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Siblings Mike and Jessie are a unique duo in the Boundless Life community – they’ve embarked on this journey together with their two families. Between them, they have four children (Mike’s kids are 9 and 11; Jessie’s are 7 and 9) and together they share a deep passion for exploring the world. Having spent their childhood summers traveling the globe, this brother-sister pair developed a love of adventure from an early age.

In this Q&A, Mike and Jessie reflect on life before Boundless Life, the leap they took to join their first cohort in Syros, and the adventures that followed!

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What did life look like for you both before joining Boundless Life?

Mike: We had what I’d describe as traditional corporate jobs and lives. Both of us went to business school and landed in corporate jobs, living in cities because of work. But one thing we always made time for was travel.

Jessie: Growing up, we traveled overseas every summer for the entire summer for years with our parents. And we would go without an itinerary and explore. They talk about it as a great adventure when they reflect back on it, and I think it's shaped a lot of who we are. It's been incredible to travel now as adults with our own families, but do it together. So I’d say we were born into the love of travel.

Mike: A few years ago, before Boundless, I negotiated to work part-time during summer so I could travel more. It was a realization for me that this was something that was doable alongside corporate life.

Jessie: Before Boundless, I felt that I was on a never-ending track. Every day was the same; I couldn't break away from it. Now I'm seeing there’s not just one track - there's so much more out there if you’re willing to just step off the track.

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What encouraged you to choose Boundless Life, and how did you discover it?

Mike: I learned about Boundless Life through some friends, Jake and Michelle Schomp, who were part of the very first cohort. They knew I was passionate about travel and looking for some flexibility to go lead a different lifestyle. My wife and I got on a video call with them and their experience was just incredible - exactly what we wanted.

Jessie: When Mike came to me with this crazy idea – “We’re going to go live in Greece for the summer. The kids will be in school there, we’ll work remotely, and on weekends we’ll take boat rides with other families. Want to join?” – my first reaction was, “I have no idea what you’re talking about, but yes, I want to do all of that!”

And so we booked a summer cohort in Greece to test out this lifestyle and see if this experience would work for us. Intrigued, but also a little unsure how it would work out with our jobs and lives back home.

Mike: Honestly, within the first couple of days in Syros, we knew we’d made the right decision. Just two days into the cohort, we signed up for our next full three-month cohort! Any initial skepticism disappeared quickly.

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Which Boundless Life locations have you lived in so far, and where are you headed next?

Mike: So far we’ve done two cohorts: the first was Syros, Greece and Pistoia, Tuscany in Italy, where we are now. We have La Barra booked for April 2026 and we have a deposit on Japan, and so we're kind of plotting our roadmap. My wife and I have planned a full year of travel and Boundless after that, and Jessie’s family will join us for some additional cohorts.

How has the Boundless Life positively impacted your children academically, socially or emotionally?

Jessie: In every way! That's such a multifaceted question that I could spend an hour just talking about just one kid’s growth.

Mike: What I value most is their resilience to handle changing environments and challenging  situations.

We've been letting our older daughter and her friends navigate town independently to get dinner. They meet up in the square, they have money, they pick a restaurant, they work through their challenges. We’d never let our kids do this in the United States.

In addition, my kids now handle multi-day travel journeys, working through different cultural challenges, and they do it second nature now. That sort of resilience will benefit them for their entire lives

Jessie: Traveling as kids ourselves taught Mike and me to handle daily challenges positively.

Now, we watch our kids walk to the grocery store and they’re enthusiastic to participate. We bring our cart, we buy our groceries and we carry them all home. And the kids love it.

Or another example, we've had washing machines, but no dryers. The kids come out with their clothes pins and they hang up the clothes. It's just these things that they embrace because consciously or subconsciously they know that this is part of the experience and this is what they're here for.

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What lifestyle changes have you experienced since joining Boundless Life?

Mike: I’d say the biggest change is in our mindset. We’re surrounded by so many different examples of what a great life can look like. In Boundless you meet families from all over, each with their own story, and it really opens your eyes to possibilities.

We’ve been inspired to imagine better versions of our own lives. For example, within a week of arriving in Syros, my wife quit her job inspired by others making bold life changes, and then soon after started her own business.  The more we talk to other Boundless parents, the more ideas we get about how we want to live and what we want to change.

Jessie: And to add to that, something I’ve noticed is the authenticity in the community, there are no egos in the conversations we’re having around the life questions we’re asking ourselves and exploring or the struggles we’re facing.

I've just had these really candid conversations with people who are so open about where they're at, where they've been, where they want to go. It's been really incredible.

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What is your favorite thing about the Boundless Life experience so far?

Mike: Definitely the social aspect of it and making friends. Every single day I'm getting coffee with somebody, getting lunch, we're going out for drinks in the evening, we're playing games at the park. That doesn’t happen at home.

I would categorize myself as an introvert, and even for introverts, being surrounded by other people that are like you, is a really special and unique opportunity.

And then I would also say that when the parents' needs are being met, it also makes them  better parents to their kids. When I am less stressed, happier and fulfilled, I can be a much better dad which benefits my kids.

Jessie: I would second all of that. Another thing that makes Boundless unique, is the support we get from the local team.

For example, in Pistoia our Boundless team helped us when my seven-year-old son broke his glasses. He has a complicated prescription. I reached out to the Boundless team for help. They not only found a local eyeglass place, they called ahead, explained the situation, confirmed they can make a pair in his size.

Having that sort of support gives me the confidence to go to a place that I don't know, a place that I don't speak the language. It's really a remarkable benefit of the program to have these people.

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What do your children enjoy most about this journey?

Mike: The gelato!

I think with education, they like the absence of testing and unnecessary pressure that comes from the US education system.

Socially, they have so many more opportunities to just play with other kids. At home we had to schedule playdates. Here, they run into friends everywhere.

And the traveling. Not only being here, which is one big trip, but also going and doing little weekend trips.

Jessie: My kids really enjoy the Education Center, and it's because the value system is different. Our son, who's seven, came home and he couldn't believe that a field trip was all day. This week they went to Florence on the train and were there all day. It was the most incredible field trip my kids have  ever done.

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How has the Boundless Life community supported your family’s sense of belonging and connection?

Mike: We've noticed that everyone is like-minded. We find ourselves sharing a lot of interests or experiences and also finding similar attitudes and philosophies. And so it's easy to make friends.

There isn't a single person I couldn't ask to go get coffee. I mean, everybody is interested in being friends and being friendly with each other, which is really special and unique, especially coming from a corporate environment where nobody wants to be anybody's friend.

Jessie: I think sometimes travel, particularly to countries where you don't speak the language, can be very lonely. And that is instantly addressed with Boundless. Even just the walk to the hub, you see people that you know having coffee and whether you sit down and you join them or you just wave, you're welcomed in a place that is completely new to you.

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Can you share a special moment when you thought, “This is why we’re doing this”? Any magic memory that stands out?

Jessie: When we were in Syros, Greece for that first cohort, my son had just turned six. Boundless does a great job of encouraging kids to experience local culture – and that includes trying local foods. One day we were sitting in the town square, and out of the blue he announced he wanted spanakopita (the Greek spinach pie). We got him a piece – it was literally the size of his face – and I have this photo of him just chomping into it. In that moment I thought, this is why we’re here.

Mike: For me, there isn’t one big dramatic moment – it’s more a collection of small moments. For example, every morning I walk the kids to school through Pistoia. On the way back, I might run into another parent in the piazza and we’ll end up doing something social with them or doing some spontaneous activity. So to do it every single day, it’s these little moments that I'm incredibly grateful for.

You’re one of the only sibling duos doing Boundless Life. What has it been like to travel and live abroad together as brother and sister (with your families)?

Mike: In Syros I felt we spent a lot of time recounting our childhood, which reinstilled in us why we’re doing this and how we benefited from our travel as children, and now as adults.

Jessie: It's just such a wonderful space to continue that relationship of being siblings. Here in Pistoia,  we live in the same building, there are weekends when we do things together and also weekends where we’re going in different directions. There is just something so undeniably special about meeting my older brother for a glass of wine in the courtyard. We don’t get that living in different cities back home.

Mike: It's been a really special opportunity to travel with a family member. And I think if people were worried about spending too much time with their family member, Boundless is set up in such a way where you don't have to be attached at the hip for three months straight.

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Would you recommend Boundless Life to other families? If so, why?

Mike: I’m an unofficial Boundless brand ambassador! I will have hour-long phone calls with friends explaining exactly how this works and what my experience is like. I love talking about it and advocating for the program.

I think it also goes without saying that people noticed a change in my family after we came home from Greece. I think they're going to notice an even bigger change when we come home from Pistoia. And that really speaks for itself,

Jessie: Absolutely. And I will say the Boundless community tends to grow itself. We’ve made so many new friends within Boundless that now when we plan future cohorts, we’re coordinating with other families we’ve met because we all want to travel together again. If anyone out there is reading this, I encourage them to take the leap and join the Boundless Family. It will change your life.

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