Solo travel? And on top of that, getting lessons from solo travelling? That was something that I had never dreamt of before. When I exited my business in 2017/18, I didn’t know where my life would lead. In fact, I didn’t even know that I would still be continuing to learn about business, despite no longer running a business. The business lessons learnt were different and impacted me a lot more than when I was running my business though. Here’s how it all started.
The first thing that I had to face when I exited my business was that I suddenly found myself with a huge void in my life, especially since I spent almost every day working on my business in the past. With my release from my work responsibilities, I decided that I would go travel and see the world properly, which was something that I never had the time to do in the past.
Strangely enough, however, even after making the decision, I still felt encumbered. It was a very strange stifling feeling. I knew that I was definitely able to take the time to travel but yet felt like I had all these ties and commitments still.
I figured that I needed to reset my life, and so I had the sudden decision to go on a purge. The idea struck me one moment, and I decided to embrace it fully. In my mind, purging was a great concept because it could allow me to start from absolutely nothing again – a blank slate. That was the best way that I felt I could make any future decisions without any feelings of existing responsibility or commitment.
In the next few weeks, I sold and got rid of everything that I owned, which included my car, apartment, and most of my possessions. It was scary at first to let go of all these items but it slowly turned into a sense of liberation. It felt good because with every item I let go of, it was one item less of what I thought defined me. It freed me and I felt like I could start on a new slate. I had become a minimalist, and with my greatly reduced possessions, I finally felt ready to go on to travel the world.
Planning A Solo Travel Itinerary
Figuring out where to go was difficult, especially since this was the first time that I was travelling solo. I was hit with decision paralysis because of the sheer options that were available to me. I decided to break down the problem and look at it with just a few simple goals: to travel to where I wanted to do activities such as snowboarding and to visit my friends. This made the problem much easier to work on, and I found that I could more easily work a solo travel itinerary around this.
By piecing together all these trips, this became my schedule:
Nov 08 to Nov 18 Ulaanbaatar
Nov 18 to Nov 20 Hong Kong
Nov 21 to Nov 23 Macau
Nov 23 to Nov 25 Shenzhen
Nov 25 to Nov 27 Huizhou
Nov 27 to Nov 28 Hangzhou
Nov 28 to Dec 01 Shanghai
Dec 01 to Dec 17 Singapore
Dec 18 to Jan 23 California
Jan 24 to Mar 02 Niseko
Mar 03 to Mar 13 Singapore
Mar 15 to Apr 09 New York City
Apr 09 to Apr 21 Los Angeles
Apr 21 to Apr 30 Edinburgh
Apr 30 to May 16 Wroclaw
May 16 to May 19 Oslo
May 19 to May 28 Wroclaw
May 28 to Jun 02 Lisbon
Jun 02 to Jun 07 Barcelona
Jun 07 to Jun 08 Frankfurt
Jun 08 to Jun 09 Cologne
Jun 09 to Jun 10 Mainz
Jun 10 to Jun 12 Frankfurt
Jun 12 to Jun 17 Leiden
Jun 18 to Jun 24 Taipei
Jun 24 to Jul 06 Singapore
Jul 07 to Jul 09 Penang
Jul 09 to Jul 10 Singapore
Jul 11 to Jul 15 Canggu
Jul 15 to Jul 17 Singapore
Jul 18 to Jul 20 Adelaide
Jul 20 to Jul 27 Melbourne
Jul 27 to Sep 21 Queenstown
Sep 21 to Sep 25 Auckland
Sep 26 to Sep 30 Singapore
Oct 01 to Oct 03 Kuala Lumpur
Oct 03 to Oct 25 Singapore
Oct 25 to Oct 31 Canggu
Nov 01 to Nov 16 Singapore
Nov 16 to Nov 19 Beijing
Nov 19 to Nov 22 Foshan
Nov 22 to Nov 25 Phan Rang
Nov 26 to Nov 27 Ho Chi Minh
Nov 27 to Dec 05 Singapore
Dec 05 to Dec 10 Bangkok
Dec 21 to Dec 25 Danang
Dec 24 to Dec 25 Hoi An
Jan 06 to Jan 10 Kuala Lumpur
Jan 10 to Jan 13 Bangkok
Jan 16 to Jan 18 Tokyo
Jan 18 to Feb 29 Hakuba
I still considered Singapore my home. I’d travel for months at a time before I returned to Singapore though, typically to tend to bills and errands and get items that I needed for the next part of my trip.
What Did I Do When I Was Travelling Solo?
Depending on where I was, I had different things that I focused on. When I was in California, I spent time with a buddy of mine and his family whom I hadn’t seen in years because of the distance and the lack of time.
When I wasn’t spending time with them, I had rented a car and so I drove around to different parks and mountains. I loved the views and being in nature, especially since Singapore was such a concrete jungle. The rest of the time I would be going around to different cafes, where I’d read or write articles for my blog.
When I went to Japan in winter, I spent everyday snowboarding. Life then took on a much different focus. The day would be spent on the slopes, and in the evenings it would be a simple dinner and the days would repeat. Almost every day had new friends that I met and could hang out with. I thought time would pass slowly, but the 5 weeks that I spent in Japan disappeared in a blink of an eye.
I also wanted to do a road trip, and so decided on Scotland, especially since I had a friend there. My friend and I rented a little compact Toyota and spent 2 weeks exploring northern Scotland. It was amazing being right in the midst of the awe-inspiring castles, mountains, and rivers of Scotland.
I also did other things, such as pursue my snowboard instructor certification, tried fine dining at a top-ranked restaurant, drive on the autobahn, did a road trip in a camper van, lived out of a farm, and spent a week living with Mongolian nomads. These were both experiences that I cherished and the journey also provided me with several business lessons learnt, which I’ll cover below.
After a while though, I started appreciating slow travel a lot more. One of the best times of my travelling experiment was when I was in Wroclaw, Poland. I stayed in an AirBnB apartment, and spent my days going to the gym, shopping at the local supermarket, cooking most of my meals, hanging out with friends in the evenings, and working on myself. The fact that I was in a location for a month gave me the time needed to think and reflect, and I discovered a lot of things about myself then, especially with the lessons from solo travelling that I had.
Where Did I Stay When I Was Travelling?
While travelling, I stayed in all kinds of accommodations. I stayed in:
- Hostels (mixed dormitory)
- Hostels (private room, ensuite bathroom and toilet)
- Hotels (1/2/3/4/5-star)
- Camper vans
- Friends’ places
One of the lessons from solo travelling that I had was the change in my accommodation preference. When I was doing business and having holidays in the past, I preferred hotels and luxury. After travelling solo, I learnt that my favourite kind of accommodation were hostel dormitories. Because of the communal aspect, they allow me to meet new friends and it was incredibly social, which was great when I was by myself and had a few days in a new country.
I found everyone at hostels to be extremely friendly and welcoming. If you could smile and say hi, you could make new friends.
Lessons From Solo Travelling
Being able to travel this way is a great gift, and I had several business lessons from solo travelling.
Business Lessons Learnt: Simplification Is Key
One of my greatest business lessons from solo travelling around the world that I learnt was that you don’t need a lot. When you’re halfway around the world, you don’t want an apartment lease in your home country because that means you’re paying for 2 places every day. You also don’t want to be lugging big suitcases around the cobblestone streets of Edinburgh or the congested roads of Bali. That means you have to really focus on bringing only what’s essential.
When you are forced to remove what you previously thought was necessary, and then still thrive after that, it becomes a sobering wake-up call. I was actually unnecessarily burdening myself with additional stress and cognitive load without actually becoming better as a result of it. In fact, I was actually encumbered.
That was the greatest reason why I identified with and became a minimalist. It reminds me of when I started and scaled up my business and how one of the things that we absolutely prioritised was to be lean and nimble. That allowed us to run circles around the incumbents and gain market share. You can’t win against a 400-pound gorilla in a head-on fight if you’re a newborn gorilla. However, if you’re lean and nimble, you can gain experience and get the food that you need without alarming the 400-pound gorilla, and suddenly, you’d grow to be bigger and stronger than he was.
Business Lessons From Solo Travelling: Ruthlessly trim the fat. Keep things simple. Be lean and hungry. Simplify, not complicate. That’s how you really grow.
Business Lessons Learnt: Sacrifices Are Needed For Your Vision
All this travelling spanned about a year, and it’s very possible that I could also spend 5 years or even a lifetime doing this in perpetuity. It all boiled down on what I felt was more important to me, and what I was prepared to sacrifice and compromise on. Like almost anything in life, everything happens on a sliding scale and ultimately the choice that we make also incorporates the sacrifices that are built into those choices.
In the case of travelling, I found that the time that I spent travelling gave me great perspective and experience, but it took away the ability for me to set down roots. Friendships and relationships become very transient because I was only around physically for a certain amount of time. I missed events such as birthdays and weddings. While I expanded my ability to meet many people, it is much harder for me to get the chance to develop something deeper.
It reminded me of when I chose to be an entrepreneur in 2002. It was a choice that required sacrifices. I had to give up most of my social events, spend less time on my relationships with friends and family, and pare down on my hobbies and entertainment. In return, I could dedicate most of my time and attention to my business.
Business Lessons From Solo Travelling: Not only do you need to know what your vision and dream are, but you also have to be prepared for the sacrifices necessary to bring it to fruition.
Business Lessons Learnt: Your Focus Can Change Your Behaviour
When I was in my home country of Singapore, I realised that I was living with certain assumptions and perspectives. Without being aware of it, I also let society and people’s expectations affect and mold the way I thought. This meant that I always had a certain way of behaving that stemmed from what was acceptable by society and from people who knew me.
The peculiar thing was that when I left my home country, I had none of these binding me anymore. These lessons from solo travelling showed me that what I had thought was truth was just an assumption, and that I could be free to express myself.
In fact, when I realised this, I slowly became aware that it was even possible to experiment with new personality traits that I had not thought of displaying before. For instance, I was typically more reserved in Singapore, but while travelling and living a life outside of Singapore, I could experiment with being much more out-going and expressive.
It made me realise that if this is true, then we are completely able to shape who we are if we spend time and effort into developing the traits that we want to see from ourselves. With deliberate and progressive practice, these traits would slowly become ingrained and natural to our identities.
If you have thought that you needed to be more outspoken or less judgemental or more empathetic or less shy — the good news is that you can. One way to do it is to force yourself to do the things that you would otherwise not have done, but in a progressive manner because it’s unnatural and absolutely scary. Start with really simple and basic steps to test and see how it feels, and then build the desired behaviour from there.
Business Lessons From Solo Travelling: You can be who you want to be if you deliberately commit to practising the traits that you want to see from yourself.
Business Lessons Learnt: Understanding Your Target Market
I remember waking up in Manhattan on a Sunday with the whole day ahead of me, with nothing planned. I was thinking about activities to fill my day with and the first thing I thought about was to visit an attraction. There were tonnes in Manhattan: the Statue of Liberty, MOMA, Chelsea Market, etc.
Then I caught myself because I realised that I wasn’t feeling particularly excited at all, so I asked myself why I was even wanting to visit an attraction. That was when I realised I was only planning to visit an attraction because they were popular places to visit, and not because I actually wanted to visit them.
In fact, I had a much happier time when I went to a craft beer taproom, hung out there and started having conversations with people I met there.
Of all the lessons from solo travelling that I learnt, this was the greatest lesson and revelation for me: It turns out that doing what is popular isn’t what you have to subscribe to. And what is popular isn’t necessarily what you would want. And that’s something that I found to be true in many cases. In fact, when I travelled and heard the perspectives that others had, I realised that there are so many different groups of people who were passionate about so many different things.
When I was behind a computer, it was hard to imagine my target market or target demographic. I had forgotten it, but while we’re all different, we’re all human beings with pains, fears, dreams, problems, likes, and dislikes. When you truly understand your target market, your message to them can become so much more clear and specific.
Business Lessons From Solo Travelling: Understand your target market and target demographic really well. If you can speak to this market authentically, you can form a real connection with them when you’re growing your business.