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A
So today we are diving in to spending more on vacations. Now, here's one thing that we want you to know here on your next dollar is we want you to enjoy your money and we want you to spend more on the things that you actually value. And so that is why this episode is going to be so exciting and one of the most fun topics to talk through. Most people out there won't tell you that they'll say, hey, save or hoard some of your cash, but we want you to spend more on some of the things that you love. So today in this episode, we're going to be diving into how much should you spend as a high earner? A lot of high earners have the question, am I spending too much? Am I spending too little? But we're going to be diving into how much you should be spending as a high earner. We're going to talk through some of the financial boxes that you should consider checking off before spending those dollars on a vacation. Obviously, we don't want to go on a vacation and never be able to retire, so we want to make sure that we are checking off some of those boxes. First, we're going to talk about how to cut spending on some of the areas on your vacation that you could care less about and spending more on the areas that you actually care about, plus the percentage of your gross income that you can consider spending on a vacation. Now, some of you may feel as though this percentage is pretty high. Some of you may feel as though, ooh, this is less than what I actually spend right now. So that's gonna be a fun portion that we'll be diving into. And the trips that you should take in your 30s and 40s that may be much more difficult to take as you age. And how to prioritize some of those Fountain of youth trips that we'll be talking about today. Plus, we'll be diving into how to think about a vacation. When it comes to family experiences, what are the most valuable places that we can spend our dollars going forward? So in this episode, we're going to be diving deeper into all of those different things. And in addition, we're going to have a new segment talking through and ranking some of our favorite ways to vacation. So I am really, really excited to dive deeper into this episode. Welcome to your next dollar powered by Nerd Wallet Wealth Partners, the show where we teach you how to be wise with the money you already have today while saving for your financial future. I'm Andrew Giancola, and today I am so excited to be joined by Ryan Sterling, who is the CEO of Nerd Wallet Wealth Partners and a financial advisor. Ryan, welcome to your next dollar.
B
Thank you for having me. It's good to be on.
A
I'm so excited to have you here too. And we're going to dive into and kind of show the listeners some of the cool things they can do with vacation. So let's first go into figuring out what you need to be doing first before you even take a vacation.
B
Okay, so first off, huge, huge, huge fan of taking vacations. Right. I'm a big traveler myself. I love to travel. I love to help clients plan their next destinations. But before we're talking about taking that big trip, you gotta have some things in order. Number one, like if you have credit card debt, we gotta wipe out the credit card debt. That will also allow you to enjoy yourself on vacation because you won't feel guilty that you're going into more credit card debt. So first and foremost, wipe out the credit card debt. You also need to really start paying yourself first having that savings trajectory to make sure you're building up that emergency savings fund. I would also say too, that, you know, if you're working at a company where there's a 401k match, make sure that you're able to make the contributions up to the match because you're saying no to free money. So there is some housekeeping in order. Again, credit card debt, pay yourself first, build up your emergency savings fund. You know, make sure again that you're at least getting the employer matching your 401k. Those are table stakes. Like we have to make sure.
A
Sure.
B
Like that is all in order before we start the process of planning for your next dream vacation.
A
And those are some really important points. And I think for most people out there, noting that you got to have some sort of order of operations before you dive into making this decision is really, really important. So when you're thinking about, you know, covering some of those line items up front, we want to make sure that you actually have the cash on hand. You always pay for vacations in cash so that you can actually cover all the costs for that vacation. So it's very, very important to think through that. Which leads us into our next point is sett vacation number. So figuring out how much you're going to spend on a vacation is not going off of just what you've seen on Instagram. Listen, I know those huts that are in the middle of the water right there that have the swings where it looks like you're swinging on the Caribbean. Those look amazing on Instagram. But if it's not in your budget and you have not set the parameters to go out and actually spend the amount it takes to go on that vacation, it is not worth it. It is not worth it risking your financial future to go on vacation. So we want to set the number that makes sense for, for our financial situation. And here's the beautiful thing for high earners is you have disposable income available, and if you value vacations, you can spend more on vacations. This is one of the coolest and most powerful things that comes with having a high income. This is something that I personally truly value is I love going on vacations. I love spending more on experiences. I love spending more on memories. And so I came up with just a couple of different ways that you can think about this. Now. You can consider spending this amount on vacations, but making sure it still fits in with your overall financial plan. So 5 to 10% of your income is one of the starting points that I always look at. So if you make 150 to $250,000, that's anywhere from 10,000 to $15,000 per year spent on a vacation. Now, if someone listening right now is not used to spending that amount on a vacation, you may be saying to yourself, 10,000 or $15,000, that seems like a lot. But let's say, for example, you go on a couple of different vacations throughout the year. Maybe you go on a weekend trip with your spouse, or you go on a bachelorette party with your friends, or you go out and spend some time with the kids. Well, all that stuff in today's day and age is going to add up over time. And so when you start to think through some of these budgets, you want to make sure you fit in all the different trips that you have throughout the year. Or if you make 250 to $500,000 per year, that is anywhere within the range of 10,000 to 25,000 per year that you can spend on a vacation. And again, when you think about this in percentages, some of those numbers may sound high to some of you and some of them may sound low. And then 500,000 and up, you can spend anywhere from 25 to $50,000 per year on a vacation. Now, obviously some of these numbers are going to matter how many people are in your family, how many travelers you have in place, and how many trips you take per year. But that is a number that we can consider when we think about our income and when we Think about it on a percentage basis. Now, this number is your ceiling. So when you're starting to think about this, I want you to make sure that you set this number in place and you have this ceiling for the year. Because if you go over this number, then it's going to have to give somewhere else. So this is why when we focus on this and focusing increasing our income, we can really do some cool things with our income, which is why we here at your next dollar believe that you should focus on increasing your income. Because guess what, those percentages start to rise. You can spend more on the things that you love and less on the things that you hate. So this is one of those areas I really, really want you to focus on. But the big question then comes up, well, what if you want to retire early because you don't want your vacation budget eating into your early retirement? Really, if you want to overspend on vacation in some of these different areas, you want to do that at a time where you plan on working for a longer period of time. So when we think through retiring early, and I know a lot of you listeners do want to retire early, we just want to make sure that the vacation budget does not eat into that early retirement timeline. Otherwise it could extend the amount of years that you are working. And so that is just one other consideration when you are thinking about this budget. Yeah.
B
So, Andrew, I think those are all really good points. So I have a question for you. When you go on vacation, do you show up at the airport and just book a flight or do you plan in advance?
A
I plan way in advance.
B
Yeah, I do too. And I would say that's 99% of the people do. And it makes sense taking kind of that example. It's like that's how a financial plan plays into it. It's the exact same way. Just like you would plan out a trip, you need to plan out planning for the trip. So that's where in terms of how much people can spend on a vacation, I also allow the plan to dictate that. Right. To your point. Financial independence and potentially retiring early is certainly a goal of a lot of our clients. And we can find your financial independence number and back into what you need to be saving and budgeting today in order to meet that goal. What I always say is like, once we have that number, that creates capacity to spend on whatever you value. Right. And that could mean spending half of that on a vacation. We're all very different. But again, kind of think about how you would plan for a trip you need to plan for your life in that exact same way. So that's where having a financial plan that's tailored to you is really important. If traveling is a big priority for you.
A
Exactly. It's basically the parameter and it locks it into place so you know exactly what's going to happen for your financial future. And then you have the extra left over that you can focus on spending more. And one of the keys is people will ask themselves, well, I don't know how much I'm going to spend on my vacation as of yet. I'm still planning this out, I'm still thinking through this process. And one of the things that we love to do is run the love it, hate it audit.
B
This is a really important point, Andrew. So I just got back from Japan and it's a big trip. I live here in New York. So again, it's something that we plan for over a year in advance. You know, a trip that's not inexpensive. So we ran our love it, hate it audit in terms of like, what do we want to spend money on when we go to Japan and what don't we care about? So let me start with what we value when, when my wife and I travel. So number one, and I say this with zero shame, I like luxury hotels. There's just something about it, you know, work so hard, like when I travel, like I to be in a place where the service is outstanding. So number one, like we prioritize luxury hotels. Okay, so what does that come at the expense of? Well, I'm not a big foodie and you know, it's so funny because we got so many restaurant recommendations from friends before going to Japan and a couple of them were Michelin star restaurants and I don't really value that that much. So we went to zero Michelin star restaurants and instead we did an ali food tour, which was super inexpensive. So that's for me, I, I like to spend less money on food when I travel and more money on accommodations.
A
And I love that because I think this is one of those areas most people don't think through as they start to go on vacation. And it's one of those things where when you start to, to look at this, you can start to list out some of these areas. Maybe we're looking at flights, maybe we're looking at food, maybe we're looking at transportation. What are some of those areas that you absolutely value for me specifically? I am 6 foot 4 and the older that I get, the more I value having more leg space on a flight for Example, so I will start to spend more to have more leg space or even, you know, go to first class. I think that is some of the cool stuff that you can think through as you start to plan out these trips, but then cut out the stuff you don't enjoy. Most people feel as though they have to go to the Michelin five star restaurants just because they're in Japan. No, you don't have to do that. What you want to do is the things that you actually value and look into those.
B
You know, you make an interesting point about flying first class. So we flew business class and part of the reason we flew business class is a, it was nice to have more leg room and all of that good stuff. But it's a 15 hour flight and what we were looking at is like, wait a second, like we're already paying a good amount of money to go to Japan whether we fly business class or economy. But here's the thing, by flying business class, we were able to sleep, we were able to be well rested when we got to Japan, which means we hit the ground running versus in economy. I just know myself like I would not have been able to sleep. I would have lost an entire day in Japan. So while it was more expensive, like I was thinking about how much am I spending on this trip kind of per hour that I'm able to experience it. And again, being able to spend more on the flight but hit the ground running day one and have basically zero jet lag, that was something that I was willing to pay up for.
A
I love that per hour framework because I think that is something most people don't run. And if you think through your trip that way, it is going to change the way that you make choices when it comes to some of the ways that you're spending. Let's say for example, you love to fly business class and you love going overseas with that business class flight. I like to front load some of those expenses, some of those bigger or major expenses. I like to try to find ways to use credit card points and miles or ways to reduce that overall cost. And so usually when I use my points and miles, I will find the optimal way to kind of reduce the big ticket cost that I absolutely love. Then I can trickle down and use my cash for some of those other areas. So as you're thinking about your budget, if you do use points and miles, you can also think through the framework when it comes to that Part of this is going through and building your personal travel tier. So after you run your love, it's or hate it list. One of the things that you need to now do is decide exactly what you want your trip to look like. You don't have to copy other people's vacations. We just established that when it came into our love it or hate it list. Instead, you can come up with your own tiers. So once you have these tiers in place, maybe you love the first class flights or the business class flights, maybe you absolutely don't care about those. You want to sit and coach, but you want to go in the luxury five star hotel. Or maybe you care more about going out to really nice restaurants, but could care less about taking excursions throughout the city. You got to figure out, figure out exactly what's going to work for you on each trip and go there. There's no right answer to this. There's only your answer. And the goal is to know exactly what that answer is. And so when you start to think through this, I would encourage you to sit down. If it's just you traveling or you and your friend or you and your family, sit down and figure out what everybody truly values and go and plan your trip based on what you value instead of what you think you need to be doing based on what everybody else says to do on Instagram or wherever else.
B
I want to do a callback to what you said earlier with respect to financial independence, potentially retiring earlier, maybe being at odds with travel. And it's interesting because I was talking to someone recently who takes an international trip every year and they want to fly first class. And when looking at that goal and reconciling that with their financial independence dates by spending more on travel, pushed their financial independence date back by a couple of years. So they were able to decide, well, okay, like instead of reaching financial independence at the age of 50, we reach financial independence at the age of 52. But that means at the age of 40, I can fly first class on these international trips that I want to do. And it's not up to me to decide whether that's right or wrong. It's for them to decide if that's worth it for them. And you know, we oftentimes talk about in with money and finance, time value of money, but there's also time value of experiences. So doing that dream trip at the age of 40 is much different than doing that dream trip at the age of 62. So again, for, for this particular person, it was worth it to push back the financial independence date to be able to have those experiences in their late 30s and early 40s.
A
And this is why a financial plan is so important, because then you can make logical decisions based on small tweaks. And along these same lines, one of the big things that we talk about is front loading. Those Fountain of youth trips, those trips where your body is actually, you know, more active and it's able to take some of these trips.
B
Yeah, that, that, that's a.
A
There are.
B
I went to Hawaii last year and we took surfing lessons. It's the first time I've ever tried surfing. That's way different when you're doing it in your 40s versus when you're doing it in your 80s. So, you know, that's something where, like going to Hawaii and doing that surfing trip, I'm not going to be able to do that forever. Once again, like, that's something that you probably want to prioritize when you're in your 30s, 40s, early 50s, versus waiting until you're in your 80s, a cruise you can do at any point in time. So if there's a worldwide cruise, like, yeah, you could probably do that in your 80s. So that's where it's thinking about again with that time value of experiences. You have to think about kind of matching also that kind of that dream bucket list trip with kind of the physical capacity to be able to do it and to enjoy it.
A
Right before we had our kids, my wife and I went to Puerto Rico. We hiked in through the rainforest. We would have never been able to do that, you know, 30, 40, 50 years down the line. But this was something where we were able and we kind of went through that process and it was really, really cool to see that. So front loading those trips is, is really, really important as you start to consider some of the trips you are taking. And if you're checking off a bucket list, maybe look at some of the more active trips up front and consider taking the ones where you are on a cruise or laying on a beach later on down the line because they will always be there, no matter, you know, what your fitness level is when you start to think through some of that stuff. Now, one of the things that I love about vacations is thinking through experiences and thinking through experiences as a family. So one of the things I've noticed, and a lot of research has been done about this, but a lot of adults will say some of their best memories when they were kids were their family vacations. Maybe it wasn't even a lavish vacation, maybe they just went to a lake house every single year, but they always remember those trips. And I think this is a really important investment for a lot of high earners out there, especially if you have a family. This is going to be something you definitely want to consider. In fact, Ryan, I came across this video which is the perfect example to illustrate this point.
B
Can you name three gifts you got
A
for Christmas last year?
B
Don't remember? I don't know. Where do we go on vacation this year? Turks and Caicos. We went to the Disney wish. The Disney wish.
A
So this is the perfect example of what kids remember and one of those areas that I think a lot of us need to remember. If you have family or if you're married or if you have friends and you want to spend more time making some of those memories. And one of the considerations that you can have is, and I have a friend who does this every single year, they replace a lot of their Christmas gifts with, with one big family trip. So if you feel as though there's a bunch of junk under the tree, you know, come holiday time, or if there's a time of year where your kids have birthdays, you can replace some of these cool trips with, you know, something that you can do as a family and create some of those memories. So replacing stuff with memories has always been something I absolutely love doing.
B
Yeah, I also, it's funny, I was reading an article recently that was talking about the importance of family vacations. And the reason it's so important is because, number one, it makes you a family unit. You're out of your environment. It's kind of like you and your family against the world in certain respects. But also it's important for kids to see what happens when things go wrong. Because with travel, a lot can go wrong with travel. Flights get delayed, flights get canceled, you know, the hotel's not ready when you get there, whatever it may be, you know, the kids get to see you watch when things don't go 100% to perfection outside of their routine. But also like I think about family trips growing up and oftentimes it's the things that you don't plan for and the things that just happen spontaneously that are the things that I remember the most. So one thing that I, I, I like to remind people of is when you're going away with kids, they just want to be with you. So it doesn't need to be something super crazy and extravagant, especially with younger kids. Like going up to a local lake in the summertime is probably just as impactful as going to Rome for a five year old.
A
Absolutely. Even my kids, for example, they are just happy if we book a hotel room, and it could be in the same city that we live in, they just love to be in a hotel room. And my kids are 7, 5 and 1. And so this is one of those things that I think most people think, oh, I got to take them on this huge, lavish vacation. No, especially when they're younger, you can take them to places that are just fun. They just want to spend time with you. They want to enjoy that time with you. And so I think that's a great point to have on hand.
B
One of the things about a financial plan, too, that is very important as you're building wealth is, is finding balance. We see this all the time where there are people who are spenders and people who are savers, and the spenders are the ones where they just go all in. They don't know how to build constraints. They don't know how to say no when it comes to luxury travel. On the flip side, they're the people who are the ultimate savers. It's so hard for them to spend any money with anything. And then when it comes to travel, it's like they miss out on things. They miss out on experiences, they miss out on excursions. They miss out on treating themselves because. Because they save too much.
A
If you are someone who overspends, maybe one of the things you want to consider is paying in cash for your vacations. If you're the type of person that feels as though, oh, the credit card swiping will just never end. When I'm on vacation and money doesn't really matter once I'm there, I just want to spend and enjoy as much of this money as I possibly can. Then you get home and realize the credit card bill is $25,000 and you got to figure out a way to pay this off asap. If that's you, then maybe thinking through paying for everything in cash for vacations could be a great option. I just had a friend who said this about dis. Every time they go to Disney with their kids, they feel as though it's just going to be swiping the credit card left and right. There's no budget in place. They do everything they want to do there. And so it's one of those areas that you just want to make sure that you know that that's you. Because once you can identify and understand that you are the spender, then that's a big one. And if you're the saver or if you're overly frugal, then this is one of those areas where you want to figure out your want list and some of the things that you love doing and try to spend a little more in that area. And for savers, a lot of times it's just hard to spend a little more. And so what I tell them to do is increase that dial slowly. Maybe on the first trip you spend 10% more, do one or two things that you normally would not do. But I've always said, man, I would enjoy really doing that. And then you can increase it maybe 15 or 20% on the next trip and start to slowly increase the amount that you're spending and that'll make it hurt less and you'll kind of get used to doing this over time. In fact, spending is a skill and once you learn that skill and learn how to spend more, that can be very helpful.
B
Here's an interesting thing too. So I know someone, a good friend of mine who I've talked up travel so many times with him, he's a super saver and finally convinced him you need to go and you need to take that trip. And he did. And he came back to me. You know what he said?
A
What?
B
I actually don't like to travel. It actually, I don't find it rewarding. I don't like spending money on these things. He spends money in other areas. So he's not, he's not cheap. He just spends money on what he values. And I guess it was like one of those things where it's like travel's so important to me and something that I make a priority for myself, but that's not for everybody and that's okay. So it's also just knowing who you are and knowing who you're not. And if you are that like super saver that just doesn't really want to spend money on travel and you're just not enjoying yourself because of it. Like it might not be your thing and that's okay.
A
Now the next thing to talk through is using vacations as a mental health roi. For a lot of people out there, especially high earners, you are working really hard in your career and most of you are go getters, most of you are getting after it. And so we want you to consider vacations as something, as a mental health return on investment, where you are spending some of those dollars so that you can get back to normalcy, get back to a point in time where you reduce your stress and anxiety. If you are someone who feels as though you have a really stressful job or a job where you are just constantly under pressure, then Making sure that you increase the volume of vacations that you have on hand can be very helpful for a lot of people out there. Now, if you're trying to think through how to do this, you can frame this as a non negotiable because it is an investment in yourself and in your health long term.
B
I can tell you like, I almost think of my life in the way that, you know, companies report on a quarterly basis. I kind of report back on a quarterly basis with my own life and looking back the three months and saying, okay, what happened? What went well, what didn't go well? And let's look forward to the next three months. So for me, I, I take a vacation more or less once a quarter now. It's not always going to Japan. It could be just a couple of days. But that's really important for me because I work so hard every single day. And then being able to have that mental space and capacity to again have the reflection of what happened, but then also plan going forward, it's something that I really need to then be able to hit the ground running and to continue to put that time and energy into my day to day. It also gives me a lot of ideas too. So it's almost, it's with almost like 100% probability that I come back from vacations with some newfound inspiration or some new ideas that I can implement in my day to day.
A
That productivity point is a huge, a huge component because for a lot of folks, you know, you're in the day to day, the week to week, and you're grinding through the month and then all of a sudden, you know, you get a little bit time to think and you have a little extra time to be able to kind of think through your processes. And then all of a sudden you, a lot of ideas come to you. And that's the really cool thing about taking a little time off as well. The last thing we're talking about in this episode is automating your travel fund. So if you're saying to yourself, this absolutely sounds fantastic, we need to make sure that we set a plan in place so that we can start to take more vacations, then this is going to be one of those areas where you can automate the travel fund. So opening up a savings account or figuring out a place where you can put this money and then figuring out what your vacation number is is going to be two of the steps that you take. And then divide that number by 12. So if you want to spend $12,000 per year on a vacation, send $1,000 per month automatically likely into that fund. It's a very simple process that you can think through. Now one of the things that I'm doing right now, Ryan, is I am actually setting up a taxable brokerage account. And what I do is I fund this taxable brokerage account every single month. And every 10 years, I want to take a big, massive grand vacation with my family with the money inside of that taxable brokerage account. It goes down a little bit in the market or up in a little bit of the market. I don't really care. Instead, I just want this money to go in a place where I know it's going to grow over the course of the next 10 years. Years. And so this is a fun little experiment that I am testing out with me and my family when it comes to vacationing. I love it.
B
I love it. You know, I, I usually plan a year in advance. And you know, you were talking about something earlier about how just the power of paying with cash and how important that is, especially if you want to be a spender because it does put in those constraints. So for me, of course, non negotiable, I'm paying for everything in cash. But when I plan a year in advance, I'm buying plane tickets a year in advance. And there's almost kind of some like mental accounting and like, almost like a trick that I play with myself in that, like, that's done, that's gone, I've already paid it off. So when the trip comes, it's almost as if that is not factored in to the expenses. So it's like I am paying for the flights with money I already saved, and then the money I'm spending on the trip is what I'm starting to save for a year in advance.
A
I love that. Cause I think for most people out there, if you're taking the trip, you know, on a whim and you just kind of decide to go do it, that's where you end up overspending. But if you're planning this out way ahead of time, you have the ability to do a couple of things. A, you have the cash on hand. B, you can plan out your credit card points and figure out, okay, well, this is how many points I'm going to have on hand. I can reduce the overall cost of this trip. And C, a lot of times you can figure out some better prices when it comes to your trip. Instead of kind of doing it a month out or, you know, six weeks out, that is going to be where you get much Better prices. So that's a great point too, is to plan these ahead of time. It's going to help you save overall. And in addition, we want you spending more on these trips, which is the entire point of this episode. Next we're going to shift gears and go into ranking some of our favorite ways to take vacations, the length of time, and some other really cool, fun stuff. Vacation upgrades worth paying for. Ryan, here's the first one is business class.
B
Absolutely. I rank that as an S especially. What I was talking about earlier is like if you're going on a long trip, it's so important to arrive at your destination refreshed, ready to go. You're going to maximize your time.
A
What about airport lounge access?
B
That's not a huge priority for me. I would put that almost like a C or a D especially they're so crowded today. I don't see a huge differentiation.
A
What about premium economy on long haul international flights?
B
I would prioritize business class, so I would put that as a lower priority.
A
What about priority boarding?
B
Absolutely. I'd put that very high in the list. Again, it kind of goes in with the upgrading to business class because you get the first boarding group. But if you're not upgrading business class, I would put that as an.
A
What about TSA PreCheck?
B
Yeah, that's an S. Absolutely.
A
That's a must have suite upgrade at the hotel.
B
Depends on the hotel. I would say if you're staying at a luxury hotel, you probably don't need to. So for me, again, I like luxury hotel travel, so I would actually put that as a lower priority. I'd put that maybe as like a
A
C or a D. Ocean view or premium view upgrade?
B
Ooh, depends. But I'm going to say make it a priority.
A
Make it an extra about a late checkout.
B
Yeah, that's helpful. I'd put that as like a C though. I don't think it's a huge. I don't think it's a deal breaker one way or the other.
A
Club level or executive lounge at hotels,
B
I would put that a D or E. It's not overly important to me.
A
Private airport transfer in the day of
B
Uber, I don't think it's as important. So I'd maybe put that as like
A
a C or a D. Rental car upgrade.
B
If I'm in a place where I'm gonna be driving a lot, I would say I would put that as an A. If I'm not, I would put that something like a D or an E.
A
Skip the line or fast pass at major attractions.
B
Oh, I would put that as an A. Maximize your time.
A
Cabana rental at the resort pool? Ooh,
B
I think it depends. But if it's a crowded pool, I would rank it as like a B. If there is enough space, I would put it down as like a D
A
or E. All right, that's it for today's episode of your Next dollar. If you're getting value out of these episodes, make sure you're subscribed to this podcast. And don't forget to leave a five star RA rating and review. It truly does help us reach more people and helps out the show. Thank you so much for listening to this episode and we will see you on the next episode.
Podcast: Your Next Dollar: Money Management for High Earners
Host: Andrew Giancola, NerdWallet Wealth Partners
Guest: Ryan Sterling, CEO of NerdWallet Wealth Partners
Date: June 9, 2026
This episode tackles one of the most debated questions among high earners: When and how can you confidently splurge on luxurious vacations—without jeopardizing your financial future or feeling guilty? Hosts Andrew Giancola and financial advisor Ryan Sterling break down concrete frameworks for spending on travel, the critical “pre-checks” before you book that dream trip, and how to tailor every adventure to your values and circumstances. They share tactical budgeting strategies, real-life examples, and a lively ranking of vacation upgrades—all through the lens of wealth-building and life satisfaction.
Hosts rate which upgrades are "worth it" for high earners, with a focus on maximizing enjoyment and value:
| Upgrade | Ryan’s Rating & Reasoning | Timestamp | |-----------------------------------------------|---------------------------------------|--------------| | Business Class on Long Flights | S (Top) — “Arrive refreshed, maximize time” | 27:13 | | Airport Lounge Access | C/D — “So crowded, not a differentiator” | 27:26 | | Premium Economy (Long Haul) | Lower priority, prefers full business class | 27:34 | | Priority Boarding | High — speed & ease | 27:40 | | TSA PreCheck | S (Must have) | 27:54 | | Suite Upgrade at Hotel | C/D — Only worth it in certain hotels | 27:59 | | Ocean/Premium View Room | “Make it a priority” for special stays | 28:13 | | Late Hotel Checkout | C — Generally helpful, not critical | 28:17 | | Club Level/Exec Lounge at Hotels | D/E — Not important personally | 28:26 | | Private Airport Transfer | C/D — Uber is usually sufficient | 28:33 | | Rental Car Upgrade | A if driving a lot; D/E otherwise | 28:40 | | Skip-the-Line/Fast Pass at Attractions | A — “Maximize your time!” | 28:51 | | Cabana Rental at Resort Pool | B if crowded, D/E if not | 28:57 |
Approachable, conversational, and actionable. The hosts encourage reflection, share personal anecdotes, and inject humor, while grounding travel spending in responsible planning and clear numbers.
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