According to the Straits Times, October 7, 2011, Stirling "came to Malaya in 1907 at the age of 20 and joined the government service. He married the daughter of a prominent Chinese merchant." He published a small book of silhouettes of Singapore 'types' (quite shocking to contemporary eyes) called Shadows on a Malayan Screen in 1926 (available as a free download). As Assistant Protectorate of the Chinese in Singapore from 1921 to 1931, he was an expert on secret societies. He co-authored The Hung Society, or the Society of Heaven and Earth with fellow art enthusiast John Sebastian Marlow Ward, and his collection of secret society memorabilia is now in the collection of Singapore's National Heritage Board.