In 2009, former U.S. Labor Secretary Robert Reich observed that automation was displacing people from manufacturing jobs worldwide, and asserted that 4-year college completion, rather than an effort to bring these jobs back to the U.S., offered the best means by which those born into America’s working class could secure economic well-being going forward. Reich’s prediction was in conflict with accounts I’d collected while embedded in a community of non-college-educated oil workers during my master’s thesis fieldwork; among those whose offspring had completed college, almost none of them had been able to maintain or retain a white-collar job years after earning their degrees. Through interviews with 100-plus American born first-generation college graduates of top universities with wide ranging job outcomes, my dissertation offers a comparative analysis of key factors that may moderate one’s ability to gain secure footing in jobs requiring a college degree. I demonstrate that the greatest predictor of such success is not the esteemed cultural capital of Pierre Bourdieu (as depicted here through one’s experience of embeddedness and belonging among upper-middle class peers in college, and through one’s willingness to embrace upper-middle class culture post-college), but the strength of one’s sense of the direction they wanted to go in professionally, and the serendipity of their accuracy about this professional direction being a strong fit for their interests, talents, and non-work life goals. As such, I argue that it is incumbent upon modern universities, to whom students make significant payments in exchange for training that they expect to lead to white-collar jobs, to provide their students with robust advising and experiential opportunities that optimize their ability to identify jobs that would be the most fulfilling for them along a first, or even forever, career path. The first chapter of my dissertation also surveys the career decisions and vocationally-based experience of second class citizenship that the non-college-educated American oil workers referenced above have navigated, and illuminates some preliminary solutions whose adoption and development could simultaneously broaden the middle-income job supply and nurture a more inclusive citizenship experience for this demographic.