Before the euphoria of making history in the pool yesterday, the Schoolings had to first endure seven years of toil on the road to the top of the Olympic podium.
It began with the difficult decision of sending their only child halfway across the world in 2009 to the United States, in pursuit of the training environment that could mould him into the world-beater he is today.
Joseph Schooling, just 14 then, was the one who pleaded to go. His parents were the ones hesitant to take the leap of faith.
Hours before Schooling's historic swim yesterday, his mum May recalled to The Sunday Times how the swimmer's obsession with competing at the Olympics began after meeting his grand-uncle Lloyd Valberg, coincidentally Singapore's first representative to the Games at the 1948 London edition.
To help Joseph fulfil his dream, they sent him to the Bolles School in Florida, but endured a trying start. The champion himself said yesterday of those early days: "I wasn't the easiest guy to train. I didn't want to be there."
Husband and wife took turns shuttling between Singapore and Florida to take care of their young son, each staying months at a time.
It meant the family of three were separated more than they were together, spending an average of just three weeks together a year.
Said Mrs Schooling, her voice hoarse from days of cheering her son on from the stands: "I have got to take care of two households on both sides of the world.
"It has been tough. Tough because we are not getting any younger," said the 60-year-old.
"As it is now, I am finding it more and more difficult to get over the jetlag of long haul. Age is catching up."
She is a chartered accountant, while husband Colin, 68, is a businessman. He was not in Rio as he was not feeling well.
But after watching the live telecast from the home of Joseph's good friend Teo Zhen Ren, a fellow national swimmer, Mr Schooling's first words to his son were: "I love you. Son, you have done the nation very proud."
In Joseph's build-up to the Olympics, Mrs Schooling travelled to Austin, Texas, where he is now based, to make sure that his meals and needs were well taken care of.
Financially, it has also drained the family. Tuition, accommodation, transport and other expenses over the years has required a hefty investment of nearly US$1 million (S$1.35 million).
Joseph is also a Sports Excellence scholar. The scholarship supports elite athletes with up to $90,000 in median annual stipend to train and compete at the highest level.
Mrs Schooling said: "It is tough on family life, missing each other. Financially, it has also been a big juggle, using up all our reserves and having to budget like crazy.
"It has been tough on all of us, but he wants it."