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I Left My Stable Job In Singapore To Backpack Solo For A Year

From the outside, I had what many people dreamed of: a government job in Singapore, a steady income and a fairly predictable future. But behind the scenes, I was burnt out and kept wondering, “Is this really what I want to be doing for the next 10 or 20 years?” I'd always wanted to travel long-term and experience cultures completely different from my own. So, when my contract was coming to an end after 2.5 years of working there, I decided not to renew it and started planning a solo trip across Asia.Stepping outside my comfort zoneWhen I told my friends and family about my plans, they thought I was simply flying to Kazakhstan and staying there for a few months. It wasn't until I started posting daily “Singapore to Kazakhstan” travel vlogs that they realised I was making the journey entirely overland, on my own, without taking a single flight.One of the main reasons I chose this route was to make my budget go further. Flying from Singapore to Kazakhstan alone would have eaten up half of what I had set aside for the trip. But slow travel turned out to be about more than saving money. It allowed me to immerse myself in local cultures, connect with people, have meaningful conversations, and form genuine friendships along the way.I travelled by car, bus and train, and occasionally hitchhiked. Taking the overland route allowed me to explore 11 countries – Malaysia, Thailand, Laos, China, Mongolia, Kyrgyzstan, Kazakhstan, Uzbekistan, Tajikistan, Georgia, and Armenia – instead of the seven I had originally planned.What started as a five-month trip with a budget of SGD10,000 eventually grew into a year-long adventure that cost SGD18,000. Since I hardly shop when I travel, most of that went towards transport, food and accommodation.Solo backpacking lesson 1: My attempts to budget didn’t always go according to planOne thing I learnt pretty quickly was that the cheapest option doesn’t always give you the best value. I've booked cheap guesthouses only to realise they were so far from town that I'd end up spending more on transport.I also tried buying groceries to save money, only to discover that my cooking wasn't very good. I'd finish eating and still crave something better, then end up eating out anyway. Needless to say, I've stopped cooking regularly when I travel.I still try to stretch my budget, but I'm no longer as fixated on choosing the cheapest option every time. Sometimes, paying a little more upfront saves money, time and unnecessary frustration later.Solo backpacking lesson 2: Staying safe on the roadTravelling taught me that there are certain things I’m not willing to compromise on, even when I'm on a budget. For me, one of them is paying more for a private room, especially when travelling alone.Hitchhiking definitely helped me keep costs down, and some of my most memorable encounters were with people who gave me rides across Central Asia. That said, I wouldn't recommend it as something every solo female traveller should try. It comes with risks, and everyone has different circumstances and comfort levels.I learnt this the hard way in Tajikistan.I had been waiting for transport since afternoon but couldn’t find a ride. The only taxi available quoted me USD500, which is an outrageously high fare. Unwilling to pay that much, I decided to hitchhike instead.Looking back, it was a bad decision. By then, it was already 7pm. I was exhausted, my judgement was clouded, and all I wanted was to reach Khorog as quickly as possible.Eventually, a truck carrying melons pulled over, and I climbed in. I suspected the driver was drunk. Halfway through the journey, he tried to make his move on me. We were travelling along the Pamir Highway, near the Afghan border. I decided I would rather stay in the truck than get out in the middle of nowhere, especially since there were unlikely to be other vehicles passing by that could help, at that hour. Eventually, I climbed into the back of the truck and spent the night sleeping on top of the melons.While I still think USD500 was an absurd price for a taxi ride, if I ever found myself in a similar situation again, I’d look for a marshrutka (a shared minibus that typically follows a fixed route), or see if I could find other travellers to split a taxi with. I’d also arrange my transport earlier in the day and avoid hitchhiking at night.​My perspective on life has shifted sinceI thought returning to Singapore would feel like picking up where I'd left off. Instead, I found myself looking at my old life a little differently. After experiencing so much freedom on the road, the thought of returning to a traditional 9-to-5 felt different.Since returning, I haven’t immediately jumped into a full-time job. Instead, I’ve been working part-time while helping to care for my grandma. This gives me more time with my family while allowing me to rebuild my savings and plan for my next trip. This time, I’m planning to travel overland from Turkey to Morocco.Travelling also opened my eyes to different ways of earning a living. Around September last year, brands started reaching out to me for collaborations. Before that, I honestly didn't think it was possible to make money from vlogging or brand partnerships.Ultimately, I'd love to work overseas one day and experience what the work culture and lifestyle are like in another country.I am rethinking what financial freedom meansBefore I left Singapore, I associated financial security with having a stable job, earning a steady income and building up my savings. Don’t get me wrong – I still value those things.But after a year of travelling, I began to see money differently. It's not just about having enough to feel secure; it's also about having choices. Where I go, how long I stay, what kind of work I do, and how I want my life to look. Now, I no longer accumulate money for the sake of feeling secure. I also want it to support the kind of life I actually want to live.I don't think everyone needs to quit their job and travel for a year. But I also don't want to spend my whole life working and postponing the things that matter to me.Someone once told me, “You can always earn the money back,” and I agree. Of course, that doesn't mean spending recklessly without thinking about the consequences. For me, it's about knowing what I can afford, being responsible with my money, and finding a balance between enjoying life now and preparing for the future.​This article is part of TSS Confessions, a weekly column where we delve into personal finance topics that are unscripted and real accounts from people.Jennifer Hong is a content creator who shares her solo backpacking adventures and travel experiences. Follow her on Instagram and Facebook here.