At the age of thirty-three, Dickey moved to New York, where he was hired to write advertising copy at the prominent McCann-Ericson agency. He stayed in New York for several years before moving to Atlanta agencies.

In 1960, Dickey's first collection, Into the Stone, and Other Poems, was published, and he soon abandoned his lucrative career to devote his life to poetry fulltime. In 1961, he accepted a Guggenheim Fellowship and spent a year in Italy with his family. Two of his most famous volumes of verse, Helmets (1964) and Buckdancer's Choice (1965)Ñfor which he was awarded both the Melville Cane Award and National Book AwardÑwere published soon after. Dickey then taught, lectured, and wrote.

"I came to poetry with no particular qualifications," Dickey stated in Howard Nemerov's Poets on Poetry. "I had begun to suspect, however, that there is a poetÑor a kind of poetÑburied in every human being like Ariel in his tree, and that the people whom we are pleased to call poets are only those who have felt the need and contrived the means to release this spirit from its prison."