Minister of State for Culture, Community and Youth Alvin Tan had to repeat the first year of his junior college.
Even after that, he did not score well for his A levels — getting two "Ds" and a "C" — and could not attend a local university.
His relationship with his then-girlfriend also ended while he was doing his national service.
"I felt really down, very low... when you are in a depressive state, it feels as though you are in a washing machine — you do not know which way is up," said Mr Tan, who is also the Minister of State for Trade and Industry.
But he had friends who helped him through this dark period in his life, he said.
The minister also said it was okay to seek help by attending counselling.
He was sharing his experiences with failure in an online discussion on Saturday (Feb 6).
The session, "Let's Talk About Failure", was organised by the Moulmein-Cairnhill Mental Health Task Force.
The task force is part of the Moulmein-Cairnhill Citizens' Consultative Committee and aims to strengthen mental wellness in the community.
The other panellists were Ms Shilpa Jain, founder of online counselling platform Talk Your Heart Out, and Mr Simon Leow, who co-founded social enterprise the Happiness Initiative.
Mr Tan, who is also the grassroots adviser to Tanjong Pagar GRC, said he experienced impostor syndrome when he first became a minister. Impostor syndrome is the belief that one is not as competent as others view one to be.
He addressed this by asking his more experienced peers for help.
"You recognise that you need help, you ask for coaching, and... you start to build (resilience)," he said.
Mr Tan said it was fine for people to seek counselling, adding that he and his wife had done so to improve the quality of their marriage.
"It is not just one shot and a magic pill — you constantly want to give it time, effort and to have a third-party perspective to help you build... something that you cherish," he said.
Ms Jain agreed, saying that getting a professional counsellor who is objective and can help clarify one's thoughts in the right way would be helpful.
And one need not have a problem to attend counselling, said Mr Leow.
"Sometimes... because we want to improve the quality of our relationship with other people or...with ourselves — that is why we go and see a counsellor," he added.
Psychologist Annabelle Chow told The Sunday Times that she was proud of Mr Tan for publicly sharing his experiences with failure.
"I imagine it is very difficult to admit any kind of fragility or vulnerability, especially when you are in (public) office," she said.
She added that the topic of failure is not discussed widely enough, given that it is frowned upon in today's society.
Dr Chow hoped the session would encourage people to speak about their own experiences and reduce the social stigma of sharing them.
Participant Paley Kuang, who works in real estate, said: "(The discussion) was such a breath of fresh air, in a society where we do not talk much about our failures."
The 48-year-old added that she enjoyed the personal stories shared by the panellists and she was looking forward to more of such sessions.
This article was first published in The Straits Times. Permission required for reproduction.