“I’m 40, burned out, and don’t know what’s next in my life”

Courtney and Ray, a military couple in their 40s with $715k net worth, are deciding whether Ray should leave the military or stay for his 20-year pension. Ray is near 18.5 years of service, Courtney is returning to grad school to become a therapist, and they're wrestling with how frequent moves have affected their kids and what they actually want beyond the numbers.
Questions this video answers
$715,353
$590,571
$34,782
$17,487.72 (≈$209,000/year)
57% (drops to ~47% in a scenario where Courtney earns ~$50k)
Chapters
I'm 40 years old and, like, I'm tired of reinventing myself all the time and having to make new friends. It's exhausting.
I don't know what I want to do when I grow up, and that's a little scary.
We've always agreed that we will live off of his income, and anything that I would bring in is extra. He didn't like that I separated that money.
It felt like she was trying to hide something. It's a little sneaky. It felt a little like she was trying to hold something back.
Well, one thing we all have in common is we lie to the people that we love. There is love in in line.
I'm about to open Courtney and Ray's conscious spending plan, which breaks down their net worth, their income, and where they spend their money. You can download and create your own conscious spending plan for free@iwt.com CSP application says, we're wondering if we have prepared enough and we can afford for my husband to leave the military.
Assets are $90,000.
Investments are $590,000. 60.
Savings are $34,000. Debt is zero for a total net worth of $715,000. All right, without even looking at their.
Income yet, nobody trips and falls into having $590,000 of investments. That is careful, consistent investing over the long term. So well done on that.
Let's look at their income.
They're making $17,000 per month. Fixed costs are at 57%. So let's talk about two things that I see in this CSP.
First of all, there's a question about cash flow.
What are they doing on a monthly basis? The second question they want to know is, do we have enough? In order to answer that question, I would need to talk to them about their pension, their lifestyle, what kind of life do they imagine for themselves? What's going to happen and change with their expenses as they get out of the military. I'm really looking forward to speaking to this couple.
The reason we came on is because we're kind of unsure, for the first time in 20 years, knowing what the future is going to hold for us financially.
Our life has been pretty. I don't wanna say scripted, planned, just due to the nature of his job. And so pretty soon, we're gonna start getting to make choices for ourselves, which we've never done.
Yeah.
And that's scary.
Courtney, in your application, you wrote, we are a military family getting ready to embark in the civilian world in the next few years. We've spent our entire adult lives as a Military couple with job stability.
We live in a high cost of.
Living area and would love to settle here and buy a home, but we're not sure we can. Tell me about the options you have when it comes to retiring from the military.
I actually ran the numbers. Did I tell you I did that?
No, but I love it. Oh, my God, by the way, I love it. This is how you can tell? We've been talking for like, 15 seconds, and an optimizer's like, I ran the numbers. Look, everybody, look. I ran the numbers. Like, they cannot wait to show their numbers. We'll get to the numbers. Okay, Ray, financially speaking, what are your options when it comes to potentially retiring or not from the military?
I'm at about 18 and a half years now. So at 20 years, I'll get a pension, and it is 50%. And for every year after that, I get an extra percentage on top of that.
Okay.
Kind of where we're going with that is what makes sense. How long to stay in. What does a civilian life look like after retirement?
Do you have to retire or.
No, I don't have to.
No. Okay. When you started the military, which was like, basically when you were 20 years old, how long did you think that you would stay in?
Man, my initial contract was about 10 years, and I thought that would be it. I never thought I would be in the military this long, but things just kept going right, and I kept enjoying it. So I stayed.
Like, what happens at nine years and six months? Like, do you get called into a meeting? Like, what happens?
You actually have to make the decision a little bit prior to that, but just the military knows what they're doing, so they offer you money to stay in as a signing contract.
And I like this. I like the optionality. And then every time they offer you a contract, do they offer you more money?
They do. They do.
Okay. All right, you're right. They know what they're doing. And so the two of you talk about it. You go, hey, they're offering this. What are we thinking? Etc. So in many ways, isn't this upcoming contract just one more conversation that you've had many times over the last 20 years?
This one is. Is a little bit different.
Why is it different now? Why not just roll into it like you did so many others?
Well, I think, honestly, our family is. I think we're ready to move on.
So that's the thing, you know, when he was in the military, starting 18 years ago, we were 22 years old. We had no children. We have three children. Now we have three daughters. Our oldest daughter is in middle school. And as they get older, it gets harder. And it's not just our lives that that are affected. It's theirs also. I'm 40 years old and, like, I'm tired of reinventing myself all the time and having to make new friends. It's exhausting. We love the lifestyle. We don't know any different. But also, there's something to say. We love where we are right now, and if we could stay here forever, we would. And, like, could he earn more in the private sector? This is what we don't know. This is why we're here.
A lot of good questions, especially the ones about the kids. As they get older, it's tough to move. How many times have you moved?
Oof.
I actually counted. So our youngest daughter is 6, and we're moving this summer and she will have lived in five houses.
Wow.
What's the language you use in the house when it's time to move? What do you say?
It's gotten harder as they get older. It used to just be we're going to go on a new adventure, but it's more of a brace for impact.
I appreciate you sharing that. I can see how it would get more and more difficult, of course, on your kids, also on YouTube. And at a certain point you go, hey, wait a minute. Like, this is a natural time to really think about what we want to do. We're 40, 41. What do we want the next chapter of our life to be?
Where we are right now. We're very happy, and eventually we would love to come back here and live here. And so it's like uprooting this life that we don't really want to uproot, but have to due to his job. We want to maybe be able to make the decisions for ourselves at some point. We've had a lot of fun, but we're starting to get to the time now that we can make those choices. And it's just, I don't know, it's being 40 years old and being able to make a major life decision for yourself for once is new.
Yeah. How have you structured your career goals over the course of the last 20 years?
It's really mostly been around, are we having a good time? Am I enjoying what I'm doing? And knock on wood, I've been successful up to this point, so it's been a steady climb in rank and those types of things.
Got it. Courtney, what about you in terms of your career? How did you think about that?
So Mine's completely different. We were married, I was a teacher. When Ray and I decided to have our first child, we decided that I would stay home. So I have been a stay at home mom for 12 years. I am lucky that Ray has provided me the opportunity to dabble and find what I'm interested in. And in October, I went back to grad school to start my next phase.
Oh, what's that phase?
I want to be a therapist.
Oh, cool. How did you make the decision to go back to school?
I've wanted to do it for 10 years. There's always an excuse. I tend to make decisions in fear. I live in fear a lot. And I was scared to invest in myself and do that. But when he was, he was deployed last year and I was like, you know what, eff it, like, time's going to go by, I may as well just do it.
Where'd that come from?
I mean, I think turning 40 is like a big, you know, three years is gonna go by, so I can either do grad school or not do grad school, but those three years are gonna happen.
Very courageous, honestly. That's awesome.
Thank you.
Are you both feeling that same? We turn 40, it's time to zoom out, take stock of where we are, where we're going.
Yeah, I think so. And not only how you've done, but how you're going to do in the future. And then with kids, it's like how we setting them up too.
Yeah.
I think we also thought like, 40 is like, oh, it's so old. Like once you're 40, you're settled, like you have your life together. And I was like, you know, it's not that old and it's never too late to try something new.
Yeah, I love that. Let's talk about potentially retiring from the military. So, Ray, if you were to retire, what does that look like for you?
It would be in about two and a half years. And then, you know, I would be out of the military and I would get that 50% pension. But after that, I don't know because I don't know what I want to do when I grow up. And that's, that's a little scary.
Yeah, I can see how it could be even more scary for you because there's been structure since you were 22 years old. It's like, do this, you'll get that.
Yeah.
But going into the civilian world is very nerve wracking.
Yeah. And I gotta imagine it's probably different at 44, so that's true.
The opportunity cost or the alternative you have is to stay where you're sort of at the peak of your career. You know everybody, you know the systems, you know how it works. And you can play that game. Yeah. On relatively easy mode versus going to a different world where the rules are unclear and maybe your skills aren't what others have. That's a very scary moment.
Yeah, absolutely.
I remember interviewing a football player. He had been in the NFL, I think he'd been to the super bowl, and he, you know, retired. And it was like a very stark awakening for him because he went to being at the absolute top of his game to being a, quote, nobody. And to me, I found that incredibly courageous because that scares the out of me. Like, I'm good at what I do. And if you took it all away and I had to start off, could I do it? Yes. Is it really scary? Yeah. All right, so let's say you retire. It's unclear what you would do. I can hear that there's some interest. Any other goals that you would have if you were to retire?
My goal is he gets a job making at least what he makes now. And then hopefully I'll be working by then. And then we have his pension. So now we're a three income family instead of a one income family. And he continues to work and work for like 10 to 15 years, sock away his pension and then like retire by like 60. Hopefully he would have enough to be able to do that.
And then what?
I don't know. That's a great question.
I'm actually really glad that we get.
A chance to talk.
I don't think a lot of people know unless you have somebody in the military or you grew up with friends who are in the military. It's like for many people it's a different world.
Yeah. We knew nothing. We did not come from military families at all.
Is that right?
Nothing?
No, nobody.
How'd you decide to go in the military, Ray?
My father, actually, he. He said, hey, why don't you go try this summer seminar for the college? And I tried it and I loved it.
Isn't that crazy?
Your entire life can change from one comment somebody makes.
It was one week long and it changed my entire life.
Okay, back to the goals of retiring. Anything else in the near term that you would want to do?
We do want to own a home. That's part of our goal for us. We're leaving this summer. We hope to come back and buy a house here.
Gotcha. Okay. So that we would need to factor that into the calculations as well, to see if at some point you could be able to afford something in that area. Okay. All right. Ray, have you thought about what careers you might go into after you retire?
I really haven't. This is just one of those civilian military kind of disconnects is I don't even know what I'd qualify for. I know I have experience in leadership, but I don't know how that far. How far that takes me.
We'll come back to the career stuff because I understand that's a big part of this decision.
I just want to cut in here to give a little bit of context on how big this decision is for Ray and Courtney. Now, I've spoken at military bases before, and one thing I didn't expect was the structure of each day. They handed us an itinerary of what we were going to do while we were there. And it was detailed down to the minute. I'm not kidding. I'm talking 0652 Morning Workout, 0745 Helicopter Tour. Personally, I loved it. I love that level of detail. But you have to remember the effect that that has on somebody. For 20 years, Ray and Courtney lived that structure. The military told them where to live, when to move, what to do. And now they're considering leaving that structure behind. No regimented schedule, no next contract. Just this big open question, what do we actually want? And when. You've spent your whole life following the rules that someone else set, that can be really scary. You don't have to be in the military to understand what I'm talking about. Maybe you grew up with strict parents. When you finally got to college, you weren't sure how to decide what you wanted to study. Maybe you got divorced or you left a religion and suddenly nobody was there telling you what to do anymore. You get used to the structure. Many of us even come to depend on it. But when it's gone, it doesn't always feel like freedom. It can feel scary. And sometimes we just feel lost. That's exactly where Courtney and Ray are right now. After the break, we'll get into the numbers and just wait until you hear what happened when Courtney quietly set some money aside. Years ago, when we took our honeymoon, we decided to go on a long six week trip and we wanted to do something special. We invited our parents for the first.
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T. Why don't we take a look at the numbers? Courtney, why don't you read off the word in bold and then the full number next to it for this entire box.
Ask that. Debts are 90,000. Investments are 590,571. Savings are 34,782. Debt zero. Total net worth 715,353.
Okay, cool. What do you think of those numbers?
They're fine.
That's very lackluster worth.
They're unremarkable. Like they're average. I don't know.
Okay, Ray, what do you think?
I think they're good. I like the debt. The debt number, really? I'm proud of.
Proud of the debt number.
Okay.
Yeah.
What else?
We are proud of ourselves, that we've done it all by ourselves. We don't come from, like, money and things where people have helped us. So everything we've built, we've built together on one income.
Yeah.
I wish they were more, but I think it's a good place to start.
Okay, let's keep going on the numbers, huh? This time I'm going to ask Ray to read off this combined gross monthly income here.
All right. $17,487.72.
All right, so that's $209,000 household income. Did you know that? Yeah. Okay. Courtney, did you know that? Wow. All right. Very good. In order to live a rich life, you have to know your numbers. That is a core part of it. Great job. What does it mean to make $210,000 at the age of 40 and 41?
I don't try to look at it by the numbers, and I think we do all the things we want to do and we're never really hindered by financial things. So I think it's a good number.
Courtney.
I think it sounds like it's a lot more than it feels sometimes. Maybe I'm overthinking this, but if One individual makes 200k a year, it's very different than a family of five.
Tell me more.
So we have three children. We have all their activities and expenses that come with children. We have savings that we have to take into account that someone without children or one or an individual wouldn't have to. So I think the money, it's all being utilized, like, for a purpose.
Listen, everything you're saying I can understand and empathize with. In some cases, I agree with you. Like $210,000 is a lot of money and it's very successful. And also if you have a family of five living in a high cost of living area, I can also see that that money can get spent quite easily.
I'm looking at it, and it is a lot of money. Like, we're paying for my grad school out of pocket. Like, most people can't do that. I'm grateful that we have those opportunities. It's just the money can get used very quickly.
Courtney, have you earned any money since Ray has been in the military?
I was the teacher and then I had my own business doing nutrition.
Okay, what was that like when you were earning money and he was deployed, et cetera? What's that look?
So when I do earn money, which isn't much, I took all my little money, like, I think I earned. Was it like 3, 300 last year? It was like, very little. And I put it in, like a little special account. He didn't like that. I separated that money, but to me, I separated the money because we've always agreed that we will live off of his income and anything that I would bring in is extra. So I put it aside so it didn't get, like, wasted and blown on whatever. And we had a lot of travel plans last year that we had to cancel for a few different things. So I wanted to make sure the money was there so we could use that money to travel. And he got really mad that I would separate that money.
What did he say? Do you remember?
I think that I was trying to hide the money or something.
And do you remember where you were when you had this discussion the first time?
That was right before deployment. Some way, I found out that that money was going into a different account, and it just didn't make sense to me. And I said, I. I don't understand why this is your money. To save on a different trip that she wanted to go on to see a friend in Germany. Where is everything that I make is what we make. It's together. So why wouldn't what you make also go into that same account? And then we just do the same thing we've always done with it?
So here is my thing. I gave up my career 12 years ago, and it sounds really lame, but, like, making that money, like, felt like kind of special, that I, like, earned money. And so I just wanted to make sure that I used it in like a. A special way.
It's.
It's lame, but when you hadn't had a career or an income, and that's kind of a Bummer sometimes, like, it just felt, I don't know, more precious.
So how did you all resolve it?
I don't make money anymore, so it's not an issue.
Yeah, it honestly hasn't been resolved. I'd say that's a contentious thing that we have in our relationship.
What'd it feel like for you, Ray?
It felt like she was trying to hide something a little sneaky. It felt a little like she was trying to hold something back. I didn't like it. I still don't like the idea of it.
It sounds like there was no resolving it, but rather, Courtney, you stopped earning money, so the problem has kind of temporarily vanished.
Yeah, but I will say, like, if I were to make money again now, like, I wouldn't do the same thing.
What if you made $3,000 in a year?
I wouldn't do it again because it upsets him. I. I want. I wanted to take this trip last year for my 40th birthday to go see Taylor Swift in Germany with my best friend. And so I just wanted to make sure that there was no reason that I wouldn't be able to do this because of finances. And so, like, that's kind of why I scrolled it away, to, like, make sure that money was there.
Why would you be worried about not having enough money if. Courtney, you, like, control. You seem to know your numbers quite intimately. Why would you be worried?
It felt like an accomplishment for me to be able to buy that for myself. I think that's mostly what it was. He's been our sole income for so long, so it felt cool to be like, hey, like, I did that for myself.
Yeah. Do you all have independent, guilt free spending amounts that each of you can use on your own?
Nope. It's all together. Everything we do financially is together.
You ever disagree about, like, why'd you spend on this or that?
We used to when we were younger, but I think we had kind of an epiphany at one point, and we were just like, you know what? We trust each other, that we're not gonna do something silly, that it doesn't matter, and if there's something that is quote unquote expensive, we'll talk to each other about it.
We both trust that we're gonna spend appropriately. She just bought a new bike.
How did this. Did you bring the conversation up or did you buy it on your own?
He was going to die if he kept riding his old bike. It was broken. And he was like, I need a new bike. And I said, great. He bought it on Marketplace. He didn't buy it new. It's like probably a $7,000 bike.
Yeah.
$7,000. What. What kind of brand is a $7,000 bike?
It's a carbon fiber bike.
That changed everything for you now, right?
Definitely. Please don't write me in the comments explaining how cool these bikes are. I do not care. How did you have the money for it? Like, where did it come from?
We had already planned from the tax return. I was overseas last year and we had a lot of tax free money coming, so it was like a big windfall.
How much did you get in that tax refund?
15 grand.
What are y' all going to do with the rest?
So the idea is to fund the IRAs with that.
Okay, so you all agree on that?
Boring. But yeah.
Yeah.
Is it some of it? Not all of it, but some of it.
Let's go through the rest of the CSP.
Okay.
Your fixed costs. What's that number, Courtney?
57%.
57. So this great. It's below 60, 50 to 60 on one income in a high cost of living area. Impressive. Let's break it down. Your rent, because you're currently renting, is $4,050 per month. You guys get a housing allowance from the military?
We do.
Oh, okay. And the military's housing contribution, you factor that into your income. Yes, got it. Okay, good to know. All right, let's keep moving along here. So I have no notes. As long as you're within 60%, you can spend it however you want as far as I'm concerned. But just out of curiosity, looking down here, we have car payment at 500 bucks. It's very nominal. Amazing. Great. No debt. That's awesome. Groceries at 1500. That's five people in the house. What do you think about that number?
Priority for me is to have high quality food in the house. So it's hard to get it lower here. To be very honest.
I will say it's a little higher than I normally see. But then again, you have a pretty big family and your number is still within 60%, so totally up to you. That's your rich life. It's your priority. I'm all for it. What's up with this subscription being eighteen hundred dollars a month?
That includes my grad school. That's my monthly bill, so I didn't really know where to put that. Okay, so if it wasn't for my grad school, that would be at like $500.
Can we just model it for a second? So let me just show you. Instead of 1800 I'm going to make it 500. Look at this number up here. This 57% fixed cost. It drops to 48%.
Whoa.
Now I'm bringing it down.
No, no, no, no. Not at all. In fact, if anything, I'm like, wow, that's great. You can fit grad school and still be below 60%. Amazing.
Thank you.
Great. Let's continue moving along. Investments are at 20%. That's 20% of after tax money. So you are contributing $1,900 a month to post tax retirement, and then you have 700 bucks a month for a 529 for your kids.
Yeah.
When you look at your numbers, what do you both think?
I think that we can get a little more sophisticated and optimize and make some better choices and set ourselves up better.
Okay. What does that mean? Set yourself up better for the future. Okay, got it. Ray, what about you?
It's hard for me to visualize what the future is going to look like with the investment number and especially the 529. Honestly, it's hard for me to see what, how I'm going to pay for kids colleges and going forward. But at the same time, I'm proud of where we're at. It's cool to be in a. In a situation of, hey, maybe I have the opportunity to take my investments down. Even down a little bit. Like, that's pretty. That's a pretty cool position to be in.
Yeah. Let's say instead of X dollars, you took it down by 500 bucks a month. What would you do with that money?
If we're taking away something as precious as 500amonth from investments, I want to make sure that money is being used wisely in a way that'll serve our family. Something that's intentional.
Well, let's do it right now. We're here.
Let's do it. I would love to take that $500 and go get, like, microneedling done. But.
Hold on. Why is there a but?
Because, like, what would that $500 be in 10 years in an investment account versus, like, my amazing skin? But what's worth more?
Can you answer that for me?
Yeah. It would be the investment account.
Oh, so all that matters is what's going to be in your portfolio 25 years from now? Am I hearing you right?
But no, I don't agree with it.
Yeah, like the microneedling. How much does that cost anyway? Microneedling?
Probably somewhere around 750.
$750?
Courtney says she wouldn't feel comfortable spending $500 on herself, quote, unless it benefits the family. Did you catch that? It's not just a throwaway line. It's a window into how a lot of women think about their money, especially mothers. I've spoken to many of them on this show and many of them will say something to the effect of spending money is okay, but only if it's for the family, particularly for the kids. And then she tells us something that seems small, but it provides a really big insight into what's going on. She earned $3,000 last year and she put that money into a separate account. She says it's not to be sneaky, but because it felt special. The money wasn't just money. It was identity and accomplishment and freedom. Now, Ray doesn't get this. He sees it as a betrayal. And I can understand that. Why would your partner want to put money in a separate account that doesn't feel like there's trust, that doesn't feel open and transparent at all? And what we see here is a clash not just of hiding money, because I don't think that's what's going on, but a clash between meaning and control and autonomy and partnership. Courtney says she won't do it again.
Good.
Because I don't think hiding money is okay in a relationship.
I think we all get that.
But there is another issue that I want to highlight here. It's what happens when you start treating every dollar like it has to justify itself. It's when you are happy to spend money on everybody else, but you find it almost taboo to spend on yourself. This is one of the reasons that I insist everybody have an individual guilt free spending account and that you use it. You can't just let it sit there and grow and do nothing. Your skills at spending money deteriorate. And when you start using the word justify. How do I justify spending money on taking a trip or playing golf or getting my nails done? You're not just avoiding conflict. You're actually building a life where fun and whimsy doesn't even make the list. After the break, I'm going to dive into this topic even more. All right, here's the situation. I order a bunch of stuff. It comes in a bunch of boxes. Once in a while I have to return it.
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How much did that mattress cost?
$2,200.
Is that a lot or a little?
What do you think about that number?
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Like one of the gifts that I can give people is a different view on their money. And one of the things that I often hear from people who are very sophisticated with their numbers is that they often live in the future. This is typical of optimizers I know because I am one. Optimizers see today's money as how much it could compound into in 20, 30, 40 years. They're intuitively attuned to that. The problem is they can become unbearably cheap and unbearably future focused, meaning they often can't enjoy the present. Now, I'm not saying you should go today. And if you want to get microneedling, like, I don't know, we have to look at the numbers still. But I am saying your numbers look pretty good to me. Let's continue moving along. Savings are at zero. You have about $35,000 in savings, which is about four and a half months of fixed costs. What's up with that?
He's not going to lose his job tomorrow. So I just. We felt comfortable with that much money in savings.
Got it.
And so we'd rather let it grow in investments.
Okay, so your guilt free spending is 23%, which is nice. 20 to 35% is what I typically recommend for you. That's a relatively high number. $3,616 a month. And would you say that in general you spend that every month?
Not all of it, no.
Okay, what, what kind of stuff do you spend your guilt free spending on?
We do like to eat out when we can.
I like to go thrifting or just going out with friends on a weekend. I guess the way I think about it is like all of our money is allotted where it's supposed to go. And so whatever is left, we just spend how we want.
Yeah, yeah, that's, that's the way I see it as well. Make sure that you're, you're paying yourself first, your money's going where it needs to go and whatever's left over, enjoy it guilt free. Your numbers look pretty good to me. It's very impressive what you've accomplished on one income, three kids, moving around a lot, living in a high cost of living area, having a pension that's going to pay 50% and possibly more like this is really, really impressive. And if by the age of 40 or 41, if you want to get micro needling, I am 100% sure we can figure out how to make that happen? How does that sound?
It sounds great.
I think the real crux of it is what do you actually want in your rich life?
We just have never really pegged down what it is.
Have you all ever talked about what is our rich life?
We have, like, I mean, I have your journal right there. Your. The couple's journal.
Hold on. Go, go get it. Let's take a look for a second.
I don't even know if I have to get outta my seat. Let's see. Look at that. I even have. Look. Look at this. I even have a pencil in it.
Oh, I love that. Okay, hold. First of all, hold that. Cover up to everyone. Listen up. All you optimizers who can't dream worth a damn, get this journal right now. This is the same one I use on my Netflix show. And go through it. It's no numbers. Do it with yourself. Do it with your partner. Now just flip it open.
Show us.
Is there any writing in there?
No, there's not.
There's a pencil.
The optimizer didn't get to the writing part. The optimizer just bought it. Didn't go through it. Okay.
Oh, no, I did. I did, I did. I wrote it.
Okay.
In your rich life, how would you travel differently? Business class.
Oh, that's true.
You say that all the time.
Give me some more. What else you got in there?
That's it, Ramit.
The whole journal. You wrote one answer.
He wasn't home last year, and I didn't want to do it by myself. I wanted to do it to together.
That's kind of sweet.
What a revealing moment. When I asked Courtney and Ray about their rich life, went silent because they've been asking a totally different question this whole time. Can we retire? That is the question they have optimized their lives for safe. It's practical. But for so many people who build their entire lives around that boring question, it doesn't actually provide insight into meaning. Can we retire? That's a good question. It's valuable. It involves a lot of math. It involves values and expenses and savings rates, all that. It's a good question, but it's not the question. I'm not here to retire. I'm here to live a rich life. And that is what I want for Courtney and Ray. That's actually exactly why I love role playing, because it takes people out of this intellectual space. They think they need more data. Oh, we need more information. Well, I'm not sure if this worked. No, you don't need another spreadsheet or another calculator you don't need somebody like me coming and telling you if you can retire, what you really need to do is start by asking a much more important question. What do we want? If we assume for the moment that we probably have all the information we need, if we assume that, hey, if there's a math thing we don't know, we can probably figure that out. Then you realize you don't need a magic number. What you need is to ask and answer the question, what do we want? This is one of the most important questions in life. Do you know they could answer that question today? And after we finish with their numbers, that's exactly what I'm going to help them do.
I just want to put a little bow on the numbers from what I see in the csp. And then if you're cool with it, I'd like to go through a little exercise with you to try to help you figure out what your rich life may be, because I think that will help you make some decisions about your future.
I love that.
I love it.
So we pull up your CSP.
Okay.
We see that you have almost $600,000. Age 40. I'm almost certain it's probably invested in low cost index funds and it's compounding, et cetera. Your fixed costs are at 57%. 57% fixed cost means your fixed costs are well within parameters, especially considering you have grad school in there.
Great.
Okay. How long is grad school going on for, Courtney?
So about two and a half more years.
Okay, great. And then do you know what your income will be once you graduate and start earning?
Say, maybe like around 50k? If I was working full time, I. I could probably make a lot more than that. But my priority will always be to be able to be home with our kids, but also have this fulfillment of my own career.
I love it. Okay, back to the CSP. Let's just say you're making 4,000amonth gross. Let's just say for easy math, 3,200 net. I'm plugging it in right here. Okay. Can we watch this? Oh, my God, look at this. What's that number that your fixed cost just went to?
47.
47%. That's, like, really low. Amazing. And we got to take off your grad school here. Yeah, we're down to 40%. I mean, come on. That's very impressive. What do you take away from that, Courtney?
That would give us the ability to spend a lot more money to buy a house.
Yeah, that's true. You would have thousands of Extra dollars per month if you wanted to buy a house.
Yeah.
Okay. So right there, we're assuming that Ray is earning the same income. All that stuff we're holding constant just for this hypothetical, but we're seeing. Wow. A second income at $50,000 a year can be incredibly powerful.
It's just enough to, like, really tip the scales and give us a lot more flexibility to. To find business class or to buy the house in the expensive area that we want to do. And I wouldn't feel constrained. I don't like feeling constrained. Or that there's not enough money. I don't want to be house poor.
Are you sure you don't like feeling constrained? I think you love feeling constrained. I think you love it.
We.
Come on. What are you talking about? I don't love feeling.
You literally love it.
You love every part of this spreadsheet.
You love the rules, the ability to.
Have to make it work within a certain number. What are you talking about? You don't love it.
So, like, I have anxiety. Weird. And, like, having that control is really comforting for me. There's not a lot we can control all the time in our life.
Yeah.
So when I can control the things that I can control, I control them.
Honestly, I'm with you. I totally get it. When I'm doing things that are out of my control, like when I was shooting my show or I'm on tour, it makes me understand all these celebrities who have these riders of all the stuff they need in their green room. It's not just that they're divas. It's that they are completely out of control on these national tours. And they need to know that when they walk in, they're going to have the type of sparkling water that they want, because it's that one thing that they can control.
I get why Courtney wants control. When you don't get to decide where you live or how long you'll stay there, you start clinging to the things you can control, like the numbers. I have personal experience with this. When I was traveling, shooting my show for Netflix, I had very little control over my schedule. What did I have control over? Which deodorant I brought, which soap I use, which shampoo I brought with me. Those were the things that I could control, the things I brought with me. That's it. That's why I didn't use the hotel soaps, because I don't know if it's.
Going to make my skin dry.
And it seems like this trivial little example, but it's true for all of us. In times where we don't have control, we will often narrow our world down to a tiny soap so we can feel like we at least have something that we're in charge of. But here's the catch. If you are focused on managing every detail, you often don't leave room to ask the bigger questions, which we still haven't answered. What do we actually want? The answer is probably not more and more control. Maybe the answer is actually letting go or just zooming out for a minute. Just enough to dream a little bigger.
Over the past couple of years, I've been working on up leveling my social media content. Take a look through my Instagram, for example, to see. You'll see infographics, thumbnails, edited videos with graphics. I don't make that myself. If I made them, you would know. Look like a freaking stick figure. Okay, with one color.
Black, black and white.
That's it.
I'm not a designer.
I'm not an editor. And that's okay, because if I need something specific done, I can hire great freelance help on upwork, the sponsor of this episode. Here's a list of projects my team and I have hired freelancers for On Upwork over the past few months. Graphic designer for PDFs, a TikTok video editor, a content editor for email campaigns, and a web designer for a new sales page. It's easy to post a job on upwork. It's no cost to join or register. You can browse freelancer profiles. You can get help drafting a job post and even book a consultation. From there, you connect with freelancers, browse their portfolio, and easily hire them to get started on projects right away. Upwork makes the entire process easier and more affordable. With upwork, you can access top talent across tons of different industries, including IT, web dev, AI, design, admin support, marketing, and more. So visit Upwork.com right now and post your job for free. That's Upwork.com to post your job for free and connect with top talent ready to help your business grow. That's up w o r k.com upwork.com do you guys know how much money you're going to have when you retire?
No. And here's my question for you. We haven't even talked about his pension. Like, do we need to save like we are?
Doesn't it kind of. Isn't this kind of like the question?
Yeah.
How come when I talk to couples, especially where one is really knowledgeable about the numbers, like they know their numbers, how come they never run the one number that actually matters, which is how much are we going to have if we continue on this path? Courtney, I'm asking you because this is you.
I did it.
You ran the number? No, I don't believe you. I just asked you, do you know the number?
Well, I don't know if it was accurate because I don't know, like, if I use the right calculator.
Okay, tell me your number. Let's find out about this calculation. What number do you have is either.
Like 4.7 or 7.4. That's why I'm not sure.
Hey, listen, I'm all for approximate numbers, but that's kind of a big deal.
It's approximately between 4 and 8 million dollars.
So the number was 4.7. That. That's about right, based on the numbers you just inputted.
Okay.
And that would assume that you retired at 60.
Yeah.
Which is totally fine. I ran a similar calculation for you all retiring at 65, and I took what you have at $590,000. I assumed you're contributing about $37,000 a year, plus or minus 24 years. At 7%, it gives you $5.1 million. That does not include the pension.
Oh, well, yeah, that's. I mean, that sounds like a lot. I just. It doesn't feel like. It feels like pretend.
What money feels real to you, Courtney? Of all your money. Which money feels real to you?
The money that exists today.
What else?
What? The numbers that we have access to.
The checking account?
Yeah.
What else? Does your savings account feel real? Yeah. Does your $590,000 in investing feel real? Oh, all of your money today feels real, but the money tomorrow, the millions, does not feel real?
No. We're about to get to, like, our most expensive years with our kids when they're in high school and college. Like, we might not be able to put in as much money. Like, we just don't know.
I've never heard that number before, but it feels pretty awesome to me.
So is that for real? Like, you've been carefully saving and investing money for, like, close to 20 years, but didn't run how much you're going to have and really interpret that. Is that accurate?
Very accurate.
It's quite interesting, don't you think? What do you think's going on there?
I think we're so used to just living, like, in the present, we don't think about the future that much.
Yes. And even when I ask you, like, this is just math, of course, maybe you won't invest the same amount for a couple of years, but on the other hand, maybe you'll start earning $50,000 a year and actually invest more. Who knows? So we have to pick some variables and hold them constant. But even if you're off by a couple of percentage points, we're talking about five plus million dollars and a pension of a lot of money. Yeah, that's a ton of money. And what this really tells me is like, this isn't a math problem. Five million bucks. You can safely withdraw quite a bit of money from that, plus the pension, you'll have a very nice income, hundreds of thousands. What's more interesting to me is that because of how you've been relating to your money, it's been like, get to the next contract, like short term thinking. And now you're being asked, hey, in this potential civilian world, what do we want to do? Yeah. What do I want to use this money for?
Yeah.
And that is a really different skill set than the one that the two of you have quite frankly, thrived on. What do you take away from that?
I think change is scary.
Do you know how much you're gonna get in your pension right now if.
He got out the next chance that he can? This is just base pay. This is about like VA stuff, which is probably like another. So let's say 30,000 a year, maybe. So he'd be at 78,000 a year.
Up to potentially, let's just say like 110,000 a year. Yeah, fine.
And then if he got out in.
What, that six years.
Six years, it would be about 110,000 plus. That's like 140 guys.
This is a really. This is really important. Yeah, it's one of the main factors in this decision. You have to carefully calculate how much are you going to have and also, do you need it? First of all, in any case, it's a lot of money. Okay, 78 to 110. If you retire in a couple of years or up to 140. That's also a ton of money. Not to mention your investments. Not to mention that, Ray, you're probably going to get a job and then, Courtney, you're going to get a job as well. Like, we got money coming in from lots of places. The question is, how much do we need? Do we need 5 million? Do we need 7 million? Do we need 10 million?
We don't know.
What would it take for you to know, man?
I think it's envisioning what we want from, say, the rest of our lives, but we want to buy that house. We want to be able to travel business class. It's putting a number on that.
I grew up in the same home until we got married. I had one house my whole life. I can look back and, like, picture my bedroom. Our girls, like, can't do that because they've had so many. And I just have this, like, sadness for them that they haven't had stability and like, settled in one place. And as they get older, I want that for them.
If you asked your kids that picture your bedroom and they said which one? Just as you described it, what would their tone be when they said which one?
They might all have a different tone.
Yeah, I agree. I think the oldest one would be negative, but the other two might be more positive.
You know, as you get older, your friends are more important to you. Like you don't want to leave those things.
My parents, we moved around a bit. Not as much as you, but when I look back.










