As mentioned above, Probyn was an outstanding scholar. He began his career by teaching in High School in Jamaica, and then went onto to further education. He served in the Jamaica Foreign Service, then the Ministry of Labour where he attained Office of Permanent Secretary, Ministry of Labour, Jamaica. From June 1978, he also served as a Justice of the Peace in Jamaica. In August 1986, he was awarded the Order of Distinction, Commander (CD) His final post prior to retirement was as Chief Liaison Officer, Regional Labour Board, stationed in Washington.