The purpose of this chapter is to analyze Hölderlin’s emphasis on the importance of aesthetic comportment for reconceiving the relationship between human beings and their surroundings, and for enabling what he calls a “higher enlightenment.” Hölderlin shares the romantic critique of the mechanistic conception of nature and life, and argues that human beings have to achieve a higher connection than the mechanical one between themselves and their surroundings. In order to establish this, the bond between human beings and their environment needs aesthetic representation. Poetry is able to particularize and concretize that which in discursive knowledge remains abstract and removed from life. A necessary feature of a higher enlightenment is, according to Hölderlin, the salutary remembrance that human creations, such as art and society, are not completely autonomous but, in a Shaftesburian fashion, ultimately dependent on nature. As this chapter shows, for Hölderlin, an authentic poem is not a closed autonomous work of art but rather an open unity that remembers its dependence on nature and thus can be said to reflect on its own aesthetic heteronomy.