This freelancing attempt did not start out well, with Benchley selling just one piece to "Vanity Fair" and accumulating countless rejections in two months. When a position as press agent for Broadway producer William A. Brady was offered, Benchley accepted it, against the advice of many of his peers. This experience was a poor one, as Brady was extremely difficult to work for. Benchley resigned to become a publicity director for the federal government's Aircraft Board at the beginning of 1918. His experience there was not much better, and when an opportunity was offered to return to the "Tribune" under new editorial management, Benchley took it.