Recent passage of the Workforce Innovations Opportunities Act (WIOA) shows a recognition that more emphasis must be placed on the critical period around transition. As such, WIOA will focus vocational rehabilitation resources and priorities on those transitioning out of high school (United States Department of Labor). Education pays in a variety of ways, and more education results in higher rates of employment, regardless of disability (Smith, Grigal, & Sulewsi, 2012; Migliore, Butterworth, & Hart, 2009). Unfortunately, the expectation for students with ID to attend college has not been well shared or understood by professionals or families (Sheppard-Jones, Kleinert, Druckmiller, & Kovacavich-Ray, 2015; Thacker & Sheppard-Jones, 2011), resulting in a transition process that is fragmented and inconsistent across systems (Hong, Ivy, Gonzalez, & Ehrensberger, 2007). Having employment can add value to a person’s life. Employment can also provide people with disabilities the opportunity for “demonstrating skills and competencies and for formulating friendships” (Wagner et al., 2005, p. 5–1).