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Taking Risks and Embracing Adventure with Olivia Poglianich, Marketing Executive at Outpost.co


Taking Risks and Embracing Adventure with Olivia Poglianich, Marketing Executive at Outpost.co

New York City born and raised, Olivia Poglianich has always had a strong sense of her own personal values, including admirable ambition and - occasionally to her disadvantage - unwavering honesty. Following graduation, she found herself doing work, which wasn't right for her and knew that the only way out was to take a bold risk and escape her comfort zone.

Well, it paid off, and she is now designing her best life as a marketing executive at coworking and coliving space provider, Outpost. I wanted to get an insight into how she maintains such a positive outlook, despite choosing a life which would be daunting to so many people. Her story represents a realistic path to living your dream location independent life, and she offers plenty of travel and career tips to help set you up for success.

"Those who do not risk, cannot win": it's etched into your passport and is clearly a mantra that you stick to. Why is this quote so important to you, and how are you able to be so bold in your approach to life, work, and travel?

A foreign friend of mine was flipping through my passport on a bus in New Zealand as she read that out loud to me. It was right around the time I made my first abrupt life change, so it stuck.

It represents that moment where I first caught a glimpse of life on the other side of my comfort zone. I was only meant to be traveling for three weeks but felt such a strong pull to keep going and follow my heart, not my head. It probably sounds cheesy, but that quote helped me abandon my attachment to what I was "supposed to be" doing at the time, which was working a low paid corporate job. I knew there was a better way to live, and I wanted to test it out. So I changed my flights and showed up in Australia with my backpack. Then I figured out the rest as I went along.


Risk taking will eventually lead to mistakes. Can you think of a sticky situation you have gotten yourself into?

Absolutely. There are quite a few!

How did you cope - mentally and emotionally - and what practical steps did you take to get yourself out of that situation?

Self-awareness and forgiveness are pretty important here. Realizing when I make mistakes is the first step; admitting them to other people is the second, and finding ways to avoid making the same mistake twice is the third - and the hardest.

I've always prided myself on being honest and opinionated, but especially when I was younger and less experienced, that skill was also perhaps to my detriment. I hated my first job out of college. It was different than I expected and outside of my skillset. I tried to push through late nights staring at excel, but those short six months felt like an eternity. Impatient and miserable, I decided to ask HR about switching me to a different department, but they responded by laying me off.

I look back on it and think about it more from the other side. Why would an HR department want to invest in relocating someone who was less than six months out of college? I don't regret being honest with them, but I could have taken a more considered approach and received a more positive response.



So you lead the brand strategy at Outpost. What is Outpost, and why is it unique?

Outpost is a global coworking and coliving space that champions a new way of working and living. So many coworking spaces have popped up lately, all offering varying strengths of WiFi and creature comforts to help freelancers work the gig economy.

What I love about Outpost is that the whole team seems to get that coworking and coliving are about more than that. Our company values are growth, exploration, and connection, which are in line with my personal values.

The hiring staff there wanted to get to know me as a human being. Outpost is such a great place to work because it's the kind of environment where new ways of doing things are championed, ideas are encouraged, and people are listened to.

Outpost's slogan is #designyourbestlife, which I think we are really enabling. I mean, I'm a perfect example of this. I've been working remotely for them for three months, traveling around South East Asia the whole time. I went to visit the team and asked if I could have some time at home to see my family before making the significant longer-term move to Bali. They totally respected my wishes.

#Designyourbestlife is especially true for our members. All of our coworking spaces are open 24/7, so you can channel your inner night owl or early bird and get things done at your own pace. There are many organized events to fuel connection. For instance, coders find designers and build their dreams together, and life coaches trade services with digital marketing gurus. I love hearing stories about our members forming enriching connections. They make lifelong friends and sometimes even find love.

So many people think that they are incapable of succeeding as a digital nomad. Why do you think this is and what is the single best piece of career advice you can give to inspire others to take a path similar to yours?

I think a lot of people are just afraid. There are no rules to follow. That's what makes the crazy ones successful - we like that ambiguity. But for most people, it can be hard to live in this new fuzzy world without a concrete sense of rules and responsibilities.

We've already covered my big belief in taking risks and just "going for it," so my next piece of advice would be channeling and guiding your inner ambition. That's the key to succeeding in this off-the-beaten-path kind of lifestyle. With flexibility comes a whole new set of responsibilities. You learn how to do your own taxes and become more financially savvy. You become more organized and hold yourself even more accountable. You become more patient with slow internet connection or things not going according to plan. In fact, you may even start to embrace those things.

When it comes to ambition, it's all self-guided. There's no one telling you when you have to start working or when you have to clock off. Even if you're a remote employee for a large company, you have so much autonomy now. Some people may use that as an excuse to allow themselves to slack off. Other people may run wild with their ambition and find themselves in the same circle of overwork and overwhelm - just, maybe in Bali instead of NYC.

Without enough ambition, you probably won't make it. I know that sounds harsh, but a dream is just a dream unless you have a plan to make it happen. Yet the flip side of that is being TOO ambitious. Never knowing when to slow down, to unwind, to take a deep breath and allow for some "me" time. To put the work away and shut off. That's the catch 22 - finding this balance.

Ask yourself why you want to go remote in the first place. What does your vision of being a digital nomad look like? Then find ways to make that vision a reality.


Your Instagram profile reveals you to be a relentless explorer, so you must have some tips you've picked up along the way. What are your best travel and packing hacks?

Packing cubes! They help save lots of space and make packing up my backpack take approximately 10 seconds. Vacuum seal bags, however, tend to retain nasty smells.

Microfiber towels - They dry quickly, don't smell and they're super lightweight. I'm considering getting a second one so I can use one for beaches and waterfalls and another for the shower.

Clothes: they should be simple, dark, neutral colors, and non-patterned so they can be reworn without people noticing. Keep them rolled when packed and carry laundry powder for sink washing.

My carry on: a shawl for chilly planes, a reusable water bottle, a bamboo straw, chargers, noise-canceling headphones, and my travel journal for noting down inspiration or painting the scenes out the window.

Sum up your philosophy of travel in three words. Why do you believe this is the best approach to take?

My favorite travel quote - "Buy the ticket, take the ride" - is six words, but I'd sum it up in three like this: "Sure, why not?"

It's a philosophy of spontaneity; a bit of impulsivity in buying the ticket and just going. It's all about the "ride" too. It's not "go to your destination and take lots of pictures." Life is about enjoying those small moments of getting from point A to B, those people you meet along the way, the hours spent waiting in an airport or sitting on a delayed bus, feeling a sense of presence and enjoyment in the here and now.

It's also about being agreeable. Saying yes to things and being positive about the intentions of others seems to get me into more favorable situations than not. My approach is to let my guard down and be kind to strangers - let them in on the adventure!

It all starts with taking that first leap into the unknown. Living a bold life will lead to mistakes, but success depends on being able to learn from these pitfalls. As perfect as Olivia's life seems, she is not at her final destination. Her journey will continue, as she develops further into the ambitious, yet open and kind, person that she is inspiring others to be.

Written by Thom Brown






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