Of the approximately four million individuals with disabilities in the under-20 age category, less than 23 percent can expect to work full-time (US. Bureau of the Census, 2003; StatsRRTC, 2005). It is clear that quality interventions are needed to increase the future viable employment of youth and young adults with disabilities. One such intervention is mentorship programs in which students with disabilities are mentored by experienced mentors with disabilities prior to entering work experiences. Weir (2004), among other authors, called for flexible, individualized support programs that enable students with disabilities to pursue and achieve their full potential in higher education and beyond. The purpose of this article is to describe the milestones and lessons of two independent but related mentorship programs for youth and young adults with disabilities.