In Nietzsche's early and late writings, he appears as an antimodern, antiliberal political revolutionary, championing the world-transformative characters of (first) Richard Wagner and (later) Zarathustra. By contrast, in the writings of his “middle period,” Nietzsche struck up a rapprochement with the modern world, and developed the ideal of a “free spirit.” Among those writings, The Wanderer and His Shadow sheds the most revealing light on the free spirit ideal. It shows that, even as Nietzsche sought to avoid some of the hazards associated with his more revolutionary writings, he continued to advocate a sharply critical engagement with political and cultural life. And it reveals what Nietzsche understood to be most challenging or problematic about the free spirit ideal—and, thereby, what later moved him away from it.