Anson Chan has dealt with her share of monikers. She was the Conscience of Hong Kong for defending the city’s core values. She was the Iron Butterfly for the tough leadership that belied her patrician poise. Communist newspapers dismissed her as the Old Lady of Democracy. “The epithet I like best was coined by one of the local newspapers – Chan With the Forty Thousand Dollar Smile,” she recalls. “If you play mahjong, there is a tile which is forty thousand. And the Chinese character for forty thousand is like a grin.”

Today, Chan still has the same winning smile, but she is known mainly as a political gadfly, a staunch supporter of democracy who is never shy about taking the government to task. And while her activism has won her legions of supporters, Hong Kong’s increasingly polarised political climate has taken its toll on her reputation, reducing her to “a voice in the wilderness,” in the words of one (sympathetic) political commentator.

But Chan’s reputation has as much to do with her track record in public service as it does with her political positions. From her entry into the civil service at a time when women weren’t expected to pursue a career, she climbed her way up to the government’s second-highest position, carefully steering the city through its transition from British colony to Chinese Special Administrative Region.

Chan and her twin sister Ninson were born in Shanghai in 1940, the only two girls in a family of six brothers. (They are still close – Chan keeps a mug printed with an old photo of the pair on her desk.) Their father, Fang Shin-hau, was a textile manufacturer, while their mother, Fang Zhaoling, was an aspiring classical Chinese painter. Chan’s paternal grandfather was Fang Zhenwu, a former Kuomintang officer who had helped overthrow the Qing Dynasty in 1911. Though he was considered a hero for fighting the invading Japanese army in the 1930s, he was opposed to KMT strongman Chiang Kai-shek, which led to his assassination in 1941.

The family left for Hong Kong in 1948 as Communist forces were bearing down on Shanghai. They were part of a wave of wealthy, well-connected industrialists who quickly found favour with the colonial government. Though they lived a comfortable life, Chan’s father died unexpectedly in 1950. Her mother left for the UK with Chan’s three older brothers in order pursue her career in painting. While her mother was away, Chan was raised by her “uncles, aunts and maternal grandmother,” who were particularly strict towards her and Ninson. They were rarely allowed out of the house, so they spent much of their time reading.

Their mother’s determination left a deep impression on Chan. “My mother had a great influence on me,” she says. “She was a redoubtable, resilient, resourceful lady. I remember my mother as a very good cook. She made all of our clothes. She just seemed to be good at everything she did. She was a woman in many ways ahead of her time. She had the good fortune of having a mother that saw value in making sure that her two daughters had the best education. In the 1930s it was practically unheard of for a Chinese lady to be educated overseas, but my mother actually met my father when they were both studying at the University of Manchester.”

Chan joined government “purely by chance,” she says. In 1962, after studying English literature at the University of Hong Kong, she had wanted to become a social worker, but when she she saw a job opening in the civil service, she jumped at the chance to earn HK$1,200 a month as an administrative cadet.

“That was a handsome sum of money,” she says. But it was only 75 percent of what her male colleagues earned, with no fringe benefits. Chan was one of only two women accepted to the civil service that year. They were expected to work for “pin money” until they got married, at which point they would presumably quit, have children and become housewives. Chan says that assumption “could not go unchallenged.” Even after she married her university sweetheart, Archibald Chan, she had no intention of abandoning her career.

“Going into a male preserve administrative service, you have to work doubly hard in order to prove yourself,” she says. “I was determined to prove by my performance that I was taking my work very seriously.”

Chan shuffled between government departments, eventually rising in rank to senior administrative officer in 1970. It was around this time that she helped establish the Association of Female Senior Government Officers, which fought for equal pay between men and women. They achieved that goal in the 1980s, though gender-based discrimination in the private sector wasn’t outlawed until 1996.

At a press conference as the Director of Social Welfare – Courtesy Anson Chan’s Office

In 1984, she became Hong Kong’s Director of Social Welfare – an apt position for someone who had once dreamed of being a social worker. Her tenure turned out to be more contentious than she expected. In 1986, the press reported that a six-year-old child, Kwok Ah-nui, had been trapped by her mentally ill mother in the family’s tiny public housing flat. Chan ordered social workers to break into the apartment and take the child into protective custody. That unleashed a storm of critical media coverage. Though she was cleared of any legal or procedural wrongdoing, Chan was branded as heartless and cruel for breaking up a family.

The backlash stung. It took years for Chan to rebuild her relationship with the press. “I thought the press was extremely unfair to me, which gave me a lesson in life, which is that there is nothing that is absolutely fair or unfair – you have to conduct yourself according to your standards of behaviour and not according to what other people demand of you,” she says. “For awhile, I stopped reading newspapers, I had no dealings with the press. [Eventually], I decided I had to come out of my shelter and deal directly with the press.” She decided to smile often and treat reporters with patience. “I feel that the best way to deal with the press is to be as forthright and direct as you can.”

Dealing with the media proved a useful skill as Chan’s fortune continued to rise. In 1987, she became Secretary for Economic Services, and then Chief Secretary in 1993. Chan was both the first woman and the first Chinese person to work as Chief Secretary, who is responsible for drawing up and implementing government policy. It is the government’s second-highest position, and Chan became the public face of Hong Kong’s handover, as she guided the government towards a new future under Chinese sovereignty. Chan held the position for six years – three under Chris Patten, the last British governor, and three under Tung Chee-hwa. She retired in 2001.

Chan was by most accounts an extremely effective leader, but like many powerful women, she had to deal with the perception that she was overly aggressive. She has always taken such criticism in stride. “Not that it bothers me, but I think that some men — not all men — feel that certain attributes that they find attractive in a man are very unattractive and sometimes unacceptable in a woman,” she told feminist journal On The Issues in 1995. “Qualities like being aggressive and ambitious seem to be negative qualities in a woman. However, I’m not being paid to win a popularity contest. I don’t flinch from making difficult decisions.”

Interestingly, the same journal compared Chan with Hillary Clinton, quoting historian Geraldine Forbes as saying “Hillary lacks the legitimate power that Chan possesses.” (At the time, Clinton was reeling from a failed attempt to introduce universal health care to the United States.) Unlike Clinton, however, Chan says she has never aspired to high political office. “I never wanted to be Chief Executive,” she says. The nitty gritty of the Chief Secretary’s work struck her as more important than being a figurehead.

Looking back, Chan says Hong Kong is a much better place for women today than it was when she was forging her path. But it still struggles with gender disparity, even in the civil service. Only a third of high-ranking civil servants are women, and women account for just 27 percent of the government’s advisory bodies. Women are even less represented on the boards of Hong Kong’s private companies.

Women Workers’ Association coordinator Wu Mei-lin says the kind of attitude Chan encountered in 1962 is still pervasive today. “The mindset is deep that if women have children or family burdens they cannot focus on their work,” she told the South China Morning Post earlier this month. Hong Kong’s high cost of living and lack of affordable child care keeps many women out of the workforce; just 10 percent of families here can afford a domestic helper.

Chan has been vocal on some of these issues; two years ago, she blasted the government’s Women’s Commission for failing to accomplish much since it was founded in 2011. But she has always taken a conservative approach to women’s rights. “I never regard myself as a feminist,” she told Time Out magazine in 2015. “I just regard myself as fighting for my just due.” She is most passionate when she is talking about Hong Kong’s democracy and civil society – and it’s something she continues to do vociferously, even as the attacks from her opponents grow ever louder and more vicious.

“I wasn’t born in this city, but I have benefitted from the education, from the exposure to values of basic human dignity and human freedom,” she says. “I want to preserve what it is, which is what China promised the people of Hong Kong to the acclaim of the international community. In my view, we deserve the government we get if we don’t have the courage to stand up for what we hold dear.”

It’s at times like these that Chan says she thinks about her mother, who died in 2006 after a long and successful career. “My mother went through some very difficult times,” she says. “But nothing ever made her give up. She used to write me calligraphy that said you should stand back, look at things and never allow anything to thwart you. You just soldier on.”

Anson Chan was profiled in Those Who Inspired Hong Kong