INTRO: This is part two of my interview with Derek Baron. If you have not yet listened to part one, I highly recommend that you go back and do that first because it provides some really important context for this episode. Part one was episode #253. If you have already listened to part one, then please enjoy the conclusion of my interview with Derek Barron.

Matt Bowles: Well, another place that I want to ask you about is your experience traveling in Yemen. And I want to ask you also, particularly about going to the island of Socotra, and for people that have never heard of the island of Socotra, can you share a little bit about what it is, why it is so unique, and what your experience was like there?

Derek Baron: Socotra, definitely look it up because it is an island that is sort of equidistant off the coast of Yemen and Somalia, and it is part of Yemen. Quite remote when I went there. So, they were getting an average of about 700 visitors per year. Even now there’s only, I think maybe one or two flights there per week. And it’s about 50, 000 people that live there, but they’re quite isolated as you can imagine. And with all that, that’s not even the fascinating part. The fascinating part is the island itself. From the moment you get off the plane, you’re basically stepping into a fairy tale or maybe an acid trip is more like it.

It’s surreal. They have trees, plants, and flowers that cannot be found anywhere else in the world. The landscapes are surreal. You have these huge sand dunes, pure white sand leading hundreds of feet down to the most gorgeous water you’ve seen. With the still to this day, everyone talks about like their favorite snorkeling sites and stuff like this.

There is a reef off of Socotra with nobody there. It’s the most incredible snorkeling I’ve ever seen, uh, just marine life anywhere on the planet. Mountains, there are caves, lakes, you name it. Canyons and just little villages scattered around the island. I think about 50,000 people live there. It’s really just, it’s all trip. I mean, it’s Alice in Wonderland, such a trip. Not many people go. Well worth visiting.

Matt Bowles: Now, did you go to Socotra from Cairo, or did you actually go to mainland Yemen and then go out to the island?

Derek Baron: So, I went to the mainland Yemen. Uh, so I was with a friend on that trip, and we went to mainland Yemen for about, I think about eight days first. And then we flew from Sanaa, the capital of Yemen to Socotra.

Matt Bowles: And how was mainland Yemen? What was your experience like there?

Derek Baron: Yeah, mainland, I’ll always say that if Yemen was safe, it would probably be one of the most visited countries in the world because it’s not much like it. I mean, it used to be super popular with cruise ships way back in the, like the eighties, nineties, and stuff. They have these cities that are, you know, they call it the original Manhattan, which is these massive, uh, 15-floor skyscrapers made out of mud that are 700 years old that are still inhabited. And it’s just nuts. And you know, all these towns and villages that are built, not on the ground, but built on the side of mountains and cliffs are on top of the mountains in the most insane places.

Yeah, it was, it was a pretty incredible trip. And, uh, I will say like when I went there, if there’s an American traveling in your group, this was just me and my friend. When you get to one region, the government sends armed soldiers to accompany you. So, there was one region due to some kidnapping concerns.

So, in one region of the country for a couple of days, we had armed soldiers that were, you know, circling around us as we walked everywhere. But I mean, it was just for extra precaution because everybody we met there was absolutely lovely and we had just every day was endless rewarding experiences, weddings, and celebrations, dancing, it was crazy.

Matt Bowles: Well, I also want to ask about your experience in Syria. Can you share a little bit about how long you were there and what that was like?

Derek Baron: Yeah, that’s another one where I planned to go for two weeks. I ended up spending six weeks there because surprise, it was nothing like I or anybody else who, who was trying to convince me not to go thought it would be like, and I went and it was, my first stop was Aleppo in the North.

Man, it was such a beautiful city. Horrible. Obviously, all the stuff that’s happened since, and a lot of friends that I made there that have all had to leave and had their hotels, like the hotel I stayed at was pretty bombed and pretty rough. But back then it was not what you would imagine, just such quite open-minded.

And it was, I mean, I was in an underground bar in a cave underground in the middle of Aleppo, partying with people. I mean, stuff was just happening that you would not have thought in Syria. And the people were so friendly. And I’ve mentioned before, I’m Jewish and people don’t tell them you’re Jewish. You know, somebody asked, I said, I’m Jewish.

And the first response was, oh, let me, Show you the old Jewish neighborhood. It’s really neat. Like, and now they showed me around and I just wanted to go to more and more places. My original plan was to go to Aleppo and Damascus. And in the end, I ended up going all over the country.

Matt Bowles: And what year was this that you were there?

Derek Baron: So that was about 2011.

Matt Bowles: Well, one of the places you’ve been to a lot more recently that I know has made a big impact on you is Iraq. And I have not yet been there, but in listening to you talk about it, it has really moved high up my list as well. Can you share a little bit about, I guess, your initial, uh, experiences in Iraq, and now you’re running tours and taking other people there and so forth. So, can you share a little bit about what it’s like in Iraq and the impact it made on you?

Derek Baron: For sure. So, the first time I went to was actually to Iraqi Kurdistan, the autonomous region in the north, actually after Syria, so about 2011. And at that time, I remember I was with a friend, and we were trying to leave the autonomous region to sort of take a shortcut through federal Iraq.

We were stopped by us soldiers at the border who were like, you can do it, but don’t get out of the car. And it’s not what it seems like it is pretty dangerous. So, we did it. It was fine, but we could tell it was not the wisest thing. So fast forward to last year, I had heard of federal Iraq, opening up more to tourism with visas on arrival, and a couple of friends and I said, “Let’s go”. And we went to Baghdad, went to South Iraq, and it was phenomenal. And not at all what anybody would imagine. So, after that, with our tour company, we started putting together tours. So, we actually had one in March and I’m actually going in two weeks. So yeah, in two weeks, I’ll head back to Iraq for the next tour.

And it is, it’s, I mean, tourism is proper. You get a visa on arrival at the airport. The infrastructure is great. The people are incredible. The food is amazing. The sites are historical sites that blow anything away that you’ve seen anywhere else, and they’re just sort of sitting on the side of the road, their city, 6,000 years old, and God knows why it’s mind-blowing.

Matt Bowles: Can you talk us through a Wandering Earl tour? If somebody wanted to go on, for example, this tour to Iraq, what does the itinerary look like? What is the experience like? How big is the group? And maybe for the previous groups that you’ve taken, what was their kind of impression at the end of the tour?

Derek Baron: I will say, so just to go to the last question, first, the last group that we took in March to Iraq, I mean, by the end of it, I mean, people were in almost in tears because it was such as a beautiful experience and such a touching experience.

We’ve had so many people who shared their stories with us and really created a lot of close bonds and just, just saw some of the most incredible places that you can see on this planet. Obviously, it’s very safe over there right now. And it just, that concept of going to a place that. Is so different than what you or anybody else imagines.

It really has a very powerful effect, you know? So that’s one incredible thing about this trip. All of our tours, a small group, have a maximum of 12 people. The idea is that they’re all based on my own personal travels and my own personal contacts and connections and friends in each country so that this way we’re able to do stuff that pretty much other travelers are not able to do and this goes for all the tours that we run in all the countries if they’re even in Iraq we do some things that no other travelers are able to do just because of our local friends that are able to get us the permits and the permission to do those things. So, that’s the style of our trip.

They’re a small group. We treat it like a group of friends. We don’t walk around with signs or stickers on, you know, with your name on them. We keep it very relaxed, and flexible. We go with the flow, just like you want a good travel experience to do. And we mix up, you know, obviously you see the main stuff that you’d want to see, but so much local interaction and just hanging out with people and really getting to know a country. And that’s, that’s always at the heart of all of our tours. It’s just. coming away with just a real local and interactive experience.

Matt Bowles: I love that, man. I mean, in all the research that I’ve done about your tours and what I’ve read about them, I love a couple of things that really stand out to me. One, obviously, is that you’re literally having your local friends lead these and design these and help people to immerse in the local culture.

And it’s actually more about the people and the local interaction with folks than it is about the sites and the things that you’re going to see and take pictures of. And also, the thing that I like about it is that you design the tours sort of in the way that you travel, which is that you leave a lot open for flexibility so that if certain things come up, you can just sort of take a deviation or a left turn or, Oh, now you just got invited to this thing.

So, guess what? You can change plans and go to this thing, and you sort of the, the wandering or old style of travel as applied to a small group tour such that no two tours of that you offer even to the same place are going to be identical because you allow those local experiences to unfold and take shape as they normally would. I love that, man.

Derek Baron: You learned it too, I’m sure, from your travels. You have to have that aspect. And we figured out that there is no reason, just because it’s a group tour, an organized group tour, that it can’t have that aspect of it too. Because that’s so important, all those surprises. You don’t want to say, oh, we can’t attend this wedding that we were just randomly invited to. Or we can’t go to this home that we were just invited to because we have got to be here by three o’clock and we have to get out of the road now. So, we don’t want it to be so structured that we have to say no to the beautiful, unexpected surprises that travel provides along the way. So, we make sure we include those on the tours.

Matt Bowles: Well, another destination that you run tours to that I have also not yet been to is Central Asia. Can you talk a little bit about the Kyrgyzstan and Uzbekistan tour experience and what it’s like in Central Asia?

Derek Baron: It’s a funny region because it’s one of the last regions almost that people think of even to visit, it just doesn’t come up that much in conversation.

You don’t see it on too many lists of places I want to visit or stuff like that. Not too much is known about them. Obviously, they are spectacular destinations. And I think what you have over there is that fact that there are not many people over there, especially Kyrgyzstan. Which is this mountainous country with nomadic people and just beautiful villages and definitely some of the most impressive landscapes you’ll find anywhere.

And still with this traditional way of life and very few tourists. I mean, it just makes every place you go genuine. There’s very little that’s set up for tourism. So, they are actually trying to increase their tourism in a very sustainable way. So, it makes for a great experience and we love running this tour and people love going on it. I mean, they absolutely are blown away, blown away by this region. Every time we have groups going.

Matt Bowles: Well, one of the things that I also really appreciate about your tours and the way that you’ve structured your company and designed your experiences is you’ve really paid attention to making a positive impact on the local people and places where you’re going.

I want to just read an excerpt from your website at wandering girls tours, and you say, “We make a point of avoiding mass tourism destinations. Instead, we sustainably support local businesses, communities, and the environment everywhere we go. Every aspect of our trips from accommodations to local guides, activities to meals and everything in between are chosen to ensure that your tourism dollar leaves a positive and lasting impact and that our visit leaves a minimal footprint”.

Can you talk a little bit more about that and the importance of ensuring responsible, respectful, and sustainable travel experiences?

Derek Baron: For sure. And I think a lot of it is what happens, especially with big tour groups and stuff. A lot of the money that is spent doesn’t actually go to people in that country or it goes to big, huge businesses that are basically running everything.

So, we make a point, we don’t make any contracts, like long-term contracts with big hotel chains. We don’t make any actual long-term contracts with any aspect so we have the freedom to improvise and change things around. And we choose every aspect of the tour, whether it’s transportation to accommodation, to the places we eat, to make sure that the dollars that are spent are going directly to people and their communities.

And I think that’s like you said, that’s a, it’s a huge aspect of it because it’s very easy to travel and not be aware that your money isn’t really going. To the people around you, big hotel chains that are owned by companies outside of that country. Well, the majority of the money is going to out of that country as a result.

And I think it’s easy to just, just not be aware, which is fine. You know, we just try to focus on it. Sure. Maybe we’re not going to stay in the most beautiful four-star hotels everywhere we go, you know, but we stay in a lot of amazing places. Like people really do love the accommodations that we choose.

And, you know, for example, in India, I’ve really good friends with a family that runs just a beautiful family run guest house in Agra near the Taj Mahal. And they cook meals for us. And it’s just, its simple, private rooms, private bathrooms, very comfortable. It’s simple, but it’s not luxurious. And, uh, it’s going straight to this family, and they hire other people from the community and, you know, we support them. And, and that’s how we look at every aspect of the trip. And we literally do look like day by day, every aspect of the trip. How can we make sure that this hour, the money gets spent in the right places? And I think that’s extremely important.

Matt Bowles: I appreciate that so much about you, man. And I think a lot of people don’t realize, I mean, and even me as a traveler, like I don’t even realize a lot of times when I’m spending my money, where is it actually going? I mean, people can Google the concept of tourism leakage. And you can start to see all of a sudden, there’s all these studies been where it’s like, you think you’re putting money, you know, into these places when you’re traveling. But in fact, the amount that actually gets to the local people versus that gets diverted to a lot of these multinational corporations and things like that is a lot more than you think.

So, you have to be intentional about it.

Derek Baron: It’s huge. And the crazy part is like, you can go to a place and then you have all these, say, you’ll hear, you know, a lot of travelers complain, Oh, the locals here, they’re so pushy, they’re so, they’re trying to rip us off, they’re trying to cheat us, and the problem is, I get that, and obviously that’s not a fun experience, but a lot of that also comes from the fact that they’re not benefiting from the hundreds of thousands of tourists in their city, and they’re not benefiting from it.

And, you know, so when you go to some places where there’s a lot of people who are trying other means to get some tourism dollars, some of them not so fun for the tourists, often there’s a reason behind it. They’re just not benefiting from the millions and millions of dollars that’s being spent in their city or town every year.

Matt Bowles: I want to get your perspective on some larger issues that I’ve started to try to think about recently. And I think you have some unique perspective because you’re both a traveler and you’re also involved in the tourism industry now. So, I think you have some pretty unique perspectives on some of these things.

And I’d love to get your take, first of all, on the concept of over-touristification. And if you look at places like Venice, Italy, right, which is a pretty obvious example, right? Or even places where I know you spent a lot of time in Playa del Carmen, right? I was just down in Playa over the last year and a half there.

And sometimes it’s just like, wow, man, like some of the tourism infrastructure and stuff that has been developed, has really just destroyed and displaced a lot of the local culture in a lot of these places. And I’m wondering how you think about that, you know, just from a macro level in terms of what’s going on there and maybe what needs to happen to change that.

Derek Baron: I mean, it’s a tricky one because it’s not any one side’s fault. Like it’s nobody thought it through. So obviously the local governments didn’t think it through. They see the tourists coming. So, if there’s no plan to handle it in an appropriate way, then we now see what the result is. And obviously for tourism, especially with social media, everybody’s seeing the same spots that you have to go to these days.

And everybody, I think I read some crazy statistic that 60 percent of travelers are making their decisions based on Instagram, you know, or places they’ve seen. So, there’s that aspect. They’re just going to where they see people are going and you’re supposed to go to, unfortunately. So, I think there needs to be some combination from both sides to reach a solution.

Obviously, I’m sure these destinations want tourism money. But there needs to be a plan in place, whether it’s restricting numbers or something hardcore like Kyrgyzstan, which is really working hard to make sure that they are not getting mass tourism and they’re building it slowly, but with quality tourism, they have a great plan in place.

And unfortunately, most countries don’t think that far ahead. I get it. It’s obviously horrible prices rise and then it pushes locals out and they can’t afford their own city anymore. Or, um, like you said, a lot of the culture sort of disappears in favor of just ice cream shops and souvenir shops and stuff like that.

But again, there’s a plan. Everybody’s going to kind of go where the money is, you know, especially if your traditional bakery isn’t making money, but you can, you can make 10 times more selling magnets, you’re going to open up a magnet shop. I mean, That’s just simple. I feel like there just needs to be an overall better management of how to handle these mass numbers.

The crazy part to me is that there doesn’t seem to be much thought going into it. That’s the crazy part.

Matt Bowles: And I think there’s another version which I think is similar in some ways, but also different in other ways with the rise of the digital nomad movement and the number of remote working ex-pats, particularly that have accelerated since the pandemic and some different trends that are arising and challenges that are arising with those media to longer-term expats versus just the touristification, right?

And so that’s where, you know, you’re starting to see in cities that you and I both love, like Lisbon, Portugal, and other places where we both have a lot of friends. And I could go down a whole list of these sorts of nomad hotspots if you will, as they’re known, but a lot of the stuff that’s going on in these places, as you have such a gigantic rise of.

People that come from countries where they make a lot more income than the locals and they want to come and they want to stay for medium and long-term durations, as opposed to just coming in for a week on a tour. Now, all of a sudden, you’re really getting some of these gentrification dynamics that are pushing local folks out and that is changing some of these dynamics, which is a little bit of a different version of the problem, I think, than just the touristification. And I’m curious if you have thoughts on how we as long-term travelers can make the most thoughtful decisions as we’re designing our travel lifestyles and making our travel decisions in terms of doing the least amount of harm, making the greatest amount of positive impact on the local people in the places where we go.

Derek Baron: I mean, to be honest, the best thing we could do is not go to those places. Like that’s it. I mean, unfortunately, like even in Lisbon, it’s pretty predictable. What happens when you offer digital nomad visas and X thousand number of foreigners suddenly show up. So, it’s like, to me, shocking that there wasn’t a plan in place.

If we want to just as the travelers or the other nomads want to really make the biggest difference, it’s unfortunate because things were not properly planned not to go there. That’s literally the best we could probably do in terms of helping people not be pushed out by high prices. If you do go there, and the main thing is just to make sure, I mean, the problem is like in Lisbon, for example, as you’ve seen, you see the, you know, the local coffee shops being replaced by the hipster coffee shops, right?

Which are often owned now by foreigners who are living there. So yeah, the key is just to spread your money. It’s kind of like what we do on the tours, you know, make sure that when you’re spending your money, that it is going to people who. Needed, you know, small shops, small cafes, small restaurants where they are.

This is their life. This is their livelihood. They’re on the border. They can, they’re paying rent every month. They need to survive and go help them out. Not the coffee chain that’s, you know, has big corporations behind it to invest millions to get them going, going well. I mean, that’s, that’s the best you can do.

But it’s a really tricky situation because like, again, it’s pretty predictable what would happen when you have this amount of people show up from outside and yet nobody plans, like nobody plans for it. And it’s going to happen even more with even more countries offering these visas. And again, you can’t really blame people for going after the money either. Like, yeah, so it’s a pretty big mess. I don’t, I don’t see a clear solution.

Matt Bowles: And when you say it might be good to not go there, do you mean it might be good for people to think about going to places other than these nomad hotspots and being intentional about selecting places?

Derek Baron: Yeah. Like where your presence isn’t going to have that kind of an impact. It’s not going to, uh, necessarily lead to say the crazy increased prices and people being pushed out. With that said, I get it. You’re probably not going to want to go spend time in a town in the middle of nowhere Portugal that nobody’s heard of. When all your friends are in Lisbon, it’s also not reasonable.

That’s sort of part of the appeal of going there is to have that community and to have access to all of that. That’s the tricky part. Sure. There are other places that you can pick around the world. Romania now has a digital nomad visa. So, you can go there and go to beautiful cities like Sibiu, Timisoara, stuff like this, were, yeah, there’s not huge, huge communities of digital nomads at the moment.

So, it’s not having a huge effect, but again, part of the appeal is you’re going with other people who are like you are living for a reason.

Matt Bowles: Well, in part, right. In terms of if you want to interact with other travelers and expats, but I think in terms of the way that you travel and the way that I travel, I mean, a lot of the priorities for us is to actually get out of some of those bubbles of other expats and nomads and really connect with local folks and stuff.

And in that spirit, Derek, some of these places that you’re leading your tours to, like in Central Asia and in Iraq and stuff like that, would you recommend some of those places for more medium term remote work locations, like just go post up in Baghdad and spend extended time there?

Derek Baron: It is actually very possible. I mean, you can only get a two-month visa, but it is very possible to live there. I still don’t know myself what it would be like to live their long term. The traffic would probably drive you nuts. But apart from that, it’s definitely possible. There are actually online communities of Iraqis who are interested in meeting foreign travelers.

So, you can join up with one of those online communities and they have meetups all the time and you’d meet some cool people. So that, I mean, it would be a pretty cool experience. Bishkek, the capital of Kyrgyzstan. That has a little bit more of a community. Very nice city. Easy place to live and very friendly people and very close to all the incredible nature of the country.

So, I could see something in like Bishkek being a pretty popular place eventually.

Matt Bowles: Well, I also want to talk with you about some of the dynamics that come along with long-term itinerant travel as a lifestyle. You have been doing this for 23 years now, and I want to ask you about some of the sustainability dynamics that have allowed you to create a life of long-term world travel that has been joyful, fulfilling, and exciting for two decades. Can you share a little bit about what some of those sustainability pillars for you are? So

Derek Baron: first and foremost, I will say, if I was traveling to see the sites, I would have stopped after probably two years maximum. So, for me, and still to this day, it’s the people. So, I find it fascinating that if I don’t travel, there’s all these people out there in the world that I will never come across who think differently or have different cultures, different religions.

And that is a thought that I cannot let go of. I’ve never been able to let go of it. And that’s literally what drives my travels are like. But there are more people out there who are different than me yet the same. And I want to learn from them and meet them and have this cultural exchange. That’s what drives my travel.

So that’s always the core of everything I do in terms of that. And that’s that. Yeah. That’s what’s kept me on the road to be honest. I mean, that’s what’s kept me on the road.

Matt Bowles: I agree entirely. I feel exactly the same. And one of the cool things you and I are both in North Carolina now, and we’re kind of doing this swing through the United States.

And one of the cool things that I’ve noticed is that perspective gives me. When I come back to the US and I’m just here in Asheville and I’m going out to a local restaurant in Asheville, all of a sudden, my perspective and the types of things I’m attentive to and the types of conversations I’m interested in initiating all of a sudden become very different.

So, I went to an Indian restaurant in Asheville. And I asked the guy, “Where are you from?” And of course, he just tells me “I’m from India”. And so, then I’m like, “Fantastic. Where in India are you from?” Now, most people don’t go that far. They don’t ask that question. And before I started traveling, I didn’t know that I would have asked that question.

And then he tells me “He’s from Punjab”. And then I’m like, oh man, I spent 2017, I spent Diwali in Amritsar, and it was amazing, and I had this experience, and we started talking about that stuff, and then, because I follow Indian politics, I’m like, oh yeah man, and the farmers protest, which by the way, for folks that don’t know, I’m like, oh, The Indian farmers protest in 2020 was literally the largest protest in the history of the world, where 250 million Indian farmers shut down the country to protest the privatization of agriculture and a number of other things.

But I started talking to him about that. And the Punjabis, of course, were at the lead of that protest. And they won, by the way, which was amazing. And so these are conversations because of my travels and because of the people that I met, and because of the things that I therefore pay attention to, you’re then able to go anywhere in the world, even Asheville, North Carolina, and all of a sudden the conversational avenues that open to you and the types of diversity you’ll observe and the conversations that you now are positioned to have with people is just incredibly different.

Derek Baron: Oh, 100%. I mean, it’s an entirely new avenue of connection, basically. And it’s just on a whole different plane than you absolutely would not have had if you didn’t get out there. And I, that’s what I love. I mean that, like that, that example of that interaction is, I mean, to me, that’s what it’s about. I mean, that’s what it’s about.

You are connecting with other people on a completely different level than the normal superficial everyday chit chat. It’s beautiful.

Matt Bowles: I want to talk to you about the itinerant nature of your life and moving around from place to place, which is very different from an expat. Life where somebody is like, I’m just going to move to this other country and then settle in and then get an apartment and then live there.

And yeah, it’s a different culture, but they’re sort of based in one place. The itinerant nomadic lifestyle is a different situation altogether. And you’ve been doing that now for a lot longer than I have. And I want to ask you in general, just about your, uh, acclimation techniques that you use when you land in a brand-new place, any stability anchors that you use as you’re moving from place to place, culture to culture, language to language to create a level of consistency or feeling like home. How do you do that? And what tips do you have for folks?

Derek Baron: I mean, for me, there’s really two things. The first is I try to go on either Meet up or Facebook, just to find a local group, just people I’m meeting quickly. I feel like that’s always important is within the first, say, few days, a week of being somewhere, it’s very important to be interacting and meeting people.

I find if you can do that, then that sort of jumpstarts your experience there. If it takes a while or a little bit longer than that to meet people, it can kind of drag on and then affect your experience in a negative way. So that’s always the first is try and just at least find some people to hang out with.

Even if it’s once, just something to have that social connection and interaction. Second for me is routine. It’s not the most ideal routine cause I’m moving around all the time, but since I do work online, for example, I will always make sure I don’t like to work where I sleep. So, I will make sure I get up in the morning, get ready, get my laptop, find a cafe or a coworking space to go to do my work for a few hours.

Make sure I stay in that routine. Make sure I still. Do my exercise as much as I can in the afternoon, just to keep that going, at least me feeling good mentally and physically. And I feel like that helps me because it has nothing to do with the actual destination. So, I can just take that and implant it in any country, any city, any town that I’m in anywhere in the world. And I have a little bit of stability to then build the entire experience off of.

Matt Bowles: One of the questions that I get asked a lot about the itinerant nomadic lifestyle is how does dating and relationships and finding love work in this lifestyle? Can you share any tips or reflections that you have on that?

Derek Baron: You’re going to meet a lot of people, which is a bonus. I mean, I find that the great part about it is that you’re going to be meeting people from all over the world all the time. So, you actually get quite a nice diverse range of potential matches. We’ll say with that said, everybody in this lifestyle has their own shit going on.

So that’s the tricky part too. You have to make a lot of hard decisions. The chances of finding somebody who can just pack up and just do exactly what you’re doing and that you want to go to the same places is pretty slim. So, if that happens, you kind of need to make some big decisions. You’re either stopping your traveling or seriously altering them to match up with somebody else, obviously.

So, it’s some interesting factors that you don’t have. If you’re just sort of living at home in one place, I mean, it’s not that high, I mean, I had long-term relationships and, uh, there’s a whole different set of challenges that most people don’t have to think about. And I guess eventually you just decide you have to make some big decisions.

Matt Bowles: Yeah. I mean, that’s kind of what I tell people, right? Like the benefits are incredible, which I explained to people are that a regular person who lives a normal sedentary life in a city, their dating universe is the human beings that are in driving distance from their house. Whereas, my dating universe is the planet of earth, which is extraordinary.

And the other thing is that I tell people is that my location independence gives me the flexibility to make those decisions. Whereas other people don’t even have the option. If the love of their life is in Bangladesh and they have to stay in Bangladesh and that person has to stay in the United States like they don’t even have an option.

Whereas I have an option to go by where the person needs to be and if it’s the person that I want to be with and then you have all of these choices right in terms of that and then as you said, it’s just a matter of decision making and prioritization and all of that kind of stuff so

Derek Baron: Which in all fairness, I will say like most people don’t want to travel nonstop for 23 years. It sounds cool, but when I start to explain the challenges, most people are like, okay, maybe I’ll do a couple of years, like, you know, so for most people, if, if they, if it does work and they find somebody, you know, there’s a high chance that you can make it work if you’re not addicted to this lifestyle.

Matt Bowles: And there’s a lot of different ways that you can structure this lifestyle. And I want to actually ask you about that next in terms of when you think back on the 23 years of travel that you’ve done, can you talk a little bit about some of the different lifestyle design choices that you’ve made at different phases of that different seasons of your life and how you’ve integrated and maybe changed the way or the style in which you travel?

Derek Baron: For sure. Yeah. I think definitely you have that in the beginning. It was that just absolute fascination with the world phase where the way I look at it is I would rather spend $1 to sleep in the most horrendous, hostile dorm room. If that meant I had $5 to go see some other place during my travels. It’s kind of that whole thing, which was amazing.

I did that for quite a while. But then obviously when I started working for myself and having the travel blog, and I was like, Ooh, I kind of have to work like. You know, before I was working on cruise ships. So, I teach in English now. I was like, oh, I kind of really like it’s up to me now fully. So, I need to make sure I’m a little more comfortable.

I need to make sure I’m a little more focused. So, things start to change a bit and I wouldn’t just pick any destination and just go there. I think that’s the thing. It went from like, I’ll go anywhere. Absolutely. Anywhere, wherever the cheapest flight, where if I’m in Bangkok, wherever the cheapest flight, whatever country that is, that’s where I’m going.

Then it starts to become, well, I probably should make some, you know, good, better decisions and, uh, you know, over time it just changes to now I kind of decide I have to structure things a little bit more. Okay, I still love to do like really remote and exotic travel and stuff, but if I’m going to do that, it has to be a period where I don’t need to be online all the time or, you know, doing a lot of work and then when it’s time to work, I need to be somewhere where I’m a little more comfortable to make sure I get my work done efficiently and take it seriously.

And obviously, just get stuff done. I think the more responsibility you have, the more you have to really pay attention to how you structure your travels. And that initial stage was a blast though, where you were just $16, I can fly to Malaysia. I’m going, and then you find like. Back then it was always hostile for a dollar. It was awesome. Yeah.

Matt Bowles: And I think that’s the beauty too. I mean, I always tell people location independence for me is just the freedom to make these choices, right? And if at some point I feel like I’m traveling too fast, I’m traveling too quick, I want to just stay in one place for an extended period, I can do that. And then if I’m staying in one place for an extended period, I feel like I need to travel more. I can do that, right? And so, it’s not that there’s one particular formula of the lifestyle that is inherently what you should strive for. Rather, it’s just paying attention to yourself. I feel checking in with yourself and you know what you feel that you need can definitely change over time. For sure,

Derek Baron: For sure. And I think it has to. Honestly, if it doesn’t change over time, something’s wrong. I mean, it really means that you’re not paying attention to yourself and that that can get a bit dangerous because you can lead to burn out or just not being satisfied or not actually enjoying your experiences.

You might just literally be addicted to travel and not actually enjoying the freedom and the actual experiences. So, I think it’s, it’s quite important to make sure that it changes because. No human being will go through an extended period of time without having different needs, wants, and desires, so I think it’s only natural to change.

Matt Bowles: Derek, when you think back on the 23 years of travel that you’ve done, what are some of the major impacts that you think it has had on you as a person?

Derek Baron: I think one of the biggest things is not to trust anything until you experience it for yourself. I think that’s a big thing. I mean, not that it’s any secret, but you really see that a lot of the major issues in the world, especially when it comes to politics, or anything literally conflict over.

Nothing. Misunderstandings on all sides. People thinking they know, even though we don’t know me, myself included, obviously for tons of stuff. So, I think that’s one of the biggest lessons I learned is that when you go somewhere and you meet people and you talk to people and you actually see how things affect their lives and you get just that firsthand experience and understanding. That’s when you can kind of say, I have a little bit of real knowledge and I can make sort of reach a real conclusion about certain topics. And I think that’s extremely important. And sadly, something that’s just dying these days, like nobody even cares that that’s a truth.

People are more than happy just to believe anything they see quickly in a shiny ad or a social media post. And sadly, that leads to a lot of issues that could be avoided. So, I think that that’s by far the biggest impact. And the second, and which is tied into that is, I think I mentioned before a little bit people everywhere are good people.

Everybody wants that same stuff. It’s just, people don’t want to hate. People don’t want to kill other people. I mean, that’s always what it is when that’s the difference. When you have the firsthand experience. You see the reality and you realize that, you know, people are just good people everywhere. And that’s, that’s been super powerful for me.

Matt Bowles: You’ve been to 133 countries now. Why do you continue to travel? What does travel mean to you today?

Derek Baron: I will say it’s probably 25 percent addiction, just like anything else. When you travel and you travel for 23 years, I know travel. I know how to travel. I know how to get adjusted. You can plot me down anywhere in the world.

I can get adjusted, meet people, have a great time, gain some valuable insight, and learn a lot. I don’t know how to stay put in one place. I literally have not done it for most of my adult life or all my adult life. And I think that’s a big part of it is that just like anyone I do what I know best, you become addicted to that.

And then you kind of get in that cycle. With that said, it obviously provides me with a, with a lot of benefits as well. And I think part of it is freedom. It’s that freedom of whatever I need at a particular time, whether it’s to hang out with a community of friends, I can go to a place where I have friends.

If it’s just needed to get it out into nature to clear my head. I can go out into nature somewhere, clear my head of it, somewhere totally off the beaten path, exotic that I want to have that kind of experience, I can go do that. Somehow this lifestyle has made the world quite accessible for me. I feel very fortunate that that’s happened. I just get to have a lot of experiences in life that lead to quite a fulfilling time on planet Earth during my short time here. So, I want to keep it going.

Matt Bowles: How do you think about this concept? I’ve come across an increasing number of people that have a really specific defined goal of going to every country in the world.

Actually, I’m sure that we both know people who have every 193 passport stamps or whatever, is that something that has ever entered into your mind as something that’s important, something that’s a goal, something that you’re striving for? Or is that a very different type of travel framework in thinking?

Derek Baron: It’s not something that I strive for. I mean, I prefer to just let the experiences go, which is the reason why I’ve been to India 40 times and, Romania 40 times. Had I not been 40 times, I could have taken those other 39 trips and each of those and gone to different countries and probably gone to all of them, but I want to go where, where it makes sense for me personally at that time to go, I mean, that’s it.

And if it’s the same country I’ve been to 40 times, so be it. If it’s a new country, that’s great. I just, yeah, I don’t have a desire to just, I mean, it would be awesome if it eventually took me to every country, but it’s not a goal. I feel that’s a very, I think a lot of the people that do it, it’s a very just structured goal.

That’s the goal. It’s a different travel. It’s just specifically for that purpose of saying that you’ve been to all the countries, which is fine. I mean, it’s a goal like any other, but yeah, it’s just not my style. So yeah, awesome.

Matt Bowles: I agree with you, my friend.

Derek Baron: I had a feeling.

Matt Bowles: All right, Derek, I think that’s a great way to end the main portion of this interview. And at this point, are you ready to move in to the lightning round?

Derek Baron: Bring it.

Matt Bowles: Let’s do it.

Alright, what is one book that has impacted you over the years you’d most recommend people should read?

Derek Baron: I would go with Never Split the Difference by Chris Voss. Just an interesting book on how to communicate with people.

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

Derek Baron: It’s just a travel rule is when I arrive in a new place, say you fly into a new country, wait 20 minutes, go to a cafe when you land, go sit there for 20 minutes before you make any decisions and walk out of the airport because we make a lot of bad decisions such as I did in Bangladesh. If you don’t take a few minutes to get acclimated to where you are.

Matt Bowles: All right. 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.

Derek Baron: I’m going to go with Steven Wright. He’s my favorite comedian. His very dry, simplistic approach to life’s oddities. Is very much in line with my own.

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

Derek Baron: Don’t let anyone tell you that there’s a particular path. If there’s a little bit of something in your head that excites you and it’s not what everybody else is doing, follow it. See where it leads. Don’t worry about it. Things will work out eventually. Just keep trying and don’t get locked into a certain path. I figured it out eventually, but it would have been great to know that at that age.

Matt Bowles: All right. Of all the places you’ve now been, what are three of your favorite destinations you would put people on to most recommend people should definitely spend some time in?

Derek Baron: I would say Japan. I’m a bit of a beach person, so I am going to say the Seychelles because it’s quite spectacular. And I’m going with Iraq because it is really an experience like no other at the moment.

Matt Bowles: All right. Last question. What are your top three bucket list destinations, places you have not yet been, highest on your list you’d most love to see?

Derek Baron: I’d probably go with Mongolia. Namibia, for some reason. I just haven’t made it there, but I really want to go. And the third is Pitcairn Islands, which I’m not sure I’ve heard. It’s a British overseas territory in the middle of the Pacific Ocean. That is inhabited by, I think about 50 British descendants of some people that arrived there about a hundred years ago.

Matt Bowles: Wow. All right. Derek, I want you to let people know at this point, first of all, how they can find you, follow you read your blogs. You have a lot of amazing articles about a lot of incredible places, a lot of incredible experiences. A lot of incredible perspectives and reflections on your travels that I think are really important for people to dive into.

I have been down a rabbit hole reading through your stuff. It was really incredible. Even 10 years full-time travel, I’m getting a lot out of your content. So how can people find your blog and then also if people want to learn more about your tours and what you have coming up, how can they learn more about that as well?

Derek Baron: Sure. Yeah. The blog is wanderingearl.com and all my social media is wanderingearl. The tour company is wanderingearltours.com. There you go. And yeah, you can find, we have all the tours listed, uh, for next year out there. Right on, on wanderingearltours.com. I love interacting with people. It is why I travel.

So, if anyone has questions or anything, uh, about any destinations or anything that they might be planning with travel. You know, you can always get in touch with me. I always reply to everything and am always more than happy to help out if I can.

Matt Bowles: Amazing. We are going to link all of that up in the show notes and for Maverick show listeners, if people are interested in doing one of your tours, are you able to offer them a special discount just for listening to the Maverick show?

Derek Baron: For sure. We can definitely do that. We can offer you a hundred-dollar discount on any tour. Um, that’s no problem. And, uh, you simply sign up for a tour, you’ll receive a confirmation email from our team, and then they will confirm with you that I just let them know that you came from the Maverick podcast, and you will get your discount. Pretty easy.

Matt Bowles: So, we are going to link all of that up in the show notes. You can just go to one place at themaverickshow.com and just go to the show notes for this episode. There, you’re going to see the link to where to check the tours out and exactly how to get your $100 discount. And you can use that on any of the tours, if you want to go to India, Romania, Iraq, Kyrgyzstan or Uzbekistan, any of these places, you can get a hundred dollars off with that. So, it’ll be in one place for you at themaverickshow.com.

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

Derek Baron: No, man, I really appreciate you having me. Yeah, that was great. It’s great chatting with you. And I only made it through half a bottle of wine. So,

Matt Bowles: Hahaha, well, my friend, we will have to have another conversation later because there’s a lot more places in the world that we could talk about, but this was really special, man. It was great to connect. Great to drink some wine with you.

And thank you for coming to the show.

Derek Baron: No, awesome. I appreciate it. Thanks so much, man.

Matt Bowles: All right. Good night, everybody.