Stephens was working as a solicitor's clerk and educating himself when he met the Irish poet AE (George William Russell), who encouraged him and helped him publish Insurrections, his first book of poetry, in 1909. His first novel, The Charwoman's Daughter, appeared in 1911 in The Irish Review, which he had helped found that year. It was his next book, The Crock of Gold (1912), with its rich Celtic theme, that established his fame. Like many of his contemporaries, Stephens was greatly affected by the Easter Rising (1916), a rebellion of Irish republicans against the British, and his book The Insurrection in Dublin (1916) remains a classic account.

Stephens' astringent use of irony suggests affinities with his friend James Joyce. He wrote The Demi-Gods (1914) in this vein, but Deirdre (1923) was constructed in a more formal, rhythmic prose. Short stories and lyric poems constitute the remainder of his work. Stephens was active in the Irish nationalist movement, but by 1940 he was living in London, where he made frequent radio broadcasts until his death in 1950.