With his parents busy at work, "Desmond" dropped out of the Institute of Technical Education in his final year and did what many of his friends were doing: join a gang.
He did so as he did not want to "feel left out", but in October 2010 he ended up in jail over gang-related offences.
However, he became determined to make something of his time behind bars and took part in the National Youth Achievement Award (NYAA).
Yesterday the 22-year-old joined nine other inmates in receiving the NYAA's silver honours from Mr Lawrence Wong, Acting Minister for Culture, Community and Youth.
Desmond, whose real name cannot be used due to prison policy, is in jail on a yearly review and joined inmates to plan a programme for beneficiaries of the CARElderly Activity Centre.
They did song and dance routines for the seniors, who visited the prison, and helped them with activities such as handicrafts.
"I was given a lot of leadership opportunities," said Desmond, who received the bronze award last year. "I felt a deep sense of satisfaction when I saw the smiles on their faces."
The NYAA programme was set up in 1992 to mould 14- to 25-year-olds into responsible and self-reliant adults. Participants either pursue a bronze, silver or gold award through activities like sports, community service and learning new skills.
Addressing the award recipients in the auditorium of the Tanah Merah Prison, Mr Wong said: "One of the most precious things about being young is that life is full of potential.
"You may have faced some bumps along the road and encountered some setbacks along the way. Take these in your stride, and continue to believe in yourselves."
There were 70 bronze award recipients but no gold winners.
As part of the NYAA programme, Desmond also learnt basic video-editing skills, took part in a two-day football workshop, and had lessons in outdoor skills such as rope work techniques, tent building and map reading.
Yesterday, Desmond also got to spend time with his mother and sister in a rare open visit. Instead of being separated by a thick glass screen, the trio sat together and shared hugs as they chatted.
His 46-year-old mother said: "When he was sent to prison, I kept asking myself, 'Where did the family go wrong?' But we learn from our mistakes and the family is much closer now. We encourage and support him in everything he wants to do."
This article was published on April 15 in The Straits Times.
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