This applied dissertation was designed to examine whether or not students with disabilities (SWD) were prepared for the transition from high school to employment or to postsecondary education. Numerous reports had shown that SWD were being challenged with making the transition from postsecondary school to the next stage of their life, whether that is a full time job or attending college. To this end, the primary focus of this was to examine particular areas that were most beneficial for these students. If these areas were identified they could be used to better prepare SWD for their transition into the real world. The researcher conducted a case study with a mixed method approach. The participants consisted of 10 SWDs who were randomly selected and had graduated from high school in the School Years 2003 and 2014 with either regular diplomas or special education diplomas. These students completed a survey via mail followed by a telephone interview. The data gathered was analyzed and was used to address the research questions. An analysis of the data showed that overall the students had a positive experience in their education while in high school. They felt their teachers did an adequate job of preparing them for life after high school. However, the students felt that there were 2 areas that needed to be changed in the future. These areas were: (a) the need to be involved when they are planning for their future after high school, and (b) more real world experiences needed to be taught in class such as dealing with mock job interviews, filling out job applications and other post secondary items. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]