10 Challenges of Working Remotely While Travelling (with Solutions)

In Travel While Working by Phoebe Nicolas

One of the greatest advantages of working remotely is the ability to work anywhere in the world. With just a laptop and adequate internet connection, working remotely gives you the opportunity to travel and always be on the go while earning money. This lifestyle seems exciting and fun, but working remotely while travelling is not always rainbows and unicorns. It’s not as easy as some people may think. In this article I address some of the challenges of working remotely while travelling and some tips on how to overcome them.

I’ve been a remote worker for 6 years and most of it was only a part time gig, until I finally decided to do it full time so I can travel more. Although I love the freedom that comes with it, working alone without your boss and colleagues around is a bittersweet experience. You may have the freedom to work anywhere or wear whatever you like, but it also comes with struggles that you need to first resolve on your own before you use your “call a friend” lifeline.

1. The loneliness and sadness

Working away from your colleagues and friends can be lonely and quiet. This challenge is hard for the person who likes an occasional chit-chat while working. I’ve worked in an office environment for over 10 years and so was having other people around me was normal. I found it very difficult to work remotely full time in the beginning and the adjustment to a new environment wasn’t easy. There are times that I remember the happy memories at the office like our team lunch, the afternoon gossips with my work friends and our story sharing. Thinking of these things can make you begin to feel sad at times.

How to overcome the loneliness?

  • Try not to think about it because the more you think about the loneliness, the more you put yourself in a sad situation.
  • Play some music while you’re working, music that is fun, relaxing and positive to listen to. You can turn on the TV so it would feel like there are people chatting around you.
  • You can also choose to work somewhere with crowds, like in a coffee shop or a restaurant.
  • Be active and engage yourself in online conversation, chat with your colleagues, or video call a friend. Just make sure that it won’t affect your work output.

2. Being homesick and missing your family and friends back home

Every remote worker who travels a lot gets homesick at some point. It could be because you’re missing your mom’s cooking, your late night partying with friends, your dog and cat or just the life in general back home. Long term travelling can be fun but it does have trade-offs and downsides, and that includes being homesick. Another thing to note is it can be a bit of a culture shock if travelling to a foreign place with different culture and language that seems hard to learn. These new things can be challenging as we have many habits back home and when the scenario changes, we are far away from the comfort of family and friends to help us through it.

How to overcome this feeling?

  • First and foremost, try to be open-minded and friendly to everyone you meet, don’t be a stranger! This will give you the opportunity to become friends with other travellers and even locals.
  • Start building relationships with everyone you come across while you’re travelling. You can also join some online communities, meet up with people and make friends wherever you go.
  • It is also important to get yourself involved in the country’s culture and customs. Try new things that you wouldn’t normally do, eat or see and enjoy the moment.
  • And lastly, keep the communications open with your family and friends back home.

3. Making regular friends

While you’re being open-minded and ready to mingle with everyone as I mentioned on point no. 2, making regular friends when you’re always on the go can also be a bit difficult. No doubt you can meet different kinds of people while travelling and some of them can become really good friends. But most of the people that you’ll meet will likely be just temporary friends while you’re on the road. If you’re working while travelling, you might find it hard to balance your time between hanging out with your newly found buddies and finishing your report for your boss who may be waiting on the other side of the world.

How to keep these friends?

  • Well, there is really no way to keep these new friends intact, as either you or them will have to say goodbye at some point. And in most cases, you’ll never talk to these people ever again. That’s the sad truth. If you really wish the friendship to continue is up to you.
  • You can always keep in touch through a number of instant messaging services like Skype, Whatsapp, Line and Viber. Otherwise, move on, be thankful and make new friends at your next destination.

4. Following a work schedule

If you’re working remotely while travelling, it can be tempting to abandon your work and just wander around. You might be caught in the middle of whether to go on the island hopping tour or do your job. There are times that your attention will be drawn to your surroundings and you will be tempted to leave your work behind to have fun. From the pristine beaches to the wonderful architectures around you, temptation is everywhere when you’re travelling.

How to control these temptations?

  • Working remotely while travelling requires a lot of self-discipline. Although you have the license to work anywhere you want, you also have the responsibility to do your job.
  • Following a work schedule will definitely help you get things done. You have to formulate a good scheduling system while working and travelling.
  • Be creative and keep in mind that you also need to accomplish your work and not miss deadlines.

If you follow these golden rules, you’re not only doing yourself a favour by avoiding work from piling up, you can also do the touristy things guilt and worry free.

5. Comfortable work space

Working remotely does not always come with comfort and convenience, especially while travelling. While lodging will likely be available wherever you go, like hotels, apartments and hostels, a traveller may still end up in a place where it’ll be hard to perform work. An example of this is the noisy environment of hostels and the surrounding neighbourhood. If you like working alone and take pleasure in the peace and quiet, working remotely can be challenging if there are distractions around you. And because you still need to get work done while travelling, a comfortable and laptop-friendly space with available electrical outlet can be difficult to find in a crowded place.

How to find a comfortable work space?

In picking your work space while travelling, whether it’s a hotel or any other lodging, there are a few specific things to consider:

  • First is the location, are there any coffee shops or restaurants with sufficient internet connection nearby if you want to work outside of your lodging? Is it convenient to travel around the area? And if you’ll be using public transportation, you’ll probably want to find a place that is easily accessible.
  • Another thing to consider is designating a laptop friendly space where you can do your job easily, like a balcony or a chair and table with lesser obstructions that can potentially block wi-fi signal.

Tip: Before your trip, go ahead and research if there are any co-working facilities nearby. These co-working facilities offer work space for people who travel and work. For a minimal fee, they offer comfortable work stations, wi-fi, food and beverages and even printers.

6. Bad internet connection

Remote workers rely on the internet 99% percent of the time to do their job, so bad internet connection is the worst nightmare of every remote worker. It can be difficult to know if the destination you’re heading to have good internet service. Most of the lodging that you’ll see online advertises that they have wi-fi in their rooms, but then you’ll end up with almost like a dial-up speed once you’ve settled. And when you choose to work in a coffee shop or at the common area, sharing wi-fi signal with other patrons causes lesser bandwidth due to over-utilization.

How to prepare for these possibilities?

  • It’s advisable to ask for a speed test result from the host of your chosen accommodation before checking in. Just so you know what to expect and you can prepare ahead of your trip.
  • Always bring a back up mobile dongle. Many internet service providers have a little kiosk at the airport and you can buy a simcard or even rent a pocket wi-fi just in case.
  • It’s also good to read reviews for each chosen lodging as you’ll definitely find first-hand information from other travellers about the internet service in the area, so you’ll have an idea.

7. Keeping yourself healthy

I have to admit, I gained weight since I started working remotely. The daily routine of waking up in the morning, turn on my computer and immediately facing my work without much movement is the reason.  While I enjoy the benefit of not commuting to work, I also stopped my morning routine of walking to the shuttle/train station. When I’m working from home, I also find it hard to cook healthy dishes, because I would usually opt for foods that are easy to prepare, like canned goods and microwavable meals. This can also happen when you’re on a budget when travelling. And while I’m happy because I don’t need to wake up super early anymore due to the flexible working, I have ended up breaking my normal body clock and started sleeping late!

How to stay healthy?

This question isn’t rocket science. Keeping yourself healthy can be achieved if you have self-discipline and if you know which routine works well for you:

  • You can choose to do a morning run or engage in some exercise in the afternoon. While the gym offers variety of equipment, there are many exercise tutorials that you can find online and it’s free.
  • If you’re location dependent, it would help if you can do a short swim or take a walk around the area before or after work. Get out and feel the sunshine!
  • When it comes to your eating habit, always go for healthy and nutritious meals. Don’t skip breakfast, minimize temptations and most importantly, prevent overeating.

8. Different time zone and locations

In my situation, my boss is located in the UK while I live and travel mostly in South East Asia. Submitting my work or sending urgent emails in a morning my time would mean I won’t be getting a reply until it’s the afternoon earliest. The same goes for those who work with a team spread across multiple countries, cities, and time zones. If you need a quick reply, you may not get a quick reply due to the time difference. This may cause you to delay your work because you’re waiting on something or someone, leading to prolonged time-frame to finish your work.

How to deal with this unavoidable situation?

  • Try to submit your work ahead of the deadline, at least 24-48 hours prior. This ensures that everyone, no matter what time zone they’re in, will have the chance to view the work and take their part in time to complete their end of the project. This also gives you enough time to do some revisions if needed.
  • Another crucial thing to do is to always try and resolve any issues you may encounter before passing it to a team expert for resolution. A simple Google search for answers can help you save time from waiting for someone else to attend to your needs.
  • It would also be good to have a shared knowledge base or portal that can be accessed by everyone in the team for easier dissemination of information.

9. Getting paid on time

Getting paid on time as a remote worker can be tricky. The anxiety of if you will receive the payment before your bill’s due date will always be there. I had a firsthand experience of this very challenging situation in the early days.

My boss decided to use PayPal for my salary, and although my boss paid me immediately as always, PayPal insisted to hold my money for another 21 days as part of their policy. PayPal wanted me to prove them that I am trust worthy before I could get my hard earned money.

So we ended up using a different money transfer company, and then had to process a refund. The new money transfer company also had its red tape! One issue was that my boss processed the payment on a Friday, before a British bank holiday, which then was not processed and verified quickly due to the lack of resource at the money transfer company. Additional security checks needed to be undertaken since he set up a new account, which he was only able to answer when he got back from his camping trip. I ended up waiting for a total of 5 days before receiving my salary.

How can you avoid this?

  • Don’t be afraid to continually check-in on your payments when the salary day is approaching. You may need to remind your employer as they may overlook this.
  • Always use a trusted money transfer company and familiarize yourself with their policies. Most of them implement stricter rules when sending money overseas so make sure that you’re aware of this.
  • Use time tracker app that records and take screenshots of your work. This will ensure that you have proofs of your work to avoid disputes.

10. Keeping your possessions safe

A remote worker who travels a lot has quite a few precious possessions he or she just can’t travel without. These are valuables like laptop, passport, cameras and of course cash and bank cards. While some places are considered safer and more secure than others, a traveller must always be on the lookout for risky situations. Regardless of what journey you take, keeping your valuables safe and in your possession all the time is always a priority.

How to keep your possessions safe?

  • When travelling by train or bus, avoid putting your valuables under your seat. As much as possible, place it on your lap or somewhere that you can see. For those of us who tend to sleep while travelling, always use a safety lock on your luggage or use Pacsafe WrapSafe Adjustable Cable Lock for your backpack and lock it to something secure.
  • Make sure that the lodging that you book has good reviews when it comes to security and safety. Try to look for hotels or hostels that offer a locker or safety deposit box.
  • It helps to do a little background check when travelling to an unfamiliar country so you know when and where to be more vigilant.
  • When you’re on the go, keep your cash and cards somewhere safe, preferably in a money belt with hidden security pouch for cards, cash and passports. Always keep a stash of cash hidden somewhere like in your shoes or bra, so you’ll have money to spend in case of unfortunate circumstances.
  • Beware of scams and don’t leave your belongings unattended, especially in tourist areas, transport stations, shared rooms and restaurants.

Working remotely and travelling has its pros and cons. It may be a bit challenging, but if you prepare yourself and master the techniques on how to make it work, it will be worth it!

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Phoebe Nicolas