How does it feel to be a digital nomad single mom? Is full-time traveling as a single parent even possible? What are the biggest challenges? To answer these questions, I invited my dear friend Shay Lavelle for an interview. Shay is a mom of two, living the nomadic lifestyle with her daughter, Willow. When she’s not parenting, she helps aspiring entrepreneurs and influencers build strong, authentic personal brands. You can find her on Instagram @shaylnn.lavelle.
One sunny morning, we sat together in a cafe in Koh Phangan, Thailand, and chatted about her life as a Digital Nomad Single Mom.
Starting the Digital Nomad Journey
Can you please tell us a bit about yourself and your journey to becoming a digital nomad?
My name is Shay, and I’m a single mom living in Koh Phangan, Thailand. We started our digital nomad journey in the United States a little after COVID when it felt like my traveling dreams were about to shut down. And so I found a window of opportunity to leave. Within two weeks, I packed up all our stuff, and we decided to go to Mexico. It felt amazing.
Honestly, I didn’t know how I was going to make it work. Taking that first step was probably the most liberating thing I’ve ever done for myself and my family.
So, did you start as a digital nomad single parent, or did you become a single parent while being a digital nomad?
I started as a single parent and went into digital nomading. It was both amazing and challenging. Amazing because I overcame many limiting beliefs, like thinking I couldn’t do this because I’m a single mom, or because I have kids, or that others could do it because they have money, a partner, or family support.
I felt proud of myself for rising above these beliefs and just doing it anyway. I didn’t want to give up. I have a little girl who’s always watching me. Even though she can’t hear my thoughts, she sees my actions. I want more than anything for her and my son to be free in their lives.
The biggest lesson I can teach them is by embodying and demonstrating what freedom looks like. So, I had to do it. At the time, I had a coaching business. I shared this journey with my clients, telling them that if I didn’t take the leap into uncharted territory and lead the way, I couldn’t lead them. This was another important aspect.
Lastly, I felt like I was inspiring many single moms who feel like they can’t do it because they’re separated, don’t have a partner, or face custody issues. I showed them a path to how they could do it. I documented much of the journey, and it was amazing.
How old was Willow when you started the digital nomad journey? Did she express any concerns at the time, or was it all a big, exciting adventure for her?
Yeah, she was really excited. We showed her pictures of what Mexico would look like, which is where we were headed at the time. She had no fear or insecurity at all. The only thing she worried about was not being separated from her brother since they had always lived together. She was five when we left.
Overcoming Challenges as a Single Parent Traveler
What were your biggest fears or concerns about traveling as a single parent? How did you overcome them?
One of my biggest fears was money. I worried if I had enough to sustain myself and my daughter. I had to break it down and look at my finances. I projected that even if I couldn’t find work for three months, I had enough savings to get by. That was our emergency fund. About two months in, I realized I had enough to fly back home if needed.
Doing this as a single mom, I worried about what would happen if something went wrong. I didn’t know anyone there, had no help, didn’t know the area, and didn’t speak the language. But I decided to figure it out and not let fear stop me. It turned out that I had moved into the same neighborhood as another woman I had followed on Instagram, and we had become friends. Many people in the area spoke English, which was really helpful.
Landing in a place with some English speakers made a big difference. Learning the language as you go is also important. It’s wise to find a place where you can communicate with at least some locals in English.
I also needed to know where the hospital was, my emergency contacts, and my route in case of an emergency. I identified doctors’ offices, pharmacies, places to get healthy food, and where to find a nanny. Having these plans and knowing where to find essential services were crucial for me.
So, is this something you’re researching before you travel?
I didn’t at first. I realized that all these fears were set in the moment I landed. But since that first lesson, yeah, that is something that I researched before I go. So, it eases my anxiety.
Strengthening Parent-Child Bonds Through Travel
How has being a digital nomad impacted your relationship with your child? Maybe there were some memorable experiences that glued you even more together?
Yes, I do most of my business on Instagram, which includes a lot of content creation and filming reels. Sometimes, I have to come up with ideas for what to film, so I scroll through Pinterest for inspiration.
What brought my daughter and me closer was that she wanted to learn what I was doing. She’d ask what kind of exposure she needed with certain lighting. She saw me on Pinterest and asked if she could help pick content for us to film the next day. My work became part of her education, which was really fun.
The homeschooling aspect of our lives brought us even closer. Growing up, trips with my family were just trips. They would put me on the plane, were there at Disney World, whatever. But with my daughter, I’m always thinking about how to make our travels educational. Whether we’re on a boat, figuring out how to get a scooter, or navigating the airport, I teach her how to handle these experiences.
I’m confident now that if I took her to the airport and told her to take it from there, she would know what to do and where to go. It’s a really cool bonding experience that we always share.
Managing Emotional Highs and Lows of Traveling as a Single Parent
How do you manage the emotional highs and lows of regularly adjusting to new places and new environments?
Do you provide something like this for Willow, too?
When I travel, I usually bring my own sheet or pillowcase because I like my own bedding. This might be more than others would do, but it’s important to me. Willow has always had a baby blanket that I bought her—a special organic flat sheet she’s used for nearly eight years. She never sleeps without it. So that is her constant.
We also maintain a consistent bedtime routine, no matter where we are. This often involves tea, which we can usually make with a kettle provided by hotels or wherever we’re staying. In the evenings, we have tea time, decompress, chat a bit, and do some stretches before settling into our bedtime routine. This consistency helps us both feel centered and stable, even when we’re away from home. No matter where we are, there are certain things that don’t change in our lives.
The Everyday Life of a Traveling Single Mom
Can you walk us through a typical day in your life as a single digital nomad mom?
No, not so much. It’s pretty unstructured right now. I do feel like I want to find something that includes more academics. At first, because we were moving around so much, it was difficult to follow a format. But now, I think it’s nice to have online classes so she can interact with other kids. I like to support whatever she’s interested in. If it’s cooking, then we’re doing cooking classes for a month. If it’s bugs, we’ll get a microscope and explore bugs for that month. It’s really up to her.
The way I do things is child-led. Right now, she’s really into photography, filming, and editing, which is great for me because I feel like I have a personal assistant. While she’s learning about these things, I’m able to get my work done. It’s a perfect match that she’s interested in that.
Building a Support System
What kind of support system do you have in place while on the road? Other people living the conventional lifestyle have their grandparents and maybe friends or specific nannies around them to help through the day with the child. How do you do it?
While I’m here and staying put, I have a nanny on call, but I rarely use her. Willow has certain friends she’s close to, so we arrange play dates and occasional sleepovers, which gives me some time to myself.
We’re also working on Willow’s independence and overcoming her fear of being home alone. Sometimes I need to run to 7-Eleven quickly, but she’s scared even if I’ll be gone for just five minutes. We’re working on helping her feel safe at home by herself for short periods.
The other piece that I want to add is that it’s hard to have constant support when you’re moving around a lot. And coming from someone who’s really introverted, it takes a lot longer for me to get to know someone and trust someone, and it’s the same for Willow.
And the other thing that’s been really helpful is phone calls. If I need to leave the house or have a moment to get work done, I can call someone on video and have Willow stay on the phone with them in a different room. This has been really helpful.
The Biggest Challenge of all
What was the biggest challenge you faced as a traveling single parent? And how did you address it?
My biggest challenge is still ongoing and involves my son. (Shay had to leave her son in the US and left only with her daughter Willow) It was an incredibly difficult decision, feeling almost impossible. Many single moms face custody restrictions, preventing them from leaving the state or even the city.
I had to consider this because I was extremely unhappy where I was. Should I stay and risk falling into depression, giving only a fraction of myself, like a ghost of who I am, to my kids? Or do I leave, make myself happy, and show them a fuller, better version of me? I chose the second option.
This choice was hard because it meant limited to almost no time with my son, turning our relationship into a long-distance one. It was tough for my daughter too, as she and her brother grew up together. My son had been with me for the first 11 years of his life.
The transition was challenging for everyone. Though we have a long-distance relationship now, my son is excited about the life he can join whenever his dad allows it. There have been disagreements, but it’s a reality we deal with. It breaks my heart and has been incredibly difficult to navigate, leaving a child in a different country.
Willow’s dad was also leaving the country, so I had to choose between my children. At the time, Willow needed me more since she was younger, while my son, almost 11, had a strong foundation. So, I chose to be with Willow, leading to a temporary long-distance relationship with my son. He has been able to visit, which is good.
I’m still working on reuniting my family. I want us all back together, and it’s a work in progress.
Advice for Aspiring Nomad Parents
What advice would you give other single parents considering a digital nomad lifestyle?
I just want to say, just do it. There’s only so much time while they’re kids, and it’s so worth giving it a shot to provide them with a memorable childhood. Instead of the typical nine-to-five routine with them being raised by teachers and babysitters, experiencing different places firsthand is invaluable. They should learn about countries and cities by visiting them, not just from books.
Whatever challenges you think you have, they can be overcome. We are capable of moving past these obstacles. If making a big shift, like going out of the country, feels uncomfortable, start small. Take a weekend trip, then gradually extend the trips. Leave the city, then the state, and eventually go across the country. I did this to get comfortable with traveling, and soon it progressed from city to city, state to state, and now country to country.
There’s only so much time while they’re kids, and it’s so worth giving it a shot to provide them with a memorable childhood.
Rewards of the Nomadic Lifestyle as a Single Mom
What is the most rewarding aspect of being a digital nomad single mom and traveling as a single parent in general?
I don’t have to share my time or compromise on what I do with my child. I have the freedom to do whatever I want. Right now, my daughter and I have a new schedule: one month on, one month off. She spends one month in the city with her dad, and then one month living island life with me.
The most rewarding aspect of this arrangement is the freedom. When I have her, we can stay here or travel to different cities or go on vacations. When she’s with her dad, I have the freedom to do what I want, like traveling to Bali or visiting another country.
Surprisingly, being a single parent offers a lot more freedom than you might think. Many single parents feel their freedom is cut in half, but in reality, it can double because you no longer have to share decisions with someone else. Your time with your child is entirely your own.
Favorite Travel Destination
What is your favorite travel destination, and why is it special to you and your child?
I think my favorite destination is here on Koh Phangan, Thailand. It’s special because ever since Willow could talk, her dream has been to go to a beach. We used to live far from any beach, in the middle of land. Being here, with access to so many beautiful beaches, I’ve been able to make her dream an everyday reality.
It’s also special for me because I didn’t even know this island existed two years ago. In my manifestation journal, I wrote about living in a bungalow in the jungle, but still within walking distance of the beach. The only place I could think of was Hawaii, but I didn’t want to go there. I kept journaling about this ideal place. Eventually, someone told me about Koh Phangan. I looked it up and realized it matched my journal entries. It’s been amazing for both of us to see this dream, which I’ve been pinteresting for years, become a reality.
How the Lifestyle Has Changed Shay
How has the lifestyle of a digital nomad single mom changed you and your perspective on life?
It’s changed my sense of what I believe to be important. My perspective on how I choose to spend my time has shifted. In the digital nomad life, work is still a priority, but it no longer consumes my entire life. It used to feel like being in a cage, stuck in the matrix, with an emphasis on collecting things and how they make you look, and the positions you hold in society.
All these things seemed irrelevant once I left that society. Coming to the island, where you have to get rid of possessions because they get moldy, changed my attachment to material things. The focus on how much money you make, how nice your car is, or how fancy your house is—all of that went out the window.
This experience has been liberating. I’ve freed up so much mental space by not worrying about things that aren’t really important. I still like nice things, don’t get me wrong—I would love to have them—but the competition to have better things than the person next to me is no longer there. It’s been a freeing experience.
Is there anything you’d like other aspiring nomad parents to know?
I feel like many people have this dream, but they often say, “I don’t know where to start.” What I want to say is, you do know, and you know where to begin. You know the first step you need to take.
If you want to become a digital nomad, one of the first steps is figuring out how to make money online. These are simple steps. Just take that first one, and it will unlock all the following ideas for the rest of the journey.
So, don’t tell yourself you don’t know where to start or what to do because you do. We all know these things if we really tap into our desires. The answers are there; you just have to listen.
Thank you so much for this Interview and for sharing all these inspiring and helpful insights, Shay!
Did you like this Interview? Do you have any questions? Please let me know in the comments!
Thank you for reading and for making this blog part of your day! Yours, Lulu
