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10 Impactful Money Decisions We Made

Wandering Aimfully Through Our Podcast: What is it all for?

10 Impactful Money Decisions We Made

These are some of the biggest life-changing choices we've made around money over the last decade.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Listen to our full episode on 10 Impactful Money Decisions We Made below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.



Key Takeaways for 10 Impactful Money Decisions We Made

1. First impactful money decision: Combining our finances

Everyone’s relationship is different, but combining our finances forced us to communicate about money early on and we’re so glad we made this decision. It helped us get on the same page with our spending, our future budget, and our big-picture goals.

2. Coming up with a debt payoff plan together

Instead of letting our $124,000 in debt crush us or allow it to make us feel ashamed, we came up with a plan together and we decided we were not going to let our debt suffocate us. Anything you can do to get yourself in a mindset where you’re willing to confront debt is absolutely the thing that you should focus on.

3. Starting WEEKLY financial meetings

The only way we were able to pay down all of our debt in less than 3 years was to meet every week and chat about money. Every Friday we spent 30-60 minutes organizing our expenses, categorizing our spending, adjusting our budget, and having open conversation about our money goals/plans. Eight years later, we STILL have a weekly budget meeting.

4. Hiring financial advisors before we had any money

Financial advisors can help you build a plan to get out of debt. We already had a debt payoff plan in place, but our financial advisors gave us a bunch of helpful structural things and one of them was the account flow of how our money should move between businesses and funnel into our joint household and savings accounts. This is discussed in detail in our debt payoff article.

5. Setting up automatic savings, even when it felt like we couldn’t afford it

You may not feel like you have extra money to save, but you have to start saving before you’re out of debt because it gets you into the habit. We would look at saving $50 or $100 per month to start. Then, we gradually increased it as we were able to make a bit more money and pay down more of our debt.

6. Playing the Credit Card Points game

Please be very cautious if you’re going to play the credit card points game! We learned a ton from nerdwallet.com on which cards to sign up for. When we started playing the credit card points game, we made absolutely sure we could pay our card balance off EVERY month (not carrying extra debt to earn points). These points were used to have a “honeymoon,” a dream vacation after all our debt was paid off.

7. NOT having a traditional wedding

Weddings are an incredibly personal decision, but for us, we decided that paying $10,000 – $50,000 on one day wasn’t worth it (especially after we’d just finishing paying off all our debt). Instead, we eloped and are so incredibly happy we did!

8. Combining businesses

We realized we could earn more by doubling our efforts, but to do that we had to start from scratch when it came to revenue. These are the BIG money decisions that feel scary and feel like there are a lot of unknowns, but you just have to trust your gut and your instincts.

9. Investing in money multipliers: Technology and convenience (meals)

Ramit Sethi talks about this idea of a “money dial.” The term “money multipliers” is just a name we came up with a long time ago, which are things that when you spend money on them, they actually make you more money in the long run. For us, that means investing in new laptops/phones and paying for a prepared meal service (to save time cooking, grocery shopping, etc).

10. Spending MORE money than average on housing and travel

We are homebodies by nature. While we enjoyed our year of travel in 2022, it was a bucket list item and not something we’ll do again. Instead, we enjoy investing in 2-3 memorable travel trips per year. Then, the home that we live in, we will always allocate more money because we spend 95% of our time living and working there. We look at our higher rent payment as paying for flexibility and less stress (because home ownership has so many hidden costs).


Show Notes for Episode 167: 10 Impactful Money Decisions We Made

This week, we’re talking MONEY. Specifically, we want to share some impactful choices we made around money and how they changed our lives and businesses.

If you don’t know, we were $124,000 in debt in 2013 with no plan, zero consistent income, and a lot of stress and overwhelm. How did we turn our mental state around AND pay off 100% of our debt in less than 3 years? You’ll have to tune in to find out!

Money is a tricky topic, but after watching Ramit Sethi’s new Netflix show, we were inspired to be more transparent and share more conversations moving forward about money.

Some links we mentioned:

Watch Ramit Sethi’s “How To Get Rich” Netflix show – www.netflix.com/title/81410436

Read our 8-Step Debt Payoff Plan article (with income flow) – wanderingaimfully.com/debt-free/


Full Transcript of Episode 167: 10 Impactful Money Decisions We Made

⬇️ You can also download the .TXT file of the transcript

Caroline: Welcome to What Is It All For? A podcast designed to help you grow your online business and pursue a spacious, satisfying life at the same time. We’re your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an unboring business coaching program. Every week, we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, what is it all for? Thanks for listening. And now let’s get into the show.

Jason: And I’m here, too. Hi there and welcome to our podcast. This is our podcast.

Caroline: Wait.

Jason: And it’s our podcast. Oh, wait. Go ahead.

Caroline: Do the intro.

Jason: You got it.

Caroline: Podcasts are cool. Dot, dot, dot.

Jason: Nice. Went back. No, it was great. It was good. Yeah, that’s exactly what people voted for. I went back into Spotify. Thank you to our Spotify podcast listeners who have been responding. There’s apparently like, quote unquote, Q and A. I don’t know why they’re not calling them comments, because that’s really what they are. But it’s listed as Q and A. But we didn’t ask any questions.

Caroline: It’s just A.

Jason: It’s just A’s.

Caroline: But maybe you can ask a question.

Jason: You can, for sure. But like…

Caroline: But you didn’t.

Jason: It’s just very weird the way Spotify is doing this.

Caroline: But we’ve been asking for podcast comments forever, so that’s very exciting.

Jason: It is very exciting. One of these days we’re going to do like a two week blitz of Apple reviews.

Caroline: I thought about that. I was like, we really haven’t talked about reviews forever.

Jason: Just like something to kick it up because we know that our show is growing. Like, I can see it in the analytics.

Caroline: It is?

Jason: But you listeners…

Caroline: Because who wants to write a review?

Jason: We just never talk about it either. So it’s like people don’t think about it. It’s the same thing. Like, when I watch…

Caroline: I’m not blaming anyone.

Jason: I’m blaming four of our 27 listeners.

Caroline: And you know who you are.

Jason: You know who you are.

Caroline: The four of you.

Jason: People who wear pants.

Caroline: Clap through.

Jason: You people who have hair. You people who…

Caroline: Have hairy pants?

Jason: Say stuff. We did get a couple of folks who liked my pants analogy of adding all the zippers and things of WAIM pants when I talked about this, where our price will go up because our WAIM pants got more features on them. Let’s talk about, just very quickly, the preamble to the preamble, didn’t have an episode last week and just being honest about it.

Caroline: We didn’t have an episode last week because one of us was a little overwhelmed. And I’m not going to tell you who was who.

Jason: Thank you for outing me. Geez.

Caroline: And the other person said, listen.

Jason: If you’ve been listening to this show long enough, you’ve heard us do this before. It comes down to like, we’re overwhelmed. There’s a lot of stuff going on. You’re overwhelmed. There’s a lot of stuff. We’re overwhelmed. Oh, my gosh. That was a joke. We’re overwhelmed. There’s a lot of stuff going on. Something has to give. So what’s that thing? And so for us, the podcast is typically the thing because our newsletters are mostly pre written. So it’s like those don’t have to give and, in some cases, they have.

Caroline: Doesn’t save us a ton of work to do that.

Jason: It’s just this is the more kind of like, passive thing that we do with you listeners.

Caroline: But we care about you so much.

Jason: I want you to know we had a full on discussion where Caroline was standing at one end of her house, I was standing at the other end.

Caroline: We were.

Jason: And we’re like…

Caroline: I was like…

Jason: Should we take a break? You’re like, I don’t want to take a break. I’m like, we’re two days away from… like, no, we’re not doing this.

Caroline: Yeah, you stood your ground. And you said, no, listen, we’re going to take a week off. The world will not end. Sometimes it’s the other way around where I’m like…

Jason: For sure.

Caroline: We got to scale back. It’s not the end of the world. So we’re a good team in that way.

Jason: And we’re going to talk about a lot of team things here with money. But first let’s talk about the actual preamble, which was a little staycation in Ericeira.

Caroline: Yeah, what I didn’t share is that part of the reason we were overwhelmed is because we took a staycation and all of our stuff piled up. But you know what? It was worth it.

Jason: Well, we really kicked this year off with a lot of focused effort from January 1 until last week.

Caroline: Which has felt great. But you know.

Jason: It catches up with you. It does.

Caroline: It catches up with you.

Jason: No matter how long you’ve been doing this and how many processes you have in place and how many Notion wizards are on your team, you still end up needing a break from doing all the things.

Caroline: And I was telling a friend that technically it was probably a bad just bird’s eye view timing wise, taking a staycation was bad, but that’s also the time when you need it the most.

Jason: Because if you don’t do it then, what you’re going to run into is burnout.

Caroline: Exactly. So I’m actually glad that we took three days away from our laptops and we went to this little town of Ericeira, which is how far away from Lisbon? It’s like directly west, isn’t it?

Jason: Ericeira is tricky to get to because it’s on the coast and it’s west, but there’s not really like a main road that goes to it. But I think as the crow flies, it’s like 30 km would be my guess, which is like 15 miles, so it’s not that far. But there’s like no… it’s a coastal road, so it’s a…

Caroline: So it’s right on the coast and…

Jason: It may be further than 30 km.

Caroline: Cool little surf town. Like it has very surf culture, very laid back California vibes, but more sort of populated than a lot of the beach towns up near us, which, if you don’t know, we are probably like 45 to 50 minutes north.

Jason: Well, the funny thing is, we’re further away from Lisbon than we are from Ericeira, but it takes the same amount of time to get to both.

Caroline: Right.

Jason: Because coastal roads as opposed to, like, a regular highway.

Caroline: We did discover that the route from here to Ericeira is actually a beautiful coastal drive.

Jason: It’s just one of those, like it reminds us that certain parts, the route one drive or 101, I can never remember which one it is in California, where you’re, like, in the Big Sur, windy with the cliffs and things. Like parts of it feel like that. It’s not quite that. But there’s that one lagoon that has this crystal clear blue water that’s lovely.

Caroline: So we enjoyed that very much. The whole precipitating event for doing this staycation is that we’re not on Instagram anymore. But occasionally I go on to update my friends and family of our life in Portugal or whatever. And so I got fed, like, this ad.

Jason: Well, because, funny thing.

Caroline: What?

Jason: Your other account that used to be your main account forever, your @ckelso account on Instagram, you somehow got put in… this has happened to you twice now. We’ve mentioned this on the podcast, I believe.

Caroline: Yeah.

Jason: On Hulu, you were watching Hulu, the app, one time, and you’re like, hey, babe, have you ever seen this? And you showed to me and it said, like, dog food in the corner, like a watermark.

Caroline: I was somehow in this like…

Jason: You were not watching a dog show either.

Caroline: I was somehow in this weird test group for a new version of Hulu. They were testing out, like, a new interface, I imagine, is what happened because it said, Hulu dog food.

Jason: And again, not watching pet shows.

Caroline: I’m so glad that I showed it to you because no one would believe me. So if you are listening and you somehow worked at Hulu or something, like, please email us and let me know.

Jason: We don’t have anybody listening from Hulu. That’s all right.

Caroline: We don’t know that, but please let me know. Was I in a weird test group? Anyway.

Jason: Does anybody listening to our podcast work for one of the streaming services? Now, I’m curious. Like, any of them? Showtime? Max?

Caroline: Side note from the Hulu dog food. The reason you brought that up is because on my @ckelso public Instagram account, I don’t see ads.

Jason: Have never had.

Caroline: Never had them.

Jason: Wild.

Caroline: Don’t have feed ads, don’t have story ads. Like, I don’t know what special list I’m on. And so I was just enjoying Instagram as a user. But now that I have this little just private, like, it’s literally like, my mom follows.

Jason: And my mom. It’s our moms.

Caroline: And your… our moms. And I get ads on that account. But now I’m sort of like, this is cool. Everyone who’s seen Instagram ads for all is like, it’s not cool.

Jason: It’s not cool.

Caroline: But to me it’s cool because I’m like it was just feeding me, like.

Jason: Well, and here’s the thing, the difference between our two accounts. When Instagram ads started to get popular, and especially as they started to listen to your conversations, I would mention shorts. And I would just get all the shorts ads.

Caroline: Exactly, I’ve been like, bathing suit, bathing suit, bathing suit.

Jason: And you will get ads for bathing suit companies. But anyway, you got an ad for this restaurant.

Caroline: Yes, which I will say also, I have to be careful because Instagram, if you let it, it will suck you right back in. So even though I have, like, follow five people or whatever, it will suck me right back in. So I am very careful to only spend a short amount of time there. But I got fed this ad for a restaurant called the Capsule Cafe in Ericeira, and they were doing a special tasting menu event where the chef at the restaurant is actually a Ukrainian chef named Chef Alex. And he does these collaboration pop up dinners with other chefs. Like, I think he did one with, like, a Berlin chef. And then for this one, it was a chef from Lisbon. So it was a Portuguese chef named Chef João. And they basically decided to collaborate and do an eight course tasting menu, four dishes from each chef, calling it like, Ocean and Land. So Chef João from Lisbon brought these sea dishes with ingredients from the sea. And then Chef Alex did like vegetables. And yeah, there wasn’t a meat course, was there? No, just vegetables. And so, you know, if you’re listening, we love culinary experiences. We are those total Chef’s Table geeks.

Jason: Oh, yeah. If you’ve seen the movie, The Menu, we’re the overeager guy who’s like, okay, chef, I can see in here that this clam lived in a rocky terrain.

Caroline: Isn’t the whole point of that movie, that it’s like a parody of that person and it’s making fun of them? And yes, it is. And we deserve to be made fun of for that.

Jason: Totally fine.

Caroline: We immerse ourselves in that world, and we love it. So we basically built this whole little staycation idea around that. We also had friends that we wanted to meet, like sort of online friends to offline.

Jason: Hadn’t met them in real life.

Caroline: Hadn’t met them in real life yet. So it was just this lovely little weekend. We went down on a Friday. We ate at this amazing restaurant overlooking the ocean.

Jason: And then oh, well, hold on. So to finish off the Capsule Cafe dinner, it was fantastic.

Caroline: I was getting there.

Jason: All the courses.

Caroline: I was on Friday, so I was going to get there.

Jason: Okay, yeah.

Caroline: So we have lunch at this Ocean restaurant. We check in a motel, and then that night, we go to dinner and man, can I just say…

Jason: It delivered.

Caroline: It delivered.

Jason: It was fantastic. It was worth every penny. It’s just a great meal. I mean, it was so fun. The restaurant is so tiny. Like, imagine the size of your kitchen. Now add six tables that people can sit at. That was the size of the restaurant. And it was just so fun to have the chefs come out and show their dishes and just have them talk about it and kind of share the inspiration for it.

Caroline: Also, we should share the highlight.

Jason: Absolute highlight.

Caroline: Of the meal. There were two staff members that were incredibly ticket over the top. And those staff members happened to be four legged staff.

Jason: Covered in fur.

Caroline: They are a dog friendly restaurant. And so there were these two dogs. One was sort of like a golden retriever esque dog, and another one was a corgi.

Jason: With an undocked tail, which I’ve never seen a corgi with a full tail.

Caroline: And so we were sitting at a booth at the very back of the restaurant, as far back as you can get.

Jason: Again, it’s the size of your kitchen. It’s not very big.

Caroline: It’s like a galley kitchen. And so the two dogs, like, periodically, through the meal, would go back and greet every table.

Jason: Just like they were looking for food.

Caroline: Yeah.

Jason: They didn’t really care about the people.

Caroline: But, oh, my gosh, I had a couple of moments where I was like, did I dream this up? I’m eating this beautiful tasting menu in this country that I now live in that I love with dogs, with a corgi greeting me? I just was, like, living my best life.

Jason: There’s just something about the openness to the culture in some ways here that’s very different than you’ve ever experienced. You would never go to an eight course tasting menu in the United States that I know of. And they would allow dogs to roam around.

Caroline: I’m sure it exists in certain areas.

Jason: But it’s just, like, not at all…

Caroline: It’s unusual, for sure.

Jason: So it was a very fun like, haven’t experienced this before. This is great. It probably made the meal that much better because we could pet dogs the entire time.

Caroline: It was so delightful. And some of my… I won’t take you through every course, but I will tell you a highlight for me was I think the second dish was a vegetable tiramisu, which is wild. But chef Alex was like and he said, this is like a big hit. They do a twist on it every single dinner because it’s that big of a hit. But picture the texture and layers of a tiramisu dessert, but with savory ingredients. And so you have layers of vegetables that are cooked to perfection. He even incorporated white chocolate, like a white chocolate mousse, which I know sounds so strange, but it was like the perfect sweet and savory with, like, a beetroot dusting over the top. Like, you know how they dust the chocolate?

Jason: Your girl’s coming around the beetroot, by the way. And beets in general.

Caroline: I am developing a taste for beet. It took me a long time to get here, and I still think it tastes like absolute dirt, but I’m sort of…

Jason: But you kind of enjoy it.

Caroline: I’m kind of enjoying the dirt now.

Jason: That’s like becoming a workout person. It’s like you hated in the beginning. But now like…

Caroline: Who is this girl?

Jason: So to contrast that dinner, that was absolutely fantastic. At the hotel, we booked a package that included two things. So we want to share a quick little aside to both of them. Love the little hotel. It’s a great little beach hotel, and it came with massages, and it came with a quote unquote romantic dinner.

Caroline: Yeah, they had this promotion that was a great rate. You had like two nights for the third one free, and it came with a romantic dinner and it came with massages. And I was like, yes, please.

Jason: This is great. So let’s quickly go through the romantic dinner. There’s only one restaurant in the hotel, so it’s where you eat breakfast, it’s where you can eat lunch, and it’s where you eat dinner.

Caroline: And it’s a very casual restaurant. I thought there was like a different area. There is not.

Jason: No, no. One restaurant. The best part is that the restaurant overlooks the indoor pool, which then overlooks like a sitting area outside, which then you can almost kind of see the water. So I was already thinking about this. I’m like, where is the romantic table going to be? And I told you, I was like, I bet it’s the one up against the glass that looks right at the pool. And by the way, this is not like an extravagant pool. You’re like, wow, this is amazing to look at. No, it’s just like a steamy room with water on the ground. Like, that’s all it is.

Caroline: And it kind of smells like chlorine.

Jason: And it kind of smells like chlorine. So sure enough, where was our table? Right there at the window by the pool. Then it was just like 15 minutes radio silence. Like, no one came up to us.

Caroline: They forgot about us.

Jason: And I was thinking while we’re sitting there, like, we were just laughing because we’re like, this is just hilarious. And contrasting it to the night before, which is an incredible meal. I’m like, is this part of it? It’s just like 15 minutes for us to connect before we just get in the mood or whatever.

Caroline: Make out? I know.

Jason: And then it was apparently a fixed menu of some sort where we only could choose like a couple of different options.

Caroline: So we have taken the 15 minutes of radio silence to debate everything on the menu.

Jason: Because we have the menus in front of us.

Caroline: They did give us the menus. We still have not yet gotten beverages or anything. So we’re like, let’s just decide, what do we really want? So we’re talking about every… we finally get our order together, we’re going to be ready. And the guy shuffles back and is like, oh. And he prints out first of all, definitely not like a forward facing document.

Jason: Shouldn’t have been the page…

Caroline: It’s like our entire…

Jason: Itinerary.

Caroline: Itinerary readout of who these people are, what they booked, what it comes with, what it doesn’t come with. I’m like, you definitely shouldn’t be showing this to guests, but that’s okay. And then he’s like, and here are the options. They never told us that it was you can only choose certain options on the menu. This whole time we’ve been debating what we’re getting, and then we’re like…

Jason: None of those options were on the menu.

Caroline: And then he leaves.

Jason: Yeah, he just leaves.

Caroline: And then you and I are both like, well, now we really want these things that we decided. So he comes back, and I was like, hey, hey, we’re just not going to do this. And it’s okay. We’ll pay for it, but…

Jason: We’ll just pay for dinner.

Caroline: We just really want these items on the menu. And then he was like, okay. And I get it right, because he wasn’t anticipating that or whatever, but he looks so flabbergasted. And then he’s like, okay. And then he doesn’t take our order. He goes away. He takes our drink order. He goes away. I’m like oh, no.

Jason: It’s about 45 minutes until a morsel of food hits the table. And we’re just laughing because some of you may have heard this about European meals. It can take a long time. We have yet to have an experience, and we have eaten out a lot, where you don’t get food for 45 minutes. It has not happened yet. This was just like the perfect storm of hilarious things.

Caroline: And that’s why I feel like we’re sharing it, because sometimes you book a romantic dinner and no part of it is romantic whatsoever, but you just have to laugh it off.

Jason: I will tell you, that a nice cocktail with a waff of chlorine hitting your nose. It’s a good combo.

Caroline: I also won’t even get into, like, my drink order was wrong, and then I was going to just be okay with it, but then…

Jason: You end up getting a dusty drink.

Caroline: But then Jason was like, no. And so he stops the waitress. Then she brings the correct wine.

Jason: In a very nice way, just so everyone knows. I’m not like, Excuse me, garcon.

Caroline: No, but anyway, it was just a comedy of errors. The entire thing was a comedy of errors. I will say food was delicious when we finally got it into our mouths.

Jason: Food was great, and the portions were absolutely enormous. We had a whole meal that we took home for both of us. The second part of our package included massages. Now you got a very normal massage. The only weird thing was you didn’t flip over, which is fine, but they squeezed your muscles and they worked on your body.

Caroline: Like a normal massage.

Jason: Like a normal massage. My massage. And I know the mic is going to be able to pick this up. A lot of this, that is me slapping my head because I got slapped. I got, like, hands rubbed together to make a fire on my hairy legs, which doesn’t feel great. There were just a couple of different…

Caroline: Snaps. Give the snaps.

Jason: Oh, yeah. There was like a (snapping sound) in my ears. Like, she wasn’t touching me. She was just making sound. I had, like a whole sensory experience. None of it was getting my muscles rubbed or moved in any way whatsoever. One of my favorites was she lifted up one of my legs and spread it apart, which is… we kept our shorts on because they told us to. But if I wouldn’t, that would have been very interesting. And then she was just poking the inside of my leg, which is a very tickly place for anybody, even someone who’s not ticklish. So at that point, I’m like, first of all, none of this is relaxing. And then it’s like five minutes up. Like, you can tell. I have flipped over. She’s, like, finishing up. She’s, like, slapping my head. I’m like, okay, we’re almost done. Then I get, like, a five minute guided meditation, and I just like, my feet are in the sand. I’m releasing the feelings of my body. And then she’s not touching my face, but I can feel her hands are, like, moving around my face. And I’m dying laughing because I’m like…

Caroline: You forgot to tell them about the chin tickles.

Jason: Oh, I got chin tickles as well. At one point, she just, like, literally imagine going up to a child and reaching under their chin and be like, with your fingers. She did that to me during a massage.

Caroline: Because I’m next door to you having a completely different experience. I walk out.

Jason: You’re having a massage.

Caroline: I almost fell asleep, which I don’t normally in massage, but I was tired. And so I walk out and I’m, like, so relaxed. And I just see this look on Jason’s face, like he’s just been through something.

Jason: Yeah, the tickles, the wiggles, the pokes, the slaps, the non-touching touching. Anyway, that was an adventure. So that was our staycation. It was very enjoyable. We are excited to go back. We definitely want to go back to that restaurant.

Caroline: I will say I loved Ericeira and it was a really cool… I think it’s a really cool little town and just lots of cool shops and coffee.

Jason: It’s definitely more tourist…

Caroline: Exactly.

Jason: Driven. It feels like a beach town.

Caroline: And what I was going to say is it’s just such confirmation, though, that I’m so happy with where we live because to be in this calm and peacefulness and sort of out of the touristy places for 90% of the time, and then to be able to just go there for fun trips and everything. I don’t know. I think this entire year is a good exercise in testing out different places so that we can then go no, still like our place the most.

Jason: Still like our place. I have one major thing to touch on before we get into the episode.

Caroline: Please.

Jason: That’s extremely important. The day that this episode comes out is the day before the rest of this year is quite over for me.

Caroline: Right. So no more podcasting because…

Jason: I will not be here. I will be leaving Wandering Aimfully and Teachery, our businesses.

Caroline: To go full time as a…?

Jason: I will be living on the couch. I will have my controller in hand because Zelda Tears of the Kingdom, T-O-T-K, as we all know, TOTK, comes out the day after this episode goes live. So it’s been really great knowing everybody. As we like to say around our house, Tenha um bom dia.

Caroline: Tenha um bom dia.

Jason: Which is just as we said, Have a good day, in Portuguese. So that’s it for me. I hope you all have enjoyed me being here. I will not be here any further for the rest of this year.

Caroline: You are indisposed. Indisposed.

Jason: I’m disposed from this podcast until 2024.

Caroline: I’m so excited for you.

Jason: I’m very excited as well. Okay, those are our preamble notes. And now it’s time. Also, by the way, if you’re a TOTK fan, you’re super excited. You can send us an email, let us know what you’re most excited about. Maybe it’s the weapons building that you’re excited about. Maybe it’s the Ascend feature just going up through mountains. I don’t know if you’re interested in kind of like runes and the different things that are going on, you could just let me know on any of those things. I’d be curious to find out. Okay, let’s talk about these ten money decisions starting with number one. We’re going to dive right in with a kind of a fun one.

Caroline: Excuse you. I would like to do an intro.

Jason: There’s no intro listed in our notes.

Caroline: Know my body. When have I ever in the history of…

Jason: Jumped right in?

Caroline: Ever been like, And starting with number one. You know, I have to do a diatribe. Okay, this episode we are going to share with you ten good money decisions for us that we feel like have contributed to the financial position that we now find ourselves in. And this episode was precipitated from us watching the new Netflix series. This is not any type of ad or promotion or anything, but we were just interested in it. What is it called?

Jason: How To Get Rich.

Caroline: How To Get Rich or something? It’s Ramit Sethi’s show on Netflix. And we have…

Jason: How To Be Rich?

Caroline: How To Get Rich?

Jason: Something with getting rich.

Caroline: Yeah, that’s the whole shtick, right? They lure you in with this whole, like, how to get rich, and then they’re like, hey, but actually rich doesn’t mean money.

Jason: If you know Ramit’s stuff, you know that it’s not about that.

Caroline: Exactly.

Jason: We have definitely consumed some of his content over the years.

Caroline: Yeah. And I’ve appreciated that he does try to… It’s really just about good money habits and about defining what you want to spend your money on. And in my opinion, I think he does a really good job of walking that line between yeah, he’s a very skilled marketer, but I think his educational content is quality and I think he doesn’t try to hit it too far home, you know what I mean? Like just trying to do all the sleazy tactics. So anyway, but I haven’t consumed his content in a very long time. But I did watch one of his podcast episodes, like a few weeks ago, was recommended to me on YouTube. And the thing I really like about his podcast is he brings these people on and they’re extremely vulnerable about their finances and he, I think, is a really good listener and I think he helps them walk through some of the decisions they’re making, like how to just it’s almost like couple therapy through money.

Jason: Oh, absolutely.

Caroline: And so it turns out that’s a lot of what the series is and we watched it in like we are almost finished with the entire thing. We watched it in like two nights, but it opened up all these conversations that we haven’t had in so long about money. And we don’t talk about money in a very direct way on this podcast. Like, we talk about business, we talk about marketing. Money is obviously a part of that. But if you’ve been listening for any amount of time, you know we’re not all about the money. That’s not what our focus is. However, I was watching the show and I was going, man, I think I really do take for granted sometimes how many of these decisions and conversations we had early on that we are only where we are today in this financial position where we don’t worry about money in the way that we were so used to.

Jason: Oh, for sure, yeah. And just to be clear, for context, we… It’s not like we’re at a place where we don’t have to make money moving forward. We didn’t sell a business and…

Caroline: Yeah, we just don’t have to worry.

Jason: Made a whole bunch of money. We still have to work to bring money in. We just are now at a place where it’s very predictable. We now are very profitable.

Caroline: And I don’t worry about money in the same way.

Jason: Yeah, five years ago we worried about money.

Caroline: That I used to, and certainly not in the way I grew up, which was very, in a lot of ways, financially insecure.

Jason: So yeah, I think just to add further context to it, I mean, I think it might be interesting just for everyone to know we both grew up in lower income households, but not to say that in the grand context of things, it wasn’t poor.

Caroline: Right. No, if you would have asked me probably even maybe five years ago, I would have said we were in like lower, like upper… upper lower class.

Jason: Yeah.

Caroline: Is what I would say. But now, knowing the full context, I’m like, oh, okay, we were middle class. But money was always a…

Jason: But it’s like in your group of friends.

Caroline: Yes.

Jason: Like and it’s like in the context of society, middle class, for sure. In the group of friends that we both kind of grew up in throughout time, it felt like kind of like upper lower class, if you will. And that’s not a criticism of our parents or anything like that. It’s just kind of like…

Caroline: Gives context.

Jason: Yeah.

Caroline: But I mean, yeah, never not having food, but also being like, oh, you can’t go on this field trip because it’s $100 and we don’t have money to pay for it. Or like you can only buy a yearbook two years out of the four years of high school because they’re too expensive. And I think we can all agree they are too expensive.

Jason: I can’t believe my mom let me buy a high school class ring. I did not need that.

Caroline: There was no realm of possibility I was getting a class ring and also…

Jason: Societal pressure.

Caroline: Paying for college by myself. Like my parents didn’t put a dime towards college. I mean, they did pay towards… I will say they did Bright Futures, which I think gives you like in Florida…

Jason: Which is like a Florida scholarship thing.

Caroline: So I guess that’s not entirely true, but I still had to take out student loans and pay for it myself and all of that. So that gives context.

Jason: Yeah. So for me, I was just going to say my context was grew up that way until like late teens and then my family had more money then.

Caroline: Had a total switch, right?

Jason: And it wasn’t like we were extravagantly rich and all that, but we did have plenty of money and so I didn’t have to think about it necessarily.

Caroline: Which must have been a weird shift.

Jason: It was an extremely weird shift, for sure. And it also it’s like all these things that I’ve come to learn as an adult, I couldn’t get shoes as a kid that I wanted. And so in college I had this habit of like, I worked a job and all the money I made, I paid for shoes. That was it. I had 70 pairs of shoes as a college student, and you don’t need that many pair of shoes.

Caroline: But you were like… which is what I think is so cool about the show. And again, not an ad, but I just think this stuff is interesting is you see people kind of playing out those patterns of like, I didn’t have and now I have and so I want to buy these things because my brain is still telling me that I never had these things.

Jason: Just to finish our context stories. So I started my entrepreneurial journey after working for two and a half years in a nine to five job. Basically made a good amount of money the first couple of years. And by good, I mean like $100,000. Like it wasn’t like crazy money, but that’s very good money.

Caroline: Very good money.

Jason: And you started working out of jobs that made like $30,000 a year. And then from there we piled up a bunch of debt, $124,000 in debt. Thank you to those previous businesses that I created that didn’t pan out. And then we kind of like scrapped around for a couple of years, just kind of did everything we could. Then we’ll get into some of the things that we learned that helped kind of shift that whole trajectory. And then I would say 2015 and beyond was where our money kind of turned back to the positive side. Then we got into building WAIM and it was at that time when we really didn’t have any predictable income at all.

Caroline: At all.

Jason: And then we spent three years building that up to get to the place that we are now, where we have very predictable, comfortable income that’s very profitable. I just want to give the full journey.

Caroline: That’s the full journey.

Jason: Of our context.

Caroline: Yeah, I think that is helpful for people who don’t know our story and we’ll get into the micro of each kind of step along the way. But again, just to lay out the conversation, I thought it’d be cool to go through ten different I guess you could call them decisions, but just for us personally.

Jason: Tips?

Caroline: I would not call them tips. And here’s why I don’t want to call them tips.

Jason: Yeah. No, I get it.

Caroline: Because I think financial advice is so hard to give to people because everyone is working with such different circumstances that it’s almost like…

Jason: Yeah, I mean, the interesting thing, if you just heard me tell our macro story, is like, you probably fall somewhere on that spectrum.

Caroline: Exactly.

Jason: Right. So it’s like you might be at the journey we were at, like 15 years ago. You might be the journey we were at five years ago. It’s hard to know where anybody is, so I totally hear you on that. And I was just…

Caroline: And that’s why I think the most helpful thing you can do is just have transparent conversations where people can pick things up and go, oh, maybe I should think about that a different way. Or maybe this is something I want to spend money on and this is something I don’t need to spend money on, or whatever.

Jason: Because we’ve even listened to those podcast episodes of people who are way more well off than us, and they’re like, you spend $50,000 a month on that? And it’s just like, that would not be for us. But it’s like, fine, that’s fine for you. It’s just we can take that information and be like, we’re not going to work on that.

Caroline: Totally.

Jason: Let’s get into it now.

Caroline: Let’s get it. Now, we’ve done the pramble pramble pramble.

Jason: Okay, great job. So number one, combining our finances, money decision number one.

Caroline: This is a hot topic. Listen, I also want to say I’m not saying that the right answer is to combine your finances. I think everybody has their own way of doing this. I’m just saying for us, I think one of the most critical first steps was probably within like after one year of dating, we combined our finances. Do you think that’s a bad idea?

Jason: I don’t think so. I mean, this is something where I give my mom a lot of credit and the way that she brought me up, like, helping her balance our checkbook, helping just understand some things because there weren’t a lot of people around us that were talking about money. So it was like a very kind of open book conversation in a lot of ways, and I think that was really helpful for me. So I think when we started dating, and even in previous relationships to that, keeping your money siloed and apart and listen, I understand why this is a thing, and there’s a lot of stuff that goes along with that, and there’s a lot of things that people brought along with their childhood that keeps the money separate and what have you. But I just thought for myself, if I’m going to have a full time partner, I want to get in as quickly as possible to understand our money situation.

Caroline: As opposed to a half time partner?

Jason: A quarter time partner, a third time partner. Whatever it is.

Caroline: I’m trying to go way back to the beginning because I think the reason we did keep it separate is obviously you don’t want to just be combining your finances with every person you’re casually dating.

Jason: Of course.

Caroline: But you and I, we never had a casually dating phase. Like, we went from zero to 60 so quickly. We just were like, oh, no, this is it.

Jason: Right.

Caroline: We had those couple of months of figuring it out, and then once we got past that, we were just like, no, this is it. So by the time that I moved back from North Carolina, we were doing long distance for like six months. I moved back to Florida. I moved in with you, which was kind of like, supposed to be a temporary thing, but then just very quickly…

Jason: We’d been dating for six months at that time?

Caroline: Exactly. And then by that Christmas, which no, yeah, that was six months. That was when I moved back. Yeah, by the time that I had been living with you for a month, it just became clear that we were all in. And I think probably a few months after that is where we started having the conversation because the context here is I took a pay cut to move back to Jacksonville. So I think my first starting salary was maybe like $35,000 a year, and I took a pay cut to like $32,000 a year, but it was to be closer to you, and it was to like I was unhappy in this role as a media planner, but I was making so much less money than you.

Jason: Right.

Caroline: Because I was like 22 at the time. You’re 27. You’ve got so many more years under your belt. You own a house. And so I just remember we would go out to dinner.

Jason: Well, this was also at the peak of I Wear Your Shirt times.

Caroline: Peak of I Wear Your Shirt. So you had plenty of money. And also, anyone who knows Jason from this podcast knows that if we’re going out to dinner, he’s going to order… he’s going to order an appetizer. He’s going to order a dessert.

Jason: Double desserts, baby.

Caroline: I am coming from… First of all, I’m not that far away from my childhood at that point where you do not order appetizers. You do not not order dessert at a restaurant. It is just off the table, like, maybe a special occasion. But we don’t have money for appetizers. Are you kidding me? Much less eating out very often. And so we would go to these things, and then we would go to split the bill, and I’d be like, hey, if we’re splitting this bill, it’s a no app kind of night. And I think you probably felt very restricted.

Jason: I’m like, I’m not about to not have one app, let alone two apps.

Caroline: And so I think the combining of finances did come from this place that we were so almost, like, unequal in our finances, but we were trying to be equal in our partnership. And so it was this decision of like, okay, let’s just be real about this. At that point, I was never, like, paying you rent or anything. I know some people do that. And so it was like, okay, we’re both kind of splitting the just living together, so let’s just commingle. And it was an easy decision for us. And maybe it’s because we were so all in in the relationship, and I know that’s not the case for everyone.

Jason: Yeah, I mean, I think that one of the things when we watch shows like Ramit’s show or any finance shows, and you see a couple and they’ve been together for years, and even if they’re, like, married and they still have separate finances, it’s just such a point for us to be like, I don’t know how they do that. It would be such a point of friction for us. And I’m not saying it’s bad for you to do that. And if you’re listening to this and you have separate bank accounts from your partner, that’s totally fine.

Caroline: I just think it would be a challenge not to get into to a score keeping mindset.

Jason: And it’s the whole resentment thing, right? It’s like, oh, well, you bought this and you bought this, and like, yeah, you have your own money, quote unquote, but we have a home together.

Caroline: But see, now I could see how it’d be the opposite, where if your stuff is shared, that’s where it can get resentful because it’s now your shared pool. So it’s like, but you bought that. But you bought that.

Jason: Yeah, but that’s where you agree to your budget things, which we’ll get to in an upcoming point that you create a level playing field for everyone to be like, okay, we agree that this is the money we’re going to spend.

Caroline: Well, that’s really why I wanted to share this one point, because I think this was the beginning of our journey. By combining our finances, it forced us to communicate about money so early on and to be like, okay, why are we doing this? And what do we want to pay for? And again, I know people who have been burned in relationships where they did commingle finances, and then the relationship ended, and that was a really painful part of the process, was, like, trying to unmingle. And so I knew maybe there was some risk there, but for us, I just felt like there was so much more to gain, and I was secure enough in our relationship that I was just like, okay, if one day we split up, we’ll figure it out. Did you ever feel, since I was making so much less than you, did you ever feel when we combined finances, that there wasn’t much in it for you? Did you feel like I was…?

Jason: No. I think this is where my very focused brain is like, I’m already living my life where I have a house and I pay for meals and I do these things. And bringing in another person doesn’t take away from that at all. Sure, maybe it ups the bill at dinner, but it doesn’t change my mortgage. It doesn’t change my main expenses of life.

Caroline: Right, so because you were already operating in a financial way where you were not living beyond your means.

Jason: Right.

Caroline: It didn’t feel stressful because you just were like, oh, well, I’m just adding.

Jason: Yeah, if anything, like, it’s just my Chili’s bill is, like, $20 higher.

Caroline: You never took me to Chili’s.

Jason: That’s not true. We definitely went Chili’s because we got Presidente Margaritas, no doubt. 100%. Yeah. Back in our early days.

Caroline: Are you kidding me? I would have loved those crispers.

Jason: Chicken crispers. Yeah, no, I don’t think I ever thought about it. And if anything, it was always a weird thought to me to be, like, charging you rent. And I understand why people do it, but for my own personal thing, it’s, like…

Caroline: Never felt right.

Jason: If we were going into a new place together, I could be like, okay, this might make sense for us to split this in some capacity. But again, I already had a mortgage. I already had a place that I was living in. It didn’t make any sense for me to charge you money to do that. And again, I understand why people do that, but it just for me, it just for my brain, it makes sense.

Caroline: And probably I’m sure because we had so many conversations, there was probably a little bit of understanding, too, that I did take a pay cut to come back to Florida for us to live together, too. So it was a little bit of understanding on your part of, like, I understand you’re making even though it wasn’t that much less, but you’re still now making less money, and you’re doing it for kind of our relationship and to have that be healthy.

Jason: To me, I like things to be easy. So even when we go out to a meal and this is the case even…

Caroline: And I’m the same way.

Jason: This was the case even when I didn’t have money. We go to a meal with friends, I would rather just pay the bill…

Caroline: I know you would.

Jason: Than do the song and dance of splitting. And, like, who had this, I just don’t want to do it. I would rather just end the meal. And we’re like, that was fun. Oh, the meal is paid for. How’d that happen? And then I can figure out how to pay off my credit card later.

Caroline: And this is where I do think that this is lucky that we’re both like this because I’m the same way, right? We’re both very practical in that sense, where I’m just like, isn’t this just easier? And maybe that’s actually even a bigger way of why we combine finances. We were like, Isn’t this just easier? We don’t have to do the thing and Venmo and whatever. But that actually parlays into the next decision.

Jason: Let’s do it. Number two.

Caroline: That, I feel like, was a good money decision for us, which was okay, so then we find ourselves… so things were going great with I Wear Your Shirt.

Jason: I bought too many Chili’s dinners.

Caroline: Way too many Chili’s dinners. And then we find ourselves in a position where the business is now going downhill revenue wise. You can see the writing is on the wall.

Jason: Too many expenses, not enough for revenue.

Caroline: Too many expenses, not enough… Very unbalanced cash flow, I think, was a big problem in that business as well. And so then we’re now at the place where now our finances are commingled, and I’m not riding so high anymore. I’m not really enjoying this because now, I’m kidding, because by that point, I very much did see all of our money as the same money. And by that point, I’m working for the business. So really, our faiths were tied together at that point.

Jason: And this is, like, two years later.

Caroline: And that’s two years later. And then we’ll spare you the details of, like, we get in this position where you try to hang on to the business as long as possible because there’s people’s salaries, and basically you were paying for people on your credit card.

Jason: And I tried everything. Like, I maxed out six credit cards. I borrowed some money from family. We actually took, like, a micro loan from an investor in town. That was a whole rigmarole and just, like, literally everything I possibly could until it got to a place where I was like, well, I have basically accrued $95,000 in debt to keep this business afloat. It is time to give up.

Caroline: Yeah. And I give you a lot of credit because you did try everything, but even you had this buffer where you said, this is no longer like, this is now getting into a territory where this is a bad decision. I’m getting myself into a hole that I might not be able to climb out of. And as hard as it was, and I saw how hard it was for you to let people go and the anger that creates, and people misunderstand your intentions or whatever, and no one will ever know how difficult that was for you except for me because I was there. But that’s what happens when you run a business with people, is you have to own it, and you have to stay accountable, and it doesn’t matter how people feel, right? But then we have all this debt.

Jason: This is point number two. We’re getting to it.

Caroline: And so I think point number two, which was the best thing we ever did, was instead of letting that debt crush us, or instead of allowing that debt to make you feel ashamed, and so then we just pretend it doesn’t exist, we came up with a plan together, and we said, we are going to not let this suffocate us. And I think it was also like, okay, precipitated by maybe a little bit of like, you wanted to pay your family back, because that sense of…

Jason: It’s also that and it’s anybody who knows this…

Caroline: It’s different than the bank, right? And it’s not like you took crazy $100,000 from your family or whatever.

Jason: Right.

Caroline: It was mostly the bank. But still, I think that was an important part of it, is like, if people believe in you and they help you out, you have more of a reason to really pay it back.

Jason: I think anybody who has a crude a substantial amount of debt, and I’ll say maybe like more than $30,000, but also maybe $3,000 is a lot to some people because some people just really are allergic to debt, which I think is a good thing. But it got to a place for me where it’s just the pressure of all of it was too much. I was just like, I can’t take on one more thing. Like, I’m at, like, $95,000 in total debt here. This is it. And that didn’t include your student loans. It didn’t include our car loan. So that’s why we always say $124,000, because with your student loans, that was that amount. We didn’t even include the car in that total debt number because it’s kind of like didn’t or the house. But yeah, I think when we came up with this debt payoff plan, it was a real turning point because I remember we had so many uncomfortable conversations about it, confronting it. I never wanted to log into any of these accounts.

Caroline: Oh, my God. Me either.

Jason: It was just like, set the minimum auto payments and don’t look. Eventually, maybe someone will come along and just pay all these.

Caroline: And just a quick aside about that, because I do remember being in this time in my life where the anxiety that you would have logging into your bank account because I’m going to see another overdraft fee or I’m going to see a number that I don’t want to see. And a big turning point for me about just ignoring it won’t make it go away was I think I’ve told this story too before, but I’ll just share it again, of I go down to Palm Beach to visit a friend for her birthday, and I don’t look at my bank account. And I wake up in the morning and we’re supposed to go to brunch, and I get a notification that I have an overdraft fee because I have $0 in my bank account and I have to ask my friend to pay for my brunch at her birthday brunch. And the amount of shame that I felt in that moment was just like, so awful. And I was just like, I’m not going to let this happen to me ever again. And so I knew that the only way to never allow that to happen was I have to work up the courage to check in on my balance more regularly because the only way that happens is if I just don’t look at it, right? And then I find myself in the worst possible moment with the worst possible balance. And so that could be, honestly, its own money decision in itself was to just start looking at the numbers, actually.

Jason: What I was going to say is I think we have a full podcast episode on it, but we definitely have a full article at wanderingaimfully.com/debt that basically outlines our entire debt payoff plan that we came up with and walks you through every step of the process that we use. And I think that the most important step in that. And I believe if I remember correct, like the number one step was we saw it as a game because debt comes with all of this negativity. It just feels so terrible to be in debt, and I’m sorry for anybody who that might be triggering to if you have debt right now because we remember what that feels like. I specifically remember losing sleep and just like, feeling terrible about myself. And there was this switch when we were like, no, this is like the original Donkey Kong game. We are Mario. We have all these people that we owe money to who are throwing barrels at us and they’re like, they’re trying to kill us, and we’re not going to have it. We’re going to jump over these barrels. We’re going to climb up the ladders, we’re going to grab the hammers, we’re going to crush this thing. And as silly as it sounds, making a game out of this in our minds of being like, this is not the end of the world to carry this debt. Let’s figure out a plan to work through it. And this is going to take years. And it’s just like Ramit talks about in this show, which I think is why we got so excited to record a podcast because we only talk about money, like, every couple of years in this podcast and in our articles is that it is just so important to change your mindset on it and to not let it weigh you down to then do nothing.

Caroline: Exactly.

Jason: Because that is the worst thing that you can do when you’re in that position because I was specifically in that position myself. I didn’t want to do anything. I wanted to curl up in a ball. I wanted to just be ashamed of the bad decisions that I made and then just, like, hope that something would swoop in and save me. And there was nothing to save me. What saved us was changing our mindset about it.

Caroline: Anything that you can do to get yourself in a mindset where you’re willing to confront it is absolutely the thing that you should focus on. So whether that’s treating it like a game, whether that is visualizing your like, as Ramit talks about in the show, your rich life every day and saying, this is what I’m going to be able to do finally when I get out of debt. Whatever it takes for you to get to that place where you’re excited to then go look at your numbers because you want to get that much closer to your goal, that is what you should invest your energy in doing step one because the mindset is like, honestly, the biggest thing.

Jason: All right, let’s get to number three, because it curtails nicely. So one of the things in that debt payoff plan that we started doing was weekly financial meetings.

Caroline: Yes.

Jason: Believe it or not, we weren’t meeting about finances at all.

Caroline: Yeah, I would say we were talking about it, but we had no idea.

Jason: When we were at Chili’s, we were like, are we going to be able to afford this or do we have to pay a credit card?

Caroline: We had no idea what we were spending our money on or we had no idea of what our shared financial goals were or anything. But because we both came together and said, the only way we’re going to be able to tackle this debt is by working together. And the best way to do that is to have weekly meetings about this and to come up with a budget and to look at our expenses. And eight years later, we still have a weekly budget meeting.

Jason: I can tell you, I can feel it in my bones, the uncomfortability of the first meetings.

Caroline: Oh, my gosh.

Jason: I hated acknowledging the debt. I hated seeing the negative numbers. I hated basically feeling like there was no way out of this.

Caroline: I hated the overwhelm. I felt jammed. My brain literally felt jammed when I would look at our bank accounts because I would be like, what am I supposed to do?

Jason: Yeah, it’s basically like someone dumping a huge pile of dog crap in front of you, like, way too big of a pile and then being like, figure out how to deal with this. And you’re like, no, I don’t want to deal with this. But you know how you start dealing with it is every single week you come back to that pile of dog shit and you start like, oh, let me grab a shovel and let me just start start moving it somewhere else. Let me start doing some stuff with it. Let me see if I can sell some of this. Talk to someone who wants…

Caroline: It’s taking a turn.

Jason: Is it?

Caroline: Yeah.

Jason: Okay. But anyway, it was horrible in the beginning and I will say that I think that’s why a lot of people don’t want to do…

Caroline: Of course.

Jason: Budget meetings and don’t want to do financial meetings, especially with their partner because…

Caroline: And you’re busy, right? Life is happening around you. You have so many things and you’re like, how am I supposed to make time for this thing that makes me feel bad? That makes no sense. But the truth is making time for that thing, first of all, it gets less awful the more you do it.

Jason: Absolutely.

Caroline: So after probably about the first two months where we were then in the rhythm of doing it every week, it felt so much less jarring because you’re desensitized to it.

Jason: There was not more money.

Caroline: There was not more money. I was like, here’s the… number’s still there. And it just didn’t hurt. It didn’t sting as bad because it was like we were getting used to it. And so I think that’s why I also believe wholeheartedly in weekly. Now when life… there have been times where once we finally did get out of debt, like last year, for example, while we’re traveling, we would do monthly because it was just like, life gets in the way and everything.

Jason: Yeah, I think you get to that place where you have figured out a system, you figured out processes. And again, our debt payoff article has a lot of those things in it that can help you kind of structure some of that stuff. But I do think that you wrote down here, which I think is a good point, is you can’t control what you can’t see.

Caroline: You can’t control what you can’t see.

Jason: And it’s such an important point that for those of you listeners who are in debt and unfortunately, the statistics just say that that’s a good amount of you because again, we were there as well. You probably don’t know how much your total debt is. And when you don’t know how much it is, you don’t know how much you need to work on it. You don’t know how much you need to put toward it every month.

Caroline: You probably don’t even know how much money is going towards your interest payments. This is what was the most disheartening thing to me and where I knew that we really had to do something drastic, which is what we did with freezing our cards and all of that, was the interest payments started becoming so expensive that it was just this snowball that was headed in the wrong direction. And I was like, we have to do something drastic. And that was when we froze our cards and just said, we’re going to live way below our means for a while.

Jason: Again, if you want that full debt payoff plan, I’ll put a link in the show notes and it’ll go through, like freezing the cards, calling credit card companies for hardship cases. We even heard Ramit talk about this in the show, which I thought was fun because not a lot of people actually know that you can do that. And it’s a very helpful thing.

Caroline: And I still remember that. I still remember pacing in the kitchen on the phone with the person, and they didn’t even do it.

Jason: I think I begged you to do one of these because I did like six of them.

Caroline: You did them all. I did one and I still…

Jason: And I just was like, I can’t do another one.

Caroline: Well, this tells you I still remember the one that I did because you were like, they’re going to… Just say, hardship case. And I did. And she fought me on it, and I fought her back because I was like, I’ve done the hard work of confronting this person.

Jason: Getting through the phone tree.

Caroline: Yeah, exactly. And so I was like, I’m not going to just abandon the ship right now. And so I really had to plead my case in terms of, like, I know that you have this available and here, and I was like, negotiating terms. And it worked.

Jason: Yeah, absolutely, it does. It saves thousands of dollars, like, in the grand scheme of things.

Caroline: And it was like, I stopped the snowball from rolling, right? Like, I at least could just stop it. And it didn’t change that it was still big, but at least it wasn’t getting bigger.

Jason: All right, we’re at number four. We’re about 50 minutes into this episode. We’ll see if this takes another hour. Number four on this list.

Caroline: Money is a juicy topic.

Jason: So much juice. But also, let’s not just do the juice. We need the fiber as well to counteract so our glucose doesn’t spike. I’ve been watching videos about sugar. Number four here, hiring financial advisors before we had any money. LOL. This seems like… and I remember how dumb it felt when we had the meeting with financial advisors.

Caroline: It felt embarrassing. I was like, Why are you here?

Jason: You’re like, I don’t have any money, what can you help me with? And that’s actually the point when they’re the most helpful because, when they can help you build a plan to get out of debt, and we had already had a plan, but they gave us a bunch of more helpful structural things, and one of them was this income flow, this account flow of how our money should flow between businesses having money come in to a household account, to a savings account. And again, this is in the debt payoff article, but I will say, seeing that was one of the most impactful things for us because, boy, did it feel willy nilly before that.

Caroline: And this was actually the entire catalyst for recording this episode because I think there was one episode in Ramit’s show where one of the couples were talking about how many accounts they had and they didn’t see how they fit together. And that’s actually what did the light bulb moment where I go, oh, my gosh, that’s something I take for granted now because we have this account flow. We know, okay, money comes into these accounts, then we transfer it to this household account. Then we use it to pay off these credit cards. We use it to go to our savings. We have a flow. Every month, it’s the same flow.

Jason: The flow was real slow in the beginning.

Caroline: Real slow, nothing was flowing. We hooked up the pipes and nothing was coming through the pipes.

Jason: Looked into the pipes, we’re like, hey.

Caroline: Hello, hello, hello.

Jason: Any money water want to drip out of here? Nah. Okay, thanks. We’ll be back next week. Tenha um bom dia.

Caroline: But I was watching that episode and I was like, oh my gosh, that’s something we take for granted. That if you don’t have that set up, it’s so overwhelming because you’re just like, random money is going into random accounts, and that’s why it’s hard to even pool it and pay it off towards your debt, right? So that was definitely a big thing that the financial advisors really helped us with, is just kind of understanding the flow of things.

Jason: Yeah. And I will say, just as a tip here, if you don’t think you can afford a financial advisor, some of them do work in, like, a fee based thing. And Ramit talks about it on the show of, like, it’s like 1% of whatever.

Caroline: But he says don’t do that.

Jason: But he says don’t do that. He says go for the hourly rate on paying someone, you may not have the money to go the hourly rate. So if you just have to go the fee based just to get someone to help you, you feel completely overwhelmed, I would say go for it because there are a lot of people who are maybe in the position that we were in 2013 where you just feel so overwhelmed by everything that having someone who charges a fee based on stuff can actually be the thing that is the catalyst to get you out. So it’s a little bit of just like, you don’t have the money to pay someone hourly, so you have to do something. So that can be an okay thing to do for a while.

Caroline: Right. And I would say even start by asking friends. I know money can sometimes be a taboo thing, but the reason we found those financial advisors was through a friend. And so understanding, I think one of the really vulnerable things about working with people to help you with your money is you also are never quite sure of who is taking advantage of you or who might be doing some shady stuff or like, I don’t know, maybe that’s just my own baggage I bring to it. But I’m always like, I don’t want to get screwed over, right? And so I think working with a friend, like going through a friend, so at least you have that little bit of built in trust where it’s like, well, I’ve been working with this person and I think they’re trustworthy. And that’s how we felt good about it. But that, I think, is really something to look into. And I know even some banks, I think…

Jason: Oh, yeah, for sure.

Caroline: At least a person you can meet with or at least have some type of financial literacy programming.

Jason: And again, a lot of these early decisions, like when you are in debt, it just takes a little bit of, like, tucking your tail between your legs and going, I’m not too big to go into my bank and say, I need to talk to a financial advisor. I’ve gotten myself to a place where I need someone whose job it is to figure this out. I need their help because my job is to make beautiful things on the Internet. And I’m good at that, but I’m not good at all the pipes and setting up all the money stuff. So let me actually work with someone who can do that.

Caroline: Yeah. So moving on to number five. So, again, ten money decisions that we feel like were good moves for us. Number five was setting up automatic savings withdrawals even when it felt like we couldn’t afford it.

Jason: Yeah. So this was something we definitely got from the financial advisors, which felt very funny at the time, which was like, you got to start putting away a little bit of money here or doing different things. And we’re like, there’s no extra money. And they’re like, well, you have to make the extra money carve off from all your other money, otherwise it never really happens.

Caroline: Yeah.

Jason: And I think this was really helpful because it created this account, which we ended up nicknaming the debt crusher account, which is really just a savings account, but it was where we would basically take, like, carve off as much money as we could. We were still paying minimum amounts on credit cards, but we would carve off, like $200 here or there, $500 here or there. A random tax refund comes in of $700 and you can put it in this account. And then you get to a place where you’re like, six months into this and you have $2,000 or $3,000 built up and you go, oh, we can pay off one of our credit cards fully. Like, we have one card that has $3,000. Let’s pay it off. And so we would kind of run those games and I think setting up the automatic savings and actually having these things accrue without us thinking too much about them.

Caroline: Well, because yeah, now I was specifically talking about… because I think you’re right, I think it was after we paid off the debt, but I was talking about specifically our life insurance account.

Jason: Yeah.

Caroline: Because that is basically worth…

Jason: That was going on while we were in debt, too.

Caroline: Well, that’s what I’m saying. So that’s specifically what I was talking about because it felt at the time like it was nothing in terms of I was like, why would we be doing this? And it’s stretching us even more financially to try to carve off this savings. But I can tell you, as someone who now, in the blink of an eye, it’s eight years later and there’s tens of thousands of dollars in an account that I didn’t even think about, you know what I mean? And so I just think your future self is going to thank you for putting aside that money today. And I know it’s like the classic cliche advice of any financial advice because of compounding interest and things like that, you’re always going to wish that you started ten years ago doing some of this stuff. But it’s true.

Jason: Yeah, absolutely. I do think my point here, though, is that we do have the automatic savings account, which goes into a whole life insurance account that basically accrues interest based on the stock market and things. It’s very technical. I’m not going to go into it. But in that…

Caroline: You can borrow money against it. Anyway.

Jason: In that automated savings thing. Like, we have that as an investment account, which also counts as a life insurance policy, which is helpful. But the other part of that, what I was mentioning is this debt crusher account. Again, it feels like money you don’t have to move to these other accounts, but you have to, you have to before you’re out of debt because it gets you into the habit so that when you start making more money, you don’t stop doing that. It’s just a thing that’s always been working behind the scenes for you because you’re never going to get, for most of us, a windfall of money to pay off all your debt. You’re just going to chip away at that big pile of dog shit with shovels and trowels and it’s going to eventually get to the place where you have a big enough shovel to get rid of the last pile that you’ve now gotten rid of it all. That’s how it works.

Caroline: Yeah. And even for example, I think it was four or five years ago now, we knew we weren’t going to have kids right away, but I was like, I would like to start saving for… again, as someone who had $0 from my parents to go to college, again, that’s not a shade on my parents, but it was really hard and it severely limited my options. I’m still so glad the way it all played out. But we’ve talked about wanting at least to have something. I still want our kids to have a little bit of financial hardship. I don’t want them to have it so easy.

Jason: We’ll definitely record some episodes on that in the future.

Caroline: But we started an account for them.

Jason: It’s very small.

Caroline: It was very small.

Jason: The goal was $200 a month. Basically, what we did is we reverse engineered and said in 20 years or 18 years is actually what it is, when our kids, or at least our first kid, would be graduating high school…

Caroline: Only the first kid gets the money. The second kid has to just figure it out.

Jason: But it’s basically like, how much would it cost every month to have $100,000 waiting for them at that age? In 18 years? It’s $200 a month with compounding interest. So that’s it. Like $200 every single month for 18 years. At that time, they will have an account waiting for them that they can decide what they want to do with it. And we’ll obviously help them.

Caroline: Or we can just take it out and just do whatever we want with it because now that I’m saying it out loud.

Jason: Maldives, Maldives.

Caroline: We’ll go to the Maldives. I’m like, you know, I think it’s character building for them to figure out how to go to college.

Jason: Well, no, and the way that we thought about that is not like, oh, here’s 100 grand. Do what you want. It’s like, no, put a PowerPoint presentation or a Keynote presentation.

Caroline: If you listened a couple of episodes about Jason’s presentation about the new podcast setup, you know we love a presentation.

Jason: And tell me about how this new revolutionary AI that does AI that does AI in 18 years is going to help change the world and how much money out of your account you need.

Caroline: I want to see a couple of slides on how it’s not going to eradicate humanity. Thank you.

Jason: Let me know how this is going to work. So, yeah, that is just something that thinking ahead a little bit. It’s not a ton of money. And I know for some people listening, because this was us ten years ago now, $200 a month is not money that we had. So we didn’t start it…

Caroline: We didn’t start there.

Jason: Ten years ago.

Caroline: But there’s probably another handful of you who maybe you’ve paid off your debt, and now you’re sort of like, okay, now what?

Jason: Or you’re getting close and you have a predictable income of some sort that you can carve off the money to start these accounts. So it becomes a separate thing. And now some of you might be saying, like, well, couldn’t I just take that money out of my full retirement account? And the bigger pile of money can amass and create more wealth through more interest. Absolutely, if you want. For us, we like things clean, so it’s like I’m actually fine to make a little bit less money with compounding interest to have a separate account that I just know this money is set away for this and I’m totally fine with that. Also, it’s a diversification play because…

Caroline: Totally.

Jason: That fund is total environmental friendly stocks, so it’s not connected to some of the bigger corporations of the world. Cool. All right, number six.

Caroline: Controversial.

Jason: Yeah. This is one where you have to be very… You have to have a Caroline in your corner because if you only have a Jason in your corner, it gets out of control real quick.

Caroline: That’s right.

Jason: This is playing the credit card points game.

Caroline: Yes.

Jason: Because if it were up to me, I would open 137 credit cards, I would hit every single minimum on them so that I could get every single bonus and we would have the most credit card points anybody’s ever had in their life.

Caroline: Correct.

Jason: Which is not actually how that would work out. But what we did find is that through a little bit of research, as we were paying down our debt and we were getting to this place where we said we can see the end in sight, let’s celebrate that we did this. We’re going to end up paying off our debt in three years, $124,000 in total debt. And then we ended up paying off our car right after that. Let’s treat ourselves to a money moon is what we called it. And so this was a dream trip. And so what we didn’t want to do, though, was then go into debt to go into this trip.

Caroline: Exactly. And as a side note, going back to what I said about whatever mindset you need to do in order to get excited about doing all this and doing the hard, emotional work of working through all this financial stuff, I think a money moon is like a great kind of carrot you can dangle at the end of all this. And again, don’t put yourself back into debt to go on this trip, but as a part of your payoff strategy, go, you know what? At the end of this, I’m going to take myself on a really nice trip. So for us, we decided to go to a dream destination, which was Tahiti.

Jason: Yeah. And what I found was we started talking about this and we were like, okay, how could we do this where we don’t have to spend $10,000 on this trip? Because, again, that’s putting us back in the debt game, which we don’t want to be in. So we started looking at credit cards and we found the Chase Sapphire card, which is like one of the best cards you can still get for travel rewards and credit card points. If we could meet the minimums, which we were having enough expenses to meet, we would get 100,000 point bonus in doing that. You can look into all this. Like Nerd Wallet has tons of articles on this and things like that. But what we found was I started looking into different resorts and places that had bonuses and whatever, and what I found was there was a specific hotel in Tahiti at the time. I don’t think it exists anymore with this perk, but it was basically like you would get 40% off of the nightly rate, plus you could apply points to the rate. So what ended up being we went for seven days to Tahiti. The total trip would have cost us, like, $7,000 just in the hotel alone. Ended up costing us one $1,200. This was, like, mind blowing that we could do this. And I remember looking at the numbers on the thing, I’m like, Wait, this is real?

Caroline: Could this be real?

Jason: How is this thing? And it’s like, I had to find the right hotel with the right discount that could also apply points. And now there are a lot more resources that can do this for you. So you can find these pretty easily. But that was super helpful because then that planning of that money moon didn’t become like we’re making a bad financial decision just to celebrate that we paid off all this debt. It’s like, no, we’re taking advantage of these financial things that we’ve figured out, and now we can treat ourselves and have a good time.

Caroline: And it is really tricky, though, because you have to be at the point where you know that you are living below your means, so that when you’re using the credit cards, you’re paying them off immediately. So I think it’s a good thing to use the credit, A, because you build your credit score, but you have to make sure that you know that you can pay it off at the end of every month. So it was a real mindset shift for us. I remember even it was scary to open up new credit cards after we had just gone through the shift in our mind of…

Jason: Half of our cards are in the freezer.

Caroline: Yeah, you freeze them, you do not use them. Debt is bad. Credit is bad. And we had to shift a little bit to being like, okay, now we’re in control. Now we’re in the driver’s seat. We can use some of these tools in order to have these amazing experiences, but it does take… The only way we’re able to do that effectively and not get ourselves back into a hole is because of those weekly financial meetings. We know our position. We know how we’re using this. We know we can afford it, all those things. So I just want to caution everyone.

Jason: Yeah.

Caroline: Make sure you’re at the right place in your journey to use some of these tools. But even to this day, it’s still a hot point of contention in our household because, if it was up to Jason, he would…

Jason: 137.

Caroline: He would game all the points, and I give you a lot of credit. We flew first class when we started our European trip last year.

Jason: First of all, business class.

Caroline: Sorry, business class.

Jason: We’re not at that level.

Caroline: I still don’t really know the difference.

Jason: We’re not the Ramit level. We’re at the…

Caroline: Our level. We flew business class for free was the trip from San Francisco over to Lisbon. So that’s incredible.

Jason: Yeah. Just on literally signing up for one credit card. And I actually thought it would be interesting to share when we were in our worst, worst, when we were in our lowest place financially and in debt and all these credit cards. I think we had, like, 15 credit cards. I think I had, like, 13. You had two?

Caroline: Yeah. My mom always taught me.

Jason: You had a hidden Best Buy card that we stumbled upon.

Caroline: We did.

Jason: There’s no shade. I had, like, 13 credit cards. No joke. So basically between us, we had, like, 15 total cards, and we had to stop using all of them and then focus on one card to rule them all for me and one for you, and that was it. And so we barely used credit cards at all until we paid everything off. And of course, sometimes you need to use credit cards for certain things or bigger purchases or whatever, but we really tried not to use cards at all. When we finally paid off our debt, we had all these cards that had nothing, no balances on them. And so then it was really surveying, like, well, what cards actually are beneficial? Because a lot of these are not. Like, a Best Buy card. Not beneficial. Random Citibank card that I signed up for, like, eight years ago. Not beneficial. So then it was to look at the landscape. And again, this is where Nerd Wallet, all these other sites do such a good job of doing this to then look at, like, okay, well, what perks would we actually use? And that’s where the Chase cards are really good. We actually signed up for four Hilton Amex cards, which helped us pay for our trip in Greece, like, our entire stay for that. But again, all of these cards that we signed up for, we would meet the minimum spend, and we would pay them off immediately. So it was never carrying a balance on these cards. It was just to get to the end of the points road, earn the points, and then just be done using the cards.

Caroline: Yeah. And the thought there is, like, these institutions are doing their best to take advantage of plenty of people, and so it’s like…

Jason: Take advantage of them a little bit.

Caroline: Fight back a little bit.

Jason: I did want to say, so I actually checked, I think we have four debit cards, but total cards we have now is 19. But it’s funny if you think about it, how many cards do you think we actually quote unquote use?

Caroline: Yeah, like five.

Jason: But even at most, right, it’s really like, two. But we’ve used them all for their perks and now they just kind of sit, and sometimes we’ll close some of them down and sometimes we’ll just leave them open.

Caroline: Yeah, we do, like, an audit, like, once a year, like a bigger…

Jason: We’re coming up on needing to do it this summer.

Caroline: A bigger audit where we go, okay, what do we need to shut down? And whatever.

Jason: And I do think there’s a lot of, like, credit card, your credit score and all that that comes into these decisions. And I think some of it is just like, if you’ve gotten out of debt and you’re opening cards and closing cards or whatever, I don’t think it’s that big of a change or a worry. So it’s more just play the game the right way and make sure you’re paying off your cards.

Caroline: Great.

Jason: All right.

Caroline: Number seven. Okay. Another controversial one.

Jason: Oh, wow. Okay. What other one was controversial? The joint accounts?

Caroline: Yeah.

Jason: Okay, got it. So this one’s related.

Caroline: Related. So number seven is deciding not to have a wedding.

Jason: Yeah.

Caroline: We did that. And it wasn’t entirely financial, but I will say a lot of it was. So we decided to get married at the beginning… We made the decision at the beginning of 2017. We ended up getting married in March of 2017. So one benefit of not having a wedding is it only took three months to plan an elopement.

Jason: It really didn’t even take that long to be honest.

Caroline: Didn’t even. But I remember. So there…

Jason: There’s a lot there.

Caroline: There’s a lot here.

Jason: Yeah.

Caroline: Okay. We were aligned on a lot of things as it relates to having a wedding. Those things were, number one, we both have an instinct to reject doing things just because you think you should. Number two, we were not in a financial position where spending $30,000, $40,000, $50,000 on a party felt like a smart thing for us to do.

Jason: Especially, like once you get out of debt, you start to realize, like, why would I spend $30,000 on this when I can spend that $30,000 on a lot of other things? And I get it. This is the most memorable day of your life.

Caroline: Well, and here’s that’s the other thing I was going to say is, for us, I know a lot of people choose that because it’s worth it to them because the pros outweigh the cost, right?

Jason: Sure.

Caroline: For us, the cost felt so high and the pros just weren’t there because we don’t like gatherings with a lot of people. I didn’t want the pressure of, like I just knew… Most people, I think, like weddings because it’s like every person. That you care about and your family…

Jason: It’s all the dynamics.

Caroline: And I was like, Are you kidding me? I’m not even going to be able to focus on myself because I’m going to be thinking about, like, are those uncles talking to that person and those friends? Where does that person sit? HSPs, you’ll get this. That’s a nightmare of managing the energy of all these people and not just strangers, but people you care immensely about. It just was a bad idea. Number three, I hate things where all the attention is on me. The idea of walking down an aisle of people looking at me and me trying to smile, and it makes my skin actually crawl. I hate it. And so it just didn’t appeal to me in any type of way. And I didn’t want the stress. I didn’t want you and I to fight about it. It’s just nothing about it was appealing. And then also from the financial side, we were just getting to the place where we were… I can’t remember how. We definitely paid it off, but we…

Jason: Oh, yeah. No, in 2017, we were profitable because we were just starting to do Buy Our Future, which is where my Buy My Future project was in 2015, which really finished off our debt.

Caroline: So things have really had an inflection point.

Jason: So we were actually, like this was, again, like, in the macro sense of our income, we were, like, back up again.

Caroline: But we had just gotten back up, so I think we went to Tahiti in late 2016, maybe?

Jason: No, we went to Tahiti in 2017.

Caroline: I don’t think that’s right.

Jason: Okay, well, we could go back and look at the receipts.

Caroline: You might be right. I’m not confident. 50% confident. But the point is, we had just gotten to the place where we were like okay again. And the last thing that I wanted to do was to not be okay.

Jason: I think the wedding thing is it’s such a personal decision for everyone to make. But I know for me, when we started to really get serious in our relationship, it was always the thing that was looming for me because it was the thing that forever in my life, I’ve always just been like, I don’t want this. I’m not interested in this big gathering. I’ve been to plenty of them. None of them seem as great as they look on the photos afterwards. And, like, I get it. That’s totally fine, but I don’t want this. I want something else. I want something different. I want something that feels like it’s like, what’s my dream? And this is like going back to Ramit Sethi. What’s your rich life? My rich life version of a wedding is like standing on a cliff, cheersing some tequila, having some donuts with, like, the person I love, with zero stress.

Caroline: It was zero stress.

Jason: Absolutely. And that’s exactly what we did.

Caroline: Yeah.

Jason: And it’s so amazing to look back, and we’ve talked to so many married couples who’ve been like, I wish I would have done it your way. And again, that’s not to say that the way that we did it is the best way to do it. I’m just saying that there’s so much, I think, societal pressure to get married and have a wedding and do these things this way.

Caroline: My ring was $200.

Jason: Yeah. I mean, even those decisions alone, right? Like, we picked out our wedding bands kind of, like, together, and I found this guy on Etsy who made these, like, half wood.

Caroline: Yeah, your ring was from Etsy. Mine is from a local person in San Diego. I will say the one thing I wish I would have spent more money on, and I’ve told you this before, I wish that I would have actually allowed myself to spend money on a dress that I loved with all of my heart.

Jason: I love that dress, though.

Caroline: I know.

Jason: I know you don’t, but I… yeah.

Caroline: No, I don’t dislike it at all. I love it. There’s a lot of things I like about it, but I didn’t love it. And for someone who I’ve never really allowed myself to buy clothes that are even a little bit expensive.

Jason: Right.

Caroline: And I wish I would have allowed myself that one, especially because it was like there was no other part of it, and it’s not like I look back at the photos, and I don’t like the dress. I like the way I look. It’s more important to me, like, the experience we had, and there’s everything I like about it. I just wish I would have allowed myself that one indulgence of being like, if you’re not going to pay for any of this, give yourself the one kind of splurge. I just wanted that one moment of feeling like, man, I love this dress, and I’ll keep it forever. I mean, it turns out it’s probably best that I didn’t because we moved and sold our stuff and whatever, but I just share that because there’s both sides of that coin. It’s like they’re saving money, but there’s also times in your life where you’re like, man, I really wish I would have let myself on a little bit of more freedom to spend money on something that I really cared about.

Jason: Yeah, well, that’s the only decision that you can make.

Caroline: Yeah. And I think if we ever do some type of… I couldn’t see us doing, like, a… I could see us doing another sort of, like, vow renewal, elopement type of thing. I don’t think we’ll ever have a big party, but if I do that in the future, I could see giving myself that gift of having a really…

Jason: Extravagant dress.

Caroline: Not extravagant, but just, like, something that feels really special and unique and one of a kind. The dress I got was at, like, Nordstrom, I think. That’s nothing against Nordstrom at all. It’s just like, there was nothing that was like special about it.

Jason: You can go to Marshalls, and there’s nothing wrong with Marshalls either.

Caroline: I could have gone to Marshalls.

Jason: All right, number eight here. We have three left. The decision to combine businesses.

Caroline: Yeah. Okay. So also, I like this setup. I think I heard Remit say this on a podcast as well, of, like, there’s three skills that you need when it comes to money. One is spending money. That’s a skill. One is making money. That’s a skill. And one is managing money. That’s a skill. And I really liked that framing because I think all of our decisions here hit on each one, but this one is about making money. So decisions that we made that are in the category of making money.

Jason: Yeah, which of these do you think I’m best at?

Caroline: Spending.

Jason: Yeah, which are you best at?

Caroline: Making.

Jason: Okay, cool.

Caroline: Yeah.

Jason: Great. Yeah, cool. Yeah. I mean, I remember in 2017, so this is again, things are going pretty well. You still have Made Vibrant. I have Jason Does Stuff. But I’ve got my Buy My Future project, which turned into Buy Our Future project, where we kind of created this combined thing, and that was going well for us financially. But I just kind of felt this itch that there’s so much crossover. It’s going to make it easier if we just combine everything.

Caroline: It honestly felt kind of silly because I was also hitting this sort of cap where I was comfortable and it was enough, and it was great, but it was sort of like I could see this ceiling of me just trying to do everything myself.

Jason: Right.

Caroline: And you were seeing the fact that we were doing actually a lot of the same things, building an audience, writing content, talking… And the things that we would talk about were even overlapping, where it was like, you would talk about business stuff, and then I would talk about sort of personal growth things and creativity, but then you would talk about creativity and marketing, and then I would talk about marketing. And so pretty soon, it was like, we’re doing the same thing. We’re talking about the same thing, just in a different voice. And then you saw the writing on the wall, and we’re like, I think this is one of those rare instances where one plus one equals three. We should just come together, create something that’s bigger than us, and use both of our voices and use both of our audiences. And I think it would raise that ceiling that both of us are being limited by into something much bigger. And you were right.

Jason: Yeah. I mean, if you look back at it just from, like a top level financial perspective, 2017, as a household, we’re probably making am I allowed to say?

Caroline: Sure.

Jason: We’re probably making $300,000 total as a household, two separate businesses, a lot of juggling of all the tasks, and nowadays we’re making about double that. And it didn’t start that way. Right. It started $1,500 a month. That’s what we were making when we combined our businesses and started over from scratch.

Caroline: Yeah, exactly. So imagine going from $300 to then going to, like…

Jason: $1,500 a month.

Caroline: Exactly.

Jason: And there was extra money, like, Teachery still existed there, and it was still what have you.

Caroline: But the most important point that I want to hit home is that we had to take a huge drop in order to then exceed the ceiling.

Jason: Yeah. And I do think that those are the money decisions that you sometimes make that feel scary and they feel like there’s a lot of unknowns. But you just have to trust your gut and your instincts, and you also have to know that, like, okay, yes, we’re starting over, but we are starting over with a lot of things at our disposal that are helpful. So we had two email audiences that we combined into one. Granted, a lot of people unsubscribed in the beginning because they just didn’t want both of our voices in a newsletter. That’s fine. We had other products that we shut down, we stopped selling and putting attention toward that. We’re making money, but we didn’t want to focus on those anymore. And so it takes that risk, that chance. And this is what entrepreneurship is to me. It’s these moments in time when you go, I’ve just had this hunch that this is going to be better. But I also have a long term vision of it’s not going to happen overnight.

Caroline: Right. And I’m going to have to have… We call it the short term squeeze for the long term ease. I’m going to have to have a squeeze for a year where maybe I’m pivoting my audience or maybe even you’re listening to this and you’re like, I need a career change. Like, I’m going to leave this sector to even go back and go back to school so that I can then earn more. Right. Or, like, whatever that is. I’m going to leave this big company where I’m safe and I’m going to start my own thing, and it’s going to be a pay cut in the beginning, but I know that my potential is so much greater. Sometimes it’s those decisions where you know you’re taking a step backward, but you know that the potential is then so much bigger. And I’m just so glad that you saw that. And I’m glad that I took the risk with you.

Jason: Yeah. It only took, like, 183 walks.

Caroline: Well, you should have showed me a presentation.

Jason: I should have. I wasn’t doing Keynote at that time.

Caroline: You were not doing Keynotes at that time, but that would have been so effective.

Jason: Well, the walks were nice, though.

Caroline: The walks were very nice.

Jason: And also I was gung ho in it, but I still had my own apprehensions as well. All right, number nine in our list here of money decisions are money multipliers.

Caroline: Yes. So I think Ramit talks about this idea of a money dial, and I don’t know if this is the same thing, but this is just a name that we came up with a long time ago, which is these things that if you spend money on them, they actually, in the long run, make you more money. And so for us, that is things that give us time and convenience. The biggest examples that I can think of for this, and I don’t know how we just knew this early on, but a big one is meals. So we have been getting prepared meals delivered in some capacity since…?

Jason: 2014.

Caroline: 2014. And I don’t mean like a meal box where the ingredients… that might be helpful for sure. I mean, physically a meal that you just heat up.

Jason: Fully cooked.

Caroline: Fully cooked. And maybe we’ve talked about this before, but this has worked really well for our lifestyle for a number of reasons. First of all, we love work and we didn’t like the fact that going to the grocery store and taking the time out to meal plan and prep and make all these meals. That was taking so much time and breaking up the day. And it wasn’t an activity that we enjoyed. And so we were looking for solutions to that problem. And then also we just would never do it because we didn’t like it. And then we’d eat out more, and then we’d spend more money and then we’d eat more crap. And so this was an investment in our health and in our time, getting our time back so that we could actually pour it into the business, which eventually then makes you more money.

Jason: Yeah, I remember doing the math on this and it was basically like 8 hours per week we saved by doing prepared meals. So it’s like, well, what’s our time worth? And so you start to think about that, you’re like, well, there’s an exponential rate of return on our time. These 8 hours that we’re investing in making food and going to the grocery store and thinking about food and decision fatigue and then making bad decisions, that’s a negative net return on our time. This isn’t extravagant. I know I’ve said the price before, but essentially what we pay now is about $150 per week for our meals. So it ends up being $600 per month for our prepared meals. And that takes care of 90% of our food every single week. And that means we go to the grocery store. Now, we go to the grocery store more in Portugal because food expires much faster here. Like a cucumber lasts like two days in the fridge, which is wild. So we are going to the grocery store a little bit more, but it’s much smaller trips. And even before that, it was much smaller trips just to stock up on the things to cover the other meals. So I will say, some of you listening to this probably spend less than $600 a month on food for your whole family by just going to the grocery store. And maybe you like cooking and maybe you like taking the time out with your family to come together to make a meal and do all that, then by all means do it. But for those of you who might be like us, where you love food, but you don’t love all the hullabaloo of making food at home, lunch and dinner and breakfast and all those things. Maybe think about doing prepared meals for 30% of your meals or 50% of your meals, and it will just save you time. And it may seem like, oh, I’m upping my food budget a little bit, but look at it from the perspective of what else can you be doing with that time, if nothing else? Not doing anything. So it’s just getting that time back and not having to worry about it.

Caroline: For not even work right. For other things in your life that you want to put your energy and time into. And we’ve done it for how many years now? And we still regularly sit down to the table with a delicious meal that took 10 seconds to heat up, which we’re usually doing in the skillet. Sometimes we do do the microwave.

Jason: Microwaves aren’t bad. Listened to a whole podcast episode.

Caroline: I know, but I love doing it in the skillet because it gives me the illusion that I cooked it, which I did not. But we sit down and I go, Best decision we ever made.

Jason: Yeah. So the meals are a really good one. Also, if you’re curious how to find those, for those of you in the US. Go on Yelp. Search, prepared meals. Very easy way to find them. There are tons of different services that we’ve tried over the years that pop up outside of Yelp as well. For those of you who are outside of the US, maybe search Google Maps. That’s how we’ve found the one here in Portugal. They actually are in Lisbon. They’re the only prepared meal company I found. But they deliver it to where we are, and they are fantastic. They’re some of the best flavors we’ve had.

Caroline: The best.

Jason: In nine years. The other money multiplier that I wanted to mention was laptops.

Caroline: Yes. Technological devices.

Jason: Yeah. This would just be computers, iPads, phones. I think there’s a big difference between just upgrading to upgrade and upgrading knowing that that’s going to make you more efficient at your time. So, for me, as someone who right now, it’s only editing our monthly coaching session, but the laptop upgrade that I made from the previous version, which is what you have to the M1 max, when that came out, it literally cut my replay time for our coaching sessions in a quarter. So I went from having to spend 10 hours on that to spending two and a half hours.

Caroline: Now, tell people why. Is it because the uploading of the footage, the rendering?

Jason: It’s the rendering, all the rendering. So it’s literally bringing all the footage, and it does it all, like, 75% faster. So that in itself was just, like, fantastic for me, but then it’s also in everything else. I know some of you listening to this have an older machine of some kind, and you have to wait for things to load or it feels really slow. And it’s like, I know that you might not be in the position to feel like you can afford the next device or an upgrade to it. In that case, it’s like you need to squirrel away $50 a month to build up to do it because that’s what we started doing.

Caroline: Or here’s the beauty of making money. You go, how much is that going to cost?

Jason: Right.

Caroline: Can I do, like, one consulting call and try to cover it? Get creative and be like, okay.

Jason: Flash sale of my online course.

Caroline: Exactly. And then all the money is going to go towards investing in now this money multiplier that’s only going to give you your time back. That’s the type of creative thinking that I feel like, going back to the very beginning of this podcast, the day that we decided that we were going to treat the debt crushing like a game, it started to open up this whole new mindset of like, okay, now everything’s a game. Now everything’s a creative exercise. What do I need? Where am I trying to go? How can I make more money with the skills that I have? How can I provide value to people in exchange for money? You start to see those opportunities everywhere.

Jason: I just remembered while you were saying that how this whole upgrading technology thing started for me. My nine to five job, I got handed a laptop. When I started, I was a graphic designer. It was an IBM ThinkPad with the little red knob in the middle. And I remember little thingy, I remember going into my boss one week. I’ve been working there for one week, and I was like, I cannot work on this machine. I need you to buy me a MacBook Pro.

Caroline: Really?

Jason: And they’re like, $4,000. Especially at that time, they were super expensive. And he was like, no way. I was like, I guarantee you I can do 100 times the amount of work that this crappy machine can do on that machine. And if not, I was like, I will pay for it in my paycheck. I can’t work on this.

Caroline: You’ll be amazed at how much more I made.

Jason: I remember when I got it, the amount of output that I could do and the comfortability that I felt. And I didn’t even have a Mac at that point. Like, I didn’t have one at home. And I remember having a meeting with him, like, a month later, and he was like, you were correct. And literally, they went, like, all the design people around there, they ended up buying Mac computers for them.

Caroline: Buying them for them.

Jason: Because I was the person that basically ushered in, like, there is better technology to do than what we’re doing, because it would take, like, ten minutes to just open Photoshop. That’s not an exaggeration. It was so slow on those machines.

Caroline: Well, that’s such a good point of that’s an Illustrator of it is a money multiplier, right? Yes, you spend this now, but what you get out of it is so much more.

Jason: Totally. Like the amount of folks listening to this who might be frustrated with a device that you’re currently working on to get your work done. Imagine not having that frustration and instead replacing that with joy to work on your thing because you can actually get it done faster is going to allow you to do more things. And again, I know it’s coming from a very privileged position of saying, like, oh, well, you just go buy a new laptop. But it’s about creating a plan that you might buy one in a year, but at least you put a plan in place right now to be able to squirrel away the money to do it, or in a month, by setting up a flash sale of a thing or whatever.

Caroline: Well, that actually brings us to our last point, which is related. And this is less, it’s another point that is related to spending money, but not for the purpose of making more money. It’s more about spending money on things that enrich your life. And it kind of ties in the whole idea of what Ramit’s show is about, which is creating your rich life. And what does rich mean to you? It doesn’t mean how much money in your bank account. It means a life full of the experiences that you want, of the feelings that you want, and the values that you care about. And so for us, spending more money than what I would say is the average person on where we live and travel are two things where I still remember to this day. I remember having lunch with a friend of mine when we were leaving Florida and we had just decided to move in with another couple and moved to California. And our rent on that place was certainly more money than our mortgage was in Florida. And it was more money than I had ever spent on a place that seemed absolutely… I told her how much and the visible look on her face, I think she was probably paying like $600 a month to share an apartment at the time. The look on her face was like, are you sure you know what you’re doing? This doesn’t seem like a good idea. And I’ve taken… that expression is like seared in my memory. And I still think it’s probably how people would think about what we spend on housing and renting. But I just sort of smile to myself because there’s nothing that we spend money on that is worth it to me more than the place that we live, other than maybe travel. And it’s because we learned a long time ago, I think we learned originally with that moving from Florida to California, that for us who work from home, who spend 95% of time at home, where we live matters so much.

Jason: Yeah.

Caroline: And actually there’s studies now that show like, geographically even, where you live matters to your longevity because of the choices of people who are around you, the people you’re surrounding yourself with, the amount of fresh vegetables that are available to you, the restaurant options available to you. Studies have shown this. And so it’s not just the geographical region, but it’s the region and it’s the house itself. We will always pay more for that because of what joy it brings to us.

Jason: Yeah, we’ve had multiple conversations over the years of, hey, should we just downsize to something like, super cheap for two years and just bank all the extra money and just build up our savings, like a ton and just like, whatever. And we go back and forth, we go back and forth and we go, no. I’m literally not willing to give up two years of happiness to live in a place that I wouldn’t love living in because I don’t know if I’m going to die tomorrow. And I know that that is, like, a very short term way to think about life, but this is one of those areas when it comes to money that I’m like, if I died tomorrow, I’d be like, great, I picked a wonderful home to live in in my last days. And I’m just saying that we made that decision when we could barely afford it, and we had a plan, so we knew that we could afford it.

Caroline: That’s a caveat, right? It’s not like you’re living beyond, but it’s just like you’re spending more of your percentage of take home pay than probably the average person on housing.

Jason: Yeah. And now we are at the place where and again, this is part of moving to a country like Portugal. Things are a lot more affordable here than they were in Southern California. So it’s like we get a lot more for our money here than we would there. And we’re now living in a place where it’s like we can easily afford where we live. And it happens to be like, an amazing place that brings us a lot of joy. But we wouldn’t have gotten here had we not gone from the leaving Florida to move to California to then moving California to moving here.

Caroline: But this is also where I think it takes a tremendous amount of self awareness because a different person might actually decide that it is worth it for them to live in a place that is a sacrifice for the short term because it doesn’t affect them that much.

Jason: Absolutely.

Caroline: But for us, it affects us so much. And then I’ll also say because we’re in the position where the making money side of the equation has sort of an infinite upside, right?

Jason: That’s just entrepreneurship.

Caroline: That’s entrepreneurship. You’re not on a salary. You’re only bound by your ability to build a business. And so because that potential is there, I say to myself, let’s quantify it. For every notch of happiness that I go down, my ability to then cash in on that potential goes down as well.

Jason: Absolutely.

Caroline: And so I view it almost in a very practical sense of going, okay, if I prioritize my just environmental happiness, it’s also an investment in my own productivity, and not all of it has to be so cut and dry. I don’t mean to make it that way, but just walk with me here and viewing it in this very practical sense. For every notch I go down in happiness, because I’ve decided that I’m going to move into a place that’s maybe, like, three quarters of the price instead of the price that we have now.

Jason: Has no windows.

Caroline: Yeah. Like less of a view or like…

Jason: No, just no windows.

Caroline: Oh, no windows. That is also then decreasing my potential to earn more. And so does the math actually work out? Do you know what I mean? For me, the math works out more to go, I love where I live. I’ll pay a little bit more for it because, for every extra dollar I spend on a premium house, for example, I get ten times the amount of potential that I can make because of how much happier I am.

Jason: Yeah. And I think that this is such a hard one to quantify, which is why we put it at the end, which is like… And again, we couldn’t do this ten years ago. So the reason we’re sharing this now is it got to a place where we had built the debt payoff plan. We had everything moving. We froze all the credit cards, we reorganized our businesses, we worked with financial advisors to come with everything, and for two years chipped away at our debt, and then saw the opportunity to move to California to go, okay, we’re not out of debt yet, but we have a good plan in place. We can afford to take on this higher rent, and this might be the opportunity for us to start a new life. And really, that’s what it was.

Caroline: It was.

Jason: We spent money to start a new life.

Caroline: It changed our lives.

Jason: And it changed everything. And I do believe that also coming here to Portugal is another version of that. And truthfully, last year, traveling full time was the start of that.

Caroline: Totally.

Jason: And it’s a different chapter of our lives. But I think there’s a very interesting trajectory in just watching our overall top line revenue throughout our lives of where it started and where it is now, based on the decisions that we’ve made to follow some of these curiosities and to push a little bit the boundaries of spending. And again, we’re not talking about, like, $10,000 a month rent here. It’s a reasonable amount of money. It’s on the high end of reasonable, but it is an amount of money that we can afford it, and it is providing us the value to then come up with creative ideas, love the place we live, feel joyful every day when we wake up. And I just want to share that because ten years ago us did not feel that way. We didn’t enjoy where we lived. We didn’t enjoy the town that we lived in. We didn’t like going to Chili’s anymore.

Caroline: The Presidente Margaritas were not doing it.

Jason: They ran out of them. But it just… The ideas weren’t coming. Everything came to a standstill, and we needed a fresh start. And so using money as a lever to pull to create that fresh start was something we just saw the long term vision for to be able to do that. So, yeah, I hope that these ten things were helpful and maybe just like one you take away from this.

Caroline: Or just interesting. I mean, I don’t think we have enough conversations about money. And I was really scared, honestly, to do this episode, because even I… when you share the way that you think about money or the way that you spend money, it opens you up to judgment, it opens you up to criticism. And I just thought to myself, well, do I want to live in a world where more people are talking about money or, like, less? And so I hope that by being transparent, even if it’s just a handful of people who go, gosh, it is possible. It is possible to change your relationship to money. It is possible. I felt when I was watching this show, I felt this overwhelming sense of gratitude, but also responsibility to go, wow, I can’t believe… We don’t get here in life…

Jason: We are living a rich life, like, if we’re just being honest.

Caroline: And I just thought, I want that for everyone. I want every single person to not have to worry when they go out to dinner, or not have to worry when they go buy clothes for their kids, or not have to worry. And so it’s like, I just want to share some of those inflection points along the way and some of those decisions that we made that I feel like did start to snowball in our direction to where now it is a snowball.

Jason: Yeah. And I hope that there’s one singular person of our 24 listeners that listen to this that goes to that debt payoff article because they are in debt. They do our ETAC Exercise, which is our expense tracking. They start a weekly budget meeting. They build an income flow. They have a whole debt payoff plan that takes three to five to seven years. Three to five to seven years from now, that person has paid off all of their debt and they’re making decisions like we’re talking about now.

Caroline: And they go to Tahiti.

Jason: And they go to Tahiti.

Caroline: On credit card points.

Jason: And they move to Portugal. It’s just like, whatever that version of that is. I just hope there’s one person that listens this that feels like their debt was overwhelming, but now it feels like a game to be won, and that game is going to take years to play again. You’re going to lose me for the rest of the year to TOTK. We’ve talked about this. I’m going to be on the couch playing Tears of the Kingdom. But in the silly metaphorical game of paying off your debt, it does take years. You hear this in the show. You hear this from real people like us who have gotten out of this, but that’s what it takes. And so if you can just opt into that game and just see it as a game that’s going to take a while…

Caroline: Also, as the people who are now years removed from it, I go back and go, was three years of our life worth it to live the life that we live today? A million, trillion times over.

Jason: Yeah. And what did we really have to do during that time? We made some sacrifices. We didn’t eat at Chili’s anymore. We didn’t go to the movies very much.

Caroline: I did go to Marshalls.

Jason: You did go to marshalls.

Caroline: And I found a lot of cute stuff.

Jason: Yeah. All of our spending came to a screeching, a halt, and we lived as strictly as we possibly could by setting budgets and sticking to them and just making short term sacrifices to do that. But it was all worth it. It was 100% worth it. So, yeah, that’s our episode on these money decisions. We really hope you enjoyed it.

Caroline: And if you have any follow up questions, email us because maybe we will do a money episode in the future. I don’t know.

Jason: Yeah, I think it would be fun to talk about just the way that we invest money because we do have an article on that…

Caroline: I don’t want to talk about that.

Jason: On our website.

Caroline: Because I don’t know what the hell I’m doing.

Jason: Well, yeah, but I think we have a couple of interesting ways that we think about it in regards to Teachery and things like that, like long term thinking that are kind of different from normal societal things. But no matter what, hope you enjoyed this episode. We appreciate you listening for this one. It was a long e, but that was a goodie.

Caroline: A longie but a goodie.

Jason: Long e but a goodie. Feel free to leave that in the Apple podcast reviews, you know. Love this podcast.

Caroline: It’s a long e, but it’s a goodie.

Jason: All right. Podcasts are cool.

Caroline: Dot, dot, dot.

Jason: Nicely done, babe.

10 Impactful Money Decisions We Made

(Big Fat Takeaway)

Money decisions are scary because of all the unknowns. It's important to learn more about money, talk about money, and do what feels right to you.

IT IT

This article written by

Jason Zook

(he/him) Co-head-hancho of this WAIM thing. I used to wear t-shirts for a living, now I just wear them because I'm not a nudist. You can usually find me baking things, watching JCVD movies, and dreaming of living on an island.

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