8 Pros and Cons of the Digital Nomad Lifestyle & Working Remote

Digital Nomad

It’s almost difficult to comprehend that it has been 5 years since we started this crazy remote work journey traveling the world. What began as a long backpacking trip, slowly evolved into a website which we now run full time as digital nomads aboard. While it can be an exciting world there are certainly some pros and cons of working remote. Just to be clear… We wouldn’t trade this digital nomad lifestyle for anything! Yet, there are some important realities to be aware of with working online and traveling.

8 Pros and Cons of Being a Digital Nomad

1. Pro: Ultimate Freedom 

Hands down, the best part of remote work is the freedom that comes with it. As digital nomads, we have enjoyed being able to live anywhere in the world!

Thinking back on our last 6 months, we spent 5 weeks in Bali, 2 months island hopping in Thailand, got a longterm rental in Central Vietnam, and even visited friends and family in the United States.

We’re currently sitting on our balcony in Croatia getting ready for a fun and exciting summer working online in Europe. Before our digital nomad lifestyle this could have never been a possibility!

Digital Nomad Lifestyle Tips

2. Con: Digital Nomad Visa Restrictions 

One thing that you might not think of if you haven’t extensively traveled while working remote is the different visas. This is something that is always on our mind as digital nomads and often what our plans evolve around. 

It’s not necessarily a con that would hold us back from working online somewhere, but more something that we need to be conscious of. It also can be an expensive problem to fix when you need extensions! 

If you’ve never heard the words “Visa run” then you will probably very soon. Each country has its own visa requirements in terms of how long you can visit and if it’s possible to make an extension. 

For example, when traveling to the massive digital nomad hub of Bali you will get a 30 day visa on arrival. Once in the country, you have the option to extend this one time. However, you’ll have to pay a company to help you or go to the visa office 3 different times to process the extension.

Once the 90 days are up there is not other option except to book a flight out of Indonesia. The good thing is that you can return right away. In total, for a 60 day stay in Bali (including the visa extension) you’re looking at around $100 USD per person. 

This con of the digital nomad lifestyle would trip us up once again this past winter in Vietnam. They were only offering 30 day visas at the time so we had to book a round trip flight to Singapore. While we absolutely love Singapore,  the flights and additional visas cost us $250 each. 

Know that this is very common all over the world and not just Asia. Right now we are counting down and planning for every day we can be in Europe’s Schengen Area before we have to leave for 3 months. So you can see how it would be one of the hesitations to international remote work.

How to Get an Indonesia Visa on Arrival & Easy Bali Visa Extension

Digital Nomad Visa

3. Pro: Slow Travel 

Okay, back to the digital nomad benefits! One of the biggest advantages of working remote is the ability it gives you to slow travel.

When we first started out on an extended backpacking trip we were moving accommodations every other day. We felt this panic of making once in a lifetime memories before returning to what was  our idea of the “real world” aka corporate jobs. 

For us, working remote now goes hand and hand with slow travel! At first you might feel the need to see everything even as a digital nomad blogger. However, at one point it will be impossible not to burn out. That’s why we’ve found it much more satisfactory to stay in the same area for weeks or even months at a time.

Slow travel is designed to really let you dive into the culture of the country you are visiting and enjoy it. Maybe it’s renting a spot on a small Greek Island for a month, or spending an extended period in a city you’ve always wanted to explore. 

This way you are able to develop a remote work routine in a place you might have never imagined possible. Not to mention, you’ll save money by renting places for longer periods!

Digital Nomad Slow Travel

4. Con: Dependent on Wifi

When it comes down to it every digital nomad needs wifi. Of course, the strength of internet may depend on how you’re actually working online. For us the biggest challenge is finding wifi that we’re both able to work on at the same time and be able to upload high quality pictures on. 

Now in many parts of the world this won’t be an issue at all. Yet, some of the most popular destinations we’ve been to in Southeast Asia and Latin America it has been more of a challenge… Especially while enjoying the most beautiful islands and faraway villages!

So how do we combat this as full-time digital nomads? First off, we will always verify the place we’d like to stay has strong wifi before booking. The other thing we’ll do is buy sim cards for our phone as soon as we land at the airport.

Particularly in Asia, they can be as cheap as $10 a month for unlimited service! From here you’re able to hotspot your computer for working online when need be.

Pros and Cons Digital Nomads

5. Pro: Meeting Other Digital Nomads & Creatives

When we first started out on this remote work journey people thought we were crazy. So to be honest, we started to get in that mindset as well! Nevertheless, we would quickly find out there is a massive community of digital nomads who travel the world working online.

One of the things we appreciate most about traveling full-time is that it’s extremely easy to meet others. From online forums to facebook groups and co-working cafes, you will come across so many others doing the same as you!

When we were working remote in Thailand we booked a small bungalow right on the beach on the island of Koh Lanta. The day after we checked in another couple moved into the place next door. 

It wasn’t long before we noticed that they had the same daily routine of working online as us. Before we knew it, we struck up a conversation and started getting a nightly dinner with them. We actually ended up traveling with this couple for the next two weeks through Thailand together!

After many years traveling, we can say the same about other places we have visited. You find a common bond with other digital nomads because everyone has pushed outside their comfort zone to build the life they want. 

Digital Nomad Guide

6. Con: Getting Sick Abroad

There is no way around this part folks. Getting sick while at home is never fun, but when it happens somewhere abroad it’s far worse.

When you’re in a country you’ve never been to before it can be an especially uncomfortable and a scary feeling. Trust us when we say we have certainly had a few bumps in the road along the way! 

The good news is that there are now great companies who work with digital nomads for international health care. This is a game changer for people like us working online! Personally, we have used SafetyWing for years and they have always been there when we need them. 

They give us the confidence to go even the wildest places knowing we’re covered. You should never travel without insurance, whether it’s for a short holiday or extended time as a digital nomad. 

For example, while working online from Mexico we both caught a nasty stomach bug. So after several days of being sick we decided to make a trip to the western clinic.

Being at a hospital in a foreign country is never fun. However, we knew that we had SafetyWing to cover our medical costs. Hours later we got the proper medication we needed and were on our way!

There are many steps you can take to prevent food poisoning and other common illnesses while traveling. The most important thing is that you’re covered though in case something does happen.

See Why SafetyWing is Such a Popular Insurance for Digital Nomads!

Digital Nomad Pros and Cons

7. Pro: Unlimited Earnings & Being Your Own Boss

We understand that this might not be the situation for every digital nomad working remote. Yet, more often than not, the travelers we meet hold the power of generating their own earnings.

Many own their own companies or websites and have complete control over how much they work. With us, the amount of blogs we write is the direct link to how much money we make!

Even those that are working online for a company might also take on additional clients on the side. The digital nomad lifestyle gives you so much opportunity like this.

For instance, six months ago my sister was living in Bali and wanted more income. She decided to take on some extra clients using  Upwork.

She now writes freelance full-time and has so many clients coming to her she has to turn some down. Her remote work also gives her the freedom to complete her projects and not accept any more if she wanted to take a week or two off.

If you are new to these digital nomad benefits then we recommend looking into Upwork. We haven’t used it, but have met so many others that are super successful. A lot of remote work friends have told us it started out as a side hobby, and turned into a full time digital nomad job!

Working Remote as Digital Nomad

8. Con: Budgeting & Remote Work Expenses

You may go into a normal vacation with a freestyle mentality because you worked all year for it. So to travel around the world as a digital nomad working remote is very different! Really, you need to learn to budget the same as you would if you weren’t traveling full-time.

At the end of the month are you making enough to cover your accommodations, insurance, flights, food, and other expenses? If not, then you’ll have to adjust your spending or even your location. This is one of the reasons that you will find so many digital nomads in Southeast Asia where their money goes further.

Another cost to think about is having the proper electronics for working online. That may be as simple a laptop computer, or if you’re like us you might need cameras, drones, and other special equipment. This is one of the work from anywhere drawbacks that you could come across.

We’ve found that we actually spend less in most places traveling than we did living in San Diego or Boston. While we did love our life in sunny California, the U.S. in general is very pricey! Just know that depending on where you are and what you’re doing, it can be expensive to be a digital nomad! 

Remote Work Guide

Is the Digital Nomad Lifestyle For You?

Now that you’ve learned the pros of digital nomad life and work from anywhere drawbacks, is it the right move? That’s something only you can decide! We 100% get if you like the stability of a normal job, owning a house, and staying in one place.

Yet, if you’re open to working remote there is a whole world out there to discover. Starting our blog is the best decision we’ve ever made and our business is constantly growing. 

As the years have gone on, working online has only become easier and more socially acceptable. Hopefully, this article has inspired some wanderlust and opened your eyes to the digital nomad lifestyle! 

Working Remote Digital Nomad

Have any questions about this article or want to share your own remote work pros and cons? Let us know in the comments below! 

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar


Digital Nomad

Nothing Familiar Travel Tips 

 Flights: We always find our cheap flight deals using Skyscanner. That’s how we flew from Norway to Poland for under $20 USD, and Thailand to Vietnam for less than $50! 

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com, Agoda, & Vrbo!

Rental Car: We use Discover Cars to explore when traveling. A quick travel tip is to ask for a weekly rate than just booking 2-3 days.

 Tours: Check out Get Your Guide to find thousands of activities around the world. From street food tours to skip the line entry passes! 

 Travel Insurance: Never travel abroad without protection. We’ve been using SafetyWing for the last few years on the road and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

Nothing Familiar Travel Planning

*We receive a commission for purchases made through links in this post. This allows us to continue our travels and keep providing great content to our readers! Also, as an Amazon Associate we earn from qualifying purchases.


  1. Al
    April 15, 2023 / 4:55 am

    I’ve been living the nomad life since 2014 and i love it. I’m not digital. I retired early, so I don’t have a need for wifi or income, gratefully, but i absolutely love the lifestyle and don’t see myself settling down ever.

    • Brigitte & Jake
      April 15, 2023 / 5:00 am

      That’s so great to hear! Sounds like the best way to spend your retirement (-:

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