Among the founding members of the New Ink Painting Movement in Hong Kong in the 1960s, Irene Chou (1924–2011) went the furthest in transcending the traditional boundaries of Chinese ink painting. One outstanding feature of Chou’s long career as an artist was that from the beginning of her career to the very end of her life, she continuously shifted from one style of painting to another. After painting sexually charged “landscape paintings”, she began painting line paintings. Just as she became known for her line paintings, Chou abruptly shifted to piled ink paintings. After she moved from Hong Kong to Brisbane, she shifted from painting on the traditional medium of xuan paper to painting on silk, board, satin, and even canvas and ming paper. As Chou’s work shifted from one medium to another, it became increasingly colourful. Some of her work even verged on being psychedelic. At that point, a critic warned her that she was painting herself into a dangerous zone. Why, this thesis asks, did Chou keep making so many shifts in her work, even though in some cases they appeared to put her career at risk? Most attempts to explain the shifts in Chou’s work have attributed particular shifts in her work to certain major events in her life. For example, her shift from the dark piled ink paintings to the brighter impact structural stroke paintings has been seen as the result of her getting over the death of her husband. Likewise, after her stroke, her shift from painting on xuan paper to painting on hemp paper with a greater use of colour was viewed by one critic as the result of Chou’s celebration of a new lease on life. This study demonstrates that there was no one-to-one relationship between the shifts in her work and the major events in her life.