In this double episode, we introduce the 2026 Conference Chairs, Associate Professor James York and Professor Jeanette Dennisson. We discuss the integration of ludology and ludic approaches in education, particularly in language teaching, and language technology in medical education. We explore the differences between gamification and ludic teaching, emphasizing the importance of play in learning. Jeanette shares her experiences in medical education, focusing on the use of chatbots for enhancing communication skills among students. We muse over the challenges of measuring student performance and the importance of reflective learning in the educational process. We explore the themes of failure and success in education, particularly in the context of using technology and self-directed learning. We discuss the importance of reflection, iterations, and feedback in the learning process, as well as the challenges posed by techno-stress. The conversation emphasizes the need for collaboration and building a supportive network among educators to navigate these challenges effectively. The chairs also share personal experiences of failure and the lessons learned from them (our JALTCALL 2026 Conference theme), highlighting the significance of sharing these experiences within the educational community.