In 1959 Jackson enrolled to the University of Western Ontario where he started training in rowing. In 1963 he received a Bachelor of Arts degree and entered a graduate school at the University of Toronto, but shortly transferred to the University of British Columbia aiming to qualify for the 1964 Olympics. He did qualify, but his partner, Donald Pretty, had to be replaced by George Hungerford. Jackson and Hungerford first competed together at the Olympics, yet they won the gold medal.