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122: How this personal travel planner turned tragedy into triumph with Cassandra Santoro

On this week’s episode, I speak with Cassandra Santoro who is a personal travel consultant and founder of Travel Italian Style.

Cassandra’s life was turned upside down when she lost her father to cancer and she began to question her life choices.

This tragedy led Cassandra to leave everything behind to find her Italian heritage and create a business in Italy as a travel consultant.

Listen on to find out how Cassandra is able to run a successful travel consulting company.

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Show Notes:

Debbie: 

Hey everyone! Thank you so much for joining us. I’m so excited to be here with Cassandra who is a personal travel planner. Hey, Cassandra, how are you?

Cassandra: 

Hey Debbie, I’m great. Thanks so much for having me.

Debbie: 

Can you fill in the gaps of your story and why you live an offbeat life?

Cassandra: 

Yeah, sure. In 2002, I lost my father to cancer. He was very young and it kind of just set something off that I want to explore my heritage. So, I had gone back and I lived in Italy for a little bit and I got my dual citizenship which was in dedication to my father, my grandfather and my grandmother. Something wasn’t fitting so, I came back to New York and I said, “You know what, my dream, really, is to live six months in New York and six months in Italy. How do I do that?” So, I worked, worked, worked.

I worked in the wine industry, I worked in the event industry, always going back to Italy and doing things on the side, like helping people that would come to the winery and say, “Hey, how do I do a wine tour in Italy?” or “How do I do this in Italy? Can you help me? I know you how much you love it.” I was a tour guide in between there – I did so much. And then, finally about four years ago, I was able to pack up my stuff, like a lot of people on your show, sell or give away all my belongings and I decided to not have a permanent residence and spend six months in New York and the other six months in Italy running a travel business called Travel Italian Style. So, that’s how it all started and that’s where I am now. Four years… I can’t believe how quickly time passes.

Debbie: 

When you lost your dad, obviously that was such a traumatizing experience for you. I mean, for anyone who loses someone really special. What really pushed you to follow your path, aside from that loss to finally do what it is that you really love to do?

Cassandra: 

I think it was that he didn’t have a chance to do everything. I don’t think he had a lot of time or I don’t think he thought he had limited time, I should say. So, something just came to me after doing a little bit more talking with my grandma and my mom about my dad’s past as well and conversations we had. So , that’s what inspired me to do whatever I want because we’re not guaranteed. As cliché as it is, we have no guarantee.

So, sometimes we let finances stop us, sometimes we let fear stop us but I think what’s important is that we just believe. Again, cliché, but I am a big fan of just having faith and working really hard. I knew there was a way to do it. In the beginning, when I first started, it wasn’t exactly what I wanted. I just worked towards having this exact lifestyle. I had to start out a few months in Italy and a few months here. I kept working my way up and I didn’t lose faith. Thanks to the lessons I learned from my father on that.

Debbie: 

And did you have any process in order to prepare for this new journey that you wanted to do to live in New York – half of the year and then another half of the year in Italy in order to make that big change and become a personal travel planner?

Cassandra: 

Yeah. It’s funny that a lot of people ask me, it kind of looks like I just hopped over to Italy and I said, “No, I was preparing…” It would always look like that. I tried to be honest on Instagram but at the end, it’s like you have to tell them how it is because you know that other people are watching and trying to figure out how to do something similar. Not everybody, but a lot of people reach out and what I usually tell them is, “Listen, my journey started 13 years ago. As soon as I came back from Italy for the first time in 2006. So, I lived there for three months in 2006 and then lived there for three years, from 2008 to like 2011 or so.”

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Even in between those journeys and from there I was preparing, how was I preparing? Basically, first I was learning everything that I wanted to learn about Italy, whether that was books, being a tour guide or a tour leader here. They’re very specific about tour guide versus tour leader – you have to have a special license. So, I was a tour leader and I was speaking to Italians. I was always networking, whether it be travel events, Italian-American events, business events – I was always doing that. For the whole period that this vision came in over a decade ago. But most importantly I was also taking business courses. I think a lot of people… Some of them were okay and some of them were helpful, but I learned at least one thing from every single thing.

I studied and I felt in order to learn to do this the proper way you have to invest, that’s like the advice I give everybody. So, I do not regret one dime I spent but I definitely put a lot of time learning how to run an online business, learning how to be location independent and all the fun stuff about Italy. I worked in the wine industry, I worked in the event industry to really understand logistics. I even did weddings, which doesn’t seem like it would help to live abroad in Italy – the offbeat life. But it did! It helped because I’m able to use some of that even here. Now, I do destination weddings every once in a while. So, that’s kind of a quick summary of how long I’ve been on the journey.

Debbie:  

It really looks that way for most of people’s journeys. When you see them on social media or when you hear their story on podcasts or on blogs because you just see the end or the middle of it. And it’s so easy to forget that there were so many things that you had to do to get to this point where you are now. And I think we often forget that and it’s pretty crazy.

Cassandra:    

Yeah. Because we all have the same idea, right? Like we all want things and we want it now. As I said, it’s just excitement, right? So we all think it could just happen tomorrow but as you know too, on your own journey, we have to try out different things and try different courses and different experiences in different jobs before we can really figure out if this is the right thing for us.

Debbie:   

Now, Cassandra, when you left New York City… I know for myself when I finally left my job, my steady job, I had the “what now?” moment? You start to panic even though you’re finally going after what you want, you still have those moments. What was it like for you? What was your “what now” moment?

Cassandra:  

I feel like sometimes I still have those. I think in the beginning, I was like, “Yes, this is awesome! I did it and now I’m here and I have this job and I’m making money.” But things happen. Maybe certain vendors, because my job is a personal travel planner, I’m working a lot of times as the middle man and sometimes the people on the other end didn’t come through and it really wasn’t easy in the beginning. I kind of had like this “what now?” moment – not in an expected way. I had everything I wanted, but I was like, “This is so hard.” And it doesn’t look like a hard job, we can talk about this more later but basically, I decided to do everything “me” as me is the main contact. I’m dealing with the Italians, I’m making the payments, I’m doing everything. There’s no American company in the middle helping me. So, I came here and then I thought it was like the coolest thing ever that I was like, “Yes, I’m going to be the person who does every single thing with my business.” And then, I just had a breakdown and I’m like, “Oh yeah, this is not easy. What now? What do I do now to handle this all?

Debbie:   

That is a really good lesson to learn, especially in the beginning and you feel like, “I’m going to take over the world” and then all of a sudden you get a reality check for something. Sometimes even the littlest things you start to break down.

Cassandra: 

100%. I mean it’s just reality, right?

Debbie: 

Now, you’re talking about setbacks. What has been the biggest one that you’ve encountered so far in your journey into this entrepreneurial lifestyle that you have?

Cassandra: 

Okay, so this is something that I’m really trying to still learn how to cope with. I’ve done a lot of spiritual and self-work on this. The biggest setback, besides having to deal with the Italian vendors, God, I love them, I’m one of them, I have an Italian passport. Besides getting over the cultural thing… I speak a lot about this a lot on Instagram so, if any of my followers are listening, they probably have heard this before so, I’m sorry, but people are not being so honest. Like when things have been taken from me or my business has been replicated, I had to get a lawyer and do all that stuff.

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It was a few friends several times; one was a mentor, one was an intern. That was a huge step back for me ’cause I have to step into that reality where like, “Oh, there’s gonna be a lot of tough stuff.” I don’t know if it was a situation that set me back but I think it was the point that like, “Oh yeah, you have to be a lawyer too. You have to get lawyers, you have to do legal stuff. People aren’t going to be honest. This is not going to be all butterflies and rainbows. Even if you trust people, you’re going to have to really make sure things are legally binding because a lot of people have other ways of working.” I think that’s what it was like I realized that not everybody works like me – I wouldn’t even have to sign a contract. I would be like, “Hey, I would never steal from you or lie to you.” But, unfortunately, I’m not saying that these people are bad it just means that they had other things on their agenda. And maybe didn’t have the same means I had to learn how to start a business. So, that has been really tough, I mean, I’m actually getting better at taking care of these situations and they don’t happen as frequently ’cause I don’t focus on them. But in the beginning, man, that was tough, that was a really big setback.

Debbie:  

Now, for somebody who’s listening to this and their either in that same point as you or they’re not there yet, but they may encounter it. How do you deal with that kind of situation?

Cassandra: 

The first thing I can tell you internally and, actually, physically for the job aspect of it; don’t run and waste your money on a lawyer necessarily, send the necessary letters out. But don’t make it your whole focus and that’s why I think it’s more important on this entrepreneur journey or nomadic life journey is to really be true to yourself and focus on what you have to do. These people are going to come and go. They’re going to try things. Eric Thomas, I love him, he’s like old school motivational speaker but he’s still one of my favorite. He always says, “These people can be everything they try but they’ll never be their best selves because they’re trying to be somebody else.”

So, if you’re in a situation, you’re dealing with this type of circumstance or just something holding you back, just remember to be true to yourself. Keep staying original, keep growing, keep changing up your business. Don’t keep it stagnant. And then, you’ll always stand out for doing something unique. It’s not being better than these other people in any sort of business. It’s not about competition it’s just… have competition with yourself! It keeps it fun for you, it keeps you looking original, it keeps your audience and your clients excited to see what’s next.

Debbie:  

Yeah. That’s a really tough thing to go through because you already have so many different things pulling you in different directions and then you have to deal with this too. That’s a lot to deal with as an entrepreneur, especially if you’re just starting out. So, not letting that get too much into your head is such good advice. Otherwise, you’re just going to go crazy and you’re going to give up.

Cassandra:  

Yeah, exactly. That’s exactly it. Like this stuff really can push you. I mean, I’ve been severely depressed. I was listening to your last episode about anxiety because it’s true. I’ve gone through the same thing. But just consider it as normal. Like you’re saying, it’s gonna be normal, it’s gonna pass. Just keep focusing on the things you love.

Debbie:

Cassandra, when somebody is trying to find a business route in a different country like you did, what is it like starting in a country like Italy or somewhere in Europe or even anywhere else? I mean, I’m sure it’s a lot different than the United States; there’s different tax laws and all of that stuff. How did you figure all of this stuff out? Because it’s already hard enough in your own country, let alone go to a different one and start that there.

Cassandra:   

Oh my gosh. I know sometimes I asked myself that like, “How did you figure this out?” Instead of the “what now?” it’s like, “how did you do this?” moment. It’s like that’s when you’re feeling motivated. I just, again, got the proper guidance from the proper legal people. I would never recommend someone just start out being like, “Oh, let’s just see what happens.” I went to lawyers here and there, I went to accountants, I asked my accountant to speak with people. When I have questions, I ask the accountants here, I don’t ever risk it, I don’t Google.

This is stuff that I say like, “Don’t Google this stuff. Okay?” Because, not to be offensive, but sometimes people on there aren’t really sure or maybe something worked for them and it’s not really the law. The funny thing about Italy is that it’s constantly changing. And then, sometimes they may just say, “Well, we decided we don’t want to follow that law so we’re gonna make it this way.” So, I think just keeping up to date and make sure you have a strong team behind you that can help you in the best way possible with all this information. Which is kind of a broad answer, but it’s really what I did.

Debbie:   

Yes, talking to the right people is the key to that. And like you said, networking and getting to know as many people as you can because it’ll lead you to the right sources, especially when it’s a country and a place that you are very unfamiliar with.

Cassandra:   

Yeah, definitely. And even if you speak the language, I don’t even think you have to be fluent in Italian. I mean, I can speak Italian. But just make sure you have somebody that can read Italian or understand Italian on your team helping you and then things should be pretty smooth.

Debbie:  

Yeah. Now, going back to when you were starting out and you were just planning this, how much money did you actually save before setting off and becoming a personal travel planner full-time?

Cassandra:  

Yeah. That was a big mistake. I didn’t save that much money that’s why I tell everybody to do it. But I made up for it very quick because I got part-time jobs and things like that. I actually got fired from my last job, I’m not embarrassed to say a bit or a little of those, but I say that because it obviously happened as an omen. They knew I wanted to take this venture. I was working more on this at home and it obviously was showing in my job. And they were going a different direction so I didn’t necessarily have the time. But what I wish I would’ve done is at the same time, because I was already taking courses on things how to run a business while I was working full-time, would have saved at least a year worth of business paychecks before doing this.

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And again, that’s just my personal opinion but I think that would be smart to really start working on this while you’re working full- time. You’re gonna be tired like what Gary V. and all these people say but it’s really your side hustle. I really believe that. I think that you’ll be happier and things will be easier. I have a friend that started a business and then she really decided she didn’t want to do it. So she was able to take three months and sort of just travel and think about what her next business venture she’ll be doing ’cause she saved in advance. Just think of it that way like you want to be ready for not just the unexpected with your business but ready for it. And you don’t want to feel pressured to do something you don’t want to do just because you spent the money to start it off. Put savings aside to have multiple ideas.

Debbie:  

I completely agree with you on that one, Cassandra. I think I’ve seen too many people who just leave their job because they hate it. I mean, honestly guys, come on, we all hate our day jobs. Unless you’re getting verbally and physically abused every day just stick to it and save as much as you can. And another thing that I always tell people too is to pay off as much debt as they can before they leave because that’s another thing. Even if you have money saved but you have a ton of that, all of that money is going to go into your debt instead of your new lifestyle. I think I’ve seen a lot of people having to go back to a nine to five doing too many jobs that they hate. And again, what’s the point of leaving your job if you’re gonna do something that you hate – it’s the same thing.

Cassandra: 

Yeah, it’s true. And it’s such a great point.

Debbie:   

It’s really easy to kind of just say, “Oh, screw this! I’m just gonna leave” but it’s a different ballgame once you actually get in there and realize how hard it really is. So, you have to prepare yourself, there are certain people that have no choice or if you get fired then you really are pushed into it and I think you become more of a hustler that way. But if you have a choice, just stick to it. I know it’s really hard, everyone. I know, I’ve been there, I know Cassandra, you’ve been there too. We’ve all been there, but do what you have to do because you’re going to do a lot of things you don’t like even in your business that you start.

Cassandra:   

Yes. That’s an excellent point and a great, great reminder definitely.

Debbie: 

Cassandra, how are you able to make sure that you were financially stable once you were up and running with your business?

Cassandra:

So, I start to charge people a little bit when I was still working. Not a lot, but I started introductory rates and I was able to, at least, I knew I consistently had a couple clients a month. When I first got fired, I actually went to anthropology on fifth avenue. I strategically worked part-time jobs at companies that I knew. I supported entrepreneurs, they’re really great with women entrepreneurs. That would be some aura where I can learn something. So, I had the backup but my actual business, when I finally let that go, I made a point to myself to say, “If I had this many clients a month, this is how I made business.” Because as a personal travel planner, I charge consulting fees in advance and that’s how I make my money.

I don’t have to rely on commission per say. Like a lot of other travel agents, I didn’t want to take that risk, especially with Italy because, I love this country again, but they’re not known to be so buttoned up about paying you. In general, they’re just have a very relaxed atmosphere when it comes to money. So, I think it was just strategically knowing how many clients I had a month and if I didn’t think I was gonna have that many clients ’cause it was a slower season, I had to pick up a part-time job. Before I set off on my official Italy adventure, I was doing that in New York.

Debbie: 

That’s such a good way to do it because at least you still have money coming in especially since you were laid off from your job and you had no choice – that’s a really hard thing to do. But you’re such a hustler that’s why you are where you are right now – because you do what you need to do.

Cassandra:

Thank you. I love hearing that. It’s really good reminder.

Debbie:  

So, let’s fast forward to 50 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?

Cassandra:

I would love people to say, “Wow! What a real person, what a person who just loved what she did and was good at it. Helped so many people and that they learn something from it.” Whether it was one of the talks I was doing or maybe one of the trips they went on that they learned something about the Italian culture and it changed your life. It’s always been my passion for Italy because the first time I stepped on the Italian soil after my father passed away, it was like, “Wow!” It was like that “aha!” moment for real. I’ve really felt at home, I felt at peace and I would love as many people as possible to feel that same peace and connection to Italy or the stories of Italy if they can’t physically get there. And I really hope that people remember me for bringing that to them.

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Debbie: 

That is such a great point too; feeling at home somewhere. That’s a thing that a lot of us would like to feel, right? Especially, you’re the type of person that’s always on the road and I think a lot of us are finding that and would be great for everyone to have.

Cassandra:

Yeah, it definitely would. And we can all find it eventually. Right?

Debbie: 

Yeah, absolutely. I think if you look hard enough, that’s why you love traveling.

Cassandra:

100% travel for life for sure.

Debbie:

Is there any question that you wished people asked you more of?

Cassandra:

Well, besides like how I stay thin while eating so much Italian food then, I usually tell people like right now ,I live on the Amalfi coast so, I have 60 steps just to leave my house and come back. So, if anybody’s wondering about that. But I think they ask me, how do I physically live like this as far as like luggage and things. I’m sure many of your guests have said the same thing; I don’t feel a need for things anymore. I’m sure you can relate to this too. I mean, of course, I have like emotional attachments. It’s hard because of what they’re saying. It’s so silly, but I don’t even drink soda but my friends here, “She’s getting these soda bottles with Napoli Pizza – women with like pizza hats on them and stuff.”

It’s like an Italian artist and I was like, “I so want to buy all of them and keep them.” But you start to not get attached to things. So, I only have what means the most to me and what’s necessity when I travel. So, I traveled for six months with a suitcase and a  carry on, a big suitcase, and a backpack for my laptop. And then, when I’m in New York, I may have another suitcase for the shoes. But I only have three bags, probably, to my name. And a bag of baking stuff at home that I’ll probably never use again but I asked my mom to store that for me. I think people ask like, “How do you do it with no stuff?” And the answer is like, “If you are preparing for this lifestyle, really sit down and go through your things. How much of it do you need?”

I don’t want to be hurtful and let go of your memories but is there a way to upload your photos? Is there a way you can give something away? Sometimes I’ll give something to a cousin or my nephews, like a special doll or something that I had as a kid so, it’s still in the family but I don’t feel the need to hold onto it when I travel. I don’t know if you can relate to that at all, about all the stuff having so much stuff.

Debbie:

Oh yeah, absolutely. And honestly, I don’t really spend any money on things anymore. Also, when you travel or if you live somewhere else you’re always gonna find those things in a different place. It’s not like you’re going to Mars when there’s nothing there.

Cassandra:  

Yes.

Debbie:

You don’t need to lug all of that around.

Cassandra:

Yeah. And you know, it’s funny, you made a good point. Sorry, I’m just gonna say, you might adjust to other things when you travel. On top of your regular things being here, sometimes you could find better things. So, that’s what I feel about my face wash. Love my Italian face wash.

Debbie: 

So true. Right. They’re probably more organic and smell better ’cause Italian people know how to do it well.

Cassandra:

100% lemons. Everything’s a lemon here.

Debbie:

Yeah. Are you working on anything currently that is really exciting to you?

Cassandra:        Last year I finished going to all 20 regions of Italy, so that was cool. Now I’m working on actually putting those experiences into play. It was a personal goal to really go and make connections everywhere and to see what I can put together that isn’t something necessarily on Google. So that was cool. And a few like writing and speaking things, but still in the very, very beginning stages. I think the most exciting right now are these travel experiences and putting them together for guests. I’m really excited.

Debbie:   

Yeah. And make sure that you all listen to the extended interview with Cassandra because she’s going to let us know more information on how you can also become a personal travel planner. So, I’m really excited to talk to you about that too, Casandra. Now, our listeners want to know more about you. Where can they find you?

personal travel planner

Cassandra: 

Sure. So, my website under my “About Me” or “Meet Cassandra” page; TravelItalianStyle.com. And I’m most active on Facebook and Instagram. In Instagram, I’m always telling stories about true life, living in Italy, true life as a personal travel planner. I’m really honest. I don’t necessarily always share tips for traveling but I do share more tips for real life. Of course, it’s a lots of tips because I’m like, whatever I’m doing, I’m telling you what I’m doing. So, I guess that is a way of sharing tips but it’s more into the life of this type of lifestyle and what it’s like living in different places of Italy. So, I would recommend there. And if you go to my website, there are some links to a Tedx talk. I share a bunch there and some other interviews and things on my website.

Debbie: 

Perfect. Thank you so much, Cassandra, for being here today and for telling us all of your amazing tips and tricks on how to do this lifestyle. We really appreciate it.

Cassandra: 

Yeah. Thank you so much for having me.

GET THE EXTENDED INTERVIEW WHERE CASSANDRA SHARES HOW TO BECOME A REMOTE TRAVEL CONSULTANT. 



 

Show Credits

Audio Engineer: Ben Smith


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