Freedom Looks Like This – solo travel for women over 40 ready to choose themselves
Freedom Looks Like This is a solo travel podcast for women over 40 who feel restless, disconnected, or tired of waiting for the "right time" to start living differently. Hosted by Damianne President, the show explores intentional solo travel as a way to rebuild self-trust, stop waiting for permission, and create a life that actually feels like yours again.
Solo travel is just where the story starts. What this show really explores is what happens when women stop waiting, take themselves seriously, and begin making decisions for themselves, without over-explaining or asking for approval.
Episodes dive into topics like:
- solo travel for women over 40
- fear, self-doubt, and the hesitation to go alone
- learning to trust yourself again
- identity shifts in midlife
- choosing what you want and acting on it
Whether you’re planning your first solo trip or simply craving more freedom in your everyday life, Freedom Looks Like This offers real conversations and relateable reframes to help you move forward, whether at home or on the road.
Freedom Looks Like This – solo travel for women over 40 ready to choose themselves
Your Adult Gap Year Doesn't Have to be a Year
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We keep telling ourselves we'll take the trip we actually want once we've finally figured everything out. What if you have that backwards? You will not think your way to your next chapter from inside the old one, and the clarity you keep waiting for tends to arrive out in the doing, on the trip itself. This is the adult gap year, reimagined, and it does not have to be a year, or a leap, or anything as big as you are picturing. After all, this is not Eat, Pray, Love.
In this episode:
- The season you didn't choose
- The trap of thinking harder
- The habit discontinuity effect
- A quiet month in Florence
- Interrupting one autopilot
This episode is for you if:
- you're in a season that ended before you were ready, a role, a relationship, the shape of your household, and you keep waiting for clarity before you do anything about it
- you've wanted a solo trip but told yourself you can't take the time, the job needs you, or you have to figure your whole life out first
- you've been calling this stretch a transition, or limbo, and some part of you is ready to do something with it instead of waiting it out
- you're a woman over 40 in a midlife transition who wants to feel like yourself again, not just keep showing up for everyone else
- you already travel solo, or you want to, and you're ready for the how, and you've heard enough of the why
About Freedom Looks Like This:
Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics.
Join the next Solo Trip Decision Workshop live on June 20. It's for women who've decided they want to take a solo trip and want help deciding the trip they actually want: https://freedomlookslikethis.com/training
Email: contact@freedomlookslikethis.com
Join Skool: https://freedomlookslikethis.com/community
In midlife, a lot of us find ourselves in a season we didn't quite choose. One thing has ended or it's in the process of ending, it could be a role, a marriage, the way your household looks as the children move out, your body. And we land in this transition. Maybe it's more accurate to call it a space in between seasons. Some days it looks like a reset. On the harder days, it can feel like limbo. And the whole time, we keep telling ourselves we'll take the trip we actually want once we've figured it all out. So here is the question I want to explore with you today. What if we have that backwards? If that's the season you're in or the transition space you're finding yourself in, 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 Damianne and this is Freedom Looks Like This. Let's get started. Okay, so we start in between seasons. What do you call that place? I hear different women call it different things. As I already mentioned, some call it transition, others call it uncertainty. Maybe you experience it as not feeling like yourself. But life goes on. You're still responsible, there are still things you've got to do every day. You show up for the people who count on you. Some of you are putting your children or your family first, not even realizing how much you need for yourself right now. So when we talk about taking a trip, thinking about time away, you think that it's something for later, after you get clarity. And that could sound like, once I've figured it out, then I'll go. But what I want to share with you is that a solo trip is a pattern interrupt. Keep that phrase in your pocket because there is a reason it works, and I'll come back to it a little later. What's actually missing isn't more thinking. That's what a lot of us tend towards. We think that we're going to think ourselves out of whatever is going on in our lives. But what's missing is the chance to tune into yourself, and that's what a solo trip gives you. It's a connection to yourself that allows the answer to arrive. And yes, there has to be desire because without it, the path can feel like being lost or estranged from your life. But if you're listening to this, then I think you already have the desire. The thing to know is that you will not think your way to the next chapter from inside the old one. The clarity you keep waiting for is not going to arrive that way. And travel isn't the reward you get once you've figured out your life. Travel is actually a way to figure it out. And I do not mean it pray love fashion. But if the desire is already there, what is it that stops us? For a lot of you, I can already hear it. Maybe you're thinking, I can't take a gap here. I have to admit it's a bit of clickbait calling this episode a gap year. But I think that when you hear that, something is going to come up for you. Maybe you're thinking, I can't just leave. The job won't be fine without me. I'm needed here. Who else will do this work? Who else will do all of the things that I'm responsible for? I'll put you at ease right off the bat. You don't need to take a gap, yeah. You just need to make some space. And when women tell me the job won't be fine without them, and I hear this a lot, what I want to say is if the job hinges on you always being there, then the job is broken. There is a lack of resilience in there. It's too much on you, and it's not sustainable for the work. So it becomes extra important for you to take that breakaway. Especially if you're feeling unhappy at work. Especially if you're feeling like there is too much stuff being asked of you. Maybe what you actually need is some distance from your job, a chance to reconnect with yourself, to find that pleasure and that joy that is available to you, not just from work, not just from checking things off and accomplishment, but in being however it is that you want to be, in actually getting in touch with yourself. Now, this often brings up a problem of perfectionism. I studied math, and I can remember lots of evenings and nights at the kitchen table doing my homework and facing a hard problem that I couldn't solve. What I did then, what we tend to do with problems like this in math, is we break it down into a much simpler version of the problem. We find a smaller example that we can solve, and then we make it bigger and bigger and bigger until we get to the original problem that we wanted to solve. I'm a math geek, I can own it. So that's the example I came up with. But really, it's the same thing here. The question isn't whether you can take a year. The question is how can you make space in the life you have right now for the thing that you want, for the trip that you've been dreaming of? That's a real question. How do you make that space? And I think it begins with noticing the trap most of us fall into. We think that the solution to everything is to think harder, to do more, to do harder. Well, how well is that working for you? I know that it doesn't work that well for me. And I learned that lesson over and over again. If what we want is change and it's been hard so far, then what we need is a pattern interrupt. We need to do something different. And what's missing is not thinking, but actually living your way into that something different, experiencing something different, paying attention in the moment, trying new things out. You don't even know yet what's available to you. You don't even remember all of the things that brought you delight when you were younger, before you became this version of you, before you became what you are to so many different people and estranged from yourself. There's nothing wrong with doing the right thing. We were conditioned that way and we have a habit of it, but it also allows us to get disconnected from ourselves. And so the goal with solo travel is to put yourself in an environment where you have the chance to rediscover who you are and what you like, what is it that you want. So I'll give you an example of how this works in real life. I lived in Carp, Ontario with my family when I was in high school and university. And at some point we moved a few blocks. Now we moved in the same vicinity but to a new subdivision, maybe about less than a five-minute drive away. And I cannot tell you how many times I was driving home on autopilot and past the new place going to the old address. This is what happens in our regular life. The things that we're used to are easy and we don't even need to think about them. So they have a way of taking over even when we intend to do something else. And this happens in all areas of our lives. We have all of these triggers, all of these prompts for the things that we have a habit of doing. And so what happens with solo travel is that you take yourself out of the environment where all of these triggers live. And when you're not reverting to old conditioning, because you can't just be an automatic, then you have a real chance to find out. Who is this new person? This new me? Who is the person that I'm becoming? Who's the person that I enjoy being? And so that's what I want you to think about. This is the thing I told you to keep in your pocket because there is actually a name for what's happening. Researchers call it the habit discontinuity effect. So much of what we do runs on autopilot. Think about it right now. What are the things that you do and you don't even have to think about them? In the same kitchen, you probably move around in the same way. You don't have to think about where to reach for a cup or a glass or the rice. Your drive to work, the faces you see, all of these are setting off the same patterns. They make it really easy for us to make the same choices day after day. So when you change your environment even a little or even for a little while, these cues begin to loosen the grip on you. And you have a sliver, a little bit of space where you get to choose again. All of a sudden, that old program can't run because it doesn't have all of the things it's looking for. And so you get to start to notice, hey, what are my choices here? What am I actually going to choose? That is the real gift of a solo trip. And here's the part I love. I want you to go on that solo trip if you've been thinking about it. I want you to experience that delight. But only if you want it. And on the way, whatever your circumstances are right now, you don't actually need a plane ticket to start having this experience. I'm going to give you an invitation, a way for you to start this week before we're done this episode. So keep listening. I have given myself lots of these slivers before, these windows. In 2022, I spent a month in Florence. It was when the world was just opening up again and after everything had been closed for so long. Remember how that period felt? My sister lived in Florence at the time, so I had been there before. But every other time, the city was packed. If you've seen photos of Florence, or if you've been to Florence, you know that it can get very crowded. I remember seeing the line wrapping around the cathedral and thinking, there is no way I'm getting on that line. But then going at a time when it was quiet, it felt like I had the city all to myself. I have so many great memories from this trip, and it was such a pattern interrupt for me. One of my favourite cafes was close to the river. It was run by an Australian woman, and they had the best cinnamon buns. And then there was also Fourno Vecchio, which has well, I don't know, I haven't been back in a few years, but it had this excellent fig cake. And I got to try chickpea pizza for the first time. So every morning I'd go for a walk. Sometimes I'd stop for a coffee, sometimes I would just walk, sometimes I'd stop for some cake or go to the bakery. And I remember walking on the street and seeing the dome of the cathedral in the distance against a perfectly blue sky and just being so grateful, so thankful that I was in Florence, that I had this opportunity in my life to really be present. I walked wherever my feet took me. And often it was just 15 to 20 minutes, several times a day from the apartment I was renting. And this was a chance to just discover little nooks and crannies, tuning into a new place. And here's what I noticed. When you're home walking a street that's familiar, it's so easy to tune out. Because you expect you already know everything there is to discover. A new place doesn't let you do that. And then there was the cathedral, the duomo. It's a place that I never saw empty before. And one morning it was completely empty. Imagine just standing in that space, that enormous space, quiet, getting in touch with gratitude. I felt like one of the most lucky people. I just let myself be peaceful. I said a prayer of gratitude and a prayer for my grandmother and other ancestors. I usually light a candle, but I don't like the fake ones. I can't remember what was in this cathedral. But what I understood in that moment, and it's something I come back to, is that I can find opportunities even within constraints. I have to work, most of us do. But I can choose where to work. I can choose to be in Florence when Florence is quiet. I have flexibility when I take holidays in a way that I never did as a teacher. When I was a teacher, I had long holidays. Whatever your circumstances, there is something that you can find, some space that you can find. You can create a window for yourself. We get so caught up looking at what we don't have, at what's not possible, that sometimes we miss the opportunities that are right there for us to take. And those are opportunities that could really enrich our lives, that could really help us figure out and create a meaningful life, whatever that is to you. So my advice, my invitation is not for you to go to Florence. It's that the trip doesn't wait for your life to make sense. You have to look for the gap, find the gap. When I went to Florence, I didn't have to quit anything to do it. Being in Japan and booking a tour in Harie was a very similar thing where I was just creating this liver of space where I could go and have an experience that intrigued me. I really enjoy exploring the cultures of different places when I travel. And so Harie for me was about exploring this water culture. And I was supposed to book a month ahead and just thought about it and managed to book the day before. Don't cancel yourself. Don't be the one to tell yourself no. It's really not necessary for us to overthink many of the things that we tend to overthink. We spend a lot of time planning without even knowing what's possible, without even knowing the breadth of opportunity. I mean, there are more opportunities than you even think is possible. And you can only know that by putting yourself in a new space, by trying different things. So whether you're taking a one-day trip, going away for a few hours, or going on a sabbatical, my invitation for you is the same. It is for you to pay attention. It is for you to notice what are the things that really delight you and what are the things that you want more of. The difference is in how much of that you get, and it depends on the time you have, it depends on the circumstances. But regardless, you can always get some of it. I talked last episode about thinking of some of my activities and trips like different parts of a meal. Sometimes I just want a bite, sometimes I want an appetizer, sometimes it's a full course or a nine-course meal. All of these are satisfying in different situations to me. The size doesn't change whether or not you can get the thing that you want from the trip. So as you start exploring with those different types of trips, those different types of activities, notice what shifts for you. In the back of our heads, we often have this question: can I handle this? Can I handle a life I didn't plan for? And that question can only be answered by going. But once you've gone, even for a few hours, the question changes. It stops being, can I handle this? And it becomes, what's my next move? It's such an important shift. That's what a trip gives you. That waiting never will. You get a chance to come back to yourself and to start choosing the life you actually want. So here is your invitation for this week. It's small because I believe that even small action creates momentum. One small action gives you the chance for another small action and on and on we build. So this week, interrupt one autopilot. I'm sure you can come up with many of them, but just pick one. Maybe it's the route you drive without thinking, the seat you always take, that's me. The coffee you always order, the scroll you fall into on your phone without even deciding to, and then you realize hours have gone by. Catch just one of them and change it on purpose. Take another route. Sit on the other side of the room. Order the thing you never order. It sounds almost too small to matter, but that's the point. Catching yourself, changing something, these are all little pattern interrupts. Notice what happens. I expect that you're going to start feeling more awake in your own day. And that is where confidence really starts. Not from thinking about it, from doing one small thing, and letting that make the next one feel possible. So as you do this invitation, I want you to give yourself a chance to feel curious. Give yourself a chance to notice your energy. And if fear comes up, that's okay. Remember, fear doesn't mean stop, but it means pay attention. There's something here, there's information. And if you feel uncertain, of course you do. It's normal to feel uncertain when we're doing something new. Maybe you've never done some of the things you're trying out, or you haven't done them in a while. So uncertainty is completely normal. But stay with the curiosity. Curiosity is a doorway into new ways of seeing, new ways of being, the opportunity to explore. So that's your invitation this week to interrupt one autopilot and notice what comes up for you. Hey, if you want to level up, do this multiple times over the next week and take note of what comes up each time and what changes. Now, if you want some company for the bigger step, the step of going on the solo trip, I have a workshop coming up. It will help you take the decision out of your head and into the world. Whatever sentence it is that you have about your dream trip, about the trip that you want to take, bring it with you on June 20th to the solo trip decision workshop. It's a one-hour workshop. You come with a sentence and you live with one decision. This is the way we get out of overthinking. Thanks for spending this time with me. Whatever you choose this week, a month in a quiet city, just a different turn on the drive home. Both of these, either of these is an indicator that you're already doing the work. You're remembering that you get to choose.