Using a qualitative, multiple case study research approach, the personal stories of eight K-12 educators who retired within the past six years were gathered and analyzed. The goal of the study was to understand how educators struggle, or do not struggle, with the life changing event of bringing closure to a career after spending decades in the classroom. Upon analysis of the data, three key themes were identified: (1) The individuals had control over the timing of their retirement; all participants knew it was the right time to make the transition out of the classroom. (2) Each person is happy with both the choices they made in the retirement process, and with the life they now lead. (3) While the length of time and degree of involvement differed, each person wanted to remain connected to their school and colleagues once the decision was made to retire. The study revealed some of the struggles and joys the individuals experienced during their transition out of the classroom environment. From increased freedom to choose what to do on the spur of the moment, to being able to help elderly parents struggling with health problems, the participants in this study were busy on a day-to-day basis and had established a new balance and flow to their life. [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.]