Tripp's ambition was to become an artist, but family disapproval led to him joining the civil staff at Scotland Yard as a clerk in the Commissioner's Office on 22 December 1902.
In 1938 he published Road Traffic and Its Control, which remained the only full-length study of the subject until after his death.
In September 1942, Tripp published a second book, Town Planning and Road Traffic, which looked ahead to postwar reconstruction.
In 1942, the Royal Academy invited him to become a member of its Planning Committee established to set up a scheme for London's architectural reconstruction after the war.
He had a large number of articles published in the yachting press in both Britain and the United States, and also wrote four books on the subject:[9] In 1910 he married Abigail Powell, a Dubliner.