How to Roam the World While Roadschooling Your Kids (Megan Tenney’s Story)

This post is brought to you by a few of Megan’s travel essentials: a Kindle, a tiny WD hard drive for backing up important documents, and a set of pickleball paddles and balls.

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!

Megan has an inspirational story on ditching the rat race that’s supposed to make us happy. When her family decided to move across the country, they had a lightbulb moment; living in Airbnbs anywhere in the world was often comparable (or cheaper) than their previous mortgage.

Megan works remotely from anywhere, and her kids are roadschooled, gaining a whole new perspective on what can be a classroom.

Thank you for being here with Freedom Is Everything, Megan!

Table of Contents

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

Hey there! I’m Megan, and my family of six has been traveling full-time for over two and a half years. My husband Daniel and I have traveled to 45 of the 50 United States on our journey so far, along with our four kids. When we started traveling, our kids were 10, 7, 5, and 1 — now they are 12, 10, 7, and 4!

Our travel journey started with a plan to travel the US for one school year, as we moved from the west coast to the east coast, but we enjoyed it so much that we decided to extend our travels and go overseas. We booked flights to London and secured an Airbnb in the heart of the city…for April 2020. Needless to say, all of that got canceled thanks to the pandemic! 

Since we couldn’t travel internationally, we continued to nomad through the US while we waited things out, and now we are hoping to rebook for the fall of 2021 and start our international adventures. In the meantime, we’ve had the opportunity to explore almost every state and corner of the USA, and we’re absolutely loving it!

I work remotely full-time as communications manager for a digital advertising company, and Daniel teaches part-time online while also homeschooling our four kids. We like to use the term “roadschooling” because we combine our traditional schooling curriculum with real-world exploration, learning about the unique cultural, historical, and geographical aspects of each location we visit.

Megan Tenney
Devil’s Bridge – Sedona, AZ

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

Two and a half years ago, we were living the usual rat race of constant activities and commitments. We were filling our lives with things that, in theory, we were passionate about — but were just making us miserable. We knew we needed to make a change. 

One night I confided that I missed living by the beach on the east coast, so we decided to uproot and make the cross-country move, but Daniel suggested taking our time to get there. 

He said, “Why don’t we just sell our house and stay in Airbnbs as we travel?” 

I scoffed at the idea, thinking that’s just not something people do, but then I did some research. It turned out to be a great idea! The cost of living in an Airbnb for a month was similar to our mortgage payment, so it was completely do-able.

The key phrase in what I just shared is “not something people do.” It was hard to make such a major change to our lives and to start living in a way that was completely against the norm. But it’s when you give up the familiar that you discover the extraordinary.

Hot Air Balloon Fiesta – Albuquerque, New Mexico

Yes, I was disappointed that my five-year-old was going to miss out on his first day of Kindergarten and that whole experience. Instead, he dug for clams in the Pacific Northwest that year, took a sandcastle-building lesson on an island in southern Texas, hiked part of the Appalachian Trail, and played on playgrounds in Central Park in New York City, visited Mount Rushmore, and so much more. He also learned to read and finished his Kindergarten year at a second-grade level.

National Zoo – Washington, DC.

I was definitely stuck in a one-track way of thinking, but there’s no reason to just automatically do what everybody else does. When you can break free of that mindset, you realize how much it was holding you back. Because we changed our lifestyle and took an unorthodox path, our kids are now all several grades ahead in school, we make and save far more money than we ever did, and we’re visiting all of the places on our travel bucket list!

Please tell us your detailed story of how you got into your line of work and how you turned it into a remote career.

I started blogging way back in 2008 when I was nine months pregnant with my first baby. I had an education degree and teaching certificate, but I wasn’t teaching at the time. I was working part-time for my dad’s small software company, doing bookkeeping and other administrative tasks. The blog was a fun way to feed my creative side.

I blogged very casually for several years before I discovered the whole blogging community and started to take it a little more seriously. I began to run digital ads and write sponsored content. Soon I was making a low five-figure income from my site — not enough to live off but a decent side hustle. 

Wigwam Motel on Route 66 – Holbrook, Arizona

Once we started traveling and we were both working part-time, Daniel was always on the lookout for remote job postings. One day, a few months into our travels, he came to me with a listing saying, “I’ll apply for this if you want, but they are looking for you!”

The listing was for a digital ad management company that worked with bloggers to run the ads on their sites, and they were looking for someone to join their remote communications team — a strong writer who knew the digital content industry. My many years of blogging and soaking up all the information I could about online content creation had prepared me perfectly. I applied and got the job! As I mentioned before, this allowed us to be fully financially secure, and two years later, I continue to work for the same company and love what I do.

What does a day in your work life look like? Paint a picture for us :).

My job is very traditional in some ways and unique in others. I work 8 am–5 pm Monday through Friday, but I work remotely, which means I can do my job from anywhere with an internet connection. Our life is pretty similar to anyone else’s — we just happen to be in a new location every month or so!

My workday is a combination of writing projects (often working collaboratively, in Google Docs), virtual meetings on Zoom to discuss and plan projects, and scheduling these projects and assigning tasks to team members in our project management software. I write a lot of articles and coordinate information across a lot of different teams within our company.

While I work, the kids do their morning routine and start school. They use a lot of online resources, like Khan Academy, as well as reading novels and completing physical workbooks. We also incorporate extracurriculars and life skills — at various times, their school schedule has included things like running, chess, meditation, computer programming, and piano, alongside reading, math, history, and science.

Market Common – Myrtle Beach, South Carolina

Daniel teaches online in the mornings and then helps kids with their schooling. He does most of the grocery shopping, meal planning, and cooking, too! We have meals together as a family and do chores around the house. 

In the evenings and on weekends, we take time to explore the destination we’re currently visiting. We try to hit the touristy “must-dos” (the Space Needle in Seattle, Times Square in NYC), as well as local hidden gems (a kite flying festival on Whidbey Island, the Fourth of July parade in Ocean Park, Maine), and any educational or cultural opportunities (touring the Alamo in San Antonio, hiking the Appalachian Trail in West Virginia).

Kite Festival – Whidbey Island, Washington

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

We love to explore new places, and we also love to revisit our favorites! 

I grew up in Maine, and the beaches of southern Maine are my happy place. We love to visit there in the summer and take the kids to the beach, amusement parks, and our favorite restaurants.

New York City is another favorite because there’s just so much to do there. We stayed in a tiny apartment in Brooklyn, a five-minute walk from the nearest subway station, which had us in midtown Manhattan in 30 minutes. We played at the nearby splash pad, visited Times Square and Central Park, explored the 9/11 museum and memorial, went to the beach at Coney Island, and saw lots of Broadway shows. Since we were there for a full month, we were able to enter the lotteries for cheap Broadway tickets every day, and we went whenever we won.

Pebble Beach – Brooklyn, New York

We also loved our time in Dauphin Island, Alabama — the complete opposite of New York City! Daniel recently called it “the best-kept secret in America.” It’s a very sleepy beach town in the winter, and our Airbnb had bikes and kayaks, so we spent our time biking all over the island and kayaking on the bay right across the street from our house.

Pelican Point – Dauphin Island, Alabama

We are excited to take our travels overseas. But the cool thing about traveling the US is that there is such an incredible variety of climates and cultures you can experience, all by car — the tropics of southern Florida, the plains of the midwest, the Rocky Mountains, the misty Northwest, the picturesque Southwestern deserts, the big cities of New York, Chicago, and Los Angeles, and everything in between!

Grand Prismatic Spring – Yellowstone National Park, Wyoming

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

First, DO IT! If seeing the world is your dream, make it happen. And don’t wait. I know it’s kind of a cliché to say “YOLO,” but it’s so very true. You have one life, and it’s a gift, and you are the only person who gets to choose what to do with it.

If you’re thinking of traveling with a family, still DO IT! There’s no comparison to the experience and real-world education kids get from seeing the world. And if you spend time on traditional learning, they can speed through their lessons because of the 1-on-1 attention they’d never get in a regular school.

Sandcastle-building lesson – South Padre Island, Texas

Our biggest challenge was letting go of life as we knew it and pursuing an alternate path, but once we took the leap, we never looked back. And you don’t have to commit to a different lifestyle forever. Maybe try it out for a few months and give yourself a safety net to return home if you want. You’ll probably realize you didn’t need it!

I like to explain it this way — nearly everybody has sold one house and bought another. And even if it’s just for 10 minutes, you’re temporarily between houses. Why not just extend the time between selling (or renting) one house and moving into another? You can stop traveling and settle down whenever you want. If you get the chance to take the trip, DO IT.

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

Many digital nomads are single adults or married couples, but traveling with kids adds a whole level of complexity! You have to consider schooling, kid-friendly activities and destinations, the prospect of taking them away from friends, and their extracurriculars… Not to mention the need for extra clothes, supplies, food, and space!

A lot of people assume we travel in an RV, and plenty of families do, but not us. We travel in our minivan and stay primarily in Airbnbs. This gives us the flexibility to travel just about anywhere and have plenty of living space while we’re there. We usually stay in one location for four weeks at a time, so we aren’t constantly on the move. This provides our kids with a level of stability while still getting to explore lots of places, and we get to experience each location to the fullest!

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?

Before we started traveling, it seemed like we were always on the cusp of being able to save money. We’d finally pay down our debt and start to save, and then we’d have a new major expense. Our family of six is very frugal, and we had to be because we were living on a teacher’s salary and a part-time salary.

When we started traveling, and both of us were only working part-time, we were just able to afford it. We made enough from selling our house that we were able to start our travels debt-free, but with no savings.

If you’re willing to sell your house and give up that safety net of a home base, then you can take the money you would have spent on your rent or mortgage and utilities and put that toward your lodgings while traveling. Depending on the size of your travel group, your comfort level, and how much you were paying for your housing prior to traveling, you might even be able to save money while traveling full-time!

We kept browsing remote job listings and, a few months into our travels, I accepted a full-time position with a fantastic company and started making more than we had prior to traveling. This made a big difference — all of a sudden, we were able to easily afford our lifestyle and save a significant amount of money each month. The trade-off was a little bit of freedom — now, I was tied down for 40 hours a week. But I love my job, I enjoy working, Daniel does a great job handling kids and homeschooling, and it’s a situation that really works for all of us.

For someone interested in getting into your field of work, what’s the best advice that you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

You can really take one of two routes, and I have experience with both. If you prefer stability and don’t mind answering to a boss, look for a remote job with a tech company. Lean on your strengths — if you’re a people person or a good writer, look for something in customer service or communications. If you have tech skills, apply for a tech support or software engineering job. Brush up your Linkedin profile, reach out to contacts for referrals, and browse the online remote job listings. 

Even if your chosen career field doesn’t translate well to a remote position, consider taking what’s available just while you travel and returning to your original career if and when you settle down again!

The other route is to run your own online business — whether that’s a blog, digital shop, freelancing, or consultant work. This takes a LOT more time and effort to get things up and running, but if you can make it work, it gives you ultimate flexibility.

My advice for someone thinking of becoming a digital nomad would be, first, try to secure a great remote job. Even if you plan to fund your travels with your own online business, that might take a while to get rolling. Plus, we really like the fact that our traveling is not tied up with our work. We get to choose where we go, where we stay, and we aren’t beholden to any kind of sponsorships or have to churn out content in order to pay our bills. Our blog and course are a great side hustle, but we don’t rely on them for our primary income.

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

My first blog that I started back in 2008 focuses on the “mom life” — sharing advice on topics such as kids’ activities, at-home workouts, self-care, and now homeschooling. In 2020, after we had been traveling full-time for over a year, I started my new site, Family Gap Year Guide, to share our travel stories and teach other families how they can take life on the road and travel full-time!

Along with this new site, I put together a comprehensive course that teaches everything you need to know to travel full-time as a family — from budgeting to booking Airbnbs, what to bring, how to plan your route, roadschooling, and remote work resources, and all the little details!

Here are some of my favorite posts and resources that I think will be useful and interesting for anyone considering the digital nomad life:

How to budget for a family gap year

The Ultimate Guide to Roadschooling

Our family gap year itinerary

The perfect road trip map to drive across the United States

How to afford full-time family travel (a free guide)

Family Gap Year Guide course

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

Work hard, have fun, and be kind — that’s probably my philosophy in a nutshell. I’d also implore people to listen, learn, and forgive. Our world is very volatile right now, but if we all took a breather and sat down together with open hearts and minds, I truly believe that we’d all agree on a whole lot more than we realize. 

What digital tools do you use for your work?

I’m on Slack all day long! We also use Google Drive, WordPress, Google Analytics, CoSchedule, Zendesk, Zoom, and more. In addition, for my own websites, I use Meet Edgar, Later, Teachable (to host my Family Gap Year Guide course!), Flodesk, and Ubersuggest, among others.

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

I’m always reassessing what we travel with and swapping items out anytime we visit family or our storage unit. We’ve been lucky enough to travel with our minivan, which has plenty of space, but we try to pack light. When we go overseas, we plan to have just one backpack each.

My husband and I each have an REI Ruckpack 40, and we love these because they can transform from a backpack to a duffle bag when you zip up the straps. Perfect for using as a carry-on and then wearing on your back in between locations.

We also use packing cubes to help keep our clothes organized. For the kids, we got color-coded packing cubes from EZpacking.com.

The most important items to pack are clothes and screens. We try to stick to 5–8 full outfits each, plus pajamas and a jacket. Screens are important because it’s how we do work and school and a lot of our entertainment!

I love to travel with a Kindle because I can read as many books as I want on the one device. But you can downsize even more and use your phone or laptop for reading.

My tiny WD hard drive is great for backing up all of our important documents, photos, and videos. And another must-have are notebooks and pens — as digital as my life is, I still like to write down my daily to-do list!

Having four kids means we travel with some extra items, like toys. Our older kids have mostly outgrown toys and prefer to use screens, but we don’t want them to just be on screens all day. We travel with just a few toys and trade them out fairly often to keep them from getting bored. Sometimes the Airbnbs we book have kids’ toys, and that’s always a fun surprise. Another option is to visit a thrift store as soon as you get to a location, get some new-to-them toys that will excite them for a while, and then re-donate them when you head to your next destination.

We also travel with a set of pickleball paddles and balls because my husband and I like to play. And at various times, we’ve traveled with a wooden train set, basketball, volleyball, bocce ball set, jump ropes, roller skates, musical instruments, a crockpot, various board games, and a VR headset!

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

One of my favorite books is “Happier” by Tal Ben-Shahar. He teaches that to be happiest, we should spend our time pursuing both things that bring us pleasure in the present and those that will benefit us in the future, with a focus on our values.

So, for example, I work at a job that I find fulfilling and also brings my family the income we need to survive and be comfortable. When I’m not working, I lean into having fun! Spending a Saturday at the beach or going out for a nice dinner with my husband means I’m enjoying the present and not postponing joy for some future date.

Conch Café – Surfside Beach, South Carolina

And that brings me to another major philosophy of mine, which is to savor each moment. Especially as our kids grow, I enjoy remembering the past, and I truly love to plan for the future, but I also actively try to stay in the present and breathe in every moment I have with my family in every destination we visit.

How can people learn more about you and your work?

You can read all about our travel adventures on our website, Family Gap Year Guide. Our course teaches everything you need to know about how to travel full-time with a family. And we’d love to connect on Instagram, @familygapyearguide, where we share pics and stories about our most recent travels!