Boat Life as a Family of 5! With Erin Carey, Roam Generation

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How do Erin Carey and her husband balance raising three boys, running a PR firm, and managing a remote team scattered across the globe, all from the deck of a yacht? The family sailing lifestyle isn’t easy, but Erin makes it happen and in this interview she shares her best boat life tips and inspirational stories. 

Other Sailing Interviews To Check Out:
Full-Time Sailing in Your 50s and Beyond, With Sailing Ocean Fox
What is it Like Sailing Around Svalbard in the Arctic?
What Full-Time Sailing as a Couple is REALLY Like! With Ryan and Sophie Sailing 

Jump right into my Awesome Interview Series videos on YouTube here – and please give it a thumbs up, leave comments and subscribe!

Erin Carey shares what boat life is like as a family of 5, while also being the world's only PR firm run remotely from a boat! #boatlife #familysailing #RoamGeneration #sailinglife #familytravel

Meet Erin Carey and her Sailing Family

Erin and her husband weren’t sailors when they came up with the crazy idea of leaving the rat race and sailing away. Without letting that minor detail get in the way, they bought a yacht on the opposite side of the world and went on to cross the Atlantic Ocean a mere 18 months later. 

In this interview we discuss:

  • Leaving behind the security of a traditional life and career for the unknowns of boat life.
  • Balancing a remote business, homeschooling, and the never-ending list of boat maintenance chores.
  • Recognizing an inner knowing that it’s time to change, even if that change isn’t logical or anticipated. 
  • Lifestyle travel is not a life sentence! The beauty of long-term travel and lifestyle design is the ability to redesign and redesign again according to what you want and need in life. 
  • Managing a remote team scattered across the globe.
  • The advantage of working with coaches in all areas of life and business. 
  • The importance of defining roles and responsibilities within the family unit.

Watch (or Read) Our Interview Here! 

Please enjoy our engaging conversation on YouTube by clicking here, or watching below. 


If you’d rather read than watch, below is the transcript of our conversation. 

Nora: Welcome to the show Erin. I’m really excited to chat with you today. 

Erin: Hi Nora. Thank you so much for having me.

Nora: It’s funny. I’ve already had a few people on my show who have the sailing lifestyle. They live and work full-time on boats. I feel like this is a trend that has accelerated pretty dramatically since the pandemic began.

How Erin’s Family Sailing Lifestyle Started

Nora: I feel the two big trends have been van life and yacht life or boat life, as the case may be. But for you guys, you had this full-time sailing lifestyle before the pandemic began. I’d love to start by asking you, “What was that tipping point for you and your husband to launch yourselves into a full-time sailing lifestyle without any prior sailing experience?”

Erin: Would you believe there actually wasn’t a tipping point? It wasn’t something that tipped us over the edge. It wasn’t the straw that broke the camel’s back. We were living a life in the suburbs in kind of middle-level jobs. We had three children. And life on the surface was great. It was fine. Nothing to complain about, probably what you would call living The Australian Dream. Something for me didn’t feel quite right. I knew deep down that I wasn’t spending enough time with my children and that I was worried that I was missing out on the formative years of their life.

However, there was nothing concrete in plan. It was just this feeling that I had, that we would do something big one day. I had no idea what it would be, certainly would never have dreamed that it would be living on a boat. What I probably would have guessed would have been that we might’ve moved to Spain and been expats for 12 months and sent the kids to school or something. That’s what I had in the back of my mind, but it was always something that was going to be down the track. 

You probably wonder, “How did she come to live on a boat?” It’s actually a funny story. Well, not really funny, but what happened to us could happen to anyone because it was a very regular night. We had both finished work, finally got the kids into bed, flopped down on the couch to watch Netflix, which is usually the highlight of our day. And we came across a documentary. Actually, my husband came across a documentary that I wasn’t really intending on watching. I was going to just scroll on my phone, and he put it on. It was a documentary by Laura Dekker, or about Laura Dekker, the youngest girl to ever sail around the world.

We’d never heard of her. Like I said, no intention of watching it, but he started playing it and I just remember kind of being captivated by it and then just putting my phone down and then sitting in silence for the rest of the 90 minutes, or however long it went for. Then, at the end, we just both turned to each other and went, “Wow, that looks cool. We should do that.” How does that even happen? I have no idea. How does it happen to both husband and wife at the same time? What are the chances of that? 

But my husband was on board as much as I was. We moved straight to the computer. We started Googling “families sailing around the world” because, at that stage, we didn’t even think it was possible, let alone safe, because we had three little children. The youngest was about one at the time. We found that it was doable, that there were actually a lot of children and families out there living on boats and sailing the world.

I had no idea whether you could do it on a boat. That’s how naïve we were. I thought maybe you had to be on a ship because I didn’t know if personal watercraft could cross an ocean, but turns out they can. You don’t have to be in the Navy, and all of these weird misconceptions that I had. We kind of kept looking into it, and over probably the next two weeks, we found numerous YouTubers who were doing the same thing. SV Delos, Sailing La Vagabonde. We came across all of those great guys. 

Then we also came across Sailing Totem, who were a family with three children who had sailed around the world and they had started up a coaching company for people exactly like us, to coach people to get out on the water. Literally, within probably two, three weeks of watching that video, we had made the decision that we were going to buy a boat and sail the world. We never said how far, because I still can’t tell you how far we’re going to go. We just knew that we would sail somewhere in the world for– it started off with maybe a year, but then we kind of pushed it out to two years, and now it’s indefinite. Within two years and two months we had sold a stack of our possessions, got two years leave-without-pay from our jobs, and flown out on one-way tickets to Grenada in the Caribbean, where we saw our boat, which we had bought sight unseen, for the very first time, and began our journey. 

Nora: There are so many intersections of your story and mine in what you just said. I lived in Grenada for two years. I had that as a home base. Before I got that home base and Grenada, that was my introduction to yacht life because I got to know some people who own boats, because Grenada is a very popular place for people to weather the winter because it’s just out of the hurricane zone. I met people there. 

Then I, through some connections, started my three months of living on boats in St. Martin. On a boat, on Sophisticated Lady. I believe you know who Rick Moore of Sophisticated Lady is. I was on his boat for a while. 

I was in St. Martin when Laura Dekker pulled in from her circumnavigation. It was a huge event, and it was an amazing environment to be in and experiencing that yacht life in all its glories. It’s really an amazing lifestyle. I only did three months, and I was always on other people’s boats. But certainly, it was a journey and a half, to be sure.

I’m curious. You started off, you got your leaves-of-absence, and you were just dipping your toes in the water, so to speak, of the sailing lifestyle. Was it difficult to learn to sail and to really embrace this new lifestyle initially, especially with young children?

Erin: To be honest, not really. For me, I’ve just felt like it’s been a natural progression. Now look, I’m not the best sailor in the world, and I also don’t really maintain our boat. My husband does all of that. Of course I can help him sail, but he’s the captain. I mean, in our regular marriage I’d say we’re pretty equal, but on the boat, I’m quite happy for him to be captain and to make the final decision, because sometimes I just don’t want that responsibility.

On paper, I probably don’t really suit the boat life. I am a girly girl. I like to have new clothes and go shopping and wear makeup. I’m not particularly sporty and I don’t really love the outdoors or camping, but for some reason I love living on a boat and I have pretty much felt at home on the boat since day one. Don’t get me wrong. There’s definitely been times where you go, “Oh my God, whose idea was it to live on this damn boat? It’s a nightmare. And things are always breaking and going wrong.” But overall, yeah, I really love living on a boat. 

We did a few things to prepare ourselves to come out here. My story kind of makes it sound like we were taking a risk, but everything that we did was very calculated and well researched. We didn’t just go on a whim, “Let’s just go buy a boat and sail away.” We had three kids. Obviously, we wanted to be as safe as possible. So in the two years and two months that we went from making the decision to leaving, we bought a little trailer sailer boat that we would practice on at home out in the bay. 

My dad actually used to be a sail instructor back when I was a kid. He taught us how to sail. He used to do it on little dinghies in an inland lake. Definitely it wasn’t glamorous. Funny story, I used to have to go along with him sometimes when mom needed a break. He’d choose one kid out of us three girls to take and we’d all roll our eyes and go, “Oh, do we have to go, dad?” I hated going. If he had told me back then as a kid that I would grow up to be a sailor and live on a boat, I never would have believed you, but it’s funny how things work out. Now I love living on a boat. My children do sailing. Never would have seen that happening. 

Dad taught us how to sail and we made mistakes. Basically, we played around on this little boat. It was 21 foot. It was big enough for us to all squash into. We were so keen that we’d even sleep on board. It was so cramped, and the toilet was a little port-a-potty, and there was nowhere to cook or anything, but because we were just so happy and excited to be out in the water. We loved it.

We had that for about 18 months, and we learnt quite a lot with that little boat. We also crewed in a sailing club, or yacht club, races. Every Wednesday night we’d attend those. We didn’t do any courses or anything in sailing. We were pretty confident that we’d be able to learn on the job, so to speak. We did do a week-long passage from New South Wales to Queensland, where we paid for the chance to go on this other person’s boat and help him take it up to Queensland. You could argue why he wasn’t paying us, but we were quite happy. That’s how keen we were, quite happy to just get a chance to go on a big yacht because we still were worried that, “What if we put all of this effort and time and money into it and we don’t like it?”

We did that and we absolutely loved it. We were pretty certain that when we got out on the boat that we would love it. And yeah, we did. When we arrived, we knew so little that we weren’t confident cause our boat was up on the haul, which means on stands on land. We weren’t confident when we splashed her to get her from the point where she was splashed out to a mooring buoy, which was probably only 500 meters, but that’s how inexperienced we were. We had to get a newly made friend that we’d met to come on board and help us move her. 

Little by little, we would learn. The first time we went out, we literally went out of the mouth of the bay and did a couple of circles and came back in, and that was a huge achievement. The next time we went round to the next bay and practiced anchoring, and we couldn’t get it, but we tried. The next time we managed to set the anchor and every time we moved, it was slightly further and slightly more successful.

Of course, there were many mistakes as well. We’ve run aground, we’ve dragged. There’s been definite mistakes along the way, but it happens to everyone. What I will say is that my husband is very technically minded and logical and capable. I trust that he has it all under control. Which is nice. 

I don’t think you could do this if your partner wasn’t that way, or you yourself . I’m not technically minded. I’m sure I could learn how to service an engine, but it’s just not something I’ve got a desire in doing. He’s the same. He doesn’t have a desire in running a business, so it works perfectly.

Erin Carey managing a remote career on a boat

Managing a remote career, homeschooling, and boat maintenance

Nora: That’s an excellent point that you bring up. Which is that everyone has to be on board. Yes, pun intended. But also, everyone’s skills are very complimentary. And also, there’s a lot of work involved. I definitely want to dig into the specifics of your career, but right now I’d like to look at the lifestyle element of how you manage a remote business, educating three children– I’m assuming because they’re different ages they all require different curriculums– and also managing the daily tasks of life on a boat, which are practically a full-time job unto themselves. I don’t know if your husband also has a remote job or career as well. How do you do it all? Because that is a lot. 

Erin: It is. And to be honest, my husband doesn’t have a remote career because that would be literally impossible. I’ve heard of some people where both mom and dad work. I don’t know how they would physically do that. We don’t stop. We go all day and we flop in bed at 8:30, 9:00 at night, once the kids are gone down. We haven’t sat down that whole day. Obviously, besides me sitting at my desk.

We haven’t relaxed all day. Look, it’s not that different to living at home. You work hard. The kids need a lot of attention and to be looked after. They’re constantly hungry or constantly bored or constantly want to do something. They’re kids, and that doesn’t really change when you get out on a boat.

Luckily, my husband and I are a good team. He homeschools the kids. I did it the first time around, cause we’ve kind of had two journeys. We’ve had the first two year sabbatical where we cruised the Caribbean, then the coronavirus happened and we went home for 18 months. And now we’re back out here again.

The first time around I did the homeschool and he kind of helped, and it was extremely challenging. That was when we were kind of making up the curriculum ourselves. This time around, we knew that was something we did not want to do. We wanted to be able to open a computer and for them to be told exactly what to do each day and for us to just have to supervise.

In theory, that sounds amazing, but none of them are proactive enough, or diligent enough. They’re all boys. They don’t want to do school. None of them are diligent enough to actually sit and do their school. It’s a challenge. Every day my husband has to monitor three different children who are all being difficult and the little one’s seven.

Learn more about family homeschooling while traveling with The Pattons of Growing Up Without Borders

He’s doing handstands and swinging around the mast and swinging off the side of the boat. He’s, “Come on, come on, do your maths.” Honestly, his school would take about 40 minutes, but it drags out for about at least half of the day, and the other two aren’t a lot better. The oldest one’s 12. He’s getting better, but it’s a lot of work.

My husband would work from probably 8:30 in the morning to about 1:00. Then finally school is over, but by that time, he’s exhausted because he’s also an introvert. For him to have to do that is a big challenge. Then his second job starts, and that’s maintaining the boat.

Honestly, that is enough to be part-time every day, every afternoon. He’s got a job to attend to because things are always broken, as you would know, on the boat. If it wasn’t for him, obviously I wouldn’t be able to run my business. It’s still not a perfect balance because I have the luxury of being in here. My doors are shut. I get to speak to people on Zoom, and I have my contractors that work for me that I get to talk to, on and off during the day. He’s out there stuck with three children and his job is not as fun as mine. Long-term, I don’t know if it’s going to continue to work this way. We’re looking to stop for a little bit and put the kids into school because we feel like we need a break. They need a break. My husband definitely needs a break.

Maybe that will work for a little while, but they’re also at the stage now where they are reminding us daily that they don’t have any friends out here. I don’t know if that’s to do with the coronavirus, but it’s also, previously, what I read even before the coronavirus, is that there are less children living on boats over here in the Mediterranean than there are in the Caribbean.

We had hundreds of children in the Caribbean, and it was like a summer camp. They had an amazing time. They’ll always organize activities, and sleepovers, and they made the best of friends. Out here, during the last eight months, we’ve only really met one or two families the entire time. That was only for about a three-week period.

The children miss other kids. That makes it a lot harder, but we’re going to Italy next. Apparently there are going to be several other boat kids there. We’re kind of crossing our fingers. That’s the way boat life goes. 

It’s not always great. There are different seasons, and we’re in a season now where we’re kind of not having the most amazing time. It’s still great, and I still am very grateful that we’re out here and that we’re living this lifestyle. Unfortunately, you have to take the bad with the good with boat life. You know that the good times will always come back, because it’s just kinda how it works. There’s always highs, there’s always lows. The highs, luckily, always outweigh the lows, but at the moment, we’re in a little bit of a low. 

We’re in Tunisia, which is amazing. The people are lovely. The food is delicious. It’s really cheap here. They’re definitely the good things about it. But then, there’s not really any green space. Nowhere for the kids to play, and the children rarely speak English. There’s definitely challenging elements about it, at the moment.

Nora: I think that is a metaphor for life in general. It’s just, in my experience, when you are traveling long-term or full-time, and/or have a lifestyle of full-time boat life, as an example, all of life’s ups and downs and swings and roundabouts tend to be just turned up a few notches in terms of the level of Technicolor that you experience these things. Everything is just a little bit more dramatic and we feel everything a little bit more intensely when we’re on the road. 

How long their boat life will last

Nora: You made a point earlier that I think was excellent. Towards the beginning of this interview, you said you figured this is probably an indefinite lifestyle, but then you also mentioned, just now, that you’re thinking that you might stop for a while and enrol the kids in school. This is an excellent point that I want to underscore because the long-term and full-time travel lifestyle is not a life sentence. It is something that can be designed to be exactly what you need in any given moment, and redesigned if you need something else in the next moment. That’s the beauty of lifestyle design is to have that flexibility and that ability to change your life and what you’re doing according to what it is that you want to experience or need to experience.

I imagine as your children grow, you may need to iterate and reiterate again. You have that ability and flexibility to look into your magic crystal ball. You did mention earlier that you felt that this would be an indefinite lifestyle. Now, in your heart of hearts, do you think that this might be a full-time thing? As in, “Hey, this is a forever, or at least as long as I can envision forever to be, lifestyle?” Or, in the back of your head, is there some kind of progression that you’re feeling that this is leading you towards in terms of the landscape of your life? 

Erin: I definitely think this is a progression. We settled on that we would do the boat life as long as it was fun. When we went back to Australia, it was a great wake-up call because we went back because our cruising kitty was getting low, so we knew we had to go back to earn more money. Also, it was kind of a turning point. We were ready for a break from the boat. As it would happen, coronavirus happened not long after, and we had no choice. What was meant to be six months turned into 18 months back home. It probably couldn’t have come at a better time because it really was a wake-up call as to what we want out of life.

All of our family are back home. We miss them dearly. The boys’ cousins are there. I do feel sad that they’re not growing up with them. At the same time, in my heart of hearts, deep down, I know that what we’re doing is right for the boys. I feel dreadful that they’re not with their grandparents. But, I believe that this will help them grow into being amazing young men who will do something different with their life. Because of this opportunity. They might not be getting the private-school-level education, but I feel that what they’re getting is going to go further than what they could have got back home.

Yes, I do feel that this is going to continue. I don’t think we will be on the boat forever, but I also don’t think we’ll go back home anytime soon. I don’t think we could go back home after living this way. It would mean to be able to afford to live back in Australia. Because only I work on the boat. We couldn’t afford to live in Australia with one income. It would mean that my husband would go back to work full time. We’d go back to getting a massive mortgage. It would be like we never left. Sometimes I feel like I’ve got to take myself out of the picture and look at the life that we’ve created. We are so fortunate and lucky to be out here.

I know that if we go home, as much as it’s going to be amazing for the first few months, like it was last time, we’re essentially going to go, “What have we done? We’ve thrown away this amazing opportunity because it got a bit hard. Suck it up. We can figure it out. It’ll get better again.” What I do think will happen is I think that we’ll come across an opportunity for something else. I’ve said this all along. I think someone could come up. I feel in my heart, we might get an opportunity to manage a hotel, or we might renovate a property in Italy, or we might buy one of those really cheap properties in Sicily and renovate it, or something. Who knows? We’re going to Sicily next month.

Something will happen. If we can get the kids into school, initially it will look like six months on, six months off the boat. Something like that could work as well. Who knows? That’s the beauty of this lifestyle. It’s exciting to know that we don’t know what life’s gonna look like in six or 12 months.

Nora: I admire your flexibility. So much of what you have said really resonates with me. For me personally, the really amazing things that I’ve done with my life, and these opportunities that have come my way, were never anything I could have anticipated or planned. Some of the craziest things and most amazing experiences I had just happened organically.

The fact that you’re open to, “You know what, something’s going to happen.” In the same way, when you watch that documentary about Laura Dekker, and you and your husband looked at one another and went, “Wow.” And you had that inner knowing that, “This is what we’re going to do.” Even though it’s like, “This doesn’t really make sense, but we’re going to do this.”

I have those moments as well. It’s amazing to know that you can have that. Something will come and face you, and it’ll be like, “Huh. Well, I guess I’m doing that next.” Knowing that and being open to those opportunities. It’s such a gift to be able to have that flexibility and that openness to whatever might come your way. Not only the desire, but the ability to jump on those opportunities as they arise.

The Carey Family of 5 traveling the world 

Benefits of living in a small space

Erin: We’ve made huge sacrifices to get here. While I do appreciate that we’ve been hugely lucky and blessed. We sold our house. We don’t have everything that the Joneses have back in Australia. We’re not really trying to keep up with anyone anymore. We’ve just got our boat and a bit of house money in the bank. A lot of people would probably say that is us going backwards. But for us, it’s set us free. 

Nora: Likewise, when you live in a very small space, or in my case, when I was traveling full-time, everything I owned fit into a bag, it takes consumerism out of the equation. You can’t buy anything because you don’t have any space for it or it has to replace something you already have. You have to really think hard before you buy anything. 

That also inherently makes it a more financially sustainable lifestyle because– I have since returned to my hometown and gotten an apartment and I am a minimalist at heart. I really am. I lived out of a carry-on bag for two years and a checked bag for 10. But now that I have a roof, I have more stuff and I buy things. I keep thinking, “wow, this is really–” As much as I am this minimalist, you just can’t help it. Do you know the saying, I think it’s a Parkinson principle, where your work will expand to fill the amount of time that you allot it? I feel it’s a similar principle with stuff. Your belongings will expand to fit the space that you give it. 

Erin: And as much money as you’ve got as well. 

Erin’s transition to entrepreneurship and Roam Generation 

Nora: Exactly. Speaking of money, I’d love to talk to you about how you earn your living, because you have the amazing moniker of running the only PR agency in the world from a boat. I know that prior to Roam Generation, you worked for the Australian government for 20 years. I’m curious to what extent that career and your experience informed your jump into entrepreneurship and running Roam Generation. 

Erin: I worked for the Australian government, like you said, for almost 20 years. In a way, it was like an anchor, no pun intended, but a bit of an anchor around my neck because it was a safe job, it had great benefits, and I was always too scared to leave it. So I stayed there. Far longer than I wanted to. Now I look back, I think, “God, I could have had two or three different careers in that time.” But it was a good job. It gave me what I needed. It gave me three lots of maternity leaves. I was able to take numerous leave-without-pays to travel the world. I can’t can’t complain.

And I learned the skills, even though at the time I might not have realized, but the skills that have prepared me to run a PR agency. I was working in a communications role, doing a lot of interviewing and writing reports. It’s pretty, pretty transferable to what I do now. Now I run Roam Generation, which is a PR agency for travel, leisure, and luxury brands.

I interview people, and I sometimes write the articles, not so much anymore, but we essentially try and spread the word, get their name out there, and get them as much publicity as we can. In turn, because we work with travel brands, I’m inspiring other people to continue to travel.

That’s really important to me because my passion is travel. I feel so fortunate that I’m literally traveling the world while running a travel related company. This is my dream job, I suppose. But once you get it, you go, “Is this my dream job? Or, maybe I could do something else.”

If I had known that this is what I would have been doing at the age of 17, when I was wracking my brain trying to figure out what could I do with my life, I would have been absolutely stoked to this outcome. Yeah, it is quite incredible that I’ve come up with this and I’ve not yet found anyone else that runs a PR agency from a yacht. I found a couple that run it from an RV, but still, not a yacht. So I’m going to keep climbing that one until I have heard otherwise. 

Nora: Was the jump into entrepreneurship from a fairly steady, stable job scenario challenging? What did you learn along the way? Was there a learning curve for you in making that leap?

Erin: Oh, definitely. I’m still learning to this day, and I’m sure I’ll continue to learn for years to come. If you ask my husband, he will say it was always a natural progression. I always knew that if I had my own job, I would work far harder than I ever would have been a regular job. Don’t get me wrong, of course I was a good worker, a good enough worker, but I wasn’t passionate about my role in the government. I’m passionate, so much so about my job now that sometimes you could say I’m a little bit obsessed. I think you have to be to really become successful because it takes so much time to get it off the ground. It hasn’t been without its challenges. It’s taken many late nights and lots of hard work, and I’m still continuing to grow and constantly learning. 

Working Remotely running a PR Firm Roam Generation

Managing remote staff around the globe

Erin: Staff is just a new thing to me. Managing staff, especially remotely, is different and a challenge. 

Nora: When I was working for someone else, but I had these entrepreneurial aspirations, I remember having this moment, this tipping point, where I was very efficient at my work with my day job, and I would often finish my job early for the day. But instead of being rewarded for my efficiency, and allowed to– if I couldn’t leave the office, I should hope, at least, I could read a book or study, take some professional development courses.

They were like, “No, no, no, no. You have to pretend to be busy.” I’m like, “Oh, I’m going to go get my own job. I’m going to be an entrepreneur, because that way, when my work is done for the day, I’ll do what I want.” The cosmic irony, of course, being that when you’re an entrepreneur, your work is never done for the day. 

I’ve also connected some dots in what you just said regarding late nights and remote staff in that hiring remotely is fabulous, but coordinating a remote staff, especially when it comes to coordinating meetings and stuff, across time zones no less, I feel can be a very challenging thing. How have you managed this? Do you have any advice for someone who’s managing a fully remote staff themselves? 

Erin: It’s certainly doable. I have a team member in Thailand, one in Australia and a few in America. Then I’ve also got clients in Australia, and– actually they are a team, one person’s in Australia, one person is in Tahiti. I think it’s physically impossible for me and my contractor and the Australian and the person in Tahiti to be on a call at the same time. Unless it’s in the middle of the night for one person, so that’s difficult. It usually just means that my contractor doesn’t sit in on the meeting and then I relate to her what she’s missed out on. 

Other than that, it’s just been a lot of using the Time Buddy app on my phone to make sure that I don’t mess up all the time zones, providing calendar links so people can book a time and see it in their time, and then I don’t have to calculate the time difference. Honestly, I haven’t found it that difficult. The thing that I’ve found more challenging is finding quality staff and staff that hang around after you train them all up, then they leave. Or they promise you the world, and then they start and don’t do anything. I’ve had a big challenge finding good people. I’m willing to take the blame for that. Maybe I’ve chosen the wrong people. Maybe I’m not such a great leader yet, to inspire them to do good work. Or maybe I’m just better at my job than I thought, and I’m getting these amazing results and they’re not able to keep up. I don’t know. It’d be nice if it’s the latter. But, yeah, it’s been a challenge.

Advice for aspiring long-term travel families and remote entrepreneurs

Nora: Do you have any advice for someone who is considering a long-term travel lifestyle, plus remote entrepreneurship, plus having a family and homeschooling a family as they travel? It’s a package deal. There’s a lot to take into consideration. How would you advise someone who is considering doing something similar? 

Erin: First of all, I am a huge believer in coaches. We had a coach to get out here. I’ve had a PR coach, I’ve got a business coach. I love coaching. You get so much further than you would if you did it on your own.

Yes, it’s going to cost you money, but you’re going to make that money back so much quicker than if you had to figure it out for yourself. That would be my advice. Number one is get a coach. Get a coach to become a digital nomad. Then get a coach in your business that you decide to set up. 

The second advice is, if you’re going as a family, make sure your partner’s on board, and figure out those roles as best as you can. Once you’re out there, it’s fluid and you might figure out better ways along the way. Knowing that it’s probably going to be challenging for both of you to work at the one time. Because, what are the kids going to do? You don’t want them to be on iPads all day long and you’re both working. What’s the point of being out there traveling if that’s the case. That’s probably my other bit of advice.

Thirdly, I think it’s all about mindset. If you believe you can do it, you will. If you believe you can’t do it, you won’t. I always looked at it like failure wasn’t an option. That’s one of my qualities, I suppose, is I’m persistent and tenacious and flexible. You do have to be flexible. You have to be able to not let this lifestyle get you down. Because it will. There are going to be times when it’s so challenging that you absolutely question everything and wonder why you’ve done this to yourself. 

Why did you sell your house and leave all of your friends and family to live on the other side of the world? And then the toilet breaks. And the Apple laptop breaks. And you’ve got no means of buying a new computer. There are just so many things that can go wrong, and they will go wrong. You have to be really honest with yourself. If that’s going to be too much for you, then maybe you have to look at something a bit different. Start with local travel in your country first, or in your state, and see how that goes. 

I think we’re both pretty able to roll with the punches, I suppose. Laugh at ourselves when things go wrong. “If you don’t laugh, you’ll cry” type of things. So that would be my advice. 

Nora: I think it’s excellent advice because I think that rolling with the punches and being able to laugh at yourself, being able to appreciate the levity of the situation, at least with some retrospect, if not in the moment. I often say that travels’ misadventures make for the best stories with a dose of hindsight. Truly, the ability to roll with the punches is the only way to get through that and to understand that it’s not always roses and lollipops. There will be challenges along the way. This is kind of life stuff as well. If you can see the challenges as development opportunities, you’re going to come out better in the end. But also, not to throw in the towel when the going gets tough. Because it will get tough on the road. It is inherently a little more challenging. Those challenges, they can be great opportunities as well to discover new things about ourselves and the people that we’re with. 

Erin: Exactly. And the highs always outweigh the lows. I’ve found that to be true the entire time. Fellow boaters say the same thing. There are so many lows, but the highs still always outweigh them. So it’s worth it in the end. 

Nora: I think that’s a good metric to use. If and when such a time comes where the highs don’t outweigh the lows, then it’s time to reevaluate and reiterate. There are many ways to do that in lifestyle design. 

Family Sailing Lifestyle with the Carey Family

Final words

Nora: Erin, where, and how can people find you and connect with you?

Erin: You’ll find my business at Roam Generation.com, and the same handle on Instagram, Facebook, Twitter, and LinkedIn. Roam Generation, and it’s R-O-A-M. Roam happens to be the name of our boat. That’s what I named my business after. I love the word “roam”. It means a lot to me. It also has a story behind it, because it was the theme song that played on the kon-tiki bus of our very first overseas trip. Every morning they’d blast the “Roam if you want to” by the B-52s over the speaker. We were usually hung over, and so tired, and had a thumping headache, but the tour guide would just blast it full bore, and somehow you’d spark up and enjoy the day. So that’s where you can find me for my business, which is a PR agency, like I mentioned.

If you’re just interested in our story, that’s called Sailing To Roam. Sailing T-O R-O-A-M. Again, Facebook and Instagram. There, I just tell stories about what’s going on in boat life and all the trials and tribulations. I say it as it is, and tell it as it is, because I’m not going to be posting these fake Instagram photos. It’s really not like that out here. People that do, from my experience, I don’t possibly see how it could be as glamorous as what they’re portraying it to be. But, hey, they don’t have kids, maybe. Maybe everything’s just amazing if you don’t have kids. That’s where you can find me there.

Nora: Excellent. I appreciate anybody who can keep it real because I think that you were doing more of a service to the people who are following you by showing the real deal: good, bad, and otherwise, then you would be by posting those Instagram-perfect shots. I appreciate that. Thank you. I will definitely provide links to all of your handles in the show notes and descriptions. Anyone who’s interested in clicking a link to connect with Erin, please do so. Erin, thank you so much for joining me today. 

Erin: Thank you so much. 

Nora: I’m Nora Dunn. I’m otherwise known as The Professional Hobo, and I will catch you next time.

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