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First stay in Trieste

Joyce moved to Trieste in March 1905 aged 23. He taught English at the Berlitz school. That June he published the satirical poem "Holy Office". After Nora gave birth to their first child, Giorgio, on 27 July 1905, He convinced Stanislaus to move to Trieste and attained a position for him at the Berlitz school. Stanislaus moved in with Joyce as soon as he arrived that October, although most of his salary went directly to supporting Joyce's family. In February 1906, the Joyce household once more shared an apartment with the Francini Brunis.

During this period Joyce completing 24 chapters of Stephen Hero and all but the final story of Dubliners, but was unable to get Dubliners published. Although the London publisher Grant Richards had a contract with Joyce, the printers were unwilling to print passages they found controversial; English law could not protect them if brought to court for circulating indecent language. Richards and Joyce went back and forth trying to find a solution where the book could avoid legal liability while preserving Joyce's artistic integrity. As they negotiated, Richards began to scrutinise the stories more carefully. He became concerned that the book might damage his publishing house's reputation and eventually backed down from his agreement.

Trieste was Joyce's main residence until 1920. Although he would temporarily stay in Rome, travel to Dublin and emigrating to Zürich during World War I— it became a second Dublin for him and played an important role in his development as a writer. He completed Dubliners, reworked Stephen Hero into A Portrait of the Artist as a Young Man, wrote his only published play Exiles and decided to make Ulysses a full-length novel as he worked through his notes and jottings. He worked out the characters of Leopold and Molly Bloom in Trieste. Many of the novel's details were taken from Joyce's observation of the city and its people, and some of its stylistic innovations appear to have been influenced by Futurism. There are even words of the Triestine dialect in Finnegans Wake. Joyce was introduced to the Greek Orthodox liturgy in Trieste. Under its influence, he rewrote his first short story and would later draw on it in creating the liturgical parodies in Ulysses.