Follow the Feeling, Not the Feed: Choosing Solo Travel Destinations After 40

A lot of us have a list somewhere, in a notes app or just in the back of our heads, of places we'd like to visit. Every place on it sounds lovely, and not one of them is an obvious yes. So we keep researching, and we keep not choosing.

What if the way you've been choosing where to go is the very thing keeping you home? The best destination for you probably isn't the one the lists keep pushing, and it isn't the safest or the most impressive one either. There's a different question to ask first, and most of us have never been taught to ask it.

This episode gets into why researching more makes the choice harder instead of easier, the reason a place that looks perfect online can leave you feeling almost nothing once you're standing in it, and four feelings I've chosen trips around, along with the very different places that gave them to me. The places are mine. The question underneath them might change how you pick your next one.

In this episode:

• The 15 best places trap
• Situation selection, explained
• Four feelings
• Your invitation

This episode is for you if:

• you've saved a dozen versions of "the 10 best places for solo women over 40" and still can't commit to one
• you travel solo, or want to, and every option feels reasonable but none of them feels like yours
• you're a woman over 40 who has gotten so good at the sensible choice that the muscle for choosing what you actually want has gone quiet
• you once did the bucket-list trip and felt almost nothing, and you've never quite known why

Resources mentioned:

Take the solo trip personality quiz at freedomlookslikethis.com/solo-trip-fit/.

Transcript

SPEAKER_00 0:00

Many of us have lists everywhere. You could have a list in notes somewhere on an app or on paper or just in the back of your head of all of the places that you might go someday. All of the places that sound interesting or that look interesting for you. And it's very likely that every place on your list sounds just lovely, but none of them is an obvious yes to you yet. So we keep researching and we keep not choosing. I've been thinking lately about why that happens. And I don't really think it's the list that's the problem. Really, it's about the order in which we're doing things. So in this episode, I want to pose a question to you to help you think a little bit differently about this. What if the way you've been choosing where to go is the very thing that is keeping you from going? If that's you where you have a list, but you're still not taking the trip, then this episode is for you. Most women think solo travel is about being brave or fearless. But it's really about letting go of the expectations holding you in place. This show is about what changes when you stop waiting and take yourself seriously, starting with intentional travel. I'm Damian and this is Freedom Looks Like This. Let's get started. Maybe it's just me, but I think many people are so used to doing this. We save things for later. Maybe you still bookmark. Or you might have articles or photos that you saved. How many versions of the 15 best places for solo women over 40 do we really need to read or keep? And then maybe there's a country that a friend went to and they just couldn't stop talking about. But the strange thing is that the more we add to the list, the harder it is to actually go on the trip. Everything on there seems fine, it's reasonable, but nothing is actually pulling you by the hand and saying, let's go, let's do this. So why is that? I think it's because we're sorting by the wrong things. We sort by which place is safest, which place is most impressive, which place we see the most on social media with the most things to do. And these are all fine things to consider, but they're not the first thing. They're not the thing that actually gets you to take the trip. So when you start there, you end up with a list of good answers, but then you still don't go on the trip. And the worst thing is that the research didn't fix the problem. In fact, the more you read and the longer the list got, then the harder it was for you to actually choose. And then maybe you think, oh, I'm just gonna figure it out later when I have more time to really look into it. I've watched so many women do this and I've done it myself. We treat the indecision as a sign that we haven't found enough information. When really it's a sign that we've been asking the wrong question or looking for the wrong signals. So, what I actually believe is that the best destination for you is not the safest one or the most popular one. It is the one that matches the feeling that you want to have on the trip. The feeling that you're actually craving right now. What's the version of yourself you want to practice being on this trip? So you pick the feeling first, and then you pick the place, not the other way around. Because really, I don't think the problem is that you don't know what you want. If you're a woman over 40, you usually know what you want by now. You know what you want to do and what you don't want to do on a trip, at least in principle. The problem is that you've gotten so good at choosing what's sensible or what other people would approve of, that the muscle for choosing what you actually want is quiet. Too soft for you to hear. So you look at that list over and over again, and you can pick which places are the right ones, but you can't commit to which one you actually want. I didn't always travel this way, by the way. I didn't always travel for feeling. For a long stretch of my life, I was the person who was just thinking about the next place to go to add it to my list. I was just counting countries. That was the goal. And because I was counting countries, I didn't want to go back to a place I'd already visited. Because what was the point that would not actually help me accomplish my goal? There were just too many places left to see in the world for me to go back. Okay, let me be honest. I still want to visit every country in the world, more or less. I've been to 76 of them, and so that's a little bit less than half. But the thing is that what I choose for when I'm thinking of the next place to go is different than before. These days, I choose for beauty. I choose for ease. I think about the feeling that I want to have at the end of the trip. And the troops have gotten better. And it's not because the places have gotten better, but it's because I am more myself. I am finally able to ask the right questions when I'm on the trip to have the experience that I want. The most obvious example of this is that I've been back to Japan twice in the last year. And I want to go again. In fact, I would like to go every year. And when I lived in Japan, when I left Japan, I thought that I might go back to visit friends, but I never expected that it would be a place where I wanted to keep going back. So I wonder, do you have any idea of the feeling that you want to experience on your next solo trip? What comes up for you when I ask that question? Hold that thought. Because I'm gonna go into the science a little bit or into the research at least. And there are two ideas from psychology that completely changed how I think about choosing a destination. The first one is called situation selection. It comes out of research on how people manage their own emotions. Of all of the ways you can choose how to film, the most powerful one that does the most work is choosing which situations you put yourself in. It doesn't help if you're just gritting your teeth the whole time you're in a place or in a situation, or if you're just talking yourself into a better mood after the fact. If you've done any coaching with me, you know that I also think that thoughts are really important. But the situation you put yourself in, the triggers, really help with you being able to think different thoughts. So choosing the room before you walk into it is one of the most important things you can do. Choosing the show you watch, choosing the music you listen to, all of those different situations really affect the way you feel. Many of you, when I say that, you can immediately relate, right? Because maybe you put on a certain type of music or you watch a certain type of show when you want to feel something specific. So if you think about it, a trip is just a very big, very deliberate situation that you get to select on purpose. The second idea I want to share is called effective forecasting. And that's a slightly clinical way of saying that we're surprisingly bad at predicting what will actually make us feel good. Is that crazy? There are two researchers who name this, Daniel Gilbert and Timothy Wilson. And they found that we tend to lock ourselves into one obvious feature of a future experience and let it crowd out everything else. So when we look at a destination, we fixate on the one loudest thing, the one thing that we see or that we hear everywhere. Is it safe? Is it depressive? Will it photograph well? And we forget to ask what the actual days will feel like when we're inside of it. That's why you can have something on your bucket list and then you do it and you feel really nothing. And at the same time, you could be in a place that is really unglamorous and it can bring up all these feelings for you that undo you in the very best way. And to be honest, one of the things that has made this worse is you guessed it, social media. Because now the loud feature isn't just in our heads, it's right there in front of us as we scroll every day. We see one perfect photo of a place. Okay, maybe a few perfect photos if it's a carousel. And all of these are really the most photogenic corners of that place. And from those photos, we forecast the whole trip, everything about a place. We're not even predicting our own feeling in that time. We're borrowing somebody else's highlight. And then we wonder why is it that the troop doesn't feel like what I expected? Part of it is because of that feed. And remember, often there are filters that can be applied to images too. So this is even worse because sometimes it's setting up an unrealistic expectation of what we're going to see. But choosing the feeling that you want is how you climb back out of this pit. Because a feeling is yours in a way that a picture isn't. So let's put those two bits of research together. To reiterate, the most powerful thing you can do for the way you want to feel is choose the situation that is going to bring up that feeling for you. And the reason most of us choose the wrong place is because we're predicting from the loudest photo that we saw, the loudest feature we're aware of instead of the real one. When you pick the feeling first, that's a way of correcting for this. It puts the real question back in front of the decision. Think about all of the places you already do this in your life. If you wanted a calm experience, you wouldn't go to the loudest restaurant in town or the place that is a buzz just because it has the best reviews. You would choose the quiet place that you're familiar with where you know you're going to have the experience or the feeling that you want. We do this without thinking when the sticks are small, but then we somehow forget to do it in bigger, more expensive, more loaded decisions. For example, where am I gonna spend a week of my life this summer? So the trip is really the same move. You decide the feeling, and then you let the feeling choose which room you're going to be in, which situation you're going to be in. I had an experience of this recently. I was in Hanoi and I was seeing all of these photos of Train Street and people were talking about it. And I sat there drinking an overpriced drink, surrounded by all of these talk groups looking for the same excitement. People were jogging for position, and I was getting a bit annoyed actually because I thought, okay, I was here first, and all of these people are coming and they are going to make it hard for me to see. So finally the train came and everyone has their camera out and is trying to take a photo, and I managed to take a photo, but not a video. And really, the train was short. It happened so quickly, it really wasn't that impressive. Somehow I had built up this experience into something that was going to be beautiful and exciting, and it just fell flat. And the reason I thought that it was going to be beautiful and exciting was because I just counted on all of those photos that I saw on social media. They were all the perfect photo, which is almost impossible for a person to get. So I really expected it to look impressive, and that really was not what I got. So let me give you four of my feelings with the place attached to each of them. I think it's easier for you to understand with an example. I want to start with the feeling that is most alive in me always, the one that I actually have a principle around. Awe. Because for me, travel is really one of the ways that I access awe. And it's one of the things that travel is for. Travel is awesome in the original sense of the word. And it also fills you with awe. That happens in beauty, in nature, and sometimes in conversation. I don't want to say that this only happens when you travel. It does happen at home too. But I think I'm more attuned to it when I'm away because I have more room for it. It's not crowded out by all of the stuff of everyday life. So when all of that crowded stuff with the ordinary noise gets toned down, then there's more space for beauty. The beauty gets louder to me. So the place I'm thinking of is Quangxi, which is in Laos. I don't know if I'm saying that right, but that's how it looks to me, Quangxi. And it's these waterfalls, these pools one above the other. And this color of water that was just so clear and blue and beautiful. I remember thinking, is this all natural? I don't actually know, but this is amazing. There wasn't just one good view where everyone crowds around for the photo. I've been to a lot of those waterfalls too. But here, everywhere, I took a forest path where I was all by myself with just glimpses of water along the way. I took the usual path where there were lots of people, and it was all beautiful. And there are pools for you to swim in, but that wasn't part of my plan. It looked lovely. But for me, the experience there was about seeing, not about being in the water. I just sat and looked around me for some time. And I thought, oh, I could spend more time here. The feeling for me, that feeling of awe, a lot of the time I get it through my eyes. I can think about so many different waterfalls where people are like, oh, aren't you going to go in as if somehow by me not going in, I'm not enjoying the experience. And yes, I'm from the Caribbean, but I don't have to go in the water for me to enjoy the experience. For me, it just adds a bit more complexity. So for you, it's really important for you to know how the feeling arrives for you. What are all of the different ways where you can experience the feeling that you want? Does it come through your eyes or your skin or your taste, through your stomach, through conversation? That's its own kind of self-knowledge. And it's very important because it also changes how you choose. So if the feeling you're hungry for is beauty, if you want to be knocked sideways by seeing something, by seeing how lovely the world is, then you can choose for that. You don't need it to be the safest country on the list or the one with the best nightlife. You need scenery that doesn't let up. That doesn't have to be expensive. Have you had a moment like that somewhere where the beauty was almost too much? I think earliest memory was Olympic National Park, actually. As I just said this, it came to me. Oh, I was in high school then and I went to camp. And I remember being in this park and just there being moss and nature. And I don't think I have any photos of it, but that feeling, that feeling of being in the immenseness of the world where there is such beauty, that's a feeling that has been important to me for a long time. Is there something like that that comes up for you? That's really important because that's data that helps you figure out what is it that you want to feel. And from that, where is it that you want to go? The next feeling is ease. Now I know ease can sound like a small thing to build a whole trip around. But I promise you it's not, especially if your real life is very busy and ask a lot of you. And maybe you're tired in a way that sleep doesn't fix. In that case, ease is so important. And the place I think about for east, my most recent place is Japan. Now, that might be a surprise to you because I don't speak Japanese. And maybe you're thinking about Japan, but you don't speak Japanese. But I spent a month in Japan recently, and for me, there was such a strong sense of ease. It's not about temples or about famous views, but just as simple as taking a local bus to visit Nachikatsu, right, which is in Wakayama. I don't speak Japanese and it didn't matter because everything was built in a way that was clearly communicated. The times were clear with signs. The stops were very clear because I was given an English handout at the beginning of the trip. It was so easy to get around and I never felt stressed, even though I was taking the bus from place to place with many stops over the course of a whole day. For me, that's amazing in a place where I really can't read and I can't really speak and I don't really understand. There were just two of us on the bus for most of the trip, a Japanese woman and me. And at some point when we stopped for lunch, we had a small conversation with each other using Google Translate. And I discovered that she was very surprised I didn't speak Japanese. Maybe because that bus store tends to attract to Japanese people. At some point, more people got on the bus, but then they left before we got back to the main station. So the two of us were really the only ones on that trip the whole way. And the whole time on that bus store, the scenery was just beautiful. We were going from sides to sides to capture different photographs. There was this clear water, snow-capped mountains, little countryside houses, temples, Japanese architecture. I felt completely taken care of in a place where I don't speak the language. So, yes, the idea of beauty comes in here too. But the bigger one is ease. Just being able to let somebody else take care of all of the details for me that day. Ease is a completely legitimate thing to choose a trip for. If what your life needs right now is a place where the train runs on time and you don't have to fight for anything, and the whole environment does the work of supporting you, then choose for that. You don't have to do a hard trip to earn your way to an easy trip. If the easy trip is what you need, take the easy trip. There was a time in my life when I fent that the trip had to be complicated or hard for it to be worth it for me to actually take it. My best example of that is the Philippines, where I've talked about on a different episode. I used to think that if the trip was too smooth, then I hadn't done enough. I want to offer you that that is not true. It's taken me a while to learn that. But there is no price for choosing the harder country. As a woman over 40, if you spend the last however many years being the one who handles everything, who absorbs the friction so other people don't have to, then a place that handles things for you might just be what you need. What comes up for me is the movie Waiting to Exhale, not because of what happens in the movie, but really I think a lot of us are kind of holding our breath to a large extent. And really, if you can find a place where you can just be yourself for a while, where you can breathe deeply, where you can sleep at night, where you can just relax and know that everything is taken care of. And if that helps restore you, if that helps you reconnect with yourself, then you tell me how much is that worth to you. Now the third feeling is aliveness. It's the opposite of being numb. It's that feeling where all of your senses are going and you're completely awake to being exactly who you are, exactly where you are. And for me, that was in Hanoi. When I was waiting for that train on Train Street, I was feeling very alive. The train track runs right between the buildings, and people sit on the track and take photos and wait for the train to come. But as I said before, when the train finally came, it was over so fast. It was over so fast that I felt let down. And so I felt that little tug to stay, to wait for the next train so that I could get the right perfect shot. Have you ever done something like that where you try to replay the moment because you didn't capture it the first time? But in the end, I didn't. I reminded myself that I don't travel for the photo. And it mattered more to me to honor the fact that I was really tired. I had walked a lot that day and my feet hurt, and what I wanted was to go back to the hotel and put my feet up. That right there is the life that's actually for me. It's not about the dramatic moment, but it's about being awake enough, in tune enough with yourself to do what it is that you need in the moment to be able to choose in real time. Hanoi keeps you awake all the time, honestly. You have to be switched on just to cross the street, reading the motorbikes, finding the gap, moving through the traffic. The whole city asks you to be present. And that's really the gift of it. So if the feeling you're missing is aliveness, if your days have gone a bit gray and you want to feel switched back on, then choose a place that makes you wake up, a place that makes you feel alive. Somewhere where your senses can't go to sleep. Now the last feeling is warmth. And I mean human warmth, being or feeling folded into community. It's the feeling that you're not just Out there alone. This is restorative in a different way. And the place that gave me this was Albania. I got invited for dinner with a Persian family who are Baha'is like I am. And they had also invited an Albanian family for dinner. This family was so excited to tell me about their country. They were so eager to share it, to make sure I understood it, and to give me tips that are only possible from someone who really loves the place that they're in, who really loves their home. And it was also an emotional evening because the family was three people, the mom and two children, and that's because the father had passed away. So there was also grief in the room because the passing was quite recent. And these things lived side by side, the grief and the generosity. And there's one small detail that I've never forgotten, and it's that there was so much food and enormous bread. Everything was delicious, but there was no bread on the table. And apparently, bread is a staple in Albanian culture. And at least for that family, it's central to the way that they eat. So somebody had to go off and buy some bread. Because a table without bread was unthinkable, even if it had so many other things on it. So I think about that small act all the time. Someone leaving a full table to go and get the one thing that was missing so that a guest would be properly looked after. To me, that's warmth. And I think it's something that a lot of women are afraid that we won't find if we travel alone. The fear is really that you'll be lonely. And I want you to know that that warmth is something you can choose. Some places, some cultures, some tables will fold you in in a way where you do feel belonging in a way that is warm. I also have this memory of the first time that I went to Amsterdam. And I was just sitting at a restaurant by myself, and there was a table beside me. And the people there, we made eye contact, we smiled a few times, and then they struck up a conversation with me. And it was nice just, you know, to get to talk to some local people. In fact, that's always something that I'm interested in, talking to locals as I travel. And sometimes the best way that I can do that is by finding a local guide. But you can really get to experience the warmth of a culture if that's something that interests you. So if that's the pull for you, choose towards the warmth. Go somewhere where people will pull up a chair, where people are interested in talking to others. So these are four of the feelings that I've chosen for. Beauty in Laos is in Japan, aliveness in Hanoi, warmth in Albania. It doesn't mean that each place only has one feeling. A lot of those feelings do tend to layer. And I'm not telling you to go to these four places, although, of course, you're welcome to choose any of those if it's rotten over you. But what I want you to hear is that this method is something that you can use. You can look for the feeling that you want to have and choose a place based on it. Those four places are mine, but you can apply the method in any way that you want. Because if you go back to that list, the one that you've been holding maybe in your notes app or in the back of your head, I think you'll find that the problem isn't the places. The problem is what you're actually choosing for. Maybe you were starting from where, but the question is actually, what do you want to feel? So start there and maybe the list will reorganize itself. Maybe automatically some of the options you had on the list will fall away because they were there because they looked impressive, or they were there because they were right for somebody else, but they're not right for you. And maybe something will stand out. A place will stand out because of the feeling that it brings up for you, or that you know you will find there. You know whether you're starving for beauty or ease or warmth, or to feel awake again, or something else. Don't let it be outvoted by the safety rankings and the top 10 lists. Let the feeling win. What's the place that you keep not choosing because it doesn't look like the smart pick or the most impressive pick or the one that would make sense to explain to someone else? Pay attention to that. That's the feeling. So here's my invitation for you this week. Name that one feeling that you would like most from your next trip right now. Just one feeling. Choose one of mine, ease beauty, warmth, aliveness, or find your own. Then match it to one single place. Maybe it's a place you've been before, or maybe it's somewhere new. One place that you believe would give you that feeling. And if you're ready to level up, pull out your calendar and just block out a three-day window in which you're going to explore that place. You're going to research it. It'll just be three days where that's the only destination you're allowed to look into, where you can immerse yourself in that place and see whether or not it really matches the feeling you thought of. That's it. You're not booking anything else yet. It's not a big commitment. You're just letting the feeling pick and you're scheduling time to look into it on your calendar. See what happens when you stop researching a whole bunch of different places and you let yourself just want one thing. And if you're not really sure about the feeling and you want something to help you come up with that, I do have a solo fit trip that can help. The link will be in the show notes. Thanks for spending this time with me. If something in the episode resonated, choose one small option and try it in whatever way feels doable for you. I've given you a few options. And if you want the simplest way to start, go take my solo trip fit quiz and see what stands out from your interest right now and what feeling might be the right one for your next solo trip.