Nomads Around The Globe – Interview With Olivia Round Town

My name is Olivia Round, I’m a 23 year old journalist and I set up my blog Olivia Round Town a few years ago while I was living in New York. I began modelling at 15, and when I wasn’t on the catwalk, I was in the pit shooting runway shows and street style. After 5 years in the fashion industry, I found my love of travel became my priority and people began asking questions about my ability to hustle travel deals and find all the cool spots in each town around the world, which is why I love to share my tips on both my website and social media.

I spent many years working in traditional news rooms as a journalist, but made a spontaneous decision to leave my desk job and go travelling, and I have been working nomadically ever since! As a freelancer, I create digital content, articles video clips and work as an on-camera presenter for companies across the globe, which is what I was doing before, but now I have the freedom to go for a surf first thing in the morning, or book a last minute trip to Hawaii whenever I like. It’s definitely not an easy lifestyle by any means, but the freedom is definitely a major perk!

In my spare time I doing yoga, dancing, swimming, drawing, having potluck dinners with friends, and working on various creative projects.

I’m super passionate about sustainability and dedicating my life to advocating for a better planet. I have seen a lot over the course of my travels, and feel it’s important to write thought provoking, educational articles to encourage less introspection and more energy focused on foresight and the what’s happening in the world around us.

Name Of Your Blog & Link: 

Olivia Round Town 

What can our readers find on your blog? 

As a trained journalist, I like to discover the secret spots in each place I travel to around the world. I then share my top travel tips under “destinations” on my website. You can find information on what to eat, what to do, where to stay and what to wear from Kyoto, Japan to Oahu, Hawaii and everywhere in between.

I also offer my stealthy travel booking services to find you the cheapest flights and best accommodation depending on your budget and travel style. Check out this post: Adventure Planning 

Under the “Meet Olivia” tab, I explain how I live my nomadic lifestyle. This is a pretty popular topic as to many people, quitting my 9 to 5 to travel the world and work remotely was a rather radical feat, but I think it’s rad and would highly recommend my lifestyle if you’re prepared for hard work (met with equally great rewards).

When did you start your blog and why? 

When I had just turned 17, I left high school and moved to NYC to study acting and journalism. I was photographing New York Fashion Week for designer Anna Sui, and after taking all these images of the likes of Cara Delevingne and Bill Cunningham, I decided to upload them to my own blog, and named it Olivia Round Town after my own name Olivia Round. You might as well make use of having a funny surname, right?

After years modelling and photographing in the fashion industry, I found that I started shopping less and instead travelling more, which is why I decided to run with the travel blog idea. 

How difficult or easy is it to run a blog whilst living the nomad life? Any challenges? 

There are definitely challenges such as hustling enough work to pay your rent! However the benefits outweigh the risks and I would rather take up an offer of a week hiking in the mountains and swimming in onsens, than counting my pennies after working all week in an office. Also it means I can surf every morning before my work day begins during summer months!

Where was home prior to you starting the nomad life? and do you still go back? how often? how easy is it to return home whilst roaming the world? 

Home will always be New Zealand, and whenever I am away for too long I really miss it. While I’m overseas, NYC and London are my second homes which I use as a base to travel to different countries from.

How would you describe the term nomad life in your own words?

Being able to jet off at the drop of a hat with just your laptop and a backpack. In one word: freedom.

When did you start the nomad lifestyle and why?  Also how long have you been living this lifestyle? How long do you see your self doing this? 

I boldly left my stable job as the National Digital Editor for a radio station and began travelling again… I started in Japan for a month, followed by Hawaii, USA, Iceland, England, Barbados, Italy, Thailand, Bali, Vietnam… the list goes on.

Currently my boyfriend and I are working on our van in preparation to travel round New Zealand and explore our own beautiful country. It’s funny while I was in Iceland, I was often asked, “Why are you here? You have geysers, waterfalls, hot springs and glaciers in your own country?”, it’s not a bad point, we do have it all down under, so I’m excited to see it all as a tourist!

What are some of the pro’s and cons of being a nomad? 

Pros: freedom to pick and choose work that you believe is valuable and ethical; spontaneity to travel at any time; a gritty challenge to become the creative, entrepreneur, work hustler and administrator (be prepared for overtime); fun, exciting projects; you have the opportunity to see the world!

Cons: lack of government support for a “gig” lifestyle; no benefits or perks that usually come with a regular job; homesickness 

What types of places do you stay in when travelling?

Couchsurfing is excellent if I’m on a budget, and it’s a great way to meet locals. I host back home in New Zealand, so it’s a nice reciprocal exchange.

Hotels will kindly put me up courtesy of my blog.

Otherwise friends and family who live overseas will often let me crash on their couch!

The big question everyone wants to know – how do you earn an income to travel full time?  

Ahhh the big question! See more here:

Do you have any tips for people that want to start the nomad way of living? Can you recommend any particular countries to start with? Or what countries you started with and how you found them. 

Totally! Get in touch and I’ll mentor you: [email protected]

What types of things do people need to plan prior to starting the nomad life? How did you plan the nomad life? 

There was absolutely no planning involved. I booked a trip and thought, oh my gosh, what have I done! It didn’t take long before the initial panic left and I got carried away riding scooters round Bali and feeding elephants. You’re only on this planet once, so when opportunities present themselves, take them.

Have you had any scary or funny experiences whilst travelling? 

First night alone in NYC I heard gunshots right outside my Brooklyn apartment; In London I got pinned to a wall by a drunk person on a bicycle; I’m known for talking my way into any event, show or concert; I will always crash fancy parties; I hiked up an Icelandic mountain in a blizzard… in my Nikes, and only just found my way down through the white-out by following footprints; My friends and I ate food off stranger’s plates; We’ve pulled all nighters to save money on accommodation; and the best one… I speak in a different accent in every country.

How many countries approx have you lived the nomad life in? Did you encounter any visas or immigration issues? 

Visa’s are very difficult to obtain, so I tend to spend a month in each country before moving on to the next one.

As a full time nomad (what is your back up plan) if the money or work runs low?

My mother always told me to make sure I always have enough money for a plane ticket home (which is good advice for everyone).

Do you do use any freelance work sites to obtain work from? 

Unfortunately freelance sites don’t offer high enough rates for our New Zealand economy (it’s very expensive here as I’m sure those who have visited would agree) 

Instead I work as a contractor for different companies back home. I can give you the run down if you send me an email:

When you reach a particular destination – how do you find work? Do you have a strategy or do you try ad secure work before you arrive?

Craigslist haha – but seriously, they have some great creative content jobs.

What factors do you consider prior to travelling to a country for the nomad life? 

I have a list in my head of all the places I want to visit and just check each place off. But if a friend says, “Let’s go to The States next July” chances are, I’ll be keen.

Have you encountered any issues with adjusting to local customs or the culture whilst you have been travelling? What about language barriers has this been an issue anywhere? 

Of course, and you can’t expect each country to have your home comforts. I’ve spent weeks living on Oreos and peanut butter because there are no vegetarian options in a meat orientated country, but you just have to accept it and be a shrewd planner (or learn from your mistakes). It’s also important to learn some of the language to show the locals that you have made an effort, even if you get it all wrong, it’s polite. 

Do you travel solo as a nomad? If so what are the pros and cons of this? 

If I travel alone, I force myself to make 42 new friends on day one because I’m outgoing and thrive in a busy, social environment. Solo travel is great for independence as you have to manage all the little glitches and negotiate plans yourself, but it is always nicer to have someone with you to have a laugh or to pinch and say, “OMG are we really here right now?!”

Has been easy to make friends and socialise – whilst travelling around as a nomad? 

I will talk to anyone or anything that can respond, but that’s just me.

Do you have any money saving tips for flights / accommodation? Any recommended sites to book on? 

Couchsurfing and dedication to Skyscanner.

What equipment do you use for your blog or as part of your nomad lifestyle  e.g: drones, cameras, computers, editing software, tablets phones.

GoPro, Canon 6D, iPhone 6, iPad mini, Macbook Pro Retina.

What country are you in at present? How have you found the nomad life there? 

I’m home in New Zealand, we’re currently building our remote home before we hit the road in summer.

What has been some of your top highlights from travelling?

Diamond Head for sunrise on Waikiki in Hawaii – I went by myself and it was just so magical, sitting upon a rock with 360º views surrounding me.

-Taking my mum to Rome – we spent a spontaneous weekend there which was filled with laughter, lots of delicious food, and dancing with strangers in the square at midnight. 

– Diving off Phi Phi Island as a birthday present from my boyfriend. We saw sharks, turtles, Nomura jellyfish, nudibranch… it was incredible!

​* Google: Nomura Jellyfish, they’re taking over our oceans due to global warming and the decline of Tuna, which is one of the only fish higher up in the food chain who actually eat them. If there’s one thing we need to pay attention to ASAP, it’s these human-sized liability creatures!​

What is on your bucket list?

Visit Machu Picchu, swim with a whale shark, dive at Komodo, travel round South America.

How do you see the future of nomadism? 

We’ve come a long way from the traditional 9 – 5 job, so I think nomadism is a great way to establish a work life balance and give people the opportunity to work for themselves in a way that they will be productive and passionate.

Has being a nomad taught you any life lessons? If so please elaborate. 

It’s taught be to become an expert at time management. If you don’t get the job done, you don’t get paid – it’s as simple as that. I have also dedicated more of my time to helping people because now I have more time available to prioritise what is important to me.

Please share one quote you love. 

The worst someone can say is “no”.

If you want to learn more about how you can live the way I do, I offer mentoring services which you can enquire about via my blog – please give my page a follow and feel free to check me out on Instagram too Olivia Round Town 


I love helping others achieve their travel dreams and there are so many possibilities out there, you’ve just got to be determined, willing to help and accommodate others and not be afraid to put yourself out there, regardless of what others think.



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