This workshop presents the application of playfulness and gamification toward empowering political agency among voters and citizens taking political action. Participants will engage with these topics in three stages: theory, context, and prototyping. In the first stage, we will discuss and establish principles of playfulness and gamification, with particular interest in the distinction between these ideas. In the second stage, through tried-and-tested playful activities, participants will experience these principles, develop their own value judgments, and in particular evaluate their relevance to political, media, and digital literacy contexts. Finally, participants will apply these observations to imagine novel implementations of playfulness or gamification in their work. This interactive, stepwise process equips participants with tools to support digital, media, and political literacy initiatives, and provokes consideration on how technical research can have impact.