This chapter will cover a range of ways in which we can create playful training events, such as lectures, seminars, workshops and other training events. It does so through a lens of giving permission to play to the learner, that is, how the learner feels able to engage fully with a playful experience without standing out as behaving inappropriately. It includes a range of playful approaches that may be used in training events, including details of how these give implicit or explicit permission to play.