Freedom Looks Like This – solo travel for women over 40 ready to choose themselves

I'm sharing a conversation from Kellie Stirling's podcast Talkin About Midlife where I'm visiting as a guest rather than a solo host or interviewer. We started from the very beginning: Saint Lucia at birth, Canada at 12, then India for my first teaching job, then Sudan, Japan, and finally Prague, where I've been for thirteen years. Somewhere in all of that, a Sufi teacher in India said something to me in my mid-twenties that's still relevant to me and an important reminder more than twe...

Maybe you've been thinking about a trip for months, looking at flights, reading about the destination, knowing roughly what's there. And still not booking. Or you've already been on the trip and running a calculation the whole time: how do I make this count? Was this worth it? Both versions have the same problem. The question you're asking doesn't close. It just generates more conditions. In this episode, Damianne introduces the two-word question she's used for years, one that doesn't require...

Each of us has a default response to unexpected moments, often without noticing it. I watched mine during a recent trip in Japan, paying attention to where I used to smile and keep moving versus where I'm now stopping, staying in the conversation, and letting things land. A place moves forward without you while you're away, and so do you. You don't just come home with experiences. You come home as someone who made a series of decisions, and that's what persists. This episode is set in Japan, ...

I can feel right away when something is slightly off and I have to decide, quickly, what I’m going to do with it. Do I say something. Or do I let it go. I think you know that moment, the one where you’re still in it, and you’re already deciding what it means, whether it’s worth your energy. Sometimes you don’t say anything. But later, you’re still thinking about it. This episode starts with something that happened at a hotel spa in Sapa. But it’s not really about the spa. It’s about that mome...

People think meaningful travel comes from big moments, the kind you plan for, experience, and remember as highlights. But some of the days that stay with you the longest don’t look like much at all. In this episode, I share a day trip to Awaji Island with a friend and her family, a day that wasn’t supposed to be particularly exciting. It included small stops, simple meals, and moments that didn’t seem significant on their own. And yet, by the end of it, the day felt full in a way that...

When you travel alone, it’s easy to fall into the habit of accomplishment: the pressure to see more and make the most of every moment. But what if the real question isn’t where you should go next? In this episode of Freedom Looks Like This, Damianne shares a moment from Japan that changed the way she thinks about pace, presence, and what it means to truly inhabit a place. After moving quickly through several countries, she arrives in Wakayama, a destination she first dreamed about more than 1...

Can competence make you invisible? If you’re a capable woman over 40, the one who organizes, anticipates, manages everything, you already know how to move through the world efficiently. You know how to make things work. But what if the very skill that makes you strong is also the thing that keeps you partially unseen? As I traveled through Sri Lanka, Cambodia, and Laos this past month, I noticed something unexpected. In unfamiliar places, where no one knew my history or reputation, I still de...

I went to Sri Lanka expecting to work a little. To stay alert. To dust off old instincts. I assumed it would feel familiar in the way India once did, manageable, but intense. Instead, it felt easy. That surprised me. In this episode, I’m reflecting on what happens when a place is gentler than you prepared for and the hard parts you braced for never quite appear. I talk about arriving ready for effort and finding myself able to relax sooner than expected. Ease didn’t mean everything was ...

At some point after forty, many women start noticing something subtle but persistent. We're engaged and competent, but yet, in small everyday moments, we're not being seen in the same way. This realization doesn’t usually arrive as one dramatic incident. It shows up in quieter ways — in lines, in shops, in airports, in conversations — moments where you realize you’re expected to wait without explanation. When women talk about this, we often use the word invisible, even if we can’t quite point...

What do you expect from your first solo trip, especially as a woman over 40? A lot of us carry the idea that if we plan carefully enough, choose the right destination, and do everything “properly,” the trip should go smoothly. It should feel relaxing and signficant! And when things go wrong, even in small ways, it can feel surprisingly upsetting. In this episode, I talk about why that expectation shows up so strongly for women traveling alone later in life, and what actually happe...

Do you remember the first time you considered going into a restaurant by yourself, and hesitated at the door? For many women, the discomfort around eating alone isn’t really about food. It’s about visibility. About being seen. About the quiet rules we’ve absorbed around when it’s acceptable to take up space. In this episode, Damianne reflects on a moment from her twenties that still lingers, how solo dining has followed her across decades and countries, and why certain restaurants...

Many women think solo travel is something you do in your twenties, before life gets busy and complicated. In this episode, I explore a very different truth. Midlife brings a kind of clarity, self-knowing, and freedom that can make this stage of life an ideal moment to travel on your own, whether for the first time or as a rediscovery. We talk about the quiet shifts that happen as you get older, the easing of expectations, and the surprising ways your priorities change. I also share how ...

What if becoming a woman who travels has nothing to do with plane tickets, planning, or confidence … and everything to do with something far quieter? In this episode, we explore the subtle, almost invisible shift that happens long before your first solo trip, the one that most women don’t recognize until they’re already in it. It’s the kind of shift that shows up in tiny private moments, in questions you didn’t know you were allowed to ask, and in a version of you that’s been waiting pa...