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Meet Digital Nomad Taylor Wallace who has been a full time nomad since 2017. I met Taylor in my Medellin coworking space in 2022, we got to chatting and I loved her story so much I asked if she would be part of my Nomads of the World series.

Q: What kind of traveler are you?

Taylor: I would define my digital nomad style, as a slow-mad. Meaning, I like to stay in one place at least three months. Sometimes up to six, kind of as a function of where I am, what the weather’s like, how the waves are, important, things like that.

Q: How do you pick a nomad destination?

Taylor: I’m coming into my fourth year of digital nomading. So when I was younger and more autonomous in my job, it was kind of just like what place just like looked the coolest, you know, or like some thing that just had always been on my “one day, some day” list and realized like, why does it have to be some day? It could be next week.

So I think early on, I mean, it was always important to prioritize like places where there was what I would call like the “tribe”, which is basically like-minded people. So other entrepreneurs, people who are, socially conscious and, you know, not just a group of Americans, like living together in this country and only hanging out with each other and only speaking English, like people who are interested in getting the full experience of living abroad.

Early on I was much more kind of flexible and free. Now that I’ve gotten older, I think I kind of have like a list of non-negotiables when it comes to deciding where I’m gonna be. Like time zones are super important. With my job, I do have a bit of flexibility, but I need to like give adequate consideration on the front end of like, “Okay, If I’m gonna be six hours ahead of my team. Like what is that gonna look like? Do I have the energy and motivation to be waking up at this time and going sleep at this time?”

And sometimes the answer is absolutely not. But for some destinations it’s like, yeah, I’ll gladly go nocturnal just to have this experience.

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Q: How did you get started nomading?

Taylor: The decision to start and nomading was kind of a weirdly logical one. I started my first company back in 2016, living in Boston at the time and we got accepted into a business accelerator that was based out of New York. So I moved to New York, going through this accelerator, just the hustle and grind, hustle and grind of not only the startup ecosystem, but that time in Manhattan, it’s just a lot.

And so we finally graduated from our accelerator program and at that point pretty much my entire team was remote, except for our creative director who lived in the city. As I started looking at potential new apartments moving back to Boston and moving back to New York, like a lot had changed. Because when I started my business, I still had my corporate job and was working on my business on the side. And now here am working on my business full time, solopreneur looking at, you know, $2,100 for a studio like, are you kidding me?

And I was fortunate enough that like my parents have always reminded my siblings and I that the US is not the center of the world. So we traveled a lot as kids and really got to experience a lot of different cultures and communities.

For me I knew it wasn’t a question of comfort like I think maybe it is for most people, it was more so a question of like,”is this the best move for my business? Like what are the trade offs that I maybe can’t see and being in, running a startup.” Being beholden to not just myself, but you know, investors and stakeholders and stuff like really having to actually take time and do some research and like present to this board, like why I should be allowed to go, which is what I think a lot of employees probably would have to do.

But I think that was kind of unique to being an entrepreneur, but still all having to prove that I could run my business abroad even though it made absolutely no difference. Basically once I got the begrudging nod of approval, I was just ready to go.

Being a digital nomad isn’t easy, but it’s a lot easier than most people think, or it’s a lot more attainable than most people think. Both financially, logistically, professionally.

-Taylor Wallace

Q: What are your strategies for balancing work and travel?

Taylor: The strategies that I have were definitely acquired through like trial and error. When you are someone like myself who genuinely loves what you do, it can be really hard to set boundaries.

A lot of the times when you are home, wherever home is for you, you have certain infrastructure that’s in place that you don’t even realize is there. So whether that’s like your group of friends that get together for a happy hour at whatever frequency throughout the week, or you know, you’ve got like your gym or you’ve got your puppy, or you’ve got your call with your mom every day, you have all these things that you don’t realize kind of make up your normal.

And so when you move to a new place, like all that’s gone.

And if you don’t take the time to, one acknowledge that and then two kind of consciously rebuild those foundations in whatever way necessary. You can really spin out pretty quickly.

Actually I wrote an article about the concept of the traveler’s depression, where like basically you are in a new city, it’s beautiful, new people, new food, like you’re so stimulated, you feel so happy, you know, cuz you’re just constantly reacting to all of these new things, but after a while things stop being so new and it’s just another day.

For me, I know the things that bring me joy, you know, when it comes to like the activities that when I’m having a really sh**ty day or when I just need to reset or whatever.

Don’t let the bad habits from home follow you, but don’t lose track of the good habits from home. Just being really intentional with how you structure your lifestyle and this new environment.

black woman is outside and smiling at the camera wearing a sweatshirt that says "be a nice human"

Q: What are your favorite nomad cities and why?

Taylor: My three homes are, Chiang Mai in Thailand, Lisbon, Portugal and Medellin, Colombia.

What I really liked about Chiang Mai just was the pace of life. I liked that it was a Buddhist country and you could really feel it. People were very warm. I really loved going to monk chats every Wednesday, where I could just like ask all of my existential questions about life to these monks, and the purpose is basically to help the monks improve their English. It’s just a solid, nomadic community. And it’s just like a really quality place, like get to know yourself better and grow as a person and professionally. I could go on, I mean, it’s just an awesome place.

Lisbon of course, I’m half Brazilian, so I speak Portuguese. So that’s a big factor being able to communicate. Portugal has some of the best waves in the world. One of the most famous drop zones in the world, cost of living is really reasonable, but you still have the stability of the Euro. I have mixed feelings about nomading in Europe. I just, I don’t know, it didn’t really click for me, but when I was in Lisbon, it really felt like home. Food was bomb, everyone’s kind, you get really nice bottle of wine for two Euro. There’s really like a solid up and coming, entrepreneurial ecosystem there as well. So like tons of meetups, like tons of conferences and things like that. And that was really attractive.

And then lastly being here in Medellin. Colombia is a beautiful country. Medellin, the city of eternal spring. So I love like, energetically, I feel like the, the climate and the environment here is really complimentary to me. It’s not all about the cost. Sometimes people will think that money is the most important thing when in reality it’s safety. So I know I’m very comfortable here because I’ve lived here in different capacities even before nomading. But being able to kind of see the evolution of not just the city, but the country has been really, personally fulfilling for me.

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Q: What advice do you have for aspiring Digital Nomads?

Taylor: Simple as it is. Like if it’s something that you want to do or something that you wanna try, like just do it. There’s always gonna be a million reasons to not do something.

I think a lot of us live our lives in one of two modes, like either this autopilot and this is how it’s been, this is how it is, and therefore this is how it always has to be. We don’t even allow ourselves to consider that there is an alternative.

And then once you kind of have that awakening, whether you see it on Instagram or you see a YouTube vlogger and it just looks so beautiful, luxurious and like unattainable you’re like, “okay, well, like that’s their life. There’s no way that I could, like I’m not an Instagram model or I don’t know how to do cool effects on a Adobe premiere. How could this be my reality?”

And the answer is it’s not about what everyone else is doing. Like if you take the time and get clear on what it is that you want to do, whether it’s like, “Yo, I just need a break.” I’m gonna take a sabbatical and you just wanna take a year and travel. Like, that’s cool. Like, it doesn’t have to be these like rigid definitions of like, okay, I’m gonna sell my house and like sell all my stuff and like give my dog to my grandma and like I’m going on the road.

You could do that if that’s, your vibe. But I think that, again, going back to the fact that the journey is just that it’s a journey and it it’s your journey. So I think once you have clarity about around, what’s important to you, you can start like reverse engineering and like how to make it happen.

And you’ll always look back and say, you know what, I tried it. I gave it a go and it wasn’t for me, but now there’s no one to blame. There’s no hypothetical. I made the decision that this is not something I want to do.

Or you go and you realize it’s freaking awesome. I have some friends that left on a one month, nomading trip like three years ago and just never came home. So again, everyone’s journey is their own. There’s no right or wrong way to do it. Like it all starts to just making the decision.

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Q: Is being a Digital Nomad easy?

Taylor: Being a digital nomad isn’t easy, I guess it’s a very relative term, but it’s a lot easier than I think most people think, or it’s a lot more attainable than most people think. Both financially, logistically, professionally.

So I guess if you’re someone that’s considering becoming a digital nomad, I would encourage you to maybe do a little like free writing exercise and maybe just see what pops up, like three minutes or five minutes, and just write down all of the things that you think you know about digital nomading or the fears that you have about becoming a digital nomad or the reasons why you think you can’t.

Just really do like a brain dump to maybe get a little bit more clear on what limiting beliefs you might have, if any. I find that that’s a really practical way to disassemble or unpack, some of the things that might be standing in our way, when it comes to doing the things that we decide that we want to do.

So taking your hypothetical fears and like actually getting them down on paper and like going through them one by one and like actually fact checking yourself. And I think that really helps with the process of like building confidence that like this is something that you can do. It’s something that anyone can do once they make the decision.

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