 Aitken managed Bennett's successful campaign for a place on Chatham town council.When Bennett left the law firm, Aitken moved to Saint John, New Brunswick, where he again sold life insurance before moving to Calgary where he helped to run Bennett's campaign for a seat in the legislative assembly of the North-West Territories in the 1898 general election.After an unsuccessful attempt to establish a meat business, Aitken returned to Saint John and to selling insurance.