The Traveler’s Mindset: Turning Travel into Personal Transformation with Kelly Tolliday

Episode Overview

Travel is more than just an escape from the day-to-day grind. It is a powerful catalyst for personal growth, offering lessons that extend well beyond the journey itself. In this episode of Life Intended, I had the pleasure of speaking with Kelly Tolliday, a wellness travel expert who embodies the philosophy of intentional travel. Our conversation illuminated the profound impact of cultivating what she calls a “traveler’s mindset”—a way of approaching life that emphasizes presence, resilience, and the ability to pivot when faced with challenges.

Understanding the Traveler’s Mindset

Travel offers us the opportunity to step outside our comfort zones, experience new cultures, and see the world from different perspectives. However, the real magic happens when we apply these experiences to our everyday lives. The Traveler’s Mindset is built on four pillars: beginner’s view, presence, perseverance, and the ability to pivot. Each trip we take is a lesson in these areas, and when we bring those lessons home, they can significantly impact our personal growth.

  1. Beginner’s View: When we travel, everything is new. We're thrust into unfamiliar environments where we’re forced to adapt, learn, and sometimes, even fail. This beginner’s mindset—being okay with not knowing everything—allows us to see life through fresh eyes and reminds us that it’s okay to be a novice at something, no matter our age or experience.
  2. Presence: Travel demands that we be present. Whether navigating a bustling market in Thailand or savoring a quiet moment in the Swiss Alps, we’re fully immersed in the experience. This presence can be transformative if we bring it back to our daily lives, helping us to engage more deeply with the world around us and appreciate the simple moments.
  3. Perseverance: Travel rarely goes as planned. From delayed flights to unexpected weather, there’s always something that challenges us. But these challenges teach us resilience. They show us that, despite setbacks, we can keep moving forward, adapting to circumstances as they come.
  4. The Ability to Pivot: Perhaps the most crucial lesson travel teaches us is the ability to pivot. Plans change, and we must change with them. This flexibility isn’t just useful when our vacation itinerary falls apart; it’s a valuable life skill that can help us navigate everything from career shifts to personal relationships.

Applying the Traveler’s Mindset at Home

So how do we take what we’ve learned on the road and apply it to our daily lives? The first step is intentionality. Before embarking on a journey, set an intention for your trip. What do you hope to learn or achieve? Is it relaxation, self-discovery, or perhaps strengthening a relationship? This intention-setting not only guides your travel experience but also helps you integrate those lessons into your life back home.

For instance, if your goal is to cultivate presence, find ways to practice mindfulness daily—whether through meditation, journaling, or simply taking a walk without your phone. If your trip taught you the value of perseverance, remind yourself of that strength the next time you face a challenge at work. The Traveler’s Mindset encourages us to see our lives as a journey, where each experience, whether at home or abroad, is an opportunity for growth.

The Importance of Community in Integration

One of the most powerful ways to keep the Traveler’s Mindset alive after your trip is by staying connected with the community you built while traveling. Whether it’s fellow travelers you met on the road or locals who touched your life, keeping those relationships alive helps reinforce the lessons you learned. At R & R, we make it a point to maintain these connections long after the trip ends, using tools like WhatsApp groups to share reflections, journaling prompts, and even the occasional travel meme. This community support is crucial for integration—turning what was a vacation into a lasting transformation.

Integrating the Lessons from Travel into Daily Life

The real magic happens when we bring these lessons from our travels back home. Integration, as Kelly puts it, is where intention meets action. It’s easy to feel enlightened and rejuvenated during a trip, but the challenge is to carry that mindset into our daily routines. This might mean adopting slower mornings inspired by a relaxed vacation pace or continuing a practice of mindfulness that was deepened during a retreat. It’s about making conscious choices to live in alignment with the person you became on your journey, even when you’re back in your everyday environment.

In essence, adopting a traveler’s mindset is about seeing life itself as a journey. It's about being open to new experiences, learning from every situation, and being willing to adapt and grow. Whether you’re navigating the streets of a foreign city or the complexities of your own life, the principles of presence, resilience, and intentionality can guide you to live more authentically and fully.

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Episode Transcript for The Traveler’s Mindset: Turning Travel into Personal Transformation with Kelly Tolliday:


Kelly Berry (00:00) Hi friends and welcome back to Life Intended. I'm your host, Kelly Berry. Life Intended is a podcast that explores what it means to be true to yourself and live an authentic and purposeful life. Each episode explores my guest's version of personal growth, self -discovery, and the pursuit of becoming the best version of themselves, as well as how to find the joy in the journey. I'm excited today to have a conversation with Kelly Tolliday. Kelly is a wellness travel expert, retreat facilitator, travel advisor, and podcast host of Transform with Travel. She's also a 500 hour registered yoga teacher and an accredited continued education provider for the yoga industry. She is the co -founder of RNR, a boutique retreat and travel company, guiding you on intentional travel experiences in the world's most breathtaking destinations. Through their organized group tours and retreats, custom travel advising services, as well as retreat management and facilitation for coaches, businesses, and communities, RNR is your one stop shop for all of your travel needs. She is married to her husband, Sam, and is a mom to two beautiful girls and two crazy dogs. Welcome, Kelly. I'm excited to chat with you today.

Kelly Tolliday (01:16) Thank you so much. I'm so happy to be here.

Kelly Berry (01:19) Yeah, so tell us a little bit about, you know, I know I just read your bio, which talks about who you are professionally, but talk a little bit about who you are personally, how you got into doing what you're doing, how you got here.

Kelly Tolliday (01:34) Yeah, so I mean, travel has always been a massive part of my life. I grew up in a family that valued travel and we didn't do a lot of international travel, but just anything from camping to going out west to having staycations down in the Keys. based here in South Florida, so we're pretty lucky to call so many amazing destinations home. But I grew up in a family that valued travel pretty much above all else in terms of like material possessions and stuff like that. And they, My parents, they had a lot of experiences in their own childhoods as well as through college and post -college where they lived overseas and they had really crazy adventures and they always made sure to tell us those stories, almost like bedtime stories. So I grew up as a kid feeling as if like I was a part of those adventures already. And so for me, it was kind of like a no brainer that I would eventually fall in love with the world of travel, but through my own experience as a young adult venturing off into the world on my own, I just realized there was a really strong component of travel that was more than just ticking off your bucket list or seeing the sights or even relaxing. There was a really strong catalyst for change within my life with each and every trip that I took. I met my husband while we were traveling. We were both traveling through Ireland. That was a massive catalyst for change. I moved to Sydney post -graduation and pretty much took me on a completely different trajectory of my whole life. And so I realized that travel had such a power to change your life just by observing the cultures, by allowing yourself to be perhaps a different version of yourself that you might not have allowed yourself to be in the constraints of your own hometown. And at the same time, I was falling in love with the practice of yoga and meditation and really kind of digging deeper into uncovering who I was and my true nature and peeling back the layers of who Kelly was. And I found through combining these two things of daily wellness and yoga and meditation, which got deeper and deeper when I would travel, because I didn't have the daily obligations at home that were kind of pulling me out of those meditations. I found when I gave myself those spaces to be in a different environment and also apply the practices that were allowing me to be my most favorite self. That was where magic just truly began to form in my life. So I wanted to create a space, a community, a business where I brought all the best of travel to people without our community having to worry about the logistics and the TripAdvisor reviews and planning the flight and doing the this. Like we take a lot of that overwhelm off your plate so you can really step into the full joy of travel. And I just feel so grateful every day to be doing this work that I do.

Kelly Berry (04:04) Mm -hmm.

Kelly Tolliday (04:18) I have an amazing business partner for our business R &R and being able to do that together as well as my own business, Transform with Travel, which is, I have a podcast all dedicated to travel. I have custom travel advising and planning. So it's just like, even though I'm at home, I still feel like I'm like adventuring every day because I'm in this space. And yeah, that's just a little nugget about me right now. We'll get into more, I'm sure.

Kelly Berry (04:41) Yeah, yeah. I love the way that you said your most favorite version of yourself. Because I think, you you hear like the best version or whatever, but I think it's really important to, your favorite version. Like, who do I like to be? What do I really like? So I like that you said that.

Kelly Tolliday (04:48) Yeah, I saw that on Instagram recently, so I really can't take credit for it. But that made me just really think about it because I recently got asked on a podcast, what would you say to your 18 year old self? And I answered like, you're so cool. How fun is this? How fun is life right now? Talking to my 18 year old self and I realized like, yeah, I was definitely not the best version of myself when I was 18, but I was having a shit ton of fun. And that's like a part of me that I love. And so I'm trying to bring more of that into our into our group discussions and our journaling and more of the transformation work that we do on travels talking more about like, yeah, that that favorite part of yourself, because I might not always mean that it's, you know, the best version where you're waking up at 5am and meditating every day. Like, that's not always realistic. But there is a real reality of being able to be your favorite self, no matter what that looks like.

Kelly Berry (05:42) Mm -hmm. Yeah, and that's a big part of what I'm trying to help people uncover with the podcast is there's an authenticity, I think, within all of us that we maybe lost touch with or don't really pay as much attention to as I think we would all like to or maybe would serve us best. And so just thinking about it, even that like different phrase, I think is really helpful to differentiate because the truth is like...the best version of myself like may not be the one that I like the most. yeah, yeah. Or want to spend all my time being. So, yeah.

Kelly Tolliday (06:21) Right? Exactly. Exactly. Sometimes the best, my best self is really boring. Like I want to go have some fun.

Kelly Berry (06:29) Yeah, exactly. Yeah. So I know that you have talked, you you really take travel and this intentionality and put them together, but, for yourself, but for the people that you work with also, and you've kind of coined a phrase called the traveler's mindset. So talk to me about what that means and how you apply it or how you help people understand what that is.

Kelly Tolliday (06:58) Yeah, so I always say that what you learn on the road, whether you're traveling from city to city, state to state, or country to country, you get to cultivate this sense, as you said, a traveler's mindset and really being able to have this lens in which you view your life as a traveler, even when you're at home.Oftentimes when we're traveling and again, it doesn't have to be international travel, but you're thrust into a new situation and you're thrust into new smells and sounds and communities and languages sometimes. And you really get to apply the sense of a beginner's view. Like you're starting something new, you're learning a new language, you're cooking something new even at home. And we don't get oftentimes a lot of chances in our life as an adult to. Apply being a beginner to anything when there's some sometimes there's fear around starting something new and not wanting to look stupid Sometimes there's just not time to start anything new like every minute Sometimes of every day is filled with things that we have to do for others if you have a family if you have a business all those things so traveling really allows you the opportunity to be a beginner just in and of itself. Even if you've been to the same country a thousand times, you just get to view things with new eyes. And so that's a really important piece of cultivating a traveler's mindset is allowing yourself to be in this beginner's mindset, be in this beginner's view. And usually you're okay with like messing up a couple words in a new language that you're trying because you're giving yourself some slack because you're a beginner. You can apply that to your day -to -day life and not taking every single thing so seriously and not having to be perfect at every single thing. So I think travel really helps you get a sense of that first and foremost. The next thing that I think travel really helps that helps you cultivate that traveler's mindset is, like I mentioned, you're thrust into new environments in some countries. Like if you go to India, like you have to be there. Like you cannot go on autopilot when you're in India or when you're in Thailand or when you're somewhere and sometimes in South America, like even in New York City, like you have to be every single step of the way there in that moment. So I think a traveler's mindset also helps you cultivate a lot of presence, not going on autopilot in your life, being truly present with where you are and being okay with that, that that might slow you down a little bit, because you might have to look at your directions a couple of times to figure out where you're going. Like applying that to your daily life as well helps bring you a lot of peace within your own life because you are being present. And then there's two more things here and I don't want to go on and on, but the third thing there is about perseverance and resilience. As we know, when you travel again, whether it's city to city, especially with children or country to country, a lot of things will come up along the way. You're out of your comfort zone. There are challenges that come up. There are things that go on plans. Like I've definitely been in situations where I've had a six month plan while supposed to be on the road and it got totally flipped upside down. And so, The sense of being able to cultivate perseverance and resilience despite what's happening around you is another thing that you learn on the road. And then the last and what I think is the most important thing that cultivating a traveler's mindset and how to apply that to a successful life, whatever success means to you, is the ability to pivot. And it kind of goes hands in hands with perseverance and resilience. But as things come up, you might realize that you need to make a pivot or a change or adapt to a new situation in your life, at home, on the road. And the ability to pivot is truly, in my opinion, of success. Like how you are continually able to feel successful, and might not look successful to other people, but how you're able to feel successful in your day -to -day life and something that you learn very quickly and very often when you're traveling is how to pivot. In motherhood, in business, in travel, in relationships, pivoting and accepting that pivot, I think, is like so important. And so I could go on and on about what you learn, but cultivating a traveler's mindset and how to apply that to your day -to -day life, I think is one of the most important takeaways that you can take on your trip. And that not many of us are being super intentional about when we do go travel.

Kelly Berry (11:10) Yeah, especially the presence, know, and then there's, think that also goes with perseverance and the unexpected is how you respond. And I know that's coupled with resilience, but, you know, I just think the scene that comes to my head is an airport when there's weather or when, you know, we're a few weeks from the big computer issue that was going on people's attitudes and the way they handle those things and the emotions and all of that. That seems like it would be a big part of it too. basically being able to make lemonade out of lemons or something like that and not letting these things that happen make you into a version of yourself that you don't want to be. Yeah.

Kelly Tolliday (11:38) Yeah. 100%. I always say like, travel is very similar to having a child. It is a true mirror and a very like, like responsive rapid mirror to your stress levels. And that's not to say that I'm perfect when I travel that I'm just like serene and calm and like nothing can bother me. What I do do though is when I do have let's say a tampered a temper tantrum over a canceled flight or a hotel room not being the exact one that I booked. I will let myself have that tantrum if I have to like if I'm really feeling overstimulated and dysregulated, there's really nothing I can do about that in the moment. But I do take time after to kind of reflect like, okay, what was my default emotion? Did I just go like directly into anger? Was I not very kind to that hotel clerk? Was I like kind of not being super judgmental about myself, but kind of just taking a step back and being like, Whoa, okay, this is an interesting reaction that I just had to that stress actually I see how I do that to my husband when I'm home and he hasn't done the laundry or I can see how I do the same thing to my kids when they're being too loud. Like you're able to take that pressure cooker of stress that travel can be sometimes and really see how that might look like in your day to day life as well too. And then hopefully over some time and some work and with coaches like myself and yourself, like being able to come up with strategies to mitigate and or prevent that reaction from happening every single time that something comes up.

Kelly Berry (13:19) Mm -hmm. you know, my husband and I talk about this a lot, you know, if you can Sometimes it's tough when you have those experiences and you you feel like I wish I didn't have the that experience or I wish I didn't have that reaction but if you can like You know flip the script a little bit and just be like, well, that is one more experience or one more time that I have to reflect upon and figure out how I was, why I was, and how I want to be. If you can kind of look at it like I won't say as a gift because sometimes that that's kind of hard to take too but you know it's another rep that you have under your belt where you've gotten to kind of flex these muscles, use them, and to this you know scenario you can apply them from one area of your life into so many others whether it's motherhood or work or whatever. And every rep that you have in situations like that just helps you handle the next one even better. And so I think that's really important, but you have to, you have to understand that and you have to be willing to think about it in that way. You know what I mean? Yeah.

Kelly Tolliday (14:23) Exactly, exactly. It's that intentionality piece and a little bit of a little bit, a lot of bit of self awareness that does come with building your reservoir of tools and strengths and journaling. And there's so many things that can go into it. But yeah, it's a self awareness piece to start with. Some people just have no idea that they're flying off the handle and then literally don't think about it ever again, which it would be a beautiful place to be in ignorance. No, I'm just kidding. I totally kidding. But

Kelly Berry (14:30) Right. Yeah

Kelly Tolliday (14:52) But yeah, I agree with you 100%.

Kelly Berry (14:55) Yeah, so you mentioned you had an experience where you had like a plan for six months that got totally derailed. talk about that. And I know you kind of use the traveler's mindset or, you know, maybe even in retrospect, we're we're like introducing yourself to that. So what was that situation like?

Kelly Tolliday (15:15) Yeah, I would say this situation is what was the catalyst for me to start considering that these travel experiences were more than just travel experiences, that these were catalysts for growth and change. So back in 2018, my husband and I, my husband's Australian, we were boyfriend girlfriend at the time. So we weren't married yet. Actually, we were married on paper. We just hadn't had our wedding. So I digress. He was my husband. Back in 2018, we decided we were going to, we were in the process of getting his green card for the United States. We were living in Sydney. We decided, why are we just waiting around in Sydney? Let's go travel again and wait for our green card while we're on the road. So in 2015, we lived in Thailand for a year. We were teaching English and kind of traveling all abroad, across, overseas in Southeast Asia. And we decided that we wanted to go back to this little island off of Lombok, which is just north of Bali, called the Gili Islands. loved, there's three islands, Gili Ti, Gili Air, Gili Menno.We loved Gili Air, it was like this diving Mecca and you could walk from one end to the island to the other in 30 minutes. No cars, there's just horses and carts and stuff and bicycles. And then we just loved it. So we had a plan, July 2018, we were gonna go to Indonesia and live there for about four to six months, depending on how long it was gonna take for my husband to get his dive master certification. He was really into diving.And I got a job teaching at a beautiful open air shala in the middle of the islands. And it was like dream, like literally dream life, like diving every day and teaching yoga on a little island in Indonesia. Like chef's kiss, couldn't ask for anything more. Supposed to be there till the end of the year. My friends literally booked tickets to meet us in Bali from the United States, meet us in Bali for New Year. So we were planning on being there July to December. We got to Gili T for like about a week to celebrate my birthday. And then we got to Gili Air, checked into our villa, call it Malumbung in Bahasa in Indonesia, and checked in. had one night, I was very, very sick. I had like really, really bad case of a stomach bug. I was considering going back to the mainland to go to the hospital. It was so bad. And my husband came home from his dive master and he was gonna go out to get some beers with friends, but decided to stay home to study. And while I was in bed upstairs, we felt this massive earth shattering shake basically. And it was a huge earthquake that was hitting the island. And long story short, it was middle of the night. We didn't know if there was a tsunami. We didn't know like what was happening. We had to run to the middle of the island. Slept in open air, basically in a paddock open air with other travelers. We didn't know, again, no cell service, so we didn't have any warnings for tsunami or anything like that. A couple of days later, we got evacuated by the military and we're told basically like, have to leave this island. It's only business owners and locals that are living on this island now. And we were like, okay, where do we go? Like, what do you mean? Like all the flights were booked out of Lombok, because every single traveler on Lombok and Gilear, thousands and thousands and thousands of travelers are trying to leave.So we just booked the only flight that we could get out of there and we went to Borneo. It was the only flight we could get. Went to Borneo for a couple of days, went to the hospital to get myself checked out. And then we ended up finding a flight to get to Singapore. And from in Singapore, we just took ourselves probably like three or four days to kind of be like, all right, what are we doing now? What do you mean? Like, I have no idea what we're supposed to do right now. And so it ended up being, again, like, One of the worst things that have ever happened to me and also one of the best, we ended up going to India, we ended up going to Sri Lanka, we ended up spending three weeks road tripping through Western Australia, all places that I just didn't think was gonna be possible for us on that trip. And we learned a lot and we grew a lot and we processed and a lot of grief. But the main thing that I realized was that I was really struggling with this fear of this failure, basically. I had this plan. I posted about it on social media. I was supposed to be a yoga teacher on an island in Indonesia. Like that was the plan, right? And I totally got upended. I kind of went through all the of grief, trying to reconcile with what this was supposed to look like and also coming to realize that maybe not never, but at least for a very long time, that plan wouldn't actually come to fruition at all because I was going to be too concerned going back to Indonesia with the earthquakes and stuff like that. So all of that to say, like that was kind of the catalyst for me to start realizing like there is so much more than just learning a new language or going on a zip line in a jungle, like surfing an XYZ location, like that the growth truly happens when you step out of that comfort zone and the universe surely gave me a big step out of my comfort zone with the earthquake, but I learned, I totally cultivated a sense of learning how to let go of those plans when they don't come into plan and like how to pivot and how to be okay with that pivot. It took me a very long time to figure that out. But I think since then I keep getting better and better at being okay with things not going the exact way that I think they should, which is a massive lifelong process for me, but something that that particular experience taught me very deeply.

Kelly Berry (20:39) Yeah, yeah. So how do you take those lessons and apply them to your everyday life? And I know you're a mother, how do you think about modeling that for your children or teaching them or talking about it? What does that look like for you all?

Kelly Tolliday (20:57) I mean, we travel a lot with them, so we're kind of able to show them through experience. I mean, I think it's just about trying to be as open and transparent, age appropriately with them as possible. Like even something as simple as, hey, do you want to go to your friend's house this afternoon? And then my friend's messaging me saying, hey, actually, like, we can't do that today. But now my three year old is dead set on going to her friend's house. So it's like, how can you rewrite that narrative just a little bit to get her excited about something else? And so what they talk a lot about with toddlers is like the art of distraction or kind of repositioning something that might need to change because their brains like literally can't comprehend changing a plan once they're on that track. And so it's just like for me, I'm like, okay, like we can't go over there today, but we said we can go over Saturday, right? So it's like, okay, the plan might not be today, but now it can be a different day. And but now we can go outside and go paint. And it's like the same thing as adults. We can do that for ourselves. Like, OK, we were supposed to go on this tour through whatever Florence, but it's raining every single day in the next week. And they've actually canceled all the tours. And you're really bummed because you really wanted to see the statue of David and you really wanted to see like all these things. And you're like, but there's actually a train that's heading up to Chincaterra and there's no rain over there. So do you want to just like change that up and change where we're going. Or if you're at home, like same thing. Hey, I was supposed to have a podcast interview with XYZ celebrity and they had to cancel, but now I have this opening for me to really double down on my website that I really wanted to work on over the past few weeks anyways. And so it's not to like shove your feelings under like this toxic positivity thing, but it's just like allowing yourself to be like, damn, yeah, that kind of sucks. Hmm, okay, but where's the pivot and being able to move towards that pivot without holding on to what's quote unquote supposed to happen.

Kelly Berry (23:01) Yeah. So one of the things that you said about your six month plan and the stages of grief, and I've talked about this in a couple of other podcasts, but I think it's important for people to realize the morning of things that you expected that didn't come to fruition and how real that is and what that feels like. how do you handle that? Because that's a those are big emotions and big feelings and that can happen in life, in travel, in health and all kinds of things. So what's your approach or kind of like strategy for dealing with something that's like deep, you know?

Kelly Tolliday (23:45) Hmm. Yes. I think that came to mind when you just said that got full body chills was for me, my breastfeeding journey. I was like full blown holistic, everything pre -baby, like you were going to do this and the, you know, all the things that you get told you're supposed to do. And breastfeeding was one of them. And I was like, I don't even think I had bottles prepared. Like I was like, we're just going to breastfeed, of course. And it didn't work. It just like physically, emotionally, like did not work. And I like,

Kelly Berry (23:58) Okay.

Kelly Tolliday (24:13) I spiraled really deep into that because it wasn't even so much that I wanted the breastfeeding. It's like I wanted to stick to the plan and I made myself sick over it. So in terms of strategies, my main teacher within yoga and meditation, his name is Mark Bredner. He's amazing. He's actually living in Bali in Indonesia. The main thing that he always talks about is the right practices, the right mentors and teachers and the right community.

Kelly Berry (24:20) Mm -hmm.

Kelly Tolliday (24:42) And I love that because it doesn't prescribe one particular thing. It just means what are the right practices for you? For me, breath work, journaling, getting outside and getting space from technology, travel, those are my best practices. My right mentors and teachers, I've got my coaches, I have my therapist, I have my acupuncturist. Like who is in your arsenal of your mental and physical healthcare team of maybe it. Maybe right now you're in a stage of life where you need a business coach. Maybe the right mentors and teachers is working with a travel advisor to help bring your travel dreams to life without all the stress, right? Like whatever that looks like for you. And then the right community. We all know the power of community. We especially felt the lack of the power of community during COVID. So I think we hold onto it so much tighter now. And again, that could be your surfing community. It could be your yoga community. It could be your business networking community.

Kelly Berry (25:22) Thank you.

Kelly Tolliday (25:38) And all of those things might look different at different stages in your life or even different areas of your life. But that's to me is instead of prescribing like the specific strategy that it took for me to get over my breastfeeding grief or my living in Indonesia paradise grief or grieving, you know, one of our best friends passing like it's always coming back to, okay, I have these three buckets where like, what are those gonna be those three things for me? What are my right practices? Who do I need to reach out to for support from a professional's perspective? Because friends and family are great, but I really do think having professional support with an objective view is super important. And then who's the community I'm going to rely on for this particular challenge? And again, that might look different from my breastfeeding, from travel, from business. Like that community is going to look different. So I think if you can apply that lens of those three things to whatever challenge or whatever grief or whatever heartbreak you're dealing with, then you're able to kind of be a little more selective about what you're doing rather than some Instagram influencer telling you that a 5 a routine is gonna fix all your problems.

Kelly Berry (26:44) Yeah, yeah, yeah, I've never heard that, but it makes a ton of sense. And really, to your point, like it is applicable no matter kind of like the grade of grief, because it comes in a lot of forms and it's basically just unmet expectations. And it can be, you know, it can be the loss of a friend because you had so many expectations for the future and, you know, the relationship was really important or it could be health diagnosis, you know, what that implications are for you, for your family, or it could be, you know, you had this really fun vacation plan, but then a tropical storm came through and now you aren't going to be able to take one for another year. So I think that I really like that. And I think that if the awareness is there to realize that like grief comes in a lot of forms and really, you know, it's that you had this idea of what something was going to be like and when that idea doesn't come into fruition, stopping to take some notice of what you're feeling and what you need and then having the tools that you talked about to be able to work through that, it's just, I guess it's all part of that pivoting. It's like this expectation wasn't met and I need to pivot, but also I need to handle it and figure out how can I move through it with as much like grace and looking at it as learning experience and, you know, using it as a contributor to how I want to be going forward.

Kelly Tolliday (28:21) Yeah, and like I said, those three buckets, practices, mentors, community, it doesn't mean that they're gonna be like 33 % across every single time. Like yesterday, I had a really challenging day with my girls. Like by the end of the day, I texted my husband, I was like, you need to come inside, like from his office, and I need to take the dogs for a walk. But my practices, like I wasn't gonna journal my way out of that when I have a three -year -old, like mommy, mommy, mommy, mommy, you know? But what I did was luckily I had an appointment with my therapist last night and it wasn't even, it was just coincided that it was a tough day and an appointment with my therapist. But after that session, because she could see it from a bird's eye view over things that we've been working on since the earthquake, she's been my therapist since the earthquake, that, she was like 80 % of the bulk of me moving through that. Whereas other days, 100 % of it could just be me taking a couple deep breaths. So it's just knowing that like it doesn't have to be relying on all three of those at any given time. It's just knowing that those are tools available to you.

Kelly Berry (29:12) Yeah, and taking the time to figure out what the tools that work for you are. you know, like journaling may not be it for everybody. I do think some form of breath work is it for everybody, at least, you know, initially to be able to like get re -centered. you know, taking some time to figure out like what are those things for you, just like you would for who is this community and who are these teachers. Like, you know. what do I need to have in my toolbox so I can handle these things when they come up, because they will. Yeah.

Kelly Tolliday (29:53) Exactly. We talk about this in, I have a, we could talk about it later actually. I was like, that's old. It's just this, I have this ebook called The Mindful Traveler and we talk about different strategies to help you get from travel stress to smiles. And one of the things is writing your trigger list and like, what are your strategies? So like, I'm triggered by X and what's my strategy for Y? And it's like, that's kind of what you're talking about is like, getting curious about what are your tools and then being clear about that, maybe writing it down, having it in a note section in your phone, because when you are dysregulated or you are going through a stage of grief or whatever. It's hard to know when you're like, pick it out of your brain as it's happening, but it is easy to just flip open the notes in your phone and be like, okay, I see these four different strategies and that one seems like the best to me. So getting clear on that and actually writing it down rather than it living up in your head. Cause your brain, your control center is going to shut down when you're feeling dysregulated. You're not going be able to access that higher level of thinking, but in the notes in your phone can do that for you and you'll have that available for you.

Kelly Berry (30:35) Mm -hmm. that makes me think also of, you know, I talk about this sometimes with goal setting. When you set a goal and travel is just a perfect example of this. Like thinking about in advance, what are the things that are going to get derailed? You know, instead of thinking through, I'm about to take this trip. It's going to be amazing. I'm going to be the weather is going to be perfect. I'm going to have all this downtime. What are the things that could prevent that from happening? And if you just take a little bit of time and think through, well, you know, the weather could be really terrible or I may have booked this upgrade, there it's booked and they have to put me in this crappy room or, whatever. But if you just take a little bit of time and like get out of the fantasy of what the perfect experience is going to look like. Then when it happens to you in real time, it's not the first time you've thought about it. And so you have to your point about like, you know, these areas of your brain that won't be accessible, at least you will have like the experience of thinking through it in advance. I think that can be a really helpful practice because if you're setting goals and you're basing your progress to goal off of this very perfect linear path, the first time something doesn't go your way, that's when you're like, you know, Well, I guess I just ate a cookie. I guess I'll wait and restart this diet next Monday instead of already thinking about, like if or when I eat a cookie, like how am going to respond to that? Like what am I going to do? Am I going to put off my diet till next Monday or am I going to like approach the next meal the way that I want to approach it? And so yeah, it was just making me think about that when you were talking that way.

Kelly Tolliday (32:24) Exactly. Yeah, totally. And we were talking about like fantasizing and romanticizing how everything's gonna be absolutely perfect and then it doesn't happen. And then the flip side of that is a lot of people get really anxious or stressed or overwhelmed about travel and they don't allow themselves to talk about it because travel is supposed to be the Mecca of feeling amazing and relaxing. So then when we keep those feelings of those anxieties in, then it makes it feel a lot worse when we're able to just say it out loud. Like, I'm really anxious about child not sleeping on this trip. Instead of just like holding that in and then it happening and then exploding because it happened, you know, it just, I'm really nervous about my child not sleeping on this trip. So my strategy for that, if it does happen is this. And so it's like saying it out loud helps deescalate the anxiety in our own mind. Or perhaps you still feel anxious about it, but now you have a strategy because you let yourself kind of visualize that happening. Or, like you said, the weather, weather's a huge thing in it. Like I get really stressed about hurricane season and traveling during hurricane season. We're going to Costa Rica next Friday, like literally the peak weekend of hurricane activity, like historically. And so you know what? I just told the owner of the villa, I said, I'm really nervous about not being able to leave because of hurricanes and weather. What's the refund policy and can we apply it to a future date if there is no refund policy? And we found out the answer to that and I feel really solid about that response and I feel okay with it. Boom, okay, if we can't go on that trip, well, at least I know I can reschedule. And so it's like letting yourself kind of just let yourself go there into that anxiety, but then with an approach of trying to find solutions ahead of time.

Kelly Berry (34:06) Mm -hmm. Yeah, yeah, productive anxiety or yeah, yeah, So I know you and I talked a little bit about strategy travel as a strategy as it pertains to your life. And I know you've got some thoughts on this. if somebody's looking to, know, travel is important to them, they want to make sure like travel is contributing to the life that they want to have. Like, what are some ways that they can think about that or plan or pick destinations based on that?

Kelly Tolliday (34:22) Yes, yes. Yeah, totally. So it kind of goes back to this word we've been saying a lot is the intention behind it. And so, you know, a lot of us think vacation and we think relax on the beach and just get a lot of relaxation and relax some more and relax, you know, just like, that's like all we're really thinking about. And it's like, okay, well, if that is the sole intention of this trip, like you are on the verge of burnout, you need to get away, you need an escape and relaxing is your core like intention behind what you want to get out of this trip then that should inform a hundred percent where you go. Maybe it isn't all inclusive. So you literally don't have to open your wallet up. Maybe it's a really remote deserted island in the Caribbean that you just want to like shut off from the world and your cell phone won't even work. Or maybe your intention is a little bit deeper than the relaxing and you want to uncover what that is. So I have some journal prompts in that the mindful traveler ebook that I have on my website. There are some journal prompts to help you kind of uncover What is my like real intention behind this? Am I really feeling really stuck and uninspired in my career? Is my relationship kind of going through a little bit of a rut and maybe this trip can re -inspire us as a couple? Do I feel like I rely on so many other people in my life and feel a little codependent with someone in my life and I wanna go adventure on my own and figure out who I am on my own? Am I going through a divorce? Am I about to be an empty nester? Do I wanna bring my kids and show them the world? Which is a completely different trip, completely different activities. So all of these things help us inform where, how long, who, with what we're doing, right? And so it doesn't mean that every single thing that you do on this vacation has to revolve around this intention, but it can help you figure out what to say yes to and what to say no to when you start planning. Cause I know I'm sure everyone listening on this trip knows what it's like to be like, I'm going to Barcelona. And then you start actually figuring out what you can see in Barcelona in three days. And then you're like, my God, how am I going to do this all? Then you try to see it all and you try to do it all. And then you feel burnt out just from the trip, right? We need a vacation from the vacation. And so that intentionality piece, depending on what your intention is, helps you inform, okay, how much free time do I want to bake into this to just have a really slow morning or sit at a cafe for three hours and just journal?

Kelly Tolliday (37:11) How much time in my schedule do I wanna allow for complete spontaneity? Like maybe there's a full day that you actually haven't planned anything, which I fully recommend to everyone who's traveling more than four or five days. To be able to be in the spontaneous state of who do I meet and what do they tell me to do? And I met this traveler in the hotel and they have this sneak peek place that I get to go to. So getting really clear on what your intention is and what you wanna get out of it really helps you get your ROI out of the trip and be really clear about, yeah, again, like where you wanna go and what you wanna be doing with your time and that who you wanna go with piece is very important. Cause oftentimes we think it's a given that we have to travel with our partner or we have to travel with someone else. And that's not necessarily the case. Like solo female travelers, I think it's like 48 plus years old is one of the biggest demographics of travelers right now. It's one of the biggest trends that we're seeing is like 48 to

Kelly Berry (37:50) Mm -hmm.

Kelly Tolliday (38:11) Yeah, like really 48 plus, 50 plus solo women, not single women, just solo women who are choosing to travel by themselves, whether that's voluntarily or involuntarily, is the biggest demographic and trends of travelers happening right now. Like travel agencies and hotels and operators around the world are shifting their marketing for this. So it just goes to show that like you have the choice in how this travel experience kind of unfolds, not necessarily what happens, what weather you're gonna have. You can't control all of that, but the intention piece behind it. And then that kind of helps you see some of the silver linings when things happen that aren't in your plan. Like let's say your intention is to really immerse yourself in a slow living culture and learn how it feels in your nervous system to slow down a little bit. And then I don't know, you have a tour planned in Greece. you know what? This is a good example. We were in Greece as a family. It was Father's Day. We were supposed to go on a sailboat tour around Paros and the weather was really bad. And our travel agent who we worked with was like, I don't really recommend like going around Greece when it's a little bit rainy. And I was like, well, we're from Florida, right? We know all about rain. We're okay. And we had to push the sailboat later in the day because of tides and weather and all that It actually was one of the most beautiful experiences, because pretty much every day we had something lined up in the morning, and it allowed all of us just to slow down. My parents went for a really long walk. I got to just connect with my children and have a normal, quote unquote, normal morning like we would at home, like wake up, have breakfast, hang out, instead of pushing them to be on the go. And we got to have a really slow morning, which is something that we wanted to have on that trip. So sometimes things unfold or happen that can suck in the moment. But if you have that intention piece, you can almost like silver lining it a bit and like transition and pivot your mindset towards maybe that it's happening for your greater good. Of course, there are things that happen that are tragic, like, and we don't want that to, we don't wanna smile our way through that. Like there are real things that happen, but like 90 % of the time, there are things that we can kind of mold into our intention to help us for our greater good.

Kelly Berry (40:26) So when you travel and you are in a new place, like what is your favorite way to kind of like take in a new place or get your bearings?

Kelly Tolliday (40:37) I love walking. So I want, first of all, if you're going into a different time zone, whether it's just to Florida and Nashville, which is what our difference, yeah, an hour difference, like getting outside as soon as possible when you land is one of the most important things you can do for your overall health when you're traveling, because when you get outside in the morning or in the afternoon, your eyes are adjusting to the different spectrum of light which helps you trigger melatonin at the appropriate time to go to sleep and stay asleep. So it helps kind of combat jet lag. And these are other like tips that you'll get in the mindful traveler ebook, stuff like that and how to combat sleep. But for me, I love being on the ground. love walking. I love going to local parks, which is something really fun to do with the girls. Like we're kind of forced to find the best parks around the world because you need your child to just go to a park and run.

Kelly Berry (41:24) Mm -hmm.

Kelly Tolliday (41:27) But because you're going to local parks, like you're able to kind of see communities at their most fundamental levels. And I love when we're like without children, me and my husband love to get, we love to rent a motorbike and just motorbike around, but still it's motorbiking and cycling and walking still have that kind of on the ground immersive experience rather than seeing it from the car window or an airplane, which have their time and place if you're trying to get from one place to the next really fast. But when we get immersed in the community, I love just taking a long stroll or hopping on the back of a motorbike and just really seeing like another example of Greece, guess, is we hiked from the port all the way up to the top of the Hora, which is the top of the town on the mountain and this island, Seraphos. And we were literally passing people's little houses, little windows that were open, and we were smelling the food and the fragrances from the flowers and hearing this old Greek couple yelling at each other. Perhaps they're just talking with each other, but that sounds like yelling. But like that, to me, you get to peer inside someone's real life and almost like feel what it would be like to be there, like what the difference is and what you can learn from that. So walking, I think, is one of the best things that you can do. I love taking food tours or street food tours, because usually they'll take you to some really awesome local experiences. And then the last thing is talking with people. Go to your barista at your cafe and say, hey, where would you go tonight for dinner if it was you and a group of friends? And nine times out of 10, they're going to tell you somewhere that you can't find on TripAdvisors. So be OK. It goes back to that beginner mindset. Be OK with nothing accepting that you don't know this place and somebody else knows it more than you and asking for help and getting their opinion on.

Kelly Berry (43:11) Mm -hmm. Yeah. So do you do a lot of pre -planning, tour planning? you, are you like more blank slate, figure it out when you get there? What's your strategy?

Kelly Tolliday (43:27) Yeah, I like to have a loose plan. So I will have a Google Sheet. I will have an Excel sheet itinerary and you know, I'll make it pretty. And I like to do some pre planning ahead of time just so we're not sitting around being like, well, what do you want to do? What do you like? I like to have some intentionality around that. And I will do like, like, like day one, a p day two, a p And then I'll have like dinner recommendations.but I'm very fluid with, okay, well, the weather wasn't great for that, so let's shift that to another day or let's just nix that hike altogether because this local told us about this traditional spa house that we should go to. So it's like having the pieces in play, but being very okay with shifting around that. And with kids, I mean, I travel with my kids a lot like that. I mean, you gotta be okay with being flexible and...learning to be okay that you didn't see the 12th temple of the day because your kids just don't care about it anymore. So yeah, I think a loose plan is definitely one of the best ways that you can go when you travel. Of course, people that travel that feel a little uncertain or it's a destination that requires a lot of pre -planning like, you know, if there's a lot of museums that you want to go to or there's a lot of national parks you need permits for or like a Peru, we're going to Peru next April with R &R, my retreats business, we're spending eight days in Peru. Like, of course with our retreats, everything is planned very intentionally. But if I were to go to Peru by myself, I would probably wanna make sure that either I'm working with a local tour operator or everything is kind of pre -planned only because I know that there's so many like pieces that can shift and change there. So yeah, I think loose plan is always like a great way to go leaving room for spontaneity, but also not leaving enough, not leaving enough space where like, or maybe not leaving enough, not planning and spending an hour or two every morning trying to figure out what you're gonna do, because then that's just wasted time.

Kelly Berry (45:27) Yeah, yeah, yeah, and draining on everybody. Yeah.

Kelly Tolliday (45:31) Exactly. And then you're like fighting with, you know, what do you want to do? you I keep I remember we were traveling with a bunch of my friends and it was like, I kept finding everything and I was like, guys, like, please help me. And they're like, we thought you like to do this. And it's like the miscommunication piece can cause frustration. So like a little bit of like a group effort can can go a long way.

Kelly Berry (45:49) Mm -hmm. Yeah. So one thing that I was thinking about as you were talking about, you know, being able to pivot and shift things around. You know, I think about people who plan these trips and they spent a lot of money and they prepay for things and then weather interrupts it. You know, like, I guess what's your advice to be able to be like to plan those things so you have the most flexibility so you're not like, well, now I'm really mad because I can't go on this thing that I paid a fortune for and we're maxed out on budget and you know then that brings up a whole other set of emotions besides just disappointment.

Kelly Tolliday (46:22) Totally. Someone that people can look online is who's really good about this is someone called, her name is Erica Wasserman and her brand is Your Financial Therapist. She was on my podcast talking about the finance side of travel, which is a whole nother, a whole nother topic, right? Like you said, finances can be very stressful for some people. This one trip this year could be everyone's savings pulled together to make this happen. I'm definitely not minimizing much privilege and resources it can take to travel, right? So the one thing that I can recommend, which will give you the number one piece of mind is travel insurance. So a lot of credit cards have travel rewards points that help you travel longer, travel better, travel for free. We just booked a trip to Costa Rica for next Friday. The whole flight was free, bar the taxes and fees, but we just used our points because we have a travel credit card. That same travel credit card has travel insurance included on it if you spend a certain amount with that same card and you can prove that it's for your trip. Travel credit cards sometimes have a lot of limitations. There's a lot of loopholes. Like they're definitely trying not to pay you, of course. However, I work very closely with a travel insurance company called FAY, F -A -Y -E. You can email me directly about getting a policy with them but they are totally disrupting the travel insurance industry with 24 seven telemedicine and app that's amazing that makes claims easy. I would say, I know it sounds like kind of old, but like travel insurance is the best way to help keep your peace of mind when things do go on plan that you can't control. As well as since COVID a lot of providers, tour operators Airbnb, hotels, flights, a lot of them have become very cognizant that the consumer is expecting flexibility. Of course we needed flexibility during COVID, but we've just kind of kept expecting it. Like now it's just like a standard. So before you book anything, just double check on cancellation, double check on refund policies, double check on reschedules. Like what is their term of limits for a reschedule date? Like just being very, like being okay with asking those nitty gritty questions, because if you know, Okay, they're gonna give me two years to rebook this or I might not get a refund, but JetBlue is gonna put that fee into my travel bank. So next time I book a trip, I can use it. Like you might be okay with that. And then that helps you feel more, more at peace too. And that just comes like, again, there's knowing that, okay, one of my anxieties is having to cancel and lose all my money, which I think is a lot of our anxiety around travel or stress around travel. Okay, what's my strategy for that? I'm gonna go through line by line everywhere we're going and just double check what those cancellation policies are like.

Kelly Berry (49:02) Mm -hmm. Yeah, I like the travel insurance. I think that's something like every time it comes up for me I'm like don't check that box like

Kelly Tolliday (49:19) Yeah, well, it depends on it depends on what provider like I always say no, when it kind of comes directly from the vendor or the supplier, but Faye, like I would, they are so good. And and yeah, it's something that you don't think is necessary. If you have a really comprehensive travel insurance policy through your credit card, maybe it's not that necessary. But for certain, especially if you're going on like a retreat or a group tour, a lot of credit cards won't actually cover that, whereas Faye just takes whatever you're saying that you need to cover for this trip, they'll cover it, as opposed to having to be specific to which line item of the trip that you're using your credit card for.

Kelly Berry (49:58)  Wow. That is disruptive and unusual. Yeah. Well, this has been a great conversation. Is there anything else that you like wanted to talk about we didn't get to or anything about what you do that you want to let people know?

Kelly Tolliday (50:02) Yes, yes. Yeah, I mean, I've had so much fun. So thank you so much for allowing the space for me to share this. It's my favorite thing to be able to give people the space and the opportunity to not just create memories that will last a lifetime, but also be able to kind of unlock a new level of growth for themselves and bring that back home. I think one thing that we didn't touch on is this integration piece. Like how do we actually put this back home? And what we say at R &R is integration is is intention plus action. So it's one thing where it's like, I intend to live more slowly at home. Okay, great. You're gonna get three days at home and then be wrapped up in your schedule and your Google calendar is gonna be filled up. It's like, okay, well, my intention is great. I wanna live slower. I wanna move slower. But what's the action behind that? What am I actually gonna do to make sure that I'm holding myself accountable? So I think… We can talk about cultivating a traveler's mindset and learning all these things, but then it comes down to the second part of this, which is the action piece and like getting clear on that. And that's something that I help with either with travel planning and advising. Like I can do custom one -on -one trips for, you know, regular, you know, honeymoons or just going away to Greece or whatever. I can do that. And I bring this level of intentionality to the one -on -one trips as well. If you want to come with a group, we have our group and retreats with a wellness focus in different locations around the world. Next year we're doing Peru and Greece. And then lastly, like I spoke about, I have a podcast called Transform with Travel and there's the ebook on my website, The Mindful Traveler that kind of touch on a lot of these strategies that we spoke about but goes into more in -depth practices and stuff like that.

Kelly Berry (51:56) Yeah, yeah, awesome. Yeah, we didn't, I didn't forget about the integration, but that's a great point. And I think, you know, when you, when you want to live a life where you're traveling and your travel is meaningful and intentional, I think naturally it just like lends itself to wanting to make part of those experiences part of your everyday, whether that's a slower pace or whether that's a different approach to your health and wellness or mindfulness or you know, even cuisine, know, whatever it is, but being intentional and then having a plan to make sure that that doesn't like go down the drain as soon as you walk in the front door.

Kelly Tolliday (52:38) Yeah, and the community piece is a big part of that. So of course, if you're solo traveling, like stay in touch with the people that you met in the hostel or met on the group tour. Staying in touch with those people that had those shared experiences with you helps you kind of remember those feelings that you had on the trip. If you're on a group retreat, we're really something we're really good at R &R is like keeping our WhatsApp groups alive and always throwing out journal prompts every week and sharing funny memes about the country that we were in, like keeping that connection to not only the people you are on that trip with, but the person that you became on that trip. Like that's the thread of that integration that helps as well.

Kelly Berry (53:16) Yeah, I love that. You were in the call when you're a thousand versions. You've been a thousand versions of yourself and you'll be a thousand more. Yeah, yeah, yeah. So who you were on that trip is one version. awesome. Well, thank you so much. will, for everyone listening, all of Kelly's information, links.

Kelly Tolliday (53:22) Yes. Yes, that's Suzette Bravo said that.

Kelly Berry (53:42) retreats, travel, all of that is in the show notes below. So please connect with her, reach out to her if you are looking at traveling, wanting to work with somebody who is intentional and can help you have the trip that you really want to have. And then of course, retreats, which is on my bucket list. I want to look into it. Yeah, yeah. Awesome. Well, thank you, Kelly. We appreciate it and we'll talk to you soon.

Kelly Tolliday (54:02) Yeah, we're going to make it happen. Thank you.

Kelly Berry's Bio photo

Kelly Berry is a strategic business leader and business coach. She is known for her operational excellence and her ability to drive growth and results across multiple industries.
She is also hosting her own podcast, Life Intended.