Two studies were conducted to better understand the association between higher education and adult success from the perspective of young adult student loan borrowers five years after graduating. Data for both studies were drawn from the Arizona Pathways to Life Success (APLUS) project. This sample borrowed during a period of changing economic conditions (i.e., 2008-2016). In the first study, I used a convergent parallel mixed methods approach to investigate if borrowing to pay for college alters the higher education social contract and if borrowers would advise others to make the same investment. The qualitative analyses revealed five emergent themes (e.g., Plan ahead; Make decisions based on future outcomes; Look for alternatives to university; Repaying loans; and Social comparison and character statements) and three affective tones (e.g., negative, positive, neutral). Borrowers offered practical financial advice, emphasized being responsible, and focused on career planning and financial security. Key findings suggest the higher education social contract may be changing for first-generation college students. In the second study, I examined the association between meaning in life (MIL), as a subjective marker of a successful adult transition, and satisfaction in multiple domains (e.g., life, job, financial), and investigated if self-concept mediated the association under two conditions: student loan borrowers who had paid off their loans and those who are still in the repayment process. Borrowers who paid off their loans within five years of graduating, reported higher levels of satisfaction, self-concept, and income, but their MIL was similar. Self-concept (i.e., self-esteem and financial self-efficacy) partially mediated the association, although the process operated differently for the two groups, suggesting that student loan debt may be undermining their self-concept. The current research fills a gap in the student loan research literature by examining the long-term repayment experience of borrowers while they simultaneously managed full-time adult roles and responsibilities. Efforts should be made to support borrowers in repaying their loans while also supporting their well-being, career choice, and financial stability. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]