Working Remotely From All Over The World

Hello, welcome to Inside Scoop. I'm Paula Rizzo. I'm so happy to have you here today because we're talking about one of my favorite things, travel, but more specifically traveling to far-off lands for work. Okay, it's a little bit different than going for vacation, so I want to be able to really dig into how can you work remotely from anywhere in the world and be successful at it. My guest today is a friend of mine who I'm going to introduce to you in just a moment. Her name is Cassandra Santoro and she's a travel planner. She's in Sorrento, Italy right now where she spends half the year in Italy and half the year in the US. And, uh, you know, she has perfected working from anywhere in the world. So I wanted to talk to her and dive in a little bit on how you can do it most successfully because now, you know, working from home, working remotely isn't going anywhere. So we might as well take advantage of it, but do it in the best way possible. Because you don't want to always think that you're on vacation. That's not the most efficient way to go. And that's what I do a lot of the time. So I'm excited to hear from her, uh, you know, throughout the course of this, of this interview. And if you're interested in being more efficient and list-making, I have a freebie for you. If you go to paularizzo.com/list, I have my list-making starter kit. I'm a big fan of making packing lists and lists for, for work and things like that. So absolutely check that out. And I'm also a LinkedIn Learning instructor. And so I have a whole bunch of courses on LinkedIn Learning, including one about lists and the power of getting things done. So if you go to paularizzo.com/linkedin, you can check out all of my courses on LinkedIn Learning. And also, guess what? If you're traveling, those courses, one of them, this one in particular, is on Delta flights. I also heard it's on a JetBlue flight. So you might see me in the air, which would be kind of cool, kind of fun. And so absolutely make sure that you ask questions throughout this broadcast because we're going to be answering all of your questions about working remotely from all over the world. And I am thrilled to bring on the fabulous Cassandra Santoro. Thank you for being here, Cassandra.

Hello, ciao. Thank you for having me. Happy to be here.

Ciao. Yes, you're in Sorrento. So, uh, I'm, I'm excited to talk about all things travel with you also. Um, so you tell everyone where you are exactly, uh, in the world.

Sure, so I'm in southern Italy around the Amalfi Coast area, which I'm sure many of you know. I'm, I'm usually based in Campania, the region or the state here in Italy, which is Naples, Amalfi Coast. I'm based in Sorrento because it's great for getting around, it has a lot of means of transportation. And typically I'm here for the summer and then travel throughout all 20 regions of Italy for the remaining 6 months that I'm in the country. It's changed a little bit with the pandemic. Um, talk about remote work where now I'm, I'm here for a longer time. I'm in Sorrento now till October 1st. So not too bad though. Not complaining, but also—

No, it's pretty great. Yeah, exactly. Exactly. But you know, I really want to dive into, to being efficient and actually getting work done when you're traveling, because I find that to be the biggest distraction. Because when you're in a beautiful place, you want to enjoy it. You want to, you know, look at the sights and do different things. You don't necessarily want to be working, but there are some practical things that we should think of like Wi-Fi, like where are you, you know, where are you going to set up camp and all of that. What are some of those pieces, the practical piece, and then we'll talk about the mindset, but the practical piece of working remotely that you should really be thinking about?

Okay. So, um, the very obvious one, but I think is overlooked, is making sure there's Wi-Fi where you're going. Many say, but there's Wi-Fi everywhere. There's actually not. And I know it's very popular for people to go, and especially writers, um, and those who want to immerse in the culture, to go into these rural villages in Italy. But surprise, some of them don't have Wi-Fi still. So, um, there's a few ways to go through— to go about this. Um, I mean, there's several different, um, types of SIM cards or Wi-Fi devices, but I use Skyroam. So Skyroam, which is now called SIMO, S-I-M-O.

Okay.

And it's a device you buy for $150, but I've had it for 4 years, so I've made good use of it. And then you buy whatever plan you want. So they have just Europe plans, they have USA plans, they have global plans, and you could pick it for a day, You could do it for a week, you could do for 6 months. So I do the 6-month plan global, and then I— the normal price is $99 a month, but I get it for $49 a month because I take the 6-month package because I'm in Italy for 6 months. And I have to say, it's real. I mean, I've had it for 4 years. I can use it on the train, I can use it in the middle of the country. It's not 100% because nothing is with Wi-Fi, but I have to work like no matter where I am. Um, so yeah, I actually have it here.

Um, yeah, show us what it looks like. Yeah, and I, I think the website is literally skyroam.com, like that. Um, and can you show it to us one more time? It's just a little device that you take with you everywhere.

Sure. So I got the little— get the case because it will break. I have done that before. Um, but, uh, yeah, it's this device here, and you can just charge it on a typical USB cord. And, uh, and like I said, it's a little— okay, some people say it's a little heavy, or it could be— for me, I don't care how heavy it is.

If I can be on a beach and work, so, so that is a great tip to be able to really make sure that you can do what you need to do wherever you are. Um, what about some other practicalities as far as, you know, sometimes people will, will, you know, uh, rent a house or a room or something on Airbnb, and then it's not exactly what they thought. Or, you know, what should you be thinking of when you are looking to book a hotel or an Airbnb where you are going to be working for some of the time?

So something I've learned from New York and Italy, and this is going to be a surprise, but some people want to know if you'll be in the apartment all the time.

Interesting.

I know, it's a, it's a real— I've been living this lifestyle for 6 years and I've lived in different places, um, both in New York and Italy, and I've been asked this question probably one out of every 4 places that I've, um, that I've inquired at. So just keep that in mind. I would be honest because sometimes the landlord lives in the building, um, does it— sometimes they just want to know, and sometimes it will cost more. So, you know, I always say be very honest, tell them I'm remote worker. Now people are a little bit more understanding of remote work, which is one of the only things good that came out of the pandemic, right? These people understand you, you have to work, um, and that might be from your apartment. But, um, you know, and, and like I kind of mentioned it, really think about if you're going to be in this rural village, like I said earlier, but I keep repeating it because it is a dream and you can make that happen. But make sure to speak directly and say, you know, please be honest with me about the Wi-Fi. Should I bring my own Wi-Fi? Um, also, you know, and I'm sure you can relate to this, um, being in New York City, I'm— I need a little space And I need light, as you can see, I'm just blowing in. So make sure it's comfortable. I, you know, when I travel, the first thing I do is I go buy flowers, I get, or plants, fresh basil if I can't find flowers, 'cause this is Italy sometimes, and just make sure I have a lot of light and I set it up like an office. I don't set it up like a vacation home, you know?

That's very important. Like that's a big, you know, a big thing for mindset. And, you know, you just reminding me that one of the other courses that I have for LinkedIn is all about setting up your remote office. And so that is right here. It's called Organizing Your Remote Office for Maximum Productivity. And, you know, you can go to paularizzo.com/linkedin for that. And, you know, that— I created this course, you know, thinking people were gonna be working from home, right? But you're not necessarily at home now. We're talking about being somewhere else. But, you know, what Cassandra's saying, which is so important, is you have to treat it as sort of like a workspace too, right? So how are you going to set it up? Thinking about what do you need most to be able to work best. If you're doing video calls, make sure you have a nice setup in the background. Make sure that you, you know, have a place for your, you know, natural light and all of that kind of thing. Um, so it's just important to, to think about, to think about that, you know, as you're, as you're, as you're looking for your locations. Now, is there a, you know, as far as travel goes, is it better to stay in one place for working, uh, for a month, or do you think people should try and spread it out and say like, oh, stay a week here and a week there so you get to see more of the country? Or what do you think? What's the philosophy on that?

So this is a tough one. Um, actually my philosophy changed again after the pandemic, um, and I'll tell you why. Because I, you know, I was in a good flow. I was from 2017 to 2019 was my biggest travel where I really did all 20 regions. That was my time. So I was on a train every 3 days, and always worked. Yeah, every 3 days. So, and I— and you know, some of these places I stayed, but the one thing I did do is exactly what you're saying. When I arrived, because my mind was half in English, half in Italian, half on Eastern time, half on Central European time, I stayed a month, I stayed at least 2 months where I was. So, um, you know, sometimes 3, but I feel like I was still always traveling. But I, I do think you should start, if you're doing this for a year, for example, find a place that you, and then get adjusted first. And then once you get adjusted, then, you know, you make sure your Wi-Fi works, you know, your little portable Wi-Fi. I bring all my electronics from New York from B&H, everything, um, you know, to make sure. And I call them before to make sure, like, if I have a problem, I like having that customer assistance, you know, just making sure everything's set up. And, and then, and then you can move. Um, but, you know, do keep in mind you have to keep working, so make sure to take a train very early before American time wakes up, for example, if you're working with American clients. I always think about those things as well when I'm, when I'm actually doing the transport.

Yeah, yeah. It's just like those logistics, right? Like what time of day are you going to work? Are you working at the end of the day European time? Because that's, you know, in America it's, you know, their regular workday. So thinking that through, but also you're right. Like thinking through like even the adapters that you're bringing. Do you have a power cord that's going to work for European outlet? Like those are the things that you really need a checklist for to be able to make sure that you're bringing and you have all of the things that you need to really do your work. But also thinking about, you know, and we'll talk about how to make it fun as well. But, you know, the mindset switch, how have you been able to sort of, I mean, travel planning is your business. So it's like you're sort of working all the time in your business, on your business. You're also on vacation half the time. You know, it's like, it's a different kind of mindset, but how can we switch that off to be like, hey, I'm here to work and I'll get to the fun stuff after? How have you been able to do that?

Yeah. So it really is about balance. And this is weird because I'm in Italy where they say we don't live to work, you know? Yeah. But I had to, I had to come here with that mentality that work is my survival, you know? And even if I'm doing fine and not in a state of desperation, I always keep that mentality with me because I remember I can only live this lifestyle if I work hard. So You know, it's balanced, but also you don't want to overwork. So I, again, I, one thing I do, like, you know, that comes to mind is I have the Calendly, which works great if you have an online business or any kind. I mean, this is stuff everybody knows right now, but it's a good reminder. Instead of having a telephone number where people can call all the time, I make everything on my calendar. And I feel that International travelers that work with me are really appreciative of that. So they don't have to figure out the time zone. And with that being said, I do on that calendar, I now take off 2 days a week and make sure that's me time.

Oh, see, I love that. Okay. So let's talk about that. Let's talk about the scheduling, like the actual, like, let's get down to business on how you set up your schedule. Because, you know, a lot of times people will think, oh, I'll wait till the weekend. To do the fun stuff. Um, but the weekends, maybe not right this second because we're just coming out of the pandemic, are typically the more, you know, people around. You don't get to see the sights as well as you could have and all of that. You know, you might want to take advantage of some of the daytime, weekday stuff. So how are you setting up your, your schedule day to day, week to week, uh, you know, while you're working and also seeing beautiful places?

Yeah, I mean, that's an excellent point. Uh, you— we think alike. I, um, especially here on the Amalfi Coast, as locals, um, we're not— I mean, I'm not saying that locals don't go to the beach on Sunday because people do work a normal work week, but nomadic quote-unquote workers, we do try to avoid the beaches on the weekend and the sites because of that reason, because we have it 5 days a week, as you said. So, um, yeah, I do, I do try to give my days off the week, um, like Tuesday, Thursdays. Or based on museum days. But I also, you know, I also do keep it open. So if I have a client that has an emergency call, I do try to keep that in mind, even if it's my day off. But yeah, I like to, I like to, not even just for me time, like you said, to explore, because a lot of my job, as you mentioned, is to kind of check out the area. And I'm sure everybody that's working uh, remotely feels the same. They want to explore the area. So on the days of the week, you have more time to speak with locals.

And yeah, that I love. I love that. I, um, so if you're watching live or watching the replay, give us some, some questions in the comments below. We'll be sure to get to those, uh, to, to answer your questions about working remotely from anywhere in the world. Um, I want to shift a little bit to, to the actual traveling because you did just travel from the United States, from New York to Italy. And that was, you know, it's a unique, unique time right now. You know, we're in June of 2021 as of this recording. So things will probably change in a week or two weeks. But what was your experience like? Because you took one of the, you know, first flights in the pandemic. So you saw, you know, during the pandemic, but now just a week ago you were on a flight where you, it was a COVID-free flight. So tell us about that.

Yeah, so, um, for Americans to enter Italy without quarantine, you have to take, um, Delta, American, or United COVID-tested, uh, flights. Uh, United is not running yet, that run starts in July, but American and Delta are running. Uh, just a side note that you can take other flights, you might just have to quarantine if they stop you. So just a note because that's confusing people a lot, but I do mention that in my blog. But basically Um, you know, it, it was pretty efficient. Uh, first you have to take a PCR test 72 hours before the flight. Some, for American, it's 48 hours, and Alitalia. So again, between 72 and 48 depending on your airline, right? And, um, you have to show that when you arrive. Um, you can't do anything without showing that test. They don't even let you take the COVID test at the airport without showing that.

So, wow, okay.

You know, make sure you had it. Um, and then you take a COVID rapid test, uh, at the, at the airport in USA, and then you get on your flight. And then when you— I'm sorry, they do make you fill out some forms while you're waiting for your test that registers you to take a test once you're in Italy. So you get everything set up. Yes, it's like 4 steps. Yeah, but it's organized considering you know, it's, it's several steps. Some of it's in Italian and they try to translate it, but it actually is—

you—

it's about 2 hours of inconvenience.

Yeah.

Um, and then once you're on the flight, it feels pretty normal. Uh, you know, we didn't have that many people on the flight, so it was really comfortable. Everybody had their own row. Um, and, uh, they're serving meals again. I, like, last year when I went, it was very— and I had flown business on the way home, and it like one meal. Yeah, um, small. So now they're kind of going back to normal because everybody's tested, right? So, um, but you do have to wear your mask.

Sure, of course. But it, you know, it is nice to know, you know, for people who have not traveled during the pandemic— I did travel a bit, you know, uh, domestically throughout the pandemic, um, but for those people who have not traveled, uh, internationally, like I haven't traveled internationally yet, um, it's nice to see that, you know, there are airlines that are doing this, there's countries that are, you know, uh, really putting out their best effort to make sure people feel really comfortable and all of that. Any other travel tips for people who are thinking about international travel specifically? Maybe not even for working, right, but just for vacation, let's say, uh, you know, just what you're seeing in Italy specifically and anything, anything there.

Yeah, I, I think you just have to be flexible. Um, not everything's open here yet. Uh, you know, they're starting slowly. Uh, June 1st in Italy, you were just able to eat in indoor restaurants. So give people some time because many of the businesses in Europe have been closed for 9, 10 months. So please just keep that in mind when you're traveling. Maybe, um, you know, don't be so set on anything. You know, I just say if you're used to traveling and you're just going for the experience to be here, just enjoy it. Um, I, I would, and not because I'm a travel planner, but I would say if you're not very, very comfortable traveling, to hire an expert in the place that you're going, or at least have somebody on call because things are changing, in case you need some assistance, somebody that speaks the language, um, or making sure you're staying at a hotel versus an Airbnb, for example, again, if you're not comfortable traveling, um, so you have a concierge that can assist.

Yeah, I think that is very important. You know, my husband and I went to Greece uh, now 2 years ago. And I'd never been to Greece. I was very intimidated by everything. So I did hire a travel planner to help us because I felt like I need, I need somebody who knows, who knows it, who speaks the language, everything. And it was really wonderful because we did have some issues with one of the ferries that we were taking. You know, it's kind of like Italy where like things get canceled and no one tells you, and it's like, okay, I guess You know, uh, but I was able to contact him in the US and like he got right on it and he did it. So I never had had a problem. So it is nice to be able to have that, you know, person to, to help you. And I want to point people towards your Instagram account, which is actually how we met, because I found you on Instagram as someone who loves Italy. Uh, so if you go to instagram.com/travelitalianstyle, that is Cassandra's, um, fabulous Instagram account where she shows you basically all behind the scenes on what's going on on Italy. So if you're not there, you'll feel like you're there, which is what I do. I live vicariously through you all the time, so it's very, very, very nice. Um, and you're also a podcaster. You have a podcast that's, uh, you know, a little bit new, but if you go to rediscoveritalypodcast.com, you can check out some of those episodes, which is, which is super fun. And I want to get to some of the questions that have come in, uh, as we've been chit-chatting. And if anyone has any other questions, feel free to put those in the chat boxes below and we'll get to you. Tatiana is happy about checklists. That I love seeing. Yes, it's true. Create that checklist so that you could just use it again and again when you're traveling. Sam has a question about working in different time zones. Do you work early and late with a break in the middle, and how do you deal with sleep and rest?

That's a great question. So for us, we work It's a little strange for me because I have to work a little bit longer because my office, you know, my partner office is on Italian time. So I wake up and I have to work and then Americans wake up at like 1:00 PM. So I have to keep working. But typically if I'm just working with American clients, I do set my calendar to Central European Time. And I don't, every day I don't have it 9 to 8 o'clock at night. I do say, listen, My schedule is 9 to 4 or 9 to 5 Central European Time. It could be a little early for you, but that's the best way to get in contact with us. If you really can't make that time, please request a different time that we could speak. And then, you know, but a couple of days or maybe one day a week I'll have till 8 PM. But I do find that when you're very open with people, like I work on Central European Time, they're very excited to talk to you in another country and to talk about that. So I haven't had any issues, but as far as balancing my work, I do try to go like, especially here to the beach in the morning. It's better for crowds anyway, but you know, and like do my food shopping or everything from like 9 to 11 or 8:00 AM to 11 is like my time. And then I, you know, and you're working.

Yeah.

Except for aperitivo, you know? Yeah.

Well, so fabulous. You need an Aperol Spritz. Like, you know, you just have to do what you have to do. It's very true. It's part of the culture, but that's it. I mean, that's the whole point. You want to make sure that you are doing what the locals do while you're working. So to be able to kind of work that into your, to your life. Um, I have a question about, um, visas. So the question is, as an American citizen, are there any visa requirements to work remotely? Like if I was planning on being there for less than 90 days in August, do I need to get a work permit? Now you're not an expert in all of this, but what, what do you know about this so far?

Sure. So, um, yes, the 90 days is the limit. I always tell people as a travel planner, 84 days you should depart home, especially if you have connecting flights out of Germany or France. I would not stick it to exactly 90 days, just a little tip. Um, but also there are places such as Florence, remote villages in Lazio, the region of Rome, and a few select areas throughout Italy that are considering it's in the works, uh, to offer visas for those who want to work remotely and who will pay a little bit of tax to the Italian government, and then they'll give you a visa to stay. Um, I think that would be the best way if— or just do the 100, you know, or 90 days or, um, or 84 days and then come back in a few months. But, um, you know, I always say, and it's kind of like an obvious thing, but I always say the best thing to do is hire an immigration lawyer or someone that is familiar with this. And I've had a lot of friends that have been successful in this route if they really wanted to stay in Italy for a year or a couple years, actually, um, finding— I don't want to say the loopholes, but the correct way to do it. Um, and they can find all these updated, you know, possibilities as well.

Sure, right, right. You want to be smart about it, you want to do it the right way, all of that, you know, for sure. But there are definitely ways, and you know, there's a I suspect this is going to be popping up more and more. Like when we used to see, remember the €1 houses, how that was like a big thing. Now I think this is going to be the next big thing that, you know, all of these small towns are going to try to get people to work remotely from there. You know, that'll be the, the next big thing. Um, I also put in the chat, uh, the experience that you had, your blog post about, um, traveling to Italy and how that, how that was. So that's all in the chat. Um, there's a blog post there for those of you who are who are keeping track and want a little bit of homework. There you go. Uh, there's a question.

One thing, not to interrupt, but could I just say, um, for those who are interested in these visas, I had a thought. A really great, um, account to follow— I think you have to pay a little bit now, but you can follow them on Instagram— is Italy Magazine. That's where I see— or the Florentine newspaper in Florence. So their English newspaper, or English— Italy Magazine does like announce some of these visas. Sorry to interrupt. I said, oh my gosh, that's the Hey, it's a good fact.

I'm going to put it up there. Italy Magazine, check it out on Instagram or Florence. What was the other one, Florence?

The Florentine.

The Florentine. There you go. That's great. That's a good, that's a good resource. Someone is asking about the calendar that you use, which is Calendly. So I'm going to just stick that up there so that people can see, which is a very, it's a great productivity tool. I have to say, you know, to be able to show people here is my calendar and you can block off different times. And then they can choose which times you're available that then you can have your call. There's another one called ScheduleOnce. That's the one that I use. It's just a nice way to kind of for yourself too, to block off your time.

And it's nice because when they see the calendar, it's on their time zone. So then they don't have to get confused. So, you know, they usually, I mean, with some people they say they have to click it, but typically when they open the calendar, it shows up on whatever time zone they are in. So you don't even have to worry where you are.

Yeah, I love that. That's so good. That's perfect. Yeah, because you just want to make it easy because it is confusing. I mean, it's confusing when somebody's on the West Coast and you're on the East Coast, you know, like that. So you can only imagine 6, 7 hours, 8 hours, 10 hours, depending on where you are. Uh, you know, it's a, it's a big, it's a big thing. Uh, well, Cassandra, this has been fabulous. Thank you so much for, for being here and giving us all of these wonderful tips and tricks and ways to live remotely and be out there and also get some fun into your life. Uh, I appreciate it so much. And if, you know, anyone has questions after the broadcast, if you're watching the replay, leave them below. We'll absolutely get back to those. Um, and, uh, that's, that's the story. So, uh, absolutely make sure that you are following Cassandra's Instagram because I'm obsessed with it. So instagram.com/travelitalianstyle. And also please check out her podcast at rediscoveritalypodcast.com. Any last words of wisdom for our, for our, you know, remote workers?

Oh gosh, I say just do it. Don't overthink it, but prepare. Make your list. I think Paula would be very proud. Make your list, do it efficiently, and plan for it. It's great to be spontaneous, but if you give yourself a little bit time to create a schedule, plan out your, you know, your travels. It'll be the best experience and you won't regret it. So I obviously highly recommend it.

Yes, fantastic. Well, thank you. Thank you again for being here, and thank you to all of you who have stuck with us. Uh, looking forward to seeing you the next time, and if you have questions, let us know. Otherwise, we'll see you later.