Following his release from Gormanston, O'Connor took various positions including that of teacher of Irish and theatre director. Thanks to his continuing connection with Corkery, he was introduced to Lennox Robinson, then the secretary for the Carnegie Trust. Robinson was organizing rural libraries and engaged O'Connor as a trainee. O'Connor worked first in Sligo and later under Geoffrey Phibbs in Wicklow.[7]
Through Phibbs, he met and was befriended by George William Russell (Æ), who requested O'Connor to send him material for publication. Russell introduced O'Connor to most of the well-known Irish writers of the day, including W. B. Yeats, F. R. Higgins and Augusta Gregory.[8] In his memoirs, he paid tribute to both Yeats and Russell for the help and encouragement they gave him.
In December 1928, he moved to Dublin to take up the position of librarian at the Pembroke District Library.
In 1935, O'Connor became a member of the board of directors of the Abbey Theatre in Dublin, founded by Yeats and other members of the Irish National Theatre Society.[9] In 1937, he became managing director of the Abbey. Following Yeats's death in 1939, O'Connor's long-standing conflict with other board members came to a head and he left the Abbey later that year.[10]
In 1950, he accepted invitations to teach in the United States, where many of his short stories had been published in The New Yorker and won great acclaim. He spent much of the 1950s in the United States, although it was always his intention to return eventually to Ireland.[11]
