The collapse of the global economy in 2008 had a devastating impact on manufacturing and other sectors across Canada. Displaced workers were unprepared for the demands of the new knowledge-based economy and found that they required retraining to secure employment in modern, highly technical workplaces. In Ontario, the introduction of the Second Career (SC) program provided opportunities for laid-off workers to attend college for retraining. Using qualitative methods, this study explores the experience of adult students participating in a government-sponsored retraining program. The findings suggest that adult learners who return to school encounter many challenges, including the need to balance school-life responsibilities, the dynamics of generationally diverse classrooms, significant financial pressures, adaptation to a new postsecondary environment, the need to relearn how to learn, the need for academic upgrading, and bureaucratic processes. In addition, the data reveal significant impacts on SC students, including renewed confidence and hope, a determination not to fail, new skill development, preparation for and connection to employment, establishment of powerful relationships with instructors, and development of a supportive community of peer learners. The data revealed in this study provide important recommendations to key stakeholders with respect to the importance of educational planners creating conditions for success when planning and implementing a school-to-work transition program for displaced workers.