In many areas, the number of people transitioning to retirement is starting to outnumber the number of young people negotiating their way into the labor market. To sustain economic prosperity, these regions need to prolong the working lives of older workers. Maintaining older workers' earning power and employment until and past the traditional retirement age will depend simultaneously on strengthening the quality of jobs, and on supporting older workers' willingness and ability to engage in new career learning so they can keep up with occupational shifts and skill changes. One key challenge policymakers and institutions face in their attempts to address aging-related labor market challenges is the lack of historic examples available to guide decision making. Using a generational transition lens, my dissertation examines the intersections of two global trends--unprecedented population aging and volatile labor markets--at a local level. It focuses on building the case for employability of older workers as a way to inform cross-sectoral policy planning and investments for the benefit of all generations. More specifically, the purpose of my study is to inform policymakers and institutions concerned with the provision of education and skills training for workers later in life as a means of promoting both successful generational transitions and sustainable tax bases. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]