Creative Liberty explores the mysteries that emerge at the intersection of online art education, the animation industry, and aspiration in the context of insecurity. Principally, this dissertation addresses three key paradoxes about contemporary animation education and the students who eagerly choose to pursue unregulated self-organized online learning instead of a more traditional education at an accredited art school. Organized into a three-act structure that mimics the storytelling conventions of feature animation, I ask: why might artists willfully pursue educational insecurity; and how does their awareness of that insecurity, both real and mythological, inform their choices in pursuit of career? In the first paradox, I examine why might animation have such an uncertain career pathway despite being an established profession since the early 1900s. In the second paradox, I explore why so many students pursue an insecure education towards an equally insecure career. Finally, I investigate the paradox that the animation industry is a tumultuous, insecure environment that demands high volumes of work for unpredictable pay while also being the same environment many animators staunchly defend as they explain their place in the industry. To address these paradoxes, I followed a cohort of 40 online animation students across various online platforms and classrooms as they engaged in an intensive yearlong study with hopes of joining the animation industry. Along the way, I also interviewed online art instructors, social media artists, and animation industry workers to acquire a clearer understanding of the contemporary online art education landscape and the animation industry more broadly. Overall, this dissertation engages with themes of learning and myth-making across social media platforms to contribute to anthropological understandings of education, precarity, and aspirational labor.