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Ep. 261: How this American sold everything to move to Europe and now shares expat life tips on YouTube with Jessica Cutrufello

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In this episode, I speak with Jessica who is an American who sold everything and moved to Amsterdam with her husband when she was 29 years old. 

She now documents her travels around Europe on her YouTube channel and blog, A Wanderlust For Life where she highlights European gems through food and memorable experiences as well as expat life tips.

Listen on to find out how Jessica shares memorable experiences and expat tips through her Youtube Channel.

Listen Below:


Ep. 260: How this Former Journalist Left Retirement to Run Popular Travel Blogs at 68 Years Old with Leyla Alyanak
Ep. 259: How to Start Trying Remote Work with Debbie Arcangeles
Ep. 258: How this travel blogger inspires women to get outdoors with Natalie Nealan




Hey everyone. Thank you so much for being here. I am really excited to be with my guest today. I’m here with Jessica. 

Hey, Jessica. 


Hey, how you doing? 


I am great. Thank you so much for being here and for sharing with us your journey. 

Can you tell us more about you and why you live an offbeat life?



I’m Jessica, I’m originally from Virginia, in the US and I moved to Amsterdam in the Netherlands, in 2014 to pursue a different kind of life. And since then, I’ve done everything from work in startups for, like, 200 euros a month working for a big international company to working for myself. 

And I travel as much as I possibly can around Europe.


That is awesome. 

I am sure a lot of our readers want to do something similar. But what made you decide to choose another lens? Because most people will be like, “I’m going to go to Bali or go to Mexico, somewhere tropical,” but you took the opposite way. You wanted to go to Europe and you wanted to go to the Netherlands. 

What made you decide to do that? 


Actually, that’s just pretty simple for us. 

So, my husband, the way we’re actually allowed to live here, is he got an Italian passport through his family lineage. And so it was really easy to move to Europe compared to most other ways to do it. 

And he does something very specific and he was able to try to find work specifically because there are a couple of hubs in Europe and we tried out a couple on holidays and fell absolutely head over heels in love with Amsterdam and we knew it’s where we wanted to settle. 


That is pretty amazing because it’s so interesting how you are able to do that with your husband and then you traveled around and figure out where you wanted to be. Have you been staying there since 2014 or have you guys moved around to different locations? 


We’ve been here since 2014. We started out in an Airbnb. We’ve found an apartment and then we bought our house about 5 years ago and it just felt like home within the first six months and we never had a desire to move anywhere else. It’s always been here. 


That’s awesome. 

And when you both decided to relocate and go to Europe, what was the catalyst for that? Was there, like, a moment where everything just changed and you knew you both needed somewhere different, or was just this thing that you kind of thought would be an interesting thing to do for a little bit but now it’s kind of like a forever thing?


That is a very interesting question. Of all the times I’ve been asked about my life, I’ve never really had that one. 

I think that we moved because we wanted something different. And when he got it in his head that he could get his Italian passport, it just seemed like an opportunity to do something different. I don’t know if we ever thought long and hard about if we were going to move back. I think it was just a here-and-now kind of thing but it all happened very fast.

I think he got his passport in March or April. In June, we decided we were doing it, by August, he was over here looking for work and I joined them two and a half weeks later. 

So within the span of six months, it was just selling everything and then deciding to move. I don’t think we had a long-term plan for that. 


Well, it worked out well for you, obviously. Because now you’re doing all of these things and you’re working for yourself. Did you always know that you wanted to start working remotely and for yourself or did it happen where you finally figured out that that’s what you wanted to do?


I never thought that, actually. I guess it’s kind of snuck up on me.

When we moved, the way it works is because he’s an Italian citizen. You can live anywhere in the EU and register but for spouses to join you, you have to make a certain amount of money. And there’s a process, obviously, that goes along with immigrating anywhere. 

And so, there was time between when I got here and when I could legally work. And in that time, I started a blog and we kind of had in our head our own vacation, which is anybody who wants to do the expat life, try not to spend your entire savings in the first month thinking you’re on vacation.

But yeah, it was just this anything that happened that I wanted something to do. And so I just started writing about our journey and writing about when we went to Paris and it was all very new and shiny. And I just had to get that down but it’s never linear or I feel like it’s not usually linear. 

So I did that for a while but I needed to work, I needed money. And so I just knew that I had to start meeting people and getting a job. And so I started interning for really no pay with startups and then I got a little bit of pay. 

And then I ended up working at the same company as my husband, had a totally different department for three years, got a permanent contract and everything. And then it was just something that felt like it was missing. 

And I love working in a team, I like what I was doing but it didn’t feel right anymore. And we were in a financial position where I could try. I could just try to go out on my own and start my own business and did not much long after to make it.

So, it’s just been a roller coaster, but I feel like when you know that you want to take the leap and you know that you can, that’s very empowering. 



And it’s interesting how that works out. I have talked about this with myself too, Jessica, where the job that I had left before, going and starting my own stuff is that it was the same thing. It wasn’t bad, I enjoyed it, I enjoyed the people that I was working with and the company that I was working for but, like you had mentioned, sometimes something is just missing from your life that you just really want to do and you want to try. 

And when you have that opportunity sometimes it’s, like, the perfect time to do it and you just need to take it, right? And oftentimes you hear people saying, “I hate my job that’s why I left,” and then sometimes it’s just, like, there’s really nothing wrong with it but you have to take a risk and you take a chance.

And I love that that’s part of your story as well. 



And I think there’s a lot of ways they could do something like this, right? And sometimes there is that catalyst of, “I hate everything about what I’m doing. I’m just going to try something totally different.” And sometimes you just find the right moment for whatever energy you have into your passion and give it a shot. 

And I think that some things people don’t like to talk about in this industry and that is being supported in some way. 

And as much as I would like to say my husband works for me and we make all of this money, it’s not necessarily true. Like, I still struggle and I think that’s just being a freelancer for a lot of us. But having the support of a spouse: financial support and the emotional support of a spouse means a lot. 

And I don’t want to overlook that just because I do think that sometimes people think everybody does it on their own, and there are people that absolutely do but I don’t think that there’s any shame and having something to fall back on if it doesn’t work out. 


I actually really love that. 

You’re mentioning this because it isn’t. It isn’t talked enough about. You said this, Jess, it’s just people automatically think that because you’re doing a certain job or you show some things online, it just means that you have everything figured out, right? 

And it’s the same for a lot of people, it doesn’t come out right the first time, that’s why you do need that support.

And I love that you’re completely open and honest about that because it’s the truth. It just doesn’t happen overnight and you do need a lot of support whether it’s people that are a part of your team, your spouse, or partner, whoever it is that’s supporting you. Whether it’s just being there mentally with you or financially supporting you at all matters. 

And I definitely had that too when I first started with my husband. So yeah, I agree with that. 



It’s just amazing with the people that you surround yourself with and what that really does for whatever you do. I mean, if you work in an office and you have the best team in the world.

I worked at a Bath & Body Works on and off for seven years while I have a full-time job at a university just because I love the experience and I love the people that I worked with. 

And it just changes so much about what you can do and the energy that you do have. Whether you’re an introvert or an extrovert, you will feed off of the energy of the people that you’re around and similarly in the industry that you’re in.

And being in the travel industry, I have a lot of friends who are travel vloggers, travel YouTubers, and industry professionals, and they think it’s so important that whatever industry you go into, whatever kind of remote work that you do, that you remember that it shouldn’t be super lonely as far as like, learning and growing and networking.

You should have what I would call colleagues that you can talk shop with, and talk about trends with, gossip with, or whatever. Because those are the people who encourage me, they let me who might be paying for a campaign or who’s late on payments or who doesn’t pay.

Like, just having a circle of friends and colleagues is so important even if you work for yourself because you need that support and it will keep you in the loop of what’s going on. And as a bonus, it can bring opportunities that you just would not have had otherwise. 


And speaking about that, speaking about networking and having colleagues, it’s definitely important but it also can be really tough when you’re doing this as a solo entrepreneur. How are you able to get that community around you, Jess, when you moved and you started this new business, this new thing that you’re doing, right?

Do you have your website? Do you have your YouTube channel? How did you get all of these people to mastermind with? 


That’s a fantastic question because it’s something that I’m actually passionate about.

When I moved to Amsterdam, the first thing that I did, and I don’t really know how I knew this but I did maybe watching TV, is that you have to build a community no matter what you’re doing especially if you’re in a new place, you have to go to a community.

When you live and grow up in the same place, you haven’t built any community, right? Like, you have school, you have work,  you have your partner’s school and work and all this stuff. Your family, friends, high school friends. 

When you move to a new place or you start a new business, it’s a whole different group of people that you have to be involved with. And it’s kind of funny that the first thing that I did was join Yelp of all things.

I joined Yelp and I reached out to the community manager here. I don’t know why, I didn’t know what I was thinking about but I was like, “Hey, do you need any help with anything, please let me know.” And she replied, “Oh, welcome to Amsterdam. Let’s go for a coffee.” 

And she was one of my first Dutch friends. She actually convinced us to move to this neighborhood and that blossomed into meeting the Yelp Elites. These are people who love to be social and try new restaurants and stuff like that.

That helped us find the library which was a wine shop; that was a private kind of wine club. And then that blossomed, then you meet one person and then you meet their friends and you meet other people from parties and events. 

And so if you move to a new place, you just have to find something to get into whether it’s classes at the gym or language classes. Whether you or your partner has a job somewhere, like, meeting the colleagues and you always have to find at least one thing that you’re willing to put energy into because that multiplies into finding the people that are your people.

When it comes to the work stuff, like, when you’re working for yourself, I think it is so important to go to conferences – you just have to. And whether it’s conferences or meetups in town, you have to do something like that because that is going to be where you meet the people who need to be in your work network. 

I feel like there’s some sort of quote there, like, work and networking, the work into the network or something like that, I don’t know. But that’s how I found every single one of my blogger friends except one, they kept coming to Amsterdam and I DM them.

So that can be nice too, social media, but conferences I think would be number one, and talking to people on social media would be number two. 


It is so much easier when you’re doing it that way, especially when you’re not around anyone and then people are just traveling to either go to a conference or you do it online which is really great about your business and our business – we can pretty much do most of these things on the internet. 

And I do love how you place yourself in certain situations where you know you’re going to be surrounded by people who are either in your neighborhood and you know you can make new friends there or in your industry as well. Because it can be really tough when you’re doing this on your own. You don’t know anything about it and you’re kind of just lost when you’re beginning. 

So it’s always good to mastermind with different people when you are first beginning and even later on when you’ve been doing this for quite some time ’cause, like you said, you need help with every single stage that you’re in whether you’re a beginner or you’ve been doing this for a really long time. 



And I think once you get the hang of how to meet people, it gets a lot easier. And it’s amazing how one event can grow into. And it’s funny just how connections can happen, it could be so random.

At the time, my husband’s boss wanted to meet up after work for drinks. He brought his partner, John brought me, and then they brought this friend, her name is Shoshannah. She was an American who lives here in Amsterdam. She also happens to be a blogger that runs 

And so she started getting me press invites but it was all because my husband’s boss wanted to meet after work. Like, you never know when a connection is going to work out for you, whether it’s going to be your next best friend, it’s going to be your next business partner, or it’s going to get you your next job.


And I just see every opportunity as an opportunity to meet people and make that connection because you don’t have to like everybody, not everybody has to like you but if you don’t try to spend some time and meet people, then you could be missing out on great friendships or partnerships or colleagues. 


So what would you say to somebody who’s more of an introvert and they’re really afraid to do face to face time and that type of networking? I mean, have you always been this type of person, Jess, where you are just really open to meeting new people even going up to, like, a stranger? ‘Cause that’s one of the things that a lot of people are scared of.

And I think that’s why social media and social interactions are just a lot easier for people but I feel like you’re absolutely right that real-life connections can be so much more valuable in that sense. 


It’s funny that you asked that because I am an introvert and very much an introvert. But I value connection. 

I’d love to stay in my house and not see people. I mean, I probably shouldn’t say this but I rather enjoyed being home in the last two years as much as I had to be. But I value connections and I value relationships. And also there’s an element of, I think survival might be the wrong word but understanding of what you need to be happy, really. 

I mean, people, when they become expats, they tend to move away because they don’t have a community. And I knew that moving here, I had to build a community or else we would be very unhappy. We would be lonely, would be bored and it was the same thing when I started my business. 

So if you have the right mindset going into it, and I know it’s hard for some people, it’s absolutely hard for some people, I try to take it upon myself when I go to conferences to talk to new people because I know how intimidating it is.

I actually wrote a book about it. It’s like an ebook about it because, at my first conference, I went because I knew I would be intimidated. I knew I would be uncomfortable and I wanted to get the first one out of the way knowing I wouldn’t get anything from it except how to talk to people and just being in a group where everybody talks to each other. 

So, I don’t think it’s about being comfortable in every situation. It’s about knowing what you need to do to reach your objective, which is to make a circle of people around you that you can talk to, really.



And that’s really crucial for your success as well. So it’s kind of hard if you’re an introvert, especially if you’re doing a face-to-face meeting but it comes with practice and then all of a sudden you just become really comfortable, and then it becomes easier as time goes. 



And just find the opportunities that make sense for you, I think. Like, there are conferences for travel bloggers but some of them have press trips attached to them. And if you can get along with those transcripts, you’re in a smaller group of people where you’re going to be helping each other. You’re going to be observing each other. You’re going to be talking to each other.

And it’s like being forced into certain situations that are actually a very good thing as much as it’s really uncomfortable. And then you can come out with having the best of the people. 

And what’s really interesting in the travel industry, as far as friendships go, is you will have people who have been in it longer, more beginners and they’ll see it in different ways, different generations. 

I’ve been on press trips with more, like, Gen X, and I’ve been on press trips with Gen Z, and Millennial. And you’re always, like, meeting people and learning about how they see the world, how they see your industry but they like to focus on what they’re good at. 

I just paid somebody who takes Instagram reels much better than I do. And I just paid her for a consultation because I knew from a conference, we were in the same grouping, that she was really good at that. And it just kind of goes back to you’ll never know who you’re going to meet. 

And my favorite story, and I won’t name the person ‘cause I don’t know if she’ll get embarrassed, I was on a press trip, my husband and I were on a bus, and a blogger was telling another blogger what their niche was and it’s a very cute niche. 

And the older woman said something about, “Well, I wouldn’t like that,” or something; just really kind of dismissive. And this blogger said, “Well, then you’re not my ideal audience.” And it was really kind of cute because I was like, “Why is this older woman kind of bullying the younger blogger?” 

And my husband looked at me and he said, “You and her are gonna be best friends.” And we have been friends since then and that was 5-6 years ago, I lost track of time. But it was a bus ride, I hadn’t even talked to this person but there is this connection of just standing up for yourself really. 

And, yeah, I think I just keep repeating myself – you just never know.


But that’s true. You find your people, you find your people in these different weird extraordinary places sometimes that you never even knew because they’re similar to you in a lot of ways and you’re kind of attracted to certain things. 

And I love that. I love that you formed a friendship from the way she handled herself and the way you would also handle yourself when you do that. 



I would hope to, anyway.


She’s, like, your spirit animal or something.


Yeah. Exactly. 

It’s a personality thing that you’re just like, “That was really smart. You seem like a great person because of how you handle the situation.”


That’s awesome. I love it. 

So for you, Jess, when you created this business and now you’re doing it, you’re writing, you have your YouTube, how are you able to create income so that you can make this sustainable for yourself?


As far as creating content, there’s always going to be something to write about Amsterdam, about the Netherlands. I have taken many pivots. I think you have to be very aware of when something needs to change. 

And as far as being sustainable, right now, it’s just a matter of seeing what makes the most money as far as what I can reasonably do and what can be passive, and learning new skills to be able to get multiple income streams really is the key. 

So affiliate income is really big, YouTube ads, I don’t have ads on my website right now but there will be, just finding different ways to do that. And then also just finding the right clients really and knowing when you have something to offer that other people are willing to pay you for your expertise.

And then just growing that, just finding what works, building on that but then also pivoting when you feel like you have to ’cause during the pandemic, like, we didn’t really travel that much. We traveled a little bit when it was safer and numbers were down but I had to pivot a little bit more on the expat content just to be able to get the videos up to make YouTube ad revenue. 

So just seeing the opportunities of what people start asking you has been very important for me because people started asking more and more about life in Amsterdam so I started creating videos about life in Amsterdam. That kind of thing. 

Even if you have a small audience, they’re still going to be asking questions. And building on those questions is what’s going to help you grow and be a little bit more self-sustainable. 



And what made you decide to pivot towards YouTube? Because you have your website and then you added this new form of content for yourself.


I wasn’t doing well with the website, to be completely honest. My numbers stagnated and I was getting very frustrated. 

And one day around Christmas time, it was probably a couple of weeks before Christmas, my husband and I just started watching travel YouTubers. We started watching The Way Away and The Endless Adventure and I think Karen and Nate at the time. And we’re like, “Well, we travel. We could maybe do that.”

And I made a New Year’s resolution, I actually kept, very proud of myself, that we did a video a week for the year. And I think it was that year that I actually quit my job. And then I kept that going and I just saw it grow faster on YouTube. I saw community faster on YouTube. 

I could get paid on YouTube where there is, like, on Instagram and stuff like that, I have friends that have tens of thousands, hundreds of thousands of followers but how do you really get paid on that? Will you need campaigns? 

And I really wanted to be creating something where not only I like having the video from a trip, memories and all that. But the video was going to be the next big thing and it still is. And it’s still so important. And I saw so much potential on YouTube, with SEO, with brands wanting videos. And just being able to connect with my audience. 

And then the next year, I took a coaching course from a YouTuber that we started watching again, Cup of TJ, and I loved it. Just her point of view and everything that she taught, I found a renewed passion for it and a much better understanding of it. 

And so that’s why I’ve not only stuck with it but I feel like I will continue to grow with it. 


And that’s the most important thing – finding the right platform for you. For some people, it is their social, in terms of TikTok or maybe Instagram. It could be your website or YouTube. Sometimes it’s multiple platforms. So it’s great that you were able to find that for yourself. 

Now, do you see it translate at all? Now since you’ve been doing this for a bit of time, do you see any of your YouTube translating to your website at all if you point them towards your site?


I do try sometimes. It’s not so much though, really, but I try to do, like, a blog post with a video. So it might be if we take a trip to Belgium, let’s say Antwerp, I haven’t made the blog post yet but I’d like to have the companion pieces because different people absorb content in different ways. 

So my understanding of how this all works is that there will be some people on YouTube, it doesn’t necessarily translate into going from one to another because somebody might want to watch a vlog versus reading about it. But then if they just want, like, the places to eat in Amsterdam that I love, they’ll probably just go to the blog post. 

So I do see that they serve different needs. 


Yeah, absolutely. 

And again, it really depends on how people intake the information. 

I love that you have all these different types of things that you are doing too because it’s important to have that as well. And now you’re focusing on this and what you’re really passionate about ‘cause I think a lot of people tend to be, like, all over the place, and then nothing grows. 

Meanwhile, if you just focus on one thing, you can grow that and if you’re interested in another platform once you’re doing well or you have a good lead with one platform, then you can add another one instead of kind of spreading yourself out too thin as well. Because there’s definitely a difference when you’re on your own and when you do you have a team that could coordinate a lot more for you. So that would be helpful. But in the beginning, it’s a lot tougher to do that. 


Well, it’s hard ‘cause there’s just so many things.

And you go to conferences and people are saying, “Oh, but you have to do this and this.” And they’ll tell you to do five things but then at the same time will tell you, “Well, pick two.” And you’re like, “But how will I know? Where do I start?”

And I think the hardest part is when you’re starting out, start with what comes naturally and then you can always just go from there or see what you’re interested in and if you want to make that content.

But there’s just no right answer for every single person, like you said, you just have to find what works for you.



And even with me, we started with this podcast, and then when it started growing, I mean, I created the website just so that we can include the show notes and the transcriptions and we would have like a blog post here and there.

But we really started getting serious with our website, like, a year ago and we’ve had this podcast for almost four and a half years. And then this year we’re going to move into more, like, videos because we’ve established the podcast, the website, and now we’re moving on to a different platform.

But it takes a long time. You have to really create that brand. And then sometimes people follow you. And then a lot of times people just find you and then you create a new audience that serves that specific platform. 

So, it’s really important to just stick to one thing, get good at that, then add another thing. But yeah, it’s really overwhelming when you’re just starting out because you don’t know, there’s a lot of people that do well on a lot of different platforms. What they don’t tell you is that they started with one and then they added another thing and another thing, and then it moved on from there. 

So yeah, definitely confusing. 



And some people have teams, right? 




I think more people are being transparent about that. But there is a sense of when you go to some conference and stuff like that that it seems like some people are just a one-person show. A lot of times it isn’t. 

Just because it’s impossible to be on 5 different platforms and stay sane. To be good at 5 different platforms, they have people to help them translate whatever you are really good at and then disseminate that into the other platform.

I mean, there’s nothing wrong with that. I think that’s the best thing in the world because you’re reaching an audience that needs you and that’s what’s most important. It doesn’t really matter if you’re doing it by yourself because it’s a hustle culture. 

I think there’s a time and a place for it but in reality, as long as you can do what you do best and that’s what your audience is looking for, that’s what’s so important. 



And I honestly think delegation and having a whole team, I think everybody should do it at some point because, like you said, we can’t all do it at once, we can’t be everywhere at once. 

If I didn’t have my team, I wouldn’t be able to have all of these other platforms because I would just be stuck editing my audio, my podcast. I wouldn’t be able to write any content, I wouldn’t be able to create videos. Like, it just would not be possible to do that. 

So yeah, I think, at some point in your entrepreneurial career, having a team is essential, it’s not even like, “Oh, maybe,” it’s going to be essential otherwise. You’re going to get burnt out, you’re not going to do everything, and it’s not going to be beneficial for you. It’s also not going to be enjoyable in the long run.

And also another great thing about having a team is that you can put the task that you really don’t like to do to somebody else that most likely will enjoy it.


Yeah. Exactly.

I’ve been that person for somebody else and it was quite enjoyable to be part of their success. Like, I’m behind the scenes but I love doing what I was doing to help you get to where you are, that kind of a thing. And that’s a really good feeling too. 



And that type of thing is really crucial. And it’s great to get to that point but I love that.

Well, for you, Jessica, looking at everything that you’re doing now, let’s move forward to about 30 to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


I would love to be remembered for just helping people. 

It’s a lot harder to help and maybe the way that I was doing when I was in the US because of the language barrier, which was more, like public safety and stuff. But I would just like to be remembered for helping people that need help in whatever small way that I can do that. 

It could be helping them see Amsterdam the way I see it through my eyes outside of the touristy things. It could be helping a blogger, being their Mentor. It could be inspiring somebody to take the leap to work for an international company so they can move abroad. 

But anyway I can just help if I could be remembered for being that person, then I feel like I did my life the way that I wish I did. 


I love that. 

That’s such a great legacy to leave and always finding somewhere where you can find yourself useful, and help other people is a great way to live your life. And I love that you’re making that into your legacy, Jessica. 

Thank you so much for sharing your story with us today. We really appreciate you.


This has been so much fun.

And I’m so glad that I had the opportunity. Thank you so much for inviting me.



So if our listeners want to learn more about you, where can they find you? 


YouTube is probably best for long-form videos, which is just, But I’m on Instagram a lot, on stories, and I’m getting better at reels.

So those are the two main places but of course, my website is always there for some quick information.



Thank you so much, Jessica. We really appreciate you. 


Thank you so much. 

Listen to Jessica’s extended interview where she shares how to relocate to the Netherlands as American remote workers and digital nomads.

What you’ll find:

In this episode, Jessica will help you relocate to the Netherlands as an American remote worker.

Follow Jessica:

Show Credits:

Audio Engineer: Ben Smith

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