After leaving Oberlin, Swing worked briefly in a barber shop. His first foray into journalism came at age 19, in 1906 with the "Cleveland Press". This was followed by stints at "The Richmond (Indiana) Evening News", the "Indianapolis Star" and "The Cincinnati Times-Star". Determined to prove himself after what he saw as his early failure, he worked to the point of exhaustion. His career was meteoric. At age 23 he became managing editor of the "Indianapolis Sun." Then he was named London bureau chief for the "Philadelphia Public Ledger". He also wrote for the journal "The Nation" during this time.