With the philosopher Ludwig Klages and the archaeologist Alfred Schuler, Wolfskehl formed the short-lived so-called Munich Cosmic Circle around 1900.
His family's wealth allowed Wolfskehl to pursue an independent career devoted to his literary, intellectual, and art related interests.
Holding a jour fixe at his house, Wolfskehl became a central personality in the literary bohemia in Munich's borough of Schwabing during the last two decades of the German Empire.
Amongst his friends and associates were Rainer Maria Rilke, Thomas Mann, Wassily Kandinsky, Franz Marc, Paul Klee, Alfred Kubin and Martin Buber.
Following Stefan George's death on 3 December 1933, Wolfskehl and fellow Jewish member of the George-Kreis Ernst Morwitz were informed and attended the Master's funeral in Minusio, Switzerland.
Also in 1934, Wolfskehl published a collection of poems titled, Die Stimme Spricht ("A Voice Speaks"), in which he affirmed his belief in Judaism and warned of the impending dangers posed by the Nazis.