How one couple is working location independently and living their dream

Bryan and Jess are millennials living their dream of working location independently and enjoying the great outdoors during their off time.  They sold their home in Seattle and they work from their favorite outdoor locations around the U.S.  Bryan and Jess have a beautiful Airstream that you’ll get to see as part of this article. John and I just finished living and I worked from the road for two and a half months.  

Transcript of the interview

Today I have two special friends I want to introduce you too – meet Bryan and Jess. My name is Sherold Barr, and I’m trained as a master life coach and have been an entrepreneur in two separate businesses since 1998.

My husband, John and I met you both last year at Malibu RV in California – one of our favorite RV sites, as well as the one that we’re in right now, which is Rancho Sedona in Arizona.

One of the coolest things I’ve found from being on the road and doing my work location independent is the people that I get to meet. It’s interesting to listen to stories of how people are doing this and it’s always wonderful to compare stories and learn from each other.

So, I want to have Bryan talk first and then we’re going to have Jess talk about her business because both of you do your work from wherever you happen to be camping.

Sherold: So Bryan, can you tell us how did you decide to sell your house in Seattle and live on the road? You work for Microsoft, how did that come about?

Bryan: So I guess taking the first part of that question about selling the house and deciding to do this little crazy endeavor in the first place. I felt kind of stressed and overworked shall we say.

Maybe I wasn’t working correctly because I was putting in a lot of hours and certainly coming home grumpy. I guess I wanted to make a drastic change, and for some reason that I’ve yet to figure out what was the actual source of this because I decided, ‘Hey maybe it would be a great idea to go sell or house and trouble around a bit.’

I guess it sort of grew from the fact that we always went out on the weekends. And it was feeling like, hey, maybe it would be easier if we were just living on the road. We can go see more stuff. That’s sort of the genesis I proposed to Jess that we sell the house and buy an RV.

Jess: So I wasn’t on board with it at all.  I thought you were losing your mind! I probably was because you wanted to sell the house and live in an RV, which is not something I had thought of doing. I can’t remember how he convinced me. I started to get on board. I don’t know if maybe we were looking on Instagram at the RV lifestyle or what.

Eventually, after looking into it long enough, I was convinced. I guess we can do this after seeing how other people can make it work in their lives. You don’t need a big house.

Bryan: I think everyone has this concept that you need a house, I need my room, I need my kitchen, I need my separate room, I need all these things. But in reality, when you really look into it and reduce everything down to a subset, it’s just a different way of life that we’ve never thought about before and it was just something that we weren’t familiar with a different way of living.

Sherold: Freedom is a value that a lot of people have and obviously you have it. My husband John and I have it. And this really gives you the ultimate freedom where you’re gonna park or where you’re gonna stay.

Bryan: I think maybe we felt a little tied down by the house as well, because every chance we got, we’d always go out and hike and do trips on the road. I felt like why are we spending so much money on paying the mortgage and being in this house when we’re not really enjoying it? We enjoy camping or being on the road, right? And then when we were home, there was lots of stuff to do.

Sherold: So how do you do it? Do you move and stay two weeks at a time or a month?

Bryan: We try to avoid moving on a week day because I might have a random meeting that comes up, and I need to go do that meeting. We try to move on Sundays. It just gives up the most flexibility and it’s a least amount of stress in ensuring that we get to where we need to go in time to hook up and get ready for the month. We try to stay at places for stretches of one week or two weeks or for exceptional locations like Sedona — we’re saying for four weeks.

Sherold: Do you book places a year in advance?

Jess: We’ve already booked this place for December. Some places let you book a year out and others allow six months in advance. It just depends on the campground that you’re going to in.

Bryan: It’s frustrating though, because when you think of this lifestyle, and you think it’s all spontaneous —  I can just turn from here, there right now, you think of a spontaneous camping lifestyle, which is not really the reality of our being these days.  Especially if you want to go to popular RV spots.

If you want a really amazing spot – like one example is this campground, in Santa Cruz that’s called New Brighton State Beach, there’s two spots that overlook the water and the reality is only one is really nice, and that one, you have the book second, it’s available six months in advance. There’s a bunch of other people competing at the same time, to get that.

So we’re literally on two separate computers. And there’s someone else out there doing that as well. It’s incredibly popular. We’re putting together our plans for next winter already.

Sherold: So let’s talk about a boondocking and what that is.

Bryan: There’s two terms — boondocking and dry camping. Dry camping is typically referred to as camping in a formal established campground without any types of utility, so there’s no water, no power, and no sewage.

And then boondocking is a similar concept but instead of an established campground, you’re sort of at a either national forest property or just out in the middle nowhere. You drive up, you find a good spot that no one else is in, then you park your rig.

Sherold: Do you have a generator?

Bryan: Yes, so we actually initially went out without a generator.  But we use a lot of power.  So now we have one plus we have six 100 watt solar panels on the roof. We have a 600-Ah of Lithium batteries and a 3000- watt inverter.  We think that’s enough.

We use a lot of power. We have two freaking copiers. I have a MacBook Pro. We use a microwave to cook. Occasionally, we use so much power that we feel quickly found that we do need to generator. In the winter months, the sun doesn’t get really high in the sky, and generally it can be quite dark in the winter, so in the winter, you’re not gonna get much a solar power.

Sherold: So you were working at Microsoft. When did you have this idea to be location independent and how did you make it work for you?

Bryan: So it took a little while, and it took about a full year for the idea to sort of percolate through management. Then a re-org happened, and I landed a new manager. The new manager was very open to the idea especially given my performance history. This was a new way of working, and in terms of retention – it’s a new way of working to keep that retention.

Microsoft has invested a lot in it’s employees. So if you’re good, they wanna keep you. And they were open to it as a pilot program because I’m a Program Manager. I work effectively as the voice of the customer. I’m not a developer so I’m not sitting down and computer coding or testing something.

I’m literally putting together presentations, I’m working with customers, and I’m working with developers. So it’s a very people-centric job and for that sort of job, and working remotely is a new thing. I think that so far, I’m doing well.  I’ve gotten two promotions since I started.  I’m very happy that I have a very supportive team that trusts me. You trust them, and they trust you because there’s so much technology and many ways to be remote with work.

Sherold: Jess, I want to talk to you about your business because it’s interesting that you’re both doing your own thing. So can you tell us about that?

Jess: So 10 years ago, I discovered these dolls online. These are called Blyth dolls. And what I do is knit these sweaters and make doll clothes. I sell the clothes online. I used to have an Etsy shop. Now I have my own website called, which I built with Square Space.

I sell the clothes online, that’s what I do. All I really need is a post office wherever I go to ship what I sell. I’ve been in this hobby for about 10 years.


I didn’t really start selling the quite seriously until a few years ago. It’s been about 10 years, and I’ve slowly built up a following of friends online and on Instagram.

It’s a really fun way to make a living and it’s a great creative outlet. I take my dolls wherever I go when I’m hiking so I can photograph them.  It’s a fun photography outlet for us as well. We really enjoy photography and that’s, I think, our main hobby —  what we love to do.

Sherold: So you can do it wherever you are and you have your whole stock pile up here. We’ll take a tour with Bryan. After this video, you can watch a tour of their Airstream by Bryan.

Jess: I would say that we’re all living the dream. I say that all the time — we get to live in all of these beautiful places.  One of the things that I’ve noticed is that I’m much more present whether I’m with friends or with Bryan.

Bryan: That’s right. Because I’m not attending to things in the house — there’s always something that’s vying for attention. You gotta go fix this or your mow your yard. And so there’s something about just being present, being in nature, I think that’s very healing absolutely.

Sherold: How has it affected your performance? You’ve gotten to promotions, but how do you feel… because you’re so tied in to technology. So tell us about what it’s like for you, what you do and do you go out every day on your mountain bikes or hike?

I’m a people manager so I lead a technology area.  I also have a couple of guys that are working for me as well. So being a manager is an interesting change. It allows me to define my role a little bit more than if I were an individual contributor.

It allows me to define what the team needs to focus on doing. So I try to be a little bit more flexible with my guys. Obviously, I let them be a little bit more flexible in defining their own areas and this is your role, this is exactly what you need to be doing.

I try to keep my schedule a little bit more open — that’s done through my schedule. Obviously, I have to book times for meetings.  I try to carve out some time for us to go out, and I try to intersperse it throughout the week, rather than just do it on the weekends. It allows both of us to refresh.

Obviously, there’s days where you’re literally back to back on. You can’t avoid that. And sometimes you have to do that or sometimes crunch time, but it’s always really nice just to be there, be present in our location, but also have the flexibility to just go out when you need to.

And sometimes what we do is, I put telecommunication equipment in my car as well, so I do my meetings out there.

Rather than being here [in the Airstream] on my iPad, my laptop, I just go outside or in the car and do my meeting. Then you’ve got headphones, if you’re on the phones on all day.

Jess: I’ve just discovered the world of podcasts so now I have shows to listen to while I work.  Or sometimes I just put on a show on, if we have enough bandwidth show on Hulu or something while I work.

Sherold: Thank you so much for sharing how you live and work location independently with us.  Now I’d love to have you give us a tour of your Airstream. We’re gonna put some information down below.

What would you tell somebody if they’re fantasizing about living and working this way? What would somebody need to do in terms of research?

Bryan: So a lot of companies today do have a more flexible work options while some companies are closing up a little bit more.

So I do know for instance, Facebook is very much everybody needs to be on the campus. Everybody must be there four days a week, that sort of thing. Whereas other companies are opening up a little bit more, especially smaller companies.

Companies are sort of taking different directions in the industry, the companies have all sorts of different needs as well so Facebook might might be different than other companies and some teams within a company may have different needs then another company.

So I would just understand if your company is open, that sort of thing. If your team is fine or if your management is open to it.

Sherold: And you’ve worked for Microsoft for five years before you made this move to living on the road.  So you had a track record with Microsoft. So it’s good to know that companies are opening up a little bit more because I do think that people can be more productive.

Bryan: So I’ve seen a major shift in the way that our team works. We would basically be 100 percent face-to-face. And just in the past three years, we’ve so many meetings on Skype [now called Teams]. I’d say more than half the people in our meetings would be on Teams. We work with people all around the company that are not physically located in the same building.

We have a lot of collaboration with different people across different locations. And that’s happened just in the past few years and that’s been a major shift, and the technology has really opened that up.

The more technology advances, the easier it is to do this.

I wanna thank you guys who watched our interview. And thanks to you both. We’ll see next year in another location.

Did you like this article?  Do you live or travel and work from the road?  Let me know in the comments below.  Please share this article with others who would find it interesting. 

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