to suggest that attempts to pursue sustainable economic development must deal with nuanced and often conflicting interactions between the human capital invesment and accumulation process and its fundamental constraints.