The former Chief of Army experienced a baptism of fire when he left the military to run for public office.
Then 41, Mr Chan Chun Sing was one of the youngest among the Cabinet members when he was appointed Acting Minister for Community Development, Youth and Sports (MCYS) after the 2011 General Election.
He went on to helm the newly created Ministry of Social and Family Development (MSF) in 2012 before taking over as a full Minister a year later.
His rise was among the swiftest among the 2011 batch of new politicians, and whispers of him being a future prime minister followed.
But his informal speech and mannerisms rubbed some people the wrong way.
Brickbats and derisive comments came, fast and furious, especially on the Internet.
The 45-year-old said: "Of course, (nobody) would want to have such unpleasant experience(s) but it's almost inevitable (when you take) this road; you will get your fair share of such nasty incidents.
"You just hope that it doesn't affect you personally and your family."
During the hour-long interview at his Marina Bay office last week - before the General Election date was made known - Mr Chan often peppered his answers with Chinese sayings.
Asked if the vitriol stings him, he answered: Be in this for the correct reasons, do things conscientiously and wen xing wu kui (Mandarin for clear conscience).
His latest move to the National Trades Union Congress (NTUC) this year also set tongues wagging once more: Was it a prelude to the top post or a step down?
"I've never been the type to choose what I want to do or where I want to go," Mr Chan said.
"I never thought that the PM will send me to MCYS and then MSF, but I'm given a task and I try my best to do what I can, make a contribution to take care of the people whose lives I am charged to take care of.
"It's (not) about what you do individually that's important. It's about what we do as a team that's important."
Hence his joking promise to put his ex-MSF colleagues out of a job: "The better that I take care of the workers, the less busy MSF will be."
When it comes to sharing his thoughts online, the father of three said: "I don't spend every moment thinking how to boost the number of 'likes'.
"Because very early on in my career, I have come to the conclusion that the number of (Facebook) likes has no correlation to the English word 'like'."
WHO: Chan Chun Sing
WHAT: Minister in the Prime Minister's Office and secretary-general of National Trades Union Congress
FAMILY: Married with a daughter, 14, and two sons, six and three
CAREER SO FAR
2011: Acting Minister for Community Development, Youth and Sports and Minister of State for Information, Communications and the Arts
2012: Acting Minister for Social and Family Development and Senior Minister of State for Defence
2013: Minister for Social and Family Development and Second Minister for Defence
2015: Secretary-general of National Trades Union CongressThe former Chief of Army experienced a baptism of fire when he left the military to run for public office.
Mr Chan Chun Sing on...
DEALING WITH DETRACTORS
When his children read nasty comments about him, they often question why he has to be a public servant.
For example, when people make fun of ministerial pay, Mr Chan said his kids' likely response would be: "Why don't I return you the million dollars and you return us our father?"
It is tough facing such scrutiny, he said.
But his family has matured and knows there's a purpose behind what he does.
He said: "There must be some things that keep us going (like) this country. You can't be in this because of money. As much as people like to think that ministers earn a lot of money, my mother would say: You qian dou mei ming hua. (Translation: You have money but no life to spend it.)"
MR LEE KUAN YEW
As they were MPs for Tanjong Pagar GRC, Mr Chan was often seen physically helping Mr Lee during grassroots events.
Among the topics Mr Lee would bring up: How residents were doing, if something could be done better, what's the situation in Singapore, around the region and in the world.
Seeing the residents' tremendous respect for the frail Mr Lee was very touching, Mr Chan recalled.
"They would say he's old, (we shouldn't) trouble him. (That's why) as the younger generation, it made us very determined to do our best so he wouldn't worry about the constituency or the country... (But) Mr Lee being Mr Lee, (he) would always think about the country and the residents without rest."
The contrast can be surreal, said Mr Chan.
For example, at one table, there would be an uncle who is down and out, asking for help to supplement his income.
Then there would be a newly married couple at the next table, asking why they couldn't get the housing grant they wanted as their combined monthly income breaches the limit.
He said: "Their needs are so different, their expectations are so different... You dig deep and ask: How to help them given the finite resources?'"
THE VOTER'S CHOICE
Every election is about choosing leaders for the country for the next lap and having people focus on that.
And Mr Chan doesn't think it's a conflict, in terms of having to choose the best talent versus having to choose someone you like.
He said: "We always hope that the majority will be able to take the perspective that elections are about the future of the country, (the) choice of leadership, (who's best) to take the country forward and not just about who may seem more likable and popular.
"You cannot just be likable and popular without having the correct values, right? Leaders need to be everything, but you cannot be everything to everyone and (have) no substance."
This article was first published on August 31, 2015.
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