For many, the length of an overseas trip is limited by how much annual leave they have. There’s no such limit for Jennifer Hong, however.
In fact, the 27-year-old didn’t return to Singapore for a whole year because she was busy travelling around Asia and documenting her journey via social media.
In December 2024, Jennifer told her friends that she would be embarking on an overland trip — a type of travel covering long distances and exploring relatively remote areas over a long period of time — from Singapore to Kazakhstan.
“All of them assumed I was just flying there, because the concept of slow, overland travel was very confusing to them,” she told AsiaOne in an interview on April 6.
“But once they started watching my vlogs and saw how I documented my trips, they understood what I was doing.”
Jennifer, who had been working for two years as a secretary at the health ministry while double-hatting at one of its statutory boards, quit her job that same month so that she could travel full-time.
What was supposed to be a five-month trip eventually turned into a year-long one, with her visiting a total of 11 countries.
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The young Singaporean shared that she left her full-time job due to a combination of factors, including burnout, stress, family issues, and job instability.
“All of it added up, and I knew that I needed a change of scenery,” she said.
She embarked on the overland trip on Dec 27, 2024, and returned to Singapore in February this year, just in time for Chinese New Year.
Now, Jennifer is taking a break from travelling to focus on caring for her grandmother, who suffered a bad fall.
But this isn’t the end for Jennifer, who plans to continue exploring the world full-time.
From Singapore to Georgia
When Jennifer first told her mother that she wanted to travel around Asia for several months, her mother was unfazed.
“My family is comfortable with me travelling alone because they know I’m independent,” Jennifer explained.
She later found out that her mother had even downloaded Instagram to follow her on the journey.
While she has travelled by herself ever since she was 17 — with the longest being a trip to Mongolia for 13 days in January 2024 — this was Jennifer’s first solo backpacking trip, so she gave herself five months to complete it.
“I’ve always enjoyed solo travel. I find real joy in it because I get to have unrushed mornings, plan my own itinerary, and meet nice people overseas,” she said.
Before embarking on the overland trip, Jennifer knew she didn’t want to just fly to one country and stay there for months.
After doing some research, she planned a point A-to-point B overland route with assistance from ChatGPT.
Besides helping to figure out which countries she could pass through, the AI chatbot also suggested Kazakhstan as the ending point of her trip, as she wouldn’t have to rush through her travels given the five-month timeframe.
Her itinerary initially covered seven countries — Malaysia, Thailand, Laos, China, Mongolia, Kyrgyzstan, and Kazakhstan.
Jennifer, however, reached her destination after only 114 days.
While that was supposed to mark the end of her journey, Jennifer didn’t want to stop there and extended her trip to include Tajikistan, Uzbekistan, Armenia, and Georgia.
“I felt a bit lazy to go back. But more than that, the people I met along the way kept hyping me up to continue,” she told us.
By the time she reached Kazakhstan, Jennifer felt that there was “still so much to see”.
She added: “I also realised I still had things to figure out in my life, and going home immediately wouldn’t have helped me gain that clarity. So I decided to keep travelling.”
For a while, Jennifer also contemplated extending the trip to Europe, especially since many of her social media followers encouraged it.
“But I was quite hesitant. Europe felt like a completely new territory to me since I’ve mostly travelled within Southeast and East Asia all my life. So I decided to set Georgia as my end point, explore it properly, and then fly back to Singapore.”
Jennifer also shared a quote with us: “If you get on the wrong train, get off at the first stop. The longer you stay, the more expensive it gets.”
It made her think of the risk of pushing her limits.
“I was worried that if I continued travelling to Europe and things got expensive, I might run out of money and struggle to get back home,” she said.
The young woman spent between two weeks and a month in each country, except for Armenia and Georgia, where she stayed for five days and three months, respectively.
While it’s hard for her to choose a favourite destination out of the 11 countries she visited, Jennifer said she had the most memories in Georgia.
“Georgia has a one-year free visa for Singaporeans. I was there in late August… I didn’t want to keep on going from country to country, so Georgia was my rest stop,” she said.
After concluding the overland trip, Jennifer flew to Xinjiang, China, and spent the end of 2025 there with a friend before flying back to Singapore in February.
Planning for a long trip
For those curious about how she funded the year-long trip, Jennifer said that the bulk of the money came from personal savings accumulated over years of work.
As she had built a social media presence documenting her travels on Instagram, the young Singaporean managed to land partnership opportunities with a few companies, which helped cover some of her transportation costs.
While she isn’t done tallying up all her expenses, Jennifer estimates that she spent about $20,000 on the entire trip, including accommodation, transportation, food, and daily necessities.
As a backpacker, Jennifer also had to be strategic about what she packed for one year of solo travel.
In her 50-litre backpack, she carried a down jacket, outer coat, long-sleeved tops, sportswear, hiking shoes and running shoes. She also had a pee funnel.
As for her 16-litre day bag, Jennifer packed other necessities such as wet wipes, a universal adaptor, her laptop and a Bluetooth speaker.
She also kept essential items close to her with a small sling bag containing her passport, wallet, extra phone, portable charger and water bottle.
In hindsight, she said that she could’ve packed less items.
And while she found the overland trip life-changing, Jennifer admitted there were moments when she felt homesick.
“This happened particularly when I was in colder countries and had to layer up every single day. It made me really appreciate Singapore’s all-year-round hot climate,” she told us.
Occasionally, she would also crave certain Singapore foods such as laksa.
Solo travelling: The good, bad and ugly
Over the past few months, Jennifer made plenty of great memories, both alone and with people she met along her journey.
One of her fondest memories was from her stay in Tajikistan, where she met a group of babushkas (grandmothers) while she was walking a long distance in the dark.
“They were sitting outside and staring at me. Later, they invited me to their house and offered me some of their traditional food.”
This wasn’t her first encounter with kind grandmothers, as Jennifer shared that she met several others who took care of her across her travels, especially in Georgia.
“The majority of my experiences were quite heartwarming,” she said.
“I hitchhiked quite a bit across Central Asia… Almost all the drivers I encountered were very respectful and generous. They would even stop to buy me food and drinks, their hospitality was remarkable.”
When she first tried hitchhiking, Jennifer felt embarrassed because she was standing by the roadside and expecting free rides from people. But she soon got the hang of it, and hitchhiking helped her save money on transportation in the long run.
“The downside of it is the danger. Sometimes, the drivers are not very nice,” she told us.
Jennifer shared an incident where she was sexually harassed by a melon truck driver in Tajikistan while making her way from Dushanbe to Khorog.
She was stuck in the vehicle with him for nearly 14 hours.
“My mistake was hitchhiking at around 7pm. I had spent the entire day looking for transportation out of the city because I wanted to go to another city called Khorog, which would take about seven to eight hours to reach by car,” she recounted.
Jennifer said she wasn’t able to find any information online about how to get there, and she couldn’t ask for help as there were no taxi drivers around.
So when the truck driver approached her and offered her a free ride to her destination, she jumped at the opportunity.
While his behaviour was normal at first, things took a turn for the worse after he started drinking.
“He started touching me while I was sleeping. He touched my breasts and I suddenly woke up. I asked him what he wanted and he was doing all sorts of hand gestures,” she shared.
Alarmed, Jennifer whipped out her camera to record what was happening.
“He knew I was taking videos of him, but he didn’t care,” she said.
Although Jennifer wanted to get out of the truck, she had other concerns — it was 2am and the vehicle was driving along a road near Afghanistan, close to a cordoned-off area. There were also no other cars in the vicinity.
In the end, she decided to move to the back of the truck where the melons were stored.
Later in the journey, a local woman from Tajikistan also asked to hitchhike with the same driver.
Jennifer took this opportunity to show her the video footage, warning her that he was up to no good.
Both women quickly got off the truck, and the local took Jennifer to a military base where a military car drove them to Khorog, Jennifer recounted.
Besides this incident, Jennifer also encountered racism and harassment during her travels.
“In Georgia, a few kids called me ‘ching chong’ and kept saying ‘Thai massage’,” she shared. Some taxi drivers in other countries would also call her ‘China’ to get her attention.
“There are quite a lot of memorable moments, but the less pleasant ones tend to stick with me more,” she told us.
But Jennifer learned how to deal with challenges like these.
The young Singaporean met other travellers who chose to detach from such situations, not giving attention to those who harass them, and she learnt to do something similar.
“I usually put on my earpiece and listen to calming music. Even if I’m aware of what’s happening around me, it helps me shift my focus and not engage with it,” she explained.
“I encourage people to do the same when they’re tired and overstimulated.”
‘Travelling helped me’
Apart from all the experiences she gained, Jennifer felt that she has become a better version of herself.
“Back when I was still in Singapore, I was always complaining,” she said. “When I started travelling and was alone, I was a totally different person and found myself complaining less and doing more.”
In the past, Jennifer would strictly adhere to her plans and itineraries while travelling. “But now, I’ve learned to let go a bit and just enjoy the moment,” she told us.
Travelling also helped her deal with one of the reasons why she left her job: Burnout.
“Burnout for me came from stress. It got to a point where it affected how I think… I was dealing with a lot of repetitive thoughts.”
“Travelling helped me step away from that environment. It gave me space to detach and reset. I wouldn’t say it ‘cured’ anything completely because when stress comes back, those patterns can still return,” shared Jennifer.
Slow travelling helped her to stay present in the moment, while being in new environments helped shift her focus away from what was going on in her head.
“I think it’s not just travel, sometimes just changing your environment can completely change your perspective,” she reflected.
As for the rest of 2026, Jennifer plans to travel, but she will go on shorter trips within Southeast Asia.
Next year, however, she hopes to embark on another long overland trip.
In the meantime, the young woman will not be looking for a full-time job as she intends to fund her travels through content creation as well as freelance and part-time work.
She also plans to travel on a budget to minimise spending.
“It’s difficult to go back to a nine-to-five job after an experience like this. It’s hard to put into words,” Jennifer told us.
For those considering going on a long solo trip, she has a piece of advice to share — don’t be too rigid with their plans or itinerary.
“Give yourself room to breathe, because there will be moments where you feel frustrated, even with yourself, and that’s quite normal,” she said.
“So be patient with yourself. And as you’re navigating new cultures and unfamiliar environments, take breaks when you need to. You don’t have to push yourself constantly.
“That’s the whole point [of solo travelling], you’re not reporting to anybody but yourself.”
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