Education, its history, and its current state are discussed to better understand how we can prepare individuals to live lives of greater freedom in ways similar to that found in hunter-gather societies. By looking at how humans learned throughout much of history, we can find ways of education and important concepts to be imparted that give a glimpse into what educating individuals to be free rather than to be workers can be like. The particular history of education in America and the successful attempts to dominate the freedoms of individuals from marginalized groups are also explored to understand practices that have worked against the goal of freedom including segregation, White flight, redlining, exclusionary practices based on gender identity, and policies such as No Child Left Behind. The ways in which reform based on ideology rather than solutions that have been empirically proven to benefit students is also discussed. Finally we look to the benefits of allowing children the chance to freely explore, create, and interact with the world as well as the benefits that arise from teaching them empathy, tolerance, and self-regulation without humiliating them in the process.