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How to work remotely and travel the world as a Digital Nomad

How to work remotely and travel the world as a Digital Nomad

I took a seat in a cute Lisbon cafe and opened up my laptop for a morning of freelance work.

It was going to be a hot day, so I was grateful for the air-conditioning that was keeping the shop cool. I promptly ordered an iced coffee with oat milk then ran through my emails before starting work on content for my client’s Instagram account.

This was the beginning of Rob and I’s daily ritual during our week-long stay in Lisbon. Our routine consisted of working from cafes each morning, then moving our laptops to the dining table of our Airbnb after lunch. Our evenings were spent wandering the streets to find an al fresco spot to have a Portuguese wine and dinner as the sun set.

On the weekend we did sightseeing activities around the city, including taking a train out to Sintra to marvel at the bright colours of Pena Palace, and stopping in at adorable coffee shops to eat as many Pastel de Nata (Portuguese tarts) as we could justify.

As a freelance Travel Writer, Content Manager, and Social Media Manager, I’m able to work from anywhere – all I need is my laptop and an internet connection. I absolutely love how flexible my work is, and how I can take it with me anywhere.

If you’re also interested in this Digital Nomad lifestyle, here’s some insights into my experience working remotely and a few tips on how you can set yourself up as a Digital Nomad.

Pastel de Nata, Lisbon, Portugal

Ordering coffee and Portuguese tarts while working remotely in Lisbon, 2018

What does being a Digital Nomad really mean?

You’ve probably heard the term ‘Digital Nomad’ before, but some of you might be unsure of what it actually means. Here’s the deal: You work from your laptop, and you do it from a place that isn’t an office: sitting poolside at a resort in Thailand, from a hotel lobby in Mexico, or from a cafe in Portugal.

I wouldn’t really consider Rob and I to be Digital Nomads as we use Sydney as our home base and don’t work abroad full-time, but we easily could if we wanted to. Instead, we work remotely in shorter stints to extend our trips and travel more often.

This wasn’t the only time that we had worked remotely on a trip. First, it was 3 weeks of freelancing in Barbados while we waited for our US visas to come through in 2015. Then it was a week and a half in Dublin during another last-minute visa trip in 2017. We enjoyed it so much that we planned a week of remote work in Brisbane a few months later, followed by Lisbon in 2018.

What is it like to be a Digital Nomad?

Working remotely as a Digital Nomad can be a wonderful experience. It’s a great way to see more of the world on a budget and leave behind those nasty expenses that come from living in one place, like rent and bills. You can essentially continue travelling forever (hell yeah!) and it shouldn’t get exhausting because you’ll be travelling at a slower pace than you normally would.

On the other hand, being a Digital Nomad does have downsides. Loneliness is often a problem, as you may not stay in one place long enough to make friends. It’s also possible that you’ll have to travel home often to attend important events – I had a death in the family during my time living abroad, and being so far from my family during this time was a hard thing to manage.

Barbados beach

Enjoying weekends at the beach while working remotely in Barbados, 2015

How do you become a Digital Nomad?

Working remotely is not something that is easily accessible for everyone, and in some situations, it’s near impossible. For example, working as a salesperson in a store or working in IT where you’re fixing people’s computers are both jobs that don’t translate to remote work.

If you’re in one of these fields, don’t worry – the trick is to transfer your skills to a job that can be done remotely. And if you don’t enjoy your current job, try something new! That’s what I did when I started Travel Writing.

The reason that Rob and I are able to work remotely in our jobs is not just by luck – it’s because both of us have spent years building our careers to the point where we can take them abroad. I spent a long time working towards becoming a freelancer as I can’t stand office jobs, and as a result, I’m now able to work remotely from my laptop managing my clients social media accounts and writing travel articles for blogs and online publications.

Rob spent 2 years working as a Software Developer at a high-profile company in New York, which meant that he had enough experience to successfully apply for a remote role afterwards (they can be pretty hard to get as there’s a lot of competition). He now works for an American company that is entirely remote – their employees are based all over the world.

Which countries are good for Digital Nomads?

If you’re looking to become a Digital Nomad long-term, then the best options are countries which are fairly cheap to live in. This way, there won’t be as much pressure to make loads of money to cover your expenses.

My previous experiences have only involved shorter stays in popular cities, but if I were to choose somewhere to work for a few months, I would probably go for somewhere like Colombia or Thailand. These countries are popular with expats due to their low cost of living. For some more options, check out the cities on Nomad List.

Dublin, Ireland

Spending evenings drinking Guinness while working remotely in Dublin, 2017

How do you manage your work schedule?

Rob and I try to set up our work schedules so that our weekdays somewhat reflect a regular full-time job, then we spend our evenings and weekends sightseeing, eating out, and exploring.

This means that we need to spend a lot longer in each place that we visit, as most of our time is tied up with work. So we might spend 1-2 weeks in a destination, instead of just 3-4 days as we normally would if we weren’t working. It feels a little more like we’re temporarily living in the city, instead of visiting it just to sightsee.

What are some tips for Digital Nomad wannabes?

  • If you don’t have a job that allows you to work remotely, work towards getting one. I did it through becoming a freelancer, but you can also look into other ways of making travel your career.
  • Join online communities for remote workers and digital nomads. I’m a member of some Facebook groups that share job opportunities and host discussions about working remotely. Start with Guavabean or Remote & Travel Jobs.
  • Don’t expect it to happen quickly as this is something that you will probably need to plan far in advance. If you want to become a Digital Nomad in 12 months time – great! Set some goals for getting yourself a remote job, and start taking steps towards making it happen.
  • Hustle like you’ve never hustled before. Things won’t just fall into place without some hard work and a solid plan – making your dream a reality takes time and effort! If things go wrong on your quest, don’t give up. You’ll make it there eventually.

Got any questions about working remotely or becoming a Digital Nomad? Share them in the comments and I’ll do my best to answer!

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6 Responses to “How to work remotely and travel the world as a Digital Nomad”

    • Ashlea Wheeler

      Thanks Charmaine! Why don’t you think you’d be able to do it? I’d love to know what your thoughts are on the digital nomad lifestyle.

  1. Kristen

    I love the intro to this post…makes me want to be in a Lisbon cafe right now! It sounds like you guys have a really great routine set up while working remotely. One of the best things about being a digital nomad is being able to set your own schedule, but I like to mimic regular work days, too. Spending mornings at a cafe and afternoons at the kitchen table feels productive and keeps you from sitting for hours in one spot all day. Thanks for the great post!

    • Ashlea Wheeler

      Thanks for your comment, Kristen! I agree – mimicking regular work days is essential to getting work done while travelling as a digital nomad. I’m so glad you’ve been able to make this lifestyle work for you 🙂

  2. C. Randen

    Great article and advice! I really enjoy getting a peak behind the working nomad curtain. While you travel bloggers do a great job of making your lives look amazing, it is nice to know about the work that is put in to enjoy the great lifestyle. Thank you!

    • Ashlea Wheeler

      I’m so glad you find my story intriguing! It’s definitely hard to know what happens behind the scenes from an outsider’s perspective. I hope I’ve been able to reveal a bit of what remote work is really like!


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