The purpose of this qualitative research study was to determine how Baby Boomers make meaning out of disorientating dilemmas and challenges as they enroll in community college for career training. The dilemmas include: retirement, layoffs, shrinking job market, returning to school, and dwindling retirement accounts. Understanding Baby Boomers' processing of this new event can help colleges provide tailored course work, support services, and social networks. Through the voices of ten participants and the guiding framework of Mezirow's transformational theory as well as theories of student engagement and validation, the following themes emerged: (1) Economic conditions influenced Baby Boomers to attend community college and they pursue new careers based on passion and purpose. (2) The community college provides a welcoming feeling of inclusion for the Boomer age student through its culture and through support of the faculty; however, rising expectations of Boomers were expressed. (3) Boomers form social networks with fellow adult students that support and validate them as students. (4) Transformation learning in Boomers is evident in their changed attitude in the classroom. Their process of making meaning out of their dilemmas aligns in part to 10 steps of Mezirow's theory. Suggestions for practice are meant to strengthen existing programs and create new practices to serve this cohort. Community colleges are in a position to connect with Boomers in a meaningful way by being the primary vehicle to unleash the social capital and talent that our communities and employers need (Zeiss, 2006). [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.]