A Sufi teacher in India looked at me in my mid-twenties and told me I was on a train watching my life pass by, just watching it, from the window while not making decisions nor getting off.
I had moved to India because I needed a job, not because I was searching for something. I finished university in Canada with a teaching degree and there were no jobs in Ontario, so I found one at an international school. That’s how it started. And then I found myself in a country so confronting, so different from anything I’d known, that I had to learn how to feel okay in my body in a way I’d never needed to before. After India, I felt like I could live anywhere.
I’m sharing this conversation because it goes somewhere my own episodes don’t usually go: all the way back to before I could even imagine the life I have.
Kellie Stirling of Talking About Midlife interviewed me, and we started from the very beginning. This story is the full long version, including the years it actually took.
In this episode:
- Saint Lucia to Prague
- The Sufi teacher’s reading
- Training the nervous system abroad
- Searching vs. meeting yourself
- Midlife, identity, and new roles
- Fermented rice sand
- The woman in Laos still looking
- 20% more enjoyment
“Meeting yourself is different than searching for yourself. When you meet yourself, it’s like: I already know I’m here. I’m just going to give her space to show up.” — Damianne
What did it actually take to get on the first plane?
I didn’t become a solo traveler because I had a moment of clarity. I became one because Ontario had too many teachers and I had student loans. A practical decision led to the first international move, and the first move changed what I thought was possible.
India was my first country, and that turned out to matter a lot. It’s confronting in ways that are hard to describe if you haven’t been: the crowds, the absence of the personal-space bubble I’d grown up in the Caribbean and later Canada, and was faced with a new world. The first thing that stood out were the people staring out of curiosity and the standards there that were different from anything I’d encountered before. I had to learn to ask, on the ground: what is actually happening here? Am I genuinely unsafe, or am I just uncomfortable? That process, repeated over months, built something in my nervous system that carried me through Sudan, Japan, and eventually Prague.
I chose each subsequent country deliberately. I picked places I had never visited, because going somewhere unfamiliar meant no expectations. And the question with solo travel is never really whether you feel ready. It’s whether you want the stretch.
What does it mean to watch your life from a window?
The Sufi teacher in India, Zafar, did a crystal healing session for me (in the back of his rug and jewellery store). He said he could see that I was in my life but just watching it. Like I was on a train and my life was passing by outside.
I recognized something in it that I hadn’t put words to. I was making decisions consequentially more than actively. Things happened and I responded. I wasn’t the one deciding. I was in my mid-twenties, living abroad, adventurous by most people’s measures. And still watching from the window.
It took me a long time to learn to do that differently. It didn’t happen in one trip or one conversation. There wasn’t a specific moment where it clicked. But I think that reading is where something shifted in what I was paying attention to. I started noticing when I was waiting for my life to come to me and started asking what I actually wanted to decide.
What is the difference between searching for yourself and meeting yourself?
In Laos, I met a woman who had been traveling for three years. She was looking for a place where nobody spoke English so she could find herself. She kept finding people who spoke English, and she was frustrated. She thought the right country would unlock it.
I thought about her for a long time because I think she had already found herself. She was right there. What she hadn’t done was stop long enough to be with whoever she found.
Searching keeps you moving. Meeting yourself starts from a different place: you know you’re already there. You’re giving her space to show up in the way you’re ready for. And what you’re ready for changes, which is why this isn’t a one-time thing. The question worth sitting with after every trip isn’t only what happened, but who came home and what she noticed.
What do you do when the sand turns out not to be water?
This isn’t just a conceptual shift. It also shows up in the body, in real moments when you’re somewhere new and things go differently than you expected. Japan gave me three questions I use with clients and still use myself.
I went to a spa in Japan expecting to be submerged in fermented rice water. It was sand. Fermented rice sand, up to my ears, cotton balls stuffed in on both sides. My heart was racing. I could feel pulsing in my head. I thought: I don’t feel okay.
The process I use with clients, and used on myself in that moment, is from Tara Brach: RAIN, which stands for Recognize, Allow, Investigate, Nurture. Recognize that something is happening. Allow yourself to feel it without fighting it. Investigate why, staying curious instead of alarmed. And then nurture: what do you actually need right now?
What I needed, in that sand, was five more minutes. Not a full commitment. Just five minutes, and then I’d check in again. That’s a tool that applies beyond spas and unusual sensations. Not “can you push through,” but “can you give it five minutes and see?” It’s also how I think about a lot of decisions in solo travel: you don’t have to commit to the whole thing. You just have to commit to the next step.
The third question I carry into unfamiliar territory: how can I have 20% more enjoyment in this moment? Not total comfort, not a transformation, just 20% more than I have right now. I learned this from a course I took from Art of Accomplishment and used it at an onsen in Japan when I was feeling self-conscious about being there at all. It shifted what I was looking for, which shifted what I found. I went back every chance I got after that.
A small invitation
If you recognized yourself anywhere in this, whether in the woman watching from the train window or the woman in Laos still looking, this is a good episode to sit with. Kellie asked me questions I hadn’t asked myself in a while, and I answered them differently than I expected.
If you’re newer to spending time alone and want somewhere to start, the Go Alone guide is free: freedomlookslikethis.com/goalone
And if this conversation brought up something you want to keep thinking about, come find us in the Skool community. That’s where these conversations continue between episodes.