Olivia Poglianich on the Rewards and Realities of Nomad Living

‘Start spreading the news, I’m leaving today…’

For anyone who hears the old and famous song New York, New York, you know it’s a call to the Big Apple. For Olivia Poglianich, her experience was different. As a native New Yorker she knew she had so much of the world within her hometown – but still the road called her. 

Just a few years after graduating from Cornell University with a Bsc in Communication, Olivia set off travelling. Not because of the absence of what New York held, but because of what the rest of the world offered. But never was there the intention to be away from the Big Apple for too long.

Like so many new plans made on the road, Olivia’s decision to move into being a full time nomad was one that developed over time. Initially the thrill of travel was her key motivator. In December 2017, Olivia set off on what was supposed to be a 3 week holiday to New Zealand. It was to be only 3 weeks with a full time job lined up and awaiting her back at home.

But before too long Liv realised she was a traveller that required real immersion to really enjoy travelling. That fun as it may be initially, overtime buzzing the tower just leaves you sad you didn’t have a chance to pause and take in what you passed by. And that required finding a career that’d work all over the world – and making a success of it. 

After New Zealand, Australia followed. Then Fiji, Bali, Malaysia, Hong Kong, the Philippines, Cambodia, Laos and Thailand. Along the way a quick 3 week trip had turned into an odyssey. Simply returning home and setting down her passport was no longer an option. 

In pursuing a nomadic career Olivia has built a business, a personal brand that can connect across continents, and a capacity to work with an independence not only within one workplace, but across the whole world. 

As a strategist working in the digital economy, Liv’s typical workday sees her serve a mix of clients locally in-person – wherever ‘locally’ happens to be for her then and there – and globally via remote work. It has given her the opportunity to travel freely, enjoy financial stability due to her diverse client book, and also build her own identity in her industry that she can shape as she desires.

But opposed to any suggestion that nomad living and remote working is simply ‘beautiful one day, perfect the next’, Liv wants all thinking of this path to understand the grit, toil, and doubts that must accompany the moments of joy, freedom, and fun. 

Liv also wants to ensure anyone who is considering following her path looks at it as a real possibility, but also one with a set of unique challenges. This writer was in touch with Olivia for an interview and insight into her take on this emerging industry. The following is a transcript of our conversation. 


Olivia Beach

Liv feels a nomad’s life means daily deciding ‘What’s next?’ . Also running to the horizon occasionally. Image: https://www.instagram.com/lostwithliv/



EK: It’s great to be speaking with you, Liv. I know you’re passionate not only about this field but also seeing a clear-cut perception of it in the public eye. Let’s begin with a open question: what is the biggest misconception you feel people have about the industry you work in? 

OP: I think the way the lines blur between remote work and being a digital nomad is one of the biggest factors. There are people who live and work in the city they’ve grown up in who are considered remote workers, and then there are people who work many odd jobs along the way while travelling. 

I think a nomad is neither of those. The simplest definition is someone who is travelling indefinitely while still working at their career. Of course there may be trips home along the way, and contracts and jobs will often stop and start, but I think that those who travel with these two goals in mind fit the metaphorical “mould” of a digital nomad.

For anyone who also wants to pursue this path I’d ask them to look into opportunities that offer them the flexibility to work from anywhere, while also imploring those that do already have a flexible work environment to actually get out there and leave their city or country. That’s the balance.

EK: I understand your evolution from travelling for pleasure to permanently travelling wasn’t an overnight one. Looking back, where do you feel the desire to turn this into a permanent thing came from? 

OP: I think the travel bug was always there for me. I can trace it back to a 6 week trip I took with my grandparents to Italy when I was 11. But I only feel it became a realistic possibility for me to become more than something I’d do for 2-3 weeks at a time when I was on the road in New Zealand. It sounds cliche but as I looked out at the breathtaking landscapes on many a long car ride, I start to re-evaluate what I really wanted out of life. So I took baby steps to start imagining those possibilities and began to tap into the online gig economy as a means to fund my travels with a few jobs related to my career.

As I started to pick up more gigs and one off projects, I began to see the benefits of the flexibility of this lifestyle-I could focus on diverse work that was always interesting, had full ownership of building my own brand and began to grow my income independently instead of being exclusively confined to just one job Monday to Friday. That was only amplified when I moved to Australia and got to pick and choose which agencies I wanted to consult for (and how long I wanted to stay). 


EK: You have really made authenticity a big part of your business and brand, and you want to see a really accurate picture of nomad living held by those thinking about doing it. What would you say too few people understand about the realities of nomad living? 

OP: Well there’s so much of course, but I guess three things really come to mind. The first is that nomad living really is like starting any other business. You have mobility, you may have more freedom, and you may even have a head start if, frankly, you speak native English and come from a country with a strong passport. So just like any other business, the age old advice of having financial security applies. You don’t know how long it’s going to take for you to secure that first big, steady contract. You may run into unforeseen costs along the way and will want to be in a position where you’ve saved up enough to protect yourself from a major monetary set back. 

Second, there’s no getting around the fact that while the day to day nomad life is full of variety, novelty and excitement, there’s the huge trade off of uncertainty that comes with it. This uncertainty isn’t for everyone. And sometimes you’ll miss the “comforts of home” especially when things that used to be second nature to you wind up taking so long to accomplish on the road (like finding a good doctor you trust for example). 


Liv loves what she does but as her Instagram Stories series ‘Life’ shows, the joys and common challenges like rickety trains and spotty internet remind her of a regular 9-5’s value. Image: https://www.instagram.com/stories/highlights/17976460711206819/



Finally, relationships can be a big challenge. It’s all fun and games to have all these enriching experiences in new places with new people, but the sad part about all these connections is how fleeting they can be. Its an inevitably of this lifestyle. Sure there’s always FaceTime and email to keep in touch. But unlike meeting people in your hometown where you have a regular schedule and proximity to build a connection over time, as a nomad many people will be regularly coming in and out of your social circle. It’s a weird feeling to connect so deeply and quickly with people, only to find that after 2 weeks, a month, maybe a few months at best, you go on with your lives and move your separate ways.

But I wouldn’t want any of these things to deter people. Because really with a positive mindset you can absolutely have an amazing time living as a nomad. You won’t ever be bored staring out the window from a cubicle. Things always tend to work out with a little patience and flexibility (You usually can find a good doctor in the next town if not in the one you’re in, for instance) Even if you don’t stay in Bali or Chiang Mai or Budapest together forever, you can make friends from all over the world that always have a couch to sleep on if you’re in their neck of the woods. 

But just as anyone who is a creature of habit craves stability, certainty, and their close friends always being in reach for a hug, I would suggest really thinking carefully about nomad living before taking the plunge. I’d save up some annual leave and try it for a month over the holidays before buying a one way ticket. If you find after the trial it’s for you? You may never want to stop!


Leaving Behind the Old Perceptions

While Liv embraces the nomad life, like anyone else she has family, friends, and familiarity back home in New York that she thinks of daily, and misses accordingly. But she holds while “indefinite” travel  may one day find a definitive calendar date to conclude on, the experience of nomad living has also changed her perspective on life and time, regardless of how long it will continue to last.

“I loved growing up in New York. And feel grateful to have had so many opportunities that the United States offers. My career today isn’t a rejection of that, but an embrace of the very best of its spirit. For generations, we’ve been in the habit of rushing to ‘tick the boxes’ like finishing high school, going straight into college, then getting a full time job and working your way up to the career path you love… I don’t say that’s wrong.”


“But for me, I’ve found midway through that journey, as I’ve been able to distance myself from the pressures so obviously inherent in a system that says ‘go go go 24/7,’ I’ve found what I love, and I’m ready to work hard to grow it. My worldview is still illustrative of my life and background, but having seen so many cultures and different traditions around the world in my travels, it’s given me the confidence to believe I can break new ground here.”

“I’m passionate about people seeing the realities of nomad life not because I want to discourage them from pursuing it, but because I want them to experience such an enriching lifestyle, too.  Just because we’ve always accepted that many new businesses fail, I think with the right foundation and strategy we can change that perception too. And once you look at nomad living with clear eyes and say yes? I think you have every reason to be confident you can make a success of it.”


Olivia Street

Liv’s travels see her venture to some very remote places. But she does find time along the way to snap some ‘on point’ urban shots too. Image: https://www.instagram.com/lostwithliv/?hl=en



The Journey Ahead

When it comes to the value of travel there’s an old and popular adage, “the world is a book, and those who don’t travel only read one page.”

Liv travels, works. Doing both well, with real passion and commitment.

Yet she also writes, in doing so helping build her business and audience further. Certainly that’s commendable in and of itself.

But she is also creating a valuable record on the reality of remote work in the 21st century, for all its trials and tribulations.

Just as we’d all wish her safe travels, so too may we the same for her ongoing efforts to drive new awareness on the phenomenon of nomad living.


Olivia Poglianich is a New York-born strategist currently moving around the world map. To learn more about Liv’s business and read her regular column on nomad life visit lostwithliv.com/ 


Ed Kennedy is a journalist and ghostwriter from Melbourne, Australia. Contact Ed via enquiries@edkennedy.co on Skype or LinkedIn.

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