Engaging young learners in exploring complexity and finding opportunities to make systems better requires perspective taking and empathy. Role playing can be a powerful approach to support learners in taking others’ perspectives when exploring the roles, ideas, and feelings of different characters in a system. Here we offer a few thoughts on how to leverage children’s natural desire to play and how to employ different thinking routines to foster perspective taking and empathy. This tool is intended as a starting point and does not need to be followed step by step or happen all at once.