Club Freedom® presents Freedom Lifestyle: Remote Work, Making Money on the Move, with Remote Work Expert Kathleen Hamilton & Freedom Lifestyle Entrepreneur Clinton Young.  Listen to Kathleen’s podcast and join her community to access her freebie content on her website in the show notes below!

Be sure to join Clinton & Mayumi on their journey to a lifestyle filled with freedom, fun, and adventure by following them on Instagram and Facebook @ClubFreedomLive. Also join their Facebook group for a more in depth look into their journey at 

“Remote Work, Making Money on the Move”, with Remote Work Expert Kathleen Hamilton 

by Clinton Young – Freedom Lifestyle Entrepreneur 

Clinton Young: I’m so happy to have you on today and to be able to have a conversation with you about your journey and what’s exciting you, and what’s been challenging?

Kathleen Hamilton: Amazing. It’s such an honor to have been invited. Thank you for reaching out. I really appreciate it.

Clinton Young: My pleasure. You are one of the first people I thought of. And then when I saw your podcast, I was like, wow, that’s a cool podcast. And then I started to look around and see what you’re up to, and realized that although you’re always all over the world somewhere, you are actually looking to settle for a time in Portugal.

Kathleen Hamilton: Yeah, it’s a really interesting time for all of us travelers. I’ve actually seen quite a few people in my network who have been looking at settling. And I think there’s this interesting situation that happens when you’re creating your life around so much travel, you voluntarily create uncertainty because you want experiences that push you outside of your comfort zone. But when so much of the world is in uncertainty, all the time, it can become very energetically challenging to balance the uncertainty that you want to create to push yourself out of your comfort zone. And then the uncertainty that just exists in the world right now. So I think creating some certainty to just ground us is something quite a few of us now are looking to do.

Clinton Young: Wow, that that was a great little sound right there.

I’m really excited to hear just what’s going on in your world, even if it’s just regular, you know, living in Portugal, that’s kind of amazing. Especially for the people that follow me. So just a little backstory, you probably know I’m a speaker, I’m an international keynote speaker so I speak all around the world, mostly in the US, but also a lot in the UK.

A lot of people ask me, what do you speak about? Well, do you know how some people are going through life, and they may experience a failure or maybe a loss, and then it sort of creates this doubt or this fear.

Clinton Young: Then in the future, when they’re either up for an opportunity or they want to start a business or they think they can do something, but they don’t really have the belief in themselves. You can probably relate. We can all relate to that on some level.

So what I do and what my speech does in my programs is really enable that confidence and the courage to overcome that fear, and overcome that failure to really live your dream life right now. 

Clinton Young: Hence, having conversations with someone like you, who is from the outside looking in, you are already living your dream life and you’re continuing to create that. Now obviously not everyone that follows me loves to travel. But this is sort of a passion project for me because I teach this stuff.

And this is my future dream life which is doing things like you are doing. You’re living in Portugal or traveling all over the world, hanging out in Africa, every other month. know, are all over the world.

Clinton Young: My wife and I are thinking about renting out the house next year. It’s, it’s going to happen. And we’re going to start with an RV tour around the US for six to twelve months. And then we’re just going to go international. So today’s conversation is all about that journey. 

Kathleen Hamilton: Amazing. 

Clinton Young: Okay, perfect. I would be doing myself a disservice if I didn’t also share the niche of people that I do work with, speakers. People that are either aspiring to become world class speakers, or entrepreneurs that want to grow their business through developing world class speaking abilities. 

Clinton Young: Okay, enough about me. The whole rest of this I want to be about you.

Kathleen Hamilton: That’s awesome context. Thank you for that.

Clinton Young: Okay, so let’s jump right in. Why don’t you just share a little bit about who you are, where you are right now, and what is it that you’re up to in the world? 

Kathleen Hamilton: Thanks Clinton for having me. I’m super excited to be here. So yeah, I have been a full time digital nomad for over 3 years and I’m in an interesting transition point right now and I’m sure we’ll get into that.

Kathleen Hamilton: I work remotely. I am the head of product for GeniusU, which is an online Entrepreneur Education Network.

And I also run a side project, which is the Purposeful Remote Work Community all about helping people actually transition into remote work that also makes a difference and an impact in the world in some way.

Because my belief around remote work and digital nomadism and having the privilege to do that myself is that whenever someone is working on a project or has a job that is related to their purpose and their impact in the world, they have a more positive, more fulfilling life, and I believe everyone has the ability to do that. It’s just we’re not really taught how to do that in school right and we’re not really taught how to do that in mainstream culture, either. But we’re seeing more and more of this. My mission is really to support people to get into work that gives them the freedom to have a life that they want to live, whatever that looks like.

Kathleen Hamilton: And so I get to do that through my side project and Ikigaia podcast. But for me, I also then have this amazing full time job, which I love, and which enables me to travel the world as well. So that’s what I’ve been doing over the last few years.

Clinton Young: That’s great. So you heard it here, folks. You can actually have a job and still have freedom and adventure in your life. There are actually companies out there that allow you to travel and live all around the world. 

Clinton Young: What would be your advice to anybody that has a job and maybe they don’t want to become an entrepreneur? What should they look for in a company culture or in a company? What are some of the qualities that they should look for in a company?

Kathleen Hamilton: I think what’s amazing about the times right now is; there’s actually more companies than ever, working remote. Even if you’re listening and you’re in a job right now, it’s very likely over the last few months you’ve had to work from home. Right? There’s a lot of jobs now that have had to move remote and now offices are starting to bring people back in. But if you’re in a job and you’re looking to work remotely, the first thing always is to have a conversation with your boss. Because there’s a possibility that if you’re in a job that you’re already enjoying and you wouldn’t mind doing it elsewhere, and you think you could do it elsewhere, it’s possible. Have that conversation with your manager who has to actually clear that. There’s so many amazing templates online now that you can use for those conversations.

Kathleen Hamilton: The second thing is if you’re looking for a company. I mean, for sure. I think the preconceived notion is that all the companies that allow you to work remote right now are in tech. That’s false. There are amazing companies that are not in tech. I’ve seen many types of remote jobs. Nonprofits have all sorts of work that’s remote. There’s all sorts of writing jobs, digital marketing. Yes there are a lot of tech opportunities, but there are also companies who are realizing that remote work cuts their costs and also increases their reach because if you’re able to work from anywhere in the world, then you’re able to bring the message of that company with you. So check out online job boards. There are freelancer boards. There are lots of job boards, just do some research, check out LinkedIn. They actually have a remote filter now. So there’s absolutely no reason that you can’t already be understanding just what’s out there. It’s just about realizing it’s out there, right, which I think so many of us get stuck in our little boxes and understandings of the world that we don’t even look. Just take a look.

Kathleen Hamilton: Everyone has a skill that is transferable to remote work, whatever it is you do. Whether you’re a Project Manager or you’re really good at detail or you’re really good at writing or content creation. For every single one of those things, there is a remote role, which I think is so exciting.

Clinton Young: Yeah, absolutely. And if you want to get really jazzed up about this whole idea, one of the books that I recommend is the Four Hour Work Week by Tim Ferriss.

Kathleen Hamilton: Oh, yes that’s the digital nomad Bible.

Clinton Young: So tell us a little bit about where you grew up, your journey, and where are you right now in the world.

Kathleen Hamilton: I’ll start where I am now and work backwards. So right now I’m in Portugal in Lisbon, which is very much known as one of the hubs of digital nomadism.

Kathleen Hamilton: And if you are someone that’s interested in travel. I definitely recommend checking out which just has an amazing breakdown of different cities and which are the most popular for digital nomads. It has all sorts of things like costs and links to useful local websites and stuff like that so worth checking out as a resource.

Kathleen Hamilton: But that’s how I initially found Lisbon because I never had Portugal on my like bucket list of places. I was just like oh nice southern Europe, it’s probably really sunny, you know. But actually coming here. It’s gorgeous. I’m absolutely obsessed and in recent times have decided to slow my travel down a little bit and create a bit of a home base and it’s just the perfect place to do that. Also, they really favor and want digital nomads, and people who work in online professions. There’s a lot of nice tax benefits if you actually decide to create your home here.

Kathleen Hamilton: Previous to this, I was traveling for about three years full time and country hopping pretty often. I wasn’t really in one place before the pandemic for more than two months. That was the maximum I spent anywhere. And that was only like once across the three years.

Kathleen Hamilton: Previous to that I was in San Francisco. And I actually grew up in Bali. So I had an unusual childhood and I’m actually the third generation of kids who were born overseas from where they’re from. So my parents also were both born overseas. And my grandparents. I’m originally British, my accent is probably very confusing. It’s a bit of an amalgamation of all the places I’ve been

Kathleen Hamilton: But yeah, so I had the absolute blessing and fortune to grow up in Indonesia and also Singapore and also the UK and meet people from all over the world. So, my love for this lifestyle and for traveling and meeting people from all backgrounds and getting to know, different cultures has definitely been instilled in me from a very young age.

Clinton Young: Would you say that’s one of your passions?

Kathleen Hamilton: Yeah, I guess it must be, you know I had never thought of it that way because it always just felt like a default setting. You know, it’s like saying being at home is my passion. This is home for me. It’s really bizarre but I guess I would list it as one of my passions, and I think that it feels like a really natural state of being for me.

Kathleen Hamilton: I love packing up a suitcase and going somewhere and having to get to know somewhere from scratch. And then my other passions are really around people as well. Pretty much all of my passions are around people. I’m a really person centric individual. My relationships are really important to me. But even larger than that. I think I have a real passion around purpose, and people who are mission driven who are making an impact in some way. I’m really passionate about supporting people to do that. And I’m really passionate about companies that do that because I have a lot of pretty deep ingrained beliefs that companies and businesses and entrepreneurs are the best suited to change the world. And I think that companies that are really at the forefront with their impact that they’re committed to making and who are doing really cool things in the world is something that I’m super passionate about. So I’m really into entrepreneurship, people, and purpose. There’s definitely an intersection with those. And there’s other pieces to that, like, sustainability, just because of growing up in Bali. It was very close to home. And art and activism, all of that as well. 

Clinton Young: It sounds like your passions may have led you to your Ikigaia podcast. Perhaps tell us a little bit more about who you interview on that.

Kathleen Hamilton: Yeah. So is interesting because I’ve never been really been strong at naming. So I actually went out to my community. And I was like, what should I name my podcast.

Ikigai is very much in the mainstream personal development consciousness now so I feel like a lot of your audience may know about it. But for anyone that doesn’t, I’ll just reiterate quickly what Ikigai is as a concept. 

Kathleen Hamilton: It’s a Japanese word and it literally translates into, your reason for being. And basically it takes four concentric circles which intersect; What you love, What the world needs, What you can be paid for, and What are you good at?

And it’s where those four things intersect. It’s your reason for being, the reason you wake up in the morning, why you go and do the things you do.

Kathleen Hamilton: And then Gaia, is the word for Earth. So combining these two words made a lot of sense because I really believe that the world would be a better place if everyone could do what they love to do. More impact would be made if everyone could do what they love to do and actually get paid for it. So that’s the world that I want to live in so the Ikigaia podcast was born. 

Kathleen Hamilton: And I interview people on purpose to have conversations with people who are living the life that they love and earning money doing what they love to do. And there’s so many different models for that. And I think that’s one of the things that I really stand by is that there’s not a one size fits all path. There are different ways of doing it. You can be an entrepreneur who starts your own business. You can be an entrepreneur who helps other people start their businesses. You can also be an intrapreneur working for someone. Right. I think it’s more of this mindset around actually actively wanting to grow and change yourself and learn things quickly and make plans and stick to them. So there’s just all of these different elements and different ways of doing things, depending on what kind of person you are.

Kathleen Hamilton: Ikigaia podcast is all about just sharing those stories so that people know what’s out there. So I try to get really different guests and people who are having very different lived experiences and people across all sorts of ages and socio economic backgrounds and countries. I just love having conversations. Honestly, it was a bit of a selfish pursuit. I’m sure you kind of feel the same way. It’s like having a podcast is such a cool way to get to just connect with people and have those conversations and hopefully bring a lot of value to people that are listening as well.

Clinton Young: Yeah, I love that. Kathleen. First of all, sign me up as a listener, and if you’d like to have me on as a guest, I’m in!

Kathleen Hamilton: I would love to. 

Clinton Young: Okay, so I love to find out how people make money because a lot of people that are considering going overseas or living abroad or even doing it in their own country, perhaps in an RV, they’re like, well, how am I going to make money? So we already covered this a little bit. So listeners, know that there are remote opportunities out there. Whether it be in the exact job you’re in right now, have that conversation with your boss. Kathleen gave some great advice on what to look for in companies if perhaps your company does not have a remote work opportunity.

Clinton Young: So you’re also creating opportunities through your podcast. I know there are ways to monetize that in the future. But then you also are leading people to become remote workers. Is there anything else you’re doing or any additional advice you’d give around how people can make money on the move?

Kathleen Hamilton: Yeah, so I have lots of advice. There’s definitely a few pretty templated ways that you can go about making money while traveling or just living a lifestyle that has the freedom that you want. I’ve had conversations with a lot of people that are like, I just want to not work so many hours in the week and I’m like, yeah, I totally get it.

Kathleen Hamilton: And there’s ways to do that. So ultimately, making money is all just about an exchange of value. When you’re in a job, it’s trading time for money. So in my job, I give my time for money. And I’m ok with that totally shamelessly because I love the ease of that transaction. I’m like, you just want me to show up and accomplish these things. Luckily, I have a job that I absolutely adore and it pushes me so hard to grow. I definitely recommend if you’re in a place where you’re looking for that kind of challenge, go find a startup company. There are plenty of them now.

Clinton Young: Some people that are listening might be wondering, how do I find something that I love. Talk to us a little bit about finding something that’s really aligned with your unique gifts and talents.

Kathleen Hamilton: Yeah, for sure. If you’re looking for templates on finding your purposeful work, Clinton might have some and I have some on my website, which will be in the show notes and at

That’s my website and there’s a freebie section on there where you can find some templates for getting clarity around your purpose.

Kathleen Hamilton: But the easiest way for me, the easiest exercise which I’ll share very quickly, which you can do as you’re listening to this interview.

Kathleen Hamilton: You can actually make a list of all the things that you like doing. You don’t have to love doing them, but all the things that you enjoy doing. And then make a list next to that of all the things you think you’re good at. And they could be obscure and strange and things that you’re like, there’s no way I could get paid for that. Write it down anyways. I guarantee you, someone will pay you for it, like the world is a very big place. So make those two lists. And then the third list is a list of people that you want to work with who are doing something that really lights you up, something you feel like you’re really passionate about.

Making sure young people have access to education might be something you’re really passionate about.

Perhaps you went on an experience where you actually got to interface and have experiences with people who were in a different wealth bracket than you and they were maybe in poverty and that really lit you up. Just write down the things that light you up. 

Kathleen Hamilton: When you have those three things, you’re that much closer to getting to your purpose, what you’re actually wanting to do. This is the thing about purpose, you don’t need to just have one in your entire life. I think we have this idea that you have to find your purpose. And once you find it, that’s it. That’s so not it. You’re gonna find something, and that’s gonna be it for a while and then you can be like, Wow, I really like doing that. But actually, I want to go try this other thing now.

Kathleen Hamilton: And that’s the beautiful thing about life is you have all these opportunities to grow and change. So don’t choose something or avoid choosing something because you feel like you’re then going to be stuck and you’re a commitment phobe. I’m a commitment phobe. I totally get it. You just need to start moving forward towards something, whatever that might look like and start with those three key areas; what you like doing, what you’re good at, and what lights you up. 

Kathleen Hamilton: And then you can do things to eliminate some of them, or actually rank some of those things higher than others. 

In particular, look for where they intersect. If you’re really good at something and you feel that it would help the people that I really care about. Or you’re really good at something and you really enjoy doing it. That’s big and you want to note that, because those are the intersections where you’re actually going to get closer and closer to what you want. And if you don’t have a list of three things you can actually start experimenting in that area by finding jobs that fit that or thinking about maybe you’re the kind of person that wants to start things. So you can be thinking about business ideas to start. Use that framework of those three areas and brainstorm those to actually get yourself closer to what might be a purpose for you.

Clinton Young: I love it. So look at the things that you like, look at the things you’re good at. Look at the people that potentially you want to partner with and what lights you up overall. Well, one of the things you said really resonated with me Kathleen because it happened to me.

I’ve found there’s so many people in the world that really want to make an impact. The world is changing, society is changing the way we think.

We want more meaning in our lives, where things are crumbling around us. Right. Some of the institutions are crumbling. But more importantly, so is the way of thinking. I believe this is shifting and we’re starting to want more purpose and more meaning in our lives.

And we sometimes put too much significance on it. I love what you said. You said your purpose doesn’t have to be the end all be all. You’re not only going to have potentially one purpose in your life, your purpose evolves over time. The most important thing, like you said, is to just be in action. Right? 

Clinton Young: One of the things I share with my audiences when they ask me how to find their purpose. I say, “If you’re looking for your purpose, STOP. It will be waiting for you when you start doing the things that you love.”

Clinton Young: And I don’t mean it’s just waiting there if you take no actions, but it’ll be revealed to you as you get in motion. And guess what. That was inspired (not word for word), but I got elements of that literally from a t- shirt that I bought in Bali.

When you start doing the things that you love like Kathleen just said, the things you’re great at, things that light up, you get into the flow and you start vibrating at a different level. Then you start attracting things into your life. You start seeing things in your life that before you did not see. 

Clinton Young: Okay, so let’s keep rolling. I’ve got some awesome questions for you. I want to go back to three and a half years ago, three years ago before you started traveling full time. Now I know that you’ve always kind of traveled with your family and you grew up in Bali and all over the world and really cool places. But what were you doing right before you decided to travel full time? Bring yourself back to that moment.

Kathleen Hamilton: Yeah, so three years ago, I was living my dream life in San Francisco. So I gotta backtrack a little bit more. Just to give some context to that but I initially went to college in San Francisco straight after Bali and it was kind of a tough transition. San Francisco is a difficult city to live in if you’ve come from somewhere like Bali, because although it has this amazing history and it’s super phenomenal but also it has a massive wealth gap and huge amounts of homelessness and a really hustle culture. Well, you just have to be working yourself to the bone all the time, which is not something that I believe is a healthy mentality. I’m much more into flow than hustle. 

I left San Francisco midway through my college career because I was like, I can’t stay here. I need to go somewhere that’s more my tempo. So I moved to Oregon. But after I finished college, I was like, Wow, I really didn’t have the story I wanted to have in San Francisco. I wanted that to go differently because when I was romanticizing it before I went to university, I was like, oh, but San Francisco, love and peace and the hippie era. And also it’s the edge of the US. So there’s so much innovation and I just felt like I didn’t get to be part of any of that when I first went. So I was like, Okay, I’m gonna rewrite my story and so I wrote the list of all the things I wanted. And this is a huge thing, just having clarity of what you actually want to get out of an experience.

And so I wrote this whole list. And I was like, I want to live in a community house which is like a co op, an intentional community where you’ve got people around and there’s a lot of food sharing programs and all this cool stuff that you get to be a part of.

And I wanted to work at Burning Man. I had just gone to Burning Man the year before and I was like, I’m going to work at Burning Man. They have an HQ in San Francisco.

And I said, and I want to learn to spin fire as well. So I wrote all these things down and within a month of finishing university I moved to San Francisco to my dream Community House. I went and found the fire spinning scene.

I actually just showed up and I had no idea what I was doing. But I had bought my first prop that I could light on fire. And I had an interview at Burning Man. And I was like, wow, okay. That happened very quickly.

So over the course of that year. I lived my dream life. I actually ended up being a volunteer coordinator at Burning Man, which was very cool. I got to meet some phenomenal people. I got to spin fire and actually ended up doing my first performance where I was actually performing live for people, which was really cool.

All this stuff, you know that I actually really wanted to have; these amazing connections of this community house, I got into the whole co op scene in San Francisco.

And I lived literally up the street from the corner of Haight and Ashbury which is the sign that everyone probably knows which is the center of what was the hippie movement, way back in the 60s.

So when all this finished. I was like, wow, okay. I’ve done my year and I finished my visa. I’m not from the US so I couldn’t stay. There was no option for me to stay. I didn’t have employment there. I had already started picking up this online job around GeniusU and entrepreneurship and I was doing interviews of entrepreneurs and writing their stories. It showed me what I had while being in the US. I did start falling into the hustle and grind mentality. I was like, the only way I’m going to succeed is if I work really, really long hours doing something. I don’t like doing this to earn enough money to get to the next step. And things felt really difficult. I was like, well, I’ve had this amazing year in San Francisco. I don’t just want to go and sit in an office. But I also can’t stay in America. So, what am I going to do? I was writing the stories about entrepreneurs and getting paid money to do that. And I was like, Okay, well this is enough to get by. But I don’t think it’s enough to do anything else.

And then I started finding other ways that I could help GeniusU and so I offered to be a community manager and then I offered to help on other projects people were working on. And bit by bit, I grew my income to the point where I was okay and I could actually do something with this. At some point, I just realized that I was working online. I was like, Whoa, I’m actually already working online. This is what some people want to do. I’m in my 20s and I need to see the world. There’s no reason for me to be stuck in one place. And I had just started dating this boy who I told “look, I’m leaving. And if you want to come, you can.” And he was like, yep. Sign me up. And though it just so happened that within a very short period of time. I had a plan.

I had enough income to sustain me and I had a very willing travel partner. And so we just kind of like hopped on because I was like, well, it’s on to the next adventure. You know, I just built this whole one year in San Francisco. There’s absolutely no reason I can’t do that again anywhere I go. 

Kathleen Hamilton: That just kind of became the plan. And we had this whole thing in mind where we were like, yeah, one day we’ll find a place that we love and settle down, but we didn’t have a deadline for that. But now that’s happened too!

It all happened in its own time. But, the long winded story to answer your question, is just to say that I think it was all in the books and I just didn’t know yet.

Clinton Young: Wow, now there’s obviously a level of preparation that you did do on some level, part of it was just a realization like wait a minute, I’m already kind of doing this and I can go travel as well. 

Clinton Young: So how did you know it was the right thing for you to do? I want to talk a little bit about faith, not religious faith, necessarily. What I mean is more of a “knowingness”, like an inner knowing that it was right, even though you don’t know the “how”.

That’s where, in my opinion, that’s where the magic happens; when you know anything’s possible and you just feel it’s right, like intuition. You feel it’s the right thing. You don’t know how you’re going to do it, but you do it anyways.

You have courage to take action. 

Walk us through what that was like for you. How did you know? Was it an inner knowingness or was it logical? What was it for you?

Kathleen Hamilton: Yeah, there’s, there’s a couple pieces to that because on the one hand I 100% believe in your concept of faith. And I do think that there is just trusting the universe, and trusting yourself. And I think even another variant of that is “when you just decide something, the universe conspires to make it happen with you.”

And sometimes a decision is driven by desperation. Right. So for me, I didn’t have a choice but to leave. I knew I had to leave America.

And I really didn’t have anywhere to go. I grew up in a global family which now means that everyone is all over the world, and no one has a sofa for me. So I was like, all right, if I leave, I’ve got to figure out what I’m doing.

I think by the point that I knew that I had to leave, I knew that wherever I went, I’d be fine. There was just this like faith that I had because I managed to make it in San Francisco, which in my head I had built up to be this big scary place that I couldn’t tough it out in. Instead, I had designed a year where I had a phenomenal year and I was perfectly capable. I had built up enough faith in myself by that point that I was like okay whatever I choose to do, I’ll figure it out. I’ll make it work. And I think that’s the kind of courage that not enough of us are taught to have. Even though my parents really did try to teach it to me, I somehow unlearned that courage again and I was suddenly just afraid, but I also think it’s just a rite of passage to learn that courage.

And so by the point that I was ready to go, I just had faith in myself because at a certain point, if you’re going to choose to create a life of uncertainty, right, which is something we kind of touched upon. If you’re choosing to travel and you’re choosing to add another variant of this if you’re choosing to freelance, or you’re choosing to build your own business, then you are creating some level of uncertainty. You’re stepping out of what is a planned thing for you right like University has been planned for you. All you gotta do is show up and take the classes. If you go to work and you’re just trading time for money. Quite often, everything’s planned for you. You just have to show up and do the work. Right?

But if you are choosing to create a life for yourself, no one is planning that for you. And unless you plan it, literally anything could happen. But as soon as you decide what it is that you want to do, and you are very clear about that then you begin a plan. I wanted to travel and be fully location independent and I want to have enough money per month that I can pay my bills and have extra to save. I knew all that. I knew my numbers. I knew what I wanted.

Kathleen Hamilton: And so then when I jumped off and I took that leap, the faith wasn’t just in the universe. It was also in the plan that I had made because I knew that I would do whatever it took to get there. And the universe was conspiring for my greatness. And so was everyone else in my life, you know, because as soon as I told other people this is what I’m doing. They’re like, oh, come crash with me. Come stay at my house.

Actually traveling ended up being way less expensive than living in San Francisco was and suddenly my salary, which at the time I had thought was quite menial then grew to this amount where I was like, wow, I can afford that plane ticket or that train ticket or that Airbnb. Because actually, I’m spending so much less money than I was living in the city.

Clinton Young: That’s definitely a topic that I know I and a lot of people that want to travel domestically and live overseas have that question about, like, how much does it actually cost?

Clinton Young: Yeah, but first. You’re just dropping gold right here for the people out there watching and listening; the power of writing down your goals, first and foremost, you talked about that.

Going back to San Francisco and you even said rewriting your history. You literally rewrote it exactly how you wanted it, and boom you created it in short order. And that’s the beauty of getting clear and writing down what you want. 

And the results aren’t actually linear. It doesn’t have to be like you write it down and then it takes three years. It can happen very, very quickly. So love that. I also love how you touched on hustle versus flow. The US culture is so dominated by hustle. You’re so spot on. And Gary V, god bless the guy, but I don’t really agree with a lot of what he says. But it’s not that he doesn’t say smart things about business. He’s a business genius. I just don’t agree with his context of hustle. Look at the guy, he looks like he’s working 10,000 hours a day. 

And I love what you mentioned about uncertainty. A reality of choosing to go overseas or even to just live in an RV is that you’re creating consciously or unconsciously a life of uncertainty. Bringing consciousness to that fact allowed you to then create certainty by creating clarity of what you want.

You knew your numbers. You knew how much you were making. You knew approximately how much you had to make to live and travel. And what you realized when you started traveling is that you didn’t actually need to even make as much money. 

Clinton Young: Before we talk about some of the great places you’ve been and your favorite places and all that, talk to us about what you need to realistically make to travel and make money on the move.

Kathleen Hamilton: One thing that maybe a lot of us are not so good at is managing our numbers. Don’t get me wrong, I was not going to do this because I was never good at budgeting or numbers, I hated opening my bank accounts, because I was always afraid it was going to be less than what I thought. 

But when I realized that I wanted to go traveling, I started quite consciously knowing how much was in there so that I could save up. There’s definitely lots of different ways to travel and my preference always is to find out who I know in a country before I go there because there’s always an option there.

So you can keep your costs, really low in some cases. Actually in Europe, groceries generally are actually a lot cheaper than the US. That may not be something that you guys know but it can be true. Not all European countries, don’t get me wrong, like if you go somewhere like the Nordic countries. Those are like unanimously very expensive in comparison. 

Kathleen Hamilton: We started off in the UK, which is familiar to me because I grew up there and the currency is the pound, which used to be a lot higher valued. It’s not so much now, but that was a tricky thing, currency conversion. 

The cost of living per month, traveling with a partner, and sharing living costs, was about 1,500 euros each, which is about $1,500 USD as it’s not a massive difference in currency conversion. So together we had a shared expenses of 3000 Euros or $3,000 USD. We were obviously buying groceries together. Those were the same numbers even in the months where we were doing like seven countries so it includes travel. We had bought a train pass and we hopped countries for two months. 

Kathleen Hamilton: So we did seven or more countries in one month, and it was like you know that’s that’s a third of what I needed in San Francisco. That was my rent only in San Francisco. But traveling, $1,500 paid for groceries, paid living expenses, paid travel expenses, and paid all of the different bus passes in every country. It was super inexpensive and I know people who do it for less money than that. As soon as you get to Southeast Asia for example, you’re looking at like 1000 euros or $1,000 US dollars a month and you would probably be fine if you were willing to live in shared accommodations or accommodation that wasn’t the Marriott, you’d be fine on that much.

Clinton Young: Let’s talk about that a bit more. So $1,500 approximately per person. And of course, you shared expenses. So what would you say it would likely have been for a single person? Would be about 3000?

Kathleen Hamilton: I actually think in Europe as a single person, you could do it for more like 2000 euros or $2,000 USD and that’s if you were renting Airbnbs solo. If you’re looking at hostels, you can do five euros a night hostels and it’s cheap as chips. So, and obviously I don’t know the age of your audience, but so there are some people that say they wouldn’t live in hostels, but you can also go to hostels that have private rooms. And there are all sorts of variants or grades of hostels. Also, now there are amazing co-living co-working options that are higher priced, what I would call like higher end, which are based around co working spaces. So there’s co-working spaces, now that have popped up with living spaces and they’ll have multiple countries where they exist. So you can buy a membership and then your actual accommodations are really low cost.

And that’s a really cool way to travel as well, obviously, find a co working slash co living organization or company that you vibe with. There’s a whole bunch of those as well. 

Clinton Young: I would love to know if you have a tip of one right now that you’ve heard of for the co live co work option.

Kathleen Hamilton: Yeah right off the top of my head. is one they have some amazing tropical destinations. So if you’re looking at South America. They’re pretty awesome.

Also is one that I know and personally love. I haven’t stayed with them, but I’ve used their co-working spaces, a lot. They’re super cool and yeah I like what they’re doing around the world as well. They also have a lot of locations. 

Clinton Young: You’re wonderful; that’s brilliant advice. So in terms of the ranges, it’s about  $2,000 for an individual, $3,000 for a couple in most countries and a little less in Southeast Asia.

What are you guys typically looking at in terms of places to stay for $3,000? Are you looking at hostels at that rate? Are you looking at Airbnb, or a combination of the two?

Kathleen Hamilton: Yeah, up to now, we basically exclusively have done Airbnb. And the reason for that is I work from home and now my boyfriend does too. So we both work online. So we need guaranteed good internet. We need guaranteed quiet time so we can get our work done. I think now, if I were to do it again from scratch. I would probably go with one of the co living co working options, but when we started, we didn’t know about them and also I didn’t look for them honestly. I also think that they’ve only recently become popularized. I didn’t know a lot about being a digital Nomad. In fact, I kind of pushed away from the term itself to begin with because I was like, that sounds really pretentious to say I’m a Digital Nomad. But then I started doing it and I started meeting digital nomads. And I was like, man, these people are all so cool. There’s always sour eggs in any basket. But for the most part, everyone we’ve met has been amazing and co-working spaces have changed my life. Actually going and sitting in these beautiful environments that have been designed for productivity and work and focus. Being around other people who are working on inspiring and uplifting projects or just a start up or whatever is very invigorating to be around.

Kathleen Hamilton: And so I started going to more of those when we were traveling and I didn’t have good Wi Fi or we were in a city where I had access to them. So, when we were in Bali, I just got a co-working membership for a month because I get so much more done than I do, sitting at home. And I get to meet all these cool people. And there’s always awesome events as well. If you’re planning on traveling around the US, I guarantee, there are cool co-working spaces and worst comes to worst go to a Wework. Wework is everywhere and they have some cool events. I found them not as warm and friendly as some of the smaller co-working spaces because the smaller ones seem to really want to focus on cultivating community, which I think is super cool.

Clinton Young: Yeah. So in terms of pricing, do you have an idea of what a co live co working space would be, or have you not yet experienced them?

Kathleen Hamilton: I’ve actually looked at a couple. Let me see if I can dredge it up out of my memory. Usually when we are looking at Airbnb it’s for the two of us to stay together. The cap of the nightly amount we want to spend is around 60 euros or $60. We generally don’t want to spend more than $30 each per night because then it starts getting pretty pricey right. We prefer even lower than that if possible. 

Clinton Young: For that price point. What are you getting typically?

Kathleen Hamilton: It depends where you are in Europe. Generally in the more standard countries like Prague, Czech Republic, France; places that you don’t think of them and say, Oh, that would be really expensive. Like when you think of Switzerland for example, that’s going to be really expensive. If you don’t have the knowledge of Europe, you can just do some browsing on Airbnb.

Kathleen Hamilton: But I would say usually for like 60 euros a night you’re able to get your own apartment with a kitchen, a closed bathroom, so not like a studio apartment. I try to avoid those because then you’re in the same room all the time. You want a bedroom with a door and a living room. For that rate, it’s usually relatively spacious. I think the place I’m in right now is actually a little bit less cost than that. Obviously, if you’re smart with how you plan your travel, if you do plan a little bit ahead, which we did not, then you can actually find places that are cheap and really nice a lot more easily. So if you do like to plan ahead, I definitely advise doing so. Even if you don’t though, you’ll still find spots. They may be a little bit harder to get to or not in a city center so look up public transportation wherever you go. Because when we were in Sweden, for example, we only stayed for two nights, because it was super expensive. But we had to stay pretty far out of the city center to cut costs because we knew that we could get a train and the train rail system was amazing.

Kathleen Hamilton: So you can be smart about how you budget. With the two of us, we would both pay for things out of pocket differently. We don’t have any shared accounts. So we got into the habit of tracking how much we spent so that we could get that money back from the other person. Neither of us is the sole breadwinner, we share equal costs. Because of that, we got into this really good rhythm of actually checking our expenses and knowing how much was going out every week. So if there was a week where we spent more than we wish we had, we would then cut our costs the following week. So our flexibility allowed us to do that.

Kathleen Hamilton: If you’re planning ahead, rather than doing what we were doing, which was doing it entirely on the fly, you may design whatever you’re going to do with that in mind. I do think that is a smarter way to do things if you are the planning type.

Clinton Young: Yeah. Tell us about your favorite locations and also the most affordable ones. Best value versus just best experience. Share anything you want to share about that that’s fun for you. Share with us the countries or cities.

Kathleen Hamilton: Oh my gosh. Well, in the last three years, I’ve done now 23-24 countries. In my lifetime, I’ve actually done 40+. I just tallied it up the other day. I was like, wow, that’s actually a lot of countries. I’m only 25 and have been to 40 countries. I’m going to get to 50 by the time I’m 30, that’s my plan. So I’ve got 10 more I want to do in the next five years, which is totally doable.

Kathleen Hamilton: I just came back from a trip to Greece and that is still really stuck in my head. So I’m going to give a couple of areas in Greece that are very affordable. If you go to the islands. So like Crete, for example, there’s some amazing hostels that actually feel like four star hotels because you can get so much value for money. The food is phenomenal. And the beaches are amazing. I can’t say some of the best in Europe, because I haven’t been to that many European beaches, but I imagine they’re pretty high up there. So Crete is amazing.

Kathleen Hamilton: The water is so blue. It very much feels like a dream and I know some of the other Greek islands are also very beautiful. Some of them are very expensive, though. But Crete is one that I enjoyed and was good value for money. If we’re staying on the tropical island route. I mean, Bali is every digital nomad’s dream. I think growing up there and going back as an adult was a weird experience. I still love Bali and have a very fond place in my heart for it. Sometimes you can go to Bali and it’s so inundated with tourists and people that you may say, is this the right thing to be doing. Am I helping or hindering the progress? But in North Bali. If you’re going to go, go to North Bali, go to the islands and you’ll get that secluded kind of feeling. It’s amazing value for money, pretty much everywhere in Bali. So it’s one of those places that people go and stay for quite a long time, which I totally recommend doing. If you’re going to go, spend a few months there and you’ll just get a lot more out of the experience. Bali likes to teach difficult lessons. So it’s a good place to go if you’re looking for some spiritual transformation, which you probably know if you watched the movie Eat, Pray, Love. Don’t use that as a guidebook though. Go and meet some locals, meet some nomadic people at co working spaces and you’ll get the tips and tricks that you want.

Kathleen Hamilton: So Greece, and Bali and then I am in love with Portugal currently, so that’s a big spot for me. Also Prague is amazing for the tourist stuff. I reckon, go and see some castles and cathedrals and it just really sets off all of the amazing fairy tale kind of imagery that you’ve always dreamt of. Prague is definitely the place for that in the Czech Republic. So yeah, I’ve given you a few of my favorites, but I have loved everywhere in a different way.

Kathleen Hamilton: I’ll give you some place I didn’t fall in love with for some reason. I didn’t fall in love with Denmark and I would love someone to prove me wrong. I really want to go back and explore the outskirts. Copenhagen is not a city that I fell in love with. But if you like cycling, I’m sure it’s amazing. I just walked around everywhere. And it felt very flat.

Kathleen Hamilton: But yeah, actually, most of the places I loved.  

Clinton Young: Have you been to Spain or Italy?

Kathleen Hamilton: Yeah, so I’ve been to Italy multiple times. I haven’t gone in the last two years, which is why I didn’t mention it, but I adore Italy. I haven’t been to mainland Spain. I’ve been to some of the Spanish islands. So I’ve been to Tenerife island in Spain when I was younger, but I haven’t been to Spain itself. It’s very close to Portugal. So I imagine there are some similarities and I have friends who rave about Barcelona. Actually Dominic my boyfriend raves about Barcelona, so it’s definitely a place I want to check out. And then they have Granada, which is by the beach and I also want to go there. It’s a 40 minute drive to the beach, but also has mountains for snow sports, which is crazy to me that you have all that in such close proximity. 

Kathleen Hamilton: But Italy, I loved. There’s something really special about traveling in Europe, and that’s the reason why we’ve spent so much time here the last couple years. It is so freaking old and I love that. If you live in America, your civilization is younger than most of the buildings and most of the cobblestone streets here, which is just a trip to think about. Yeah, and Italy really felt that way to me. Obviously, being in Rome and seeing the Colosseum, but also like Florence, they have amazing fountains and gardens and you walk around and you’re just blown away by the stories and the history and the mysticism. I really loved the south of Italy. I went to Naples and it was just stunning. 

Kathleen Hamilton: A road trip through Italy, I think would be a cool way to do it because there’s so many little cities all over the place.

Clinton Young: How was it financially in Italy?

Kathleen Hamilton: If you’re in Rome or Milan, it’s very expensive. I went to Milan and I actually couch surfed, which is an interesting way to travel. It’s called couch surfing and people just offer you their couch and I stayed with some random dude from couch surfing and it was very safe. I felt fine and I got to meet a very cool community, but it was quite expensive for me at the time that I didn’t pay for accommodation anywhere. And I was a bit younger. I was in university when I did it. So I was a lot more stingy than I am now.

Kathleen Hamilton: But Naples, go to the south of Italy, and oh my gosh I was actually blown away by how cheap it was, the food and produce if you’re actually going to travel there and cook for yourself. It was so cheap and all the restaurants were very cheap. I remember buying unmarked bottles of wine from a guy that made them in his basement for two years, and it was amazing wine. I definitely recommend the south of Italy, and then, a lot of the coastal cities are very, very cool. I haven’t been to loads of them, but definitely I would recommend checking them out and doing a bit of a road trip because then you can actually see a lot of it.

Clinton Young: Yeah, that’s definitely on the agenda. So what are some of the big challenges or things to look out for.

Kathleen Hamilton: Yeah, Internet access if you’re going to work remotely, I think if you’re choosing this as a lifestyle where you’ll be remote working and doing the digital nomad thing, or running your business while on the road, then you have to plan for a whole lot more. You need to make sure you have solid internet access. Actually, if you’re staying at an AirBnB, or you’re paying for accommodation somewhere, you have the right to and you should ask for a speed check of the Wi Fi before booking. I recommend you also become part of the digital nomad community even before going. I didn’t become this knowledgeable beforehand, I just did it. That’s definitely 80% of it, just going through the experiences. But I also highly recommend that you join some online communities. There are loads of free Facebook groups for digital nomads or remote workers. When you go to different cities, there’s now city focused digital nomad groups as well. So they’ll have insider tips of the place that you’re in.

Also, which I mentioned earlier, which is a great site to just find tips. They also have a paid community that you can join, which is cool, or you can join my community, which is free at And I’m happy to give more tips and tricks and stuff. So definitely Internet access is critical. Having a routine is impossible and also necessary. So figure out what works for you, whether that’s project management software or I use a bullet journal. So I physically write in a notebook and have it on paper because I just find that that’s the most powerful thing for me. And I know what I need to do every day. I didn’t do that when I first started traveling and I always felt this combination of being overworked and not getting enough done, like you’re spinning your wheels.

Kathleen Hamilton: So I recommend finding some way to plan for yourself so that every week you know what you need to get done and every day you know what you need to get done and you just do that. And then step away because otherwise you’re just going to find that you will sit and work. Your work is always available to you on the computer and then you miss all the other stuff. You didn’t start traveling, just to work right? So make sure that you’ve got your structure and your plan in place so that you can step away and feel good about doing that because you’ve done what you needed to do for work already.

So I think those are probably the key things because time management and internet access are the most challenging things about being a digital nomad. As long as you’re planning and you’re aware of your limits and boundaries in terms of cost and physical ability, then you can plan around that. But it is a conscious effort, but you’ll thank yourself for it later.

Clinton Young: For those people out there that are hearing the term digital nomad and maybe they’re not feeling very digitally experienced, what would you say to them? 

There may be somebody more like me who is digital, but I’m not like a graphic designer for example. They’re not bloggers. They’re not somebody who writes copy for a living. I’m a speaker and I train people on how to become speakers, so I do a lot of work on zoom and online, but what about folks who are like me, or even that maybe have a different type of thing going on, but it’s not necessarily something where they make money with their efforts on the computer, although they do use it.

What would you say to them?

Kathleen Hamilton: Some advice, don’t be turned off by the digital nomad nomenclature. It’s just about how you are able to make money on the move, which will likely be digital. However, don’t be afraid of digital because actually having your digital systems in place is what’s going to allow you to step away from the computer in the first place.  

I 100% recommend getting a consultant for that if you have the means to. There are people who will help you turn your business digital which will allow you to travel.  If you currently run a business in that place, I guarantee you can hire a team to run that for you. That will allow you to step away, so have the courage to do that. Pretty much all the time, whether it is a time constraint or physical constraint, If you hire someone, you’re actually going to make more money in less time and you’re going to be able to step away. I definitely recommend analyzing where you’re at and if you’re willing to bring other people on and trust other people to help you with what you’re doing. 

If you’re currently working a job, and you’re looking to transition to an online role that gives you the freedom to travel, all of the skills that you already have are totally applicable. So don’t be afraid to take a look after you’ve listened to this; go and on a job search for the stuff that you do but specify in the job search that you’re looking for remote work, and you will see stuff pop up. Think of other jobs that you would enjoy doing that maybe aren’t what you’re doing right now, but you feel you might have the skills for. Put the filter on for remote, even if you just Google “remote work job boards”. There’re so many now and the first page is always filled with tech roles. Do not be afraid of that. Go past the first page for your search terms and you’ll find jobs that fit what you do. It may feel very unattainable, because I think we’ve been deceived into believing that it’s only possible for tech workers who make $10,000 a month, which is false. You know, you’re not going to be that person and that’s okay.  

There are other options, but pretty much anything you do, chances are, someone else needs your skills. Start looking at people who have started their own businesses using those skills, because one thing that really opened my eyes is virtual assistants. There’s a whole movement in the digital nomad community around people who have become virtual assistants. There are people that think they don’t have any skills, they’re really organized. That’s a skill. Yeah, I would pay you to organize my calendar for me, like I pay someone to edit my podcast for me because I don’t like audio editing. 

So there are all these little things. For instance, my brother is a video editor. He now does that online, and other people pay him to edit YouTube videos. You know, there’s literally a profession for anything. 

Kathleen Hamilton: Obviously, those are really digital examples, but if you can do accounting, be a bookkeeper. If you know you have good sales experience, sell something. There are roles for you in all of those places and more, like real estate. I guarantee you can do those things online or overseas. There are all sorts of online brokerages now. Really anything that’s traditional has been transitioned to digital.

Clinton Young: Great advice Kathleen, great advice. So I want to hear either your funniest story traveling overseas or the craziest thing that’s happened to you that maybe you didn’t think was gonna happen.

Kathleen Hamilton: Yeah. Wow.

Clinton Young: Or if it hasn’t happened to you yourself, what’s this the funnest thing that’s happened to someone else 

Kathleen Hamilton: I think… Wow! There are actually so many, where would I even start? 

One of the craziest things that I had the opportunity to do was actually go to Tibet, which I didn’t expect to happen. It was never in my plans. It just so happened that the company I worked for was running a trip there and I had the opportunity to go. So I ended up going and it was one of those things that when I was a kid, I really wanted to go to that. And I had just kind of forgotten about it. Then I had the chance to go and see the monasteries, see Potala Palace,see Everest from a distance, but still see Everest. Nonetheless, and it was just so mind blowing. I wish I could think of a funny story, off the top of my head, but honestly, that There Are a lot of highlights over the last few years, which you’ll find when you design a life that you really want to be living pretty much every, every experience is a highlight in some way. But that’s definitely a big one of mine. 

Clinton Young: Yeah, I can only imagine that being very inspiring. 

Kathleen Hamilton: It was a great experience, and it was bizarre because it’s also ruled by the Chinese. So it’s actually Chinese territory, which was a trip. We actually ended up losing our certificate that was required to go in as a group and authorizes you being there. One of our group members went on a different flight than us on the way out and got detained in China for like a week because you’re supposed to enter and leave as a group.Of course we didn’t realize that and so we had different flights booked back and she had another connecting flight through China and then they wouldn’t let her leave China because she had separated from us. She had an amazing experience other than in China, apparently, which was not the best experience for her, but she did end up turning it around, which was cool.

Clinton Young: Wow, good to know. So what would you say are some particular vendors of equipment or backpacks or any any vendor of anything that you’ve noticed? You’ve mentioned Airbnb. Obviously that’s a great resource. Anything else that we need and also tips on like what not to bring with you.

Kathleen Hamilton: So, interestingly, I did start with a backpack. I started with an 80 liter backpack, which was a terrible, terrible idea. If you are going to go the backpacking route,

pick a backpack and stuff it full of things and carry it around your house. Or go on a hike and decide how much you hate it. I ended up transitioning to a wheeled suitcase, because why would I carry it on my back when I could just pull it around. And because I was in Europe, and it was all trains or planes, that was fine. I could just drag it around. You probably need a lot less than you think you need. Try to pack light and be smart about it, and if you want to bring gifts and stuff, ship them from whatever country you’re in. Don’t try and carry them around with you if you’re doing long term traveling. So, I actually went with the roller suitcase, and I would never go back.

Figure out what works for you depending on where you go. If you’re going to Southeast Asia, a backpack or a duffel bag is probably better just because you’re going to be hauling it in and out of places a lot. If you are going to be working on the road, get a laptop stand. Do not do this whole like just traveling with a laptop thing. Your spine is not going to be happy with you. So get a laptop stand I have the Roost Laptop Stand.I think they did a Kickstarter campaign and now they are selling them online. I think it’s the best, because it collapses down really easily. But there’s loads of more inexpensive ones. I actually think this one is quite a high price tag for what it is. There are inexpensive ones. 

Get a bluetooth mouse and a bluetooth keyboard, so that you can just pack it all in a little laptop bag. Have your keyboard and your mouse and then it’s like, oh, it’s like a desktop setup like you know I’m sitting on it now and it’s at my eye height and it’s just so much better. So yeah, I recommend you either have a phone that has a good camera or get yourself a camera. But if you have a phone that has a good camera, and you’re not a photographer, don’t buy a camera. I bought one and I never used it, because my phone was fine.

Those are just some technology hacks.

Kathleen Hamilton: Get yourself a universal adapter, because you’re going to need it, and pack all your electronics separately. Whether that is a pouch that you can pull out really easily. If you’re going through airports, you’re gonna have to unpack your bag and you don’t want to be that guy in the security line who’s like taking forever to unpack their bags. We all look at them and we hate them. So don’t be that guy.

And get a reusable water bottle, and that’s probably my last tip I guess. In terms of places, Hostel World is a really good one for hostels. It’s like the conglomerate of all hostels that are worth anything. So, Hostel World is really great for hostels, Airbnb obviously is great. I do think Airbnb is where we’re going to see some shifts in the next few years. I don’t think it’s going to be as easy as it was when I was traveling. It’ll probably still be around, but there are now other companies and stuff popping up that are local for short term stays. So, give it a quick Google before you get to where you’re going, and try to book in advance. I would say two weeks plus in advance is really awesome. You’ll have a lot more options. Once you get down to around one week, you’re really pushing it. And yeah, just use the internet – it’s there for you, right? We are more connected than we ever have been in the past.

You can use it to be a part of any community like. If you like board games, there’s probably a board game community in the area you go to. I say that because Dominic really likes board games, and we have pretty much gone to a board game cafe and every country we’ve gone to, and we’ve met all these cool people. if you’re into cats like whatever, if you are into any animals, there’s Trusted House Sitters. Trusted House Sitters is awesome, there might also be a Trusted Pet Sitters, but if you just Google “trusted house sitters”. They have an official site and they basically vet you and check that you’re cool. Then if you decide to go somewhere, or you have loose travel plans, people are always looking for others to house sit their house or take care of their pet pets while they’re gone. Then you get a free stay. I know someone who traveled the world doing that, and they didn’t pay anything for accommodation. So clever; so smart. I never did that, but I probably will in the future. So there are definitely lots of smart ways to do things. 

Do not be turned off by things that you perceive to be issues that might not even be issues. Talk to people that have done it, because pretty much all of us are friendly. 

That might be a massive overgeneralization, but I’m friendly. I know a lot of digital nomads, and people that travel full time who are friendly. Definitely reach out and join the community. If you ask questions, everyone’s down to help you. Know you’re not alone in this.

Clinton Young: So, in closing, two more questions for you. But to what you just said, you’ll meet some of the nicest people and most interesting people, and if you’re considering doing this, you’ll probably have some things in common. At the very least, a love for travel or adventure or culture.

My wife and I went on our honeymoon to Peru for three weeks in South America, and we traveled all around. We really planned the first two days and everything else was just whatever we felt. We would just do it.

We stayed at hospitals like you’d mentioned, even on our honeymoon. We didn’t stay at them all the time, but they were amazing.

We found this one hostel – there was basically a really famous artist out of Lima, Peru, who has two different houses, one in Cusco and one in Lima, and we stayed right on the ocean in basically his mansion. This was all with a hostel.

Kathleen Hamilton: Okay, that’s amazing.

Clinton Young: There was another amazing one out in Cusco. So, don’t be afraid of hostels. they’re like 3 and four star hotels in some cases, with way more character.

Kathleen Hamilton: So much more character, and a lot of hostels have cool socializing areas. If you stay at a hotel, or an Airbnb, you’re kind of like on your own, but hostels’ whole purpose is to have travelers meet each other.

For sure, an awesome experience.

Clinton Young: The two coolest people we ever met on any of our travels were people just like you, who were traveling. They’ve been traveling for three years now. They were teaching English and teaching different languages, and we met them in Peru as well. 

Side note, real quick question. Do you speak more than one language? If so, how many? I’m just curious.

Kathleen Hamilton: I speak quite a few very badly. The only one I’m fluent in right now is English. I’m currently learning Portuguese and I speak very basic rudimentary Spanish. I did study French for a long time, and I can speak that basically. So how many? Well English Portuguese, Spanish, French. I speak rudimentary Swahili because I had a boyfriend in high school, and then we traveled to Zanzibar together. And so I speak some Swahili. I speak Indonesian conversationally, very basic, just because of growing up there.

I think that’s it. So yeah, five languages, but really only one language, if we’re honest. The other four are just very, very basic

Clinton Young: That must be helpful, I would imagine.

Kathleen Hamilton: Oh, for sure. I mean, ultimately anywhere you go, I always recommend learning the basic phrases, because people will be appreciative of it, even if they chuckle. A lot of countries do speak English really well. So people will speak it, like in Portugal. In Portugal, I will go out and I’ll say a few words in Portuguese, and then they’ll be like, “do you actually speak Portuguese?” and I’ll have to say no. So, they’ll transition into English, and it’s fine.

In countries where they don’t speak English and you try, they’ll chuckle and there’s a lot more goodwill when they know that you’re making an effort, you know? So I always recommend picking up a few phrases wherever you go, even if you’re really bad at them.

Clinton Young: There you go. I went to Brazil for quite a while in grad school, but that’s the extent of my Portuguese.

Kathleen Hamilton: I would love to be learning Brazilian Portuguese the pronunciation is so much easier to me than Portuguese in Portugal.

Clinton Young: Yeah, I agree. I studied culture in grad school. It’s so vital when you’re traveling to just make the effort, because it shows respect and immediately creates rapport. 

Some people might be like, Oh, you don’t speak my language. Right. but I just totally tried to make a French accent, which is totally terrible, and no offense to anyone who’s French

Kathleen Hamilton: Are you kidding me? The one place where I’ve really been, just shot down.

Clinton Young: Yeah, but I had an amazing experience there recently, so it didn’t actually happen to me, but it did happen to my wife, yeah. So no matter where you’re at, you’re going to have those one or two people, but the majority of people are going to really open their arms and want to help you show some effort. 

So, yeah, great advice there. 

Now. In closing, I just want to hear a little bit more about what you’re up to, what you need support with, what can we promote for you? How can we support you, and also, before you do that, any last bit of advice that you would give to people that are considering this lifestyle of travel?

What would you give for advice? And then let’s go into what you want.

Kathleen Hamilton: So final advice is, I guess, a question to them, which is, “if not now, then when?” Right? So figure it out and do it. You’re gonna thank yourself in the future. But if you don’t even take steps forward to doing it, you’re going to be living the same life and for a few more years, and probably be kicking yourself for it.

And yes, we are currently in a global pandemic. I don’t know when this episode’s coming out, we may be more on the other side by then, we hope, but there are still smart and considerate and conscientious ways to see the world, if that is something you want to do.

Just be conscious in the way that you’re doing that and, you know, there’s no reason that you can’t still be moving about and living overseas, or living in a van, or doing whatever kind of lifestyle you want to do. Whatever it is that you want to do, get clear on it and make it happen. You’re gonna thank yourself.

Clinton Young: I love that advice, Kathleen, and you actually reminded me of the last question, I forgot to ask you, around COVID. With that happening, I know some people are choosing not to travel. Is it possible to still travel? You just went to Greece, right? Yeah, one bit of advice there.

Kathleen Hamilton: Yeah, I think like with anything, there are always ways to find solutions. I do think, particularly in the US, you’ve got a pretty major problem, which is that most of the world has blocked you out. I say most of the world, though, right, like there are still some countries that are willing to take like us travelers.

So take a look at those and maybe it’s not a place that you originally thought you would go, but it might end up being a really interesting experience. A lot of places now have quarantined me. That’s not a problem because I work on the computer. So, I’ll stay in a house for two weeks and then come out the other side, knowing I’m healthy. That’s fine. And I travel with a partner, so it doesn’t feel as isolating. So, I know if you’re traveling alone that’s probably a bit more of a hindrance. But, you know, if you’re willing to take it slow, not trying to do too much all at one time, and to follow the local laws, then yeah, there’s no reason you can’t still travel.

I do think that a lot of people who have been traveling for a while are deciding to settle down, just because people who have been traveling for a while, used to how things were. So in any case, we’re trying to create some kind of normalcy in our lives, myself being one of those.

Settling down for a bit is what makes most sense to me right now. But you bet as soon as any of those borders are opening, I’m going to be doing weekend trips, because when you’re in Europe, everything is so close.

But yeah, actually getting to Greece was very easy. They COVID tested us at the airport and then never sent us any results and didn’t keep track of us, so we kind of just island hopped after that, and left the mainland, which was fine and all of us were healthy and wearing masks. So it was all good. So yeah, I think the future of travel has changed, but it hasn’t stopped. There are still industries and people and actually flights and accommodation that are cheaper than they’ve been in a long time. So there are definitely lots of options.

Clinton Young: Were there Airbnb restrictions at all, or do most people allow travelers?

Kathleen Hamilton: It depends on the local laws. Here, it was like if you’re from Europe, or you’ve not been to America recently, then you’re fine. They all would have more rigorous cleaning that’s happening. So there are higher cleaning costs. Actually, people wanted the guests so badly that the cleaning costs were higher, but the accommodation costs are lower. So it was very reasonable to get accommodation.

Europe has opened for travel now, so it’s getting busier here already. Lisbon now is busier than it was. We were here two months ago, and it was dead quiet. You know, just before we went to Greece, we were here, and it was silent. And now there are crowds again because Europe has opened a bit more. But yeah, definitely still lots of options for travel.

Well, Kathleen, you’ve inspired me. You’ve inspired me in a lot of ways, and one of those ways is to come to Lisbon at some point. I’ve researched it already after connecting with you online and it seems like it’s an amazing place. And you’re right, it was nowhere on my radar.

That’s the beauty of travel. You learn about all these different places that you never would ever see if you don’t just get out there and learn and connect with other people. So tell us about how we should support you in closing, and I was going to thank you so much for being a guest and sharing all of your knowledge today in our journey.

Kathleen Hamilton: Thank you. Clinton. It’s been such a pleasure. I’m excited to have you on the Ikigaia podcast, which is the first way people can support if they’ve enjoyed any of this. This is very similar to the conversations that I’m having with different people around their Ikigai. It’s a podcast talking to people about purpose. So come and check that out. You can find it by searching Ikigaia on any of your podcast players or at which is the website for it, where you’ll find all the show notes.

The other way that you can support is definitely to join my online community of purposeful remote workers or access any of my freebie content. You can find that over at and those are the two key places that I hang out.

All of my links are on my website, you can find them super easily, but I hope that anyone who is looking for advice, or is in a job looking to transition into remote work come and find me. I have free call links on my website. I would love to support you in transitioning to actually creating the life that you really want to create, as well as the freedom and the earnings that you want. So that’s it. Those are my key areas.

Clinton Young: Love it. Thank you so much, again, Kathleen, if you are somebody that wants to travel or wants to transition, Kathleen is an expert, she’s been doing this virtually her whole life. Thank you Kathleen. You’ve given us so much knowledge today, I appreciate you so much. Have a wonderful rest of your day.

Kathleen Hamilton: Thank you so much. Clinton. I look forward to seeing you in Portugal.

Listen to Kathleen Hamilton’s podcast at and join her awesome global community to access her freebie content on her website 

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