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Ep. 325: How This Couple Travels The World As Nomad Business Mentors with Anastasia and Tomer

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In this episode, I speak with Anastasia and Tomer who left their lucrative 6-figure corporate careers to embark on their offbeat life adventure. 

Building on their prior experience as mentors they created Generation Nomads. Their mission is to help fellow travel enthusiasts start an online business that allows them to work from anywhere, with just a laptop and a suitcase. 

Today, they are full-fledged digital nomad entrepreneurs and have helped over 25 freedom entrepreneurs turn their skills into digital products or services they are excited about. 

Listen to find out how Anastasia and Tomer have created a free lifestyle as remote business mentors.

Listen Below:


Ep. 323: How This Former Software Developer Pivoted To Become An Online Personal Trainer with Joe Müller
Ep. 322: How This Writer Created A Profitable Business Through Ghostwriting with Stacy Ennis
Ep. 320: How This Content Manager Became A Digital Nomad with Sarah Blinco


Hey, everyone! Thank you so much for being here!

I am really excited to speak with my guest today, I’m here with Anastasia and Tomer.

Hi! Anastasia and Tomer!

Anastasia & Tomer:
Hi, Debbie! So nice to be here.


Thank you so much for being here, I’m really excited to talk to you both before we get to everything that you’re going to tell us about your journey, can you tell us a little bit more about you and why you live an offbeat life?

For sure.

So we’re Anastasia and Tomer and we’re travel lovers, obviously, um and our journey with the offbeat life started because we had this vision that we wanted to create this perfect definition of our life and that would be waking up seeing the ocean and palm trees and taking slow mornings.

Um, but also being excited about the work that we do so kind of the freedom location but also creativity and just not draining Mondays, but looking forward to them.

Um, right to being able to travel and that’s kind of the vision that pushed us over the last couple of years to build our vision of an offbeat life and a business that is supporting that.

So what we’re doing right now is we’re digital nomad business coaches.

We love slow travel. So, we love basing ourselves from beautiful locations and working and living there for a while, returning to our home base and then picking the next destination.

Um, and just creating a life that we don’t want to take a vacation from. So, basically, this is not something that we really grew up with believing or just decided to you know, or mostly even our upbringing like from parents.

My parents are from communist Russia so I um, what I moved to Germany when I was really small and following your passion was not really a thing so I was raised very strictly with a lot of attention to school and just you know creating a very good career having a good degree and just I was building my life for my CV, so to say, like really for my resume.

Until at some point I was just asking, “Okay, what am I doing this for?”, right? or “For who am I doing this?”, um and we’re just so passionate about the work that we do, so really helping others also to create this offbeat life because that was us five years ago and um, five years ago our life was basically looking perfect on paper, right? Like, lucrative 6 figure careers, an apartment in the heart of Amsterdam, we actually met during our and MBA studies and I personally was ah working back then in corporate and a Fortune 500 company.

And I just recently got an excellence award as the youngest business developer, um responsible for really big visibility project and it was at the celebratory ceremony where I was handed over the award with you know, a lot of the c-suite people there that I just realized, this award means really nothing to me and that it created this life that really looked successful based on you know, society’s definition, but that was not my definition of success and I just wanted to travel full time and Tomer and I, we had that already on our bucket list, but it was just something that was moving further and further down on that bucket list and we just you know thought, “Okay, spiraling down into burnout. We have to take the plug and just finally make it happen.”. So I quit my job cold turkey and Tomer, went and he agreed on a sabbatical from his employer and that’s how we started to travel full time.

Um, yeah, yeah, go ahead, Tomer.

I just wanted to to continue basically about our travel ah time because that was really a turning point for us. So, when we left our jobs and decided we’re gonna just go travel full time, ah we set out without really having a specific plan, but we knew we want to turn our life around.

We knew we want to now take this time to see different places see different countries. We visited over 25 countries in eighteen months, traveling full time and we set ourselves with kind of not really a goal but more an idea of let’s explore our passions, let’s think of what are things that we ah that we could do and we did different things we um, started ah interviewing influencers on Instagram for our book.

We ah created a blog, firstly documenting our travels and then moving into other topics that sell the same blog that we have today.

So, it’s ah the topics have evolved over time. Um, and we also yes that we we started really? ah. Also working with affiliates so we were trying, we were really experimenting with different items for example with affiliates.

We worked together with a company who rents tuktuks in Sri Lanka and ah yeah we did a collaboration with them where we made pictures that they could use ah for their marketing campaigns, in exchange for using ah or for driving the tuktuk around for one month and additionally we also wrote a blog post about this and we are, till this very day, we’re affiliates with them and people are still ah from our blog going and renting out the tuktuk in Sri Lanka.

So, some of those things, ah, we’re yeah more successful. But yeah, we just really experiment with different things. Um, but our goal was really to achieve ah financial freedom for ourselves and to really focus on our passions ah in order to, like Anastasia said just before, not to have to take a vacation from ah from our life.

Yeah, it’s it’s really interesting. Um, because one of the things that you were talking about Anastasia, is that a lot of us, I mean not just you, and I’ve talked to so many people on my podcast writing it seems like there’s this common theme where everyone is just chasing something that they don’t even want right? It’s what society tells us that we should want and we keep chasing it and we’re always wondering why we’re still unhappy, even though we’re achieving and we’re getting better and better pay, we’re getting better and better positions in business or whatever field you’re in but you keep getting unhappier, because you keep thinking that you’re going to be happier as you get more money, as you get more positions, and it doesn’t happen that way.

Once you take a risk and actually do something that you’re interested in or it’s gonna give you more freedom to actually do what you want, everything shifts and I know that you realize that and it’s such a pivotal moment in your life, where you are getting all of these recognitions but you realize you didn’t want it, how did you decide – was it at that moment you both knew, like you talked to each other, “Hey, we’re going to do this.”, or was it kind of a harder thing for you to take that risk, to leave something that was stable to do something that you both have never done before?

Yeah, that is a great question because I think that’s something that people are wondering about, really, “Okay, if I have this dream, this pipeline dream, is it something that I really need to work towards? Or am I just jumping into the cold water?”, right?

And for us I think it’s been also something that has been building up over time that we had this crazy idea, we wanted to go travel full time and I think it was born, this idea, right after our graduation from our MBA that we did together.

We went traveling to Southeast Asia for five weeks and it was the first time that we were in that corner of the world and we just felt for the first time the sense of freedom and traveling and exploring totally different cultures to our own and it was back then I remember um, sitting in a cafe in Vietnam, in Sapa and it was raining outside and we were just ah listening to this really cool music and it was a very um, fun cafe and drinking our drink and we were saying, “You know what? It would be so cool if we could do this more.”, and at that point it was actually before starting corporate, I already had my corporate job lined up and I knew in a couple of weeks I’m going to start this career, so this idea was born I would say back then but then as you said, you know, life happened and you chase 1 promotion after the other.

And I think at some point for us. The realization came that you know now I’m working ten hours a day and commuting 2 hours to work in order to chase a promotion that will make me work 12 hours a day.

So is that really the definition of happiness? And how I want my life to look like? And I think for me personally, it was in the moment that I just ah realized that I was getting increasingly overwhelmed with kind of you know, sticking to this lifestyle that I really didn’t want, and burnout took over and that’s when we really started talking about it seriously, right?

Yeah, that’s ah I think like that’s from Anastasia’s side and from my side I think like what you mentioned interestingly is, ah yeah about taking the risk as well because um, that is something that we’re very conscious about, so I’m rather ah, logical and very practical thinking, this is why I always, when I go into something I’m immediately thinking of all, even the nitty gritty details, of you know what we’re going to do or you know, just random things like this, you know, but it’s also just having, I think at some point we both kind of that realization as well that, “If not now, then when?”, and also about that we’re actually living our Plan B life, so to speak, so the safe part, having the safety net, like having a job and a salary coming in every month, yeah, it gives you a sense of security but it’s not really the life that we want to have or is the Plan B, of not pursuing our dreams and taking the risk which will be done in that case Plan A.

That realization was also very important I think, when we started talking about this like, “Okay, it’s we just have to take the risk in order to make that.”, it’s like taking a leap basically into your – the life that you really desire.

Yeah, and and also going into that more I think before we even know what being a digital nomad is being a remote worker because like you mentioned earlier, Anastasia, like, nobody knew this lifestyle we didn’t grow up with this lifestyle.

This is pretty brand new, I mean, I’ve talked to people that have been doing this for like 10 years or even longer, but that was a very few, like very few people could do this because working remotely was not a thing until, like just a few years ago, just a little bit before covid hit, right? And we didn’t know that you can also combine both where you can have more flexibility have more freedom and not be stationed in one position, not hate your job completely, you know? Even if it’s like not your dream job at least you would had more freedom with your time because then you could still travel while you’re doing this and you don’t feel so confined and like a prisoner in one spot and I think that’s really what we’re learning now too, is that you don’t have to choose between one or the other, you can still have stability in terms of what you guys are doing where you created your own business making income from this or you can be a remote worker and still travel the world or even if you don’t want to do that, you can stay put, but spend as much time with your family, do other hobbies and actually have a life outside of work.

Absolutely, I think you’re yeah, you’re talking to a really important point and that I feel like it starts with asking yourself actively, “How do you want your offbeat life to look like?”, right? I feel like we’re seeing ourselves so often inside this box and kind of under this identity that we created ourselves with our job title, so it’s like what is written on our business card becomes then the boundaries of what is possible for you and what we’re saying and what we have now come to realize ourselves and what we’re working on now in our business and with clients, is kind of breaking those barriers of not looking only into your options but really looking into your desires, like you can create a different narrative.

You can create a different identity for yourself, but the first step is really becoming clear about what that looks like for you and as you just mentioned there are so many different ways to make it happen and it all starts with what is really important to you, what are your values? Do you want to use the skills that you’ve developed in a 9 to 5 that you’re currently unhappy in to, you know, go either into remote work or starting your own business? Or do you really want to allow yourself to give that freedom to explore something new and just to know that you don’t need to have the perfect plan starting out, but you just need to take the first step and then so many pieces will fall into place once you start walking, but you need to start walking.

Yeah, absolutely and I love that there’s like a yin and yang between the both of you, because um, you know, Tomer is very analytical, he’ll like think about, “Hey, how is this going to work?”, and then, Anastasia, I mean correct me if I’m wrong, you’re more like the idea person, seeing the big picture and I love that that you have that combination within each other, because like my husband and I are the same way, I’ll like think about all of these ideas and he’ll be like, “Hold on, let’s slow down a little bit, like let’s think about how this could actually happen before we do anything.”.

Yeah, exactly, yeah and I think what is really interesting too, is that we just had a conversation about this the other day, because we, somebody was saying to us the other day, you know, “I’m a dreamer while my husband is like the realist.”. So, ah, you know, kind of ah he is not really for it, it was about starting a business and then this lady she was really wanting to go into that and her husband was a bit more, she described him as a realist and then we started, Tomer and I, discussing about that fact and Tomer brought up actually a really good point about being a realist.

Yeah, so it was ah a thing where we started, we brought in the conversation a bit, we started talking about also being an optimist or a pessimist and you know that many people say in between you have the realist. Um, but what we thought about is, you create your own reality.

So, whatever you choose to be real for yourself is what your reality is going to look like. So being a realist is yeah the question is like, are you being pessimistic about what your life could be? Or are you being optimistic? And when you’re being optimistic about what your life could look like and what it could be, then that becomes your reality.

It’s about taking basically calculated risks, right? Even if you are looking into creating a safety in a you know, in a path that seems like wild and and extraordinary and just something totally out of the norm.

It’s asking yourself, “Okay, how can I do this?”, in a really experimental way and you know, taking calculated risks, so, I think that’s what it  means.

It doesn’t mean immediately, so if you want to change something, it doesn’t mean immediately that you have to go one eighty and drop everything that you know, ah for another life or for another reality just to continue in the terms where we were talking about, but you can change it bit by bit as well and like Anastasia was saying it’s really about taking the first ah steps and proving to yourself that you can make progress in that direction of the life that you really want to have.

Yeah, I think that’s such a great point because if you’re more of a person who is very analytical, it’s harder for you to to go into the other side, right? In the dark side, because then you you think about so many things, how things are going to go, all the different parts of it and then if you’re the you know the idea person or you’re the dreamer you just jump into it without thinking, most of the time and obviously there’s risks involved in that if you’re the realist, it’s the risk of never doing anything and never trying anything because you’re always thinking about it but never actually taking action, and if you’re a dreamer and you just keep doing, sometimes there’s really no rhyme or reason for anything.

And it takes so long. But I do have to say like one of the things that I do admire about the dreamers is that at least they take action. Um, it’s a lot of mistakes, but at least are doing something and the things that I admire about the realist is that they’re so calculating with the things that like they think about and everything and I’m like, it’s good to have a balance.

Um, yeah, definitely I think this is something maybe one of the um ah benefits also coming from let’s say ah or corporates career and I used to work as a go-to Marketing Strategist, you know releasing new products to the market and health technology and I was surrounded by scientists a lot.

So, my you know dreamer and kind of let’s do this mentality was hitting them, you know, the very calculated scientists that wanted to do things like very much, hypothesis-based and I think that’s something that we also then took on a little bit in a very, you know, in the most positive way into our, how we do our own business but also how we do business ,you know, with clients because speaking to you know what we were just talking about like, you know, combining the doer mentality with actually taking some calculated steps and doing things in reason, you know, it’s a lot about just experimentation in a structured way and just learning from what works. Um, and improving on that.

So basically not seeing that you either hit or miss. But that it’s actually a journey and as long as you keep on walking on that journey and try to figure it out and continue you will get there eventually.

And also just to add on that because taking those steps and doing these kind of experiments which don’t have to be huge, again like you don’t have to just drop everything, but taking the first steps means that you start gaining confidence about moving to, yeah the the life that you want if you want to start your own online business so that you can work from anywhere just as an example is that what the main thing that comes into my mind right now.

Um it doesn’t have to be like immediately quit your job. Ah, you know, I don’t know, buy a domain, start a website, do all kinds of subscriptions to things or whatever. It doesn’t have to be all that at once but it can be just taking the first step and then the second step and then the third step and through doing that you will start getting confidence about your idea and that will make it also more real. Um, yeah, so I think that’s really like a very important piece, yeah piece of advice that I would like to give.

Yeah, and and also for for people who are really afraid or maybe you have more responsibilities in your life, um, one of the things that you can definitely do is, while you’re still in your full time job, um, like you mentioned Tomer, just start something while you’re doing that, right? Um take the time maybe during the weekend or after work. It doesn’t have to be a lot of time. Um, but just put you know, put your finger in it and then see what happens, pivot and at least you’re not taking away, um, your whole income and just putting everything on the line and on the risk and then you can see from there whether it’s what you want to do and you can always pivot and do do other things but I love that idea of just doing things a little bit at a time because you’re doing a best of both your, you’re trying something but you’re also being cautious about it. Um, and and that’s another thing too and you you talked about this a little bit, Tomer, as like being optimistic or being pessimistic and nothing in life is perfect.

There’s always going to be failures. Things are not going to work out the way you want it to most of the time and if it does oh my goodness, you’re a lucky person. Um, because there’s you know life is always an up and down thing and we all know this right? There’s always going to be those hills we have to climb and there’s going to be things that just not going to go in our way but um and I think you know for, for me going through this whole process is just seeing, what’s good that comes from from all of this right? Because you always learn something from the bad things or you know there’s always learning lessons that come along with it and you’re always seeing, “Okay, well that didn’t work out. We’ll pivot and do something else.”.


Yeah, exactly. I think it’s also part of like just changing the mentality of like thinking that life doesn’t happen to you but it happens for you like I really like that, I always try to think that way, so out of every situation like you mentioned is to think, “What’s in it for me here?”, like, “Why did this happen and how can I build on this in my benefit?”.

Absolutely, and obviously, you guys have have been doing this together, has there been any um conflicts between your ideas that you had to work out because you know it’s already hard enough if you’re doing this solo, but with a partner, I know I’ve done this with my husband and I’m like there’s just times where you butt heads.

Oh, I’m, yeah I’m sure we had like countless moments of those and I do have to say, we, despite all of that we still enjoy working together and especially going, that was before corona, right? When before covid that so many of us were just forced to spend so much time, more time with this significant other like we did that long, long before covid, that we went traveling ah together and spent really 24/7 together and people kept asking us, “How do you do that and then how do you do that while running a business?”, and actually something we didn’t talk about yet is, we have now a one year old, we just celebrated her birthday, so now we became another kind of shared responsibility together is parenting. Um, so I think of course there were moments where we were bumping heads, I think what is really important is just being able to kind of switch the work mode off, right? Kind of again sitting down at dinner and enjoying the dinner as a family rather than you know, discussing kind of what came up during the day and discussing strategy and stuff like that.

And I think that’s kind of the main point of just trying to being able to switch the hats.

Yeah, and also it’s probably easier to do that when you have a child because they they’re like, “Okay you need to, you know, pay attention to me now.”,

Anastasia & Tomer:
Um, yeah.

We need to do something because we can’t just be here working all day.

Yeah, I think so, one thing that we realized very early and that was when we just started traveling full time is that both of us had to figure out how we like to operate like just individually because what we realized is that traveling full term full time together was definitely different than just going on vacation together right?

When you’re going on vacation, you typically have the same goals of, “Okay, I want to enjoy and see as much as possible.”, and you kind of go with a similar mindset, I feel like because you’re planning the vacation before.

And now suddenly you find yourself traveling full time and this becomes your new lifestyle and we just ran into that problem, you could say that, Tomer, he was more the like, “Go, go, go.”, and he wanted to see everything and do everything on the bucket list and I was more like, “I just want to, you know, chill and have some time.”, and I think naturally I am more of an introvert, where Tomer is more of an extrovert in terms of where we get our energy from, so I really need my downtime and my alone time, so that was something we had to figure out like for the first time, like how do we actually like to spend our time and then finding a way to really create kind of this way forward that works for the both of us.

Yeah, that’s really important to do because then it gives you a lot of balance and space with each other, it avoids conflicts and annoyances that does happen when when you’re with somebody all the time, cause that could be very difficult sometimes, but yeah you guys survived the the covid era, you still can stand each other, this is going strong. It’s going all the way for sure. So.

The couples that travel together, stay together, right?

Exactly! And they do business together, they have a child together, they went through the pandemic together. You guys are good, everything is gonna be good.

Um, we did it all.


Well, before you go, I do have a question for both of you, let’s move forward to about let’s say 30 to 40 years from now, what would you say when you look back in your life is your legacy and what do you want to be remembered for?

That’s a very nice question actually, because it’s something that I do think about quite a lot and we also discuss it amongst each other quite often. Um I think we have it I think it’s similar for the both of us.

Um, and it’s really, leaving an imprint on people that were like us, five years ago, so that’s people that are like I mentioned earlier like living their Plan B life.

So, keeping it at the moment safe just you know, making sure that they have their salary and feeling like they want to do something else, having this passion this burning desire to live a different life but not yet making it, so to help as many people like that to make the transformation and transition to live their best life and by that also yeah, what we’re specifically doing is to help people to set up their business so create an offer and with that I think it kind of propels even further because when they create a business and an offer then we are even touching than more people because they do something that they’re passionate about and that they’re happy about and that helps other people and in that way kind of propelling it further to the entire world, I think that something that we would be very yeah happy to to leave as a legacy behind.

I think when I think about how I would love people to remember me, I just want to kind of have this um reputation almost or you know I went to people to look at us and really say you know, “Those 2, like they try to do things, they try to go offbeat and do things differently and they showed that you can just figure out a way to do that.”.

So I would love to if people you know, remember from us that you don’t exclude the possibility. So just give yourself the gift of exploration and of allowing yourself to look into different options and not exclude them right from the beginning just because you don’t know how to make it happen just start with the why of why you wanted what you want and then the how will fall in place and I think that speaks to what Tomer was saying, helping people like really tangibly to make that happen.

Yeah, absolutely and I think for for the most part too, we are our biggest enemy in that, right? Because we talk ourselves out of good ideas, really good ideas and I think somebody said this one time, it’s like I can’t even imagine like, how many great ideas were killed because you know, we we talked ourselves out of it and we didn’t actually share it, so that is pretty incredible that you guys are already building your legacy right now and then went, you know, you have a child and then that could be passed down to them and that’s an even bigger legacy because it’s generation to generation, I think it’s pretty incredible that you’re both doing that.

Thank you so much for being here and sharing your story with us and your journey if our listeners want to learn more about you work and they find you?

Yeah, absolutely we love connecting with ah people on Instagram so if you’ve been listening to this and you want to stay in touch and say hi and maybe share what your offbeat life looks like or if you want, if you’re curious to look into that direction of figuring out, “Okay, how can you take your passion or your skills to the next level?”, and look into creating, you know, a freedom-based business for yourself then we would love if you DM us on Instagram.

If you want you can use the word “offbeat life” and we’ll be happy to share a free resource for you on how you can get started with the first steps.

Perfect! Thank you so much and Anastasia and Tomer, we really appreciate you and sharing all of this with us.

Anastasia & Tomer:
Thank you!

We are so happy to be here!

Thanks for having us, Debbie.

Listen to Anastasia and Tomer’s extended interview where they talk about how to select the right skills to turn into a remote business.

What you’ll find:

In this episode, Anastasia and Tomer talks to us about choosing the right skills to turn into a profitable remote business.

Follow Anastasia and Tomer:

Show Credits:

Audio Engineer: Ben Smith

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