Today’s students need more than just content knowledge to be able to work and excel in the 21st century workforce. Skills in problem solving, communication, collaboration, creativity, and innovation are essential for students to succeed. An increasing body of evidence suggests video games are powerful ways to give students these skills. This chapter includes a description of 21st century skills and provides information on generative gaming based on the generative learning theory, which requires students to generate their own learning based on their experiences in an individualized environment. It concludes with an example of a mathematics-based game development initiative at New Mexico State University that teaches content knowledge and fosters 21st century skills by enabling generative gaming.