For many students, the transition from high school to adult independent life is one of the most exciting times in their lives. However, that same transition can be daunting, particularly for students with disabilities. Studies have shown the majority of high school students--including an increasing number of students with disabilities--indicate they want to attend a college, university, or other postsecondary education institute (ACT, 2014; Conner,2012; Engle, 2007; Schneider, Broda, Judy, & Burkander, 2014). In fact, the National Longitudinal Transition Study-2 (NLTS-2) found that 60% of young adults with disabilities were reported to have continued on to postsecondary education within 8 years of leaving high school (Newman et al., 2011). Unfortunately, the same report showed that only 41% of students with disabilities who enrolled in a 2-year college and only 34% enrolled in a 4-year program completed their studies (Newman et al., 2011). To prepare students to successfully transition into adult roles, schools need to address gaps in both academic and nonacademic skills. This article provides a description of one solution, the Triangulated Gap Analysis Tool (TGAP), which is designed to assist educators, students, and IEP teams to identify and create annual goals that address the gap in skills, including nonacademic skills, needed to prepare students for postsecondary education, training, employment, and independent living. The TGAP uses five steps to identify and address gaps in a student's skills: identify and record the postsecondary goal, triangulate the postsecondary goal with the academic content and industry standards, determine the gap, identify the steps needed to close the gap, and develop an annual goal and instructional targets to address the gap.