Lee studied at Telok Kurau Primary School, Raffles Institution (where he was a member of the 01 Raffles Scout Group), and Raffles College (now National University of Singapore). He was stopped from going to university by World War II and the 1942-1945 Japanese occupation of Singapore. During the occupation, he ran a successful black market business selling tapioca-based glue called "Stikfas". Because he had taken Chinese and Japanese lessons since 1942, he was able to find work transcribing Allied wire reports for the Japanese, as well as being the English language editor on the Japanese "Hodobu" (報道部 – an information or propaganda department) from 1943 to 1944.