For poetry that is so well known, so canonical, George's early work is surprisingly difficult. Many attempts have been made to explicate the early cycles, sometimes in the manner of a decoding, but the characteristic Georgean combination of extreme formal rigor, compelling semantic condensation and a dense network of allusive or symbolic imagery often makes individual poems strangely limpid yet at the same time highly resistant to simple understanding, let alone paraphrase. Their difficulty, and their subtlety, derives to an extent from George's insistent use of paradox, from the frequent conjunction of assertiveness and doubt, and from the overlaying or interweaving of apparently personal emotion with apersonal poetological reflection such that comprehension is sometimes more intuitive than rational. The paradoxes are integral to the central themes of his early writing — dominance and dependence, ruling and serving, desire and self-denial, the spiritual and the material, isolation and belonging.

For a poet whose reputation is one of self-sufficiency, with an autocratic, even arrogant persona, there is discernable a remarkable degree of underconfidence. When first meeting the artist Melchior Lechter (1865–1937), George pretended to be the editor of his journal Blätter für die Kunst, Carl August Klein, and only revealed his true identity after he was certain that Lechter was an admirer of his work. He tolerated few fellow poets in the circle he gathered around him and was often secretive about his movements. This manifests itself in his writing from the earliest years. George's insecurity as a poet in German led to a crisis in 1889 when he appears to have been uncertain whether to write in French or German (see Curtius 154).He emerged from this crisis partly as a result of a form of linguistic apprenticeship, the translation of Baudelaire's Les fleurs du mal. This was undertaken because of “[die] ursprünglich reine freude am formen” (2: 233), and because it offered him the opportunity to explore and discover German by immersing himself in the formal, technical, rhythmic, and phonetic aspects necessary to render Baudelaire's French in a manner that does not simply imitate or transfer but uses the new form to recreate or renew the content for German. His dictum was “strengstes maass ist zugleich höchste freiheit” (1: 530), but in order to achieve that freedom he needed a fuller understanding of the way in which his own language could be “measured.”