This qualitative study examined the narrative of community college educators during their journey to embrace a playful teaching practice. Data collection included the narratives produced within a Community of Practice, focus groups with both students and educators, and document analysis. Data analysis revealed six themes. The first theme, origins of play, demonstrated how teachers' playful journey began. The second theme, motivations to become playful, discusses faculty's desire to use play as everyday resistance against traditional pedagogy. The third theme, playful characteristics, revealed the attributes playful educators embedded such as adaptability, organization, joy, and self-acceptance. The fourth theme, the purpose of play, presented four intentions behind playful teaching practices: promoting knowledge assimilation and creation, community building, personal development, and socio-emotional learning. The fifth theme, the context of play, discusses three challenges playful teachers confront and the solutions they created: pushing against stereotypes through transparent communication; negotiating restrictive course structure through finding one's own playful style; and navigating unexpected outcomes through flexibility and failing forward. The sixth theme, benefits of play, revealed that students who engage in playful activities achieve meaningful learning, increased confidence, sense of belonging, and strengthened intrinsic motivation. Outcomes for educators include strengthening their agency, enriching their professional identity within academia, community building, and self-actualization. Conclusions establish the value of play among adults in the postsecondary setting. Recommendations for practice encompass cultivating playful collaborations across disciplines, campuses, and continents; strengthening everyday acts of playful resistance beyond the classroom; and educational leadership embodying a playful outlook. Future research includes investigating cultural realities of play, the longitudinal impact of play on nontraditional transfer students, and integrating play within teacher preparation programs. [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.]