When Chak was eighteen, he traveled to Tokyo, Japan, as an exchange student and performed as a comedic dancer in the streets to earn tuition money. After winning the 1st runner up at Hong Kong ATV's 2005 Mr. Asia Contest, he returned to Japan to finish his schooling. In 2006, he signed an artiste contract with ATV. In 2008, Chak graduated from N-atv's Artiste Training Class. After his contracted with ATV ended in 2009, Chak stayed in South Korea for a year, and earned a black belt in Taekwondo. He returned to Hong Kong in 2010 and joined TVB's 2010 Mr. Hong Kong contest, and holds the record for the first Mr. Hong Kong to win eight different awards.