Sydney’s professional life began with secondary school teaching, a vocation that allowed him the opportunity to work in Europe and the United Kingdom as a young man. Sydney’s career as a teacher, however, was very short-lived. After only a year abroad, he packed his bags and returned home to live with his parents in 1974, so that he could pursue painting as a full-time career. In the five years following this monumental decision, Sydney would go on to produce some of the most profound works of his lifetime.
In 1975, Sydney held his first major solo exhibition at Auckland’s Peter Webb galleries. Sydney’s paintings of the mid- to late 1970s famously depicted scenes from the immediate environment that surrounded him in Otago. At this time in his career, Sydney would first draw his subject matter en plein air and then carefully consider the imagery he would depict, before executing it as a fully resolved painting—a process that could take as long as three years to complete.