Jacobson attended Boys' High School in Kimberley and graduated at the age of 16. He went on to the University of Witwatersrand in Johannesburg, where he graduated at the top of his class with a bachelor's degree in English Literature. Following his graduation in 1948, he worked as a laborer in an Israeli kibbutz for about a year. Then he got a job as a teacher at a Jewish school in London. In less than a year, he was asked to leave, according to his autobiography, because he did not know enough about Orthodox Judaism.