Shentonista Features: New Extremes — Ready, Jet Set, Go


Tobby & Kaiyi

Have you ever wanted to drop everything to go travel the world? Though it sounds like a far-fetched dream for many, for one couple, that dream has become a palpable reality. Meet Tobby and Kaiyi—a former financial analyst and UX designer respectively, who have put their lives in Singapore on hold to explore as much of the world as they possibly can on a budget.

Needless to say, we knew we had to get in touch with them to find out just how they managed to make this happen, or if only to live vicariously through their travels. When we reached out, however, they were well into their next adventure, having just arrived in Mexico after backpacking in Japan. Well, thank goodness for the internet—with a 14-hour time difference and 16,596 kilometres between us, we dialled into a video call early in the day, just as Tobby and Kaiyi were winding down for the night in their Airbnb apartment.

Like many of us, Tobby and Kaiyi had always enjoyed the occasional overseas trip. And like many of us, back when they held 9-to-5 jobs, that meant working around a limited number of leave days per year and only visiting common tourist destinations. That all changed in 2012 when they travelled together for the first time, on a short getaway to Krabi, Thailand. “That trip with Tobby made me discover a new way of travelling,” Kaiyi tells us. “Previously, when I traveled with friends and family, we’d always stick to a fixed itinerary and never really ventured beyond that,” she says. “But in Krabi, we rented a scooter in the spur of the moment and just went exploring. We didn’t even have Google Maps yet back then!”

Once their wanderlust was ignited, its spark only grew brighter with time. “Every trip after that just became more exciting, and we wanted to go away for longer each time,” Tobby adds, sharing about their breakthrough trip to Taiwan, where they stayed for a month. “It was the longest trip we’d been on at the time. I had to plead with my boss to let me go on a sabbatical, which almost cost me my job!” Kaiyi recalls, laughing.


Subsequently, as Tobby and Kaiyi got used to longer and more spontaneous travels, they started imagining a life where they could fully prioritise their love for travel. But life happened, and six years passed—the couple got married and bought a house of their own, all while working tirelessly in their respective careers. By 2019 and freshly in their 30s, they were ticking off all the right boxes in the average Singaporean life plan. Still, their bucket list remained untouched, and the urge to pack up a suitcase and hop on a plane lingered at the back of their minds.

“That same year, I managed to convince Tobby that it was a good idea and we eventually decided it was time to take a leap of faith,” she says.

And just like that, they quit their jobs and booked a one-way flight to China for an unforgettable six-month voyage, with the goal of embarking on the Trans-Siberian Railway, aka the Transsib—the longest railway line in the world, stretching across two continents.

It was on this trip that they learned (the hard way) that it’s not always sunshine and rainbows when it comes to travelling. As they moved on from China, before boarding the Transsib, Tobby and Kaiyi found themselves spending a fortnight out in the elements of the Mongolian springtime, on what we imagine to be an arduous side quest that turned out to be the most challenging leg of their whole trip.

“As typical Singaporeans, we think that spring means nice weather right?” Tobby asks. “Wrong! It’s actually the most treacherous season in the area due to unstable weather conditions. We experienced both a sand- and snowstorm in the span of 13 days!”

For Kaiyi, it was the loss of everyday conveniences that she found the hardest to acclimatise to. “We stayed in a traditional tent, called a yurt, which had no electricity or running water, and just a car battery strong enough to power a lightbulb. Worst of all, we couldn’t wash ourselves. I think we might’ve gone without showering for eight days straight!” she exclaims. To say that Tobby and Kaiyi were hoisted out of their comfort zone is an understatement, but thankfully they had each other to rely on.


In fact, it was their strong connection that brought them together in the first place. Even through a computer screen, we could feel a sense of warmth as they exchanged slight jabs, banters, and hearty laughs with each other. When asked how they met, the pair erupted into sheepish giggles. “My friend was trying to set me up with someone, and Tobby happened to be at the gathering too. I ended up talking to him a lot more throughout the meeting because we had so much in common,” Kaiyi explains.

Back on the Transsib, the rest of the trip was rather smooth-sailing, but no less memorable. The pair made their way through Russia and Eastern Europe over the next few months, making a final stop in Turkey before returning home.

After what we can only describe as an adventure of a lifetime, all Tobby and Kaiyi could think of and talk about since they touched down was an even bigger adventure. This time, with a wealth of experience, a greater resolve, and a whole other region in mind, it was only four years before they set out on a journey yet again at the end of 2023. “Deciding to leave our jobs for the first time was tough, but by the second time, we were prepared to leave once we’d saved enough for our next trip,” says Tobby. The pair had also downsized their apartment at this point, and has been renting it out to generate passive income—a safety net that gives them great assurance while travelling full-time.


Now a third of the way into their year-long trip (or until their budget runs out) and advancing towards South America, they’ve still got plenty of sights and sounds to experience ahead of them. To help stretch their dollars and add value to their time abroad, Tobby and Kaiyi have been volunteering odd jobs in exchange for food and accommodation, particularly in the familiar territories of Japan, where they spent the first three months. Recounting stories about their time farming vegetables, participating in traditional mochi-making, and even clearing out an abandoned house through Japan’s rigorous recycling system, the couple summed up the experience in one word—transformative.

“In a way, volunteering made me feel very small because of the realisation that the world is so big and there’s just so much out there that we don’t know. But at the same time, we got to learn many things that would never have crossed our minds living in Singapore,” says Kaiyi. “We hope to do more volunteering throughout the rest of our trip as we’d never be able to have such experiences as normal tourists.”


The couple’s travel style is bold for sure, but don’t misconstrue their spontaneity for impulsivity and foolishness. On this matter, Tobby tells us, “Many of my friends say that we’re so daring to be doing this, and while I agree, most people don’t see the careful planning that goes into each trip. We only truly considered long-term travelling after we’d settled our housing mortgage and cleared our debts so that we don’t leave with everything and go home to nothing.”

So what exactly is the key to becoming avid travellers? Perhaps it’s Tobby’s big picture thinking and research skills, Kaiyi’s way with numbers and attention to detail, or a little bit of both that have allowed them to budget for further and longer trips. In short, it’s practising frugality. That may not sound too enticing, but the couple believes that it all comes down to maximising experiences while minimising expenses to be able to travel comfortably without lugging around heavy financial baggages.

Aside from being smart with their finances, Tobby and Kaiyi also put many steps in place to ensure that they stay safe and comfortable no matter where they are in the world. If you’re curious to learn more about the ins and outs of their travels, they run a blog and social media platforms, under the alias Frugal Explorers Club, where they share what they’re up to each day, beautiful travel images, a budget breakdown of their trip, as well as lessons they learn on the go.


While they’re no doubt the envy of many peers, Tobby and Kaiyi also acknowledge that their spontaneous way of travelling is not for everyone. Some even call it outright extreme! “We’ve had people comment that we’re ‘so poor thing, go travelling just to eat bread everyday’ or ask us ‘travel for a whole year not sian (tiresome) meh?’ Kaiyi says, laughing. For them, that’s all the more reason to share their experiences to equip others with the know-how to curate memorable travels of their own.

As our call drew to a close, we wanted to know what’s next for Tobby and Kaiyi. An even bigger trip, perhaps? “The ultimate goal for us is to live abroad long-term,” shares Kaiyi. “We haven’t decided where just yet, so I guess you can say that we’re using our travels as a way to test the waters and weigh our options.”

“Our top choices were Japan and New Zealand, but after staying in Japan for awhile, we feel it might be a challenging place for us to reside in,” Tobby adds. “Still, we’re keeping an open mind for the rest of our route this year and planning to go for an extended trip to New Zealand in the future, so we’ll see where the world takes us!”

For now, they’ll continue to learn more about the world, see the wonders of mother nature, and try all the delicacies there are to try. As for us, we spent the rest of our morning daydreaming about far-off places and our next vacation.

Frugal Explorers Club
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