This chapter focuses on the issue of transferring game experience to reality based on Kolb’s learning cycle (1984). When game experts, that is, game designers, facilitators, teachers, etc., use games for educational purposes, for example, in classrooms or workshops, we emphasize the importance of debriefing as well as facilitation as a whole. However, when we scrutinize Kolb’s cycle, we as facilitators can help participants reach the third cycle, which is abstract conceptualization. The fourth cycle, active experimentation, cannot be done within classrooms or workshops because of limitations of time in addition to the fact that we as facilitators cannot interfere with participants’ real lives. This means that there is no guarantee that participants will apply game experiences to the real world or actively experiment with experiences learned from the games. In other words, the learning cycle may not be accomplished in real life. Therefore, the important question is as follows: How can we, the game experts, motivate participants to actively experiment with their game experiences to ensure effective learning? I will tackle this question and offer some suggestions to connect the third and fourth cycles by providing some concrete examples. In addition, in the post-truth era, active experimentation in the real world has become more complex. I am suggesting two possible solutions to the issue for further discussion.