10 Reasons Why It’s Difficult to live the Digital Nomad Lifestyle

Sharing is caring!

Becoming a Digital Nomad and traveling the world working from wherever your laptop is set up is the dream right? Type #digitalnomad into Instagram and you will, I’m sure, be swamped with images of Macbooks, lattes and beach views. The digital nomad lifestyle, being able to travel whenever and wherever you like and still earn money seems to be what so many are aspiring to. But is being a traveling freelancer really all it’s cracked up to be? In this article, I’m going to share with you some reasons why it’s difficult to live the Digital Nomad Lifestyle.  

Granted, it’s pretty amazing to be able to work whilst traveling the world, but being a Digital Nomad also has its downsides. It’s most definitely a dream job. But it’s also seriously challenging and not the lifestyle for everyone. So before you start looking for digital nomad jobs or begging your boss to let you work remotely take a read of my 10 reasons why it is difficult to be a traveling freelancer.

1. Trying to be productive as a Digital Nomad when the beach is calling

If you think living the location independent lifestyle means you will be sunning yourself at the beach with a cocktail in hand every day you are kidding yourself. Yes, absolutely weekends and days off you will find me hitting the beach, climbing a volcano or trekking through the jungle. But the rest of the time I’m either locked in my bedroom, at a coworking space, or in a hotel room in front of my laptop.

A lot of the time I can choose my working hours, so if I want to skip work for the day to go on an adventure with friends I can. But in all honesty, more times than not I have deadlines to meet so I have to decline.

Claire's Itchy Feet | Making Money | 10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle

This isn’t so bad if you are with other Digital Nomads who are also working. But it’s the times when I’ve found myself at a hostel with backpackers when it has been most challenging. Backpackers who aren’t working and spending every day exploring and every night partying. It can get seriously depressing constantly having to say no to their invitations.

It’s important to find a balance, which can be easier said than done when the beach is calling! I prefer to live with other people working remotely. This way I can still be social without the consent temptation of adventures and crazy parties.

2. Finding a place to work remotely 

For the first year, I worked wherever I was staying. I always made sure there was WiFi and I didn’t even consider paying extra for a coworking space. It seemed like a waste of money. That was until I booked a free day at a Coworking space and realized how much more productive I was. You can find places to work easily by googling coworking spaces. 

Claire's Itchy Feet | Making Money | 10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle

Pricing really varies. In NYC I paid $50-$100 a month 8-6pm Monday – Friday, In Medellin I paid around $5 a day and in Playa Del Carmen I paid over $15 per day. As a standard for your fee you normally get a flexible workspace, free tea, coffee, and water, super fast internet and AC! I can’t even tell you how important AC is working somewhere like Playa Del Carmen!

Having a dedicated workspace isn’t always possible, but if you can find a Coworking space, where you can work remotely, that doesn’t blow your budget, it really can be worth it. I know I’m far more productive in a coworking space than I am in a hotel room.

Safety Wing Insurance for Nomads

3. Are you ever going to pay me? Getting paid as a freelancer

If you are a freelancer you are reliant on people paying you per job. Although on the whole I’ve been lucky and most clients pay me quickly. I’ve also had nightmares with clients taking months to pay me.

If you don’t have an emergency back up fund tucked away this can be a total disaster. To work as a traveling freelancer you have to obsessive manage your finances. Unless you want to end up stuck in a beautiful place and unable to enjoy it because no one has paid you.

4. Where did all the good jobs go? Finding remote jobs

I must admit I have been lucky on the job front and my remote freelance work is steady.

One of my favorite places to connect with other remote workers and look for location-independent jobs is My friend Andreas Digital Nomad Jobs Directory

There are several other websites dedicated to advertising digital nomad jobs or where remote workers can advertise their services. Two of the best known recruiting websites are Fiverr and Upwork.

However, there is a lot of competition and it can take time to build up a good reputation. If you have digital skills you can sell as a freelancer these are great places to start. I personally have hired people via Facebook and found jobs via facebook digital nomad community groups. So it pays to be active in online communities.

5. WiFi, wherefore art thou WiFi

My life as a Digital Nomad pretty much revolves around WiFi. Seriously, I can’t even tell you the hours I’ve spent checking the reviews on booking.com for comments about WiFi.

As I travel solo AirBnB is often out of my budget so I have to rely on the WiFi in my hostel or hotel. If I’m staying somewhere for a month or more then I normally rent a room in a shared house with other remote workers. Before I’ll even look at a room though I have to ask what the WiFi speed is. When I view I will take my laptop and run a speed test.

There have been so many places that I really wanted to stay, but due to unstable WiFi, I have to leave. These days I check before I move to a new location by finding and joining a new digital nomad community on Facebook for that area and posting in the group asking about WiFi. I also ask if anyone has a spare room in their house for rent with good WiFi which is how I have found my last few rooms.

One thing that was a total gamechanger for me was getting a KeepGo. A KeepGo is a mobile 4G hotspot that works worldwide. Unlike mobile tethering which can be expensive and unstable, this gives you solid fast coverage. As an online English teacher, it was important for me to have a backup, just in case! There has been more than one occasion that I have needed to use my KeepGo to teach. I can’t even tell you how glad I was to have it!

Claire's Itchy Feet | Making Money | 10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle


6. Yes, I do need all of those things! Packing light as a Digital Nomad

Honestly, I really do try to pack light. When you have to carry your life in a backpack it makes you super choosy about the travel essentials you take with you. It is important to only pack what you actually need. In many countries, tech gear is very expensive, but toiletries and clothes are cheap. As a traveling freelancer, you have to prioritize the items you need for work over your nice clothes and fancy face cream.

Here are a few tips to help you choose what to pack:

  • Clothing – I choose my clothes by how lightweight they are and how small they fold up. That way I can fit more in.
  • Toiletries – Golden rule buy toiletries at your destination, traveling with bottles of shampoo and shower get takes up space and adds weight. Unless you really can’t live without it leave it behind.  
  • Work equipment – What takes up space (and makes up all of the weight) is all of the equipment I need to work remotely. I know this doesn’t affect all traveling freelancers some just need their laptop and charger. But as I take photos and make films I need a lot of extra equipment that it is difficult (and expensive) to buy outside of the USA. Click here to check out my tech gear.

7. Location independence vs. timezone dependency

When you work in a different location and timezone from your clients/ employer it can get tricky. I taught children in China, I was contracted to work certain hours and I couldn’t easily change this. That meant I would have to double check the time difference when I moved to a new location so I wasn’t having to get up in the middle of the night to teach.

Some of my other work I’m part of a team of freelance remote workers and we really struggle to arrange online meetings as we are in so many different time zones. There are a few tools I use with my teams like Clickup, Slack, and Zoom. They all help us stay connected despite being spread out around the world. Unfortunately, I still struggle sometimes with working out the correct times of online meetings and they are often very early in the morning or very late at night.

8 Travel slow or pay the price

I honestly don’t know how some people travel constantly and work remotely!

Like seriously, please tell me your secret!?

After a few months of being constantly tired and struggling to meet deadlines, I figured out I needed to slow down.




Claire's Itchy Feet | Making Money | 10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle


Here are some pros and cons to think about:

Traveling fast


  • You get to see more places.


  • You will get travel ‘burn out’. Traveling constantly can be tiring and if you are moving to a new place every few days you will get tired quickly. This is going to affect your work productivity.
  • If you are staying in hotels or hostels all the time it is going to get expensive. Renting rooms and apartments for 4 weeks to 3 months could potentially save you a lot of money.

Traveling slow


  • You get to experience ‘living’ in that place/ country.
  • If you can rent a room or apartment with good WiFi you know that you are going to be able to work well during that time.


  • You may end up paying rent in one place and then having to pay for a hotel when you visit places within that country.   

I now move every 3 months, minimum. I’ll find a place in my new country to base myself and rent a room. Then I work for 2-3 weeks solid exploring the local area when I take time off. Once I have done as much work as I can I’ll pack my daypack and travel for 2/ 3 weeks with just the essentials and reduce my ‘work time’ for the duration.  I still pay rent for my apartment and leave everything I don’t need behind.

9. Where did all my friends go? Making friends while traveling solo

Time to get a bit real here. For those of us who travel solo, the nomadic lifestyle can get pretty lonely. If you are moving to a new place every few months that means you are also going to have to find a new place to live, some new friends and you may even need to learn a new language. These aren’t small changes and it can have a big impact on your mental health.

The key is to be prepared. Being part of online communities on Facebook where you can talk to others dealing with the same issues is essential. I have also personally found having a hobby like yoga, CrossFit, dancing or going to the gym can really help you get out and meet people.

10. Look, this isn’t a holiday. No, I’m not lucky, this is a lifestyle choice…

I’ve saved this one until last, as it’s more of a moan than a problem. Yes, if you look at my blog or my Instagram you may think that I spend every day exploring new countries and having exciting adventures.

Which of course I do. But not every day! I work damn hard.

Claire's Itchy Feet | Making Money | 10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle

Some weeks I work 12+ hours a day to get through my workload so I can disappear into the jungle for a few days. I work just like people with ‘normal’ jobs. The only difference is I live very simply I choose to live a nomadic lifestyle over spending money on things like fancy clothes and flash cars. I live in countries where the cost of living is low so my money goes further.  I’m not on holiday. I just get to do cool stuff people do on holiday on my days off.

Like this blog post? Then you will probably like my books…

10 Reasons Why It's Difficult to live the Digital Nomad Lifestyle

Final Thoughts

I love being nomadic, I feel blessed to get to work remotely, and enjoy all of the freedom and flexibility the Digital Nomad Lifestyle offers me. However, just because it is my dream job, doesn’t mean it’s right for everyone. Take your time to really do your research, test the water and take your time to know the downsides to being a Digital Nomad before taking the plunge.

Did You Get Travel Insurance Yet?

If 2020 taught us anything, it’s that you need to be prepared for anything! Travel insurance has always been high my list of things to get before I travel but now more than ever its at the top of my list.

I’m pretty sure we have all had travel plans messed up because of COVID and not all insurers covered this. So when looking for travel insurance it’s important to check it covers travel disruption due to COVID-19, Hey Mondo, Passport Nomads, Safety Wing, and Travel Insurance Master all provide cover for this.

Hey Mondo is great if you are looking for a great value flexible policy. They offer single trip cover, annual multi trip cover, and long term travel cover. You even have the option to start the cover when you are already on your trip, although you won’t be covered for the first 72 hours. For me my favourite feature is their app which offers you a 24/7 Dr chat and the ability to file a claim direct in the app.

Passport Nomads provides the most comprehensive cover for Digital Nomads. The game changer with them is that you have a red card and if you find yourself in need of medical care you just contact them and they will pre load your card with the funds to cover your treatment, meaning you won’t need to pay out of pocket and then put in a claim later.

Safety Wing is great value with monthly cover starting at $39. It’s super easy to use and it just renews each month. They have an excess of $250 and it’s simple to make a claim through their website. I currently use them as they offer me free cover for my son as part of my policy and I like that it renews on a monthly basis, so I don’t have to pay out a big lump sum up front.

I also use Travel Insurance Master for some short vacation type trips.

If you are doing shorter trips or an extended backpacking trip then Hey Mondo or Travel Insurance Master are the best option. If you are a digital nomad or planning travel of at least 6 months then go for Passport Nomads or SafetyWing.

Safety Wing Insurance for Nomads

This post was proofread by Grammarly