Season 1, Episode 3

How we afford to travel so much

“Travel is the most mind-expanding thing you can do.” – Phil, #SomebodyFeedPhil

Want more travel adventures in your life? We sure did and continue to want more! This has been a major driver for why we manage our money. Since the start of our relationship in 2012, we’ve made it to Costa Rica, Ireland, Scotland, Bali (2x), Thailand, Puerto Rico, Canada, China, and 16 states.

2019 has been the closest to “the dream” we set our sights on years ago. In January, we said goodbye to the cold and to our work schedules to have a 6 week adventure in Southeast Asia. This is where Lindsey had this moment: 

Here’s our behind-the-scenes itinerary for Thailand + Bali – including our itemized costs, things we did, and vetted Airbnb list.

After a few weeks back in Vermont, we set off again for another month on the Gulf Coast of Florida in a 186 sq. ft. tiny house, coming back just in time for spring to kick in.

In this episode, we:

  • share a couple favorite memories of our recent journey & how much it cost us
  • give you tips for making travel a bigger piece of your lives (including how to afford it)
  • share why we put this value front and center in our budget

Our biggest tip for travel couples: talk about your individual travel styles and size of budget! 

Questions we asked each other:

What’s a favorite memory from our last trip?

What was something you learned?

What was a money success on our trip?

Why is travel so important to you?

How would you say we afford to travel?

What budgeting tips do we have?


Lindsey:                 This year has been very different for us, right?

Colin:                       Yeah. Very different.

Lindsey:                 We have spent the first part of 2019 traveling and that’s what today’s show is all about. We spent about a month and a half in Thailand and Bali and we’re going to be talking about the love of travel. I know whenever we do workshops and ask how many people love to travel, the whole room raises their hands. So I know this is a relatable topic.

Colin:                       People always want to know how do you get there right? Sometimes it feels very far away, and certainly if you have traveled, it’s a way to spend money really fast. So yeah, when you see all those glamorous Instagram photos and you see people having these epic once in a lifetime adventures, we thought it might be nice to peel back the layer and just be genuine about some of the grind and the work that goes into making it happen and why we do it. And why it’s worth it.

Lindsey:                 Yeah. I’m trying to remember when our first international trip was. It was in Costa Rica. It was very early (in our relationship). For both of us, we’ve always really loved traveling. So that was a value that we brought to our relationship and knew that we had to work in somehow in our lives. So we have been to Bali twice, to Thailand, Puerto Rico, Costa Rica, a bunch of places in the US.

Colin:                       We’ve done major road trips all over the US.

Lindsey:                 Yeah. And then most recently we were in Sarasota, Florida, living in a tiny house less than 200 square feet. So that was an experiment.

Colin:                       We are up for adventure.

Lindsey:                 Yeah, I would say so.

Colin:                       It’s pretty cool when you think about Costa Rica, our first trip, just sort of testing each other out for compatibility.

Lindsey:                 One hundred percent. And I mean this is probably kind of lame to share, but I’m going to share it because we’re being honest. I do think we tracked all of our expenses on that trip.

Colin:                       We were like, “oh, you like travel and you like budgeting? We have some common ground.”

Lindsey:                 So Colin, when you think about our last trip, our international trip. What’s a favorite memory?

Colin:                       Okay, so we spent two and a half week, two weeks, something like that in Thailand. We spent two and a half weeks in Bali. We spent one day in Beijing. Boy, I mean there’s like probably 10 favorite memories that I have, but I have to say that one of the best ones comes up for me is we flew from Bangkok to a little town called Chiang Mai. And from there there was another town further north called Pai. And the road to Pai was 730 curves and you get motion sickness. So we were like, you know what, let’s treat ourselves and fly to Pai. We were there standing on the runway. Beautiful. It feels very remote. “Let’s GPS where our Airbnb is.” And that’s when it slowly dawned on us that we had flown to a different city and we were both just sort of like…

Lindsey:                 Where are we?

Colin:                       Google flights said “Pai or nearby airports” and we totally missed it. So we end up there and we’re in this place. It feels very remote. There’s very little English being spoken and we had to rent scooters and drive the remaining 110 kilometers. 60 miles. And we did it. Yeah, I remember this little Thai lady with a knit cap and we sort of muddled through some terrible English and Thai. Barely could communicate. She gave us a map and was like, “Here’s Mae Hong Son, here’s Pai. This is what you gotta do. You gotta go through the jungle.” And her confidence in us… I borrowed that because we drove through valley, mountains, windy passes before we ended up where we were trying to go. And that turned out to be this unexpected road trip and adventure that we got to have.

Lindsey:                 I will never forget that.

Colin:                       Yeah. Landing in the wrong airport.

Lindsey:                 And that scooter trip was one of our best memories.

Colin:                       What was a favorite moment for you from our international trip?

Lindsey:                 I felt like we packed in a culminating memory of Beijing, which is going to the Great Wall of China in one day. That was just so unexpected that we were able to make that happen. And the cable car we took up to the top, Michelle Obama had taken, which was pretty special. I loved that. You know, a longer memory would be that when I was in Bali the first time back in 2011, I taught at a youth center and I met this amazing woman, her name is Saras. Hi Saras if you’re listening. She was I think 12 at the time and spoke pretty good English but was learning it. Anyway, we got to see her on this last trip and she’s an adult now.

Colin:                       She’s a rock star.

Lindsey:                 She’s a rock star. And it was just so fun to see someone from that time in my life, when I was by myself first time in Bali. First solo trip. A lot of transition in my life. And to see her now it’s just, I can’t even put it in words. It was so meaningful to me. When we hugged it was so special. I could gush about that all day long. What do you think you learned or took away?

Colin:                       We flew directly to Bangkok. Neither of us had ever been there. It’s a huge, really overwhelming, really hard to describe city. It’s fun, it’s intense, it’s a lot of things. And we got there at 3AM, got a taxi to where we were staying and then we were there in this accommodation in the middle of the city in the darkness. I thought, “We’re not going to know how to navigate this or work this out. And within a couple of days we were moving on to Chiang Mai and I remember I had all these tips and guides saved on how to talk to a street vendor and how to navigate public transportation, what to tip a cabdriver, what scams to avoid. And after three or four days when we left, I was able to delete all those files. I thought, “What a visual for all of the learning that we did in a really short amount of time by putting ourselves somewhat outside our comfort zone. So that’s something I’m really proud of. I feel more confident because of that experience.

Lindsey:                 And we’d joke that we might be on a subway or a train and what do I immediately do?

Colin:                       You take a nap.

Lindsey:                 Yeah. I take a nap because I know you’ll figure it out and you’re not mad at me about that. Those are our roles.

Colin:                       Together those roles complete you as a little little nucleus, little traveling organism. One of you is gonna look out for one thing, one looks out for the other. When I travel I’m always trying to find the line between overthinking it and underthinking it. You really helped me find that line because together I think we feel more confident that we’ll figure it out. You have a confidence that really helps me find the balance.

Lindsey:                 So Colin you already travel quite a bit for your business. How does this fit with that? Can you share a little bit how you make this work for your, for your business?

Colin:                       It’s funny. The answer goes kind of way back to years ago where I found in some of my full-time jobs that I didn’t have the flexibility to travel. I made a long range goal that if part of running my own business and working for myself means that I don’t have to ask somebody for permission to take time off, then that seems like a pretty good reason to look into it. And that freedom has proven to be one of the biggest reasons I love being an entrepreneur. What about for you?

Lindsey:                 Yeah. Well I think your point about making travel a long range goal is such a great one. It’s definitely something that I’ve coached clients around that want to travel more in their lives. And when I was working full-time for a nonprofit, I negotiated two months off paid because I had tracked a bunch of my overtime and really made this great case to be able to take that two months off and that was my first trip to Bali. And so that is absolutely something that you can negotiate, you can use leverage and see what you can do. Ultimately the premium that we pay for both of our businesses is a price I will willingly pay to be able to adjust our schedules and see the world.

Colin:                       Well it’s good we found each other and we have this in common. So we spent six weeks traveling so we spent more money than we usually went on a trip, but still feel very proud that it fit within our budget. What was a money success that you saw? What way do you think we handled money well on this trip?

Lindsey:                 When we crunched the numbers because we just shared that we, we track expenses the whole time. We both spent about $3,300 each for this trip and that’s for nine different destinations — one day in Beijing, a couple of days in New York City, that’s everything. And I think part of that is just choosing Indonesia where your dollar goes so much farther than in other places like Europe or Scandinavia where we would have to think about what that dollar amount is. That feels like a success.

Colin:                       Sure, Copenhagen is on our list so we know we’re going to be there a lot less time.

Lindsey:                 Yeah. It depends on what you’re trying to do. Right? We wanted to go for a prolonged trip. So what would you say?

Colin:                       Well I think we did a little math that made me laugh, which was one of the ways we budget for this trip throughout the year is we don’t go out to eat at restaurants very often. We certainly do. But it’s an area where we know we can save money. And then you go to Bali or Thailand and it’s so cheap you go out to eat every meal. So I added it up and we went out to eat something like 125 times in our trip. So here I am thinking, we don’t go out to eat as much as other people. And then I thought, no, we went out what would be 10 times a month. Yeah. We ate really well and it was really fun to haggle for food and try new things.

Lindsey:                 Go to the night markets and see that guy cook Pad Thai to Phil Collins.

Colin:                       Or that lady who warned us — don’t eat this, it’s too spicy for you. And we’re like, no, no, we’re cool.

Lindsey:                 It was too spicy.

Colin:                       Our mouths were on fire for like two hours.

Lindsey:                 Oh my gosh. Yeah. It’s such a good point. I totally agree. You definitely think, “Why am I always cooking at home? We like to cook at home, but still it’s important to recognize there’s a bigger pay off for both of us. And I think the point is that we’re in agreement about that.

Colin:                       With any money behavior, know why you’re doing it. Because in the day to day it can just feel like a sacrifice. But when you think about that payoff, it makes it more doable. Yeah. I would love to know, what about travel is important for you?

Lindsey:                 Yeah, there’s this great quote: Don’t listen to what they say, go see. I think that just sums it up, right? Why take someone else’s perspective or word for it? Go and see it. And I think given the inclusivity and equity work that I do, it’s so important for me to get out and be exposed to other cultures. I loved when a couple of years ago you went to like a Diwali festival that was only a few blocks from us. It’s just such a great reminder to travel and to be exposed to other things. That thing could be just down the block from you and you just have to go and seek them out for sure. And you know, it just shows you that, and I know this is woo-woo, but we are all connected. The world is so much smaller than we think, and we have such great commonalities with each other. We had so many fun moments with people who weren’t speaking our same language and you’re just smiling at each other or looking at a beautiful sunset, like that great sunset we had in Bali and everyone was like, did you see that sunset?

Colin:                       It’s not that woo-woo, I think it’s a message that doesn’t get talked about enough that we have more in common than we have differences. And I think you have to remind yourself firsthand. I had a quote too, but it’s from a cooking show. We like this show called Somebody Feed Phil. It’s on Netflix and it’s a thing of beauty and he makes a comment offhandedly that really stood out to me. He said, “Travel is the most mind-expanding thing you can do.” Yeah, that’s such a good reminder because you get caught in your small little lane that you’re in, and your small little world that you’re focused on, and you forget that there’s a group of people making a lot of the same types of decisions for a totally different reason or with a totally different history and you might find that to be beautiful. If you don’t pause to ask, you just might miss it. Thank you, Phil. That is the truth.

Lindsey:                 I love that you brought up that show because that was really our impetus for even going to Bangkok. We saw the floating market that was featured on that show and we were in some of the same spots that Phil was in. And we ate our faces off.

Colin:                       Oh yeah, and we went to Chiang Mai where they had a local dish. They were famous for Khao Soi, and it was one of the best things we ate.

Lindsey:                 Yeah, we should probably get Thai food tonight.

Colin:                       We should send this to Phil. Ok, since you are such a good coach, what are some small actions that we can take? Where do we go from here?

Lindsey:                 You don’t have to do a big international trip to have travel in your life. I think practicing general curiosity about the place that you live. You live there for a reason and my gut tells me you probably haven’t been every place there that there is to see. So I think just practicing general curiosity about the place that you live is a really great first step. I would also say just start planning. This is what Money Date Night is about, right? So sit down together. If you have somebody you plan with and talk about – you know, what’s your style of traveling together and also what are your budgets? Everyone has a different budget that they’re working with when it comes to travel. So those are a couple of places I would start. And also starting to write down interesting, fun places that you hear about. Highly, highly, highly recommend Thailand and Bali. I cannot say enough about those places.

Colin:                       Well that’s our conversation. I hope you’re already excited about somewhere you want to go. And if not to make a list and to start thinking big. Please leave us a review — we’d love to hear how this was for you.

Lindsey:                 And we would always be happy to talk about the cost of any of the trips that we have taken. And we’re going to add that to the show notes on the website so you can check that out.

Colin:                       Absolutely. I feel like I’m already excited for our next trip.

Lindsey:                 Yeah, let’s plan it.

Colin:                       So reach out to us @MONEYDATENIGHT and thank you so much for listening. Yeah, get out there, see the world.

Lindsey:                 See ya.



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