With the federal call to action that by 2020 all students will graduate from high school ready for college and a career, schools are focusing on increased academic preparation. For students with disabilities, academic preparation alone may not be enough to ensure readiness for college, career, and life in the 21st century. To be fully prepared, students must gain the nonacademic skills necessary to achieve successful adult outcomes including soft skills, social skills, and functional independent living skills. This article demonstrates the Triangulated Gap Analysis tool (TGAP). The TGAP assists educators, students, and transition planning teams to identify and address nonacademic skill gaps when writing annual IEP goals and objectives. Moreover, using the tool can help identify the skills necessary for student’s to graduate better prepared for college and career and increase the likelihood of a successful transition into adult life.