Mr Pickles was educated at St Cuthbert's Boys' School, in Gateshead from 1927 to 1936.

His first teaching post was as an unqualified assistant master at Windmill Hills Secondary Modern School, in Gateshead, from 1st November, 1946 to 30th September, 1947. From here, he went straight to King's College, Durham University, where he gained an ordinary BA in English, History and Spanish in June, 1949. After staying on a year to get his Diploma in Education, he joined the staff of South Shields High School for Boys.

While teaching at the school, he did an external BSc with the University of London, which he gained in 1958. The following year, he left to take up a senior master's post at Ryhope Grammar School