Our country is in the midst of a middle-skills gap where there are more jobs requiring education beyond a high school diploma, and less requiring a four-year-degree. With the changing demographics, our nation is looking at the largest growing population, Mexican immigrants, to gain required credentials to fill those middle-skill jobs. These future workers will come to community and vocational colleges as the primary institutions from which to receive training; therefore, new programs and policies must be developed to meet the demands of the middle skills vocations (Zhang, Guison-Dowdy, Patterson, & Song, 2011), particularly for this new audience. In this project, I sought to step behind the proverbial desk of my job as the Director of Adult Education and Literacy, go beyond the numerical data of workforce needs and demographic changes, and discover, by listening to their own words, how the life experiences of some of my adult Mexican immigrant students have affected their educational aspirations. I aspired toward a phenomenological portraiture-based approach to convey a deeper humanistic understanding of what pursuing further education meant to each participant and their families. From my six interviews, I chose to tell four stories that give voice to the range of aspirations my participants experienced. Central to these stories were themes of learning as finding freedom, learning as communal, learning as family mobility, and learning as perseverance. Understanding the educational aspirations of Mexican immigrant adults through their life events named by these themes moves us beyond the discourse of economic development that characterizes the skills-gap literature, and puts a human face on the meaning invested by these adults in furthering their education. This is important for educators to know when, back behind the desk, we purport to be developing programs to meet “their” needs. The demographic changes in our nation require a view of continuing adult education that takes into account the current context of transnational globalization and hybridity that, in today’s New Destination communities, is our future in the making.