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In this episode, I speak with Elina who is a digital nomad and travel hacker from NYC. 

Elina works at a personal finance company based out of San Francisco as a Travel Rewards writer and has a coaching business where she teaches women how to travel the world in luxury on miles and points for next to nothing. 

Listen on to find out how Elina uses her travel hacking skills to see the world. 

Listen Below:

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My Offbeat Journey: Stop living up to other people’s expectations and start living the right lifestyle for YOU!

Transcription:

Debbie:

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

Hey Elina, how are you? 

Elina:

Hey, I’m good. How are you? Thank you for having me. 

Debbie:

Thank you so much for being here. It was so exciting to talk to you. Elina and I actually met on Clubhouse and she has such an interesting journey and story on how she became a digital nomad. And I wanted her to be here to share with us all of her crazy, crazy life turns and how she got to where she is. 

So Elina, can you tell us about you and why you live an offbeat life?

Elina:

I was born in Russia. I moved to New York with my mom when I was eight. My mom was a single mom and growing up in New York, I definitely felt like there was this big focus on having to be successful. My family, of course, we’re like, “When you go to college you have to pick a job: doctor, lawyer, or finance.” I never really thought for myself.

So I kind of just went into finance blindly because I was good enough and I thought, “Okay, well this is the career I’m going to take.” I became a CPA, I was working in a big accounting firm and then I just realized I didn’t like it.

So then I went into finance and then to banking thinking maybe I was going to be happier and I just wasn’t. On paper, everything looks perfect. And I was living this lifestyle and living in a great apartment in Manhattan and I had all the material things I could want but inside I wasn’t happy. I didn’t care about climbing the corporate ladder. 

And I wanted to change my life but I didn’t know how. I did what a lot of people who live in New York, want to quit their job but don’t know how to do it. I just decided, “Okay, I’m going to go back to school.” 

And instead of just selling all my stuff, quitting my job, getting rid of my apartment, and traveling the world, I just said, “Okay. Well, I’m just going to study for the GMS and go to a grad school so that I could have that experience that way but also still be able to improve my resume just in case I ever wanted to go back to finance, I totally could.” 

And I just realized now when I look back, I’m like, “Okay, I didn’t need to go to school to do that.” But at the time that’s kind of like how I felt. Like, I had to justify to myself, which is actually kind of unfortunate that I just didn’t want to, like, “just take that chance. 

But anyway, I decided to go back to school. I moved to London. I went to LSC for my Master’s. And when I was in London, I went to Nomadic Cruise, it’s a conference for people who want to be entrepreneurs and digital nomads. 

And I came across a huge community of people who work remotely, who have their own businesses, who just travel the world while making money. And I was just overwhelmed thinking like, “Oh my God, this is amazing. I don’t have to just stay in London or go back to New York. I could live anywhere.” 

And now I have this huge community of people that I know all around the world that are doing this, that I can go to for advice, for inspiration, whatever. After that, it basically kind of coincided with all my exams ending. I gave up my apartment and I just started traveling the world after graduation instead of looking for a job. 

Actually, I had a job that I turned down in London and I just said, “Okay, I’m just going to travel the world and see what happens.” And at that point, I was just kind of like living in South America, had a community of friends around me all those who are dead remotely.

And during that time, it was just like the first time I ever had that kind of freedom in my schedule where I could just be creative and explore. It’s just something that I always wanted. So during that time, I started freelancing using my hobby which is travel hacking.

So I started doing that and making some money. I also launched, a graphic design business by accident kind of. It just, like, happened as a little thing during a hackathon. So now that’s its own, like, passive income stream which is great.

I gave up my apartment in London in April 2018. So I was basically just traveling the world as a nomad either freelancing or working remotely. Like, I got a remote job in August 2019. So basically, like, until covid changed everything I was just traveling full time as a nomad. Living out of my suitcase. Like, loving life.

During my travels, I also went to Amsterdam and I fell in love with the city. So I decided to move there, I decided to make that my home base. And so in August, I moved to Amsterdam theoretically, I mean, I just got there and now I have residency and I’m living there and see how I’d like it if I want to actually. Like, commit to making that a permanent home base. 

But yeah, I mean, I’m still traveling but definitely not as much. Obviously, covid has put a damper on things. I don’t want to be unsafe. Being a nomad and having this lifestyle, just opens your eyes to so many different opportunities, especially now with covid affecting things so much and other people, everyone’s working remotely from their house.

This lifestyle used to be so niche. Before when you would say to people that you work from home, they’ll just think like you’re spending all day not really doing anything but now I think people are really starting to understand, like, you’re still working. When you work online you still have a real job. 

And I think that covid has brought working from home and working remotely on this lifestyle to the mainstream much. I’m happy to see that this lifestyle is becoming much more popular.

Debbie:

Yeah. There’s so much there to unpack. I mean, just from the beginning of your story, Elina, like, you coming from Russia, coming here. I mean, you and I are similar, we’re both immigrants, right? 

And the first thing, the first experience, when you’re immigrating from a country when in terms of travel is not to like travel for leisure, it’s more for like a better life for yourself, for your family. So it’s so interesting when you finally find travel as something more, as something that you can actually enjoy and not something that scary or that’s going to take you from everything that you know.

And then after that, it actually allowed you to have more freedom with yourself. So it’s so interesting how travel can be so different for so many people or it can even be different in different parts of our life. So I love your whole journey, your story, and sharing that with us. Thank you for that.

And I’m really curious about you because when you went on that nomad cruise and you finally saw that it could be possible to do this and work from anywhere, what was it like for you to finally make that decision, right? And not to have that stable job that most people think about when they see  9-to-5? What was it like for you to transition to finally looking for something that would allow you more freedom and become a digital nomad?

Elina:

It’s an interesting question because when I went to that event when I went on that cruise, it was during the time when classes had already ended. So like I wasn’t working. It wasn’t like I was at this pivot where I kind of has to say, “Okay, I just had this experience, should I quit my job because I’m ready to live this life?” 

I didn’t really have to make any tough choices. I was like, “Okay, now I’m done with exams. Now I have to do my dissertation and then when I’m done with that, I can continue traveling, I can meet up with my new friends.” 

So I had time to let this absorb but I think it was when I graduated and then there’s this opportunity of a job in London that sounded great on paper and I’m sure it was actually a really cool opportunity but I remember feeling like I still wanted to travel for a few months and I was struggling with how to even tell the company. 

Like, “Look, I’m not ready to start right now. I want to travel for the next six months.” And then when I came back to London, I’m ready to start and I was like struggling and I was talking to a lot of people from the Nomad Cruise others and just being like, “What would you do? What should I do?”

I needed answers because I think at that point, I still wasn’t confident in myself to say like, “Okay, no matter what happens I’m going to be able to figure out any situation.” I have my work experience, I can make it no matter what. Like, whether it’s my work experience, my street-smarts, my knowledge. Like, what I want to create.

At that point, I was still too unsure of myself because, I think, in the US we’re taught like, “Okay, you have to follow this traditional path: you have to go to university and you have to get good grades. And then you have to get the job that sounds good on paper, and then you have to get promoted, and then you’ll have your pension.”

No one says, “Hey, listen, if you’re passionate about something, you should pursue it. Who cares if the money is not there? Eventually, it will work out.” Like, maybe some people get that kind of advice but definitely didn’t come from an immigrant family. 

So I think it was just like becoming an adult with a career behind me but completely trying to think in a new way and I think that that was a struggle for me. And I think once I made that decision, it still took me time to get comfortable with it. 

But I definitely had the fact that I didn’t have to worry about giving up an apartment, I didn’t have any fixed cost, I didn’t have to quit a job. It was more like I had to find my own comfort within this new space that I was in but I also was very unencumbered at that time. 

Debbie:

Yeah. And that’s the thing, when you’re at a time in your life where you don’t have a family to support, maybe you’re single or even have a partner, and you guys have more freedom, there’s no better time than now to be able to do this. 

Because, as you grow older, there are more responsibilities, there are other things that you have to do with your life. So I think that was just at the right point with you, Elina, that you were like, “I’m going to take a chance. I’m only living one life. I’m going to do this for myself and this is really what I want to do.” 

And now here you are even through the pandemic, living your life. You’re still able to travel, you’re enjoying that freedom that you created for yourself. 

So, looking back, when you finally got your first nomadic work, right? And you said it was in 2019, how did you find that job? How did you apply for it? Did you already have the skills? Or did you have a company that you were already working for and you had to negotiate through all of that to be able to work remotely with them? 

Elina:

So I basically created a career out of my hobby. Like, my first nomadic thing that actually was paying money. So basically, I was living in Colombia in this co-living, co-working house, and people were like, “Oh, I’m gonna launch a course. I’m going to launch a masterclass. I’m going to launch a program.” And I was like, “I don’t know what I’m doing.” 

And at that time, I think it was just like I was surrounded by a group of people who are very ambitious. And I think it, like, fueled this creativity spark in me. I remember some people giving me advice like, “You should just look for a remote accounting job.” And I’m like, “I’m not going to do that.” 

So I was like on Instagram looking at something and I remember seeing Instagram icons in someone’s profile and I’m like, “Oh, I’m not happy with how those look. I want to create a better set.” So then I went on Etsy and I don’t even know what made me think of doing that but I knew that they sell digital products.

And I went to see the digital products that were there and I was like, “Wait. they don’t even have anything that I’m trying to create.” So I basically spent the hackathon, like, creating this product in Adobe Illustrator, Adobe Photoshop. And I created my own Etsy store and I posted it there. 

And now that’s one of my passive income streams and I just think like that was just something I completely created out of nowhere, out of my hobby. And yeah, I didn’t have to negotiate. It’s just me.

And then I guess like something that’s not my own. One of my friends was telling me how he went to a conference and he met the CEO of a company that has, like, a travel hacking blog and he told me that they were looking for writers. 

And he’s like, “When he told me that they were looking for writers, I instantly thought of you,” because all my friends knew that this has been my hobby for like 10 years but I actually never did anything to monetize it. And he’s like, “Would you be interested in writing for them?” And I was like, “Yeah, sure. Why not? I have free time.” 

So then that’s kind of like how the whole thing began. So then I started writing for a blog as a freelancer and just writing about all my different travel hacking things. And then they asked me,. “Hey, can you write about XYZ?” So I would. Yeah, that’s kind of like how it all began. 

Debbie:

I love that, Elina. That is incredible. And it’s so interesting how life turns out that way, right? When you have a network of people who know your passion, who know what you love to do with your life, and then they spread the word about you, which is so incredible. 

And that’s the really powerful thing about network and having people around you who understand you. And you, putting it out there too. And this is the thing, no one will know what you are passionate about, what you love to do if you’re not putting it out and no one knows about it. So I really love what you did there, Elina. 

So when you finally start writing for this company, and we’re going to talk about it in more detail in your extended interview, one of the things that you write about often is miles and points, and traveling savvily. So, can you tell us more about that and how that became from just something that you did on your own to now being a part of the career that you have as a writer? 

Elina:

Yes. So, I think it’s just the way it all happened is just kind of interesting. Because I got into this so long ago. At that time,  I was working in finance and I remember I would look online and try to plan my vacation because I didn’t love my job and I was like, “Okay, I’m just gonna spend time planning my next trip.”

So then somehow I stumbled on this travel hacking information and I was like, “Wow there’s this really good credit card offer out there.” And then I saw, “Oh, you can get 75000 miles after applying for this credit card and you can apply for two of them.” And the minimum spent at the time wasn’t even that high. So then I said, “Okay, well let me see if I can get this credit card.” 

My mom and I have been talking about going on a trip to Europe and growing up with my mom, being a single mom, we didn’t really get to travel that much. I thought, “Okay. Well, wouldn’t it be great if we could use this to go on vacation together?” 

So I ended up applying for these two credit cards. I had my mom apply for them as well. There are American Airlines credit cards using the miles from flying to those credit cards. We flew to London and Amsterdam on British Airways in first-class. Like, round-trip. And we ended up staying in a hotel in both cities on points. 

Expensive hotels, again, we got it for free because of the points. And after this experience, I was completely hooked. First of all, it was incredible because I got to share this luxurious time with my mom and we had never been able to travel like that. But then also, I was like, “Wait a second, I could continue traveling like this. 

Like, I don’t have to go back to booking a $1,000 economy round trip ticket to Europe. Like, I could travel in style if I’m just savvy. So then I started just absorbing all this information, reading every single blog.

Remember, like this was 10 years ago. So this is before a lot of the mediums that we have now. I was reading a lot of old-school stuff and over all these years, this is how I started to travel. So by the time that I became a nomad fast forward, like, eight years of doing this hobby. All my friends knew about it because I would always talk about it.

When this website was like, “Okay, can you write an article about XYZ airline and this redemption?” Like, I already knew basically. I don’t want to say I know everything because of course, none of us do but I feel like I was already an expert in this space because it had been my hobby for so long that it was just like a very easy thing for me to do.

And also because I was freelancing for them and it was a little bit less formal. I was kind of just able to write the way I speak. So I  can talk in advanced terms, I can talk in simple terms and it was just a very easy transition. 

Now I have a full-time job. Basically, doing what I was doing before but now I work at a personal finance company and have a lot more responsibilities. But again, I completely focus on writing about this topic ’cause this is my role.

As a writer, now, I definitely write for a different audience because I have to think about, “Okay, if somebody’s not an expert, I need to make it easy for people to understand so they’re not overwhelmed or they don’t feel excluded.

But in general, like, by the time that I was already writing about this, I already knew so much because it had been my hobby for so long. 

Debbie:

That is incredible and what most of us want, right? Something that we love to do. And we can actually create income from that. 

So now that you are a professional writer and this is something, obviously, you didn’t seek out to do and in some way, it fell into your lap and it just became your main bread-and-butter, what are some of the tips that you can give us for someone who’s really interested in writing? They don’t know how to get started. 

How do you actually make this a sustainable lifestyle for yourself, Elina? Because you talked about freelance writing, it’s kind of like “feast and famine” for a lot of writers out there and a lot of creatives. How do you make it so it becomes more, for a lot of people, stable, right? That they always have stable writing jobs and they’re not constantly pitching every single time. 

Now, obviously, that’s understandable when you’re just starting out but in the long-term, how can this become more of the main thing that they can do? 

Elina:

It’s hard for me to answer that question because by trade I’m not a writer. I’m a CPA, I spent my entire career in banking where theoretically I was writing, like, investment pieces but it was very different, right? It was like very formulaic writing about a company’s financial health.

So I never sought out to be a writer. I’m just like a very techy, nerdy person that’s good at math. Writing just happened because of the hobby to educate the masses about this hobby, the main way to do that is through a written medium. 

So in a way, I’m writing in a very conversational style about a fun topic. So it’s not very difficult for me because, again, I’m writing about a topic that I already knew.

When I was freelancing, of course, I was making pennies compared to what I was making when I worked in banking in New York. But at the time, I wasn’t really thinking about it from a financial standpoint. I don’t know what writers make after graduating from school, the journalism degree. Like, that’s a completely different world to anything that I’ve ever known. 

And, again, because my writing job is about a very nerdy niche topic, I have no idea how that compares to other writing jobs at all. Yeah, that would be really difficult for me to answer just because I’m not a writer by trade.

Debbie:

But it allowed you to do it. And I think one of the things that you mentioned before is someone knows someone and it’s just part of your network. And I think it’s just putting yourself out there and allowing people to know what it is that you like to do, what your expertise is on. And you would be so surprised how many people actually watch you, listen to what you say. 

So that’s such an important thing to do but I love that you came through this type of industry in such an organic way and it really just fell into your hands at the right time, at the right moment. And you’ve already been writing for a little bit of time as well. So, I love that.

With you Elina, what has been for you since you’ve been doing this for a really long time? And looking into the future about maybe 30 to 40 years from now, what do you want your legacy to be and what do you want to be remembered for?

Elina:

Oh, that is a very good question.

What do I want my legacy to be? I guess I want to be remembered as somebody… So, I like to stick up for the underdog. I don’t like it when I see people unable to achieve success based on whatever telling them that they can’t. 

I don’t even know how to put this into words because I’ve never even thought about it, which is kind of crazy. But I think it’s coming from my experience of feeling like I didn’t have a choice in a way, even though, of course, I did. 

I grew up in New York, I had a four-year University education, I worked in finance, right? Like, I had opportunities, of course, I worked hard for all of them. But in a way, it’s almost like stupid, right? Because I worked for all these opportunities that I didn’t even want. I was like working for something I didn’t want. 

And I would say, like, if I was to give somebody advice about what to do it would be like, “Okay, just follow your heart and just do what you want to do as opposed to what society is telling you to do. Don’t do something just because it looks good on paper because life is not going to be satisfying.”

Like, even talking about networking, right? Like how you mentioned that I was networking with people. I didn’t even think of it as not working, I just thought of it as me being myself with my friends. I never sought out specific ways to market my skills. 

But then when I think about networking I think about like when I worked in finance and I would go to somebody’s hedge fund events and talk to people over drinks and have these conversations. I was like, “Why am I even here?” Because I just wasn’t interested.

And so, I guess, I would just always want people to say, ”She did things her way. She made her own path.” If that would make any sense.” 

Debbie:

Yeah, I love that. That’s one of the best things about having that type of life is knowing that the decisions you made in your life were your own decision and no one forced you to do it. It was something that you really love to do.

Oftentimes you want to please everyone, we want to please everyone else and we’re not doing that for ourselves, and that’s why we become so miserable even though we have all of the things that we think we should have in order to be happy. And then at the end of the day, it’s actually making us so miserable. 

So yeah, love that. 

Elina:

Thank you.

Debbie:

All right. So, I have some very rapid-fire questions for you, Elina, before we let you go. So you can only answer with one sentence or less. So are you ready? 

Elina:

Okay, I’m ready. 

Debbie:

First question, what has been the best money you have spent abroad and why? 

Elina:

Can I come back to that one? I don’t even know. 

Debbie:

Yes, absolutely. All right, next one, what superpower would you want to have and what would it be and why?

Elina:

To better know what people are feeling.

Debbie:

Oh, that’s a good one.

Elina:

So that I could be more situationally aware and more empathetic.

Debbie:

All right, next one. What is the best location you think someone can live in as a remote worker or a digital nomad?

Elina:

Playa del Carmen, Mexico. Great, weather, there’s a huge community, you have all the conveniences: a big supermarket, a gym, yoga classes. The beach is right there, restaurants that accept credit cards. There’s a Starbucks if you want. There’s a bunch of co-working spaces, hotels, hostels, and beautiful places to see all around that area. 

Just like one of the best locations for digital nomad. 

Debbie:

Loved it. Yes, Playa del Carmen is an amazing spot actually. So many things to do there and the food is so good. I love food. 

So when you travel, Elina, what are two things that really draw you to a place, and what keeps you going back?

Elina:

What draws me is just how I feel inside when I’m there. I can’t even put it into words, it’s just the specific feeling. And if I feel it when I’m there, I stay longer. I always book one-way tickets, I never book anything beyond that ’cause I don’t even know where I’m going to be.

Like, right now I’m in Puerto Vallarta but I’m going to Playa on Sunday because I want to be there. So I would say an intangible quality and what keeps me coming back is just wanting more.

Debbie:

Love that. And last question, what is the one thing you wished you knew before going into the journey that you have now?

Elina:

Trust myself more.

Debbie:

Love that. I think that’s what a lot of us wish for, especially when we’re young. Like, we are so unsure of ourselves. 

Elina:

Exactly. 

Debbie:

And we do a lot of things that you do out of fear or we don’t do things out of fear – it’s so crazy. 

Elina:

Yeah.

Debbie:

So we’ll go back to your first question, Elina. What has been one of the best things or the best thing that you have spent while abroad? Money-wise. Money spent abroad.

Elina:

Okay, I’m thinking I’m thinking. Oh my God, I don’t even know because I feel like I don’t buy stuff when I’m traveling because I travel with so many toiletries that my luggage is always so heavy that I’m like I can’t add one other thing. 

So if I buy something it’s like a teeny pair of earrings or like a little dress that can roll up really small. I never buy anything abroad. And I think also because New York is like the best sales and then I could stock all the promotions and get all the points from using credit cards. 

So I just like to try to save all my shopping for when I’m in New York. Yeah, that’s hard for me to answer. 

Debbie:

What about experiences? Have you spent any money on experiences? It doesn’t have to be items.

Elina:

I would say when I was in Brazil, in Jericoacoara. Jericoacoara is just like a tiny little hippie town, great for kitesurfing, on the northern coast of Brazil. 

And I remember one day, we went the dune buggy rides through the sand. So it’s like this little town is surrounded by a giant sand dune and you can rent like a little, I don’t know if they’re called ATVs, dune buggies, or whatever you call those cars, where you can put four people and there’s no windows or roof – you just stand.

We rented those and we drove all around. Like, going really fast and then we drove to the beach, and it was just incredible. Just one of the most beautiful views, completely surreal. Just being in Brazil on that water, I would love to go back to that town and do that again. 

Debbie:

Love that. Yes, that sounds like a really great experience to have and definitely feels like the best money spent ‘cause that’s something that you definitely can’t do anywhere else except for that area. So I love that. 

Thank you so much, Elina, for joining us today. We really appreciate you, if our listeners want to know more about you, where can they find you?

Elina:

They could find me on Instagram. My Instagram is @themissmiles. I’m also on Clubhouse under the same handle and then my website is the same: TheMissMiles.com. 

Debbie:

Perfect. Thank you so much, Elina. We really appreciate you. 

Elina:

Thank you.

Listen to Elina’s extended interview where she shares how to travel for free using miles and points.

What you’ll find:

In this episode, Elina shares how to hack your way to free travel by using miles and points.

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Show Credits:

Audio Engineer: Ben Smith