 On a trip to Perthshire, Scotland in his late teens, Jolly encountered craggy stone inglenooks that would later be a strong feature in his buildings.After finishing school, he returned to work at his family's firm for several years.In 1908 he moved to Sydney and began work for the firm Wardell and Denning, where he completed a two-year architectural apprenticeship, following which he moved back to Lismore in 1910.