The country's original "Golden Girl", one-time swim queen Patricia Chan has been through it all.
She carried the weight of the nation on her shoulders en route to 39 gold medals at the South-east Asian Peninsular Games (now the South-east Asia Games), she won medals at the Asian Games and competed at the 1972 Munich Olympics.
She had to endure media scrutiny, was constantly asked about her medal chances and was never left alone when she failed to meet expectations.
So when the subject of Joseph Schooling comes up, Chan has some advice for Singapore - ease off the pressure.
"I used to have the press write how many medals I was going to win, and it was the most irritating thing," the 62-year-old said on Thursday (May 19) on the sidelines of an aquatics exhibition at the Kallang Wave Mall.
"For young people to have that pressure on them, you have to respect what he wants to do and (separate it from) what he ought to do."
Excitement is building as the clock ticks down to the Olympics in Rio from Aug 5 to 21, with a growing number believing butterfly sprint star Schooling can deliver Singapore's first Olympic gold.
Schooling is in the form of his life in the 200m butterfly, which will also see American superstar Michael Phelps in the field.
Chan warned against such predictions.
"In my lifetime of watching a lot of the Olympics, there's always somebody, somewhere who's a dark horse," she said.
"We would love for Joseph to do spectacularly, but to speculate, many slip, as they say."
At just 20 and 19 respectively, Schooling and fellow Olympic 'A' qualifier Quah Zheng Wen have big futures ahead of them, and the 2020 Tokyo Olympics will probably be an even better bet for the duo.
But, with the pair set to fulfil their National Service (NS) duties - they were both granted deferments by Mindef to be able to concentrate on preparing for this year's Games - after their commitments in Rio, questions have been raised on how the two talented swimmers could be helped to become even better for 2020.
Singapore Swimming Association (SSA) marketing and communications director Mohamed Hafidz said yesterday there were no plans right now to request a second deferment for either of the two athletes.
"In terms of planning, we don't know what Mindef is going to do. So for the two of them, it's going to be competing at the Olympics and then coming back to Singapore," he said.
Hafidz said there could be a case for athletes to combine NS with elite-level training.
"Sport Singapore, SSA and Mindef are always in talks on how we can actually do that," he said.
"We're already talking to them about our next generation of athletes, those who are 16 and 17, and how we can help."
For Chan, deferring NS for top-level athletes is a "big decision".
But even if Schooling were to fall short at August's sporting extravaganza, Chan said Singaporeans should not come down too hard on him.
"What we have to learn as a nation is to understand maturely that everyone has good and bad days, and in a bad time, encouragement does a lot more than criticism," she said.
"I know this boy, he will give his utmost; that's his nature and that's what makes him a champion, whatever the outcome."
This article was first published on May 20, 2016.
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