Author Sebastian Sim has been a bartender, a croupier and a prison officer. He has cut cards for high rollers, reprimanded gangsters and watched customers spill drinks and sob stories across the bar.
To many, the 51-year-old may seem like a drifter. But this itinerant job-hopping is tied to a singular purpose conceived when he was a 17-year-old junior college student - to be a writer.
"I choose to do shift work so I can save the best hours of the day for writing," says Sim, who is now an office executive. "I did not want to be sucked into the rat race. Work for me is just income and an avenue to collect life experiences."
It has taken a few decades, but his strategy finally seems to be paying off. Last Thursday, he won the third Epigram Books Fiction Prize - which at $25,000 is Singapore's richest literary prize - for his upcoming novel The Riot Act, about the aftermath of the 2013 Little India riot.
It was second time lucky for Sim, who was shortlisted in 2015 for comedic novel Let's Give It Up For Gimme Lao!, but lost to O Thiam Chin's Now That It's Over.
Gimme Lao, published when he was 50, is his first English-language novel. He is also the author of three wuxia (martial arts) novels in Mandarin, none of which sold out its first print run.
The win came as a surprise to Sim. It is a long-awaited validation of his youthful decision to "be willing to be misunderstood" by his career-centric, stability-seeking peers.
I choose to do shift work so I can save the best hours of the day for writing... Work for me is just income and an avenue to collect life experiences.
AUTHOR SEBASTIAN SIM, who is now an office executive
He gave up a place at the faculty of arts and social sciences at the National University of Singapore so he could travel the world.
He flew to New York City to knock on publishers' doors with his first manuscript, a horror story inspired by Stephen King, but all he got were rejections.
After some years backpacking around the world, he took up various jobs - including as a waiter in an Italian restaurant, a McDonald's manager and a Boat Quay bartender. He kept journals of his people-watching observations and wrote fiction, for which he likes to draw mind maps.
In his 30s, he spent eight years supervising drug traffickers and gangsters at a maximum-security prison.
"I was curious about this unique environment, which sharpens everyone's behaviour," he says. "It's interesting to see what people do to win privilege and survive gangs."
He learnt a great deal about people management in prison, such as how a gangster is more likely to listen to you if you take him aside, instead of upbraiding him in front of his "brothers".
He also saw facets of society unfamiliar to the average Singaporean, such as how the poverty trap forces youths into gang culture. He drew on this to write characters such as Black Cougar, a brooding gangster in Gimme Lao.
From the underbelly of society, he went on to deal with the creme de la creme as a croupier at Resorts World Sentosa. This gave him a ringside seat to the bad behaviour of some of the casino's richest patrons.
"If they lose badly, they will spit on the card, crumple it and throw it at you."
At the other end of the spectrum, he watched foreign workers pin their hopes on $10 bets. "When they win, they really jump for joy."
His fascination with the cracks in the system led to him writing The Riot Act.
It was with disbelief that he watched footage of the Little India riot, in which angry mobs attacked a bus after the fatal accident of a worker from India.
"We thought it had to be happening somewhere else, not in safe and orderly Singapore."
The novel is told from the perspectives of three Singaporean women: Hashwini, whose guilt over her part in the riot does not stop her from exploiting the tragedy to become a social media influencer; Jessica, a student injured during the riot, who both the government and migrant worker advocacy groups try to sway to their agendas; and Sharon, a Member of Parliament who sees the riot as a chance to further her political career.
"The riot was a big shock," says Sim. "The population woke up to the fact that Singapore is not as smoothly crafted as the Government would like you to think. There needs to be more alternative narratives."
Sim, who is in a relationship, lives with his mother, 80, and younger brother in a five-room Housing Board flat in Ghim Moh. His father died of heart failure when he was 17.
He prefers to write either from 3am - until he has to leave for work at 6am - or on his days off at a Han's cafe near his home.
He plans to use the $25,000 prize to take his mother on holiday and learn paragliding, which he has wanted to do for a long time.
While he has not settled on plans for his next novel, he says he hopes at some point to return to writing Chinese wuxia and also more books based in Singapore. "As Singaporeans, we are in the best position to tell our own stories," he says.
• Let's Give It Up For Gimme Lao! ($26.64) is available at major bookstores. The Riot Act will be published next year.