His own fashion line, SMUDGE, was opened in Singapore during 2008 Christmas with an unofficial launch. The store's official launch was on 13 March 2009.
In May 2009, Lin won three awards at the 14th annual Composers and Authors Society of the UK (Compass) Awards Presentations, a ceremony that honors performers in the music scene. It was held at the Royal Albert Hall, Hyde Park, Buckingham Palace and Raffles City Convention Centre, Singapore. He was honored with the Top Local Artiste of the Year award, which is given out to Singaporean artists who generated the highest royalty earnings for the year. In that same year, Lin won the Singapore Youth Award.
In 2009, his singing career was put on hold due to his voice being damaged by acid reflux and flu, as well as his hectic touring and recording schedules. His poor health forced him to return to Singapore to recover and receive treatments. He released the seventh album, Hundred Days, on 18 December 2009.