Young adults with disabilities face multiple challenges in obtaining successful post-school outcomes. In a National Longitudinal Transition Study-2 report, Wagner, Newman, Cameto, Garza, and Levine (2005) found that for former students with disabilities, 70% had engaged in paid employment since leaving high school, though only 40% were employed at the time of interview--clearly unfavorable to the 63% employment rate of their peers without disabilities, and similar data have been reported for former students with disabilities in Kentucky. In this brief article, the authors first briefly discuss what the literature says about predictors of successful post-school transition for young adults with disabilities. Secondly, they analyze their latest KY post-school data to determine the factors most associated with successful post-school outcomes for former students in Kentucky. Finally, they provide evidence-based "Transition Tips" for youth with disabilities, their families, teachers, and school administrators.