7 Years of Epic Full-Time Family Travel (Celeste Orr’s Story)

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This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Celeste is a treasure trove of insights on how to nomad with a family. She’s full of incredible stories about adventures she’s been on and has a delightful outlook on life and work as a digital nomad. She’s the essence of what we’re all about here at Freedom Is Everything.

We’re so thankful to have you here, Celeste!

Table of Contents

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

Growing up in small-town Georgia in the 90’s, the idea of traveling full-time while working remotely and starting my own business never even crossed my mind. When I had my first child in my 20’s, also in small-town Georgia, I was in love with travel, desperately wanted to work remotely and be a stay-at-home mom, but didn’t see a way. 

Everything changed one day when a little thought dropped into my mind: WHAT IF THERE’S MORE? Three months later, my husband and I had sold everything we owned (which wasn’t much), and we were moving across the world to live in Sydney, Australia. A year and a half after that, we moved back to the US with two babies in tow. And five years later, we had sold everything again to buy an RV and travel the US full-time. Now, seven years on, I’ve traveled to 49 out of 50 states in the US with my little family, and we have big dreams of living internationally again in the years to come.

The number one question I get when I tell my story is, “How did you pay for it?” My answer is simple: I gave my best to the work in front of me (teaching, nannying, nonprofit management, community development, database consulting, writing) and kept pushing for opportunities to do it remotely with more flexibility, more time-freedom, and on my own terms. It was difficult at first, but now, I own my own consulting business and publish books and resources to help other parents who want to live life their way at togethernessredefined.com, and I’ve never been happier or more fulfilled in my life. 

I’m so glad I listened to that little question, “WHAT IF THERE’S MORE?” If you’re thinking of traveling more with your family, I hope you’ll listen to it, too.

Celeste Orr's family with their airstream

What inspired you to start nomading? And how has nomading changed your perspective on life?

The travel bug bit me in 1998 when I went to Jamaica with my youth group. It was my first time traveling internationally, and I knew I didn’t want it to be my last. When I married my high school sweetheart in 2004, we easily agreed we wanted to travel more than just the normal yearly trip to the beach. So by the time we felt the tug to move overseas in 2007, we were more than ready.

If travel has taught me anything, it’s that experiencing new people, places, and parts of the world has the potential to profoundly change us. Encountering new cultures opens our minds. Living outside of what we’ve always known has the potential to help us become our biggest, brightest, best selves. Thanks to my travels, I now have a very different worldview from the one I was raised with, and I’m proud of that. I hope I never stop learning, growing, changing, and traveling.

Please tell us the detailed story of how you started your business. 

I haven’t always dreamed of owning my own business, but I have always dreamed of working from anywhere in the world. My degrees are in sociology and public administration. My talents are in the realm of writing, reading, and helping people learn – not software development – so a path to entrepreneurship and a location-independent career wasn’t clear to me at first.

But when my employer let me know that the only way I could work 100% remotely was to become an independent contractor, that’s what I did. I gave up my health insurance, salary, and 9-5 schedule, and embraced the life of an independent, hourly-paid contractor. There were only small parts of my job I could do remotely, though, so my pay was significantly decreased. Two years later, things had changed. I had proven myself valuable and was able to do more remotely than they thought, and I was tired of not being able to afford good health insurance. So, I let go of my business, and the company employed me full-time 99% remotely. 

Three years later, I was back to my original feeling of not being able to make peace with the “on call 9-5” kind of life (and I needed to spend time on my writing too), so I politely asked if I could go back to working for them as an independent contractor – for good this time. And I started my own business – a real one this time – to encompass my current work (nonprofit database management) and my passion work, too (helping families go after their dreams). 

Celeste Orr profile

As I write this, I’ve now grown my client base and am not only able to contribute work I feel good about to worthy organizations, but I’m also spending time pursuing the career I hope to pursue for the rest of my days – writing, speaking, and photography. (And I’m well on my way to doubling my income, too.)

I’ve learned that becoming a digital nomad, doing work we love with the location-independence and time-freedom of our dreams is not always a linear path. There are starts and stops, and that’s okay. What matters is that it’s possible for anyone who wants it, no matter their background, gender, color, or creed – and that we keep it that way.

What advice would you give to someone who’s thinking about nomading?

Try it – that’s my first piece of advice for anyone who’s thinking about nomading. Whether it’s for a few weeks, a year, or long-term, the only way to know whether or not it’s for you is to try it.

My next piece of advice comes in categories:

Friends: When we started traveling full-time, several family members made it clear they were concerned that we would be lonely and would lose touch with our friends back home. Pretty quickly, though, we found the opposite to be true. Not only have we met some of our best friends while traveling, but we’re also meeting new ones every week. It’s been a different reality from suburban life – in a very good way.

Marriage/Family: I don’t know where we got the idea that good marriage and family life means working 9-5, dropping the kids off at school, cooking dinner, and then going to bed and doing it all over again the next day. I’ve never felt comfortable in that kind of marriage and family life. When you can work (and school) from anywhere in the world, though, everything changes.

Anything is possible – blueberry crepes on Wednesday mornings, cuddle breaks after lunch, hiking the best trails while the rest of the world is in their cubicle – anything. It’s the kind of marriage and family life I love.

Celeste Orr family

Career/Work: I’ll never forget that time a lady saw me cleaning campground bathrooms with my husband while our small kids played nearby in the woods and said, “Tell me about your family. Do you live here?” and then, “But what about your career?!” I can laugh about it now because since that moment, I’ve more than doubled my consulting income, and I only clean campground bathrooms when I want to, but at the time, it bothered me more than I let on. What that lady didn’t know is that sometimes we have to let go of our ambitions to find our true creativity – the one that’s going to make us the most fulfilled and help us contribute the most to this world (and the one that’s going to bring the most money to our family for more adventures).

I’ll never regret giving up my safe salary job to travel the world and build my own business – it’s what has led me to my best work.

Education: I’ll let the homeschool debate wage elsewhere, except to say that world-schooling our children was the best decision we ever made for their education. And I know so many other families who feel the same way. I can’t wait to see where all of these out-of-the-box kiddos take their love of learning from here!

Adventure: What is life without adventure, really? I don’t know, and I hope I never do. If you feel the pull towards traveling more, I say try it. Live a life of adventure – you’ll make mistakes, and you may have regrets, but at least you will have lived.

Celeste Orr adventuring

What is unique about the way you travel, and what advice do you have for someone that wants to travel with a similar style?

I travel with my family and “SLOW” is what we like to call our travel style. During our seven years of full-time RV travel, we spent a total of 25 months (5 months at a time) at the same campground in Maine. Seeing all of our traveling friends crisscross the country every summer, we were tempted to follow suit. But something told us that fast travel during the winter, and slow travel (or as some would call it, no travel) in the summer was our jam.

We actually did try giving fast travel a try one summer and after finding ourselves tired, broke, miserable, and way too hot, we knew it wasn’t for us. So back to summers in Maine, we went.

That being said, we weren’t quite as “SLOW” travelers as the sailing community, though. In the winter of 2019, we tried living on a catamaran and quickly discovered that wasn’t exactly our cup of tea. (The ocean was nice, but boat maintenance all day every day? No thank you.)

Now we take things very slow. We’ve bought a house near Acadia National Park and have parked our Airstream there to share with friends for the next few years so we can be ready to take family trips overseas in the years to come. We’ve got Sydney, London, Dublin, Johannesburg, Christchurch, Paris, Athens, Rome, and Copenhagen on the top of our list. But we know seeing them all may take us more a few years. We’re okay with that.

What are the 2-3 favorite places where you’ve lived/traveled to and why?

Living in Sydney, Australia, was a dream come true. Visiting the national parks of Utah, Wyoming, and Montana was a dream come true, too. But Acadia National Park on the coast of Maine captivated us when we first visited in 2015 and still has our hearts today. We loved the ocean, the sweet little hiking trails, the gorgeous mountains, and the salty Mainers (and other New Englanders) we met. So, we returned to spend the full summer season there five out of the six summers we spent traveling full-time and ended up setting up a home base there this year.

(I share photos of Acadia every week on Instagram and in my email group, too.)

What is one of your favorite travel stories/experiences?

Thor Razorblade is the star of one of our favorite travel stories. 

We were boondocking out West and decided on a whim that we might like to experience the Mojave Desert. So, after what seemed like hours of driving down washboard dirt roads with our Airstream, we arrived at the campground and quickly found quirky crews on campsites all around. So we struck up a conversation with a couple of guys who were gushing over our Airstream, quickly letting them know the feeling was mutual as we gushed over their VW campervan. That’s when Thor Razorblade arrived on the scene.

“Yeah, this is my dream van,” the guy said, “I have big dreams of taking my girl and our son around the country in this baby one day. His name is gonna be Thor Razorblade, and he’s gonna be the coolest little guy on the planet – no offense to yours, of course.”

Coolest. Name. Ever. And those are the coolest kinds of dads ever, too, if you ask me – the ones who can’t wait to take their kids on adventures.

My family still cracks up when someone mentions the name Thor Razorblade. I hope we run into that kid in a campground one day.

Since launching, what has been most effective to acquire/retain customers and scale your business?

Investing in my own professional development and personal growth has been, by far, the most effective growth strategy for my business. Nonfiction books have been continually on my nightstand and in my earbuds for as long as I can remember, but two other growth experiences gave me a huge jumpstart for starting and growing my business.

First, I enrolled in a master’s program – a dream of mine for over 14 years. It was online from the university where I got my undergrad and exactly where I knew I should be for growing in my area. While in that program, though, I discovered that what I thought was my career path (nonprofit development and management) wasn’t actually what I loved doing most. But I finished the program anyway and learned a lot about developing my professional skills. (And I got three valuable letters behind my name, too.)

Then, I enrolled in Marie Forleo’s B-school and Copy Cure, where I learned the how-to for building a sustainable, thriving business through relationship marketing, email groups, and great writing. And I go through the modules every year to improve my skills and grow my online presence so customers can find my products and services. Without this program, I wouldn’t have had the skills and confidence to build a thriving business.

Now, I help other women find their own path to personal growth and development so they can go after their dreams (and grow their businesses if they want), too. It’s work that has changed my life, and I can’t wait to see how it changes theirs.

What digital tools do you use for your work/business?

I’m not sure this article could hold the full list of digital tools I use for my business, but here are my favorites:

  • Evernote for daily task tracking, productivity-enhancing, and badass project management that makes clients come knocking at my door
  • Slack for organizing tasks and communication with a team of people
  • SquareSpace for upgraded website building and sales (I used WordPress and Elementor for my first website building attempts but quickly found them outdated compared to SquareSpace)
  • MailChimp for managing my audience and email group (any email tool will probably do, but having an email list and communicating regularly is a MUST for growth)
  • MeetEdgar for increasing my social media presence and making it more intentional and professional (and for posting regularly for me when I want to be off the grid)
  • And Macs – actually, all the Apple products I can get my hands on because they truly do make living the creative life faster and easier (and prettier)

Celeste Orr working on signing books

As a woman, what should other women who haven’t traveled much know about traveling/nomading?

As a married woman, I entered travel with the mindset that it was something I would never feel comfortable doing alone. All these years later, after seeing numerous women rocking solo travel, I’m inspired. I took several business trips alone but always found myself hiding in my hotel room after dark, not willing to go out alone. Last year, though, I took my kids tent camping in the Katahdin wilderness in Maine all by myself for the first time. It was frightening at first (especially when we got lost on the way there), but I knew it was something I had to do for myself. The whole experience was liberating. Now I know I can travel alone if/when I need/want to. I think that’s something every woman should know.

If you had debt/student loans when you started nomading, how did you handle or think about this, and what advice would you give to other people with a similar situation?

I haven’t been debt-free since I was 18 years old. Some people will find that troubling, but I don’t. When we started nomading full-time in 2013, we had an opportunity to buy an older rig and vehicle and reduce our debt, but we didn’t take it. Because we wanted our rig to be our family home for the next five years or more, we bought a brand-new camper. Then, six months later, we traded it for an even newer Airstream. We haven’t regretted it. (Especially now that we’re able to rent out our Airstream while we save for international travels.)

I also went back to graduate school while traveling and took out student loans to pay my tuition. They’ll be paid off in a couple of years, but it was a great investment in my eyes.

I say if you have an expertise or skill and you’re willing to work while you travel, you shouldn’t skimp on your accommodations. And if you have the desire to gain a college education and are determined to pay it off quickly, don’t skimp on that either. Get yourself an abundance mindset, go for it, and don’t look back.

Celeste Orr hiking with her sons

What scale is your business at today, and what are your future goals?

When we first started traveling full-time in 2013, cutting expenses to require less income and earning that lower income through work-camping and small consulting contracts was our funding strategy. An unsafe work-camping experience in South Texas in 2015, however, forced us to reconsider. We call that negative experience a huge blessing in disguise. As it turns out, temporary, low-paying jobs weren’t fulfilling for us, and low-budget travel wasn’t our cup of tea. 

So, we turned to a varied funding strategy, instead – with one of us taking on database consulting work that could be done from anywhere at any time (me) and the other building construction, landscaping, electrical, and plumbing skills that could be used in-person anywhere we wanted to be (my husband).

Today, my consulting business earns twice as much income as I earned in my traditional job before we started traveling (sometimes more – again, thanks to professional development and personal growth), and my husband’s skills have not only allowed us the opportunity to live where we most want to be, but they’ve also enabled us to create our own rental property business. In the next five years, we should have earned enough income to travel internationally for fun 2-3 months out of every year. Then, in the next 10 years, we hope to be pursuing our passion work more and traveling internationally as often as we desire.

For someone interested in becoming an entrepreneur in your field, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

DO THE MINDSET WORK is the very best advice I have for someone in the social sciences field wanting to travel full-time. It sounds cliché, but I cannot tell you how important that one piece of advice truly is. When we truly believe anything is possible, we can set about making it happen. 

The very best learning resource for achieving this, in my opinion, is the Marie Forleo podcast, email group, and book. I can’t even count how many thought leaders, books, resources, and kick-ass concepts she’s connected me to over the past few years. Her growth mindset is contagious. Get on that email list today – it’ll change the course of your life.

What is your philosophy on being happy and/or finding meaning/purpose in life? And any recommended resources for people navigating this journey?

Few things make me sadder than chatting with someone close to the end of his or her life who feels they haven’t really lived. For the rest of us who likely have plenty of days ahead of us here on Earth, we still have a chance to really live our lives – to use our time “to the hilt,” as Eleanor Roosevelt would say. I don’t know any better way to do that than to show up as our biggest, best, highest, truest selves for the people we love the most – our family and friends. To do what makes us most alive. And to do it with people who love us. Even if we have to redefine togetherness to do it. That’s what finding meaning in life is about to me.

I write books and work with people one-on-one through email courses to help. If I can help anyone take steps to making that happen for themselves, I’d be honored. Here’s where you can learn more about my most recent book: https://www.togethernessredefined.com/book and my email courses and one-to-one programs: https://www.togethernessredefined.com/programs

Tell us about your content creation journey and share some of your favorite content that people should check out!

I started my very first blog in 2009 and gave up within three months. It was crap, and I knew it. What I didn’t know back then is that everyone starts out with crap. I started my second blog in 2014 to share our travels. It was crap, too, but people read it anyway because they were interested in where we were going. Now, I run an online platform at togethernessredefined.com for adventurous parents, and not only am I making it better every day, but it’s my path to book deals and speaking gigs that will enable me to speak hope into millions of people’s dreams. We all start small and crappy – all of us. Only the ones who stop trying stay there.

You may be interested in my “Traveling More” series there: 

Or, you can see my full media portfolio at celesteorr.com

Orr family photo in front of their airstream

What small change has made a big difference in your life?

The small change that has made the biggest change in my life is getting serious about my personal growth. Period. Full stop. I would not be doing what I’m doing had I not done that.

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

Kids need their parents to truly live – and to do it with them. That’s the most important thing I’ve learned – the thing I will share with people until my very last breath. Kids don’t need parents who sacrifice everything they love. They need to see their parents doing what they love and including them in it, truly living and loving every single day. Full stop. The end. That’s what this thing is all about.

What do you travel with that you couldn’t imagine traveling without?

Comfy hiking boots or shoes, an insulated, plastic-free water bottle, and a good, sturdy hiking pack are three things I’ll have on all of my travels. There’s no way I can travel without them – except for that one time I did, which is probably why I’m so passionate about those pieces of gear now. I won’t bore you with the whole story, except to say that even if you think you’re just flying somewhere for one simple meeting and flying home the next day, you might find yourself stuck in a beautiful spot like Washington, DC, and you’re going to need some good walking shoes and a reliable pack and water bottle.

To see my family using some of our favorite products, join me on Instagram @togetherness_redefined

What’s your favorite book and why?

Honestly, my favorite book changes with the week because I read a lot of books. Right now, I’m into books that are pushing me to grow, like Jen Sincero’s Badass series, Marie Forleo’s Everything is Figureoutable, Luvvie Jones’ Professional Troublemaker, and Michelle Obama’s Becoming. I’m also listening to a few books that are pushing me to learn more about the race issues in our country, like Jodi Piccoult’s Small Great Things and Angie Thomas’s The Hate U Give. In the last year, I was blown away by a few novels – Ann Patchett’s State of Wonder, Susan Meissner’s Secrets of a Charmed Life, and Jodi Piccoult’s The Storyteller. But if I had to choose a couple of books to take with me for a desert island situation, it would have to be Elizabeth Gilbert’s Big Magic and Eat Pray Love

So yes, my answer to that favorite book question is complicated.

Tell us about a deep passion of yours! What has your journey been like, and what advice/resources would you recommend for someone interested in learning more about this topic?

Social justice has been one of my deepest passions for as long as I can remember. Channeling that passion into books, articles, and research projects has become one of my highest honors. (I especially love it when my blogs about race issues, human traffickingworld-schooling, and redefining family life cause multiple people to unsubscribe from my email group or unfollow me on Instagram because I know my words have hit a nerve – the first step to true social change.)

Orr family in Acadia at sunset

How can people learn more about you and your work?

Togethernessredefined.com is the very best place to find me and my work. (You can join my email group there and shoot me a message – I love happy email.) Creators and organization leaders may also be interested in my portfolio at celesteorr.com. And if you’re a social media lover, you can find me on Instagram @togetherness_redefined.

Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.