Giving up a $90,000 salary to job hunt Down Under: S’poreans risk it all to move abroad with no job

Cherie Lok
The Straits Times
June 27, 2026

In 2024, life was going well for Pek Yi Tsing. She had her dream job at an aviation company that paid more than $90,000 annually and was travelling every other month.

Yet, it was the fear of getting too comfortable that pushed the former senior social media executive to look for a way out of Singapore. “I knew that if I stayed any longer, I would not want to leave,” recalls the 30-year-old communications graduate.

She had been trying to relocate since a year-long stint with a Taipei-based company in 2016 gave her an intoxicating taste of life overseas.

So, she applied for Australia’s Work and Holiday visa, which allows 18- to 30-year-olds to holiday in the country for up to a year while working to fund their trip.

Together with her journalist husband, she booked a one-way ticket to Melbourne in March 2024. They went carrying nothing but a suitcase and the hope that all the pieces would somehow fall into place.

And they did, for a while. After two months, a marketing job materialised from the 800 applications she sent out. So began two years of knocking off at 5.30pm sharp every day – her boss once apologised for making her work until 5.40pm — and weekend road trips around Australia.

Her husband, who took longer to find work, eventually settled for a remote position writing for an automotive publication.

Given the volatility of the job market, theirs was a risky road and perhaps the one less travelled by aspiring “expatriates” here.

While most people relocate for work or love, why do these millennial and Gen Z Singaporeans give up the comforts of home for a new life in an unfamiliar city before securing so much as a job interview?

How they moved

In April, 27-year-old Singaporean Jordan Ong moved to New Zealand on a Working Holiday Visa, which lets Singaporeans with university qualifications aged between 18 and 30 work in temporary jobs for up to 12 months.

There, the RMIT University business graduate looked for a non-desk-bound job that would let him “get his hands dirty”.

His girlfriend Siara Tan, 27, who has a diploma from Nanyang Polytechnic but no university degree, accompanied him on a visitor visa. It allows holders to remain in the country for up to six or nine months, though they cannot work while on this visa.

Still, Tan, who is open to all sorts of work, is hoping to find a company that will sponsor an Accredited Employer Work Visa for her. Priced at NZ$1,540 (S$1,130), the visa requires, among other things, applicants to have an offer of full-time work from an accredited employer.

“The job hunt is a bit slower than we thought because it’s winter now, so not a lot of companies are hiring and most tourists are in Queenstown,” she says. Even supermarkets have turned them down as packers.

She hopes the job market will pick up in summer when extra labour is in higher demand. Meanwhile, she is working remotely on her social media portfolio, creating user-generated content for companies, earning around $230 a week.

Other countries offer dedicated visas for job seekers.

Stanley Foong, 28, for instance, is living in Tokyo on a J-Find visa. It allows individuals who graduated from top universities — including the National University of Singapore (NUS), where he finished his Bachelor of Science (Real Estate) in 2023 — within the last five years to remain in Japan for two years while they search for work. They must have at least 200,000 yen (S$1,600) worth of savings at the time of application.

Over in London, Dionne Wong, 27, an NUS business administration graduate, took advantage of the High Potential Individual Visa (HPI) to move to Britain. Similar to the J-Find visa, the HPI requires applicants to have graduated from an eligible university no earlier than five years prior, and they can remain in the UK for up to two years.

It cannot be extended, but holders can switch to a different visa, such as the Skilled Worker visa, if they manage to land a job.

This route was launched in May 2022, around the time Wong started working as an asset management graduate trainee. She was intrigued by the prospect, having tried and failed to move overseas several times – first for university, then while working at a multinational bank.

When it became clear that the bank she was working for was not likely to post her overseas, she decided to bite the bullet.

“It wasn’t a sudden desire, but something I had wanted since high school, and I didn’t want to wait any longer for someone to give me the green light to do this,” she says. Gathering fate into her own hands, she moved to London in August 2024.

Because she was still burnt out from work in Singapore and preoccupied with flat hunting, she did not start looking for a job until 2½ months later. Fortuitously, she was able to find something within a few weeks – a part-time role at a finance start-up which helped pay her rent.

In search of a different lifestyle

Others are content to continue working remotely overseas. Chen Shao Chun, 40, runs a YouTube channel (@9to5MillionaireMindset) and a fractional consultancy from home. He moved to Chiang Mai in November 2024 and now lives in a 480 sq ft condo.

He estimates he makes about $3,000 a month on average, including from occasional gigs and speaking engagements, which see him returning to Singapore every few months. It is a fraction of what he used to make as a sales head at Google, but for just three hours of work a week and a more relaxed lifestyle, this is a trade-off he is willing to make.

Under his Destination Thailand Visa, which costs $500 and allows digital nomads and freelancers to remain in Thailand for up to five years, he can work remotely. That is why he says he never intended to apply for a job in Thailand. “The pay there is 40 to 60 per cent lower, the tax rate much higher and I won’t have any competitive advantage because I don’t speak the language.”

Initially, Chen was worried that being holed up at home with his computer all day would give him cabin fever. But life in Chiang Mai has turned out to be the opposite.

“It’s not boring at all,” says the father of one, surrounded as he is by strawberry farms, lakes and mountains, vibrant nightlife, sports galore and meditation retreats, not to mention fantastic food at $2 to $3 a meal.

Plus, its proximity to Singapore makes Chiang Mai the perfect bolthole for the former finance bro, who was looking to escape the high-stress corporate treadmill after he was laid off in February 2024. “I never actually lived abroad, and the terrible job market felt like the perfect excuse to sit out the corporate rat race, and try a completely new way of living,” he says.

The promise of a more evenly paced life drew Tan and Ong to New Zealand as well.

“We love life here because it’s really slow and we can do so many more things. New Zealand regulates our nervous system,” Tan says over a Zoom call from Diamond Harbour, a village on the Banks Peninsula, where her boyfriend is currently fishing. She pans her phone around to reveal turquoise waters, sun-kissed trees and the undulating outline of a mountain range in the distance.

“Being in nature makes our problems feel very small, like we’re just a speck in the universe.”

It is the kind of weekday afternoon the Singaporean couple could once only dream of. Until February, Tan was hustling as a financial consultant in Singapore, while Ong, who graduated in mid-2025, was working a series of internships.

A 12-day road trip around New Zealand in 2024 showed them life had so much more to offer than the standard trajectory of getting a job, getting a house and getting married, as espoused in the Singaporean playbook.

“It’s the same cycle for everyone, which I feel is very boring,” Ong says.

Tan adds: “I guess you could say we’re running away from the pressure to conform. At this age, everyone’s climbing the corporate ladder. But here we are, living pay cheque to pay cheque. But you choose the life you want to live and deal with the consequences.”

Earlier in 2026, the couple made their choice, landing in Christchurch, New Zealand, with just $7,000 in savings.

She was warned by many that she would suffer by moving without the security of a job. And while the journey has indeed been tough – Tan has yet to find a job while Ong works as a car groomer making NZ$1,800 a fortnight – she says it is hard to feel like she is suffering in a place like this.

Middle-class life is a lot “more breathable” here, she says, with far more affordable housing and car prices.

They are living “comfortably” on combined earnings of around $900 every week, which covers rent (NZ$320 a week), groceries and petrol. Home is a rented en-suite room and they drive a used Mitsubishi Colt. To save money, they eschew all non-essentials.

“It is scary and, of course, we do have late-night thoughts of what will happen in the next few years,” says Tan. But while they are still free from the responsibilities of caring for ageing parents or children, she says it felt like the right time to take the plunge.

Job hunting abroad

On the other hand, there are those who are drawn to the hustle.

Seduced by the glitz and glam of New York City, An Lyn Chee decided to try her luck in the Big Apple in 2022. Then 23 and searching for a way to break into the fashion industry, the newly minted NUS Communications and Media Studies graduate wanted to follow in the footsteps of Rachel Green from the American sitcom Friends (1994 to 2004) and Andy Sachs from The Devil Wears Prada (2006).

“It just seemed like such an ideal life. And I thought, I never took a grad trip, I never went on exchange because of Covid-19, so I’m going to use the money I saved and put it into a three-month trip to New York City,” she says.

Never mind that she had neither a job offer nor a visa that allowed her to work in the US. Tapping her existing network — by that point, she had interned and freelanced as a fashion stylist in Singapore for magazines like The Singapore Women’s Weekly — she set up coffee chats and attended as many industry events as she could, all while applying for over 200 jobs in New York City.

“During those three months, I never said no to an opportunity or a meeting because you just never know if something’s going to lead you to another opportunity or if someone’s going to introduce you to someone else,” she recalls.

Sure enough, at one of these industry events, she caught the attention of the then-chief executive of designer brand Diane von Furstenberg, Gabby Hirata. Conscious that the two of them were the only Asian women in the room, Chee made sure to be the first person to raise her hand during the Q&A session.

Later, she reached out to Hirata again and pitched herself over a 30-minute phone call. “I think because she was originally from China and having made it in New York herself, she maybe saw a bit of herself in me doing what I was doing,” she says.

Convinced by her gumption and vision for the company, Hirata agreed to sponsor her J1-Trainee Visa and, in August 2022, Chee officially began work as a communications associate at Diane von Furstenberg.

She stayed in the role for a year before moving back to Singapore and eventually relocating to London in 2025, where she now works as a marketing and events specialist at jewellery brand Jessica McCormack.

Would she have been able to secure her New York job had she tried applying from Singapore? Chee does not think so.

“I really think your physical presence in the city helps a lot,” she says. “It shows your employer that you’re present, that you’re determined enough to get yourself here, that you can assimilate into a new environment and a new culture.”

Marketing specialist Pek was likewise told that it would be easier to find a job once she was based in Australia, the country she hoped to work in.

“I think that’s true,” she says. In her six years of applying for overseas jobs from Singapore, she was offered only one interview, which later fizzled out. Her job search in Melbourne, in contrast, yielded 30 interviews.

She says it was her varied experience in marketing that at last helped her clinch the role of social media, influencer and content manager at a local media agency. It paid her a similar salary to what she was earning in Singapore, though she estimates she lost a sizeable chunk of it (around 30 per cent) to taxes.

“If you have a local number, the company might think you have local experience or at least that you’ve had time to get the lay of the land better than someone who’s just applying from abroad,” she reckons.

At the end of the day, it depends on the country and type of work, says Felicia Romli, principal consultant of tech and transformation at recruitment agency Robert Walters Singapore.

For instance, an employer who needs to plug a manpower gap immediately – as a farm hand or waiter, for instance – might prioritise physical proximity over a specialised skill set.

In any case, she advises job seekers to familiarise themselves with the country they aspire to move to by researching the local job market, the types of roles available, as well as the political climate and immigration policies of that specific state.

Nicholas Sim, career adviser from the Centre for Future-ready Graduates at NUS, adds that students at local universities can build a firm foundation for themselves by seizing opportunities like overseas internships during their undergraduate studies.

“These experiences build global networks, enhance cultural exposure and provide practical insights into foreign work environments, enabling students to make more informed career decisions,” he says.

Easier said than done

While relocating before securing employment can make it easier to build professional networks and gain first-hand insight into the local job market, Sim warns that it comes with considerable financial risk.

London-based Wong knows first-hand how volatile and dispiriting the UK job market can be. “I don’t think I would have moved if I didn’t have savings,” she says.

At her busiest, she was working three jobs as a marketing coordinator for two start-ups and doubling as a receptionist at a yoga studio on weekends. She lost one of her jobs when funding for one company got pulled and had to quit the other start-up for personal reasons.

With her visa ending in July, she is now scouring for a position that will enable her to switch to a Skilled Worker Visa and thereby extend her stay in Britain.

“It’s super, super difficult. It’s hard even for citizens, and with the visa sponsorship you need, it just adds that extra layer of difficulty in finding a job,” she says. She has tried to be strategic about it, targeting jobs in the fintech space, and making sure the companies she contacts have the licence and funds to sponsor foreign employees.

“My visa is expiring and, for the first time in my life, I’m living pay cheque to pay cheque, so I think the combination of those factors is really putting pressure on me.”

Over in Japan, Foong, too, has yet to find a job that aligns with his needs. Since moving to Tokyo in December 2025, he has been biding his time studying for the Japanese language proficiency test, a qualification required by some companies.

So far, he has received a few job offers for English teaching positions, but hopes to find something with a salary comparable with what he was earning in his previous job at the Inland Revenue Authority of Singapore – ideally in the $3,500 to $5,000 monthly range.

At the same time, he is trying to be realistic about his prospects. “I knew I’d have to accept a pay cut moving to Japan. And I’m not really here to chase higher pay. I just want the lifestyle of living in a new environment,” he says.

Expectations versus reality

When he is not busy job hunting, Foong splits his time between illustrating – a hobby as well as side income stream — and hanging out with friends. “I actually have quite a lot of friends living here, so we’ll go to the gym together, or visit some bars and cafes,” he says.

With this support system cushioning his landing in a new country, he has had little trouble adjusting to life in Japan. He now lives in a 269 sq ft studio apartment that costs around $1,000 a month in rent, and saves money by cooking most meals and thrifting his clothes. “I haven’t really experienced any culture shock. I visited Japan quite a few times so when I moved here, it wasn’t as if I was moving to a completely new environment,” he relates.

Pek, on the other hand, has been shocked by the racism she encountered in Melbourne. She and her husband were spat on while walking along Princes Bridge and yelled at by passing drivers. Someone even threatened to punch her husband.

“My husband was really upset after these things happened. He felt like he wasn’t comfortable in his own skin because every time we went out, we had to be worried about these things happening,” she recalls.

The couple decided to call time on their Australian adventure in February, and have been travelling around Asia ever since, while looking for work in Singapore.

For Wong, too, living in London has been a sobering case of expectations versus reality. She flew to London with dreams of jet-setting to Rome and Paris on the weekends, but has yet to step foot on the Eurostar train after two years.

Between grocery shopping, job hunting and exploring her new neighbourhood of West Kensington, there simply was no time. “When you move, the new place just becomes your place, and you start to do whatever you were doing in Singapore someplace else,” she says. “It’s not going to be glamorous. It’s not going to be a holiday.”

She does not regret her time in the UK – she thoroughly enjoys London’s cosmopolitan character and cultural scene – but is still unsure if it has lived up to the ideal she constructed in her mind. “I was looking for more independence, and I guess in some sense, I’ve grown as a person and achieved some of my goals. But then again, I’m unemployed again, I didn’t do as many things as I wanted to do, and two years is actually really short,” she says.

But to Chee, whose New York City dream did come true, going all in on a one-way ticket is a risk worth taking. Her advice for those looking to take the leap of faith? Just go for it.

“It’s not easy and it can be scary, but you’ll feel more confident about yourself,” she says. “You’ll really feel like you can do anything.”

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