Remote Works and the Future of Work with Ali Greene | TNN56

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Episode Summary

The nature of work is changing faster than ever as workers and businesses adapt to economic challenges like public health crises, technological disruption, and climate change. Even though we didn’t expect the future of work to come so quickly, the shift to remote work and the emergence of virtual workplaces are forcing us to adapt to these changes. Constantly expanding technology, and immensely powerful social trends will shape the future of work, but which direction it takes is almost impossible to predict.

Ali Green, author and digital nomad turned expat, joins our hosts Andrew Jernigan and Allen Koski for another exciting episode of The New Nomad. They discussed discuss what culture, communication, and engagement look like in a successful remote work environment. Truth is, employees are actually more productive and happier when working remotely. Listen in as we discuss why remote work isn’t just a fad in the workplace and how companies can build a great remote work experience for their employees.

From the episode

Ali Greene:

What You’ll Learn


[3:00] Embracing Change

[7:46] The untethered life of a digital nomad

[18:07] There is something unique in every place

[21:05] Aligning your values to your chosen community

[26:20] Escaping the cubicle

[29:53] There is always something interesting in your own backyard

Show Transcript


Hello, and welcome to a new episode of The New Nomad podcast. Really happy you could join us today, really happy that Ali Green could join us. A remote works advocate, writing a book Remote Works: A Manager’s Playbook for Designing a Great Remote Work Environment Experience. We have so much to talk about today, Andrew, because her journey that we’re going to get into is very unique. And I think it gives a lot of people hope that if they want to do a similar journey from let’s say, the United States to another location overseas, or just different locations, and we’ve heard so many great things about Spain, etc. I think this is gonna be really interesting conversation today. But once again, it’s hopefully to give people that optimistic feeling that you can do this. You can pack up and go and create a new life for yourself. What’s your thought? You’ve done that yourself, Andrew, you’ve packed up, you’ve moved to different countries. It’s an exhilarating, but a little bit scary experience. 


It is. It’s one of those things where once you start, it’s hard to stop. And the wild thing is I started over 25 years ago, and it’s been nonstop for me, actually, there have been some stops. And slow-mading or having a base in places for a period of time, I think is crucial. And this is gonna be fun because Ali actually wrote the book on remote work. So it’s one of those things to get get your copy here in the next few months. This is gonna be a fun discussion because she’s got so many valid points that I think are overlooked many times. And as companies, employees, us as people are embracing what’s new to mint, while it’s been existed for many others, whether working remotely from Ukraine to serving companies all around the world, they’ve been Ukrainians have been doing this for decades, for the last 20 years. They’ve been working remotely on so many projects, and those in many countries have. So this is gonna be fun to dive in a little bit deeper into remote work, the mentalities that have to shift, the mindsets that need to change.


Well, let’s bring Ali and Ali you know, the thing is, I read the five things about managing a remote team. But one thing that I really came out with is the maybe the last interview, maybe the most important item you mentioned is about embracing change. You’ve seemed to embrace change. So share with your audience, your journey, and where you are today because you seem to have no fear about going to different locations and embracing the remote work lifestyle.


Yes, thanks so much for having me. And just to start off with a bit of a funny story and not to get too much into psychobabble. But change is one of those things that I don’t know if I chose to embrace it. Or if my whole life it decided to make me embrace it. But I just remember from a very early age, being in scenarios where I was constantly being put into new environments growing up, I went to four different middle schools for very random different reasons. I was not part of a military family, which is the first question people asked me, I lived in Florida, I’m from Michigan, kind of a basic story. But I was just constantly being put in these different scenarios. And I learned at that very like ripe age in my middle school years that change can be really fun. It can be interesting, it challenges different parts of your brain. And I really thrived on problem-solving. And as I got older, when I had to be in one place for too long, I got bored and routine became very unmotivating for me, and I was constantly seeking it out. Where is my new challenge? Where am I going to be put in situations where not only am I learning about the surroundings around me, but through those different surroundings and through those hardships and those mistakes and those failures and accidentally buying a bus ticket where the return was before the departure because I’m not used to using a 24-hour clock like they do in a lot of countries, like very silly travel stories. When you know, five years later, you talk about them and you’re like that’s so ridiculous. And at the time, the stress and the emotion and processing that helped me grow as a person. And then looking at that from a business perspective, it helped me thrive because I was able to always keep up with change in business. And for me, those two things together have just made me someone who is always seeking out, change in my surroundings to cause change in myself and to make me a better person.


Well, we’ve talked to many people in this community. And it seems like the spirit of adventure is something that really makes a difference. And it sounds like you’ve been searching for adventure. I mean, in the sense that you’ve been in 40 countries, and I love your story about the clock, Tommy, because I’ve actually done the same thing with a plane ticket where you actually had the dates. You know, in the United States, the dates are different than overseas, and I had made a mistake, and I get to the airport and like, Yeah, you were supposed to fly the other way today, things like that. So is adventure what has gotten you excited about this? And for people, a lot of the remote team workers who want to pick a unique place to be and you seem to have picked a wonderful place in Spain. Is that a big part of it too, the quality of life?


Yes, and no, I never considered myself an adventurous person until I realized that so many people are afraid of putting themselves into these unique scenarios. And I never considered myself an adventurous person until I looked at my roots and where I came from. Nobody in my family likes to travel, which I think is very unique for me being a digital nomad, and being an advocate for this lifestyle. A few years ago, I finally convinced my mom to get her passport and to come visit me in Spain. And then for the second time in her life, this past September, she came back to Spain to visit me and see my lifestyle, living in one place as a remote worker, where before she got to see me passing through Spain as a digital nomad. And so opening her eyes and seeing the awe that she has, for what I’ve been able to do, in a way, like, allows me to give myself that pat on the back and be like, okay, cool, like, maybe you are adventurous. But for me, it’s just been always about questioning the status quo and not feeling like I necessarily belonged in the place that I happen to be born. Your listeners can tell that despite traveling to 40 countries, I have not been able to get rid of my very strong Midwestern American accent. Today, I’m in France, and I went to a little fromagerie. And despite my really hard, you know, trying to order cheese in French, the guy just looked at me and was like, clearly, this woman is a foreigner. 

And for me, it’s just about there’s certain things in your life, you can’t change, you can’t control, you can’t control where you’re born. You can control now, with remote work, if you feel like where you were born, is your home. And if it doesn’t feel like your home, if it’s not inspiring to you, if it doesn’t feel comfortable to you, if it doesn’t feel uplifting to you, then hopefully, I know I’m in a position of privilege being at the forefront of this movement. But hopefully, for others, this will be a choice that you can now have of where do I go, where I can create opportunities for myself to be inspired to feel like I am motivated to feel like I have the things I need to cultivate a better life for myself. Spain happens a little bit by accident for me. I was always looking for a way to spend more time in Europe, pre-pandemic was not the most environmentally friendly digital nomad, so I always optimized my travel, to cultivate deeper relationships and friendships with people I met as a digital nomad community is very important to me. So in 2018 and 2019, I was like in Cape Town, and then Switzerland, and then Portugal and then the US. And then I went to Thailand, and then back to Spain, and then Mexico and then all over the world. And it didn’t make any sense. And I really liked being in Europe the best. I had a lot of European friends. I was starting to really feel at home here. But I couldn’t navigate the Schengen rules and things like that. And I was like, how do I find a way to optimize my travel in Europe, and I found that Spain has really great opportunities for travelers. This was before things like the digital nomad visas became really popular and I love that they are now and so I started my process to create a home base in Spain. Well before the pandemic event due to everything that the whole world has experienced over the past two years. I found myself now mostly based in Spain and France. I actually haven’t been on a plane for two years now where I used to be on a plane every three to four weeks. And in two weeks I will be going back to the US for the first time. And I’m all of the things like excited, scared, nervous, like talking about all the tacos I’m going to eat in Texas every five seconds. It’s a ball of emotion for me.


Right having done that so many times and I know Allen has as well with his travels over the years, it’s one of those things of joy for Okay, I’m going to eat at this place, I’m going to buy this, I’m going to go to target, the big one. I’m going to Trader Joe’s and buying that one thing that you like there, the little things. But and I think people from many countries cherish that when they go back to a country that they’ve left a piece of themselves in. I think of that when I go back to other places that I’ve spent significant time. That’s one of those things is the anticipation, but also the wonder of what’s going to happen. Am I going to see this person no one really wants to hear the stories. No one, you know, it’s a foreign life to so many people. And the re-entry culture shock that you face. Wow. I remember one time I came into, I was coming in from London, I think at a period of time in England. And I went to a supermarket one I’ve never been to before. And I was just walking down the aisle and the syrups caught my eye. So I stopped and counted how many different syrups that are like breakfast syrup. And there were over 50 different pack types of syrup. Mainly the same thing, just with a different name on the front. But it’s one of those things where we couldn’t find syrup for pancakes or waffles at times. And we searched and searched. And in one of the places where we spent a bit of time and then to come and there were 50. How absurd! It just I remember going back to the hotel where we’re staying in Charlotte, North Carolina and saying can you believe that they had 53 or whatever number it was types of syrup. I can only get numbers I blank. I waited, went to Costco and got a big container of maple syrup. And that went in my suitcase. But yeah, so as you reflect on all these different things, that’s one of the things that jumped out at me is yes, they anticipation for the return. But yet I heard so many other things in that. This is so much truth.


Well, it ties into something Andrew and Ali, I’ll ask you about this is when you travel and you live in different locations. It almost helps you appreciate what you have in the different locations you’ve been. So I know you’ve been in Japan, and you’ve been in the Philadelphia area and you’re now in France and Spain, but when you’re different little locations, there’s different pieces with you there. And I’d love to get your perspective as you travel what you’ve kind of picked up which I know you’re sharing back to others about remote work and part of you know what you learn from that experience.


Yeah, so I love this question. So I organized a digital nomad retreat actually in Mexico City a couple of years back and the theme of this retreat was to have these weekly salon-style conversations where we really got to go deep on a specific topic of conversation. For me one of the most interesting parts about whether it’s working remotely because then you’re working with a multinational team or whether you’re traveling as a digital nomad because then you’re essentially your family becomes a multinational family is getting all these different diverse perspectives and we had a conversation on I’m gonna misremember the catchy title we called the salon, but it was essentially about globalization. And they’re sort of becoming a mono-tone type of culture. Where if you go into Airbnbs around the world as a digital nomad, the sofa is the same sofa whether you’re in Japan or Philadelphia, or Florianopolis, or Mexico City, because it’s all from IKEA. And you can if you’re in a certain size city that has a certain international vibe, you can generally always expect to have a cafe that serves avocado toast. And what I realized from this conversation was that there were certain things I really liked about this and there were certain things that I really disliked about this. And so I and how my brain works generally with everything is I can always see the pros and cons of situations which sometimes makes having debates with me, very challenging for other people because I like to investigate both sides. 

But on the positive side is a digital nomad. What all of this stuff means is that the world is becoming easier for you to leave your home base to travel to immediately go to a new place. And I see it as a bell curve where you go to a new place, you see immediate differences. Oh, they’re, you know, looking left before they look right to cross the street because the cars are driving on different sides of the road are oh, they’re speaking a different language, there’s this initial culture shock. But then you get this piece of familiarity. Oh, there’s avocado toast everywhere. And this allows you to ground yourself to focus on your work to get your day-to-day habits done. And it takes a long time before you then realize and appreciate which is the point, Allen, I think you’re making is really about when you start to notice these differences and appreciate where you came from what you have and what you’re going to have in the future. It takes a long time to really understand that about where you’re spending time as a digital nomad as a remote worker to see like, Okay, this is what this place does differently. These are the cultural frustrations for me in Spain, it’s how long it took me to get my physical ID card because there wasn’t a great way to automate that system. And then on the flip side of that, because things are so accessible, you start to compare and think truly, what does it mean for the world like that I can have avocado toast at any time in any country in any season like that’s not natural. And what would happen in the world, if we go back to these micro-cultures and things are not available to us at all times? What would that mean in terms of scarcity and appreciation and passing down stories to each other? And this awe and wonder and questioning that makes people really listen to each other because they’ve never experienced it for themselves. And I think that’s really cool in cross-cultural teams, where you’re getting to hear these stories about how things are in other places that you’ve never experienced before because it’s so foreign to you. 


And now that I’ve traveled so much, I’m over that hump where I really tried to live, according to those micro-cultures, I don’t particularly like and this might sound snobby to some people, and hey, whatever. I don’t particularly like to eat bread or yogurt in places like Spain, or the United States, because they just do it so darn good in France, like the bread in France is out of this world. And like if I like the butter, like if I have to wait knowing that I come to France quite often to indulge in those things. And then when I’m in Spain, it’s all about the seafood, the tapas, the paella. When I’m in the US, you know, like, Yeah, I’m going to a baseball game, I’m gonna get a hot dog. That, that wanting, that excitement, I think it creates something in myself, where I’ve become really open-minded to what is unique about every place that I’m visiting, and what value it offers me in my life. and translating that to teamwork. Because I think like how I live my personal life is very much translatable to how I look at my team and how I think about work. What is the unique value of why each team member is from where they are? What do they know about their local market? What do they know about how things work, where they’re working? And what can I learn about them, instead of assuming I can just research it secondhand on the internet? So I had a co-worker that lived in Japan, who was telling us how people use the internet in Japan and how different it was than how they use the internet in the United States. And you would assume people use the internet the same everywhere. But that’s not actually true. If you put your ego aside and just listen and ask questions, and I think that is one of the most rewarding parts about remote work is getting to have deep relationships with people that will tell you when you’re wrong and tell you hey, actually, what you’re reading online is not true. This is how me and my friends do it. That was very long-winded. But that is like, what I believe.


No, it’s wonderful. And it’s always great to divert into some food-related good moments too. So you when you’ve moved, you’ve built community and I was it was really interesting reading and learning more about you that how you you met your co-writer, your partner, etc. Share with some of the folks how you build community because I know a lot of folks when they go overseas, they’re like, how am I going to fit in? How am I going to meet anybody? And you seem to have done that very well. And you share that with others.


Yes. So I’ve had many different variations of living a digital nomad life on in terms of work. I used to be the sitting on a leadership team for a startup, I was a freelancer and now I’m an author. So my work has looked very different. As I’ve traveled around, I’ve also traveled very differently. When I first started nomading, and I was craving a lot of alone time, I really wanted to figure out who Ali was. And so I purposely traveled to places to spend time by myself. For many people that can be sustainable, that wasn’t sustainable for me, I got lonely. I, after doing that, for some time, realized like, Okay, that was fun. I got what I needed. What else exists? And I started realizing there were all of these travel programs that existed for digital nomads, specifically. Things like hacker paradise, remote year, Wi-Fi tribe, I tested out a few that are no longer in business and realized that they’re all very different. And so what’s important is to figure out how to align your values and what you’re looking for to the values of the communities that you’re seeking. I ended up doing a hacker paradise trip in Cape Town. That’s where I met my co-author, Tamra, we both were working for two different remote-first companies. And we both had co-workers that were married to each other, which just goes to show before the pandemic, how close-knit the remote work community was. And they were like, You guys need to meet each other and have coffee because you’re both going to be in Cape Town. And that’s how small this world is becoming. And we date and we became friends. And over the years, our friendship turned into our business relationship. And outside of writing the book together, we organize these community retreats in Serbia and Mexico because we were finding that it’s great that businesses like hacker paradise exist. I still love hacker paradise. I’m a huge advocate of what they’re doing. But also, what about just getting together friends and friends of friends, and not having it be a business model? What does that look like after you’ve been doing this for long enough, where you purposefully get a group of 10 to 12 people together, rallied around a theme, so that your have a reason to meet up with each other. Because otherwise, you’re like chasing people around the world and hoping that you can act in the same place and it can get really chaotic. So actually, this past fall in Javier in Spain, where I spend a lot of time, we had eight different people from eight different countries purposely come together, we rented three different apartments. And we like did our own kind of mini co-working digital nomad, super informal, few months together. And it was really special and great, because we all had some connection to each other, even if we didn’t all know each other. 

So that’s one bucket. The other bucket that I love, and it’s a very complicated, interesting market that exists is the co-living market. And I’m you guys have talked to a few experts in co-living. So their insight is a lot more elaborate than what I will offer, with the exception of I have been to probably like a dozen different co-living places. And I have enjoyed my stay at a very small percentage of them. Which is to say, every time I go, I learned something new about myself. And what’s very special and unique about the co-living market is you need to figure out what you’re looking for. And so when I was a full time, salaried employee staying at co-living places, I was looking for social connection more than anything else. I had a job I had a set amount of hours that I was working, I wasn’t trying to build a business. I relied on my team and my company to give me professional development. So if it existed in the co-living place, that was great. But there wasn’t necessarily a strong desire for me to have that. But I was really lacking people to grab coffee with people to go hiking with on the weekends. And so I sought out co living places that especially wanted that. That’s where I ended up meeting my partner in my life now, which is really cool and special. Now, when I was starting my business as an entrepreneur, I realized there were co-living places I went when I was a full-time salaried worker, where people were like, always working and they really wanted to like talk to each other about how they were setting up their business, what they were doing for strategy, and those types of co-living places would have been amazing for me. You know, a year ago, two years ago when I was starting my own venture because those are the types of people that could help me learn and grow as a business owner, rather than an employee. So the advice I would have for people, again, is to self awareness like what are you looking for? Ask questions of the co-living place like who are the people that commonly stay here? Who are what are their profiles? How do you set up your community events to make sure that you’re getting what you need, and make sure it’s a good fit for you. And if it’s not, create your own, it doesn’t have to be a business, it can just be fun. That’s what I did last summer, here in France, because I wanted to, there wasn’t a lot of things that really wanted kids and families around. And I love that. So


You know, it’s one of those things where when I hear you, I think they’re probably people listening, thinking, I want to get out of this cubicle. I want to do what she’s doing. She’s gotten she escaped the cubicle. And what are some of those tips you’d give somebody? If they’ve been commuting into the office for 20 years and they’re, they’ve been given the freedom or they haven’t yet, but they’re going to free themselves and go do it? What are the, you know, top two or three things you did buys?


Yeah, I love that question. I think the past couple years proved that people don’t give themselves enough credit. Especially with all the advancements in technology, I hate focusing on tools when it comes to remote work, I think it’s more about human behavior than anything else. But if you’re trying to convince your boss or your employer, that you can still stay connected and get your job done, and not have to report to an office, the number one data point, and story that you can tell is the past two years as an example, if you’re now returning to the office, just to sit on your computer and write emails to someone or log into a project management tool, or to have meetings with people that are video conferences, not necessarily people that are in your one office, because you have satellite offices and things like that. You were remote working just from the confines of your office. When I first started working my first ever job, I was remote working from the confines of my office, because we had an external sales team I worked with on a daily basis that all lived in the town where they were doing external sales. I was sitting in the headquarters of the company. We didn’t talk about things like remote work back then, because the terminology didn’t exist. But my job was to talk to salespeople. And so I was on the phone every day. That was remote work. I just had to report to an office. And so if that describes your situation in any way, like you can do it. So the next question is, how do you do it successfully? And the second piece of advice that I would give there is you need to learn yourself, you need to cultivate a deep level of self-awareness of what do you need to manage your energy levels, to really help yourself, honor your energy to get your work done. And make sure that you’re setting expectations appropriately and living up to those expectations, and communicating things that we use to let be implicit in the workplace and make them explicit, even if it feels uncomfortable. And if you know how to do that within yourself, then you can start asking the people you work with for the things you need them, they’ll learn how to do it, and it’s sort of this domino effect that can help positively infiltrate the organization to embrace remote work.


Wise words, wow. Okay, so the folks who are with us every week, you know, and subscribed they look forward to this one question as we get toward the end of this, this fabulous interview with you, Ali. I would love to hear about a couple of years ago during the six months into the pandemic you were in Serbia even. So this is one of those things where if you look back over this period of time, what’s one of the most overlooked, and this is broad, places, experiences, books even that you feel like it our listeners would like would mean to experience or know about?


Honestly, I would say the countryside of their own country is probably the most overlooked place, people are always trying to go to these very exotic, far-flung locations, I have been more or less not necessarily forced, but kind of organizing myself around spending most of my time in Spain and France. And they’re not necessarily places that I would always have been excited to say I want to spend 100% of my time in those two countries. And if I were, they would be the really exciting places that come top of mind to people, you know, like Valencia, or the south of France, which I’ve actually never been to. And what I’ve learned is going off the beaten path in those two countries, I went to, you know, the Chateau co-living in Normandy, and who would have thought Normandy would have been an exciting place to go has been incredibly rewarding. Or Delicia in Spain, where supposedly it rains all the time and ended up having beautiful weather in the best seafood of my life. I’m going off the beaten path and places that you spend a lot of time in our places where people can find a new sense of appreciation.


Great, that’s a great answer. So for the folks that want to learn more, where can they find you beyond LinkedIn in other locations, and I know your book is coming out. And we will also share in the show notes.


Awesome. So shownotes will be a great place, our book will be released, we still have some time until it is officially published. So it’ll be out in January of 2023. If you’re in the United States, it will be published through Barrett Polar. abroad. It’ll also be released through Penguin Random House. So keep your eyes peeled for announcements there. We do send out a monthly newsletter with sort of these kind of broad reflection questions that people have heard me talk about, as well as tactical remote tips every month. And so if you’re interested in what I’ve had to say, and you want to learn more, that’s the best place to follow my train of thought around remote work and see the evolution of a book journey, which is something new for me as well. And so if you pop over to our website,, you can sign up for that newsletter. And I have started to embrace more of my vulnerability and sharing on LinkedIn. And I’ve been having tons of fun with that. I’m sharing pictures of me snuggled up working from a sofa and drinking coffee. And so if you want to see a little bit more of the real Ali behind the scenes, definitely connect with me on LinkedIn.


Thank you so much. Well, great conversation today. We really appreciate you joining us on The New Nomad. To our audience out there. Please continue to travel safely. Look up Ali and learn more. We want you to travel more and very excited to share some of those tips today. Look forward to catching you again in the next episode. Cheers

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About the Guest

Ali Greene is a full-time digital nomad, logistics guru, consultant, and remote work expert. She has ten years of startup experience and four years of leading remote teams while traveling the world full-time. From rolling out benefits plans while slurping ramen in Tokyo, to planning a company restructures from the beaches of Spain, Ali brings her real-life experience to Remote Business Strategies and People Operations. Ali is the founder of whose mission is to educate, inspire and engage teams to create efficient, effective, and innovative frameworks for the future of work, regardless of where (or what) their “office” looks like. Previously, Ali was the Director of People Operations for DuckDuckGo, the internet privacy company. The DuckDuckGo team is fully distributed with more than 75 employees in over 16 countries.

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