Couple Money

Planning and Taking Cross Country Road Trip

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Like many couples, travel had been on Derek and Carrie's mind for a long time. However, they were busy with their work and raising their daughter.

Thankfully, Olsens personal and professional circumstances had shifted and an opportunity came up that would let them follow their dreams.

Want to Take Cross Country Road Trip Together?

How many times have you guys thought about traveling? Not just a weekend getaway or a vacation, but really seeing another place? What's stopping you? 

These last few years with the pandemic have been..well, alot. We’ve had lockdowns, restrictions, and having to adjust work for the norm. On top of that, if you have kids, school looked completely different. 

While we’re understandably cautious and keeping an eye on things, I believe many of us are also hoping not just to travel like before but want to try something different. 

That Trip Advisor survey I mentioned last week about travel trends highlighted that more people wanted to explore different locations. It was less about visiting tourist traps and more about embracing their destination’s uniqueness.

That’s why I’d think you enjoyed my interview with Derek and Carrie Olsen. Years ago, they, along with their then toddler, took a cross-country trip with their trusty travel trailer. 

Even now, it’s one of my favorite interviews. They’re a sweet couple but they also had some fantastic tips and thoughts on how to simplify things and have a true family adventure. 

So whether you’re thinking about taking an epic trip or pivoting in your career or life, I think you’ll enjoy this chat. 

In this episode, we get into: 

I hope you enjoy!

Resources to Have a Memorable and Affordable Trip

 Here are some resources to check out:

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Derek and Carrie's Epic Cross Country Road Trip

Elle Martinez: Like many couples, travel had been on Derek and Carrie's minds for a long time. However, they were really busy with work and raising their daughter together. Unlike many couples though, the Olsen's personal and professional circumstances had shifted.

Derek had started building a business and along with Carrie, they launched the podcast better conversations on money and marriage.

Carrie also had transitioned into voiceover work. With these changes, the opportunity to travel opened up as an idea, began to take shape once Derek caught the family adventure podcast,

Derek Olsen: I was inspired by a different podcast remember? So there's another podcast called Family Adventure Podcast and I just kind of stumbled upon.

That's where the idea really came from. But the reason why it's hard to answer that question is that Carrie and I have kind of both had this similar ideas in the past. And so it's actually kind of hard to pinpoint whose idea was it?

Carrie Olsen: Doing this whole family travel thing was something that I would've wanted to do, you know, even before we got married and into marriage, but I would never have mentioned it to Derek because I thought he would have been like, we're not going to do that.

So when he came up with it and was like, let's do this thing, I was like, yes. Yeah, he's the one who brought it up.

Book Tour Road Trip

Elle Martinez: Their trip was tied into a book they had written together One Bed, One Bank Account, which as you can probably guess, discusses how couples can work together and talk about their finances.

Since this was a huge undertaking, it took Derek and Carrie some time to work through the process.

Derek Olsen: It was a gradual thing. Like I don't remember… cause cause man it's been, it's been at least a year and a half now, since the initial, I mean, it's been almost two years, I think since we first started talking about, but the conversation was really gradual.

Like I kinda mentioned it and then we listened to the podcast a little bit more, and then we kind of we'd talk about it every now and since. So it was really a gradual thing. In fact, from the very first time that I brought it up till the time that we actually went, was it 10 months? Is that right? So it was a really gradual conversations.

As the conversation moved forward every week or every month, it became more real because you know, an idea of, Hey, let's sell everything we own and buy a travel trailer and travel around the United States for seven months. That takes a little bit, you don't just go. Okay.

Carrie Olsen: Well, and for me, I remember when Derek first brought it up, you know how, when your spouse brings something up that they quote unquote think is their idea, but you always wanted it anyway.

And so you have to, you have to. Ease your way into it. You can't get too excited at front because you don't want them to be like you don't want to put them off. So when he mentioned it, I was kind of like, oh yeah, well, that's interesting, you know? And then like the more he'd bring it up and it was doing, and I was like, oh my gosh.

Oh my gosh. And then it, you know, just built the more that, you know, he thought about it. And, and then I was in shock because I was like, oh my gosh, I think he's really serious.

Elle Martinez: If they were going to travel and make it work, they had to keep things light, which meant simplifying their lives in one huge step involved, paring down, no purging, most of their stuff.

Derek Olsen: I mean, we sold or donated, or just got rid of, I mean, like 75% of everything that we owned. So that process was huge, but it was a lot of work. But it went fairly, it's fairly straight forward. Like, you know, just put a bunch of stuff up on for sale on Craigslist. Or we did like a salvation army pickup where they just picked up a whole bunch of our stuff.

And then we had to buy the travel trailer and move into it and all that kind of stuff. So that, that sort of pre-trip preparation was fairly straightforward. Even though there was a lot of work

Elle Martinez: while we haven't had to downsize as much as Derek and Carrie, we did unload furniture, kitchen gear, and of course closed before a big move.

I agree with Derek that the process is straightforward, but it can seem overwhelming when you first start. My advice is to focus on one room at a time after you get things boxed up and ready to go. It's now the fun part selling and donating your stuff. Besides selling through Craigslist, there are other options to make sure you're getting the most cash or credit, depending on what you're unloading.

These sites might be the best place for your stuff right up. Are you looking for an easy way to get rid of a lot of your clothes, throw it up, makes it simple. You make a request for a bag. They send it to you and you fill it up. They'll examine your clothes and they can either ship them back to you or donate the ones that they can't.

Vinted you can use the smartphone app to sell your clothes, snap, some pictures, be savvy about how you describe it, and you can find the right buyer. And finally Amazon, believe it or not, you can sell some of your used stuff on Amazon, like books and DVDs. Donating is a great way to help others and get stuff out of your house.

You can call your local chapter of your favorite charities and see if they do pick up. There are also services like college hunks hauling junk. Yes. That's the name which can help you move. Get rid of junk and pick up for donations. And with less stuff and junk in your house, you can free up your time and finances for whatever adventure you want to take.

Simplifying their possessions, help the Olsen's to downsize their living to about 133 square feet. But even with all their preparation, Derek and Carrie had some unexpected hiccups on the

Derek Olsen: road, I will tell you that once we hit the road, like we had several things. That happened that were, that were unexpected.

It's, it's really hard to describe to somebody what it's like to live on the road full time and to not have a house and to have very few possessions and to live in a, such a small space on the road. It's almost impossible to describe what that's going to be like until you experience it. And so really a.

Not every step of the way, but often once a week or once a month, when we were on the road, we'd have something happen that we were not prepared for, that we were not expecting. And so like, I mean, just a really quick example on the very, very first day that we left to go on our epic road trip, our car broke down the very first day.

It was like, it was like, we went from. Being on cloud nine, you know, we're like going down the highway, this is the first day we're unbelievably excited,

Carrie Olsen: you know, Tom cruise on Jerry Maguire and the scene, but this job. Exactly.

Derek Olsen: Yeah, it was amazing. And then, and it went from that to being really one of the worst days because our car got our car bumped down.

We had to get towed and I thought that. I thought that, that like our engine had exploded or something and we were just totally screwed, but it turned out to just be a water pump. And so it was a fairly easy repair. And then, and then our car was fine the rest of the time, but it was just really scary to go through that on the very first day, such a, what I thought at the time was like a disaster.

I was, Derek was destroyed. I was a wreck like, like for me, And we had a few things like that happen where, because I felt like I was I and not to say that, well, let me just say it. And then I'll kind of clean it up. I felt really responsible for the safety of our family. It's I mean, that's. Dangerous things due to pull a travel trailer behind our truck.

And I was very safety conscious. And so for something like that to happen on the highway, it's real, it's really dangerous. And, and again, that's what I'm, that's not to say that Carrie is not, you know, worried about our safety and all that, but I'm, I'm the worrier that's for sure.

Elle Martinez: The two of them had a fantastic time on the road and picked up some great lessons for the next trip.

They'll take. Sometime in the future.

Derek Olsen: We thought that, you know, I thought like me and five months we had originally planned to go seven and we only went for five. I thought, man, that's a long time, you know, five months is a long time. Surely we can drive around the entire United States in five months.

It sounds doable. It sounds doable, I guess, but once you get out there, we realized that that's actually really, really fast, really fast.

Carrie Olsen: Well, especially when you're carting around a one year old with

Derek Olsen: a one-year-old so we kind of mapped it out to where we're spending one week and in every big city.

And that to me again, sounded pretty good. Like you, you get phoenix and you're there for a whole week. You go to LA and you're there for a whole week and then you're in San Francisco for a whole week. It sounded pretty good.

But honestly, if we ever did it again, I would spend a minimum of two weeks and probably a whole month in each city or at least in each region, because picking up and moving every single week with.

Was it felt fast. Yeah. It felt really, really fast. Like the whole thing almost feels like a blur because it was so fast. So man, that's definitely, that's probably the number one. If I only had to change one thing. Yeah. That'd be it. Like if we just did change that alone, that'd be enough.

Carrie Olsen: I think it depends on your purpose too. Cause if you're just wanting to see every city, then that would be fine. But we were trying to work and we had the baby and everything. Something I would do different. Was, it would be take less stuff. We ended up dumping off attempt a ton of stuff after we got on the road.

Luckily Derek's parents were on the route that we were going, so we just stopped by their house and just dropped off a bunch of stuff. We brought way too much stuff.

Elle Martinez: Even with setbacks and technical difficulties, Derek and Carrie are happy that they made this leap together.

Derek Olsen: The biggest thing that I took away from this, and I'll be interested, I think Carrie agrees, but we'll get curious, answer on this.

The biggest thing that I really took away with it take away from it was this idea that like, I can't believe we did that. What else are we capable of doing?

Like, when we look forward into the future, The fact that we traveled, sold everything. We owned, bought a travel trailer and traveled the United States for five months. It makes everything else that, you know, every other opportunity that comes our way, it's like, yeah, let's do that.

You want to do something crazy? You know, this other crazy thing. Yes. It makes me more likely to say yes to things that seem big and scary as a result of this. I kind of surprised myself and I'm surprised at what. I'm capable of doing,

Carrie Olsen: I was excited to do it for the adventure of it. You know, I think for me, I was just, I was excited that it was something new and big and different and, you know, didn't know what it was going to be like, but definitely after having done it feels.

You know, most other decisions that we're going to make are smaller in comparison to, Hey, do you want to sell everything that we own and go travel around the country for five months.

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This episode was originally released February 2016. Shownotes and episode were updated May 2022.

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