About the author

Darren Cronian, the author of this guide, has spent nine years securing remote jobs and building a successful freelancing business. His goal is to help people find remote work. Read more >
Last Updated: 13 January 2025

Escaping the office to work remotely and travel will be the best decision, but there are some challenges to overcome to become a successful remote worker.

The truth is that working remotely and traveling can present challenges. While social media might show photos of beautiful people working poolside or on the beach, these images hide the hard work behind the scenes.

Working while traveling has many benefits, so taking the time to overcome the challenges makes it all worthwhile.

This guide will focus on overcoming the challenges of remote work while traveling so you can become a successful remote worker.

Challenges of Remote Working While Traveling
Feeling Alone

Going from working in an office full of people to working alone in your apartment can be a lonely experience. It’s essential to keep connected with loved ones through technology like messaging apps.

For conversation, the tool of choice for many remote workers is Slack.

I am an introvert and love my company, so working remotely suits me perfectly. However, if you are an extrovert, you might want to consider events where you can stay on-site and meet other like-minded people.

Another option is to work in a co-working space where you can network. Socializing and starting conversations in coffee shops is essential for your mental health.

Internet Issues

As a remote worker, being unable to connect to the internet to work is probably one of the more stressful things that can happen to you.

Without delay, purchase a MiFi hub that is unlocked to any network. Then, when you arrive at your destination, buy a SIM card with internet data. Use this as your backup if the internet does not function.

You should also unlock your mobile phone to use any SIM card and set up a personal hotspot.

Airbnb is my chosen accommodation provider, and when contacting hosts there are a series of questions are asked:

Is the internet connection shared with any other apartments? Is the accommodation on a dedicated WiFi box that you can access for any issues? Is the internet reliable? What speed is the internet?

If the host wants your experience to be positive, they will be honest, especially when you tell them you will work online.

There was only one occasion where the internet was not what the host had said, and a negative review was left for them.

Travel Can Be Stressful

Let’s be honest: as much as it changes our lives, travel can be stressful. Flights can be canceled or delayed, meaning you missed your connecting flight.

Accommodation might not meet its expectations; believe me, this happens often. You also must have your wits about you with tourist scams. You must deal with these issues head-on and move past them as quickly as you can.

Being prepared and organized can save you a lot of stress; this is one of the many lessons learned. Write down your accommodation address and save it to Google Maps.

Note your flight details, and keep a copy of your passport securely but accessible online. As was said earlier, accommodation can throw up surprises like unclean apartments, noise disturbances, and inaccurate information.

Read through any reviews, closely examine the photos, and ask the host questions.

Struggles to Get Motivated to Work

It happens to us all, whether we work 9-5 in an office or a coffee shop in Tokyo. It can be a struggle since no one is watching over us to motivate us.

More so since you’ll want to explore the places you are staying in and not spend all your days staring at the walls in your accommodation.

However, if you do not put in the effort, you’ll not generate enough revenue to work remotely. The solution is to introduce a routine into your life. Initially, you will want to tweak this routine until you find the time of day when you are most productive.

Working in the evening was the best time because I needed to get out and explore during the day.

Don’t feel, though, that this routine has to be strict. You could decide to change it to a specific day of the week. What’s important is that you build the perfect work-life balance and give yourself freedom.

Poor Money Management

It’s essential to manage your money. Every time you are paid, put a percentage away in a bank account for taxes and try to save a high rate of your income for emergencies or to pay for future luxuries. Then, budget how much you must spend until you are next paid.

Money management is crucial as a freelancer since you will not know when the next invoice will be processed.

QuickBooks is highly recommended for self-employed people, especially if you access the service using your bank account. This will allow you to manage personal and business spending and save time when completing your taxes.

Feeling Unwell Abroad

Keeping healthy is essential when working remotely while traveling, and having adequate travel and health insurance is a must unless you want to lose all of your savings on medical bills.

Healthcare can be more expensive than in your home country, especially if you are from the UK and used to the free NHS.

Make sure you take time each day to exercise. It doesn’t have to be a session in the gym; it could be a leisurely walk, swimming, or participating in a hobby or interest that gets you out and about.

It is advisable to have regular check-ups with a doctor at least once a year. Depending on where you travel, ensure you have an adequate amount of medication and a copy of your prescription.

Challenges of Remote Working While Traveling

Overcoming the challenges of remote working while traveling will make your life and travel experiences stress-free and memorable.

Share This Guide

How to get a remote job

The Essential Quick Guide for Remote Job Success

Embark on Your Journey to Remote Job Success Today!

We bring you actionable strategies and in-depth advice. All curated from an experienced remote work coach – delivered straight to your inbox every month.

  • Learn best practices for job applications
  • Receive more interview invites

  • Stand out amongst other applicants

  • Access subscriber only content