Matt Bowles: My guest today is Mashon Thomas. She quit her job as a middle school teacher at age 30, then built a fully remote six-figure freelance business, and has now been traveling the world as a full-time digital nomad with no permanent base since 2018. She is also the host of the Live Work Travel Podcast, and she now trains other people on How to transition out of a nine-to-five job, Build a six-figure Freelancing Business, and Travel the World.

Mashon, welcome to the show.

Mashon Thomas: Hey, thank you so much for having me.

Matt Bowles: I am so excited to have you on the show. I’m a big fan of your podcast and just you in general and what you’re up to. And we’re going to dive into all of that. But let’s just start off by setting the scene and talking about where we are recording this from today. We are on very different continents and very different time zones. I am actually on the east coast of the United States in the Blue Ridge Mountains of Asheville, North Carolina today. And where are you?

Mashon Thomas: I’m in Palawan in the Philippines. So, I think it’s an exact 12-hour time difference, if I’m not mistaken.

Matt Bowles: It is indeed. Now, the Philippines is one of the countries that I have not yet been to. I have talked to so many people about it. It is so high on my list, and I would love to maybe just start off by hearing a little bit about what you’re up to in the Philippines and what your experience, impressions, highlights have been so far?

Mashon Thomas: Yeah. The Philippines was also on my list for a very long time. All of Southeast Asia, actually, you know, you meet so many travelers and this is just an area that so many people have been to, but for some reason, it just kind of kept being out there.

And fortunately, I got a text from a friend about six or seven months ago, like, hey, I’m getting married. And I said, okay, cool. I’ll be there. When is it? And where is it? And when he said the Philippines, I was so excited because it was like, okay, this is finally it I’m for sure going. So, he got married last week in Cebu and I decided I have 30 days here in the Philippines as an American, so let’s take some time to see some stuff.

And I actually got interested in a fitness camp that was happening nearby in Palawan. So I just did the hour flight over last week and came to this fitness retreat because being on the road for so long, keeping up with the gym routine, keeping up with health sometimes can go by the wayside and I wanted to go to a place to just really get stuck in and just work from here, eat here, train here, and really jumpstart some healthy habits.

So, that’s what I’ve been doing. And just the highlights of the Philippines, absolutely incredible. It’s just that people are so friendly. I’d heard about the friendliness before getting here, but it is just absolutely true. Smiles everywhere. I’m from the Midwest originally, so I’m used to just smiling and nodding with people, and you don’t get that everywhere.

So, it’s nice to be back in just an environment that just feels so chilly, so friendly, and of course island life. Palm trees and flip-flops. It’s a good, good feeling.

Matt Bowles: I have heard that it is supposed to be one of the most beautiful places in the world with some of the clearest water in the world. And so divers and snorkelers and people that are really into the island life just rave about the Philippines.

Mashon Thomas: Yes, I’m hearing that. Just yesterday, someone was asking one of the people on staff about, okay, where’s the nearest place I can go diving?. And just yesterday, it was a hellish morning. We had beach training down on the beach, so it was hot. So, we were struggling, but beautiful surroundings. And yeah, being able to just run into the water during a break in training and cool off. Just crystal clear. You can go way out and see your feet way down. It’s mind-blowing. Honestly, I’ve been to some beautiful tropical places, but this one is just stunning.

Matt Bowles: Well, I want to do a little bit of your backstory, Mashon, and talk about how you got to the place where you are just living your best life on the islands in the Philippines. So, I think a good place to start would be all the way back at the beginning, can you talk a little bit about where you grew up? And when you think back as you were coming up, what was it that sort of developed your initial interest in travel?

Mashon Thomas: Yeah. So, I was raised in Columbus, Ohio. And I am one of seven children.  So, my parents loved the idea of having a big family. My mom was one of four. My dad’s one of five. They wanted all these kids, and I am the oldest daughter. So, I have one brother ahead of me and then five younger siblings. So that kind of, you know, set my place in life, I think, as mature, responsible. You know, I had a childhood, but I was also taking care of the other ones and just kind of being a mini mom kind of thing.

But I loved going to the library and kind of escaping into books, escaping into travel. And just the geography section, from a young age. I’d bring home these books and just want to, you know, turning the pages, just thinking back to like seeing places like Peru, you know, that I’ve now been to and just seeing, wow, all these other types of places exist.

And I could maybe go there one day. I don’t know. That was just an idea that I had in my head from a very young age. I was also homeschooled growing up. So, I was raising a very conservative family, homeschooled. They were super Christian, Midwestern values. It was kind of odd to go out and do anything other than what everybody else was doing around you.

And travel was a way to dream outside that box. My mom can even say, when I look back, I always knew you were the one that was going to go far away. I’m going to end up, you know, just out there.

Matt Bowles: Can you talk a little bit about that journey in terms of where you ended up going to college and then how you ended up choosing to study abroad and what that experience was like?

Mashon Thomas: Yeah, I wanted to get away from a very young age in the sense of not that things were bad, but just to see more of the world. So, I applied to colleges all outside of Ohio, because I was determined to just go somewhere else, but ended up going to Toledo, Ohio, because it was that last, you know, they tell you to always apply to a safety school.

I got into most of the colleges, but it was just a matter of finances and being able to afford it. Again, one of seven kids, I got some scholarships, but not enough to pay for it all. And so, it was like, okay, Toledo is going to be the smart choice. financially, but getting to Toledo and finding out, whoa, they have to study abroad.

You know, I’d never heard of such a thing. It’s so important to get around people who are different because if everyone, you know, only knows the same thing, then you’re just kind of stuck in the same thing mindset. So, I found out about the study abroad program and was determined to do it. And in my junior year, I ended up going to Spain, to Bilbao, Spain to study for six months.

And it was just the birth of, okay, this is for real now. I know that I love to travel. This is amazing. A lot of other people that I was with got homesick. I never wanted to go back. I was sitting on the bay, like, one of my last nights, like, praying, like, if there’s any way I can just stay here forever, I don’t want to go back.

I did have to go back and finish out my senior year, but I loved it. I loved being here. The struggle, I loved the struggle of learning a new language, new customs. We were sent to the Basque country to study, and that is not just Spanish. Basque is a whole other language. It’s got lots of T’s and X’s and it’s like very harsh and sounds nothing like Spanish.

You know, no prep. But it’s amazing to have those friends that I went over with now, you know, we can look back and just laugh and be like, oh my gosh, do you remember how unprepared we were? Our guidance counselor at the college told us, oh, Spain is warm. You won’t need winter clothes. It snowed like the second day.

So, it was just all that thing, but like learning how to roll with the punches, learning how to make new friends easily, how friendly people were when they learned like, you came here to study our language, wow, that’s amazing. And the locals were amazing. It was all together just a wonderful, wonderful experience.

Matt Bowles: I love the Basque country. I’ve spent about a month in Bilbao and then I went back on a second trip to Donostia, which the Spanish call San Sebastian. And for folks that don’t know the Basque country, first of all, is widely regarded as having the best culinary scene in the entire continent of Europe. I mean, the food scene there is completely next level, but to your point, the politics, the history and the culture are just so important and so interesting. And it’s just such an amazingly fascinating place to be. I just am so enamored with the Basque country, and I try to go back whenever I can.

But I’m curious also about you how are positioned there. Allowed you to travel to other places while you were there on your study abroad time. Did you get to experience other places around Europe?  Like, how was that?

Mashon Thomas: That was amazing. And it was mind blowing at the time as well, because the U.S. is so huge. We’re used to, you know, surrounding states or whatever, but being in a completely different country and just a short plane ride. We were at Bilbao Airport pretty often, my friends and I, you know, we’d hop over to England anytime we were just like, I’m homesick, I need to speak English, you know, like for the language.

Sometimes it can be exhausting. You’re studying, you’re just like, I want to go somewhere and have a one-hour conversation with somebody. And it’s just easy. It’s just natural. I think I went to England five times, actually. I mean, I met a guy and so, you know, I went over to see him a couple of times, but also going to the museums and hanging out and just being around other English-speaking people, but we went to Italy, we went to Amsterdam, we went to like eight countries, so we were all over. We zigzagged around a lot because we were just finding out about things like Ryanair and the fact that you could take an $18 flight to somewhere, just go with your carry on, your backpack, and come right back.

It was just like; we can just go to other countries for the weekend. That was just the taste of country hopping that has never gone away. And one of the things I want to bring up about that time period is that I am so lucky. So, this is 2006. I am forever grateful that I got to study abroad before phones were a thing. Really, like smartphones? Because we bumbled our way around, but we were so free. We weren’t documenting everything the way that we are now. We didn’t have Google Maps. We didn’t have Google Translate. I look back and I don’t know how I did it, especially at 21 and having never been out and seen the world.

Like, my first flight ever was to go to Spain to go abroad. I left Chicago and flew down to Atlanta, and then Atlanta to Madrid. And then all here I was in this whole new world without really the internet. Like we didn’t have a computer in our place. We had to go down to the payphone at the end of the street to use a calling card to call home.

And I remember this one scenario where I think it was the first time I went to London. I had said to my friends, you know, they wanted to go to Germany, I think it was for the weekend, and I wanted to go to London. And we had this one cell phone, this prepaid cell phone that we shared amongst all three of us. And I said, well, you guys take it in case of emergency because you don’t speak German. I speak English. I’ll just ask somebody for help. I don’t know. I mean, part of it is being 21, but I was just like, I’ll figure it out. I’ll just do this.

Matt Bowles: But it’s such an empowering thing. And I relate to that so much. You and I have so many things in common, Mashon.  First of all, we both went to college in Ohio. I went to school in Cleveland. You went to school in Toledo. We both found out after we got to college that there’s this thing called study abroad. I studied abroad in Ireland.

Mashon Thomas: Oh, wow.

Matt Bowles: You studied abroad in the Basque country. But when I was in Ireland, exactly what you are talking about, every weekend we were going off to this place or that place.  And then my roommate and I, who my roommate was also Irish American, we didn’t know him before the program, but we met there and lived together for the year. And we decided to take the winter break and just buy a hop on hop off Euro rail pass, and it could take you through like 17 countries in Europe.

And then we just went all through Italy and Germany. And we went as far as Budapest and Prague and then back to Paris and Amsterdam and all of these places. And it was just eyes wide open, like what you were experiencing. And it was also the same thing before cell phones, before any of this stuff so you had to figure out all of that stuff with a map, and by interacting with other people that were there is that you didn’t have any of these things.

And I totally agree about the value of that, but also how empowering that was as an independent person. Oh, I can just show up in a country where people don’t speak my language. And I don’t have a phone, or any electronic communication and I can figure out how to get to the places I need to get and how to navigate around and how to have an absolute blast in this city.

And I feel like that was so empowering and it puts in you this inspiration for, I want more of this. I want to figure out how to integrate this into my life. But then another thing that you and I have in common is that after that we came back and then we got into regular jobs that didn’t involve long-term travel, right? And then we both had the massive life transition exactly at the same age of 30. So, I want to go through that a little bit though. Can you talk about after that study abroad and that life changing experience, what did your professional career trajectory look like up to the age of 30?

Mashon Thomas: Yeah. So, I went from sitting on the beach that night being like, I never want to leave to going back and just falling back into the rut again.

So, I came back and finished up my senior year. I got a job as a marketing assistant and just really immediately hated it. I was like nine to five sucks. Like this is just, I don’t understand how I’m supposed to do this from 22 until like 65 and then die. This does not seem like the way that life should work.

I don’t understand why everyone around me is not rebelling. This cannot be all that we meant to do. So just instantly, not a fan. But I didn’t know what to do instead. And it happened that through my college roommate, one of the ones that went to Spain with me as well, she bumped into a childhood friend of hers one day, and he and I hit it off.

So, we started dating. He was a teacher, and he lived in Florida. And he was already a couple of years into his teaching career. I’m in Ohio. I’ve just graduated. I’m working a job I hate; I don’t really know what I want to do. So, there was the flying down to see him and, or he’d come up. And then I thought, you know what, if we’re going to have this workout, I need to be there. I can’t do long-distance things. I don’t want to do a long-distance thing, but I was nervous about moving straight in directly. So, I moved down, I got my own place. I got my own job down there and we continued to date. And over that time, I was exposed to a lot more of the teaching life.

So, this is interesting. I mean, I never went to middle school. I had no idea what that was like. So, seeing him, he did a lot of coaching, a lot of sports being around the kids. It was such a fun experience. And I thought I could do this. I could teach. Like, this seems way more rewarding than the soul-sucking job I’m in now, you know, kind of thing.

So, I got my certification. And back then, Florida was going through a teacher shortage where as long as you had a four-year degree in something, you could transfer that over and take some tests and be in the classroom. So, this is just going back to what we were talking about, about being in another place and just being like, I will figure it out.

Teaching was the same way. Between like, interviewing, getting the job, and then being in a classroom, it was like a week. You had to take your 12 credit hours or something of certifications over the next three-year period. Not even before you got into the classroom. So, it was just like, here you go! I shadowed with a couple teachers and then I had my own classroom, which is wild looking back.

I think it does say something about the education system in the States. Luckily, I just loved it, and I am determined to give my all when I’m doing something. So. In many ways, that first year of teaching was, was an absolute blast. I learned a lot, really enjoyed it and continued on for the next seven years.

Matt Bowles: And then can you talk about then as you were approaching 30, can you talk about what led up to your major life transition, and maybe talk about the role of the Dominican Republic in that transitionary moment?

Mashon Thomas: Yeah, so I was with my ex for eight and a half years, so from 22 to just over 30, and in 27, 28, 29, just like creeping up, started to notice that we were just growing apart.

Like we wanted different things out of the rest of our lives. Again, like that moment where I was just like, oh, people just go to work until they’re 65. And then they die. You know, like kind of, I was like, oh, we’re getting to 30. We just keep doing this every day until 65?. And again, I don’t see it as a failure at all.

Like our relationship, you learn amazing things from somebody, but then you also know when it’s time to separate. So, you can both do what you need to do in the next chapter. He loved teaching. He wanted to continue teaching. He still is teaching. And he thought our life was just fine. And I was like, okay, our life is fine, but I also have all these other things that I want to do.

Travel is an important part of it. We talked about that when we were younger. I still have that need inside of me. I still want to travel. And so, we just wanted different things out of the rest of our lives, you know, and I was getting burnt out teaching as well. Sadly, I think the statistic is many teachers leave in their first three years of teaching.

And I had stuck it out for seven, you know, my ex did smartly advise me, he said, if you get burnt out, maybe try a different school before you leave it altogether.  So, I tried a different school for my last year and that still didn’t work. I didn’t like what was going on behind the scenes with the state legislature, the way we test kids, like there are so many things.

But I tried that, and I was like, okay. No, I think I’m done here. I think I need to now pursue what I know is going on inside of me, working remotely. I had this epiphany, don’t quit your job and your relationship before you’ve tried solo travel. Because you used to love it when you were 21, maybe now that you’re 30, you’ll hate it.

So, in 2015, it was my spring break as a teacher, and I dusted off my passport. Got on a plane and went to the Dominican Republic for a week by myself. And it’s so funny because, yeah, the first night, like, I stayed in a hostel. I was a teacher. I still had to look at my budget, you know, and everything. I stayed in a hostel, and I was just lying there that first night, oh my god, this sucks. Like, I’m so scared. Why did I come for a week? I should have just come for, like, two days. Like, this is insane. What am I doing? I’m about to blow up my whole life or something. Ah, this is so scary. And then I woke up the next day and I walked around the city. I was in San Jose, and I was like, this is nice, I like this.

And then I did it again the second day and went and wandered and then I met some people and then they were like, we’re going up north to do whale watching. And I was like, I’m not tied down by anything. I’m going to go up north and do some whale watching too. And I ran into the same people again. And then by the end of the week, I didn’t want to come back.

But last night, the last night was pivotal. So, the last day I splurged, I stayed in a $200/night hotel. I was like, I’ve been in hostels all week, I am a grown-up, I have a credit card, m going to just trust in this and I’m going to put this on there. And I stayed in this beautiful resort. It was off-season.

So pretty much empty three pools, just the whole place myself. Amazing tropical weather. And I was, you know, kind of just hands under my chin, arms resting on the edge of this infinity pool, and I’m looking out at the water, the mountains, and I’m just like, I got to live like this. I have to live like this.

This is what I want. I don’t know how I’m going to make it happen, but I’m going to make it happen. And so, I flew back with that conviction. At that moment, it was a very big, you know, I could tell all the things that I was going to have to give up. I have to give up on my partner. I have to give up my home. I have to give up comfort for a while in this career that is burning me out. But also, it’s easy in the sense that I know what I’m doing. I’m comfortable. I’m familiar, I’ve got seven years of experience built up. It was a happy moment, but also just this, okay, stripping back to nothing. I have to give up a whole lot and take some steps back in order to get where I want to go.

Matt Bowles: Well, and it sounds like you were not really clear on what exactly your next step was going to be if you left all of those things, what you were then going to do. So, I’m curious in that moment, right, because I feel like a lot of folks maybe sometimes have that part of the feeling that you just described, and then they’re like, yeah, but I don’t know what else I would do, and that’s probably pretty scary and unknown, and the stuff that I have here isn’t really bad, like it’s okay, it’s kind of mediocre, it functions it works, maybe I’ll just stay with what I’m doing now and so forth.

And I feel like there’s a lot of people that might choose to make that decision. So, when you were in that moment, I’m curious if you can share a little bit about what the dynamics were, what the mindset was and the self-talk and maybe even any tips you’d give to somebody that might kind of be in that particular place in their life about making a bold move to make a major change.

Mashon Thomas: Yeah, it was terrifying, and I did not know what I was going to do, but I’ve talked to many people since and when they ask about the success that I’ve had since then, I do put it down to that moment of just being like, I’m going to do this and not so much worrying about the how, like the how we’ll come making that decision and then starting to take action toward it.

Alright, so, I flew back, and I had to have the conversation of like, we’ve been trying to work on things, but like, this is, I want to go in a completely different direction. Like, I want to go and travel the world and work remotely, and you want to stay here. That is a very clear, defining end to the relationship.

For me, it was also deciding to quit my job. And go back to school at that time. I thought only tech people worked remotely. So, I will go to a tech boot camp and learn coding skills. And I put down a 10,000 charge on my credit card with the hope of like, I’m going to pay this off by X amount of months because I’ll either have a developer job or some kind of new job, right?

It was all scary, but I had to make bold changes. And the important thing I think for anyone listening to now is that it doesn’t ever feel great at the time. Like, you know, the movie montage of like when someone’s cleaning up their life and they’re just like doing all these things and there’s great music playing.

It’s not like that. It sucks and it’s terrifying like every night. What am I doing? What am I doing? Especially like you said because if they’ve got a situation that’s fine or it’s okay. I knew that telling my friends and family was going to be weird because they would look at my life and go, what are you talking about? It’s fine. And that’s the thing a lot of people are okay with fine. My ex, he is to this day, a great person and people couldn’t understand giving up a great person in a great situation in order to chase something that you just intrinsically inside know you were meant for. So, it is very difficult.

Matt Bowles: Can you talk then about your path from going through the coding bootcamp and all of that to becoming the fully remote six-figure freelancer world traveler that you are today?

Mashon Thomas: Yeah, it took some time for sure. I’d say the next two years from 2015 to 2017, were extremely rocky. I moved to the other coast. I was living in Naples, Florida at the time and teaching there. So, I moved to Fort Lauderdale and went to the coding boot camp. It was like a nine-week camp. I learned an amazing amount. It was incredible, I think, to throw yourself into something as an adult that is brand new, scary, awful, terrifying, but at the same time, you’re around other people who are going through it as well. And you’re learning something in an incredibly compacted amount of time. A friend of mine had a job, she was one of the people I’d met through the coding bootcamp. She had a job and got me in at a startup as a technical writer. Again, no experience. It was really cool, because I was making the user manuals for new apps that the company was developing.

So, like step by step screenshotting stuff and explaining stuff. I’m sitting in on developer meetings that I have no idea what’s going on, but I’m furiously taking amazing notes and like scribbling down the scribbles that they’re doing and then typing it up and presenting after. And that was a really key experience for me because I learned it’s kind of a pattern in my life but say yes to stuff and then figure it out later.

And that’s something that I get asked all the time by people. How do you have confidence or how do you fake it till you make it? And for me, it’s all about saying yes and then having the confidence in yourself that you know you will figure it out. So, for one example of that company, I’m sitting in a meeting, and this woman just turns to me and she’s just like, you’re the tech writer, right?  And I’m like, yeah. Shaking my head, yes. And she’s like, you know how to use Microsoft Visio, right? Cool, great. Let’s talk on Monday. I have a lot of work for you.

I had never heard of Microsoft Visio in my life, but it’s like flow charting, diagramming, and all kinds of cool stuff. So, my weekend was sitting at home and doing like 12 hours of Microsoft Visio study, so that the yes that I gave her on Friday would be true on Monday.

So, I had a lot of experience in rolling with the punches and stuff there. So that company got a bit rocky. And again, I had just pitched them on, I see no reason why I can’t do my job remotely. I had gone to my boss, he’d gone to his boss, and they were like, yeah, we don’t see any problem with that. Well, we can have you start with a couple of days a week kind of thing.

And then, the head company came in and said, nobody works remotely. It was unrelated to my proposal. They just switched up a whole bunch of stuff in the company. And I was really defeated at that point. So, I called my dad and told him how miserable I was and how I just wasn’t seeming to be able to find this traction in getting to work remotely anywhere.

And my dad is the king of responsibility, right? Like he’s always about like, have a next job lined up before you quit a job, get your ducks in a row, get your shit together before you go making any rash decisions. So, I was not expecting him to say, you know, well, if you hate it that much, and if it’s not helping you get where you need to be, just quit.

We’re always here. Your mom and I can come to my home if you need to. It was more of that, like, sometimes you got to chase your dream spirit. I’m like, dad, I’m not expecting to hear this from you. So, within three days, I had given notice that I was driving a little 2008 yellow Toyota Yaris hatchback. Packed that up, and I had all my things in it, and I drove back to Ohio.

Boom. Okay. And, not ideal, right? I’m 30, maybe 31 by that point. I’m moved back in with my parents, which I never thought would happen. I’m back in Ohio, where it all started, where I’ve been trying to get away from. And I’m just like, wow, this is not where I pictured my life at this time. But so, I thought, okay, I’ve got rent free, mom and dad are great. I’m going to throw myself fully into looking for remote jobs. And that’s all I did, scouring the internet. And eventually I landed a job with a, online blogger working as a copy editor, small company, about 60 people. They told me when I got the job, I went through three rounds of interviews.

They told me that I had beaten out 336 other candidates. And I’m like, damn, wow. But like the effort that I put in, and this is something I teach in freelancing as well. The effort that I put into something; I think it’s unmatched. Like, when I go after something that I want, I’m willing to do the hard work.

The test project that they gave, the interviews like I was approaching this because it was like, this is my dream. I want to work for a remote company. I want to be able to travel freely. Absolutely. I’m willing to put in that hard work. I see that some people aren’t able to do that sometimes, but I feel stuck in what I can offer them.

Cause I’m like, my secret sauce is hard work. Like, it’s wanting to be really good at something. So, that company lasted for 10 months. I was feeling good, although it was lower pay than even teaching. I thought I’m smart, I’ll work my way up in the company, I’ve got this. And one day suddenly just chopped, they laid off 30 percent of the company.

And I was just blindsided on a Friday. And it was like, okay, I’ve done the nine to five, I’ve done the remote nine to five, and as it turns out, I’m still at the risk of someone else. I’m still at the mercy of someone else. And I got pissed off. I got really pissed off. I got really angry. And I was like, I am determined to make this layoff the best thing that has ever happened to me, I need to somehow take my income into my own hands. And that was the catalyst for me jumping right into freelancing.

Matt Bowles: Well, I also, as you know, got fired from my job at age 30 and said, you know what, this is probably a sign that I should be making a massive life pivot at this moment. And it’s an opportunity, you know, because that job that I was at, maybe I wouldn’t have left that job if I didn’t get fired from my job. Maybe I’d still be there. Cause it was pretty good. It was pretty meaningful and so on and so forth. Just like we’re talking about everything else in life. Right? So, I’m like, you know what, I’m actually going to take this as a positive thing and a push in a different direction and then figure out exactly what you just said.

I sure don’t know how to build a business because I have no background in that, but I bet I could figure it out if I really put in a lot of effort in trying to learn and trying to work hard and trying to do that. And so that was my story as well. So, for you, can you talk a little bit about the freelancing business that you built and that you now run and what you are ultimately landed on as your niche specialty superpower and how you structured your company?

Mashon Thomas: Yeah. So, I like so many other people did not know what I was going to do in freelancing. And I think that’s important to bring up because a lot of people listening might think, okay, I know I want to do this or it sounds great, but I don’t have any skills that I can offer. And I want to point out that that was a huge thing for me.

I struggle with imposter syndrome almost daily. I have self-doubt, all the other things. I thought of myself as just a middle school teacher. So, I was busting my ass on anything that came my way, whether it was a 50 project or whatnot. Determined to give my all. So, I started out on a freelancing platform, like Upwork.

That was my main source of looking for work. But after a couple of weeks, maybe a month of doing that, I thought this isn’t smart because on Upwork you’re competing. It’s kind of like the job market, right? You’re applying for a job. I was like, I bet I could go straight to the source. What do I know? I’ve got this experience from here.

I’ve got this experience from here. Like I’m good at doing all kinds of stuff and I need somebody who kind of needs that. Let me look for people who are doing what my last company was doing. Small business owners, there are companies fully online, so there’s no office to go into. They are solving a problem for other people, either selling a product or service that’s online, like software as a service type thing or online courses, that sort of thing.

And let me go straight to them and see if I can offer a service. So, I targeted people who knew, kind of, were in the same space as my last company. It was just like, hey, you know, I used to work for so and so, and I’ve noticed your business is doing this, perhaps you could use some help with this, whatever.

In the beginning, I advocate using everything you’ve got. Name drop if you’ve got names. You know, connect, you know, who you are to someone else that they may know in the same space. Like, do whatever you can to get your foot in the door. So, once I got my foot in the door with a few of these people, they said, okay, yeah, what can you do?

And I said, let me hear from you. You know, like what do you need kind of thing? What are you struggling with? I let people tell me what they were struggling with. And then again, just like that Microsoft Visio example, I went back and tried to figure out what I could do that would help them. One of my earliest clients, he said, I am just stressed out all the time.

He’s like, the business is good. Like business is taking off. Like we’ve got sales coming in. There’s so much money coming in. But everyday people on his team, he had about six people on the team at the time, people are slacking me. They’re sending me messages. They’re sending me emails. Like, everyone’s got a problem all the time.

There are constant fires. Which, running a business, that’s pretty much what it looks like a lot of the time. He’s just like, I need kind of like a right-hand person who can just jump in and figure it out. And I said, yeah, sure. I’ll do that. I had no idea what it was, but that’s how it got started for me. And that’s how I kind of found my niche to where I am now, which is operations management.

So, it started with me saying, yes, it’s so funny. He was probably the best client to learn from because he took it literally when he said, I need somebody who just figured it out. And I said, yes, he just started dumping anything that came his way that he didn’t want to deal with, he gave it to me. And I figured it out, Google, YouTube, wherever I needed to go, or just like streamlining everything and getting him on a call and saying, all right, you sent me these 27 things with no context.

What is this? You know? And it turns out I loved it. Turns out that my ‘just a middle school teacher skill’ worked out really well because wrangling a classroom of middle schoolers can be actually harder work than wrangling entrepreneurs and getting them to make progress.

Entrepreneurs are very much, you know, idea people. I’m the same way myself. So, I have someone on my team now that her job is kind of wrangling me. So yeah, it worked out very well, but it was an accidental trial and error thing. And that’s something I would advocate for people listening to start trying things.

I don’t know a single person ever. Who’s just walked right in and been like, yep, I just tried this one thing, and it was perfect. And you know, try a few things and see where you fit. See what feels good.

Matt Bowles: Well, one of the things that I really like that you have done is you have carved out a particular specialty area such that you now primarily works very specifically with business owners that have zero to four people on their staff and you do the operations management, help them to build systems, help them to build processes with the intent of scaling their company up.

Up to about 25 to 30 people, at which point they then need someone else to be involved and take them to the next level. So, you have this very specific niche about businesses that are in this particular stage and helping them with a very specific set of skills and deliverables to get to this next stage.

And so, you know exactly who your ideal target client and market is, exactly what you can do for them. And then now you have a portfolio of testimonials and experiences that you can show them. And I think that’s actually a really important thing because I think sometimes people start freelancing, they might be like, yeah, I’ll take anything. I can do all of it. I can do anything. I can do whatever you want me to do. And then you’re not an expert or a specialist in anything.

And where you eventually landed, I think is really important, because if I’m the owner of a business that has zero to four people, I don’t want to hire somebody that says, oh yeah, I could do anything. And I work with everybody. I want to hire somebody that says I work only with businesses that have zero to four staff, and I will help them to get to this place. And that’s a hundred percent of my specialty. And I’d be like, oh, that person is for me. So, I think that’s a really important piece of what you have done.

And actually, I want to see if I can ask you for advice because, in terms of listeners of this podcast, we have both freelancers and business owners and aspiring freelancers and aspiring business owners. So, I’m curious for the business owners that have zero to four staff people at the moment, and they would like to scale their company up to 25 staff people. What are some of the key pillars and strategies for how they should think about doing that efficiently?

Mashon Thomas: So, what I like to do with my clients is we first sit them down, the founder, the CEO, the business owner, we sit them down and we figure out what they must do because, you know, I’m a business owner myself, but we often think that we must do a lot more than we absolutely must, right?

There are key things that they should be doing. Everything else should be handed off. So, I try to work with them on, let’s get the must down and let’s get these other things handed away. They can be done. I fell into that trap as well. Like, well, nobody can do it as good as me. And I love showing my clients. No, no, no.

Actually, there are people that can do it as good as you and even better. They’ll come up with more efficient ways and things like that. But I kind of handhold and walk them through that experience. Even the most, let’s just say like, well, invoicing or something. And I’m like, look, we can systematize this.

I promise you we will sit down. We will learn exactly how you do it. We will train someone else in it. We will make sure that there’s feedback and guidance through the process. And then this is going to be a thing that you just no longer have to deal with. And that way, freeing up time, like they should be reading books. They should be in other businesses. Entrepreneur communities, they should be going to conferences, they should be learning more about the industry and their business and what’s changing, what’s happening. This is big picture thinking stuff, but most of the time they’re bogged down by all the small stuff.

And I love coming in and showing how it’s possible to just take that small stuff off. I love opening up their eyes to the amount of amazing freelance talent that’s available all over the world. You want a customer service team that’s on, you want tickets responded to within one hour? Cool. We’ll put together a 24 7 customer service.

Somebody on each shift in different countries around the world will have it covered. But they shouldn’t be dealing with the day-to-day stuff. They should be looped in on it and getting reports on it, but not actively managing that. So that’s what I come in and do. I show them how to either let someone like me manage it.

Although as time goes on, I do less and less of that. And usually, I’m training someone on their team. Like, let’s get you a long-term ongoing operations manager. But it’s really about just once we’ve identified what we can take off their plate, those teams just grow over time. It’s like if they’re answering their own customer service tickets, it’s like, cool, we’re going to get a person. We’re going to train them to do that and watch. Oh, wow. Look at this. Your business is growing and actually you’ve got more staff coming in. So, we’re going to take that and we’re just going to add a second person to that customer service team. We’re going to keep them going.

My original client, where I kind of found that I was good at this and all that kind of stuff, like we had one girl in customer service and now I think customer service is our biggest department, I think there’s about 12 to 13 people on that team right now. So, the reason at going back to what you’re saying at the beginning about my niche being so specific zero to four, right? Is because I love the chaos aspect of the early days.

When you get up to 25, 30 people and why I hand it off to other people after that is because it feels more for lack of a better word, corporate to me, like there are rules, everything is in place, things are kind of humming along and we have to go through checks and balances to make decisions and it just slows down for me a bit. I like that early stage where it’s just chaotic, anything goes, right, we’re going to hire, train and get this person going in 24 hours, go, you know, I’ve done that before, where it’s exciting.

We don’t have a rule book. Cool. We’re going to make it up as we go. Everybody throws things in as you think of them. And then we’ll have a meeting next week. We’re going to finalize; we’re going to structure all this. And this is our new set of operating procedures for how to deal with customer concerns. You know, it’s so much fun.

Matt Bowles: Well, I also, of course, want to ask for your advice for freelancers, for people that are maybe in the early stage of that journey. Maybe they’re thinking. Listening to this episode, thinking about quitting their job to build a freelance business so that they can be fully remote and travel the world.

Also, you have a pretty extraordinary value proposition that you are, have been in the past, able to train people how to work 20 hours a week, take three months off each year, and still make a 100,000 as a freelancer. Can you talk about what the steps are from quitting your job to building a business like that? That is financially viable and also gives you the time and location independence to travel the world.

Mashon Thomas: That’s just math is how I present it to my listeners, like on the podcast and stuff. So that’s a matter of math. If you work backward from there, through all the steps, you come out to that being $125 an hour.

You need to be able to make $125 an hour in order to achieve that 20 hour a week, 40 weeks a year, you know, which is the 12 weeks off. And so, then it’s a matter of going, okay, what can I do that would earn me $125 an hour? And this part is so important and it’s kind of why I Speak so much in the podcast, try to get on other people’s podcasts to spread the word, because there are actually so many things that you can do to make that kind of money, which I never thought possible back in the day.

You know, I thought anyone making a hundred dollars an hour had to be like a doctor, a lawyer, you know, turns out business owners will pay a lot of money for things that make them more money. So, I advocate people if they don’t have a skill in mind already, think about what you can do that is going to be useful and it’s going to help that business owner generate more money.

I’m a business owner myself. I will pay you $2,000 tomorrow if it’s going to help me make $10,000. What I do operations wise, for example, I am helping the business owner make more money because if I can take them from zero to four people to 25 to 30 people, we are growing the business. We’re not like overextending and bringing on more people than we need.

We’re doing this in a consistent manner because the business is bringing in more money. And as we add more people, it grows. The other thing that I find really helpful about these types of positions, advertising operations, get in with the clients and you make it a long-term ongoing thing, thereby reducing instability.

I talk to a lot of freelancers who go from job to job or client to client, and that’s never been the case for me. I’m with people for a long amount of time because with these things, the more you get to know about the client, the better you can do your job. And the more the client relies on you, the more you rely on each other.

It is a relationship that functions really well. You know, people are moving fast. People want things that are different. They don’t need the old school. You’ve got six degrees, you know, whatever. They just focused on what you can do. How soon can you start? How soon can we get results going? And it’s a very business to business relationship, not just I’m your boss and you’re my employee do what I say.

Matt Bowles: Totally agree with that. Mashon, I also have to ask you about your digital nomad life and how you have designed your lifestyle once you figured out how to finance it and to create the location independence to travel the world. I think I want to start in South America. You have spent years Slow traveling through South America through some of my very favorite countries from Colombia to Peru, to Ecuador, to Argentina.

Can you share a little bit, maybe let’s just start with Colombia, I know you’ve spent a lot of time in Medellin. We both have a lot of love for that city. I’ve spent multiple months there. I’ve been back a couple different times. Can you share a little bit about yourself? What were some of the highlights of Colombia?

Mashon Thomas: Oh, wow, Columbia was magical. I think because it was my first stop when I left the U.S. that was my one-way ticket experience. Just, boom, Las Vegas to Medellín. Yeah, it was amazing. I chose South America and Medellín specifically because I wanted to learn Spanish, really just immerse myself. And I had read online that not a lot of people spoke English.

So, it would be using it from sunup to sundown. I got enrolled in a Spanish school right away. I was spending 20 hours a week in Spanish school, 20 hours a week doing client work, just doing day trips all over from Medellin, exploring the city. At that time, I was traveling with my cat. So, I had my cat for many years and had to figure out all the paperwork and everything to go with her because I was not about to leave her behind.

But yeah, because of her, I didn’t want to go too far away. So, I have a lot of Columbia still to explore, but yeah, I was just floored. Honestly, it was getting to know a new city again, getting to meet new people. It was a magical time because of the Spanish school, all the activities that they had going on. You just met people. In fact, one of the activities at my Spanish school was how I met the friend whose wedding I went to last week. So, it’s just all of these little moments that tie together.

It was an incredible experience. I love Medellin and it was nice to go somewhere because you will have this, I’m sure in all your travels, but people who have never been to a place will tell you about the place. And why it’s so scary, why it’s so dangerous, why you shouldn’t go. And I went and had an absolutely wonderful experience.

Matt Bowles: Well, I know you’ve also spent a bunch of time in Peru. Can you talk about your experience there? And for people that have never been, what were some of the highlights that really stuck out to you there?

Mashon Thomas: So, Peru, yeah, obviously Machu Picchu is going to be the big one. A lot of people go for that. I was based in Lima for several months. and made the trip up to Cusco and then Machu Picchu. And I actually would love to give your audience the best tip that someone ever gave me about visiting Machu Picchu, which was to go twice. And I’m so glad that I did this. And what she meant by that is you can take a train. It’s about a four-hour train ride into Machu Picchu. If you leave in the morning from Cusco, you take the train, you go to Machu Picchu in the afternoon, and then you stay the night because there’s not really enough time to make the evening train out.

So instead of just staying the night, getting out, and taking the morning train out again, the next morning, which a lot of people do, I bought two tickets. So, I went to Machu Picchu the afternoon of the first day, and then again, the morning of the second day, and then took the afternoon train out. And what my friend had said, she said, do this because she’s like, first of all, most people go to Machu Picchu once in their lifetime. What if it’s cloudy? What if it’s all foggy and you can’t see anything and you can’t get the whole, you know, full Machu Picchu experience?

And I’m really glad that she told me that because we both experienced things, my friend and I. We had sunny blue skies, an incredible experience the first day. We did the whole tour going all through and everything.  And then the second day we came back, and it was foggy and misty and really cool, these amazing clouds, just like parting to see Machu Picchu. But we didn’t feel rushed. We didn’t feel like we had to do the tour again or anything. So, we just found this little spot. We had food and snacks and we’re just sitting there having amazing conversations about life, but just like Machu Picchu at our feet, like, this is incredible. This is wonderful.

So, I encourage people to do that. It was the standout experience of mine. But I had a five-day experience as well with a company called Peru Hop. So, they have like Ecuador Hop, Peru Hop, Bolivia Hop, and this is my first time trying it. So, it was a bus tour, we left Lima, and I think we spent four days going around hitting some of the major spots.

I went to Huacachina, the oasis in the desert there. I did sandboarding and dune buggying, which was terrifying. I think I’ve had enough of like the dune buggies. I think I’m too settled now; you know, I used to be much more risk tolerant. Now I’m just like, oh my gosh, the waivers on this thing, my health insurance, you know, getting old, but that was amazing.

We went to Paracas by the coast and that was lovely. I flew over the Nazca lines in Peru. That was my first time in one of those teeny tiny little airplanes. Did not love that, but it was one of those things.

Matt Bowles: Well, you also ended up spending a whole bunch of time in Ecuador. Can you talk about your experience in Ecuador?

Mashon Thomas: Someone I’d met in Medellin was going to Quito and when I was in Peru, so I did not know this about Lima beforehand, but in the winter months, it is very gray. Like just this blanket of gray descends over the city and just hangs out for months. I never knew before that I needed to Google, does this place have sunshine? But now I do because of that experience. I saw the sun four times in Lima in three months. And that was awful for me, you know? So, when my friend said, hey, I’m going to Quito for a couple months. You want to come hang out? I said, is the sun shining? I was like, all right, I’ll come. So went to Quito.

Quito is at 10,000 feet, roughly elevation wise. So, it is high, but I acclimated pretty well over time. Quito is a beautiful city. Beautiful city. You’ve got this historic central part. You’ve got the more urban downtown, La Carolina area. They’ve got this huge, beautiful park. That’s kind of like a New York central park kind of thing. And then all these modern buildings, skyscrapers around it, lots of cafes, things to do, trendy restaurants. It’s very cool.

And I found the accent very easy for me to understand with my mixture of Colombian, Peruvian, Spanish. So, I went to Quito expecting to stay for 90 days. Loved it really quickly. Just did my renewal for another 90 days. That was pretty easy to do. And I was preparing to go and ask to do another six months when the pandemic hit. So, I hunkered down.

Matt Bowles: Well, after Ecuador, I know you then spent some time in Argentina, and I want to ask you about that because Buenos Aires has a very special place in my travel journey. It was my very first nomad destination. After I got rid of all my stuff, and left L.A., I went to Buenos Aires, and I spent about three months there as my first stop.  So, I have a lot of love for BA, and it has a really important place in my travel journey, but I’m curious for you, what was Argentina like? What were some of the highlights there?

Mashon Thomas: Whoa, Argentina. What an incredible place. It’s huge. I did not realize how big Argentina was until I traveled the length of it.

In Buenos Aires, I spent around six weeks total. I got there and used it as just a settling in point. My friend was meeting up with me. The reason we ended up in Argentina actually was because I had a trip booked pre-pandemic, but it kept getting delayed, but it was worth it.

She and I booked a trip to Antarctica. And so, the South and tip of Argentina is one of the jumping-off points. There’s another one in Chile but I settled in Buenos Aires for a week or two and met up with her. We flew all the way down to Ushuaia. We went to Antarctica, a 10-day trip, mind blown, just absolutely spectacular. All the penguins, all the icebergs.

Matt Bowles: What was that like? I mean, for people that want to understand what’s involved in getting to Antarctica and then what you see when you get there, I’ve not done it. What was it like?

Mashon Thomas: Yeah, it was mind boggling. We booked through a tour company. You can’t just go on your own. You go through a tour company. We flew in, we flew down to Ushuaia and met up with them. They put us up in a hotel for the first night. And then it was like, all right, everybody went through, and we were heading out to the boat. So, we sail out, we have two and a half days to cross the Drake passage, which is I think the most dangerous in the world. Very rough seas, very seasick. I was not prepared. You know, people were asking, do you get seasick? And I’m like, I don’t know. I’ve not been on that many boats in rough water. The crew though. Incredible. They had an onboard doctor. Incredible. Got the little seasickness patches all hooked up.

So, I was much better on the return trip, but it was funny talking to one of the crew. You know, we asked him like, how bad was that crossing? He’s like, it was like a three out of ten. Oh my god, I can’t imagine what a six is like, what an eight is like, oof. So, very big thanks to the crew for keeping us safe because you have to, they told us over and over before, this is going to be a flexible trip.

We don’t know our itinerary exactly because it all depends on the weather. So, once we got there, they took you by zodiac back and forth. You stay on the boat, they would prepare, you know, I have a morning excursion and evening when you go in, ice, penguins, these incredible just like mountains of ice. We saw seals, whales, so many different types of seabirds and stuff.

Sometimes I look back at my pictures and I’m like, I can’t even believe that that happened because it was so surreal, but they did an amazing job of organizing everything. I paid extra for this excursion where you could camp overnight. So, we stayed in these sleeping bags and I’m not a camper, but my friend wanted to do it.  And I was like, sure, I’ll go with you. I mean, if all the places to camp, it ended up being this crazy wild night with some weather moving in. And we all had some amazing, fun stories to tell about the next day. Not my favorite thing in the world, but I am glad that I did it. We also got to do the polar plunge, which is jumping into the freezing water there.

And that was a lot of fun. They offer 21-day trips. And I would love to go back and do that someday as well because you get to see more of it. And it’s just, honestly, talking about one of those places that makes you feel small in the world.

Matt Bowles: Well, one more place that I want to ask you about that I have been to briefly and really impacted me, but you’ve spent a lot more time there is Montenegro.

I have been to the Bay of Kotor and one of my fondest travel memories or moments was swimming in the Bay of Kotor and then looking up while swimming in the water and just seeing all of these incredible mountains surrounding you. And I can just remember thinking, this is unbelievably gorgeous. I am so appreciative of this moment. I can’t really believe that I’m here right now and this is happening. But wow. And I was just soaking it all in. And years later, I still remember that exact moment. And you have spent a whole bunch more time than I have in Montenegro. For people that have never been, what did you think of Montenegro? What was it like?

Mashon Thomas: Montenegro is amazing. I know exactly the view you’re talking about because I just spent three months living right on the Bay of Kotor with that view that you’re talking about, and it was incredibly hard to leave. But the people I found so friendly and welcoming, just, I love going to places in shoulder season.

So, I was there, you know, not during the busy, busy tourist season and got to just feel like I settled in a little bit more, talking to the locals. Made some friends really quickly. You can get to see the same people over and over the old town. It’s very small. So just like walking through and, oh, I bought something in that shop the other day, and now the shop owner says hi to me, you know, for the rest of the time that I’m here, but just, it’s a spectacular place.

I think it’s going to become more popular in the coming years as more and more people. You know, there are a lot of Europeans there. I didn’t meet that many Americans there, but I think it will continue to jump up in the destination place. But I mean, it’s just incredible, you’ve got the entire coast. You’ve got Kotor, you’ve got Budva, Ulsinj all the way down at the bottom.

I don’t know if I’m pronouncing all of these correctly, but then you go inland, and you’ve got incredible mountains. You’ve got national parks. My friend and I drove up the one weekend and we actually got stopped by the snow. There was still quite a bit of snow. So, we’re like, all right, this is as far as we go in our little car, turn around and come back, but just, it’s a beautiful place. And it’s so small. I love going to a country that’s small enough that I feel like I can really kind of jump around and see quite a few parts of it.

Matt Bowles: I want to ask for your reflections and tips on thriving in the digital nomad lifestyle. You’ve been doing this now for eight years or so. Can you just share a little bit about how you structure your travels and design your lifestyle and some tips you might have for sustaining this lifestyle over the long term in a way that remains exciting and joyful.

Mashon Thomas: Yeah, there are a lot of challenges, and I do think it’s important to talk about them. Sometimes it can seem like people are just selling the good aspects, but there are some difficulties. Finding community is one of them being connected to other groups of people doing the same thing, because when you’re picking up and moving every so often it can get exhausting just starting over.

I also can fall into the trap sometimes of being too at home. I’m an introvert by nature, and so sometimes I’ll just go to a place and just like not connect with people and kind of miss out on more of the authentic experiences that I would have because I’m just like, I’m just done. I’m in my apartment this month. I’m not really doing anything.

So, I balance that with looking for meetups and events, trying to make sure that I get out, but also knowing myself and what I need. You know, I need four to five nights at home a week to have a good week. You know, I can’t be out too much more often than that, or I just will get completely drained.

I’ve struggled over the years with working too much or working not enough. That’s a constant thing. You know, if I’m really dialed in and I’m loving what I do, I tend to overwork without even noticing it. So, I’ve had different things that I’ve tried over the years, like setting very strict alarms on my phone in another room to make me like get up and go like, okay, now I got to hit the snooze.

And then I got to come back and now I’ve got to wrap everything up and then stick to that. But it is hard. You know, I’ve talked with friends about this. When there’s no one else around you to see what you’re doing, you can live in some really bad habits, especially like I’ll fall down this ADHD kind of rabbit hole of one more minute, you know, five more minutes and then five hours have gone by and I’m like, okay,  yes, did I get a lot done?. But it’s midnight and now screwed up how I wanted my day to go tomorrow.

So, putting little checks and balances in place something I found that’s really helpful for me is time blocking, so setting alarms on my phone for specific amounts of time to work on different things and having a little 15 minute reminder before that’s up in order to stop, wrap up, start taking my notes on where to start the next day so I can come back to something fresh.

I also try to sort out my life into different, like on my computer I have little, different user accounts. So, it’s like, okay, this is the user account for this client. This is the user account for my business. This is the user account for personal time, and I have one for like leisure time. So, I log into the different user accounts because that’s got all my settings saved.

And I know that if I’m not working, I’m logged into my personal account on my Mac, then no Slack messages are going to be popping up. No one can get ahold of me, and I can truly respect my time there. As far as designing my lifestyle today, so you’re catching me actually, this is funny. This is, I’m trying to learn how to go with the flow a little bit more.

Previously, I was very much into slow travel. So, I would go somewhere and the minimum I was usually staying was three months. So, using up the full 90 days, sometimes renewing to get six months if it was pretty easy in a place. And that allowed me to travel the way I like to do so, which everyone’s got to find out for them.

But for me, going to a place, settling down, getting to know people, having a coffee shop, having a grocery store, seeing the same people, recognizing them, getting into a real rhythm in a place. And now, just since coming over here for my friend’s wedding last week, I’m doing a lot more of like, I don’t know where I’m going, or I don’t know what I’m going to do next.

Granted, this is five, six years into my business now, so things are a lot more stable, and my team knows how to do things. Like, we’re doing this 12-hour time difference work, which is new. So, I do have a little bit more of that flexibility now. But it’s also new for me. My friend at the wedding said, Okay, so what’s your plan for the next six months? Where are you going to be? Because I got to know where to visit you. And I was like, for the first time, like I have no plan.

I think I’m going to Australia after this. That’s what I’ve been telling people. That’s kind of like a loose plan, but I have nothing booked. Honestly, the next two weeks of my life are booked.  And after that, It’s all up in the air. So, learning how to be a little more comfortable with just kind of really doing the flow thing.

Matt Bowles: Mashon, reflecting back on all of your travels, how do you think that all of these travels have impacted you as a person?

Mashon Thomas: That’s a great question. And something I think about a lot. One of the biggest ways is that it has shown me how small a place I occupy in the world. In a really good way. Like sometimes when I’m having a bad day or I am just all stressed out about something, I will give myself a little dude, chill out. First of all, almost no one gives a shit. Almost no one knows you exist in the grand scheme of all the things going on in the world. This is not a problem. You are making it a problem. You take up such a tiny space.

That’s not to say I’m not worth anything, you know, but it’s like breath, relax. The second thing that I have found really great, learning how other people live, has shown me how good I had it as a kid. And I would not have known that without going out to see the world.

I still hear, sometimes, complaints, not to say that, you know, we can’t want improvements or can’t want things to be different, but when I think about some of the things I used to complain about as a bitchy teenager.  Or even some of the things I have gone through with therapy over the last few years, just about my childhood and different things about the way I was raised. And then I’ve been traveling and I’m like, okay, you can still have your issues with that, and you can still have that, but it helps me to view it in a much more calm and positive way in the sense of, okay, I would have liked some things to be different. But wow, look at this person over here and look at what they’ve had to go through, what they’ve had to experience.

I am so much more grateful for the things that I had in my past and have now today. It’s taught me a lot of perspectives. And the last thing I think that’s huge is just that people are virtually the same everywhere. Like, we all want the same basic things. You know, we want to have friends and family around that love us. We want connection. We want to be able to wake up and do things that make us happy and just spend time with people we love and do things we love all over the world. That is a common thing that unites us. That and smiling. Smiling is universal.

Matt Bowles: You have been doing this now for over six years. Can you reflect on and share why you are so passionate about travelling and continuing this lifestyle? What does travel mean to you today?

Mashon Thomas: You know, it’s just an intrinsic part of my life. It just feels like me. And I was reflecting on this a bit ago, and I’ve had some conversation with friends recently on, I don’t know how to stop traveling if I want it to. And you’ve been doing it for longer than I have.

So, I’m sure you’ve kind of had these ebbs and flows over the years. But like, every time I think about settling down, I don’t even know where to begin. I recognize that there was a part of me in the past that used to live a sedentary life in one place, but now I’m like, I don’t think I know how to do that.

I feel like the first bad weather would come along and I’m like, you know what? I know a place in the tropics. I’m out of here. So, but yeah, no, it’s just, I feel the time may come where I put down at least a base, but I feel like I will always travel because for me, it is just It’s an inspiration, it’s a reset.

There’s something inside me that still needs to see more places and meet more people and learn about how they live their lives. And travel for me is very connected with the people that I meet in these places. If it was just going to a place, not speaking to anyone, not having anyone with me, that wouldn’t be the same thing. But it’s always about those people that you meet along the way.

Matt Bowles: Well, Mashon, I think that is a great place to end the main portion of this interview. And at this point, are you ready to move into the lightning round?

Mashon Thomas: Yeah, let’s do it.

Matt Bowles: Let’s do it.

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

Mashon Thomas: So, this book is called The Course of Love. It’s by Alain de Botton and I found it a couple of years ago in a charity shop in the UK for a dollar or a pound and it’s just an incredible look at relationships. I read it and I was thinking, oh my gosh, if I had had this when I was younger, you know, as we do so many times. But it’s a novel. But it’s written with so much philosophy thrown into showing the course of how we meet somebody and then just go through all the stages of a relationship, and it’s written in such an engaging way. I immediately gave it to a bunch of friends, and I just think that anyone getting into a relationship anyone in a relationship, you know, it’s an incredible read.

Matt Bowles: All right, if you could have dinner with any one person that’s currently alive today, that you’ve never met. Just you and that person for an evening of dinner and conversation, who would you choose?

Mashon Thomas: All right, so a lot of people find this funny, but for me, it is Dwayne Johnson (The Rock). Now, I have no wrestling, I’ve never watched wrestling or anything, but I am fascinated by his ability to transition between the career that he’s made for himself, also the businesses he has for himself, and his charisma.

And the way that he gets along with people. Um, I think it was Oprah who said about him once, most people have the ‘look at me’ gene, but he has the ‘I see you’ gene. So, if I sat down with him, I would want to talk about two things. That, his charisma and how to develop that more because as an introvert, it is something I struggle with. But then also from an operational standpoint, I would just want to know so much about logistics and his team and how he manages so much with so little time.

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

Mashon Thomas: So, I am very forgetful at times. So, what I’ve done when I’m planning trips, I have a travel note template that I use over and over.

So, this reminds me of all the steps that I need to take from booking to actually getting there and checking into my hotel, Airbnb, you know, I’m all about systems. So, it has all the checklists. It helps me plan out, you know, where I’m going, how am I getting from my place to the airport? Then at the airport, what’s happening?

Then the airport lounges what’s happening and just step by step all the way through. And it’s something that I just made. And now I can just duplicate that for each new trip and fill out the necessary parts because otherwise I will forget and I’ll be on a plane and I’ll be like, I forgot to check what currency they use there. I don’t even know what the exchange rate is.

Matt Bowles: All right, Mashon, 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 Mashon?

Mashon Thomas: Woo. So, I would tell her, look, a lot of people are going to give you advice over the years. Take what you can, and definitely learn from other people’s mistakes, but don’t forget to listen to your gut. If you want something, you have this driving internal thing that you want to go for, go for it. A lot of people who tell you that you can’t are people who haven’t done it themselves.

But stick with your gut and go for it. Also, I would say, you’re never going to be ready, so just start today.

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

Mashon Thomas: Okay, so Iceland. Love Iceland. I’ve been multiple times, and I will continue to return because it’s just one of my happy places.

Montenegro, we just talked about it. It is stunning. Kotor especially, just that bay area. I used to think I was an ocean girl, but the lake and mountains. It’s an incredible combo.

And also, Albania, so, just below Montenegro. I went last year for the first time in a week, and it was just incredible. Again, they’ve got the coastline inside the country. There are spectacular small towns and UNESCO world heritage sites. Amazing things to see. The people are so friendly and the food. Oh my gosh. The food we just ate and drank wine for a week. My friends and I, and it was, it was absolutely incredible.

Matt Bowles: That’s amazing. Albania is so high on my list.

All right, Mashon, what are your top three bucket list destinations, places you have not yet been? The highest on your list, you’d most love to see.

Mashon Thomas: Yeah, honestly, I can’t believe I haven’t been to these places yet, but Greece, I’ve not made it to Greece in all this time and definitely want to go. Of course, want to go to Santorini and Athens, but also just travel around. I would love to do like three months in Greece to really just like settle in. And have a base there and then head out and visit some other parts all over the country.

Next up is Georgia, the country, because I say that a lot, not to be confused with the state of Georgia. But yeah, I have again, heard wonderful things from people who have been there about just, the country, the friendliness, the food and wine, and just the fact that it’s kind of off of a lot of people’s radars, so you can still have some really cool experiences there.

And New Zealand, New Zealand, because New Zealand, Australia would be my last continent, and I plan to go to Australia as well, but I think New Zealand is less scary wildlife wise. So, I’m really looking forward to spending some time in New Zealand.

Matt Bowles: Awesome. Alright, Mashon, at this point, I want you to talk a little bit about what you are up to, what you’re doing with Live Work Travel, both the blog and the podcast, and also talk about how you work with freelancers or aspiring freelancers, and then how people can find you, follow you on social media. How do you want people to come into your world?

Mashon Thomas: Yeah, definitely. Thank you. Yeah. The Live Work Travel podcast comes out every Monday. So, these are smaller bite sized episodes, just tips that I have gleaned over the years around mental health and living as a digital nomad. Freelance tips, finding clients, things like that. And of course, lots of travel tips.

This is my offering to people just because I can’t stay quiet about this lifestyle and just really want to educate people. I also recently have started an online community. And that brings together people who want to be supported in their journey and this lifestyle. So, aspiring digital nomads, aspiring freelancers, and even people who are already on their journey who just want to meet others like them and be supported.

So, I found that the beauty of a community was bringing together the types of people that I’ve met all over the world kind of into one place and doing what we can to support each other because so many people, you know, whenever you’re starting out, you have the same questions as somebody else. And I like the community aspect because it’s very personalized.

Like people can just ask me questions and I’m like, cool. Yeah, I’ll do a quick little training on this. And it not only helps that person, but it helps everyone else who’s a part of the community as well. So, the podcast is available on Spotify and Apple. And the online community, you can Join Here, and I also have one for people who prefer like just the linear A to Z, I have a freelancing course that takes everything I learned in my first year of going from no experience to almost making 100k that first year. That course is called the Escape Hatch and that’s Available Here.

Matt Bowles: All right. We are going to link all of that up in the show notes. So, you can just go to the show notes for this episode. There you are going to find direct links to everything we have talked about in this episode, including all of the ways to find, follow and come into Mashon’s world.

I am a big fan of your podcast. I think it is very substantive, and I also am very impressed with the consistency of your publication. So, this is a serious podcast that you have really committed to over the long-term folks. So, I would highly recommend checking it out wherever you are listening to this podcast. Once this episode is over, just type in Live Work Travel and you can subscribe to Mashon’s podcast, check it out. Please leave her a rating and review as well. She’s doing amazing work. And Mashon, thank you so much for coming to the show. This was amazing.

Mashon Thomas: Matt, honestly, I wish we had more time because this has been so much fun. Honestly, thank you so much. You’ve done just an amazing job of asking wonderful questions. It’s just kind of led me along into telling my story. It’s been effortless and I’ve just loved every minute.

Matt Bowles: Well, I think you are amazing. We’re going to link up everything in the show notes so people can come into your world and get a whole lot more of you. And thank you everybody for joining us and good night.