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As commonly understood the term “anarchy” sends shivers down the spines of many. Usually, disorder, danger, and chaos are what comes to mind when one hears “anarchy.” Despite this novice view of a society without leaders, what if anarchy were the most freeing form of coexistence? This article will begin with a more precise definition of freedom by explaining philosopher Immanuel Kant’s views concerning the refined and matured concept of dutiful freedom, or autonomy. Next, there will be demonstrations concerning why anarchy is most compatible with people’s autonomy, through the lens of philosopher Robert Paul Wolff. After that, this piece will draw from Robert Nozick’s philosophy as to why a stateless, or minimalist economy best fits with autonomy, and hence, anarchy as well. Lastly, this essay will close with why anarchy and statelessness rests on autonomy, and how with that understanding in mind, people can at least rethink this political outlook more open-mindedly.