Life of a Digital Nomad: Balancing Work, Creativity, and Adventure

Travel technology is changing so fast that it can feel like you need a new degree just to book a flight. We sit down with Madison Rolley, a travel content creator and entrepreneur with a tech background, to bridge that gap and make modern trip planning feel simple, practical, and worth your time.

Madison shares how studying abroad sparked her travel confidence, how she became a digital nomad at 22, and why moving too fast can burn out even the most excited traveler. From there, we dig into the real reason her audience grew: people kept asking how she could afford it. That question led to clear, repeatable tactics that anyone can use, including price alerts, deal subscription emails, and smarter ways to search when you care more about value than a perfect date.

Then we get into AI travel planning and what is actually changing right now. Madison explains why Google’s AI overviews increasingly pull from video platforms like Instagram, TikTok, and YouTube, and how that shifts the way we discover destinations, hotels, and experiences. We compare tools like Google Flights beta and ChatGPT for itinerary building, including how AI can quickly suggest routes, pacing, side trips, and free activities, while still requiring human judgment to confirm details and avoid bad assumptions.

We also talk about solo travel, the rise in female solo travelers, and how social media can reduce fear by showing real experiences and practical safety context. You’ll leave with a better framework for using travel tech without feeling overwhelmed: start small, ask better questions, and treat AI as a tool that saves research time, not a robot that replaces your instincts.

If this helps you travel longer or travel better, follow the podcast, share this with a friend who’s planning a trip, and leave a quick review so more people can find us.

Madison's Website: https://hoo.be/madisonrolley

Madison' YouTube Channel: https://www.youtube.com/@madisonrolleytravel

Madison's TikTok: https://www.tiktok.com/@madisonrolley

Madison's Instagram: https://www.instagram.com/madisonrolley

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"Wherever We May Roam: Finding Your Travel Style" - On Amazon

Transcript

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Travel Tech Moves Fast

Jim 0:00

Technology is rapidly changing the world of travel. Can today's retirees keep up? Welcome to Wherever We May Roam, the new face of Travels with Jim and Rita. This podcast is about discovering your own travel style to explore the world. I'm Jim Santos, and along with my wife Rita, we've spent more than 16 years traveling. Sometimes for a few weeks, sometimes for a few months, and sometimes a whole lot longer. And what we've learned is this there's no right or wrong way to travel. Some people take extended getaways, some roam part-time, some work from the road, and some make travel a full-time lifestyle. This podcast is about helping you figure out what works for you and how to make it happen in the real world. So whether you're planning your next trip or thinking about something bigger, we're glad you're here. Let's get started.

Meet Madison Rolley

Jim 1:01

Welcome everybody, I'm Jim Santos, joined by my wife and travel companion Rita, and this is Wherever We May Roam. Last week we talked about starting to use AI and trip planning. But are we getting the most out of not just AI, but all of the new tools available for travel planning and finding bargains? Well, today we're turning to the younger generation to find out. Our guest is Madison Rolley, a travel content creator and entrepreneur. After growing her brand while working in tech and traveling the world full-time as a digital nomad, she rebased in Nashville to co-found Sarolay, a boutique community marketing house helping hospitality brands build their crowd, not just their brand. Known for finding the best travel deals and making travel feel more accessible to the average person, Madison now works both sides of the travel industry. Madison, welcome to wherever we may roam.

Madison Rolley 1:49

Thank you so much, Jim. Wow, what an intro. Appreciate it.

Jim 1:52

Madison, I understand you became a full-time digital nomad at the ripe old age of 22. Uh, can you give us a little background of how you got to that point and why you decided to do that?

Madison Rolley 2:02

Sure. So that actually kind of goes even further back to when I was 19 and I did what most college kids did and studied abroad. And

From Study Abroad To Nomad Life

Madison Rolley 2:12

I was in the south of France. I didn't know anyone. It was a completely independent program from my school. I also did not speak French. So it was quite the like leap early on that really inspired my travel bug, if you will. And you know, I learned a lot while I was doing that. That's kind of what brought me to the full-time travel. I was a 2020 grad, unfortunately. So I graduated from my couch. I'm watching, you know, the YouTube video of my name being flashed across the screen. And I was like, okay. But I was really lucky. I did land a job in technology in Santa Monica, California. And because of the timing with COVID and the job starting, they still wanted me to move out to Santa Monica. So I did. And it was, you know, locked down for two years working for my laptop, which was not the experience that I thought I was going to have. I thought I was going to be in office, but it really opened me up to that opportunity of traveling full-time because I was like, there's nothing holding me here. I put everything in a storage unit and took my laptop on the road for my very first stint as the digital nomad, which lasted about five months. It was a little crazy because I was like jumping from place to place like a week every single week, which is not sustainable. I honestly would not recommend that unless you're really young and are full of energy, uh like I was, because I got burnt out very, very fast.

Jim 3:36

Yeah, I can imagine. We we've had some trips where we moved a little too fast.

Madison Rolley 3:40

Yeah. I get that. It's so hard to figure out good pacing in travel. Like sometimes you just you're like, I want to hit everything. And I think there's value in both, but gosh, you can really wear yourself out sometimes.

Jim 4:04

Well, I think you you may have been suffering from something that happened to us too after COVID. After being trapped so long, not being able to travel, I think everybody kind of overcompensated.

Rita 4:13

Right. It's like a racehorse jumping out of the gate, you know.

Jim 4:17

Yeah.

Rita 4:17

Absolutely.

Madison Rolley 4:18

I was like, oh, let me go. Right. I was itching. I was like, I got this travel bug is really, really kicking up.

Jim 4:26

We were just now you started out, Stan, doing like cold call work in Santa Monica. How did your brand evolve? How did you uh change from that to what you're doing now?

Madison Rolley 4:35

It's interesting, it all kind of weaves together and it's something that is very dependent

The Video That Went Viral

Madison Rolley 4:40

on the story behind it. Otherwise, if you see my resume, it kind of doesn't make a lot of sense. But basically, I because I was able to work for my laptop, I was able to, you know, cold cut Fortune 500 CFOs who did not want to hear from me, especially during COVID from anywhere in the world. I decided to, you know, take the laptop on the road. And when I did that, I had a lot of friends that were like, How are you affording that? Like, is it your parents? Is it like the sugar daddy? Like all these crazy accusations of like me being way wealthier than I was. I was right out of college and the company I was working for wasn't paying me much. And I was like, no, no, no. I just I learned all these tips when I was studying abroad. I learned, you know, certain travel tools that I just thought was common knowledge and realized it wasn't because of all the questions. And then people were really interested in learning more about those. Um, this is just like, you know, friendly talk at a party. It wasn't anything I hadn't really dabbled in the social media world too much yet. So after getting enough questions, I was like, okay, I need to like make a video or something explaining this that I can just send rather than re-explaining myself so often. And I made that one video and it brought me my, I was I was shocked, it brought me my first 30,000 followers. I actually ended up crashing the brand I was talking about's website, like just overnight, a realization that so many people did not know about something as simple as like setting up travel alerts or like setting up for a travel alert subscription.

Jim 6:14

Right.

Madison Rolley 6:14

So that really opened the door into or just really locked me into. There's a personal brand to be built here. There's opportunity to teach people something that I'm really passionate about. And so I did that all while being in tech. So I actually only stepped away from the technology world and like having a full-time like remote nine to five in October of last year. Yeah, it was kind of a crazy adventure of building my personal brand all while still doing that. But it was really cool because I was able to transition from the world of business development and sales into marketing, which was always something I was really interested in because I was building my personal brand. And the company that I left back in October really saw the value in that and let me transition into content marketing on the business to business tech side. So that was really exciting.

Jim 7:05

And is your content marketing all on travel-based industries, or do you kind of spread yourself across the field?

Madison Rolley 7:10

Yeah, so it's actually funny. Like the content marketing I was doing for the business-to-business software company was not travel-based at all. Now, the company itself was based in the UK. It was, they had a New York office. They had me traveling a lot. It was actually like an address verification software. It wasn't shiny, it wasn't interesting. Right. But it was kind of a platform or a launch pad rather for myself to realize this marketing, the content marketing side of things, I've learned a lot through creating for myself and my audience and through the personal brand. And then kind of with that, I really learned I had a special skill set in not only understanding because of my tech background, like algorithms and how AI is changing the way that people are consuming their content. And also just changing the way they're traveling. There's just a lot of things that I learned that when I did decide to step away from the tech industry, I really knew I wanted to lean into continuing to build my acumen in

Why Hospitality Marketing Feels Stuck

Madison Rolley 8:10

the content marketing space, but also do it with hospitality brands. And that actually comes from an origin of really loving experiential brands because my parents actually own a candy store in my hometown. And so they were the very first social media account I truly ever managed. Um, and like I brought them an Instagram when like businesses weren't quite doing Instagram yet. And I actually recently retook them on as a client and we've had a lot of success there, which has been really fun to see because that was where I started basically. But I think having that background in helping my folks start that business and what tourists were looking for, what like really makes an experiential brand special or like a destination special when you visit it. So I just wanted to do that for more brands like the candy store or like some of the most incredible hotels and bars, and I don't know, all these like incredible businesses that make my travel special. I wanted to be able to help them because I saw there was really a gap in the basically from like how social media worked in 2016 to now, a lot of the hospitality industry is still operating like it's 2016 and like scratching their heads of why it's not working and why they're not getting eyeballs on their stuff.

Jim 9:29

Right. Well, I think it had a couple of big advantages. The first one don't think we should overlook is that studying abroad really opened up the world for you. I mean, we have a granddaughter who spent her senior year in Denmark. She's one of a triplet, group of triplets.

Madison Rolley 9:44

Oh wow.

Jim 9:45

And the difference between her and her two siblings is just night and day.

Madison Rolley 9:49

Yeah.

Jim 9:49

So you had that advantage of having the world opened up to you, and of course, already being in the tech world. And you're at the right generation also to have social media play such a big role in what you're doing. How much has that social media influence helped you with developing your brand and with helping others?

Madison Rolley 10:05

Oh gosh, so much. I think there's a few things to be said in what you just shared. I really think it's so like my opportunity to study abroad helped me in so many ways past just, you know, getting the world opened up, but like really the confidence to do something scary, you know, like in independence, like taking a leap into entrepreneurship or putting yourself out there. I think that's a layer of it too. Like when you study abroad, you kind of have to just let yourself be in the world. And you're, you know, you're not getting sheltered by your parents or your college. Like you don't, you don't really have anything to grab onto. You just kind of have to like be like, okay, this is me. And I hope the world responds well to me. And that's very similar in content.

Social Media Makes Solo Travel Safer

Madison Rolley 10:50

I think social media, you know, it gets a positive and negative reputation. I will say, in the way that I use it, in the way that I create, I really think it's an opportunity for education. And even I remember even when I was like studying abroad, I mean, social media wasn't really being used as an educational tool too much yet, but I still was like looking in Facebook groups, I remember, of like people's experiences with certain study abroad programs and different living different places, like that that community. I I think social media from a travel lens really gives people an opportunity to make traveling, especially solo traveling, less scary. I always use the term finding your expander, whether it's travel or building a business or whatever it wants you want to do. I think social media is a really great tool to find maybe someone that's like a step or two ahead of you. Maybe they're like 10 years older than you, and you're like, wait, if they could do that, I feel like I could do that, you know, and like use them as that inspiration of like, okay, how did they go about that? And I think that's the really cool thing about social media is there's so much to be shared, and so like so many people are sharing their experiences and tools like I share, there's so there's just so much out there from an educational lens that I think is making travel a lot more accessible, whether it be just in doing the thing or even just financially as well, in the way I teach.

Jim 12:16

The tools that are available now, even just 10 years ago, right? It was much more difficult to travel.

Rita 12:22

Well, and and you can actually pull up people's experiences of the country that you want to go to, you might not have the same experiences they have, or might not feel the same way, but at least get your foot in the door of what to anticipate.

Madison Rolley 12:37

Absolutely. And that actually brings up a really great point because so I've most of my travels has been solo traveling, and I think as a woman, a lot of people are like, Are you scared? Like, are you are you do you feel safe? And I think with social media, there's been such an emergence of female solo travelers sharing their story, and even further, I think the proof is in the data. I actually went to Google's office in New York back in April with a few other travel creators, and they shared some really interesting statistics from the year, and one of those was a severe increase in female solo travel, which I think is incredible. And I think a lot of that is because solo travel as a woman, even now a little bit, is a little taboo, or people like just really question you if they aren't the ones doing it. And I found that a lot in my travels, especially when I was younger. But to have to see other women doing that online, I think can be very inspiring and very empowering. Yeah, we've interviewed quite a few.

Rita 13:42

Yeah, and actually, I used to solo travel one gym and we hadn't met, and I just yeah, I've never been afraid, thank God.

Jim 13:51

Yeah, and really our granddaughter that stayed in Denmark for a year, she was really a pretty timid person.

Madison Rolley 13:57

Very.

Jim 13:58

But after a few months in Denmark, she's taking trains to other countries in Europe, yeah, and going by herself and doing that, and just you know, extremely confident about that kind of thing.

Rita 14:09

Speaking in in groups in Danish.

Jim 14:12

Yeah, learn to speak in Danish.

Rita 14:14

Yeah, I mean, here she wasn't 19, she was 18.

Jim 14:17

Yeah, when she started, yeah.

Rita 14:19

Yeah, yeah, and she had to learn the language and you know you know how to present herself. And it was quite an experience.

Madison Rolley 14:28

Like I was very lucky. My mother always told me stories about how she would sneak off to Paris and only tell her brother, but they didn't have social media or cell phones or like or like maybe a cell phone, but you know, if you didn't hear from your daughter for a few days, it wasn't like raise the alarms. Like I had friends my expander a little bit, and I was really lucky in that. And I had cousins that had studied abroad, but I think if you don't know anyone that does it, like, oh gosh, social media can be such a a world opening.

Jim 14:58

It can be. Yeah, her mom was actually pretty apprehensive about the whole deal, too. I think we're we're a bad influence, they blamed us.

Rita 15:06

I think you're a great influence because every place we go, oh, can we live here? Sure, we can live here. Every place we go, we do that.

Jim 15:14

And we brought them out to visit us when we were living in Ecuador, right? Too.

Rita 15:17

So they loved us back into the Andes.

Jim 15:21

Yeah, once you start seeing places around the world, you start realizing that it wasn't the big deal that you thought it was.

Madison Rolley 15:26

Absolutely, and that people are nice and lovely everywhere. Like, I think the number one thing that people told me when I was about to study broad in France is that French people were mean. You know what? I really did not have that experience. And I now I just joke. I'm like, okay, it's because they only went to Paris, and at the end of the day, Parisians are French New Yorkers. They're not mean. They just don't want to deal with your tourism.

Jim 15:49

They're not mean, they just don't care. Yeah. Now I I'm a geek too. I worked with computers and networks the last 20 or so years of my working life. Last week on our show, we talked about how we started using AI to help planning some of our more complicated trips. And you've worked directly with uh Google, beta, and open AI. How do you see AI changing the way people discover travel and what should creators and brands do about it right now?

Madison Rolley 16:46

Oh gosh, I think it's already changed the way people are like just even if people don't even realize it yet, I think first off, it this is my I just have to like say everyone should be using

AI Changes How Trips Get Discovered

Madison Rolley 16:59

Google Flight Alerts or not, sorry, Google the cheap flight beta feature.

Jim 17:03

Uh you know, I looked at that and I looked at their AI thing, but for the the what we were looking for, it wasn't particularly helpful.

Madison Rolley 17:10

But I will say, if you're looking for because I I get so many people in my audience asking me for very specific routes on very specific dates, and I'm like, okay, that's not that's not usually the best way to travel cheaply, but I always defer to now the Google Flights beta. It really is if for people that don't feel super comfortable searching for affordable flights on Google flights or that kind of intimidates them, I think it's a really great tool for finding cheap flights or making that a little bit more accessible. And then just in the way we travel, it's already changed so much just because of even if you search on Google, you get your AI overview, which is now a lot of people don't realize that those AI overviews, one of the highest prioritized pieces of content that it's pulling from is actually Instagram and TikTok videos, which that's not the way it used to be. It used to be a lot of blog content or yeah.

Jim 18:06

If you do a search on Google now, you see the on the little AI thing there, you see the little symbols for Instagram and YouTube and all flyby as it as it looks through it.

Madison Rolley 18:15

Yeah.

Jim 18:15

Yeah.

Madison Rolley 18:16

It's really interesting. So a lot's being pulled from video content specifically on social media platforms. And I think that's one thing that generally has also just changed the way people discover travel. I've noticed social media is that's like the first or second place people will go when they're looking into a trip because they want to see a video about people's experience, kind of like we were talking about earlier. I think also there's I think a lot going to be coming out in the travel space that will help with afford affordability with AI, but I could also see, you know, with AI, we already have like dynamic pricing with you know, flights and hotels on Google. And so I feel like that will only continue to get smarter. So there could be advantages, there could be disadvantages in the travel space. But I think overall, in the way people will travel, I don't think people will realize how much it will change without them realizing in the background, is the biggest thing that I've noticed. Right.

Jim 19:17

Yeah, I think there is a lot going on back there that is kind of invisible to most people. And yeah, you know, not everybody is a geek like me will actually get an AI tool and use it for a variety of of uses.

Madison Rolley 19:31

Exactly. I do think, I mean, one thing, so one thing about me, which is was something that was so fun. So right when Chat GPT came out, and this is kind of what spurred the partnership with OpenAI, right when it came out, I you know, started playing with it because I'm a little tech nerd, and I was like, okay, I want to see if maybe it could help me like plan a cheap European vacation. And so I asked it to plan a two-week European vacation from I think Nashville to wherever and just get me under get me there and back and through the whole vacation in under like a thousand bucks or something like that. And I was really appalled with like how it was able to spit out you know, budget estimates and give me different routes that I could take that right, you know, I could really, you know, do it affordably and on the cheap. And so I shared that with my audience, and that went a little bit crazy on the internet and I've been getting a lot of press about it. And I ended up on Ryan's Secret Press. That was really fun. But it was really cool because then I ended up taking the actual trip. And I will say it was a little off. Like I did spend over a thousand dollars, but not much over, I will say. And I think that was also half of my own fault because at the end of the day, it's like you're gonna spend on food or souvenirs or you might splurge for a little bit of a nicer, cuter stay. Uh, it just depends on the traveler. But I was really impressed with how it helped me curate an itinerary, and I think it'll continue to be great for itinerary planning, especially with I would say I really like Google's AI now. I feel like it's a little bit more accurate, a little bit more up-to-date, and also just location aware further than something like Lauder Chat GPT. But yeah, I think I think it is such an opportunity to travel smarter and better and cheaper. Exactly. Absolutely.

Jim 21:42

And we you know, something we stressed in in our show about this was that you have to also remember that it is a tool. Like you said, it's sometimes it's a little bit off. So we're we're not quite at the point where you can say, go ahead and book all my travel and you know let me know when the car is picking me up, and you know. But it was extremely helpful. You know, what we did was briefly was we told it we had fifty-three days. We're starting in Madrid, we're ending up in Hamburg, Germany. Here's a list of thirteen cities we'd like to see in between there. Recommend the amount of time that we should spend in each one. I think we also gave it the parameters that no air travel, we only wanted trains and buses, and no trips longer than six and a half hours.

Madison Rolley 22:23

Right.

Jim 22:24

And within a minute or two, it had spit out fourteen pages. Spit out all that information. Complete with tourist sites in each of those cities that we might want

Testing AI With A Budget Europe Trip

Jim 22:34

to see and recommended side trips.

Rita 22:36

Yeah, yeah. That we hadn't thought about.

Jim 22:38

Yeah. So yeah, so that was really useful. Now we modified that a bit.

Madison Rolley 22:42

Yeah.

Jim 22:43

But that alone saved me a couple of days of looking up information.

Madison Rolley 22:47

Absolutely. I think especially in the research phase. Oh yeah. Oh my gosh, it saves so much money. Even if it's like, yeah, like you said, even if it's inaccurate, it at least you get started on a right on the right path. It's similar to, you know, if you asked it to help you with an email or a research paper or something like that. But it's gonna probably not have the best word. Like the your voice is gonna be stripped, it's gonna sound a little wonky, but at least it's giving you a direction of maybe how to format it or how to like certain points that you might have not thought to hit, like you said with the side trips. I think it's really fun for discoverability. And then you get to do your own research from there. Like, oh, I haven't heard of that town, and let me go look on Google, let me go look on Instagram on what that might look like. Yeah.

Jim 23:31

Now it sounds like you you basically have a mission of helping your audience travel smarter and be kind of like travel insiders. How are you how are you going about that now?

Madison Rolley 23:41

Yeah, so initially my mission, and this is something I've always done in my content. Not a lot of content creators necessarily form a mission for their content, but initially I really wanted to is I think it was like help people travel without breaking the bank, which because everyone was like, you know, travel's expensive. That that was the resounding narrative. And I was like, it actually doesn't have to be. I mean, it depends on the way you like to travel. Sometimes it can be expensive, but it doesn't have to be, you know, this one trip you take a year that's super expensive. I wanted to break that narrative. And then, you know, as I traveled, especially because that when I started my channel, I was gosh, 22, 23. And as I traveled, as I built my career, as I've grown up personally, it's like there's certain things I've come to appreciate. And I that's kind of where that travel as an insider narrative came along. Cause I'm like, sometimes it's not just about doing it on the cheap, but like maybe getting a better bang for your buck or like a better experience because you need what questions to ask or what tools to use. And kind of overall, I just want and I think this comes from growing up in like a smaller town and being surrounded by you know, friends, some family that like didn't necessarily understand that I don't know, like that if you opted into something like traveling or something that felt maybe a little bit more luxurious, or I don't know, it doesn't, it didn't necessarily mean that you were loaded. I don't know how to explain that any better. But it's like I wanna, I wanna open up the world to people. And I think the biggest, I mean, the biggest catalyst to that is travel, but even in like smaller things of just understanding that you can have all these really beautiful and cool experiences, and it might not even be that much or it might even be free. You just didn't have the questions to ask. And so I just want to open people's worlds and give them the tools so that they can go live a more elevated version of their life that they may not have thought that they could have. And that's been kind of what I've sought out for myself. And so kind of sharing those learnings as I go.

Jim 25:46

Yeah, no, a lot of people you like you mentioned, they want to travel, but they feel like it's financially out of reach. What are some of your tips for consistently finding the best travel deals?

Madison Rolley 25:55

It depends on the level of traveler that I'm speaking to. Um and you'll see that even in my content. Like some content's a little bit more broad, some content is a little bit more in the week. And I would say just from like a high level, learning things like setting price alerts or signing up for those deal subscription emails. I think those are really big door openers because then people start getting emails that say, Hey, you know, flight to Italy for under $300. And you're like, wait, what? You know, I can't I can't even get to one state over for that. So those I would say are very big. Also, from a hotel perspective, again, setting up, you know, Google just released the hotel deal alerts, so you can also get alerted when hotel deals because they fluctuate in a similar way that flights do. And then also there's a new tool that I recently discovered called VIO, and they have these like deal freezes that they literally go in and book on your behalf. You don't have to put down a credit card or anything, but they literally go book on your behalf, and if you freeze their deal, and then if the hotel goes down, they'll go cancel that and book again for you. And so you're getting the guaranteed lowest rate on the hotel before you go. And even if you freeze the deal, you don't have to like they'll just cancel it if you get, you know, a day out and you haven't actually gone. So it's no liability on your end, but you're getting a guaranteed secured spot on a lower rate with a hotel. So that's another one that I love to share with people.

Price Alerts Hotel Drops And Deal Tools

Madison Rolley 27:33

It really just depends on the way that people like to travel. I kind of give a little bit more tailored advice.

Rita 27:38

Yeah, and and that's what it is. You have to build your trip uh in your own parameters on what you enjoy and what level of accommodations you want, etc.

Madison Rolley 27:51

Absolutely. And also just like people's technical understanding. With my degree, I have a management information systems degree. So I know how to code. I can talk to a software engineer very technically. I can also talk to someone who has absolutely no idea about technology at all. So I think that's a lot of how I approach giving feedback because a lot of what I share is in the tools and in the tech. So you'll see a lot of my most well-performing videos, I speak very as non-technically as I can about something technical. And then if we want to get really like in the weeds of really, you know, some real travel hacking and let's go to all these different websites and kind of the nerdy stuff, those don't tend to get the most views, but I feel like that's also speaking to the maybe the more advanced traveler, the more technically advanced. And I think there's value in both.

Jim 28:43

Yeah, we know people who need to have like every minute planned out, need to have a tour group for this and tour group for that. And then there are people like Grita and I who will just show up and look around and take off at something that looks interesting.

Rita 28:55

Yeah. And I that's how I travel. I'm very like, oh, we'll just walk out the door and see what we find.

Jim 29:00

Yeah, look at that.

Rita 29:01

And we find that half the time we can get in absolutely free, like when we were in London and we had to listen to an organ recital at St. Paul's. Okay, let's do that. And then we're we're in rather than spending 60 bucks per person, you know, we listened to music for 30 minutes and we got to view the church.

Madison Rolley 29:22

Absolutely. And honestly, every time I travel, that's something I like to do kind of a mix. Like I always have one or two things that I know I want to go visit, like a different thing. And then the rest is kind of walking around. But one thing I really have loved with AI is you know, telling it that I'm going somewhere and that I don't I want to spend the least amount of money, and it gives me recommendations of psyching experience for free. And I I really love that that's now an opportunity rather than searching through like a million blogs, like kind of all say the same thing.

Rita 29:54

Yeah, because some museums are open are open for free on certain days of the month.

Jim 29:59

Or at senior discounts that aren't really advertised, right? Or student discounts.

Madison Rolley 30:03

Like I remember when I was studying abroad, the Louvre, I think it was a certain day that was like a student day and it was free if you had your student ID.

Jim 30:10

Yeah, in Paris at least, I think all of the museums, students could get in free. And if you were a person in a wheelchair, you got in free, and the person pushing you got in free.

Madison Rolley 30:18

I think you're right. Yeah, accessibility.

Jim 30:20

We we had a saying that we've brought up a couple times here that no no matter where you go, there you are. Right? The the one thing that's in common whenever you travel is yourself. You've always got yourself with you. What do you feel like you've learned yourself? How have you changed personally from your travel?

Madison Rolley 30:35

Oh my gosh. So I left that question because in school I was extremely type A to the point where I'd give myself panic attacks. If things like I was like control freaky, like I if I things didn't go the way I had planned in my head, I just really had a hard time with it. And I didn't even realize it was that was what was I was having a hard time with, but it would lead to like panic attacks and like really high anxiety. And I think through traveling, I think also COVID kind of had it's like you know, all these pattern disruptors of being like, well, you just gotta roll with it because it's nothing's changing and you're just here. But I I really found solace in traveling, especially solo traveling, because I think you know, being a part of the generation that has all this technology and social media, you're not alone with your own thoughts as much as you know, I think you would have been before. And I think that can lead to a lack of understanding of yourself and your values and who you are, really, because it's like you're getting fed all this a lot of ideas of who you should be or could be.

Jim 31:46

You're lost in the noise, yeah.

Madison Rolley 31:48

I and I think also like I I've noticed I really love like overhearing people's conversations. Like, I if I'm at a restaurant, I love just sit there and just hear what everyone's talking about.

Jim 31:57

That's Rita.

Madison Rolley 31:58

Yeah, yeah, I take it all in. Yeah, yeah.

Jim 32:01

I could care less, but that's Rita.

Madison Rolley 32:03

Yeah, so I really love traveling to countries where I don't speak the language

Travel As A Reset Button

Madison Rolley 32:09

or I speak it very minimally, because it you really are alone with your own thoughts. And typically when I'm traveling, I'm not on my phone half as much, mostly because of the data decision. It's like I don't want to be spending all my data usage, and so I'm kind of forced to be alone with my own thoughts. And I really feel like some of the most transformative moments in like my career and in my life, like decisions that I felt like I needed to make and kind of moments that I just really had strong intuition about any given thing came a lot during travel. Now it's like I try to recreate that even when I'm here in Nashville. Like yesterday, I spent, you know, a better part of like three hours painting in my backyard, unplugging, being just with my thoughts, maybe some nice music, or and I really think that's helped me in my direction. Like, I don't know if I would have made career moves that I would have made, or even you know, physical moves to moving to Nashville or anything like that, if I didn't have not only my world open, but the time with my own thoughts that travel allowed.

Jim 33:16

Uh, what's the best piece of advice you can give to people of our generation for using technology and social media for travel?

Madison Rolley 33:23

Be patient with yourself when you start.

Jim 33:25

Yeah.

Madison Rolley 33:26

I think it can be really frustrating for anyone, but I I've noticed with my folks when they started, I try started trying to show them AI and stuff, they'd get a little frustrated. But and then it's just it really is one of those things that you just gotta kind of start and be a little patient initially, and then you'll start, you'll start really realizing all the questions you can ask. One thing I'd love to tell people specifically with AI, and I got this actually when I was at Google because I just loved the way he worded it. One of the, I think it was one of the project managers for the AI search tool. He was like, the best thing about travel with you know Google's AI feature is you can just put in your hopes and dreams and it'll spit out what you're looking for. So I just I always tell people, put in your hopes and dreams. Don't just stop at the parameters that you're used to searching. So like I need to go to Nashville from or I need to go to LA from Nashville, and I need to go on these dates and put in kind of like a free write. Like, you know how like an English class when you were a kid, like they were like, just write anything that's coming to your mind. I literally tell people to do that. Just it's it feels wrong in the way that we've been taught and like basically programmed by these companies to search for things, but just free write, like tell it all of your hopes and dreams for your trip for your vacation and just see what it comes back with. You can always modify it.

Jim 34:48

Yeah, I've noticed in using AI myself that the more I use it and the more I talk to it like you would normally talk, yeah. It knows you, it kind of gets to learn what you're interested in and what you're not interested in. And uh it's really interesting. I see why some people develop kind of an unhealthy relationship.

Rita 35:05

Yeah, I can't.

Jim 35:06

That's a little scary.

Madison Rolley 35:07

Yes, I agree. Absolutely. And that's something I you know, yeah, I think that's something that I also heed a warning to people. It dep it depends on how much you're using it, specifically for travel. But there's probably gonna get to a point where you've used it enough times where it knows you're it does it's gonna recommend things that might not push you out of your comfort zone. So, like maybe even asking it, can you push me out of my comfort zone?

Jim 35:32

Right.

Madison Rolley 35:32

Or make some recommendations that would. Because I think that's one of the most incredible things about travel is you go and try things you maybe would have not tried before because you heard about it from someone somewhere, you know, but the AI knows you and it knows what you do like, what you don't like so well after a certain point that maybe you wouldn't take a trip that would be a little bit more out of your comfort zone because you didn't know enough about it. And I think there is still value in that.

Jim 35:59

Was there anything that you wish that you had known when you first started out as a traveler?

Madison Rolley 36:03

The world is not as scary as it seems on TV. Oh, 100% I think that's the biggest one. I think, I mean, again, I grew up in a pretty rural town. I didn't have a lot of experience traveling internationally. Yeah, I don't

Hopes And Dreams Prompts Plus Wrap

Madison Rolley 36:18

know. I I saw a lot on the news specifically, talking about certain countries, and I don't know, I just feel it it made the world seem a lot more big and scary than it is, really. And the more I've traveled, the more I've realized the world is like so much more small and people are way nicer.

Rita 36:36

Everybody wants the same things. They want to be able to take care of their families, take care of themselves, and just enjoy life. Everybody wants the same thing.

Jim 36:45

Have you ever uh had a moment on the road, uh, one of those aha moments where it's just like, man, this is exactly what I should be doing?

Madison Rolley 36:52

So I took a trip to well, this is like kind of still around COVID times, I would say 2021. I got a flight alert for I think LA to Rome, and it was only $320 around trip. And I just went and I literally just Googled, this is pre-AI, I Googled day trips from Rome. I wanted to like go somewhere just rural and like kind of escape and just have like a true small town Italian moment. I went for two and a half weeks and I chose Bolsena Lake in Italy, which is like kind of in between Rome and Tuscany, I would say. And I just every single day I would have a slow morning, I'd make my breakfast, I'd make my coffee, I would walk down to the lake, I'd journal, I'd go to the coffee shop and have another coffee. It was just like very, it was a lot slower pace, a lot less noise. And I think that was kind of my aha moment in I would say work-life balance and what I prioritized in my life. Of it doesn't all have to be quick and now. And I think that was really big for me because of my history with like anxiety and kind of control foriness of like, okay, I'm kind of creating my own anxiety through feeling like I have to get everything done right now. And so just it was kind of commitment to myself that I would be intentional about taking more slow moments, whether I'm traveling or not. Living kind of that Italian, you know, French, just slower, enjoy the moment type of lifestyle.

Jim 38:35

Well, we've been chatting with Madison Rolley, a creator and entrepreneurial leading voice at the intersection of travel and technology. You can find out more by going to https://hoo.be / MadisonRolley, following her on Instagram by checking out Madison Rolley, and @MadisonRolley for TikTok. And of course, all those links will also be in the show notes. Madison, thanks again for taking time to bridge the generation gap with a couple of older and but fellow travelers.

Madison Rolley 39:01

Thank you so much for having me. It was a pleasure.

Jim 39:04

Next week we'll be speaking with Paul Partridge, a man who started out as a financial planner and gradually found himself as a travel writer and photographer, who now helps people get the most out of their travel and the connections they make. Until then, remember we travel not to escape life, but so that life does not escape us. If you've been thinking about traveling longer or just traveling better, we hope this episode gave you a few more ideas. Remember, there's no right or wrong way to explore the world. Only the way that works for you. If you enjoyed this episode, be sure to follow the podcast. And if you have a moment, leave a quick review. It really helps more people find us. And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, paperback, and audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at Jim@ jimsantosbooks.com. Thanks for listening, and as always, safe travels wherever you may roam.