PUBLISHED ONJanuary 28, 2026 7:27 AMBYEsther LamWhile many of us rarely think twice about having a place to sleep or food on the table, Lipson had to navigate financial struggles and was homeless three times as he prepared for his O-level examinations.
In an episode of YouTube series Gen Z Crash Course posted on Jan 23, the polytechnic student shared about the tumultuous period in his life and said: "I was born into a normal family, but when my father passed away, things started getting complicated."
Having reportedly been homeless three times, Lipson often sought temporary refuge in public toilets in parks, where he slept while airing his school uniform or jacket on the handicap railings to dry.
At times, he would sit on the toilet bowl and lean against the paper dispenser but if the floor was dry, he would sit on the ground, hugging his backpack as he slept against the wall.
"You are always on high alert. Even when you're sleeping, the slightest noise can wake you up," said Lipson. "You can't really get any proper sleep."
Lipson also often went jogging in the park as a form of exercise but also to tire himself out as he felt it was "the only way to get proper sleep".
He added that when people would knock on the door while he was resting inside, he would pretend he had been using the toilet before quietly leaving. He would frequently change locations in fear of being recognised and reported to the authorities.
He also went to malls and nearby 24-hour restaurants which usually had security patrols and he would try to avoid the security guards by remembering their patrol schedule.
Back then, the most important things to him were shelter, especially places that not too many people frequent, a place to freshen up and a place to charge his phone, said Lipson.
As for his daily meals, Lipson shared that he frequently stayed late in school to study for his N-level examinations and the canteen aunties and uncles would offer him food.
He also worked occasionally and would earn enough to buy a can of tuna or biscuits from the value dollar store.
He kept up his hygiene by washing his clothes at laundromats, using coins that other people had dropped behind the machines.
However, Lipson also had his moments where it felt too much to bear.
He admitted: "There were definitely many times where I wanted to just give up in general. I didn't know how long I could take it — the isolation, the loneliness, especially such a stressful event that could predict my life — my N levels and O levels."
He shared that despite his achievements in secondary school, having received the best improvement award and being the head counsellor, there was "no one waiting at home for you".
At the time, Lipson had a scrapbook to record down his thoughts and emotions, he said.
Pulling out a limited-edition chocolate wrapper which was gifted by his then-partner, Lipson recalled it felt like a symbol of hope and helped him realise he still had a fighting chance.
"I still have a chance to have a family, I still have a chance to have a life. I still have a chance to experience things and that not everything is over for me," he said.
Holding a set of headphones gifted to him by an online friend, Lipson shared that music also helped him cope with the overwhelming thoughts.
Initially, Lipson did not share his financial struggles or situation with his friends or teachers as he feared the social backlash and repercussions, worrying that others would make judgements about his hygiene.
He eventually found the courage to share about his situation on social media and as people started reaching out to him, Lipson accepted the help from his friends.
Lipson was able to overcome the odds and score "near a single digit" for his GCE O-level examinations and is now pursuing a diploma in biomedical science.
After graduation, Lipson hopes to render aid to those in his position and repay the kindness he was shown.
"It's not about the cards you're dealt with, it's how you deal with the cards. You don't give up, and you'll end up in a better place, definitely," he added.
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