A mother of four, Chan is no stranger to family tragedy. Her firstborn daughter died prematurely due to brain damage. Her youngest daughter Sabrina was born with rubella, a hole in her heart and without ears.
"I did ask: 'Why God, why me?'" she says. "Then I realized it's for me to learn what life has given me. You just take it on and the make the best out of it."
It was when she was expecting her second child that Chan made her first steps in the business, starting out as a saleswoman in her parent-in-law's 50-year-old watch firm.
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It was a bold decision to venture into the market for high-end timepieces at a time when luxury retail was still far from a full-fledged concept in Asia.
"I started The Hour Glass in 1979 when I was a new kid on the block, a woman coming from outer space," she says, jokingly.
But Chan turned out to be particularly sensitive to market signals. She observed that a lot of Australians and wealthy spenders from the region were coming to Singapore to shop. Her initial plan was thus to establish the first luxury watch outlet on Orchard Road.
The 1,000-square-meter boutique was the first of its kind in Singapore - carpeted and air-conditioned, and advertised with full-page and full-color commercials. Her then-husband Henry also helped to bring the first Cartier boutique to the region in her store.
The turning point came in 1996 when Chan purchased the company and brand name of Gerald Genta, the renowned Swiss watch designer who created the Royal Oak for Audemars Piguet, as well as watches under his own brand.
The Hour Glass has made its name not only as a watch retailer but also by crafting watches for the super-rich, including members of the Brunei royal family. The most expensive watch ever sold by the boutique, a model from the collection of Patek Philippe, went for a record $7 million, Chan says.