Randy Hodson’s research on workplace inequalities and dignity at work asks vital questions about the capacity of employment to provide the resources needed to support a decent life. A decent life involves not merely the capacity to meet basic needs but also the possibility of investing in upward mobility, for example by pursuing a college degree. Rising employment inequalities and slow-growing wages in the United States over the past several decades have challenged the capacity of ordinary workers to make these investments. Yet worries about college affordability are more likely to be expressed as a concern over the price of schooling than as a concern over the returns to work. In this chapter, I conduct an historical analysis of trends in the costs of college compared to trends in wages from the 1970s to the 2000s in order to evaluate how stagnating wages affected the possibilities for paying for college, using several different data sources on college costs and wages. I focus on the question of how much money a student worker could earn toward the costs of college. I show that over time student work became a significantly less lucrative undertaking and would have covered less of the costs of college over time even if college costs had remained stable. I conclude that we must pay attention to how the jobs crisis affects a range of institutions and growing stratification in opportunity in America. As Randy Hodson argued in his voluminous research, dignity at work has far-reaching consequences for the chances of a decent life.