How well do our education policies prepare America's youth for the labor market? What challenges limit our success, and what opportunities do we have for improvements? Can public policy play a greater role in encouraging more success? In this chapter, I provide a summary of what we know on these issues, incorporating but also complementing many of the perspectives provided by the other [forthcoming volume] authors. In addition, I consider these questions as they apply to the unique characteristics of metropolitan areas in the United States. I consider demand for both middle- and high-skill jobs, where the former are defined as those requiring some postsecondary education or training (broadly defined) beyond a high school diploma but less than a bachelor's degree, and the latter are defined as those requiring a bachelor's or higher. I then review the challenges limiting so many young Americans as they prepare for the labor market, as well as what we know about programs and policies that might improve observed outcomes. Finally, I review the characteristics of U.S. metropolitan areas that exacerbate the challenges we face--especially the uneven distribution of people and jobs within and across those areas.