About the author

Darren Cronian, the author of this guide, has spent eight years securing remote jobs and building a successful freelancing business. His goal is to help people escape the office. Read more >

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

The truth is there are challenges with working remotely and traveling. You might discover photos of beautiful people working poolside or on the beach on social media, but 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 own company, so working remotely suits me perfectly, but if you are an extrovert, you might want to look at events where you are staying on sites like meet other like-minded people.

Another option is to work in a co-working space where you can network. Your mental health is essential, so take steps to socialize with people and start conversations in coffee shops.

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 the destination, buy a sim card with internet data. Use this as your backup should the internet, not function.

For your mobile phone, it’s also recommended to have this unlocked so you can 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, especially when you tell them you will be working online, they will be honest.

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 miss 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. Have your accommodation address written down and saved 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 any questions to the host.

Struggles to get motivated to work

It happens to us all, whether you are working 9-5 in an office or a coffee shop in Tokyo. Since you have no one watching over you to motivate you, it can be a struggle at first.

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 introducing a routine into your life. Initially, you will want to tweak this routine until you find the time of the 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 and save a high percentage 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 the Self Employed, especially if you connect your bank account to the service since this will allow you to manage personal and business spending and save you a ton of time when completing your tax returns.

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 out each day to exercise, and it doesn’t have to be a session in the gym; it could be a leisurely walk, swimming, or participating in a hobby/interest that will get you out and about.

Regular check-ups with a doctor, at least once a year, are advisable. Make sure you have the appropriate vaccinations depending on where you travel. If you have medication, take enough for your trip, and take a copy of your prescription should you need more tablets.

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

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