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What It's Really Like to Make Travelling Your Job - As Told By Cherie Sim

It’s probably every millennial’s dream to work while travelling the world. For @cheriesyw, not only is she living the dream, she’s helping people fulfill it too. Co-founder of Singapore’s very own travel publication, The Travel Intern (@thetravelintern), Cherie works with fellow co-founder and boyfriend, Hendric Tay of @pohtecktoes, to offer actual travel internship programmes. And it probably pays better than your coffee running, data entry, odd job internship.

From guiding interns to globetrotting to producing content, this power couple does it all themselves and somehow still managed to take an average of two trips a month. Last year, they spent more than 200 days out of Singapore!

Through travelling and setting up her own startup, she has gained more than a business and some travel photos. Cherie shared with us her experience as a traveller and entrepreneur.

Breaking comfort zones

Cherie tandem skydiving

It’s never easy to step out of our comfort zones, especially when we’re put in a foreign country where everything is unfamiliar. But Cherie and Hendric don’t want that to stop anyone.

“The Travel Intern started out for two purposes: 1) To make travel accessible to everyone, whether through information or inspiration 2) To put together a Singapore based travel community of content producers. We want to be that push for people to take things a little further, to try something they’ve never done and break out of their comfort zones. And travelling does that best.”

Creating memories

Cherie in ice cave

The best part about travelling is bringing back great stories with you. Even the not-so-pleasant events can turn out pretty hilarious in hindsight. For Cherie, she recalls getting the car stuck in thick snow while driving through Iceland.

“We had to get a tractor to rescue the car!” She laughs as she revisits the memory.

Cherie doing yoga

When asked about her favourite destination, she did not hesitate one bit. Rishikesh, a small little yoga city by the Ganga River, was where Cherie spent three months to complete 500 hours of the Yoga Teacher Training Course. (Yes, she’s also a certified yoga teacher!)

“It was where I had my first taste of India and actually see for myself that the world isn’t as dangerous as we think.”

Cherie dressed in Indian sari

But the best memories for her have nothing to do with a particular place.

“My most memorable trips are the ones where my beliefs are proven wrong, whether it's through talking to the locals, other travellers, or even by experiencing a place for myself. It’s about having that curiosity and open mindset, being ready to jump on opportunities for adventure.”

Going solo

Cherie in the mountains

Like all of us, Cherie needed a little push to travel solo for the first time. Her partner in work and crime made sure she got every bit of that.

“Hendric created a mystery trip for me. The only thing I knew was when I'd be flying and what weather to pack for. I only found out the destination at the airport. Turns out I was going to Cambodia! It was my first time travelling alone and I was worried about not knowing how to spend my time there. But soon, I went from worrying to wishing I had more time for the trip!”

Not a bed of roses

Cherie overlooking the sea

You might imagine working and travelling to be like kicking back in a hammock with a laptop while sipping a piña colado. But Cherie busts the myth by telling us about how they never really stop working on a trip. Unlike a vacation where you can rest anytime you want, they’re always producing content, whether when they’re out and about or back in the hotel.

“Sometimes when we're lacking of sleep, it's easy to fall into the mindset that it isn't enjoyable. But at the end of the trip, when we create deliverables that our readers find interesting and useful, and the clients are happy, it makes the effort worthwhile.”

Travelling and working as a couple

Cherie and Hendric doing yoga

Many times, couples fight when they travel or work together. For Cherie and Hendric, they have to learn ways to work around disagreements just like anyone else. And while she thinks they’re “no role models”, she attributes their chemistry to being independent and flexible.

“We disagree, we have our pet peeves and sometimes, we need time apart. But it gets better with every trip. We learnt what makes us tick and when we remind ourselves of the big picture – that ultimately we’re on the same page – it gets easier.”

Getting the right shoes

Cherie in Lucie Smooth Doe - Laos

One of the biggest struggles for Cherie is to pack in the lightest and most efficient way. She recommends using a backpack for Southeast Asian countries, as it’s great for getting around while keeping your belongings close to you.

“For backpacks, every item counts so having things that are duo purpose is a huge appeal! Shoes especially – definitely bring something that’s good for walking a lot while also looking presentable enough for the city.”

So we sent over a pair of Anothersole for her trip to Laos. Of course, we needed to hear what she thinks.

“It’s so comfortable and versatile with any outfit! Definitely great for a lot of walking, which is really the best way to get a feel of a new destination.”

Making travel meaningful

Cherie on a dangerous hike

Having travelled far and wide, Cherie has a piece of valuable advice to make travel meaningful. Instead of just putting yourself in a different country, she hopes to inspire people to take on a fulfilling journey.

“I don’t think anyone needs to be convinced to get out of Singapore for a quick break. But it’s really not just about getting on a plane and getting out of the country. To get a more fulfilling travel experience, pick destinations that would challenge you a little and push you out of your comfort zone. Take baby steps! You don’t have to quit your job to travel, even just four days alone in another city can do wonders.”

Cherie's first solo trip - Cambodia
May 17, 2017