Today, The Hour Glass has mushroomed into a regional network of 24 luxury boutiques in major shopping belts in Singapore, Malaysia, Hong Kong, Indonesia, Australia and Thailand, and has a market capitalization of $318 million.

But even established players are not immune from challenges in the retail world, which can include surging rents, demanding customers and shrinking profits.

Chan recognizes the demands of sustaining a business. When you open a new shop, you cannot assume that you will necessarily get customers, she warns.

Chinese market offers better times for the rich

Women at the top

"The competition is there, the cost is there and the market is so differentiated," she explains.

Adapting to market changes is the key for Chan. In recent years, seeing the rise of China's new wealthy, The Hour Glass launched limited-edition watches targeting a new breed of heirloom collectors.

"You have to constantly come up with different marketing strategies," she says.

Sipping a cup of black coffee in a caf, Chan looks back over her long and distinguished career in which she holds many "firsts". She is the first female president of the Association of Southeast Asian Nations Business Forum and of the Singapore Retailers Association.

She is also the first and only female board member in the Commonwealth Business Council. In 2009, she became the first winner of the Woman Entrepreneur of the Year Award organized by Enterprise Asia.

However, Chan used to fear and reject some labels inevitably bestowed on her - being a powerful woman or a "supermom" - which often have negative connotations in traditional societies in Asia.

"When a man is successful, people say he is dynamic and brilliant. If a woman is successful, people will say she's a bitch, a dragon lady, a steel woman and she's overpowering," she says.

But times are changing. "It's a woman's age," she says, citing the examples of the International Monetary Fund and US Federal Reserve which both have female leaders. "Today, we need not be a man," she says. "In fact, I've never been like a man. I've always throughout my career been a mother first - although I delegated."