Although "the compilation of lists of best practices accelerated", significant resources have been allocated, and federal mandates requiring transition special education services for students with disabilities have been in place now for over three decades, post school outcomes for students with disabilities have still not improved significantly (Test, et al, 2006, p. 35). This qualitative narrative inquiry study uses Giddens (1984) structuration theory as a guiding framework to explore how four pioneer transition coordinators experience and make sense of their work endeavors in this field to support student success in the northeastern region of the United States. It takes place during a period of time in which there is a newly increased focus on the educational goal to improve post-school outcomes for students with disabilities in this country. Results were analyzed using an inductive coding method which provided findings of five themes: Creative Collaborations, Ongoing Assessment, Stakeholders don't know what they don't know, Providing Meaningful PD, and Bringing the real world into the school world. Results and findings provide rich detail and useful insights regarding what works, lessons learned, and ongoing challenges for consideration by invested transition special education stakeholders. While this study contributes to a better understanding of this significant problem of practice facing the field of transition special education and this nation today, additional research is needed. Findings also support a recommendation for engaging in a multi-disciplinary approach for future research endeavors, with suggestions shared from fields including psychology, organizational learning, and organizational leadership. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]