At 26, this S’porean couple gave up their S$250K annual salary to travel the world

For most Singaporean couples in their late 20s, the next milestones after marriage often look predictable—BTO, promotions, and maybe, starting a family. But for Darien Tan and Joanna Wong, both 27, the script felt too familiar and too confining.

In 2024, the couple made a decision that would shock most: they walked away from their combined S$250,000 annual income, quit their jobs in tech, and set off to travel the world—indefinitely.

Since then, Darien and Joanna have lived in a variety of countries, including Indonesia, Europe, China, Japan, and they’re still on the road.

But how do they make it work? We spoke to the couple to find out how they made the leap, managed their finances, and what life on the road has been like.

They saved up S$200K to travel

Darien and Joanna first met in church when they were just 12 years old, and started dating at 16.

Seven years later, in 2021, the pair tied the knot. They then entered the corporate world, taking up stable 9-to-5 tech roles. But the routine soon began to weigh on them.

“We were comfortable but lived for the weekends and the occasional holiday. We were so work-focused [that] at one point our living room had no sofa, just desks,” said Joanna.

By 2022, the couple began “seriously planning” for a different kind of life: one centered on travel and freedom.

They set a target of S$100,000 in liquid savings, with a monthly budget of S$3,000 for living expenses abroad. Their mortgage could be covered entirely with CPF funds, so it was excluded from the cash budgeting.

A year later, they reached that goal, but decided to aim higher, targeting S$200,000 to extend their travel runway. To accelerate savings, they rented out rooms in their home and co-lived with housemates.

Looking back, Darien calls the extended target a “fallacy.” “When you ask anyone how much they need to be happy, it’s always double of what they have. We were at S$100,000 and thought we needed S$200,000,” he shared.

After hitting S$200,000 in savings, the couple felt that it was time to quit their jobs. “We were 25 turning 26 at that time… but it wasn’t easy to let go,” he said.

“We had both just gotten our promotions at work, and it felt like the opportunity cost was too huge to quit. After much deliberation, we decided that it was now or never.”

A near-death experience that same year cemented their conviction. During a company retreat in San Francisco, Darien was involved in a serious car accident on the way to the airport.

“The van we were in rolled at least five times,” he recalled in an interview with Business Insider. That moment was a “breaking point” for Darien—it made him realise how fragile life really is and how easily everything can change.

In Aug 2024, both Darien and Joanna handed in their resignation letters, and by Sept, they began living life on their own terms.

Making “radical decisions” together

When Darien and Joanna told their families they were quitting their well-paying tech jobs to travel the world, the reaction wasn’t one of shock—surprising, perhaps, in a society where many still believe there’s only one narrow path to success.

“Our parents are very supportive of the decisions we make, but not without reason,” said Joanna. “Since we were young, we’ve always made rather radical decisions together—ones that probably built our parents’ confidence in our ability to follow through with unconventional choices and make them work.”

Those choices span a long list. Joanna dropped out of junior college to pursue Child Psychology at Ngee Ann Polytechnic, while Darien turned down a full engineering scholarship at SUTD to study Business Administration at NUS instead. Together, they even started a baking company during their tertiary studies, running workshops for four years.

Eventually, life brought them to their tech careers—but the couple never lost their appetite for charting their own path.

“So, we didn’t think it came as a surprise to our families that we both wanted to quit our corporate jobs. I guess it never really felt like us in the first place to be in one.”

The couple began their travels in Bali, where they spent about three months recovering from years of corporate burnout. It was the first time they had truly disconnected from the Singapore grind.

“We allowed ourselves to completely switch off,” Joanna recalled. “We indulged in food, working out, going for physical therapy, sleep—and repeat.”

At first, they expected to feel completely fulfilled. After all, they were living what they once called their dream life. But as the weeks went by, an unexpected feeling surfaced.

“There was an emptiness looming inside of us,” Darien said. “As much as what we had was freedom, what we really wanted was purpose.”

That realisation led to a new goal: to document what it’s like to live life on their own terms—from a Singaporean perspective.

“There are many Westerners that you can follow on YouTube who decided to pursue the same lifestyle as us. But you will be hard-pressed to find a Singaporean couple who had actually quit their jobs together to pursue an alternative lifestyle and documented it.”

They wanted to pioneer what that looked like for others back home, so the couple started a YouTube channel documenting their lifestyle in late 2024. Since then, their channel has grown steadily, attracting a community of over 20,000 subscribers.

Funding their travels

Over the past year, Darien and Joanna have travelled to more than nine countries, including living out of a van in Japan and exploring remote parts of China. 

Finance has always been a “big topic” for the couple throughout their journey. “As two very practical Singaporeans, we’d always aimed to balance between living our dream lives and also financial prudence,” said Darien.  

Throughout their travels, the couple tries to stick to their S$3,000 monthly budget; however, expenses vary by location, with some months going over and others under. They balance it out over time to keep their overall spending on track.

For instance, in Jun, trips to the UK and Spain pushed their spending close to S$6,000. However, from Jan to May, they spent well under budget, averaging about S$1,800 per month.

Beyond savings, Darien and Joanna supplement their lifestyle with passive income streams. “We had to do things that most Singaporeans wouldn’t be comfortable doing,” he added.

The couple continues to rent out their HDB, which generates nearly S$5,000 per month. Meanwhile, their YouTube channel has also opened up additional opportunities.

Darien and Joanna’s YouTube income is split across three main streams. They started with travel content, earning as little as S$3 per day from ad revenue when posting a single video per month. Today, it contributes roughly an eighth of their social media-related income.

While creating travel content, they noticed that viewers were less interested in itineraries and more curious about personal finance. This insight led them to develop a financial toolkit for aspiring travellers, which now accounts for a quarter of their YouTube earnings.

Their remaining income comes from brand partnerships secured through their content. Together, these streams allow the couple to maintain their travels while sharing insights and inspiration with a growing audience.

Living life on their own terms

Currently, Darien and Joanna are residing in Hoi An, Vietnam. “Vietnam is a very charming place with exceptional local food. From a cost-of-living perspective, it’s a quarter of Singapore’s,” said Joanna.

They plan to continue travelling, but life on the road isn’t always idyllic. In Vietnam, severe flooding has disrupted daily life in recent weeks—some roads are submerged, and the couple occasionally has to cross them using small boats, like sampans.

There have also been times when they had no access to toilets or even clean water, such as during their stay in Raja Ampat, Indonesia. But for Darien and Joanna, that’s part of “the beauty of travelling.” “We get to experience a country for what it truly is,” they said. “We take situations lightly because no matter what happens, it’s not the end of the world after all.”

For the couple, success is no longer defined by promotions or paychecks. Their philosophy is to spend their money on doing the things they want to do in life rather than deferring it for a future moment that may never come. This mindset has guided both their travels and their approach to life on their own terms.

And they hope they can inspire others to make meaningful choices for themselves as well.

Featured Image Credit: Darien and Joanna