The purpose of this study was to explore the attitudes, values and beliefs of young (30 years of age or younger) Supplemental Security Income (SSI) or Social Security Disability Insurance (SSDI) beneficiaries at or near the completion of postsecondary education regarding self-sustaining employment. The study also sought to identify the challenges that young SSI/DI beneficiaries face in the transition to employment, their knowledge and use of the Ticket to Work (TTW) and other work incentives available through the Social Security Administration (SSA), and their preferred methods of communication with SSA. Young beneficiaries in postsecondary education have the greatest potential to transition to financial and system independence, but only 50% obtain employment at any level, and less than .5% go to work at a level that removes them from SSA support. This qualitative study of 49 young beneficiaries, interviewed in focus groups and individually, utilized grounded theory methods that identified four theoretical categories iv that emerged from the data: education as a pathway, work equals worth, efficacy expectations formed by challenges and strategies, and work incentives as a disincentive to work. The young beneficiaries in this study were optimistic about their futures and were investing in their human capital in order to obtain self-sustaining employment that would give their lives meaning, purpose and fulfillment. Many of the participants had never heard of the TTW or other work incentives, and those that were familiar with them found the work incentive system to be complex and confusing. Experiences with overpayments and reporting problems through SSA resulted in feelings that the work incentive system discouraged return-to-work behavior, especially in low-paying, parttime work that has the benefit of building a paid work history and developing positive efficacy expectations. This study includes recommendations that SSA abolish or significantly simplify the work incentive system, update and market the website to target young people, and develop a peer mentoring network. Recommendations for State Vocational Rehabilitation Agencies (SVRAs) include the development of career plans, the provision of benefits planning, and the incorporation of internships and other work experiences in consumer plans. Recommendations for the Rehabilitation Services Administration (RSA) include lobbying for changes to the work incentive system and providing policy guidance to SVRAs.