This chapter focuses on Richard Light’s experience of teaching junior secondary students in Singapore as part of a four-day seminar he delivered on Positive Pedagogy for sport coaching to physical education teachers. To demonstrate to the teachers how PPed can be applied in physical education classes he taught three classes with this chapter considering them all but focused on the javelin class taught to a ‘difficult’ class. In it he reflects upon the challenges involved in teaching PPed to classes of 40, fourteen-year old students with whom I had no relationship, no knowledge of their skills or dispositions, and who were not accustomed to being empowered. In this chapter he explains how he adjusted the progression of activities he had planned to meet the challenges facing me as well as the questioning strategy he used and his expectations of their learning. He found this session very challenging but there were enough sections of sustained, engagement, enthusiasm, joy and moments that approached flow to provide satisfaction for him. This experience also reminded him of the challenges facing teachers when implementing innovation such as PPed in physical education.