SSP155: I Wish I had known this before traveling the world with my girlfriend as a digital nomad
10 May 2025 · 13 min
This is a podcast episode titled "SSP155: I Wish I had known this before traveling the world with my girlfriend as a digital nomad," recorded in May 2025. The content features Jordan Candlish sharing personal insights and lessons learned from traveling the world with his girlfriend while running an online coaching business. He discusses topics such as investing in environment, maintaining spiritual practices, managing relationship dynamics, handling anxiety and grief related to travel, and staying focused on business goals. The episode is a solo monologue-style talk rather than a multi-speaker conversation.
Want to know the brutal truth about being a digital nomad couple? After three years of traveling the world with my girlfriend while scaling an online coaching business, I've learned some game changing lessons along the way that no one talks about. Here's what you need to know before taking the leap. Number one is invest in your environment. When we first started traveling the world Back in 2020, we went to Bali and we were kind of on a budget. You know, like you're early on your business journey, you're looking for the cheaper accommodation. I remember staying in Bali in these kind of homestays where you would have a small room in a larger space where other people were living as well. And I remember being on my laptop, having nowhere to take calls, taking calls from my bedroom. And it just really impacted the quality of our relationship, impacted my creativity because my environment wasn't supporting that. And the later we got in this journey of traveling and investing in Airbnbs, we realized that the environment was really conducive to our creative potential. And the more we spent a little bit more on having a beautiful space with a nice view, with good natural lighting, and having different rooms where we could have space from each other, our relationship improved, our content improved, and we ended up making more money. So invest in your environment. Number two is don't get lazy with your spiritual practices, especially when you're traveling with your girlfriends. Now, for me, I had a really strong meditation practice early on when I was living on my own, before I met my girlfriend. And the moment she moved out to Australia with me and she's from Canada and we started traveling together, I noticed myself getting lazy with showing up in meditation, doing my yoga practice, doing my qigong practice. And it's because I was in this mode of thinking, I was on holiday. And the more I got lazy with these practices, the less I had the emotional availability to have fun, be relaxed, be present around her, because I was in my head a lot. And I realized this is so important for men. Like we got to have practices and rituals in our life that get us back into our bodies, that allow us to feel more and think less. So it's so important, even more important in fact, when traveling to have that. So I made it a priority, no matter where I am, no matter who I'm with, my non negotiables, I show up in meditation every single day. That helps my business, that helps my relationship, because they get more of me and more coming from heart centered rather than mind centered. And the third lesson that's so important that I'VE realized after, especially over the last year of traveling from six different countries throughout the world, living in multiple different environments is that every time I move into a new Airbnb or I go to a new city or I change location, it's like a blank canvas for me to install new habits, new rituals, and new routines. It's a fresh start. Now there's a negative. The downside of that is if you have good habits and rituals already installed, they're broken and you got to go back to square one. But I choose to see it as half full because now I have a new chance to install something that maybe I lacked at the previous destination. So that could mean maybe it's a. A health routine, Maybe it's not checking the phone first thing in the morning. Maybe it's getting straight in some deep work. These habits. Our environment is really anchoring our habits. It's anchoring our thoughts and our emotions. So be very mindful. At least what I do now is I'm very intentional when I first go to a new environment is what can I start to anchor? What can I reinforce through good habits? Early on the piece, it was a lot harder to break that once they're already set in stone. The fourth lesson that I've discovered, you know, whenever I leave an Airbnb, especially a city or an environment I'm really loving, you know, for example, I really love Mexico City. I'm in Mexico City, and a good creative flow and just the energy is so supportive for me. Whenever I leave, I just feel this little bit of grief. There's almost like a grieving process because there's a chapter or a phase in my journey that's coming to an end. And early on, when I first started traveling, I almost resisted this grieving process. I was trying to cling to these environments that were working for me, and I was almost attached to, like, I didn't want to let this go. I can just stay here forever. But it was almost a spiritual practice in that for me, where learning to detach, learning to accept that grieving happens all the time. Grieving happens in these micro moments. And the more I committed to being better at allowing the grief to be processed, the easier it became for me to grieve the larger moments in life. Right? And we all know what they are. So embrace the fact that you're going to have some sadness when you leave a city, but just know that there's something new and fresh on the other side of that. The fifth lesson is now following on from the grieving process of leaving an old environment. There's also an anxious anxiety destabilization process that comes up when you move into a new environment, Especially after going from a city like Toronto in North America and then flying out to, say, Colombia or Medellin. I found that there was just a bit of anxiety or destabilization because, one, I'm in a brand new culture, in a brand new kind of landscape that is kind of destabilizing for the nervous system and the mind. And I've now allowed or accepted and almost embraced this bit of, like, uncertainty, this bit of confusion and worry that comes up to be like, huh? Like, I'm trying to find my grounding, trying to find my place here. And just know that if you're choosing to travel and explore different cities, that this is a part of that. Because my mind likes to cling to routine. My. Like, my mind likes to cling to certainty sometimes. And that's why. That's why there's so much growth for me and traveling and running a business and being in a relationship, because I'm learning to dance in the unknown. I'm learning to be okay with a bit of uncertainty and a bit of anxiety. And that comes up. The more I've done this, the more I've realized that, hey, I can. I can move into any environment and I can flow when I can find my flow, when I can find my heart, I can find my peace, can find home, because home is where the heart is at the end of the day. So embrace the anxiety moments. Embrace the little period. It usually lasts for about 24 hours. What I found. And once you get to the other side of it, you realize it takes about two days to find stability, to find your flow. You can function anywhere. Now the next really important lesson that I. I learned last year when I was living in Portugal during the summer was I had multiple friends coming out to visit. They were passing through Europe, passing through Portugal, and they wanted to catch up. And I was like, yeah, sure, let's hang out. Good friends that I've known for many years, but they're on holiday and we're going out for dinners on a Tuesday night, and they're drinking wine. They came back to our place. It's 11pm and I'm, like, looking at the phone and my calendar the next day, knowing I got a bunch of client calls coming up. And I'm feeling this resistance to being around them because they're in this mode of drinking and having fun and just doing whatever the hell I want during the week. But I was still in this mode where I was trying to get dialed. I was trying to show up in my business with my clients. And I realized that when traveling you've got to be really mindful of who you're around. You know, don't get distracted by people are in the holiday mode, especially if you're growing a business, especially if you've got goals that you've said that you're committed to. So it's about, it's kind of the downside of being a digital nomad and entrepreneurs that hey, if you're in the European summer, most people that are traveling to Europe are on holiday. But you can't get swept up in that energy. Stay focused, have boundaries. It's okay to have a bit of fun every now and then. But during the week for me, between Monday to Thursday, even I'm dialed, there's no going out, there's no drinking. Stay focused on the goal. And I enjoy the downtime more when I know I've showed up for myself during the week. Now the next really important lesson is if you're in a relationship and you're traveling together. And in my case, I run a business with my partner Amanda. She's my head of marketing. And something that we really struggled to do early on when we were traveling to different countries. We went from Australia all the way out to Canada. We spent a summer in Canada back in 2023 and we were catching up with all these friends and was so much happening. We're going out to concerts and festivals and during the day there's all these things happening. It was a really fun period. But because we were so busy, we had lost sight of the deeper connection with each other. We had lost sight of prioritizing relationship check ins, moments of intimacy where we weren't being pulled around in different directions. And as a result our relationship, we started to go in different directions a little bit. We started to lose sight of each other's needs and showing up for each other. So the lesson in that for me was making sure no matter where I am, we have something in the calendar. Amanda and I, we have something together where we're getting to be intimate, we're getting to have some fun, or we're getting to open up about what we're both feeling and maybe the direction, the vision that we have for our relationship. And I believe as a man, it's so important to initiate that, to keep bringing her back to what is the vision you have for each other so that she feel, she feels reassured, she feels aligned with the direction that we're both heading. So make sure you have that in the schedule, you know, and even if you're not traveling, that should be non negotiable once a week, have a check in, maybe you go out for a coffee together, you're for a walk, you're for a nice dinner some time where you're not distracted, you're really connecting. Because remember, this is the most important person in your life right now and you're trying to, you want to nurture that relationship no matter who you are, no what matter, matter where you are, no matter who you're with. The next point that I've discovered that is so, so important when traveling with your partner is go out of your way to organize booking hotels, Airbnbs and flights for them. I personally don't want my partner in her head having to figure out plans to find the cheapest flight or to find the best Airbnb, ideally get it done for them. And I noticed recently when I started to do that and I just gave my partner permission to just say I got it sorted, I'm going to get paid, my system's going to book it, whatever. She can just kind of relax and be that support system for me that I really need, that playful feminine energy that really nurtures and supports me when I'm trying to grow my business. I want to support her in staying in that place as much as possible. So I would suggest when traveling with your partner, go do some, do some research in advance. If you go into a new city. For example, I was in Cape Town last year and first time for both of us traveling to Cape Town, beautiful by the way. I looked in, I had some friends that lived out there and I did some research to find out where are the safer areas, like where's the best place to stay? You know, what should we be mindful of is use tourists, going to probably one of the most dangerous cities in the world and in doing that allowed for us to have such a beautiful experience and she felt safe and she felt supported by me during that. So as men, don't overlook this super important. The next key point is if you're spending a lot of time together while traveling, make sure you carve out some space to be on your own. Now this for me is super important because it's so easy to overlook it. You know, you're traveling with maybe your best friend, your romantic partner and you're doing everything together, but you don't want the, the lines to get blurry. You don't want your polarity or your attraction to be diminished because you're spending so much time together. Go out of your way to spend some time, go and find a yoga class, go and find a studio, Go and find a place in nature where you can have some moment of reflection to contemplate, to be in your own energy a little bit. What I found, it kind of resets the energetic parameters between both of you, and you're both able to come back to the relationship reinvigorated. So prioritize that when you're on the move, find some time on your own, and you'll actually take in a lot of from different cities and different cultures and meeting new people. Because sometimes I know for me, when I'm traveling with my partner, we go into our own little bubble sometimes, and we're sometimes less likely to go out and meet new people because we're just so in each other's energy and we enjoy that. But it's beneficial for me and expands me when I go off my own sometimes, meet some new people, and then come back to the relationship with more confidence, more love, and more presence. Now, the next key point that I've realized after the last three years of travel and moving around to I've lost count of how many cities at this point, is that it takes two weeks, minimum of two weeks, for me to actually make a fair judgment on an environment, whether it's supportive for me. When I first started traveling when I was 21 and I did my first Europe trip with my friends, we're doing two days here in Barcelona, three days in London, three days in Prague, three days in Croatia, and you're just partying, you're on the move so quickly, it's really impossible to have a clear interpretation of whether this environment's supportive for you or not, right? And now that I'm in my later 20s, early 30s, and I'm traveling, I'm spending a minimum of two weeks at a new environment. And then I can get to really feel okay. So this is what it would be like to live here. And one of my favorite quotes is from one of Matthew Conaghe's book's Green Light. And he says he doesn't leave an environment when he's traveling until he can comfortably say, huh, you know what? This can be my existence. I can be at peace here. And I love that. Because if you can't find peace in this environment, you're not going to find it in the next environment. You don't want to fall into the trap of always looking to change your external Environment to find some sort of emotion. Find it here and now. Don't let the external determine your internal. And I love that because being too weak somewhere allows me enough to just really settle in and embrace maybe the discomfort, embrace some of the loneliness or the uncomfortability that comes up when you don't know anything or anyone. So I love that two weeks, guarantee it, then you can make a fair judgment. And if, even if you have found peace, at least me, sometimes I do find peace. And okay, I'm at peace, but I'm done, I'm complete. I'm ready to move, you know, so give it that two weeks and I promise you'll know a lot about yourself. Now, the final two points here, this one, I'm going to combine them together. This is key for me. Now that I've done my tourist travel, I try to avoid tourist areas as much as possible. For example, when I'm living in Lisbon and in the summer, all the tourists will go to these very specific areas. And whenever I walk through there, I just don't like the energy of being around lots of people who are on vacation. Nothing against them, but I'm in my own flow and I want to kind of have some separation from people who are in a different energy. So I make sure when I go to new cities now, especially in Europe in the summer, I avoid the tourist areas. And you'll thank me for it because you'll find other people who are on that vibe too. And a lot of the expats and digital nomads are usually away from some of the tourist areas. And then the second point that I want to make on that is always be grateful. You know, it's so easy to forget that if you're traveling and working online, you're living the dream, at least for me. I used to be working as a corporate accountant when I was 22, working in an office from 9 to 5, doing a job that I didn't love. And this was my dream. So I have to remind myself all the time to be take it in. Like, wow, this is so special, you know, that I'm living this life because sometimes things get hard and things don't go your way and traveling can be fucking annoying and you can lose that gratitude. So I try to remind myself all the time to come back to the heart, take a moment of appreciation for the life, this beautiful world that we get to explore. And that always feeds back into my experience and always feeds back into my relationship when I'm coming from a place of abundance and appreciation. There we have it, guys. There's the lessons. Let me know what resonated. Drop a comment below. I'd love to hear from you and we'll see you in the next video.
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