After teaching for a year at Episcopal High School in Alexandria, in 1922, Dabney went to work in Richmond, Virginia as a journalist at "The Richmond News Leader", which was then edited by Douglas S. Freeman. During this period he was also Virginia correspondent for the "Baltimore Evening Sun", where he came to the attention of H.L. Mencken. In 1928, he left "The News Leader" for the "Richmond Times-Dispatch", where he became Chief Editorial Writer in 1934, and editor in 1936. During his time with the "Richmond Times-Dispatch" Dabney also served as the Upper South correspondent for the "New York Times".