How to Work Remotely and Travel

Sunday, May 27, 2018

When I first decided to ditch my day job to work remotely and travel as a freelance writer, everyone in my life thought I was a little crazy. Hell, even I thought I was a bit crazy. 

After all, I was leaving the security of my former life as a corporate attorney (and all of the snazzy benefits it came with) to be my own boss and write on a full-time basis.

I was willingly surrendering everything I had thought I’d wanted since I was eleven in pursuit of a livelihood that allowed me to have a life; a lifestyle that afforded me the freedom to pursue my passions and interests outside the confines of a traditional office.

Read more: Reasons to Quit Your Office Job

It’s been a little over one year, and things sure have changed. I traded in my suits and heels for leggings and bare feet and upgraded my stuffy corporate office for the calm serenity of parks, beaches, and new cities. 

Nowadays, I work whenever and wherever I want with absolutely no limitations except for a bit of WiFi and my trusty laptop.

Getting Started & Believing in Yourself

The decision to work remotely and travel is more psychological than logistical. You must believe in yourself to make the right step.

If you’re curious as to how I pulled it all off, the answer is pretty simple: with a lot of trust and support. Learning how to work remotely and travelinfo-icon the world isn’t logistical, it’s psychological.

At the end of the day, you’re taking a gamble on yourself and praying like hell that you will figure it out in the end. Unfortunately, no amount of sage wisdom from me or anyone else will be enough to convince you that you’re ready; for me, I had to wake up one day and decide that I wanted to try. 

What I can say is this: you CAN do it.

Sure, it’s going to be hard. Really, truly, gut-wrenchingly hard sometimes. And yes, you are going to doubt yourself and your decisions. But in these times of doubt, try to remind yourself why you wanted to try this crazy lifestyle in the first place. 

Maybe you’ve always wanted to travel, but never had the time or you’ve been craving more adventure and wanderlust, but lacked the funds to do so. Whatever your reasoning, know that it is possible to work remotely and travel the world while pursuing your passion…as long as you put a little thinking into it.

Putting All of Your Cards on the Table

You can turn almost any of your tech skills into a sustainable consulting business.

Once you’ve built up enough courage to move forward, it’s time to decide what you want to do for a living. While plenty of people have pulled a complete 180 like me and tried a new career, you don’t have to take the plunge all at once. 

Depending on your profession, you very well may be able to turn your current knowledge and skills into a consulting business (lookin’ at you, web designers, graphic designers, and just generally tech-savvy people!).

Whatever your calling may be, eventually the time will come for you to say so long to your current job and get started with your dream to work remotely and travel. Pro tip: a bit of savings doesn’t hurt during this initial phase either!

Spreading Your Wings & Leaving Your Home Office

Pro tip: don't limit your remote work to your home office. There is a whole world out there for you to experience.

Most freelancers (myself included) have gone through a phase where they don’t leave their home office. Call it a growing pain or just an old habit that’s hard to kick, but sometimes it’s just easier to make the transition from a traditional 9-5 to remote work from the comfort of your home office.

Look, home offices are great. Stellar in fact. But did you really give up that 401K and company-funded health insurance just to talk to your cat on your lunch breaks and catch re-runs of Seinfeld in the afternoon?

One of the hardest lessons for me to learn as a freelancer was that I actually could work anytime, and anywhere my little heart desired. Sure, there are days that I crave the comforts of home or a decent co-working space, but the whole reason I left the law in the first place was to see the places and people I love at any given time.

Read more: Some Tips for Remote Workers and Travellers

Don’t be afraid to depart from the nest a bit. Pack up your laptop and charger, and head out into this wonderful world armed with the knowledge that working remotely really is as simple as overcoming your own feelings of self-doubt and fear. 

When it comes to remote work and travel, there really isn’t a place you cannot visit or an experience you cannot have; in fact, I would argue that the only limitations are the ones you arbitrarily place upon yourself.


Ditching my former life as an attorney to become a freelance writer was the best decision I ever made. I now enjoy a life full of endless possibilities doing work that I absolutely love in places I love even more. And if I can learn how to work remotely and travel at the same time, you can too!

Elizabeth Murray freelance content writer at aSabbatical.com
Traveling is about expanding your mindset and challenging every custom, tradition, and way of life you thought you knew.