Life As A Homeless Man

By City Of Good  /
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Get an education. Get a job. Typical advice from parent to child, so one won’t end up homeless. Yet in David’s* case, he ended up living on the streets for 4 years despite having both. This is a story of one man’s pain, resilience – and hope for the future. 

*This is a pseudonym. The interviewee’s real name has been changed to protect his privacy.

Last month, news broke that Singapore has approximately 1,000 homeless people on the streets. These were startling figures – but what drives a person to end up sleeping rough? What dreams do they have?

To find out, interviewed David*, an O-level graduate who worked as a salesman, fast food chain worker before starting his own maildrop business. He described himself as a man with no vices – no smoking, drinking or gambling.

Yet, a series of unfortunate events left him homeless for almost 4 years, drifting between living in a taxi, a jail cell and HDB void decks. This is his story.


Together with his twin brother, David grew up in a landed terrace in Singapore. His father was a bookkeeper, and his mother was a nurse.

Things changed after David’s father was diagnosed with cancer, when David was in his 40s. Although his father had intended to sell his property and split the proceeds between his wife and two sons – “Plot twist! My father did not write a will,” David lamented. In a further twist, David’s mother sold the house, took the proceeds for herself and started life anew. “She left me and my brother behind, and was never to be contacted again.”

This left David without a home for the first time, together with his twin brother who had lupus. They pursued their maildrop business and rented a new flat. But tragedy struck. “My brother passed away a year later,” David shared.  “My world crashed. It had been the two of us against the world.”

He eventually folded his business which had been struggling and started driving taxis to pay off mounting debts. He even had to give up his home as he could not afford the rent.

Life As A Homeless Man 01
David became a taxi driver after losing his flat and business.


“The taxi was like my mobile home,” David explained. “It was fine until people started complaining that there were too many items in the boot.” His daily necessities were kept in the taxi, whilst other important belongings were kept at a storage space. “I kept my late father’s and late brother’s death certificates there, as well as old photos and videos. Sadly, I struggled to upkeep the rental of the storage space and eventually, my important belongings were thrown away,” David sighed.

David’s life took an unfortunate turn in 2016. While driving his taxi one evening, he collided into a elderly man who had jaywalked. “I tried to resuscitate him, but he was already bleeding on the ground.” Unfortunately, the man passed away in the hospital three hours later.

The accident brought David to court, where he was unable to afford a proper defence. “My salary was too high to be eligible for a pro-bono lawyer, yet I couldn’t afford a defense lawyer,” David explained. “The judge reprimanded me for negligent driving. I was given 7 days [in jail].”

Life As A Homeless Man 02
For negligent driving, David served a 7-day jail sentence

Most would find jail to be a grave prospect. But for David – “Jail became a shelter, because you are given food and a bed.” This offered him solace despite losing his driving license and getting bullied by other prisoners whenever he prayed. When he left prison, all he had was his backpack. “My backpack included a water bottle, a portable electric fan, and some writing materials because I kept a diary.”


Next, David started sleeping rough underneath HDB blocks. He frequented Ang Mo Kio Central, where McDonald’s provided free-flow of coffee for paying customers. David would find a leftover cup, wash it in the toilet, before using it.  “With the little money I had, I chose to purchase a sanitizer,” David shared.

For breakfast, David bought buns using his meager savings. For lunch, he bought vacuum-packed food that was already cooked such as fishballs. For dinner, he ate instant noodles; when he could find a plug at coffee shops, he would use an electric kettle to boil water.

For showers, he went to the handicapped toilets in different shopping centers, bathing at early hours while also washing his shirt. With only one pair of clothes, he would clean his shirt and immediately put it on after.

Through all this, David was determined to get his life together and pay off his debts. He bounced between two jobs for two years, working as a dishwasher from 7.30am to 4.30pm and a toilet cleaner from 6.00pm to midnight.

As hard as it was, it got even harder when David contracted a peripheral artery disease which limited blood flow to his leg and caused it to swell. The pain was unbearable. “I was at my lowest low. I couldn’t sleep. I couldn’t eat. I quit both jobs. I did not have Medifund, so my medical bills kept accumulating. I briefly contemplated suicide because I felt so helpless,” David earnestly shared.


Luckily, a social worker recommended him to a New Hope Community Services shelter and he soon moved in.

“New Hope Community Services really helped me find new hope. It is truly a haven!” David exclaimed. Whilst there are curfews, David is able to freely depart the premise for his part-time job as a dishwasher every day. He no longer has to worry about finding a new place to sleep every day. “I was surprised as initially I thought the shelter was only a place to sleep, but this shelter even provides breakfast; hot drink, snacks, occasional lunch and dinner,” David gratefully commented. This allows David to focus on his job and getting back on his feet.  

His experience at New Hope Community Services has made him more community-oriented, where he would sometimes cook food for others. He also contributes to the shelter’s shared facilities and necessities. “It makes sense that we’d have to contribute $2 to use the washing machine or some people may take advantage and waste electricity,” David commented. With everything that New Hope Community Services has given David, David is determined to pay off his debts and then return to New Hope Community Services as a volunteer. This is to help others that were once in his shoes.

Life As A Homeless Man 03
For the past 2 months, David has found shelter at New Hope Community Services.

His greatest wish in sharing his experience? That Singaporeans will become more compassionate to the homeless. David recounts that during his rough sleeping days, he encountered kind strangers who would leave him buns while he was asleep. Yet others would harass and kick him.

Through it all, David’s faith kept him persevering even when times were tough. “Through my story, I hope Singaporeans realise that people become homeless because of circumstances, not because they are lazy,” he advises. “Sometimes all people need is a little respect and support to get back on the right track and become independent again,” he finishes.

Would you like to help people like David?