The problem being studied was that although humor provides positive effects on student learning, teaching quality, and effectiveness, there are many difficulties in building a professional identity with the use of humor. The purpose of this qualitative autoethnographic study was to explore how humor could shape a professional's identity and be used effectively within an educational system. This qualitative autoethnographic study sought to explain my experiences with humor from a young age to my professional adulthood life and how these experiences have shaped my professional identity as a teacher and an administrator. I used a combination of theoretical frameworks that assisted in narrowing the core tenets of the study, including dramaturgical theory and humor theory. My own personal writings, experiences, stories, and reflections were the main data sources for this study. Three themes emerged from the dataset: (a) the humor style used in younger years helps build a professional identity, (b) humor can increase comfort level and school culture, (c) too much humor can hinder professional relationships and may not promote strong learning environments and professional relationships. The implications of this study include that when adapting a humor style from younger years that teaching professionals ensure that they use a variety of humor types; however, it is essential for professionals to have a thorough understanding of their audience before injecting humor into an educational environment. [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.]