My daughter (10) has been swimming year round for two years now. Maybe your son would like it more if he knew that he would be recognized even if he doesn't win. Two things my daughter loves for motivation are the "personal best" ribbons the summer teams gives out, and the dollar store party prizes/oriental trading co. trinkets the winter swim coaches gave to kids who attended a certain percentage of practices. They enjoy the recognition for all their hard work. Some weeks i was just an air head candy, but the kids love it.