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How “What if We” Turned into Traveling and Working from an RV Across America

Editor’s note: Join the journey of Buffer’s data analyst, Matt, as he and his wife and two dogs travel across America in an RV while working remotely! This is the first post in an ongoing series. And they’re kicking off their voyage today, October 7th! Go, Matt and Jenna! 

On a Friday evening in late October, 2015, my wife, Jenna, and I were back-porch philosophizing over a bottle of Tuscany red blend wine at our home in Boulder, Colorado.

We can’t remember whose idea it was to begin with, but the question we asked ourselves that night was a huge one: “What if we just ‘sold it all’ and travel around the U.S. in an RV working from the road?”

I’d just begun work at Buffer, where we’re a 100% distributed team around the world. Hearing from all the digital nomads on our team had let a genie out of the bottle. And it just wouldn’t go back in.

At 34 and 32, respectively, three years of both being in grad school while also working full time had left us with a life we had worked tremendously hard to have, but perhaps one that we hadn’t taken stock of in a while.

When we finally looked around, it felt as though we were following someone else’s template for our 30s. What if there was a different ideal out there for us?

The next morning over breakfast we had a quick “Were you serious last night?” and “I’m serious if you’re serious” conversation.

We scrapped our weekend plans and spent the next two days intensively researching the idea. Was there a sliver of feasibility?

Not living a deferred life


On paper, Boulder is an idyllic city for us. We’ve been living in the area for about 12 years, and we have family and really close friends here. It’s still kind of hard to pinpoint why we want to leave all that behind.

During my last interview during the hiring process for Buffer, I shared with our Chief Happiness Officer, Caro, that one of the reasons I was so drawn to Buffer was how the values and culture enabled the pursuit of “not living a deferred life.”

She asked what that meant to me, and I froze. As silly as it sounds, I had really only ever internalized the concept by way of what it wasn’t, not by what exactly it was to me.

“I’m still trying to figure that out,” I said with a laugh.

I’ve been thinking more on it lately. As I observe friends, family, and people in my career network, I’ve seen the 80-hour-weeks and startup-exit lottery that have become the norm for many in the startup tech industry.

Having an allconsuming focus of time and energy on work at the expense of other pursuits is too high of an opportunity cost for me.

I want to solve challenging problems and learn new skills, but with a balance for pursuits outside of work. It just so happens that this aligns with the Buffer value, “Live smarter not harder.”

How would it work?

By the end of our weekend of research, we concluded that the idea of totally uprooting our life for the freedom of the road might actually work.

We could sell the house and cars, our extraneous “stuff,” get an RV and work from the road, all while tasting life in different places across the United States.

In theory, our workdays would be pretty normal, just with amazing scenery ?. We would travel to new areas on the weekend so as to not disrupt normal work. In the evenings after we wrap up the day’s work, we could explore.

Our two dogs love adventures and car rides, so they would think this is the best thing ever.

Plus, as winter was closing in around us, the possibility of following 70 degree weather sounded really appealing!

But I’d only just begun work at Buffer and we opted to allow things to evolve slowly.

  • I still needed to settle into my role at Buffer.
  • The best time to sell our house would be late spring, so we weren’t too pressed for time.
  • Jenna, who is also a data analyst, convinced her company to let her work remote! But she is the exception to the rule, so we wanted to think this through thoroughly and be respectful of her team.

Every thought led to another question, another possibility.

A modern day VW camper van spoke to our inner hippiness, but would it meet our growing list of requirements? What would our electrical needs even be?

How are other digital nomads staying connected on the road? The more we learned, the more questions we had.

Are we just romanticizing this idea?

The longer we planned and researched, moments of doubt crept in.

We’ve traveled a bit, but never for more then a week or 2 at a time. We might have jokingly mentioned ideas like this in passing before, but this time was different.

Were we just romanticizing the idea? Why did we feel so compelled to make a drastic life change like this?

I’m still trying to fully articulate the answers to these questions, but I think it has to do with one realization: Life happens whether we are active actors or just in the audience watching it all unfold.

We have a growing awareness of how amazing the world is when you make time to explore it. An awareness of how new experiences and places enable growth in ourselves.


Our house in the suburbs was great, but there were little signs that let us know it maybe wasn’t where we belonged:

  • We’d never bothered to paint over the original sloppy paint job.
  • We never put up photos (in case we eventually did paint, we’d just have to pull them down!)
  • We never bought furniture for the rooms we didn’t use.

We found ourselves questioning our own assumptions about what we wanted in life. Were we really living in a house in the ’burbs just to have space for our stuff?

The process of questioning these foundational aspects of our lifestyle was unnerving, cathartic, and liberating all at the same time.

The reality was that our home base was starting to pull energy and resources away from the adventures we craved; even with avoiding the aesthetic projects, there was an increasing amount of time and resources spent on the general upkeep of the house.

The seduction of a simpler, more flexible, smaller footprint life was growing stronger by the day for both of us.

Don’t get me wrong, we feel incredibly grateful for the lives we have and all the opportunities available to us. We simply wanted to shift our lives to prioritize experiences over possessions to make more space for that gratitude.

Jenna said, “When we started talking about living this lifestyle, I just remember feeling more excited about it than I had anything else in a long time. Planning and the logistics of actually living this lifestyle have been a bit overwhelming at times, but throughout the whole process, it has felt like something we wanted to do rather than something we should do.”

Things are getting real

By March, we started getting more serious about next steps.

Armed with a checklist of logistics to figure out before we hit any point of no return, we started spending most of our free time on project “Van Life” (which would later become “RV Life”, but that’s a whole other blog post).

I had many conversations with my teammates at Buffer, especially the analytics team, about the idea we were considering and how it might work.

I wanted to ensure that if I were to nomad, that I did so in a manner that avoids negatively impacting my contributions or availability to team mates, other Bufferoos, or Buffer as a whole.

Treating it as a work in progress, the data team was excited about the idea. When I shared this idea with Buffer’s founders, they were incredibly supportive:


Jenna was having similar conversations at her job. And as we drew nearer and nearer to the point of no return, we were ready.

We sold our house in June (yeah!!), got rid of a bunch of “stuff,” and moved into a rental in Boulder.

As of right now, the plan is to start roaming at the beginning of Oct. We hope to roll out of town before the first snowfall!

We don’t have a route planned out at this point, but a lot of our “wish list” places to visit are in the Western US.

We’re planning each location out thoroughly, with internet connection being the most important parameter (both cell coverage and signal strength, as well as the nearest backup internet locations like coffee shops)

We are thinking about our first stop right now. We think we might head to Fruita, CO and Moab, UT, then south through the Four Corners into warmer weather in Arizona.

I’m excited to share more of our process and journey in future blog posts. Stay tuned!

Here’s a peek of what’s to come. We call our truck the “Rover” and trailer, “Hab” (based off the bestselling book, The Martian) and over this past Labor Day, we took a first “test” trip near Steamboat Springs, CO.


Coming Up:

  • Meet the Rover and the Hab – Our Test Flight and Launch

Over to You

Have you ever taken a remote trip or gone through a process of cutting down your possessions? Are there things in my story so far that stand out to you? I’d love to hear your questions or thoughts here in the comments!

  • Crystal Bryant

    My husband and I went through a very similar thought process about three years ago — we moved a bit quicker, however, and sold/donated/stored all our stuff and moved to Costa Rica (having never been before) in three months.

    We intended on slow traveling, staying in any given location for 3-4 months before moving in, but we found a little beach town that we fell in love with. We have plans to go to SE Asia once our pups have passed.

    The process of unloading all your “stuff” is so freeing!

    • Jimmy Winskowski

      Crystal- My wife and I have had the same convo about Costa Rica! Would love some advice on making that a reality and things you’ve learned! Mind connecting with me on Twitter? @itsjimmyw

  • Kate Marie Baker

    I would love to see more on convincing your employer (read benefits of) to let you work remotely. My husband and I have been considering cruising. In truth my job could totally be done remotely but it is just not the company norm. Maybe a post on approaching your company?

    • Hey there Kate! This is such a good one! I’ll let Matt share a bit more about this as his wife is the only one in her company that is working remotely. Here is a cool post by our CEO, Joel, on why he chose to have our company remote — some great thoughts in there! :) Thank you so much for reading!

    • Maria Scarpello

      4 hour work-week has some decent tips on how to transition your job to a remote one. Highlights include: try just 1 day a week to start to give the team/employers a chance to see what this is like, slowly add another day or part-time. It can be useful for your employer and the employee alike, remote working, particularly working while full-time traveling isn’t for everyone.

    • Russell

      Give your boss a copy of the book “Remote”

  • Andrew Wade

    Would love to know more about your gear setup and how that you worked through your cellular internet connection needs, power/generator needs, etc. – This is phenomenal! :-)

  • Megan Kelly

    Anxiously waiting to hear more about the adventures! This is the plan for summers, and life after the kids are on their own in 15 yrs!

    • Love that, Megan! :) So excited to watch and share more of Matt’s journey too! :D

  • Oh my gosh, Matt!! Love so much about this, thank you for sharing your story with us! 1) I remember that moment in our interview! I’d say we are all “still figuring that out.” :) So thrilled that you’re taking life by the horns in this way! 2) The Hab. So good. Happy travels my friend!!

  • Izzie Egan

    Living my dream! We drove from Anchorage, up to fair banks and then down to Seattle this year in the RV as I worked, quite literally, my way back home! #Bestlife! Enjoy every min of it!!

  • digikalyna

    My husband and I had a similar “following someone else’s template” moment a while back, so we packed up and moved from Maryland to the Pacific Northwest. We also took this as an opportunity to do a 2-3 week cross-country road trip. It was absolutely amazing to be on the road and seeing all of the beauty the States have to offer! I kept a travel log, and I still look at it to relive the drive. I will be looking forward to more road tripping posts from you – good luck! :)

  • Rich C

    Congratulations on your adventure! I’m sitting here with Marvin Braun from Precision RV. He told me about your recent time together, and I’d love to get to talk to you about what you’re doing.

    I’ve been a full time RV’er for a decade now, working from the road as well. And I set off at the ripe old age of 34 as well. Looking forward to hearing more of your story.

  • Philip Mooney

    I’m only supportive of this is you come visit us in CA! Awesome article and all the best.

  • Clint Schroer

    Awesome you two! Safe travels and look forward to future updates!

  • Matt – What a great adventure. A friend of my mind did this a few years back in an airstream. They crowdsource the best locations to visit in the US. Check it out >
    Good luck and have fun!

  • Bryan Milne

    Well done Matt and Jenna!! I think its a life change and journey that will enrich you more than you can think possible, enjoy it and I look forward to reading the posts. You are an inspiration to the rest of us who long to take Twains advice:

    Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.
    Mark Twain.

  • Maria Scarpello

    Congrats on taking the plunge! My partner and I did the same 6 years ago. Similar to what you’ve discovered, we could not stand the idea of the traditional “this is what you’re supposed to do after you graduate college” life path. Prior to this trip we had visited more countries than States, and with our two dogs, we decided it would be a great way to continue to explore new locations while not having to separate from them for long periods of time. Little did we know how comfortable it can be to bring your bed and closet with you everywhere you go! Especially when you have an affinity for craft beer like we do. ;)

    When we started we thought we would only be on the road for 6 months while we figured out the next place we wanted to live. Was only about a month into the trip that we looked at each other and said: “why would we live somewhere, when we can live everywhere?!”

    So then our story transformed to: “the fun runs out when the funds run out” knowing that our savings could only hold us for so long.

    That’s about the same time that I found WooThemes (now better known as WooCommerce, who was acquired by Automattic in 2015) who also run a fully distributed company and as they say, the rest is history! We’ve successfully found a way to avoid the funds running out and we just keep on truckin! WOO! We feel very fortunate to be where we are today, knowing our life would not be possible without the tech advancements we’ve made in the last 5-10 years.

    If there is one piece of advice I could give it would be this: do your best to not overplan. Some of the most exciting opportunities adopting this lifestyle can be the ability to pick up and go whenever you’d like! The more RV park reservations you make the more difficult it can be to allow happenstance to take over. The first month on the road felt more stressful than it needed to be just because we had no idea what we were doing when we decided to book the first 30 days of parks early. Many of our most memorable times on the road came completely unexpected and we’ve ended up discovering people and places that we never otherwise would have known existed!

    Enjoy your time on the road! Feel free to reach out anytime you have questions or could use advice! @TheRoamingPint

  • Very inspiring story.

    As an editing note, “let her work remote!” should actually be remoteLY :D Enjoy your new life!

  • Brian Ghidinelli

    My girlfriend and I put everything into storage, abandoned our SF apartments and traveled RTW for 7 months in 2006-2007. I echo the sentiment that what you’ll regret most are not the things you do but those you don’t. Now that we have an infant, backpacking is out but I’ve been eyeballing Airstream renovations by for a future live+work extended trip. Don’t feel pressured to hurry, slow travel = happy travel! Have a great time!

  • Diana Kaemingk

    My husband and I did this for 6 months! Good for you!

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