As a young man, Oland pursued a career in theater, at first working on set design while developing his skills as a dramatic actor. In 1906, he was signed to tour the country with the troupe led by Russian-American actress Alla Nazimova (1879 – 1945). The following year he met and married the playwright and portrait painter Edith Gardener Shearn (1872-1968). Shearn made an ideal partner for Oland. She mastered Swedish, helping him with the translation of Strindberg's works that they jointly published in book form in 1912.