Shifting Gears was launched in 2007 by the Joyce Foundation, a Chicago-based organization focused on improving the quality of life of citizens residing in the Great Lakes region of the United States. The primary goal of Shifting Gears is to increase the number of low-skilled, low-income Midwestern adults who obtain college-level occupational credentials that have value in the labor market. This article presents the goals of the Shifting Gears initiative and the policy initiatives adopted by Illinois and Wisconsin. Drawing from research supported by each state, this article presents goals, strategic approaches, and lessons for practitioners who have responsibility for leading other regional workforce initiatives in the United States. (Contains 1 figure.)