Chakmakjian began his career as a teacher and taught in Gesaria (Kayseri today) and in Giresun. He taught in Beirut in the early years of the 20th century, during the time of one of the early Ottoman massacres of Armenians. Rather than return to his birthplace of Adana, he decided to take a ship to France. He subsequently moved to Stamford, Connecticut and eventually settled in Boston, Massachusetts, where he studied at Harvard University from fall 1905 to spring 1908, then entered Harvard again in February 1912, obtaining an A.B. degree in June 1913 (as a member of the class of 1909). Chakmakjian also served as the editor of the Hairenik newspaper from 1909 to 1911.