Since I took up the digital nomad lifestyle nearly two years ago, there are certain questions I get asked a lot

And I get it – this lifestyle is still pretty unconventional.

It’s a lifestyle that intrigues a lot of people, even if they have no interest in becoming location independent themselves.

I’m always happy to answer any questions people have about being a digital nomad – yes, even how I make money!

There are some questions, though, that even the most brazen of people don’t dare to ask.

So, today I’m going to spare you the awkwardness and answer all of those questions lots of people have wanted to ask, but few actually go there.


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Do digital nomads pay tax?

I can’t speak for everyone, but I do.

I know people who aren’t resident anywhere and don’t pay tax, but I wouldn’t recommend it.

It’s still a very grey area and makes it almost impossible to get good insurance – something you definitely need as a digital nomad!

TRAVEL TIP: Check out this in-depth post to find out more about getting insurance as a digital nomad.

Where do digital nomads pay tax?

That completely depends on where they are a resident!

I know people who have companies registered in one country but are resident elsewhere and split their tax between the two, but most people choose a country to be tied to.

For me, that country is my home country: the UK.

My company is registered in the UK and I’m legally still a UK resident. That means I pay tax in exactly the same way as any self-employed British national, the same as I would if I lived in the UK.

Do you ever get lonely?

In short, yes.

Dealing with loneliness has been one of the hardest parts of being a digital nomad for me. I’m a (very introverted) extrovert, and struggle when I don’t have meaningful interactions. 

It’s easy to go to events and meet-ups, but it’s hard to really build any connections when you’re constantly moving.

Sometimes those meet-ups can feel even lonelier than not going at all.

The lack of community and social routine is something I really miss. I’ve found regular calls with friends and family, meeting up with friends while travelling and building a strong network of nomadic friends has really helped.

But nothing can ever beat the kind of connections you have when you live in one place.

las palmas segway tour gran canaria
I thrive on press trips and conferences because I get to spend quality time with friends!

Do you ever feel guilty?

Yes again! 

It usually comes down to one of two things: guilt that I’m living selfishly or guilt that I don’t go home much. 

The first is probably the hardest one to deal with. It’s kind of silly that I should feel guilty for living my life the way I want to – especially when so many people don’t – but it happens.

It’s one of the reasons why I’m now focusing on helping others create the lives they dream of, too. 

Although I feel guilty about missing birthdays, weddings and random days out, that guilt has subsided with time.

The truth is, I see some of my friends and family more now than I did when I was living in London. And when I do, the time we spend together is much better and I value it more.

So, even though I don’t visit home much, I definitely make the most of it.

Have you thought about going back to a “normal” life?

All the time!

It’s usually just an odd curiosity about how my life would have looked. Would I still be working in the same office? Going to the same gym? Hanging out with the same friends? 

It’s easy to dwell on the “what if’s” but I just remind myself that I made the right decision. 

When things all seem to be going wrong, it’s easy to think it was a mistake.

But, ultimately, the struggles are all part of the journey and I wouldn’t trade it for anything. 

The truth is, the longer I’m away, the less I can imagine going back to a “normal” life because it feels so alien to me.

It’s a scary thought, but it reminds me not to take the freedoms I have for granted.

How often do you worry about money?

I usually only worry about money when I’m worried about something else. And, for some reason, I only seem to worry about money when my finances are looking their healthiest. 

I don’t remember worrying about money when I first started travelling – perhaps because I had a safety net of savings – but I’m sure I must have.

As I began to earn more, that was when the worry really set in. And as soon as I began earning more than I did in London, the worry hit its peak. 

I honestly couldn’t tell you why that is but I think it has something to do with everything feeling a lot more “real”. 

Do you want to settle down one day?

That depends what settling down means… 

I plan to buy an apartment in Europe within the next year or two, and I’d love to eventually own a few apartments in my favourite cities across the globe.

Right now, that would be in Portugal, Cape Town and maybe Taiwan

I can’t see myself working for someone else ever again, and I can’t imagine having kids.

I’d definitely love to get a dog, though, so that’s probably the thing that will lead to me staying still for a while! It would also be nice to have more of a social life and join a gym or fitness class long-term.

Looking out at a view in Patagonia

Do you still enjoy travel as much?

This is a tricky one. I definitely have days where I wonder if I still love travel or if travelling full-time sucks the fun out of it.

But, in the end, there’s nothing I love more. 

Sometimes I crave staying in one place for a while and forgetting travel exists.

I’ve learned to be okay with that – and I’ve also learned to make time for that. But it doesn’t take long for me to get itchy feet again!

Do you enjoy the trip, for the most part?

There are always things I enjoy and things I don’t on every trip.

I’d be lying if I said I don’t have to make an effort to enjoy it sometimes – it’s just easy to get caught up in the pressures of filming, taking photos and making notes for blog posts.

Since I switched the focus of my YouTube channel away from travel and back to its original purpose, it’s certainly made things easier. I can now take time to enjoy everything, rather than frantically trying to get all the shots I need.

That said, unlike in the past, I don’t feel the pressure to enjoy – and make the most of – every minute anymore.

When travel is your lifestyle, you can’t expect to enjoy it all, and I think I gave myself a hard time for a while. 

I no longer mind if I miss out on things because keeping a good balance is my priority.

Plus, you can always go back to somewhere, like I did with the Philippines this year – it’s nice to have a reason to!

How often do you just want to give it all up?

I think about it way too often! Sometimes I even think maybe the sweaty tube, gloomy weather and unfriendly London streets weren’t so bad… but I quickly snap out of it.

There are lots of highs and lows of living a nomadic life, and it can be easy to doubt yourself.

The next day, though, I’ll probably be shouting about how I never want to “settle down”.

I’ve only come close to giving up once, and that was because I was having a VERY bad week.

I’m glad I didn’t. It’s important to take step back every now and then when you work for yourself, but especially if you work for yourself and are constantly moving around.

How do you protect yourself from theft and also not offend people?

I feel like I’ve become more cautious over time, and I’m not entirely sure why.

Perhaps it’s because I now know what I have to lose, but I have to remind myself that everything is replaceable except my health. 

Of course, I have insurance for my cameras, laptop and valuables (I’ve had to claim on it a couple of times, too).

But, even when I had to travel to Iceland without my usual laptop, it really wasn’t that bad. 

I always err on the side of caution and don’t worry about offending people – I’m not sure how I would – especially if I’m not going to see them again.

Ultimately, though, I’ve accepted that sometimes things will go wrong – and that’s just a normal part of life.

travel video tips
I’m always cautious with my gear, but I also don’t want to miss out on a great shot because of it. Otherwise, what’s the point?

How do you go about prescriptions?

I used to stock up every time I went home, but my current doctor refused to give me more than 30 days of medication.

He told me it’s not possible… even though all of my previous doctors would give me 6-12 months at a time so I could travel.

So, I now pay for my prescriptions and order 12 months at a time on Superdrug’s online service (available in the UK).

I know I could get hold of everything abroad, but I prefer to just stock up and have it with me so it’s one less thing to worry about.

It costs more than it would from my own GP, but I’d rather pay £5 per month for the convenience.

How do you tell your parents/family that you want to be a digital nomad?

For me, this was BY FAR the hardest part about transitioning to the digital nomad lifestyle! It’s hard to explain to anyone who’s not familiar with the concept.

I knew I was going to have to show rather than tell if I wanted people’s support.

I’d say it took a few trips home before it became “normal”. If anything, I think it gave me extra motivation to make it work hard and make this lifestyle work for me – which was a great thing!

Now, I think everybody is just used to it. 

Unfortunately, there’s no easy way to deal with people’s reactions except to work hard and show them it’s possible.

It might help to dispel a few digital nomad myths, too. Once they see how happy and successful you are, though, they’ll come around!

Just remind yourself: they only worry because they care about you. Any negativity surrounding your decision comes from a good place, even though it’s hard to hear.

Just make sure you’re always living the life you want and being true to yourself. Everything else will fall into place eventually – I promise!