How this Workawayer built his freelance career while travelling the world
At Workaway, we absolutely love getting to know you all, whether it’s meeting you on the road, at a Workaway trip or hearing about your adventures through e-mails and social media. We couldn’t be prouder to be involved with such an inspiring community of travellers, which is why we just have to share some of the stories you tell us!
Join me for a conversation with Chester, a young twenty-four year old from Singapore who’s maturity and humble personality are really impressive! He shared with me his journey so far around the world and why he values Workaway and connecting with locals so much. After spending some time in Japan and Australia, I caught up with him while he was in Vancouver to ask how he balances travelling, writing, and more. Here’s what he had to say!
Have you been doing Workaway the whole time or how did you find Workaway?
So I was intrigued and I asked them, “How do you do that?” Since then I’m hooked. Sometimes I use couchsurfing too. I don’t take a hostel anymore but it can still be a good back up option.
I do like hostels cause you get to meet lots of travellers, but it’s just an entirely different feeling when you’re travelling long-term! I know this feeling when I started wanting to build more substantial connection with the people that I meet. I think having a sense of purpose when you’re without roots makes your journey a lot more fulfilling.
I also found that when I’m always with a group of people from different countries, we get into our own bubble. We hang out together. We go places together. And eventually we end up always having the same comments about something that we experience together.
How did you choose to start doing what you’re doing? Since when did you really get into hiking? Is there a reason or a story behind it all?
Since then I just knew that I don’t actually want to work somewhere in an office 9am-5pm. All I wanted is just to get out there and not come home for a LONG time. I spoke to my boss about it and suggested freelancing and working remotely for him, but he wasn’t keen. At that point I decided to quit. About two years ago I left home and arrived in Australia, and that’s how I started to realise hiking is my passion!
Along the way a few months in my perspective and my worldview have expanded so much from all the different cultures I’ve experienced. I started thinking how travelling would really help my writing a lot and help me grow as a writer. This idea sort of stuck in my head and I just felt unstoppable.
No, it started from when I was in school. Writing always made me feel a lot better about myself and about what was going on in my life.
And so when I went home I would sit in front of the computer and write for hours and hours. I remember thinking about how I would eventually call myself a writer when I first started doing short stories. I tried to send them out and get them published and I eventually did. It was a small magazine, but for me it was something huge!
I started freelancing with a company and eventually after a while it got very difficult to maintain the relationship with my co-worker because I’m never there in person.
Back then there weren’t many platforms for amateur writers in Singapore to get heard and get noticed.I started this online magazine back home, and I tried to look for other writers to work with me. After half a year I managed to release the first issue with seven other writers, which has now became an online journal.
How do you decide where to travel? Is it geographical or does it depend on what opportunities come up?
Once I’m ready to move on I’ll be heading down to South America because I’ve always been really fascinated with the culture there. So apart from costs, the rest of the time I usually choose a place because of its culture or nature.
Yeah! Why not? I’ve been feeling this way for a while now.
Thanks so much for your time and sharing your stories! I hope you get to go on some more incredible hiking trips again soon.
I hope you get to go on many, many more travels.