Sitting on the train commuting home from the office, all you see are Instagram reels and TikToks from self-tagged influencers telling you to quit your job, join them, and live your best life while traveling around the world. 

For 10 years, I have done this, but they make it sound like all you have to do is quit your job, pack a bag, and jump on a plane.  

It took me two years to be in a position where I felt comfortable quitting my office job and starting the digital nomad lifestyle. I spent this time clearing debt and saving enough money for six months’ salary in case my crazy plans didn’t work out. 

At Nomad at Fifty, I prefer to be realistic and not sell dreams. After all, this is a life-changing decision, and since you’re likely in your 50s, making the right decision for your future is vital. 

In today’s blog post, I want to highlight the biggest challenges as a digital nomad and how you can overcome them. 

Finding Remote Work

Without a regular income, life is going to be tough.

In your 50s, you will unlikely desire to live in hostel dormitories or sit on a bus for 18 hours to save money. Most 50-year-olds, myself included, enjoy more comfort.

Finding a fully remote job can be challenging since many companies have requested that the workforce return to the office or have introduced hybrid working, where you work from home for 1-3 days a week. These options are possible for digital nomads. 

You have a few options:

1. Be an employee of a company. Many fully distributed companies have a global workforce that works from home. 
2. Be a freelancer for clients. Focus on providing a specific service to companies who are looking for freelancers. 
3. Be a contractor for a company. Short to medium-term contracts with companies that want to hire remote workers. 

The challenge is not just finding a remote job or freelancing clients. Some companies require you to work in a specific timezone, and some only hire people who live in the country where they are located.  

It will take longer to find a company that is flexible about when you work and where you are based.

Potential tax and legal implications exist, so some companies do not want their workforce to travel. 

You can find companies depending on the type of role. Consider your skills and experience and start building a network before quitting your office job to become a digital nomad. 

One of the biggest lessons I have learned is that being multi-skilled opens up more opportunities for remote work. Spend time learning new skills on YouTube, courses, and online tutorials. 

Invest in yourself by learning new skills, increasing your chances of staying employed. 

Financial and Money

Many financial challenges can make your digital nomad lifestyle stressful. The chances of these issues occurring are considerably higher when traveling from one country to another. 

1. Scams and fraud. Unfortunately, some people see tourists as ATMs, and you will be the focus of scams and fraudulent activities. Before planning your next destination, read about common scams. Being informed will reduce the chances of you getting scammed. 
2. Lost or stolen bank cards. Don’t let go of your debit or credit card when paying in a restaurant, coffee shop, etc. Ensure you have a backup if your primary bank card gets lost or stolen. You should only use ATMs in banks, not random locations on the high street. 
3. Protect your data. Use a VPN when working in a coffee shop or public WiFI network. I have used and recommend Surfshark or NordVPN. Have anti-virus and malware software on your laptop to protect your personal data. 

One typical scam attempt might occur because you use a local SIM card. Scammers pretending to be a local bank will send messages to your phone. Never click links in messages or emails.  

When purchasing products or services, check the price to see if it is clearly labeled. Some places charge a higher price for tourists and set a price based on your appearance. 

On the subject of prices, sadly, some countries charge a higher price for attractions depending on whether you are a local or a tourist. Thailand and Malaysia are two countries guilty of this, and the price is considerably higher, but there’s not much you can do other than not visit.

Before withdrawing money at ATMs, check with the bank about the fees they charge for using a foreign bank card, which can become very expensive.  

The same can be said of your bank at home. Use a bank that does not charge fees for using your bank card abroad. 

Finally, remember that medical insurance prices drastically increase when you reach 50 years old.

Don’t take the risk, and make sure you are financially covered for medical treatment. When purchasing insurance, ensure that any pre-existing conditions are covered. 

Health and Wellbeing 

Keeping healthy physically and mentally can be a challenge no matter your age, but especially in your 50s. 

Believe me when I say eating delicious, unhealthy food when traveling is tempting. Of course, treat yourself occasionally, but eating unhealthy food consistently will lead to health issues, bringing your travels to an abrupt and potentially costly end. 

Ensure you exercise regularly, be it an hour in the gym or a brisk walk between work. Working remotely from home can be challenging, as it can be challenging to disconnect from work and maintain a good work-life balance. 

There is no doubt that when you hit your 50s, health challenges do become more common. 

Ensure that you are not keeping yourself too isolated.

Make time for your passions in life and try to find people who share those same passions. Go to local events and find activities that you can participate in.   

If you find yourself in a place that is affecting your mental health, learn to detect this early on and move on to a new place. Maybe the weather is dreadful, you don’t feel safe on the streets, or you think you need home comforts. Do what is best for you. 

I planned to spend three months in Vietnam.

However, it was a bad time of year to visit, with torrential rain all day long. The weather was affecting my mood, so I left early. In these situations, losing money is less important than your mental health. It was also bad planning on my part. 

Visa Challenges 

Visas only became challenging when the United Kingdom left the European Union. This made navigating Europe more difficult, as you went from being able to spend any time you wanted in the EU to only three months in six months. That’s why I spent most of my time in Asia: I could stay for three months in most countries. 

Depending on your passport, visa challenges might make navigating the world even more complicated, so you must do this research before deciding to become a digital nomad.  

Thankfully, since the pandemic, more countries are opening up to remote workers who want to spend more time in a country.

Please read my post on the pros and cons and what I learned from 10 years as a digital nomad. Both posts have helpful information to help you make an informed decision. Quitting your office job to work remotely and travel the world is life-changing.