The Internet is home to unprecedented amounts of learning resources, yet few follow through with aspirations to learn from them. How might we empower learners with skills for self-directed learning? Pixel Art Academy explores this challenge in a video game adventure where participants lead a virtual student through their education at a virtual art school. By learning alongside and coaching a virtual student, players learn and practice self-regulation strategies, empowering them to build their own way to mastering the creation of artwork.