In a youth-oriented culture, individuals in midlife who are facing 30-40 years of life after full-time employment are redefining retirement. As people are healthier, living longer, and desire to contribute to society in meaningful ways, college and university administrators have the opportunity to create innovative programs that align with missions and assist individuals in mid to later life with the next phase of their lives. Such programs have the potential to enrich educational experiences, promote dialogue, construct collaborative learning, build a better understanding between generational differences, and help with the changing landscape and demographics of our society. This case study explored Stanford Distinguished Careers Institute to gain insights from college and university administrators on how to design a program for mid to later life adults and to learn from participants as to their experiences in the program. Transformational or transformative learning theory was the theoretical framework used for this study. My findings indicate transformational learning is likely happening in different ways in the thematic findings of community, self-reflection, exploration, program evolution, and the intergenerational setting. Transformational learning, however, is not necessarily as evident in all areas. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]