Thank you. What a wonderful post. I enjoyed reading your story. Life is what you make it. It's good to be part of a community. To feel at home somewhere. I am an international house sitter. My husband and I like to take on mid to long term sits so we can stay in one place for a reasonable amount of time. We get involved in the community and like to live like a local, not a tourist. Travel is our passion and there is so much out there in the world to explore and wonderful people to meet along the way. All the best.
That's super cool Rosie, I admire that. I have a really strong desire to put roots down and have a home. But I understand that not everyone is like that. I admire those that don't need any specific location ties to feel whole.
Do you ever think about putting down roots? Or do you intend to continue that lifestyle forever?
Kaila, what a beautifully written piece. You always do a great job of connecting external events to the deeper emotions beneath. I, too, am at war with the exhilaration of freedom and novelty versus the allure of comfort and stability, and I think I always will be. However, the peace I've tried to make with my life is the knowledge that I can have it all, just not all at once.
I can totally relate. When I moved to London, I was a freelance writer working in cool cafés all over the city. The dream! Only I felt excruciatingly lonely, was working 24/7 and had to chase invoices constantly just to make the rent. When I woke up with a fever and realised that I would still have to write today, otherwise I couldn't pay the bills, that was the end. I went back to employment (while freelancing on the side) and have never looked back. Finding the right job, though...that was a whole different story!
Damn - why do we always feel like we have to run? I tried to put an ocean between me and the pain I was running away from but the reality is that it comes with you and you have to work on yourself to heal. Thank you for sharing your story and being vulnerable. I hope you'll experience the freedom you need and that you are enough!!
Thanks Francesca. It's true, you can't just run away from it, you have to face it eventually. And/or, you'll find a whole new set of issues wherever you go.
I'm slowly learning that I'm enough. It's weirdly hard to accept!
I was 20 when I was first married. I had never been out of the US, but always dreamed of traveling. My husband had a good job and I remember him saying we should start to look for a house. I panicked, picturing a future of mortgage payments, 2.5 kids, a dog, only two weeks off a year for a planned family vacation, and constant, stifling responsibility. For good or ill, I built a very different life for myself. Now I’ve traveled, had four kids, divorced, remarried to a man who supports my dreams, and had more struggle than I ever would have thought I could handle. The ironic part is that in this point of my life, I would give anything to have a stable income and be able to afford a house for my children in this economy.
I enjoyed this essay and felt I was living your life with you. When I was growing up in 70’s and 80’s the tension for women was often between marriage vs career. Those were the adventure options. I’m gay and had 10 years of adventure (mostly in Russia) after college and am now married to a well-earning man and have 2 young children. My dissatisfactions can be traced to not being self-supporting and all the problems that come along with that. Have you ever tried to solve problems by thinking the right guy is the answer? That seems the more common form of escape plan.
Literally never. It never appealed to me to lean on someone. Ironic, because that's what I'm doing now. At least until the Substack thing takes off 😔😅
I'd love to hear more about your 10 years of adventure in Russia! And I seem to remember you saying that you still had a hankering to live abroad, have you made any headway on that? I know it's so much harder with kids.
I’m at the gathering birth certificate phase and next need to sell house and choose where on the planet makes most sense. Discomfort with the news is growing and hopefully will push me to make progress. I’m visiting Mexico next month with my 3 yro daughter.
Do you trace your independent spirit to an early influence?
Good for you, Luke. I know Mexico is starting to clamp down on visas, but then, so is everywhere! Do you have a locale in mind? I know a bit about the place.
What a great question. You've given me pause. My dad was always a lone wolf, so probably influenced by him. But I think more than anything it was that I never felt accepted or like I fit in and have always had such a strong desire for that. So since I didn't get it where I grew up, I left to find it. Still looking! haha.
Great to read your story Kaila - I relate to this and the other two articles you tagged at the start. I have lived 20 years abroad in 10 countries - I wasn't working as a digitial nomad, but in the development sector and I had a similar experience of feeling rootless trying to make home in places which clearly were not meant to be my long term home. I unexpectedly find myself in another of those tranisitions spaces now and take comfort in the new in-between space you have built for yourself in Spain. thank you
This is such a wonderful piece of writing Kaila. Your comments around anchoring definitely resonated as someone who decided to move into a van and travel full time. It's the small rituals I do every day that have helped me to slowly build the mobile foundation (what a lovely turn of phrase that is!) I need to write//to feel at home on the move. Thank you for sharing, EJK
Love this so much!! As a fellow Canadian looking to relocate and follow the sun, to put down roots in a new Home somewhere dreamy, it's good to be reminded that the grass of freedom isn't always greener. It's just different grass. I love that you sorted out how to anchor your Self into a supportive routine. As within, so without. ✨
I have a few ideas- most certainly towards the sun!!
Mexico? Greece? Panama?!
I've not yet been to any of these places which makes it trickier to commit and truly leap. I'm currently immersed fully in research-mode so discovering your stack yesterday is divine timing!
Wow, what a beautiful heartfelt piece. I can relate so much. I spent my twenties chasing this exact dream of getting out, of travelling and working, of being free - each time only to return to big jobs in big German cities, quitting them after 2 years and doing it all over again, I’m not sure I even knew what I was looking for, but None of it was it.
I remember travelling Ecuador, just me and my backpack, something I’d been dreaming of for so long - and then I sat in a small, homey hostel in Montanita, just blankly staring at my laptop, the sense of dread and loneliness slowly creeping up to me while everyone else was partying hard and enjoying the sh*t out of themselves.
When I hit 30, I moved back to the small, countrysided German hometown where I grew up, started working as a freelancer here and it’s the first time I felt like I belonged again. It’s been 5 years and I love it – Life here has its downsides, of course, and the urge to run never really goes away, but it’s a different life, a different structure I’m building now: one where I can go spend several weeks or months a year in my favourite places around the world (for the past 5 years, it was Greece& Canada), and at the same time have my homebase right here, right where I came from – and where I’ll always return to. Financially tough sometimes, and of course I can’t travel as much as I’d like to while I’m simultaneously paying rent and everything here at home – but for now, that’s my idea of a rich life and of making the best out of both worlds. I’m the happiest I’ve been in ages, because I finally feel safe. Wishing you all the best and that this feeling awaits just around the corner for you. Thanks for your honesty and inspiration.💜
So funny how we think freedom will make us happy and in the end, discover that it's actually safety. Or is it that our priorities change along the way? It's so nice that you have your hometown to go back to. That is a richness, to me. Good for you for figuring out what works best for you, Kim!
Oh excellent, so well put. Often from the outside things do look rosy, but doing the daily stuff may not seem like a lot if you're 'sitting in paradise.' I totally understand. We thought out our dream, and lived our dream, owning an incredible bookstore in a fishing village in southern Mexico, and it was really fun for a long time. But finally, having a schedule, showing up, being there, became a job, like the ones both my husband and I had retired from. We wanted to re-retire. Our actual goal had been to have the shop as a hobby, but it took off--there are few bookstores in Mexico (and now we know why, haha, no easy feat). So we sold, to the perfect new owners, and then we were free to again travel to more pyramid sites or abroad, sit on the beach ANY day, snorkel at the reef, of head down to Belize or over to Isla Mujeres. I think one of the keys--to mental survival-- is knowing when to quit. We'd founded a wonderful bookstore and then passed it on. It's in good and capable and creative hands. Ojala, as the Maya say.
You did it, Kaila! Your life really seemed like full tilt boogie. I hope you enjoy Spain as much as possible under the circumstances of your recent loss.
That's synchronicity finding your post today. My big thought of the day has been: What is my idea of success? At first, I thought of freedom. But freedom to do what? To go where? I realized that true success, for me, is the freedom to set my own rules, be at peace—deep within myself. At peace with my choices, my breath, my very being.
At every phase and at every age, freedom comes with a price. And it isn’t the cost of a plane ticket. It takes doing the work to find balance, to find peace, to be able to make the constant decisions without going crazy. To fight lonliness sometimes. To resist going back in to something that appears more stable and easier. To revive your energy and passion when you have absolutely no guarantees and you don't know where you will be sleeping next year, next month, next week, tomorrow night. Maybe to support the other people in your life who jumped aboard the free life or you are dragging along with you (kids/pets). A price. Yes. But so does the other life, every other life. They come with sacrifices. They require their tenants to do the work too. The only difference is that along with this free life we are cultivating a freer mind, freed time, freedom to see, feel, understand what is beyond the boxes of systems and contained societal expectations. It is not impossible to grow in the other life, however the space we create supports our growth in a way no type of box can. And this is priceless. I think that it is important not to create a box called Freedom. Freedom feels better when we allow it to change with us. Otherwise, it becomes just a really great photo someone else is posting for reasons that no longer (or maybe never) belonged to you. Yes, this sense of belonging. This is freedom for me as well. And with this I am learning to free up my notion of this free life my family and I have created. I am doing this by eliminating the thought that freedom is supposed to feel easy. No. Freedom will never feel easy unless you stop seeking an easy/easier life. When you can pay the price for the life you create with ease - this is freedom. Thank you for sharing this. It is so essential to share. Because freedom feels insanely lonely without people. This is another thing I am learning. xo
So f'ing lonely, babe, yes! God it feels so good to hear other people speaking my language, speaking the words that I didn't know were inside of me, or that I knew how to formulate because I didn't fully understand just WHAT WAS WRONG WITH ME for not LOVING being free??? For so damn long. I finally get it. And though I want no one to suffer, it feels good to know I'm not alone.
Suffering is part of it and every life. It is totally normal to not want to feel alone in this. Actually, this is the beautiful side effect of suffering. Suffering brings us together just as much as joy. You are not crazy or alone. Your free life tribe sees you, understans you, and supports you. Including me.
I loved this! I really resonate with this, even though I'm at a very different place in my life as a recent uni graduate. I already feel trapped between wanting novelty and independence, but also needing structure and stability. A 9-5 sounds so dull, but I can't keep living paycheck to paycheck forever!
Thank you. What a wonderful post. I enjoyed reading your story. Life is what you make it. It's good to be part of a community. To feel at home somewhere. I am an international house sitter. My husband and I like to take on mid to long term sits so we can stay in one place for a reasonable amount of time. We get involved in the community and like to live like a local, not a tourist. Travel is our passion and there is so much out there in the world to explore and wonderful people to meet along the way. All the best.
That's super cool Rosie, I admire that. I have a really strong desire to put roots down and have a home. But I understand that not everyone is like that. I admire those that don't need any specific location ties to feel whole.
Do you ever think about putting down roots? Or do you intend to continue that lifestyle forever?
At this stage we are quite happy to keep travelling. Perhaps one day.
Kaila, what a beautifully written piece. You always do a great job of connecting external events to the deeper emotions beneath. I, too, am at war with the exhilaration of freedom and novelty versus the allure of comfort and stability, and I think I always will be. However, the peace I've tried to make with my life is the knowledge that I can have it all, just not all at once.
Thanks Elizabeth, it's definitely a dichotomy for us abroad isn't it!? It's a puzzle I hope to solve.
I can totally relate. When I moved to London, I was a freelance writer working in cool cafés all over the city. The dream! Only I felt excruciatingly lonely, was working 24/7 and had to chase invoices constantly just to make the rent. When I woke up with a fever and realised that I would still have to write today, otherwise I couldn't pay the bills, that was the end. I went back to employment (while freelancing on the side) and have never looked back. Finding the right job, though...that was a whole different story!
Oh my god, been there. How awful, good for you for realising you needed to make a change and doing it.
Damn - why do we always feel like we have to run? I tried to put an ocean between me and the pain I was running away from but the reality is that it comes with you and you have to work on yourself to heal. Thank you for sharing your story and being vulnerable. I hope you'll experience the freedom you need and that you are enough!!
Thanks Francesca. It's true, you can't just run away from it, you have to face it eventually. And/or, you'll find a whole new set of issues wherever you go.
I'm slowly learning that I'm enough. It's weirdly hard to accept!
I was 20 when I was first married. I had never been out of the US, but always dreamed of traveling. My husband had a good job and I remember him saying we should start to look for a house. I panicked, picturing a future of mortgage payments, 2.5 kids, a dog, only two weeks off a year for a planned family vacation, and constant, stifling responsibility. For good or ill, I built a very different life for myself. Now I’ve traveled, had four kids, divorced, remarried to a man who supports my dreams, and had more struggle than I ever would have thought I could handle. The ironic part is that in this point of my life, I would give anything to have a stable income and be able to afford a house for my children in this economy.
Yeah it's such a shame that it has to be a trade-off, isn't it, Lindsay! Good for you for following your heart, though.
I enjoyed this essay and felt I was living your life with you. When I was growing up in 70’s and 80’s the tension for women was often between marriage vs career. Those were the adventure options. I’m gay and had 10 years of adventure (mostly in Russia) after college and am now married to a well-earning man and have 2 young children. My dissatisfactions can be traced to not being self-supporting and all the problems that come along with that. Have you ever tried to solve problems by thinking the right guy is the answer? That seems the more common form of escape plan.
Literally never. It never appealed to me to lean on someone. Ironic, because that's what I'm doing now. At least until the Substack thing takes off 😔😅
I'd love to hear more about your 10 years of adventure in Russia! And I seem to remember you saying that you still had a hankering to live abroad, have you made any headway on that? I know it's so much harder with kids.
I’m at the gathering birth certificate phase and next need to sell house and choose where on the planet makes most sense. Discomfort with the news is growing and hopefully will push me to make progress. I’m visiting Mexico next month with my 3 yro daughter.
Do you trace your independent spirit to an early influence?
Good for you, Luke. I know Mexico is starting to clamp down on visas, but then, so is everywhere! Do you have a locale in mind? I know a bit about the place.
What a great question. You've given me pause. My dad was always a lone wolf, so probably influenced by him. But I think more than anything it was that I never felt accepted or like I fit in and have always had such a strong desire for that. So since I didn't get it where I grew up, I left to find it. Still looking! haha.
Great to read your story Kaila - I relate to this and the other two articles you tagged at the start. I have lived 20 years abroad in 10 countries - I wasn't working as a digitial nomad, but in the development sector and I had a similar experience of feeling rootless trying to make home in places which clearly were not meant to be my long term home. I unexpectedly find myself in another of those tranisitions spaces now and take comfort in the new in-between space you have built for yourself in Spain. thank you
it's a funny place, the in between. I find it uncomfortable, but there is usually growth in discomfort, so I'm trying to find comfort in that!
This is a beautiful piece. Thank you so much for sharing this with us.
Oh, thanks for saying so, Michelle. You're most welcome!
This is such a wonderful piece of writing Kaila. Your comments around anchoring definitely resonated as someone who decided to move into a van and travel full time. It's the small rituals I do every day that have helped me to slowly build the mobile foundation (what a lovely turn of phrase that is!) I need to write//to feel at home on the move. Thank you for sharing, EJK
Yes! I think we are creating a new culture. Or maybe reviving a really old one...
Love this so much!! As a fellow Canadian looking to relocate and follow the sun, to put down roots in a new Home somewhere dreamy, it's good to be reminded that the grass of freedom isn't always greener. It's just different grass. I love that you sorted out how to anchor your Self into a supportive routine. As within, so without. ✨
Yes! It's so helpful when you're on the move. Do you have any idea where you'd like to go, Jacqueline?
I have a few ideas- most certainly towards the sun!!
Mexico? Greece? Panama?!
I've not yet been to any of these places which makes it trickier to commit and truly leap. I'm currently immersed fully in research-mode so discovering your stack yesterday is divine timing!
Oh lovely! I've got some tools to help you along with that coming out this week and next.
Wonderful!
Wow, what a beautiful heartfelt piece. I can relate so much. I spent my twenties chasing this exact dream of getting out, of travelling and working, of being free - each time only to return to big jobs in big German cities, quitting them after 2 years and doing it all over again, I’m not sure I even knew what I was looking for, but None of it was it.
I remember travelling Ecuador, just me and my backpack, something I’d been dreaming of for so long - and then I sat in a small, homey hostel in Montanita, just blankly staring at my laptop, the sense of dread and loneliness slowly creeping up to me while everyone else was partying hard and enjoying the sh*t out of themselves.
When I hit 30, I moved back to the small, countrysided German hometown where I grew up, started working as a freelancer here and it’s the first time I felt like I belonged again. It’s been 5 years and I love it – Life here has its downsides, of course, and the urge to run never really goes away, but it’s a different life, a different structure I’m building now: one where I can go spend several weeks or months a year in my favourite places around the world (for the past 5 years, it was Greece& Canada), and at the same time have my homebase right here, right where I came from – and where I’ll always return to. Financially tough sometimes, and of course I can’t travel as much as I’d like to while I’m simultaneously paying rent and everything here at home – but for now, that’s my idea of a rich life and of making the best out of both worlds. I’m the happiest I’ve been in ages, because I finally feel safe. Wishing you all the best and that this feeling awaits just around the corner for you. Thanks for your honesty and inspiration.💜
So funny how we think freedom will make us happy and in the end, discover that it's actually safety. Or is it that our priorities change along the way? It's so nice that you have your hometown to go back to. That is a richness, to me. Good for you for figuring out what works best for you, Kim!
Thank you 💜
Wonderfully said Kaila. I love this piece so much. We are a family.
This lifestyle choice is sometimes hard to describe, and for others to understand why we choose it. Then you, put it in words for us. ♥️. Thank you.
Freedom forward, whatever that looks like for each of us.
Thank you so much Debbie! I'm glad I was able to help verbalize what we're all feeling.
Oh excellent, so well put. Often from the outside things do look rosy, but doing the daily stuff may not seem like a lot if you're 'sitting in paradise.' I totally understand. We thought out our dream, and lived our dream, owning an incredible bookstore in a fishing village in southern Mexico, and it was really fun for a long time. But finally, having a schedule, showing up, being there, became a job, like the ones both my husband and I had retired from. We wanted to re-retire. Our actual goal had been to have the shop as a hobby, but it took off--there are few bookstores in Mexico (and now we know why, haha, no easy feat). So we sold, to the perfect new owners, and then we were free to again travel to more pyramid sites or abroad, sit on the beach ANY day, snorkel at the reef, of head down to Belize or over to Isla Mujeres. I think one of the keys--to mental survival-- is knowing when to quit. We'd founded a wonderful bookstore and then passed it on. It's in good and capable and creative hands. Ojala, as the Maya say.
What a beautiful lesson, Jeanine. Knowing when to quit is so important, I agree.
You did it, Kaila! Your life really seemed like full tilt boogie. I hope you enjoy Spain as much as possible under the circumstances of your recent loss.
Full-tilt boogie is an excellent description 🤣 Thank you Janine. I appreciate you.
That's synchronicity finding your post today. My big thought of the day has been: What is my idea of success? At first, I thought of freedom. But freedom to do what? To go where? I realized that true success, for me, is the freedom to set my own rules, be at peace—deep within myself. At peace with my choices, my breath, my very being.
Synchronicity indeed! Glad we crossed paths :)
At every phase and at every age, freedom comes with a price. And it isn’t the cost of a plane ticket. It takes doing the work to find balance, to find peace, to be able to make the constant decisions without going crazy. To fight lonliness sometimes. To resist going back in to something that appears more stable and easier. To revive your energy and passion when you have absolutely no guarantees and you don't know where you will be sleeping next year, next month, next week, tomorrow night. Maybe to support the other people in your life who jumped aboard the free life or you are dragging along with you (kids/pets). A price. Yes. But so does the other life, every other life. They come with sacrifices. They require their tenants to do the work too. The only difference is that along with this free life we are cultivating a freer mind, freed time, freedom to see, feel, understand what is beyond the boxes of systems and contained societal expectations. It is not impossible to grow in the other life, however the space we create supports our growth in a way no type of box can. And this is priceless. I think that it is important not to create a box called Freedom. Freedom feels better when we allow it to change with us. Otherwise, it becomes just a really great photo someone else is posting for reasons that no longer (or maybe never) belonged to you. Yes, this sense of belonging. This is freedom for me as well. And with this I am learning to free up my notion of this free life my family and I have created. I am doing this by eliminating the thought that freedom is supposed to feel easy. No. Freedom will never feel easy unless you stop seeking an easy/easier life. When you can pay the price for the life you create with ease - this is freedom. Thank you for sharing this. It is so essential to share. Because freedom feels insanely lonely without people. This is another thing I am learning. xo
So f'ing lonely, babe, yes! God it feels so good to hear other people speaking my language, speaking the words that I didn't know were inside of me, or that I knew how to formulate because I didn't fully understand just WHAT WAS WRONG WITH ME for not LOVING being free??? For so damn long. I finally get it. And though I want no one to suffer, it feels good to know I'm not alone.
Suffering is part of it and every life. It is totally normal to not want to feel alone in this. Actually, this is the beautiful side effect of suffering. Suffering brings us together just as much as joy. You are not crazy or alone. Your free life tribe sees you, understans you, and supports you. Including me.
I loved this! I really resonate with this, even though I'm at a very different place in my life as a recent uni graduate. I already feel trapped between wanting novelty and independence, but also needing structure and stability. A 9-5 sounds so dull, but I can't keep living paycheck to paycheck forever!
Yeah it's a tough one! Hoping we'll find an in between place soon.