"Harry" Dickinson was himself a student of the South Shields High School for Boys, from 1925 to 1931. On leaving, he went to Kings College in Newcastle, where he spent the next five years gaining his BA Hons in French (with Latin as a subsidiary subject) in Jun, 1936, and his Diploma in the Theory and Practice of Teaching, and his Board of Education Teacher's Certificate.

His first teaching post was at the Westoe Boys County Secondary School, starting on 17th August, 1936. He left the school temporarily on 14th November, 1940, for War Service, returning to the school on 26th March, 1946. Once back, he stayed only to the end of the following school year then, in September, 1947, he took up a position at the South Shields High School for Boys.