Ep. 297: How This Content Creator Has Been Able To Do Slow Traveling Through Remote Work with Jessica Hall
In this episode, I speak with Jessica who is a Digital Nomad, Travel Blogger, and Content Creator.
Once remote work became an option in their lives, Jessica and her partner, Steven, decided to choose a lifestyle of living month to month in AirBnB’s in different cities/countries.
This way, they get to experience both the comforts of “normal” life while also building in the opportunity and convenience to travel to extraordinary places in their free time.
Jessica absolutely adores documenting travel via her blog, photos, and videos.
Listen on to find out how Jessica has been able to do slow traveling through remote work.
Listen Below:
RELATED EPISODES:
Ep. 296: How This Travel Expert Seizes Every Opportunity To See The World with Gabby Beckford
Ep. 295: How This Tin Whistle Backpacker Lives A Simple Yet Fulfilling Life On The Road with Finn
Ep. 294: How This Social Scientist Created A Free Range Life As A Full Time Traveler with Blake Miner
Transcription:
Debbie:
Hey everyone, thank you so much for being here.
I am so excited to speak with my guest today, I’m here with Jessica.
Hi Jessica. How are you?
Jessica:
I’m good, Debbie, how are you?
Debbie:
I am wonderful. I love your story and I wanted to get you here because I think you had such a great one to tell. Can you tell us more about you and why you live an offbeat life?
Jessica:
Thank you for having me and for your kind words, my story is kind of interesting. We decided after, you know, all the craziness of covid, my boyfriend, Steven and I wanted to incorporate more travel into our lives. He used to teach abroad in China for a few years up until covid hit and I used to work at Walt Disney World in Orlando, where I was feeling like I wanted to incorporate more travel. So, once the two of us got together, we were getting ready to like trying to figure out where we wanted to go. We wanted to go abroad and see more of the world and then once covid hit, we sort of had to take a pause and figure out what we wanted to do, and over about a year-and-a-half of, you know, looking into different options we decided we wanted to do a nomad life and kind of take this new world of remote work on the go so we could not only work and like live a normal life style, but also incorporate travel very consistently.
So, we had like a home base wherever we go and then in our free time, we’ll go out and do travel type things, like go see destinations that, you know, you would always wait and wait and wait to go to, on a vacation, like we thought we would just integrate that into our lives.
So, yeah it’s pretty amazing and I’m still mind-blowing that we figured out a way to do it.
Debbie:
So how were you able to figure this out? Because this is where a lot of people guess talk, like “Okay, we have this idea, how do we actually execute it and make it into a reality?”.
Jessica:
Right, so we kind of broke it down and we got really clear about what we both wanted. Steven is more of a, he likes to live in an area and really like you know, live like a local and I also like to do that, but I also really like the travel aspect of it. So, we kind of came to a compromise in the middle of where we could live in places for about a month or six weeks at a time and then hop to the next one so there will always be something new and then other factors were like sticking, figure out a way to have like financial stability and have an income, so for us, that comes through a remote job, but I know for a lot of people I can come through, you know, if they have the wrong business or you know, working in different lines of business or you know, a lot of people will save up for a long time and do it that way, and yeah, so we just kind of pieced it together and we also, we heard of the nomad lifestyle from some girl that I follow on Instagram named Liz Moody, her and her husband did it in the United States, they would book AirBnB’s for a month at a time and then we thought, “Well, what if we did that abroad?”.
So, we just looked into it and it worked. So, here we are a year later.
Debbie:
That’s amazing and that’s really the planning part is what intimidates a lot of people because there’s so many information out there, right? And also, you talked about making sure that you’re financially stable before you do this because we also don’t want to worry while we’re doing this while we’re traveling and you’re like, “Oh my gosh, how are we going to be able to do this? Because we’re not making any income?”, and I know you mentioned, Jess, that you and your boyfriend do remote work, how did you end up getting a remote job? Because you worked here in Orlando, in Disney and he was teaching abroad, what type of remote work did you end up doing? Was it completely different from what you guys were doing before?
Jessica:
Yeah, it’s a bit different now, we just kind of started looking online and connected with, you know, the right people and you know it kind of fell into place. So, I don’t have the best advice as far as you know, how to get a remote job, I was just kind of was like, you know, asking everyone I knew and looking on every, you know, job website I could think of and the opportunity happens at the right time, so it was you know, kind of everything was orchestrated by the universe, I say, and yeah it just all came together but, I would just say, like, figure out what your skillset is and then start looking for opportunities because there’s a lot more out there than I think we know.
And I know it’s sort of a new thing, but, you know, I’d look into, like, tech companies or startups or I’ve heard of a lot of people, just taking their skills like on social media, becoming virtual assistants, and things like that. Like, there’s, you can definitely make it work. You just have to really set the intention and, you know, it might take some time but it definitely can happen. So many people do it now.
Debbie:
And I think we overcomplicate things and we tend to wait it out, but I think most of it is probably fear, right? Especially if you’re not used to it, you haven’t done it before. But I love that you guys just went out and just started looking, started asking and networking and really looking at what’s out there, because that’s, it’s so simple to do, is just to see what’s out there, “Okay, is that a skill that I need to learn? Or is it a skill set that I already have?”, and then just applying to as many as you can and it will happen and it did for you and your boyfriend.
Jessica:
Yeah, and I’m so grateful every day and I really, I really think it’s because we got clear about what we wanted to do and we kind of set ourselves up with the intention that we were going to leave like, during a specific time frame, so you know before that’ll happen, we had about a year, a year and a half, so, I was you know, sending out my stuff kind of like getting my car sorted, getting rid of, you know, apartment leases and like anything that was tying me to being in the states for the next you know, X amount of time.
So, it was like my life was really going in that direction before I even had the job secured or before I even had plans set in place. So then by the time we figured out, you know, “Hey, we’re going to do the AirBnB route,”, we were able to book like I think only two or three months before, I think we booked everything in July and then we left in October, so, we were ready to go and I think that was really a helpful aspect of it.
Debbie:
Yeah and also doing that, doing things a little bit at a time, so you don’t overwhelm yourself and really preparing for it also helps mentally when you do that, because not only are you making sure that you’re not overwhelmed, but also like your mind is prepared, you know what’s coming and it’s not a complete shock to your system.
Jessica:
Yeah, absolutely, cause I remember there were so many times while I was still working at Disney, where I would be like, “I just want to up and leave and just move abroad.”, like, I would just say it, but it would be so overwhelming that I just would never do it and I got, you know, stuck in my cycle of staying at my job, which was great at the time, but I think it was great that we took a pause on everything, it was kind of a forced pause, unfortunately, with the pandemic, but there was the positive aspect of, it gave us the moment to be like, “Okay, what do we really, really want to do now?”.
Thankfully that was a good thing that came out of it.
Debbie:
Yeah. And it is specially, there’s not just like negative stuff, there’s also a certain things that you can actually do and prepare for yourself during the pandemic, which was obviously, for all of us, it’s like, “Oh my gosh, what do I do with my life?”, especially for people who travel constantly and it’s like all of a sudden your life is in a halt and you don’t know what to do.
Jessica:
Yeah, it’s kind of a weird limbo.
Debbie:
Yeah, absolutely. So, when you finally decided that you are going to do this and you were looking for places that you wanted to go, how did you choose the locations that you were going to live in for a bit?
Jessica:
So, we broke it down, at first we only picked three and we were like, “Let’s see how it goes. We’ll book 3 months. And then if we like, we will continue. If we don’t, we’ll re-evaluate.”, but, spoiler alert, we loved it and did it for 11 months straight.
At first, we kind of just sat down and wrote down, like our top five places we would want to go and once we figured those out for both of us, we just went on AirBnB and we looked at what apartments were available, that way we were able to see, you know, what areas there were good housing opportunities in and like what the price ranges would be. So, we ended up picking Rome for our first one, because Rome had very affordable apartments, which was great. We found one that we just loved and from there, we were able to kind of figure out, “Okay, what is our budget for this?”, and like, “What are we looking for?”, when we are looking for an apartment and then from there, it’s like we kind of learn a little bit each month. It’s like, “Okay, we liked this.”, like, “We shouldn’t have cut a corner here”, like, “This was, you know, give or take whatever.”.
So, after we booked Rome, we also booked Paris and Prague and had those like through the end of the year.
So, we definitely try to make sure we had about three books at a time after you know that stretch went by, so we would always know, have a place to live.
Yeah. It just kind of worked out that way.
Debbie:
So when you’re there you booked your place, how do you balance your work? And also making sure that you see things, what is your day to day schedule like? Because it’s no longer a vacation it’s also a part of your life, but then I’m sure it gets really distracting because you’re in a new city and you want to see things, but you also need to make a living at the same time.
Jessica:
Exactly, so, that’s like the whole game of nomad lifestyle, we call it ‘travel living’ because you’re traveling but you’re also living a normal lifestyle at the same time. So, essentially we set aside, you know, our normal work schedule, so we just do whatever eastern hours, nine-to-five is.
So, that’s like, 2 to 11 in the time zone we were in typically, and then we just work around that.
So, during the weekdays in the mornings, we have free, so that’s the time, we will either of them and I’ll do things around the apartment and we’ll go grocery shopping or we can squeeze in a travel type thing or go to a nearby park to go for a walk, get some exercise, whatever, like life stuff, and then work 2 to 11 and be done with that.
And then, the weekends are really our travel time. So, if we want to do a little day trip or a weekend trip, or just really get to know the city that we’re in, that’s really our time.
And then we also kind of distinguished Wednesdays as our honorary travel day too, like in the mornings there, cause it’s really easy to just work through every single day because, you know, I also do my travel blog and social media content, so, I have an abundance of things to do all the time, so it was nice to kind of have set days were like, “Okay, these are going to be our days to really enjoy where we’re at and be present with this certain location.”, because time goes really, really fast when you’re out there, as you probably know from just vacationing or traveling in general, it’s the same when you’re living there, too.
Debbie:
Yeah. And you know what it is, you think that all of a sudden things are going to be completely different, obviously it is, but having that set routine is so crucial to making this lifestyle sustainable cause otherwise you’re either going to drop off with the work that you’re doing or you’re not seeing anything cause you’re still constantly working.
Jessica:
Yeah, yeah, the routine is the key, I think to the whole thing and that was one of the biggest learning experiences for me and, you know, you go out there and you’re like, “Wow, I have a whole month.”, so like that’s so much time and all the sudden we laugh about this all the time, like we get to the last week and we’re like, “Oh my God, there’s five things we haven’t done. We need to do them all this weekend.”, so we wear ourselves out in the final week and then we’ll get to the next location and we’ll just be exhausted the whole first week, we don’t even like leave the apartment.
So, it’s funny, you know, that’s something we laugh about it, but it’s also like, “Should we try to be a little more intentional and spread it out?”, but it’s, you know, it’s all a learning experience.
Debbie:
Yeah, cause obviously, you don’t want to miss anything and that’s the whole point of doing this is that…
Jessica:
I know…
Debbie:
… you can experience life while you’re also trying to be responsible. I mean, what’s that?
Jessica:
I know and it’s so funny cause we love – our favorite thing is to ask local people for recommendations, but the more you ask them or your list grows and you’re just like, “It is physically impossible to do all the amazing things.”, so, priorities and balance are my keys when we’re out there.
Debbie:
Yeah, have you guys ever stayed at a place and you just didn’t want to leave and you ended up staying? Or is that something that you’re just like, “Okay, we already planned out everything. We have to go.”?
Jessica:
So it’s really tricky with the way that we do it because we do have the AirBnB’s booked, so we can’t really like, adjust them cause you know they don’t really have a flexible policy with that, which is understandable but we did stay in, we stayed in Croatia longer than we did in all the other countries. And I think that was like a subconscious blessing because we fell in love with it there and there was so much to do and if I had flexibility, like cause I know a lot of people kind of plan on the go more so, like I know I would have stayed there longer you know if I had that choice, but yeah it is tricky because you have to kind of lock in because when you’re booking AirBnB’s for a month at a time, if somebody books one day, like you can’t book that unit anymore like within the month, so, that’s why we do it a bit in advance and we just kind of have to lock in and you know, hope it’s a good one.
Debbie:
Oh yeah and you know that’s another thing, it’s like you – it’s great because you can choose the places that you’re going to, but then that’s also the negative, right? You have to make sure that it’s actually a place that you like to stay in or if you fell in love with it, you’re like, “Oh my gosh, I don’t want to leave!”, so it’s kind of like a double-edged sword, but it’s not a bad problem to have.
Jessica:
No, definitely not and I think we have fallen in love with every single city we’ve been to, like every time we leave, we get sad but then we’re also like, “How can we be sad when we know we’re going to, you know the next place that’s going to be so amazing.”, so, it’s kind of an emotional ride that you put yourself on in this lifestyle because you’re just constantly bombarded with new things and you’re falling in love with new things, and you’re learning so much in such a short amount of time. It’s like, it’s like life on steroids, it’s crazy, but it’s really fun.
Debbie:
So, you both do travel a lot slower than certain people. But I mean, I guess like, you know, the monthly thing, does it ever exhaust you? And you’re just like, “Okay, we need to stay somewhere a lot longer than a month because this is exhausting now.”?
Jessica:
Yeah, sometimes we do feel like that. I think the days we feel like that are the travel days when we have all of our luggage and we’re trying to move from place to place. So, we start in October, I think around July, I was starting to get really tired and I knew we were coming home in September. I don’t know, we were talking about, you know, maybe in the future phases, we would stay in places for more like six weeks or you know, two months at a time. I think It’s tricky because I really want to see, like, so many places and I know Stephen does too. So, it’s like, how do you balance seeing everywhere? But also not completely wearing yourself out.
So, I don’t know, I guess we’ll just kind of see how it goes for the future. But for this year, I think it worked. I felt really satisfied with the amount of places we went. So, the monthly worked well for phase one.
Debbie:
Yeah, and it’s also a good idea to do that because then you will see like, “Okay should we come back here? and then stay here for longer?”, and also it could be a good opportunity, I don’t know if you guys want to do this to like, look at places to see if you want to live there permanently one day, you know, like “Okay, we loved this place. I can see myself actually living here for years and not just for a month.”.
Jessica:
Yeah, I know, there’s a whole world out there and so, like, I think I have this like pseudo-life in my head, of me and every single country we’ve been too cause there’s just so much to love in every single one.
So, it’ll definitely be a hard decision when we like decide to pick a place in the future, but I don’t know. But then there’s part of me that’s like, “I love my hometown, too.”, so I don’t know, we’ll just see what happens.
Debbie:
There’s so many possibilities, again, that’s a good problem to have.
Jessica:
It is, I think this whole experience just made me realize like, what a beautiful world we live in, and I know times like the media and everything is so focused on the negatives but when you’re actually out there and you’re seeing these different areas and then just, you know, seeing where local people hang out in the different cultures in the different everything, it’s so beautiful and there’s just an abundance of, I don’t know, everything is so different and it also goes together so seamlessly and you’re just in awe the whole time like I just feel like I was in an eternal state of wonderment.
Just, like I couldn’t believe that, you know, all these places are just existing at the same time as you know, when I’m at home. So, it’s cool to go out there and I just, I feel like I just appreciate life even more now.
Debbie:
Yeah, it’s definitely a whole new world when you get out of your bubble and then you see a completely different place, the people are speaking differently, the food is different, things that you’ve never even experienced before, and it just like, it makes you realize that you were in this little bubble that you had and it was just like popped.
Jessica:
Yeah and there’s just so much out there and that’s, I just feel like any little problems that I had before or whatever, I’m like, “They’re just so small in the grand scheme of things.”, and we just get so wrapped up in it, cause it’s right in front of our face, but I think it was a practice of zooming out and just realizing like, there’s something so much bigger than all of us, and it’s beautiful.
Debbie:
And then when you’re home, cause I know you guys are home right now, how does it feel? Does it feel weird? Like, how are you seeing things from that perspective now? Since you have been on the road for quite some time.
Jessica:
So, I didn’t know how I was going to react to being home but I feel like some days, I’m like, it doesn’t even feel like we left, like, it’s so normal to be here and then other days, I will like look at our pictures and like, “Oh my gosh, like we’ve done so much.”, but I think my favorite thing about being home is just having all of my things here because, you know, living out of a suitcase for a year is really hard to do.
So it’s nice to have all my books back and all of my, you know, my makeup and my clothes, like I just I missed everything but, and it’s nice to sleep in your own bed, too, instead of you know, not knowing where your bed’s going to be like for the month, but I think I’ve just kind of, I’ve appreciated like being with my family and reconnecting with friends and I’ll be excited to go back out though for sure, but I think right now, it’s just kind of nice to take a moment and not be moving for a couple months.
Debbie:
Yeah, and it gives you a new appreciation to life at home when you’re constantly on the road because before you’re always complaining like, “Oh my gosh, I need to be out there.”, and then now you’re like, “Okay.”, there is- certain things that are good about having, home.
Jessica:
Yeah, I know and like I just well, it’s been fall here, so I’ve just been, you know, my wonderment is translating now to my hometown, I’m like, “Oh my gosh, that is so beautiful.”, like I can’t believe how gorgeous it is and like of course it always was but I think I’m just appreciating it more, I think that’s the whole thing, it’s like you just appreciate everything so much more because, you know your time is so valuable because, you know, you’re only here for X amount of time, so which is so telling of life though in general, like, we really only have so much time and we just kind of forget that, you know, things change, as like seasons go by and all that, so, I don’t know, it makes me like slow down for a little bit.
Debbie:
Yeah, and it’s great too cause I think that’s what happens when you’re finally able to see things in a new perspective and also appreciate things that you never even appreciated before cause oftentimes we just take things for granted, you know, that’s there, it’s like, “Oh yeah, fall season. Yes. Pretty.”, like fall colors every year we get them and then you come back and like, “Oh my gosh, this is the most amazing thing ever!”.
Jessica:
Yeah, so true.
Debbie:
When you know, you’re traveling around and you’re looking at all of these different places, like do you, I know you mentioned, you, do you talk to different people and you get local recommendations, but, you know, you book, AirBnB’s a month in advance, do you have an idea of the places you want to go to? Or you just look for cheap places and you go there? and just play roulette, like, how is that like? What is the choosing part now that you guys have done this for quite some time?
Jessica:
So, we kind of keep a note in our phone of everywhere that we want to go and it’ll be, you know, a collection of places we’ve heard of or things people have told us or things we’ve just seen online and we have all the months written out that we’ll like travel for the next year or two and we’ll just kind of plug and play and see what fits and we tried to choose locations that are geographically close together because traveling in Europe is a lot more affordable than you think and especially when you’re in the United States, like you’re paying $200, $300, $400 for flights, all of the time and in Europe, like I feel like the flights we would buy would be less than $150 like a lot of times between like $50 and $120, so, that’s like huge to be able to go from place to place with, you know, such a low cost and that’s not even mentioning trains cause trains are even cheaper than that.
So, if we’re able to see you geographically go to all these different countries but not travel far distance, like that is not only helpful financially but also just energetically like you don’t have those really long, draining travel days so that kind of helps us sway one other thing too, so we just go on like, you know, a normal travelers visa, so, as a US citizen, you can travel within it’s called the Schengen zone, so like the majority of the countries in Europe, you have 90 days, so that includes like everywhere, like France, Czech Republic, Italy, Greece, like all of the main ones you can think of.
So, the only ones that aren’t in the Schengen Zone are like the UK and Croatia, and some of the Eastern European countries and Ireland.
So, we will kind of play that game too, where we only have 90 days within the big section of Europe, so we’ll do three different locations there and then we’ll go to UK or Croatia, Ireland to kind of buffer the time.
So, that’s kind of another aspect to it as well, so, yeah, and you kind of just have to really strategically move your chess pieces so you can see as many places as possible.
Debbie:
Yeah and that’s a really good idea and also knowing all of that, right? Because then you can –
Jessica:
It’s a lot of research.
Debbie:
Yeah, that’s a lot of research and also like understanding when that, you know, 90 days will be up and then you have to go to like England. How long do you stay in the other countries that are not a part of that, so you can go back again?
Jessica:
Yeah, so it’s 90 days, in 90 days out. So, you kind of have to look at it as like a 180 days span. Once you start your time in the Schengen Zone so you can stay 90 straight days and then you have to be out for 90 straight days, and then your time refreshes, so you can go back in after that.
So, we just, we also knew my family was going to come visit us at the end of our time. So we kind of pushed out our time from when we were in Schengen to when we went back, so we could line up our travel dates with them.
So, you definitely want to look ahead if you’re playing that game, cause it’s, you know, a lot of coordinating, but, you know, you just don’t want to mess with border control, you just want it to be nice and clean cut.
Debbie:
Yeah, you don’t want any of that, especially if you’re not in your place, cause I’m like, “Oh my gosh, that’s going to be a whole lot of headache that you don’t want to do.”.
Jessica:
Yeah.
Debbie:
So, just keep all of the dates and get organized for that stuff.
Jessica:
There’s a calculator online too, if you ever need it.
Debbie:
Yeah, that’s super helpful.
Jessica:
Yeah.
Debbie:
Let’s move forward to about maybe 30 to 50 years from now, Jess and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for?
Jessica:
Oh my gosh, that’s such a good question. I think I just would want to be remembered for being somebody who like followed their heart and like what they really felt was right for them.
I just have never really resonated with like the societal timeline and I just really hope that my story kind of inspires other people to break out of, you know, what we’re told day after day and really look inside and see, like what really lights them up, what would bring them more joy in this life and what would make them feel like they lived the most fulfilling life, like, I never want to look back on my younger years and feel like I regretted not taking a risk or taking a chance that I felt really called to, so, I think ultimately, it’s just, I just would really love to have this experience or whatever I do like kind of just inspire people to look within and really figure out what resonates with them and go after their dreams cause life is, life, is really a gift and I really think we need to tune into what our authentic selves really want to do.
Debbie:
Yeah and we don’t know how long we have and I know that said a lot but it’s so true and if this is the only life we’re given you may as well go out and do it, if you can, you know, and also remember like there’s a lot of people that can’t do what you do and have the opportunities that that we have, so you might as well take advantage of that.
So, I love that legacy that you want to leave, Jess, and thank you so much for being here with us today.
If our listeners want to learn more about you, where can they find you?
Jessica:
Yes, you can come find me over on Instagram @JessicaFaye508 and I have a travel blog where I post a lot about our experience nomading, it’s called theroadjesstraveled.com, traveled is with one “L”, and those are the main two areas, I’m on TikTok too, @JessicaFaye508 as well and yeah, that’s pretty much it.
So I would love to see you over there, and I am just so grateful we got to have this conversation today, Debbie, it was really fun to reflect and talk to you about this whole experience.
Debbie:
Yeah, thank you so much, Jess, for being here with us, we really appreciate you and for sharing your story.
Jessica:
Of course, thank you.
Listen to Jessica’s extended interview where she talks about using AirBnB for long term travel.
What you’ll find:
In this extended episode, Jessica gives us valuable insights on how to use AirBnB for long term travel.
