Digital Nomad Josh Bender. Insights and Surprises from a Lifetime of Travel

05 May, 2023 | Blog, Interviews

Josh Bender, a seasoned traveller and digital nomad, shares his insights on the skills and experiences he has picked up along the way, including a solution-oriented approach to problem-solving, letting things slide, and the benefits of minimalism, as well as his surprising experiences of being recognised on the street.

Antelope Canyon, Arizona, 2017


Josh, tell us something about your early life and how your interest in travel developed?


I always had a strange fascination with maps when I was a kid. As a 5-year-old I would find myself gently flicking through an oversized book of maps from all over the world. I would imagine what life was like in these far-flung locations. My dad also had a collection of National Geographic magazines that would keep me engaged for hours. I learned a lot about cultures and customs different to what I grew up with.

Little did I realise that this fascination would turn into a lifestyle of travel decades later. Not to mention, I have a pretty good sense of direction. 😉

Sand Hollow State Park, Utah, 2017


Monument Valley, Utah 2017


Which traits of character help and interfere you while travelling? Tell us about your personal travelling style, please.


I’m always pleasantly surprised by the wide range of personalities I meet along the road – from extreme extroverts to isolated introverts. But regardless of personality, there are several skills that can make travel much, much easier. Some of these can be learned anytime, others only develop at the coalface – when the rubber hits the road.

A solution-orientated approach to problem-solving is a must. The constantly changing nature of travel throws challenges at unexpected times. Rather than throwing a tantrum or lashing out, taking a deep breath, recomposing and looking for a logical, well-thought-out plan forward – will make life much easier.

You also have to learn to let things slide. Another way of saying that is “pick your battles carefully”. I’ve learned to accept the things I can’t control and when there is a point of conflict, carefully consider if this is worth escalating. Very rarely does it need to. It might mean a slight inconvenience or extra cost, but your sanity and peace are worth a lot more.

I try to put these 2 concepts into practice as I travel. I’m not perfect by any means, but always try to improve. 

I find that by sweating the small stuff less, I have more energy and am more open to soaking up the amazing things around me.

And being more reflective by nature, I enjoy taking the time to delve deeper into the destinations I visit – dig up the history, dive into the culture, and try as much of the local food as possible.


Hiking through The Wave, Arizona, 2017


Hiking through The Wave, Arizona, 2017


Please share some special stories from your travels, that have really shaped you.


It is hard to narrow these down – there are so many stories!

During the first couple of years of my nomadic travels, I was changing a lot as an individual and gradually shedding a lot of social expectations. One example of that was reflecting on my work ethic after my first long stay in Bali back in 2012. I had grown up in a culture that dictated you had to work a certain number of hours per week otherwise you were lazy.

That same culture also suffered from the side effects of excessive working… poor work/life balance, strained relationships, and mental health challenges. By being immersed in the slower Balinese pace of life, I re-evaluated what was really important and started questioning what I was taught. This journey is shared in more detail in an article I wrote. It also dovetailed into the concept of minimalism – living more simply to spend more time doing what matters most.

On the fun side, one particularly memorable experience was spending Halloween with 2 friends in Tokyo. I only had 1 spare evening in my itinerary, and they took me out to Shibuya Square. We found tens of thousands of Japanese dressed up in all sorts of outrageous, colourful costumes, celebrating the holiday. It was completely surreal.

Dressed in a Mike Wazowski outfit (from Monsters Inc), I was at least 1 foot taller than every other person in the square. I can’t count the number of times people asked me to stop and take a photo – we all ended up in a random interview with a TV news journalist. Sometimes the things you don’t plan for become the best memories.


Sand Hollow State Park, Utah, USA, 2017


Krabi, Thailand, 2018


What were some of your biggest surprises on your travels so far?


Firstly, I’m still surprised I’m going after 10 years. I didn’t really have a fixed timeframe in mind but also didn’t expect that this would be forever. At some point, I’d set down in one (or more) home bases. But life evolves and the path unfolds one day at a time and I’m still going.

I also didn’t know that my blog would turn into a full-time business when I started out. That was a pleasant surprise.

Being recognised on the street several times really surprised me – the world is a big place and my blog is one out of millions. What’s the chance that someone would spot me?

Some years ago I transitioned to a plant-based diet which would have really surprised Josh in 2012 (I was addicted to cheese!). 

I think the COVID-19 pandemic caught a lot of digital nomads by surprise. In early 2020, I would downplay it and say to friends it will blow over soon. But pretty quickly things escalated and lockdowns ensued. I didn’t see that coming. And definitely didn’t expect it would be 2 years before the world started returning to normal. But I learned a lot from the experience, and am grateful for that.


Hiking in Scotland, UK, 2019


Meteora, Greece, 2019


There is a stereotype that travel is only for free and wealthy people. For many,  dreams about travel remain a dream. What would you recommend for people with a low budget, for sure, there are ways to see the world and still not spend a fortune.


Any dream can be worth pursuing. But having a realistic picture of the dream is the most important thing.

There’s a big difference between a dream and a fantasy – a dream requires work and sacrifice, and a fantasy does not. 

I had a dream to become an architect when I was a teenager but after doing 2 weeks of work experience I discovered that the job entailed a very different set of skills than what I pictured in my mind. I just didn’t know.

So whatever your dream is, learn everything you can about the pursuit. Immerse yourself it. A goal is different… it’s always outside yourself. So started to become the dream. It’s not about waiting until the circumstances are perfect. It’s about learning to become someone with the character and skills to carry the dream. Sometimes it’s glamorous. Sometimes it’s mundane. And other times it can be downright uncomfortable. But that’s what the dream entails. 

People who think they don’t have enough money to pursue their dreams will never have enough money. A scarcity mindset will breed more scarcity. Managing a budget is an essential life skill, so if you can’t do that yet – start there. Reduces expenses until you have enough savings to get on the road. If you can’t be accountable with a little, how will you be with more?

Personally, I prefer mid-range travel, not super luxury and not ultra-budget. But during the COVID-19 pandemic, I learned to get by with a lot less. It was a humbling experience. I already practised minimalism, but still managed to find new things to shed which freed up my resources and time. This kept my travel dream alive.

The question of having enough money to travel is just a matter of priorities. You’ve already got the money right now. But what you choose to spend it on will determine what dreams you achieve.


Waterfall in Langkawi, Malaysia, 2020


Which places would you come back to and why?


Again, there are so many answers. I really enjoyed the Greek Islands and will definitely go back. The laid-back ambience, delicious food and gorgeous scenery make it a heaven on earth.

I’ve been to the US a number of times, but I will definitely go again. The national parks are amongst the best in the world – especially in Utah and Arizona.

I only spent a little time in Portugal and the south of Spain, so that region is high on my list of places to explore further.


Phi Phi Islands, Thailand, 2022


Phi Phi Islands, Thailand, 2022


Splashing around in Maya Bay, Thailand, 2022


How do you choose the next country or city to visit? Is it your goal to visit all countries in the world?


I’m not interested in ticking boxes or completing a list. I travel because I love it – not because I’m trying to impress anyone. This isn’t a race for me, it’s a slow, unfolding journey.

Choosing the next country can be tough. 

For inspiration, I like to use – an essential tool for every digital nomad. I explained how I used it in my article about finding cheap one-way flights. Usually, flights can be one of the biggest expenses of travel and this tool helps cut down that cost dramatically. 

I also subscribe to a number of travel newsletters including Dollar Flight Club.

The reasoning I use to choose the next destination has changed a lot over the years. Early on I wanted to see as much as possible. Now I go a bit slower and will travel out of my way to meet friends to attend a concert. Or dare I say… find a mouth-watering vegan donut.


Hua Hin, Thailand, 2018


Datai Bay, Langkawi, Malaysia, 2021


Phi Phi Islands, Thailand, 2022


Finally, our signature question – if you could invite any 4 people to dinner, from any period in history, who would your guests be, and why?


The first would be Leonardo da Vinci. He’s one of my favourite historical figures – as the archetypal “creator”. We think of this as a modern trend on the internet, but he was doing it centuries ago. While he’s a genius, he’s also very relatable – trying to chase his dream of being a “serious” engineer.

Next is Socrates because you can guarantee the dinner conversation will be lively and dramatic. I’ll just have to check his pockets for poison in case disagreements get too heated.

I couldn’t miss Will Ferrell. He’d bring the laughs and would go toe-to-toe with Socrates. 

And finally, my dad. He passed away in 2014, and I’d love for him to see the person I’ve become. So much has happened since he passed that I wanted to share with him. Even if it’s just for an hour, I’d rather have a deep philosophical conversation with him over anyone else in history.


Alter Of Zeus, Çanakkale, Turkey, 2018


Splashing around in Maya Bay, Thailand, 2022

P.S. Make sure to follow Josh on facebookm, twitter and read his blog