Three challenges are highlighted in this chapter to the realization of the social investment strategy in our twenty-first-century world. The first such challenge—intertemporal politics—lies in the term ‘investment’, a willingness to forego some measure of current consumption in order to realize often uncertain gains in the future that would not occur otherwise, such as better schooling, employment, and wage outcomes for the next generation. Second, the conditions that enabled our post-war predecessors to invest heavily in future-oriented public goods—a sustained period of economic growth and historically exceptional tolerance for high levels of taxation—no longer obtain. Third, the millennial cohorts who will bear the costs of a new, post-industrial, investment strategy are more economically divided than earlier cohorts and face multiple demands raised by issues such as population aging and global warming, among others.