INTRO: This is part two of my interview with Ebonie Finley. If you have not yet to part one, I highly recommend you go back and do that first because it provides some really important context for this episode. If you have already listened to part one, then please enjoy the conclusion of my interview with Ebonie Finley.

Matt Bowles: Ebonie, I also want to talk a little bit about some of your other travel experiences that you have had. I think the place that I actually want to start is just in terms of your connection with the Bahamas as an adult and what that has meant to you. Talked a little bit about going back with your family as a kid and what the dynamic was like when you were younger. Now, as an adult, what is your connection like with the Bahamas and what is it like when you go there?

Ebonie Finley: This is a weird connection. So, it feels like home, but I always go as a tourist. Weirdly, I never go as like, oh, I’m going home. I still know that I’m not fully Bahamian, that I’m not fully integrated in the culture per se.

However, it will always hold a really special place in my heart. Like, for example, I celebrated my 30th birthday on the sailboat of the Episode 5 in the Bahamas of Nomad Generation in the middle of the sea in the Bahamas. And it was like a full circle moment for me.

You know, I was with Quebecer friends on the boat in the middle of a Bahamian ocean. We’re on a 33ft tiny sailboat surrounded by, and I kid you not, millionaires, yachts. And they have invited us to their Christmas because I’m born December 24th, so it was also Christmas. They had invited us to their party on a dock and we’re in the middle of nowhere and they have butlers and caviars and it’s just.

And I’m just like, wow, this is part of me. But I’m also experiencing this as a traveler. And that’s how it always feels for me. It’s always that push pull of it feels like home, it feels safe, it feels native, it feels like it’s part of me. But I also get the amazing opportunity to experience it as a tourist.

For me, Montreal is not touristy anymore. Right. Because I live here. So, I don’t get that pure excitement that you were talking about when you first came here. And you’re like, my mind was blown. Right. But for me, Bahamas is that like it’s the only place in the world where I’m a tourist, but it’s home. Like, I have my tourist eyes, but I feel safe, and I know where I’m going, and I have family there and there and I know that I’m sleeping.

So, it’s a very unique dynamic for me and I want to keep it that way. Honestly, it makes me happy to have that place in the world.

Matt Bowles: What would you recommend for people that have never been to the Bahamas? They wanted to come for the first time and really experience it. What would you put people onto?

Ebonie Finley: I would recommend going more to the family islands or doing a boat ride that will take you to the more secluded islands like Bimini, Cat Island, Andros, the really cool one to visit. If you go to Nassau and if you go to Freeport, you’re going to get your classic hotel feels and the very Americanized version of the Bahamas.

But if you go to the other islands, there are 700 islands. You will very likely find uninhabited islands where you can spend the whole entire day there and chill. You can visit Inagua Island; Pig Island is really popular as well. So, the family islands, I think are the most culturally rich and those are the ones I think that will really plunge you into the Bahamian culture.

 

Matt Bowles: Well, I also want to ask you about one of your other favorite places in the world, Costa Rica. I know you’ve been a dozen times, and I would love to ask you to share a little bit about why you love Costa Rica so much and what you would put people on to. Because Costa Rica also in some places is also an over touristed destination and I know you have experienced a lot of Costa Rica.

So, what do you love about it and what would you recommend for people that would like to experience Costa Rica?

Ebonie Finley: What I love about it is the Pura Vida. I think I’m wearing my watch, right? And when I was in Costa Rica, I could literally see my heart rate had dropped. In Quebec, I’m always on like 75, which is like really high. And in Costa Rica, I was like on 64, 65. So right there, Pura Vida hits me hard.

So that’s a pole to Costa Rica. I love yoga. I love surfing. This is the place to go if you’re looking for a yogi little kind of surf town. Santa Teresa has always been that for me, and I’ve just been recently. I just came back actually from Costa Rica, so I can’t say that it’s still like that. Unfortunately, Santa Teresa is now becoming a Tulum. Like, it’s changed a lot. It’s very Americanized.

Like, it still kept the local heritage and everything, but it’s not what it used to be. Like, it used to be a dirt road, inaccessible, really hard to reach. But that’s what I loved, right, because you would go there, you could eat like a four-dollar casado, which is the typical meal. It’s just fish, white rice, beans and banana, and plantains. But I would kill for casado. I don’t know, I’m just in love with it. I’m obsessed with it. It was like $4. You could have that anywhere at a local little shop and it is served for $5 a day. Not anymore, unfortunately.

What I will recommend if someone is visiting Costa Rica for the first time is to stick to the west coast near Liberia and San Jose. So Tamarindo, they call it Tamagringo, actually. But it’s a cool destination. Not going to lie to me, I don’t even care that they call me a gringo. I’m like, yeah, I’m a gringo. I don’t care. If you want to party, that’s where you’re going to go. It’s very convenient. It’s an hour away from the airport. You can still surf. It’s just convenient and nice and easy. So Tamarindo is awesome.

Then if you want more of like the jungle experience, head to Nosara.

We just visited Samara. It’s still kind of untouched. So, I’m saying this exclusively for whoever’s listening to this podcast, that Samara is still very untouched. Highly recommend. There is no nightlife, though. There is no nothing. It’s the Pura Vida. Your heart rate will go down because there’s nothing to do. But I love that. I just want to surf and yoga and eat some fresh mangoes. I personally, I love that stuff. And wash the sloths and the wildlife.

And then, yeah, Santa Teresa is a mix between the Costa Rican culture, the nightlife, the fact that it’s more convenient and touristic now, but it’s still trying to keep its charm still. Highly recommend.

Unfortunately, I had really bad experiences on the East Coast. I went there for the first time during this trip. And the center, you have to know that it’s microclimates, like if you’re going to Monteverde and La Fortuna, amazing for the volcanoes, but it’s a microclimate. It rains a lot.

Nevertheless, Costa Rica has my heart because it’s fresh food, it’s beautiful, local people, it’s safety. I feel really safe as a woman and as a woman of color. It’s surfing, its yoga, and it’s just, yeah, Pura Vida. You have to go experience it.

Matt Bowles: Well, speaking of feeling safe as a woman of color, I was watching some of your TikTok’s and I want to put people onto your TikTok channel because it is fantastic. You have a really wide range of nomad content from all around the world and your reflections and tips on all sorts of stuff. So, we’re going to link that up in the show notes as well.

But one of the things I was watching on your TikTok channel was you went to Medellin, Colombia, and you were interviewing other BIPOC women that were in Medellin, and you were asking them about why they chose Colombia. And that got into what I thought were some really important conversations about safety considerations, as well as other things for women of color, nomads.

But can you share a little bit about your experience in Colombia in particular and then your reflections on some of those conversations?

Ebonie Finley: Yeah. Medellin was one of these places that I had no expectation. I knew that it was a nomadic hub, but I was really wondering why it was such a hub. Now it’s very clear. There’s a really big nomad expat community over there. So, making friends is really easy. There’s a huge black community over there.

And the reason why, this is my opinion, it’s not a fact, but I think that women of color are celebrated and are actually the beauty standard in Medellin. All the graffiti are black women with, like, big curly afros, like, the t-shirt. They’re not selling Colombian women, Weirdly, it was black women that were being portrayed, and that was, like, the beauty standard, the paintings.

So, I think black women over there are celebrated, and that feels different, and it feels good, and it’s a really good pull. And because there’s a lot of other Black women, they kind of created this community where you’ll easily have access to someone to do your hair, someone that sells product for your hair, someone that knows where you can find good creole food or good this or that.

So, it just really created this kind of organic black community, and it attracts more and more and more black women. So, it’s just on a roll. I can say I felt really safe, I felt beautiful. I did make a TikTok about that saying it’s not that you’re not pretty, it’s just that you’re in the wrong location.

So, this whole concept of like beauty standards really changes depending on where you are in the world. And I can say that Colombia is a place where I felt beautiful, I felt celebrated, I felt safe, and I felt heard and seen. It was really great. It was really, really great for that.

And then it’s obvious why it’s a hub. Like the cost of living is really low. The nightlife is absolutely amazing. Internet is available everywhere. It’s the best Internet I’ve ever had in my life. Foodiest town. It’s all around like really cool place to be a nomad.

Matt Bowles: How has your experience been as a BIPOC digital nomad now that you have been traveling around the world since. Well, you’ve been traveling around the world longer than you’ve been a digital nomad, but especially since you’ve become a digital nomad and started traveling so consistently and on such a long-term basis in terms of things like navigating anti blackness, whether that’s in the local place where you are or even within in digital nomad communities.

And some of those types of dynamics, especially for maybe BIPOC listeners to this podcast who might be at the earlier stage or even the aspirational stage of moving into this lifestyle, would love to hear just any of your reflections on your experiences and then tips that you may have for folks.

Ebonie Finley: Yeah, so I do a lot of research before going and then I always have an exit plan. First of all, if the research is telling me that it’s not safe for me to go there, I’m probably going to avoid it. But if it’s per se a place I really want to go, I’m like unsure and let me try this out for myself. I will research nearby destinations that are safe and I’m giving myself the flexibility that if it doesn’t feel comfortable, I can bounce at any moment.

I know my plane ticket is going to be like two, three hundred dollars and I’m going to leave. So, I’m not going to book five-week accommodation and stay there for a really long time. I’m just going to test it out and if it’s not good, I’m leaving.

Luckily, the destinations that I have chosen, I have never had any issue actually being black, have worked to my advantage. I got to be really honest with you, most destinations, I look like a local. Like, if I go in Latin America, I look Latina. If I go to Africa, I look African. If I go to Europe, I can be from anywhere. If I go to Asia, even Cambodia, Philippines, places like that, and I straighten my hair, I can almost sometimes kind of pass. So, it has worked to my advantage.

Matt Bowles: Ebonie, the other thing that I have got to talk to you about is finding love and partnership in the digital nomad lifestyle. And I think I want to start by asking you to tell the story of your first date with your relationship partner. Can you take us back because this is an amazing digital nomad story. I mean, give whatever context you want in terms of how you met and so forth. But I would love for you to tell the story of your first date because I think it is really an epic digital nomad story.

Ebonie Finley: Yes. I’m going to throw a bottle in the water if anyone from Netflix is listening to this. I think this should be a Netflix movie, okay? Because it is dope, honestly, not just because it’s my story. I think this is straight out of a movie. So let me take you back.

We are specifically March 2020. The pandemic has started. The whole world is crashing. Everyone’s like, it’s the end. Write your will. We might not survive this. Okay? This is the context I’m back from, I’m back in Canada. I just broke up a couple of months ago with my ex, living in Whistler, traveled to Bali and all of that. I’m back in Canada now. I am in my little apartment in Montreal thinking, this is how I’m going to go.

So, I’m scrolling on Tinder and all of a sudden, I see this feature, Tinder passport, and it’s telling me that it’s free. And I started looking it up on the Internet, like, why is this free? And Tinder announces that this is going to be free during the pandemic to help people who are going through extreme solitude at that time. I don’t know how it was for you guys in the States, but here in Montreal, you needed a coupon to go to the grocery store. It was really intense. You were stuck in your house.

So, I’m going to take advantage of this. Are you kidding me? The minute the borders reopen, I’m going to start traveling again. So, I’m swiping. I said earlier I like snowboarders. I also like surfers, and I’m swiping sexy surfers in Australia. I’m swiping Bali. I’m swiping Greek gods in Greece, and I’m like, let me get some Italian food also, and Hawaii. I am all over the world loving this. Like, this is my dream. Are you kidding me Tinder passports? Chef’s kiss. Best teacher out there.

My boyfriend, who was not my boyfriend at the time, is also a traveler. He’s also smart. He has his visa to come to Canada, but the borders are shut down because it’s Covid. And he’s like, let me shop in Canada before I get there.

So, I guess he started swiping in Canada. We think that we swiped in Whistler. He’s from the UK, so remember, he’s in the UK, I’m in Montreal. But I did set my location at a certain point in Whistler because I like snowboarders to check out the guys there. And I think he was also swiping in Whistler because he wanted to move on the west coast of Canada, and we matched there. And honestly, the guy had literally no picture of his face.

So, this is how disengaged I am with him. I do not care. Like, his profile is a surf emoji, a snowboard emoji, and a world emoji. And he’s like, I like to travel. I’m like, that’s good enough for me. You snowboard and you travel. Oh, yeah. And he’s tall. There’s also a picture of him and his friend from afar. And he’s like, I’m the tall one. I’m like, I don’t need to know anything more. Check. Let’s go. And who cares?

I’m talking to, like, 100 guys on Tinder at the same time. Like, thought nothing of it. But my little British boy, he was persistent. Every morning he’s like, good morning. Every night, good night. How was your day? Striking conversations with me. I start opening up. I’m bored. There’s nothing to do. Anyways, he’s asking me a lot of questions about Quebec and Canada and telling me how he wants to move here for two years. And I’m asking him, how’s Covid in the UK? And next thing you know, three months later, we’re talking every single day, we’re Face Timing.

Like, this guy has become a part of my daily routine almost. I’m still talking to other guys. I literally have a date with someone in Montreal, a real person that I can touch. And so, I got dolled up. I’m ready to go on my date. I’m in my car, I’m about to drive, and I realized, crap, I actually don’t want to go on this date. I’d rather stay in my apartment and chat to my British guy than go and have food and drinks with this other guy.

So, I canceled the date. I called my British man, and I’m like, listen, I just canceled a real date to stay here and talk to you and drink my kombucha in my apartment, talk to you. And he’s like, oh, my God. I have stopped talking to other girls too. I didn’t want to bring it up because I didn’t want to look desperate or clingy.

And I was like, I think it’s time for us to start asking questions about where this is going. He’s like, I absolutely agree. Well, let’s meet up. And from that moment on, we decided that we would try to meet up, but it’s still Covid. All borders are closed. And for the next two months, three months, we worked every single day finding destinations that were open and where we could meet.

And there was a window. After three months, we found a window in Greece. So, we were jumping on this window 48 hours later, plane ticket was booked, and I was on my way to Greece. My mom, for sure, thought I was going to die, like, get kidnapped. His parents thought he was getting catfished. Everyone thought we were crazy, but we didn’t care. We really wanted to go on with this.

My plane ticket was quite expensive. His was, like, 50 quid. So, I was like, perfect. You’re saying you’re a digital nomad? You’re saying you’re a traveler? I want to make sure this is true, because I’ve left every single ex in my life because of traveling. So, you are going to prove to me that you are actually a really good traveler, and that traveling is an integral part of your lifestyle, because it is of mine. And we will not ever work if we can’t travel well together.

I gave full responsibility to this dude. I was like, I am not checking a single hotel. I’m not looking at any activities. I’m not doing anything. You are in charge of everything. And he completely blew my mind. I fell in love with him before even meeting him. He is 10 out of 10. If any guy is listening to this, take notes, okay, because you’ve heard earlier that I was on the Amazing Race Canada. He organized a virtual scavenger hunt in Athens for me virtually, because I landed there 10 hours before him to keep me entertained. That was amazing.

Like, I don’t know how he did it, but he figured out a way that he would give me clues to the next place. And my Uber driver was all in on this. And it was so entertaining, so fun. And I visited Athens like that before he arrived. Then when I arrived at the hotel room, it’s a movie scene. I opened the door and the receptionist is like, Ebonie, hello. And I’m like, what is going on? And she’s just, oh, Jamie told me everything. I know everything. We’ve been talking. I know the whole story. I chose your room. Petals, rose petals on the bed. Like, she knew everything.

He had been talking to this girl, organizing everything. I had a handwritten note by her told by him waiting for me on the bed with rose petals and a bottle of wine. And it was absolutely amazing. And she’s just like, whenever you’re ready, supper is paid for you on the rooftop. You get a sunset view of the Acropolis waiting for your date.

Are you kidding me? I called all my girlfriends. I was like, I am marrying this guy. This guy is mine. Girls, he’s off the market. This guy is mine. And he orchestrated that trip like a freaking pro. It was the perfect amount of travel time and downtime. We got to see everything. Every single hotel was pristine. Well chosen, perfect location, a true gentleman. Wow. Fell in love. It was amazing. And now we’ve been together for four years.

Matt Bowles: See, this is why I wanted you to tell the nomad love story. I mean, this is the love story that so many people are looking for.

So, following that first date, can you share a little bit? Now, looking back on four years of an itinerant nomadic relationship of world travel, what are some of your reflections and maybe tips on maintaining a long-term nomadic relationship in a way that is joyful and fulfilling and all of those things.

Ebonie Finley: Honestly, independence is key. Dating a nomad is, I think, difficult in the sense that I have travel plans, he has travel plans. I have dreams, he has dreams. It’s impossible to think that our worlds are always perfectly going to collide and always perfectly going to align together.

So, we’ve just promised that we would give each other that space and that freedom and that independence. Too. Yes, we are traveling the world together, and there’s ups and downs and it’s absolutely amazing. And sometimes it’s an absolute shit show. But we also are giving ourselves the right not to always be together and to not always travel together.

For example, he’s going home for the next month and he’s going to go to Spain and he’s going to go to the UK and I’m not going and that’s totally okay. And I want to do a surfing trip with my girls, and I actually don’t want him to come and like, that’s totally okay as well.

So, I was traveling before him, he was traveling before me. We both acknowledge that we both really respect each other’s independence and being best friends. What I’ve realized on that trip in Greece was that Jamie, he became my best friend before he ever became my lover or my travel partner or my life partner even. I say today where I’ve now sponsored him or talking about getting engaged and like, we’re really far, you know, in our love story now.

But it’s all about being friends because traveling is not always pink and roses and butterflies and it’s all about making decisions sometimes and being in unsafe places sometimes and losing a shit ton of money and like, everything that can go wrong sometimes will go wrong. And it makes it so much easier when you’re with your friend versus, like you’re just with a travel partner.

So, we’re friends first, lovers second. And that balance helps us really maintain, I think, a healthy lifestyle and a healthy amount of travel. We understand that we need downtime, we understand that we can’t always be together 24/7. And yeah, we support each other in that way.

Matt Bowles: So. Awesome. Well, I also want to talk to you about your remote job work, working for Safety Wing. Can you share a little bit with folks who have never heard of Safety Wing, what it is, and then share a little bit of your personal story about how you decided that you wanted to work for Safety Wing.

Ebonie Finley: Yeah, Safety Wing has completely rocked my world. So, it is an insurance company. We also have really big goals. We’re trying to build a first country on the Internet and a global safety net for remote workers, digital nomads and travelers’ expats. We believe in equality for everyone, and those values are really seen throughout the company.

Safety Wing is also the first job where I am fully encouraged to be my authentic self. And I really don’t mean that lightly, honestly, now that I work for Safety Wing, I can say this out loud, but I’ve lied to a lot of employers about being a nomad. I’ve almost never added my coworkers on any of my social media I would always have a blurred background. I would be like, yeah, I’m just remote. But really, I’d be in Mexico or Costa Rica or Nicaragua.

You know, in reality, it doesn’t matter. The job was getting done. But, like, it’s just. They were not all up for being a digital nomad, whereas with Safety Wing, it’s celebrated. It’s so great that it actually helps me as a sponsorship manager. Like, I speak to other nomads on a daily basis, so I can relate to our typical customer. I understand them like I am them. I was using Safety Wing before I ever worked for them. And the company is just amazing. We have these yearly company retreats where we all get to work together.

We have unlimited PTO. Most people work regular hours, and we work hard, but we also have unlimited time when it’s needed to recharge our batteries because we believe in having a life outside of work. And that’s a value that was really important to me. And at Safety Wing, I don’t have to hide that. Everyone believes in that.

The founders believe in that. If you need time off, you take the time off. No one’s counting your days, no one’s counting your hours, as long as the job is done. And we’re all human. And I feel like everyone at Safety Wing could be my friend or is already my friend. And we’re a team of digital nomads working to create the first country on the Internet and a global safety net for us, for everyone.

Matt Bowles: Can you talk about your experience as a Safety Wing customer before you started working for Safety Wing? And again, just for folks where this is their first time hearing about Safety Wing, what is the product that you decided to purchase from Safety Wing, and what was your experience like as a digital nomad?

 

Ebonie Finley: Using Safety Wing as a customer always struggled with insurance. And then I found Nomad Insurance by Safety Wing, which completely blew my mind. So here in Quebec, if you’re looking to travel outside of Canada and you’re looking to purchase insurance, they’re going to make it really complicated for you. They’re going to be like, when are you leaving?

Well, as a nomad, I don’t always know. Sometimes, like Greece, I purchased my ticket 48 hours in advance. So, when are you coming back? That’s a question I cannot answer. I never know when I’m coming back. I have no freaking idea when I am coming back. So that was always an issue. Where are you going? What’s your itinerary? I don’t know. I have my hotel for the first 48 hours and that’s that. Like, I have no idea.

So, most companies will not insure you when you don’t have the answers to these questions. Safety Wing is not ever a problem. You can literally sign up on the plane. You do not have to answer any questions about your itinerary. Unless you’re going to a country that’s at war, you are covered. You have peace of mind that you are going to be covered. It’s a pay as you go subscription model, meaning it’s kind of like Netflix.

I’m traveling, I’m using it, I’m paying, I’m coming home, I unsubscribe, I stop paying, I don’t pay a dollar more, DM, like, that is so convenient. The customer service was amazing before working there. This was one of the main selling points for me because I wanted to talk to a human. Yes, we’re all birds, okay? If you go on our website and you check Safety Wing, we’re all birds.

And that is for, like, the values of freedom and flying free and everything that has to do with freedom and building a global safety nest and like, all of that. But you will talk to a human, which is so important. Like, I want to ask my questions to someone not a robot. And the response time has always been under a minute. They will answer any questions that you will have. As a surfer, as a snowboarder, it was super hard to ensure those are covered in like our basic packages, which to me was another issue.

Every other insurance company is always, oh, but I’m going on a surf trip. Oh, sorry. No, no, no. That’s considered an extreme sport. Are you kidding me? So that’s in our basic package. I love that. And then you have the add-ons, which are also a game changer for me.

As a digital nomad, I travel with my laptop, my camera, so much gear, so many valuables. I can have that insured if I lose it, if it gets stolen or anything like that. So that’s also been such a good peace of mind knowing that if my laptop gets stolen, Safety Wing is going to reimburse me. Like, no questions asked. So, all these reasons I love Safety Wing.

Matt Bowles: Well, I definitely want to encourage people to check it out. So, who is Safety Wing for in terms of we talked in this conversation about the different types of versions of the digital nomad lifestyle. Who is safety wing for? And give us a little sense of what it covers and who should be looking into it specifically.

Ebonie Finley: It is for anyone that is planning to do a trip leaving their home country. However, our core customers are definitely digital nomads, long term travelers and expats.

The nomad insurance policy is geared more towards digital nomads and long-term travelers. And our expats would be looking at our nomad health program, which is really a comprehensive health coverage that will cover regular visits at the doctor, your gynecologist, going to see your physiotherapist, your dentist, all the things that you would normally have at home that would be nomad help. But if you’re looking for travel medical insurance, that’s going to be nomad insurance and anyone can purchase it, but it’s going to be very convenient for digital nomads, expats, travelers.

Matt Bowles: It is an incredibly unique solution to the digital nomad lifestyle. And so, we’re going to link that up, folks in the show notes, or you can just go to themaverickshow.com/safetywing and there you’re going to find the details about the terms and what is covered. And in about 10 seconds you can get a specific price quote for you personally and see exactly what it would cost for you.

And I was very surprised that it was a lot less expensive than I thought that it would be. So, if you just go to themaverickshow.com/safetywing right there, as soon as you land on the page, you’re going to be able to see exactly how much it would be for you in about 10 seconds. And then also just to get more details about exactly what’s covered. So, we’ll link that up in the show notes as well.

Ebonie, I want to ask you now about some of your reflections on your experiences traveling the world over all of these years. Some of your travels, travels, a lot of them have been solo travels. Some of them have been with a partner and so forth. But when you think back in either of those scenarios, what are some tips that you have? And I know you produced a lot of content on this, so I want to sort of draw this out. Some tips specifically on making friends around the world in the nomad lifestyle. For a lot of people, they hear that term like solo travel, and it sounds like maybe it’s lonely. You know, what would that be like? What has been your experience and how do you make friends when you travel the world?

Ebonie Finley: That’s a great question. I understand why it comes up so often because it’s kind of like this visceral fear that like, oh my God, I’m going to travel and I’m going to be all alone and like the solo travel for me, let me tell you, I literally am more by myself and have a harder time making friends when I’m traveling with my partner Jamie than when I’m solo traveling.

I cannot find time for myself when I am solo traveling, I literally almost always end up having or making too many friends. And then I’m like, damn, I bought a book, and I can’t even find five minutes to read it. That’s how intense it is. So, I think as a girl, we really have to step away from that fear. Because if you’re a solo female traveler, every other solo female traveler is going to want to be your friend because they’re also solo female traveler. So that whole entire community of solo female travelers is going to want to talk to you.

I’ve noticed with years when I was first started doing this, I would go to the hostel, I would sit at a bar, order a drink, look who looks like they’re also on a solo traveling journey, and then ask them where they’re from. And then from that, honestly, really hard not to become friends or at least spend the evening together. So, if you start with hostels, it’s going to be really, really hard not to meet other people. So, I would always start there.

Obviously, if you’re going in like this five-star hotel in your room, on your own, it’s going to be harder, but you can still book group tours, things like that. That’s also another way in which I would always make friends, but I would start there. And then Facebook groups are popping. That’s probably the easiest way. For example, Medellin, it was a WhatsApp chat. And literally the first day that I arrived there, I was like, hey, I’m looking to interview people. Like, I’m traveling, anyone wants to meet up. And my schedule got filled up so quickly that I didn’t have time for myself anymore. So, like, it became a problem where I was like, I’m supposed to, I’m supposed to chill, and I don’t have time.

So, the Facebook groups I’ve met girlfriends on, Bumble BFF has been awesome. The WhatsApp groups are awesome. And then, yeah, just hostels tours, you just need one. One person’s going to introduce you to that other person and then it’s a snowball effect. And then it’s really difficult to not make friends after that. And then if you start dating on top of that, if you’re single, then like, you’re in for a treat. Good luck finding time for yourself.

Matt Bowles: So, for people that are listening to this that are not yet into the digital nomad lifestyle, but aspire to be, let’s say, maybe back where you were in that 2016, 2017 period of your life. And they’re hearing this, you, Ebonie, have written a comprehensive guide on how to become a digital nomad. And I’m wondering if you can just share some tips from that in terms of, of what the steps would be. For somebody that hears this conversation, they get inspired by it. What should they start doing as soon as this podcast episode is over?

Ebonie Finley: Money is the first thing, right? So how are you going to sustain yourself whilst you travel? Are you going to be working? Are you going to take a sabbatical year off?

Money is the first thing. If you’re taking some time off, then you want to budget that and you want to make sure that your budget aligns with the destinations that you’re going to. Inside scoop. If you’re going to Costa Rica and you try to do budget travel, best of luck, it’s not going to happen. You know, you probably want to go to Guatemala or Nicaragua instead, but stay away from Costa Rica, because it is not for the Broca backpackers.

Let’s say if you don’t have a remote job, then the first thing I would do is find a remote job. Honestly, there’s this whole conversation about how hard it is. I don’t really sense that, like, I also have a guide. It’s not on my website, but it’s on my TikTok. I also have a guide about, like, I have 60 legit remote work site that have thousands of legit remote jobs. The Facebook groups are great for that as well. So, finding a remote first job that will allow you to work from anywhere is going to allow you to sustain yourself whilst you travel.

And then, honestly, I’m not the biggest planner, so I’m not going to say, like, plan it out. I’m going to do segments like, I know that I’m going to leave for five months, I want to do Latin America. Honestly, all I knew was that I wanted to spend two months in Costa Rica. Everything else was a sheer surprise. I had no idea I was going to go to Guatemala. No idea I was going to go to Panama. No idea whatsoever. And I like to have that flexibility. I like to leave space for the unexpected. But, yeah, I would just find a remote job and then plan ahead. If you have a house, you have to rent it. I own a house. I always figure out a way to rent my home. I book my accommodation for the first week and then I’m gone.

Matt Bowles: And Ebonie, can you share, now that you’ve been in this lifestyle for so long, how do you design your lifestyle today? What are some of the most important pillars for sustaining this lifestyle over the long term in a way that continues to be exciting and joyful?

Ebonie Finley: Honestly, buying a house for me has been that balance. I think that a lot of people glamorize traveling full time and the digital nomad lifestyle. For me at least, the truth is that it’s exhausting. You’re always planning the next place you’re going to go to. You’re always making sure the Internet is reliable. What am I going to do with my weekend? I mean, this personal. I can speak for myself, but if I’m in Guatemala for only a month and I’m working on top of that, that means I only have maybe eight to ten days to myself, right where I’m not working, that I can really explore.

I want to make the most out of them. Like, I don’t want to miss anything. Chances are I might not come back to Guatemala because the world is a huge place, and I want to see all of it. So, I really spend a lot of time, once I’m at a destination, planning what I’m going to do with my weekends and making sure that I don’t miss anything. And that’s really tiring. That’s really exhausting when you’re trying to do city to city in a destination. The travel time, everything, like getting the wrong Airbnb, a wrong hotel, getting sick, all that stuff that happens.

So, what me and my partner have found is that traveling six to eight months out of the year is what works best for us. Having a base is really important. Having a place where we can recharge our batteries, where we can have our stuff, like not having my stuff scattered at my mom and my best friend’s house and some of my brothers. And having a place where it’s like, this is actually all of my stuff. It’s smells like me. That was really important, like my bed.

And giving ourselves times where we’re actually not actively seeking to travel, where we’re just actually focused on doing nothing. Honestly, we’re just home. Like, yes, we’re enjoying Montreal, but it’s not hard work. I know Montreal. I am from here. It doesn’t require me to organize anything to go spend a weekend in Montreal. I just go and I do what I do. So, it’s different for everyone. I understand there’s people that always want to be on the go. I understand there’s people that love to come and go. But because I own a house and I need to rent my house, it’s so much work to like, find a good renter, turn the house upside down. Like we’re putting away all our personal belongings and this and that. It’s just worth it for us to leave for a long period of time, take it all in, burn ourselves out, and then we come home, we crash, we recharge, and then we do it all over again. That’s seen our formula.

Matt Bowles: When you think back about all of the travels that you’ve done over your life now, all the different places you’ve been and the people you’ve met in these experiences, many of which you’ve documented, some of which you haven’t, how has all of that travel impacted you as a person?

Ebonie Finley: I think traveling is the school of life. It has also led me to think independently more for myself and accept that I am different and there’s nothing wrong with that.

Personally, my family still doesn’t quite understand my lifestyle. There are a lot of people around me that still ask me, when are you going to find a real job? I have an awesome job. Or like, when are you going to settle down? And no, this is my lifestyle forever. So, it’s really led me to not care so much about other people’s opinion. Think for myself. This is my life, I’m living it. So, I get to choose what I want to do with it and really not care about society’s judgment. And yeah, just be more critical and independent in what I stand for, what I believe in, why I believe in those things, and that it’s okay if it’s different from the masses.

I also acknowledge how privileged I am as a traveler. Honestly, it always puts things back in perspective. In Guatemala, we were living in a beautiful apartment next to people who were literally living in trash. I am going to do a YouTube video about it. It’s not out yet or anything, but they were living in. It was trash that was like build into a home. So, it just puts things in perspective. How small sometimes our problems are and our First World problems and how privileged and lucky we are to be able to experience this and do this.

I really try to travel more responsibly and always try to encourage locals and be aware that I am part of the gentrification problem. I don’t have any specific solutions other than encouraging locals, but I’m still aware of it and I’m really trying to learn more about that. And yeah, I think it just made me a more open minded, grateful, happy and free person.

Matt Bowles: There’s a lot of people that get into the nomad lifestyle. They do it for a couple years, they have a bunch of rich growth experiences and learn about the world, and then they end up back in a much more traditional sedentary lifestyle and get back on that track. For you at this point in your life, why are you still so passionate about traveling the world? What does travel mean to you today?

Ebonie Finley: It makes me feel alive, honestly. That’s when I feel the closest to my core and my essence. That’s when I feel free, and I am living my absolute best life. When I’m traveling, I feel like I’m thriving. I feel like I’m not just surviving or merely surviving. Doing the grocery and the dishes and like cleaning and the pots and oh my God, this weekend I’m receiving my mom and like I’m thriving.

I just climbed Acatenango during the weekend and then I’m on my Monday meeting and I’m like, do you guys know that I just climbed 4600 meters of a volcano this weekend?

I feel so alive. I feel so badass. It just makes me feel like the world is my playground and I’m on top of it. I am living it to the fullest and I never want to get rid of that feeling. As long as my body will allow it, I will keep doing this.

Matt Bowles: Ebonie, I think that is the perfect place to end the main portion of this interview. And at this point, are you ready to move in to the Lightning Round?

Ebonie Finley: Woohoo. I’m ready. Bring it.

Matt Bowles: Let’s do it. All right. What is one book that you would recommend that people should read?

Ebonie Finley: You are a Badass from Jen Sincero. Completely changed my life. You have to read it. However, I’ve just read The Mountain Is You, but that one is also really good. So, can I have two books?

Matt Bowles: You can have two books. We’ll put them both in the show notes.

Ebonie Finley: Perfect.

Matt Bowles: All right, Ebonie, what is one travel hack that you use that you can recommend to people?

Ebonie Finley: I purchased all of my plane tickets on Air Canada because the 24-hour refund is really easy. And when they ask for an exit ticket, I just use Air Canada. And I always get refunded 24 hours after because I don’t have a return date.

Matt Bowles: All right, Ebonie, who is one person currently alive today that you’ve never met that you’d most love to have dinner with? Just you and that person for an evening of dinner and conversation?

Ebonie Finley: Oprah Winfrey. I Think she’s absolutely amazing. Inspiring. Oh, my God. I want to interview her. Yes, Oprah, all the way, my girl.

Matt Bowles: All right. Knowing everything that you know now, if you could go back in time and give one piece of advice to your 18-year-old self, what would you say to 18-year-old Ebonie?

Ebonie Finley: Plan for your retirement, save money and life is not that serious. Loosen up.

Matt Bowles: All right, of all the places that you have now traveled, what are three of your favorite destinations you would most recommend? Other people should definitely check out.

Ebonie Finley: Cape Town, South Africa. I’m still going to go with Santa Teresa in Costa Rica and Maui in Hawaii.

Matt Bowles: Ebonie, what are your top three bucket list destinations? These are places you have not yet been highest on your list you’d most love to see.

Ebonie Finley: Japan cannot wait, New Zealand and Philippines.

Matt Bowles: Amazing. All right, Ebonie, I want you to let folks know at this point how they can find you, follow you on social media, watch your amazing content. How would you like people to come into your world?

Ebonie Finley: So TikTok is my favorite platform right now. I’m abusing it. I love it. So, they can find me @ebfinleytravels. I am going to launch my YouTube channel soon. It’s the Nomad Generation. That is also my website. Then nomadgeneration.com.

Matt Bowles: All right, we are going to link all of that up in one place in the show notes. Just go to themaverickshow.com go to the show Notes for this episode. There you’re going to find links of all the ways to find and follow Ebonie, as well as links to where you can watch her series Nomad Generation, where you can watch her film Night Riders, which I highly recommend, and how you can learn more about Safety Wing and see if that’s right for you and exactly how much it would cost. You can also just go to themaverickshow.com/safetywing and find it there. But we’re also going to put it in the show notes.

Ebonie, this was amazing. Thank you so much for coming on the show.

Ebonie Finley: Thank you for having me. This was so lovely. I didn’t finish my kombucha. We were talking too much and having too much fun, but it was awesome. Thank you.

Matt Bowles: All right, good night, everybody.