Mr Rizwan Habib, who stole money as a child to feed his mother's drug habit and spent close to 21 years in jail across seven jail terms, celebrated a series of remarkable milestones in the past year.

The 43-year-old, who took his PSLE, O levels and A levels behind bars, completed his social work degree at the Singapore University of Social Sciences in April.

In May, he started his "dream job" as a social worker with the Industrial and Services Co-operative Society (Iscos), helping ex-offenders to turn their lives around.

He also moved into his first home, a two-room Housing Board flat, in November 2024.

Mr Rizwan, who was once homeless and spent a large part of his life in jail, said: "I never had a place to call home before. It feels surreal."

A traumatic childhood

Mr Rizwan said that when he was about five years old, his father walked out on the family.

His mother was an unemployed drug addict, and as an only child, he had to fend for himself from a young age.

He started stealing and committing other petty crimes at the age of 11 to feed his mother's habit, as it pained him to see her suffering from withdrawal symptoms when she tried to quit drugs. He also stole to support his family.

He said: "My mum and her boyfriend looked to me to find money. And we didn't have food. We had to survive."

He dropped out of school at Primary 2.

They were homeless, and his mother had a host of problems, so sending him to school was not a priority.

He and his mother, together with her boyfriend, lived in a derelict unused temple for a period of time. A nearby well provided them with water, and they used candles and kerosene lamps for light.

Poverty and homelessness aside, what frightened him more as a boy were the snakes he saw around the temple.

When he was 12, Mr Rizwan was arrested for the first time and sent to the Singapore Boys' Home and the Reformative Training Centre for three years.

During that time, his mother died of kidney failure. At 14, he became an orphan.

"My life started going downhill after her death. I only had my mother, and now I'm alone," he said. "I didn't know what to do."

His mother's death tipped him into a pit of anger, and a life of crime. His friends in jail felt like a surrogate family to him.

He decided he would become a hard-core gangster, going to the extent of tattooing the words "hard core" and his gang's name on his hands.

"When I was 15 or 16, I felt the life outside (prison) was very alien. I had no education, no family, no home, no skills," he said.

"And I felt that prison life, with its routine and discipline, was the only life I was familiar with."

In all, he was jailed seven times for drug and gang-related offences, and given 38 strokes of the cane.

The total length of his seven jail terms added up to almost 28 years, before his remission for good behaviour.

His longest stint out of prison before he was arrested again was 13 months.

The shortest was just one month.

Each time he was a free man, he fell back into his old ways - drugs, his gangster friends and the lure of making a quick buck from illegal activities.

The road to redemption

His journey from prisoner and primary school dropout to university graduate and social worker started with his love for reading.

He said: "My mum would get me to read the newspapers to her. She told me: 'Rizwan, don't stop reading.' I think this helped me appreciate knowledge and education."

While in jail, he taught himself to read newspapers with a dictionary by his side.

Reading took him out of the confines of the prison cell and broadened his world view, and he read all kinds of books he found in the prison library.

Encouraged by the prison officers, he did his PSLE and O levels in his 20s at the prison school. He took the A levels in his 30s behind bars too.

The fear of growing old and dying in prison - like some inmates he saw around him - spurred him to turn his life around.

"Do I have to keep blaming everyone else for what happened to me? I don't have to be a prisoner of my past," he said.

"I wanted to change, but how? The 'how to change' part kept escaping me. So I started reading books about habits, as I realised my habits were leading me back to prison."

Among the books that shaped his thinking were Daniel Kahneman's Thinking, Fast And Slow; Malcolm Gladwell's Blink: The Power Of Thinking Without Thinking; and John Steinbeck's The Grapes Of Wrath.

Mr Rizwan decided he had to shed his identity as a thug.

He found a stable job, first at a call centre and later at a tech firm, after his release from prison at the age of 37.

He made new friends and avoided old temptations or people from the past who could lead him down the slippery slope again. He started to exercise and learnt to enjoy his own company.

Touched by a social worker he had met in jail who went the extra mile to help him, he also pursued a part-time degree in social work after his release to be a guiding hand for others.

"Her concern and sincerity really touched me, and she visited me in prison even after she was no longer my social worker. Nobody had visited me in jail before," he said.

"I thought I could make use of my life experiences as a social worker to do the same for others, like what she did for me."

Today, Mr Rizwan works with inmates and ex-offenders, as well as their families, to help them turn over a new leaf after their release.

Because he had walked a similar path, sharing his past with some of them has helped to build rapport and trust. For him, the work is deeply fulfilling.

New life, new bonds

Mr Rizwan now lives with his girlfriend Elizabeth Neo, 36, her six-year-old son from her previous marriage and their three cats in his new flat in Tengah.

Ms Neo, a part-time waitress, also has a painful past - three stints in jail for drug offences and an abusive former partner.

The emotional scars carried over to the early days of her five-year relationship with Mr Rizwan.

"We were both very broken people. In the past, we were very hot-tempered, hot-headed, and we would physically fight. At times, I would slap or bite him," she said.

"But now we no longer have huge fights. Rizwan has changed a lot, and he doesn't flare up so easily. He is more willing to listen first."

The couple had joined the Brotherhood programme, which helps abusive men break the cycle of violence, run by Thye Hua Kwan (THK) Moral Charities.

Mr Rizwan, who once attended the programme to deal with his anger issues, is now a buddy and a mentor to the other men in the group.

Both he and Ms Neo also volunteer with the Singapore After-Care Association to befriend ex-offenders and inmates.

Mr Ben Ang, centre director for THK Family Service Centre @ Bedok North, said: "Rizwan connects with ex-offenders and at-risk individuals in ways no textbook can teach because he has lived through what they're going through. He walks alongside them with empathy, respect and understanding.

"Today, Rizwan stands as a powerful testament to resilience, redemption and the possibility of change."

At the urging of an aunt, he found his father through Facebook about three years ago.

However, he has mixed feelings about their reunion, as they were estranged for most of his life.

His father apologised for his past actions. Mr Rizwan said: "I'm okay talking to him, but I think it will take a lot of effort to rebuild the father-son relationship."

For now, he is thankful for the second chances he has had - studying behind bars, surviving a serious stabbing during a gang fight and the indescribable happiness of having a home to call his own.

He said: "I'm very happy now, and I'm at peace."

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This article was first published in The Straits Times. Permission required for reproduction.