He served his National Service as a commissioned officer and was awarded a Sword of Merit in Officer Cadet School.
He was the first Singaporean to be admitted to Harvard College in 1978, and graduated cum laude in Social Studies in 1982.
When he returned to Singapore after university, he worked at DBS Bank for over two years and then founded his own company in design, corporate communications and branding. The company Wordmaker Design lasted 17 years until it was sold in 2000.
In 1987 he was arrested and detained in Operation Spectrum, and after his release was re-arrested and detained when the ex-detainees issued a statement in 1988 denying their involvement in a Marxist Conspiracy to overthrow the government. He spent a total of thirteen months in detention before he was released in 1989. During his time in detention Amnesty International adopted him as a Prisoner of Conscience.
In 2003 he joined the National University of Singapore (NUS) as the founding director of its Development Office. In his six years at NUS, the university raised $1.5 Billion, including government matching. In 2009 he joined Nanyang Technological University (NTU) as its Chief University Advancement Officer, overseeing the offices of Development, Alumni Affairs, and Corporate Communications. In 2010, NTU received its single-largest gift of $150 million ($386 million with government matching) which made philanthropic history in Singapore for its record quantum. In 2012, he left the service of NTU.
Since 2000 he has served as chairman of The Substation, an independent arts organisation, and as a board member of the Intercultural Theatre Institute (formerly Theatre Training and Research Programme TTRP) founded by Kuo Pao Kun and T Sasitharan.
He is co-author of the book on his great grandfather, Chew Boon Lay, A Family Traces Its History.