The digital nomad life may look pretty dreamy – and sometimes it is! But that doesn’t mean it’s without downsides. 

For all the positives of living nomadically, there are plenty of struggles that come with living a digital nomad lifestyle. And when they crop up, they can be pretty difficult. 

I’ve talked about some common digital nomad myths before, but today I want to share some real talk. Yes, I realise how privileged I am to have been able to create this lifestyle for myself. But sometimes things are really freaking hard. 

Here are nine of the biggest difficulties I’ve faced while living nomadically. None of them are completely avoidable, but I’ve shared the best ways I’ve found for handling them when they happen.

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Having just spent a month in hospital, I’m going to put health care and health concerns right at the top of this list. 

Being unwell is awful when you’re at home, surrounded by loved ones and familiar things. When you’re on the opposite side of the world, in a country where you know nobody, it really sucks. Like, really sucks. 

That’s happened to me twice this year – first in Peru and again in Australia – and both times were seriously hard. So hard I may have even considered hopping on a plane and calling it quits as soon as I felt well enough to do so. 

What to do about it: 

Make sure you have travel insurance! I’m not exaggerating when I say travel insurance has saved me a fortune on medical bills this year. I really can’t stress how important it is to have insurance when you’re travelling!

You don’t want just any insurance, either. I spent hours researching travel insurance so I could be covered for the worst case scenarios – and wouldn’t be caught out by any sneaky policy terms (like limits of the number of times you could travel in one year).

TRAVEL TIP: I wrote this huge post about which insurance I use and why.

I know travel insurance might seem like a total waste of money. I “wasted” around £600 in my first year of full time travel to make sure I was covered. But I made it all back again when I made multiple claims in my second year of travel. 

If you have a hard time coughing up the cash, think of it this way: if you have travel insurance, then either way you win. If you claim on it, you’ll save a bunch. And if you don’t, you can be grateful that nothing happened to you this year and enjoy your travels with complete peace of mind.


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Working in Perth Royal Hospital
Working from my hospital bed – not my favourite “office of the day”

Travel Disruptions

Delays and disruptions are pretty much a normal part of travel. One missed connection can turn everything into chaos, especially if you’re travelling for a project or have a looming deadline. Getting stuck in an airport isn’t always the end of the world, but it sure makes staying on top of work harder.

The problem is, you can never really plan for them. 

What you can do: 

While you can’t avoid travel disruptions, travel insurance 

Even better though, is thinking ahead when you book your flights. The flights you choose and the airlines you travel with can have a big impact on what happens in the case of delay or cancellation. If you’re flying in or out of the EU, for example, you may be entitled to compensation. 

Along with a few other flight preferences, I always try to book flights that will be eligible for compensation should there be a delay or cancellation. Then, if something should go wrong, you can at least recuperate some or all of the costs – something I’ve been super grateful for in the past.

It’s super easy to do this through a site like Myflyright because they’ll handle the entire process for you and you don’t need to open an insurance claim (and put next year’s premium up)! You simply enter your flight number, dates and ticket number and they take care of everything.

Having a lounge pass also means you can be productive when you’re in the airport – and get work done if there’s a delay – taking some of the stress away.

working on a plane
Not every plane has WiFi… and not every flight goes smoothly!


Visas, something you might have only thought of when planning a big trip, become an evergreen issue when you’re travelling slower. Your travels will ultimately be decided by how long you can stay in each country, so it’s important to know your rights and the rules.

Most countries are making it easier to get visas. While you used to have to go to the respective embassies in your home country, you can now get visas on entry, or online from anywhere in the world. I was able to get my visa for visiting Perth, for example, while I was in Bali. 

And then there’s the grey area of working online while you’re there. Most digital nomads travel on tourist visas, which is pretty much always the best option. As far as I see it, unless a country is going to offer more flexible visa options, there’s not much you can do about the fact you need to work while you’re there. And unless they’re going to kick out every tourist who checks their work emails while on holiday (because, let’s face it, employed people do that too), it’s always going to be a grey area. 

What you can do: 

Never overstay your visa. If you can’t extend it, accept it and move on. One of the beauties of being a digital nomad is that you can come back whenever you like. And if you really love somewhere enough that you always want to keep coming back, it might be worth looking into residency options.

As for working while you’re there… Generally speaking, as long as you’re not working for a company in the country you’re visiting, you should be totally fine. If you’re somewhere that explicitly forbids work in the country you’re visiting, you can always turn down or delay work for clients based there until you move on.


Probably one of the more obvious ones, digital nomads depend on a solid WiFi connection more than anyone. It’s not just a case of wanting to be online, but needing to if you want to be pay the bills. 

Luckily, we can live on a surprisingly small amount… but it’s still frustrating to have a deadline looming with no way to get connected.

What you can do: 

Choose a SIM card that covers as many countries as possible. I have two UK SIM cards that I carry with me: a Vodafone contract that covers 77 destinations around the world and a PAYG Three SIM that covers others, ready to top up when needed. A WiFi hotspot can also extend your coverage when mobile data begins to get pricey. 

It’s also really important to plan laptop days into your schedule and make sure you get everything done that needs to be done before you next have WiFi if you go offline for a while.

Minimalist remote desk

Time zones 

Jet lag isn’t the only issue with changing time zones. Sometimes you lose a whole day of work when flying east and you always need to think about time differences when booking meetings into the calendar.

Every time zone has its own advantages and disadvantages. In Asia and Oceania, you have a head start on the day. In Europe and Africa, it’s easy to schedule calls because work hours overlap with every country. And in the Americas, there’s always an incentive to get everything finished a day early so you don’t miss deadlines. I’m always super organised when I’m that far west! 

On the flip side, you might find yourself staying up late to take calls when you’re east, getting up early to take them west, and working extra long hours when you’re in Europe and Africa. And then there’s knowing how to manage client expectations when you’re hopping from time zone to time zone – something that can be pretty terrifying!

What to do about it: 

Use it to your advantage. If you’re in Asia and your clients are in the US, go out and explore all day, knowing you can take calls and answer emails in the evening. When you’re further west, enjoy being able to reply to all emails in one go after everybody else has packed up for the day. Sure, it takes some adjusting each time you move, but it’s generally pretty easy to get into a rhythm.

As for clients, most of my clients know I’m travelling but never really ask where I am. Sometimes they ask about my whereabouts to make conversation but it’s usually it only comes up when we need to book a call. If you don’t feel comfortable telling your clients, you can always take calls over Skype or Zoom so they never hear the international dial tone. (Side note, I’d always recommend being upfront about it. I’ve never had someone take it badly, but if they did I’d know they’re probably not a good client for me!) 

Other than that, I try to send any work emails as close to UK work hours as possible – and it definitely helps me switch off for most of the day! For me, it’s more about setting boundaries than it is about time zone differences. It’s not uncommon for my self-employed clients to send me an email on Sunday morning or Friday night, so why would it be any different the other way around?


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Building and maintaining relationships becomes a whole new battlefield when you begin travelling full time. Whether you’re single or in a long-term relationship, travelling full time comes with many challenges. And then there’s friendships and the lack of a regular social circle.

What to do about it: 

Unfortunately, it’s something that takes a little time and effort. Your relationships will look different as a digital nomad – in both good and bad ways! – and getting used to it is something that only comes with time.

It might take your friends and family a while to adjust to your new lifestyle, so try to be patient with them. You also might need to make the effort to initiate contact with friends back home – but I promise they’ll be glad you did. The biggest tip I can give is to schedule in calls as often as possible and soon it will become a normal part of routine. It might feel a little weird catching up like that the first time but it’ll soon become normal – and something you can both look forward to.

As for having a regular social life, I’ll be honest: it’s HARD. Facebook groups, co-working spaces and actively seeking out events in each destination make it possible, but it’s never the same as having a regular social life in one place.

That said, I’ve made some really amazing nomad friends on the road. It might be harder to maintain old relationships, but it’s easier to make new ones because you already have so much in common when you meet other nomads!

Ibiza sunset at Platja Pinet

Having an address 

Lots of digital nomads, when pushed, will still insist they don’t have an address. But unless you’re willing to give up your credit cards, travel insurance and passport (which simply isn’t possible if you’re travelling!) then you need a permanent address. Even if it’s just a virtual office or post code, everybody still needs some form of legal address. 

Paying for a house back home while travelling full time is a good way to waste money. So what should you do if you don’t have any kind of lease or mortgage? 

What to do about it: 

It’s possible to have an address without actually living there, so do whatever’s easiest for you. There are essentially three options. The first is to use a friend or family member’s address. The second option is to find a cheap lease somewhere and go back several times per year. The third, if you’re able to, is to get on the property ladder and lease it out on Airbnb while you travel.

Managing paperwork 

Services like banking are becoming more and more digital-friendly, making it easier than ever to manage, but there are still issues that pop up from time to time. Carrying paperwork with you isn’t an option, for a start. And then there’s the issue of receiving any important letters when you need to – especially if you don’t know they’re coming.

What to do about it: 

Most banks offer a paperless option, which means you don’t need to worry about any paper letters going unseen. Ask your bank to set everything up so you receive important notices online.

When you do have paperwork, keep digital copies of everything somewhere safe. I use Google Suite and Amazon Photos. You might want to have access to passwords, bank details, your passport, medical records or anything else you would typically keep hard copies of. You never know when you will need it!

RELATED READ: The best bank accounts and cards for saving (and making) money while travelling.

Keeping things safe

When you travel with all of your possessions, you increase the chances of things going missing or getting stolen. And when you live out of a suitcase, you tend to only own things you care about.

What to do about it: 

The best thing you can do is be smart when you’re out and – you guessed it – make sure everything valuable is insured. Avoiding flashing things around and, if you can, use an anti-theft day bag like this one.

Generally speaking, living nomadically has made me more of a minimalist, which has made me less sentimental about possessions. That said, I still use a suitcase with a padlock and it definitely helps with peace of mind while travelling. I use a Samsonite case with a built-in lock and it’s been a game changer. For shorter trips, I also have an American Tourister cabin bag with a built-in lock. Both are TSA-approved in case your bags are chosen to be searched.

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