77. “We have $6.3 million. Why can’t we take a vacation?”

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Every time you sit there and say, God, I wish I'd win the lottery and I'm like, well we kind of have and we still don't. We still wish we could win the lottery.

Each month I'm putting money away. That's how my mind works. It's like that's how you get. That's how you get by shit. Yet I realize there are times that I do feel like I control things too much and that's probably a huge downfall for me. And it's stupid. She's not doing anything wrong. But this is how I react to myself. I get worked up over stupid ass stuff.

Okay, and do you want that relationship the way it is now or do you want to change it?

I want to change it, but I worry. I worry that if I'm not in control then.

Whoa, whoa. I didn't ask about the. But I just asked if you want to change it.

Yeah, a little bit.

And that's probably my biggest fear about retiring is that I'm not going to have my own money anymore. We're not going to spend any money now because he feels like we don't have the double income. And by the time we can spend money, as, you know, when we're older, I won't want to travel as much. And we're saving for Tom to live to 100 is what we're doing. We're totally saving for Tom to live to 100. I want to do stuff now.

Meet Tommy and Caroline.

Tommy's 60, Caroline's 56. This is their second marriage, both of.

Them, and they've been married for six years. The reason they came to me is that Tommy is having trouble spending. And because Caroline is just about to retire from a very stressful job, this has become a very pressing topic. What are they going to do when he continues to work and she's retired? She wants to travel. She wants to spend some of that money. He does not. Now, for everybody listening and watching on YouTube, I want to encourage you to treat this episode like a crystal ball. You have the chance to see into your future and to see what it might look like if you accumulate a bunch of money, but you don't necessarily know how to spend it. So for those of you listening to the I Will Teach youh Be Rich podcast, or for those of you watching it on YouTube, I welcome you to this episode of Tommy and Caroline.

I need to chill because I think we're in a really good position. Caroline's retiring this March, and I'm so excited for her because she's got a super stressful job. I know we can make it work. Yet I freak out too much. I freak out when I see all these Amazon purchases and I question why it's happening. Perfect example. Caroline decides to buy a pair of headphones that we already have, a wired pair of headphones. And I know it's stupid because it's probably like a 20 or $30 purchase, but my mind just says, hey, we already have it. I need to let go of that kind of shit. I know I do. Because she's doing nothing wrong. Nothing. But I get worked up on that.

When you say, Tommy, that you freak out, Tell me exactly what happened.

It just kind of nothing was said to her. But I just inside, I internalized by saying, why did she do that? There's no reason for that. I wouldn't have done that. So why does she do that? And it's stupid. She's not doing anything wrong. But this is how I react to myself. I get worked up over stupid ass stuff.

Hmm.

Okay, Caroline, do you remember that headphone situation?

Well, yeah, I could tell because he kind of rolls his eyes or he tries to control the situation. He'll say, we don't need it. It's a good thing I did buy him, because we would be in bad shape right now if I didn't buy, because the ones that he had didn't work.

That's one. What else?

What was something that you just bought? That's. Oh, okay. She's probably going to get mad at me on this. She was telling me on a walk that she just purchased a cool dress that she really liked, that she. For an upcoming wedding. Don't know when that wedding would be, but it'd be a cool dress. Yet she also confided by saying that, yeah, don't know if I'll really be able to wear it or fit into it, or maybe it won't work for this particular wedding. And it just blows my mind. Why would you buy something when you don't know for sure that it's doable?

It was $600.

Okay.

And where did that money come from? Which account?

My account.

Your personal account?

Yes.

Okay. How long have you been married for?

Five years.

Seven years. Well.

Known each other for seven. Married five.

Okay.

All right.

You guys want to get your story straight on how long you've been married?

Well, we met 2013. We got married in 2017.

That's nine years.

No, 2000. Well, okay, 2017.

We've known each other for nine years. We've been married since 2017.

Isn't that five? Am I doing my math wrong?

It's five and a half. So almost six years.

When we got married, it was my opportunity. I was like, listen, babe, start fresh. Let's just do our wedding anniversary and birthdays. We can't do, like, the first date and the first time our parents met. It was just too much. I said, let's just start fresh. So maybe that's what's going on here.

Yeah.

All right, so you've been married somewhere in the neighborhood of less than 10 years, whatever the number is, yes. Okay. Is this first marriage for both? Second.

Second for both of us.

Second for both. Okay, great.

Notice a few things already. When Tommy describes himself as freaking out, I ask him to get really specific with his behavior. A lot of people use the word freaking out to describe all kinds of things.

Some people use it to describe losing.

Their temper and screaming at their partners. Other people use the same phrase for the very mundane. Like, they sit in their heads and they wonder, hmm, Is that worth it? I really do not like the phrase freaking out. In my opinion, it is never descriptive. And I find that People who use this phrase tend to start to treat it almost like a comfort blanket. They'll just shrug and say, I started to freak out.

I can't help it. I don't know.

That's just me.

I freak out, no, we're not going to do that.

We're not going to use inflammatory phrases and then laugh it off as just.

This quirky little thing. Ha ha ha.

I just freak out. No, we're going to get specific with the attitudes and behaviors that we use when it comes to money, and then we're going to specifically dig to see if we can rebuild those habits so they can start to serve you.

So when you initially got married, when was the first time you talked about money in a serious way?

Caroline? I'd say the first time we talked about it was we discussed that it'd be beneficial to us to have a joint account and each one of us have our own separate accounts that are the accounts that we had. And that way it wouldn't be, oh, I'm going to nitpick your spending and vice versa. But then again, I hardly ever spend anything, and I think that so far, that's worked out really well.

Caroline, what do you recall about the first time you talked seriously about money?

Yeah, same thing. We were going to do a joint account, and we were going to contribute a certain amount of money, and then if we could afford trips, we'd take trips or, you know, stuff like that. So, yeah, we definitely had our separate, which I would definitely need. And that's probably my biggest fear about retiring, is that I'm not going to have my own money anymore. I'm going to have to sort of rely on, like, going into, I guess, our money, but it's more Tom contributing than me contributing. So, yeah, it's going to be uncomfortable, probably.

And how far off is retirement for you? March 31 in a few months. Okay. Wow. Early. Congratulations. That's cool.

Yes. Thank you.

All right, so when you describe your feelings about retirement, are they positive or negative?

I'm negative only in the sense that I planned on working longer. It's just my job's too stressful. I work for a company that was bought, and they got rid of people and just made other people do more than they normally have to do, and it's just too stressful. I can't do it anymore.

Yeah, gotcha. All right. How would you describe the two of you in terms of money? Like, Caroline, if you had to describe Tommy in a word or two? When it comes to money, what words come to Mind for you.

Conservative.

What else?

I don't want to be mean. I mean, I think he's kind of. I think he's kind of cheap, I think. Yeah. I mean, I know that if I want to. Like, we. If we look at boats and we bought a boat for our lake house, I knew, you know, it had to be reasonable. There was no way. Like, there's some boats out there that are, you know, 60, $100,000. There was no way. There was. Even though we probably could afford it. There's no way. It's not even an option.

How much did your boat end up costing?

Bought a used boat for $18,000.

Okay. I don't know anything about boats. In the grand scheme, is that cheap, expensive for your area and your place of living?

I'd say it's cheap, yeah.

All right, here's something I want to throw by you, Ramit.

Okay?

Here's a perfect example of how my mind works. I'm always, like, competing with myself. We got gas. I filled up the car the other day. I was so pissed at myself. A couple miles down the road, I got it. I could have gotten it for $0.12 less per gallon.

Tommy, this cannot be really happening right now.

Another incident.

Come on. Did it involve strawberries? Tell me.

We're getting Yellowstone, okay? We want to get the fifth season of Yellowstone, okay?

It's a good show.

I went ahead and bought it.

You bought the HD version? No. Hell no. Okay? I never do that either. That's a waste of money. I'm never gonna.

And then I find out my son said, hey, Daddy O. We got. You already have it on YouTube TV. Why don't you ask me?

I'm pissed at myself for $40. I mean, it's not even worth it.

I mean, how come he didn't say something? Or how come I didn't check it out? I thought I did. It's not funny.

How much sleep did you lose over that one, Tommy?

I probably did. I know it's stupid, but I'm just. That's how I deal with stupid shit like that.

Tommy is doing this interesting thing here where he's pre apologizing. Have you noticed it? It's like walking into the room after you've done something and going over the top with your apologies. I know I shouldn't have done that. I'm terrible. I just can't do anything right. I'm sorry.

One apology is good.

2 is better. 10 starts to feel disingenuous. I want you to be aware of this because it might be A real acknowledgment of contrition.

Or it might be a strategy.

Sometimes it's actually an unconscious strategy that people use, but it is a strategy nonetheless. Personally, I find Tommy really likable, but I'm starting to get a little suspicious of the number of times he's apologized in just the first few minutes of talking. But really, I have no idea. It's just a guess. Right now, let's pay attention to what he says and how he says it.

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And the other thing that may seem whacked but I just have this feeling I'm going to live a long time. Like to at least 100. And I'm not saying this as bragging, I just feel I'm going to live a long time. I want to make sure that I don't have to be a burden to anyone. Never do I want my kids or anyone to worry about me.

How many kids do you have, Tommy?

Three.

All right, how old are they?

Oh, they're old. They're 34, 33 and 30.

All right.

And how are they doing?

Successful. They're all fine.

Okay, great. Do you anticipate them needing your financial help in their lives?

No.

Tommy, we spoke on the money coaching call. That was a lot of fun. So you raised your hand and we had a conversation in our money coaching group. Tommy, do you recall the conversation that we had.

That I don't believe a lot what you had to say in terms of kind of convincing me that we are good financially and that if I wanted to. I remember talking about we want to take. I want to take a trip to New Zealand.

All right, you got to hear this clip.

I was doing a Q and A with my money coaching group members and I saw Tommy's question and I knew I had to take it. Listen in.

All right, Tommy, if you are here Tommy, please unmute because I really want to talk to you about this question. It's so good. Tommy says I just turned 60. My wife is retiring this April. I've been self employed for over 30, 34 years. I will continue to work because I enjoy it. My wife has worked her ass off and she wants to spend. I would love to know how much I need to budget each month so I can chill. Can you help me? Two question marks. Okay. Tommy, please. Are you on this call?

I'm here.

Oh, okay. Tommy, my man. First of all, I love that you put save in all caps. It must really be on your mind. Why do you like to save?

I don't know, it just.

It's.

It's like, competitive. It's like the more I save, the better I'll be in, more prepared. My financial guy says we're good, you know, and I don't believe him. And he. He shows me facts that, you know, each year it's going to be worth more.

You see it here. You see the math? Here you trust your guy. But here you don't really believe it. Is that correct? Hell, no. But I did notice you said this thing about. My wife has worked her ass off and she wants to spend. And what does she want to spend on?

And you know what? She does not spend a lot. She really doesn't. She's very good. But I just.

Oh, wait. Not spending a lot means you're good. Did I catch that?

Well, no, she really. I know, I know. But what if she starts doing that?

Keep going. What if she starts doing it and then what happens? Like, what if she starts spending a little bit and then she trips and falls and starts spending $50,000 a month? Any concern about that happening?

Oh, yeah, no, not that much.

But how much then?

I don't know. I'm embarrassed to say that, you know, I, like, I gotta keep saving.

I talked to so many people who are in this same situation, and they have 500,000, 5 million, 13 million. And they still cannot bring themselves to spend.

I told my group I'd like to go to New Zealand.

Oh, what's there?

The world's highest bungee jump.

Oh, my God. Okay. Amazing. That is terrifying to me. You are healthy. You have the money, you have the time, because you work, and you seem to have a flexible schedule. Is there anything stopping you from doing these things?

I can't afford it.

The fact of the matter is, you're 60 years old, you're healthy. You want to go bungee jumping in New Zealand, and you can afford it with the money that you probably have in your checking account or savings account, or if not, after two months, you would be able to afford it. What would that feel like if you did that?

I think. I think it'd be cool.

Have you ever done something like that?

No, I'm the worst. I. I analyze everything.

Just a quick question again. You're 60 years old. Do you have to wait until next winter to go?

Yeah, because I need to save up.

Okay, so, like, how much is in all your accounts? Just like a. Are we talking like, ten dollars? Ten thousand? A hundred thousand? Just a ballpark. If I were to open up all.

Your accounts together was 3 million.

3 million, plus the house, 2 million, plus the cash flow. Right. I'm not sure. You need to save up 500 bucks a month for a year. Anybody agree with me? Like, could you just go and then pay yourself back?

No, because you got to work for it. You got to, like, save.

Tommy, Tommy, listen to me closely. There is no virtue in living a smaller life than you have to. You already have the money. You have the health. You have a loving partner. You have kids. You won. It's time to cash it in. That was a live Q and A.

From my money coaching program where I show you new ways to apply my material to your finances. And I answer your money questions right there on the spot. You can join@iwt.com moneycoaching. That's iwt.com moneycoaching now back to my conversation with Tommy and Caroline.

I. Each month, I'm putting money away because that's how my mind works. It's like, that's how you. You get. That's how you get by shit. You get. You don't just say, okay, I'm going to buy it. I got to make sure that I have the money, and if I don't, I'm going to save up for it. I'm going to earmark this amount of money, and that's how I'm going to do it.

Sounds pretty reasonable the way you say it, but I also remember that I had to pull teeth to get you to talk about New Zealand. And then when you finally said, oh, that would be cool, it was like, yeah, we'll go on that like a year from now or 18 months or some long time from now. That sound familiar?

Yes.

I was like, why don't you just go next month? In fact, why don't you go next week?

Can't afford it.

Oh, you can't? I guess I'm looking at these numbers in your conscious spending plan with all those zeros. Oh, that must be a very expensive trip to New Zealand.

My gosh, we're going to live a long time. We got to take care of that.

Not that long. I mean, got a lot of zeros in this conscious spending plan. What's up with that nod, Caroline? You think so, too?

Well, I Mean, we talk about a place in Florida and I knew if we would get a place, it had to be reasonable. So we do some airbnbs and things. One place that we stayed at, the condos were going for 200,000. I thought, oh, he might entertain that. Yeah, yeah. And it was on water, you know, so. So I said something to him and he said, sure. Boom. He changed his mind completely. He was like, I don't think we need to spend the money.

So how do you two come to agreements on spending money? How does it.

I think ideally we come to a solution.

I don't want to know ideally. I want to know real. Give me a scenario.

That was a mistake on my part. I violated my own rule, which is ask a vague question, get a vague answer. And that's exactly what started to happen. If I hear people going into vague language, ideally we do this or we usually do that. I never let them continue. I don't care about their answer because it's always fake in vague language. When we are talking about ourselves vaguely, we're perfect. We always try to work out. We try to eat right. We try to manage our money. In real life, we haven't opened up a sub savings account in five years because our kid keeps waking up at 5am and we lost a password.

And if we roll it all back.

It'S because my mom didn't love me because I got a B on my math test in fourth grade. Those are the details that I'm looking for because those are the details that actually matter. So remember, ask a vague question, get a vague answer.

Give me a scenario.

Well, we don't have the condo. I'll tell you that. I get told no, and I say, what about my money?

You know, I've told her, I said, we're going to travel. I'm not going to wait. That's why I want to go to New Zealand next year. She's like thinking, is this going to happen? I've already put it in the works with the travel agent, so it's. It's going to happen. Not sure what month is probably going to be January or February of 2024, because I got to save up for it. But I'm sure I will have enough saved up for it.

How much do you need to save up for that trip?

I'm thinking probably about 20,000.

Okay, how long is the trip going to be?

A month. I'm already taking money. I'm putting money aside.

Okay, Caroline, do you agree with that?

Yeah, I would think that would be a good Amount of money for a month. When you rent something for a month, it's more reasonable than, like, a hotel for a month or whatever.

Okay, you're about to be retired. Tommy says he doesn't want to retire for a long time. What's that going to mean for the two of you?

Meaning about spending money?

Yeah, or traveling? Spending money, that kind of thing.

I want to keep at the same income level I'm at, which is pretty low, and I do that for tax reasons, so I don't want to be pulling a boatload out of our savings, and I just. I would like to keep it at that. And I'm not working just because, oh, I'm nervous. I do. I really enjoy what I do. It's a lot of fun, and I'm. I think I'm pretty good at it, and it. It excites me. I think guys who retire early die early, and I'm not going to do that.

Okay, Caroline, what does it mean for you that one is going to be retired and one is not?

It means, like, he just said that we're not going to have as much income. And I worry because we're young. I want to do stuff now. I don't want to do anything because we feel like we don't have money. And then when we're 75, because he's going to live to 100, we're going to do stuff. And I'm like, yeah, I don't see it that way at all. I had a mother that did everything. She always was going and going and going. Then she got sick, and she didn't do anything. She ended up still giving us money because later on in her life, she didn't do much. My greatest fear is that we're not going to spend any money now because he feels like we don't have the double income. And by the time we can spend money, as, you know, when we're older, I won't want to travel as much. And we're saving for Tom to live to 100 is what we're doing. We're totally saving for time to live to 100. I see.

Tommy, what do you think about what Caroline said? She had some pretty important things there.

I believe we need to be on the same page. And then I do believe it's pretty smooth, because Caroline's going to speak her mind, and she knows that I'm going to speak my mind. Yet I realize there are times that I do feel like I control things too much, and. And that's probably a huge downfall for Me, but huge attribute because, you know, I own my own business. And I guess I've had to go with that mindset that, you know, the buck stops with me. If things screw up, it's my fault. And hopefully they. They go well and, you know, collectively will do well. But I know I control way too much.

All right, you want to change that or no?

I. Yeah.

Yes. Put it this way. I love playing sports. And when I'm on a team, sports, I am never, ever the coach or the manager because I love when other guys are telling me what to do. Love it. It's like, for once, I don't have to worry about this or that. It's just I got to worry about how well I perform.

Okay, so you like being the individual contributor when it comes to sports at work. You're the person in charge. The buck stops with you. But it sounds like you have also adopted that mentality when it comes to money in your relationship. Would that be fair? Yes. Okay. And do you want that relationship the way it is now, or do you want to change it?

I want to change it, but I worry. I worry that if I'm not in control, then.

Whoa. I didn't ask about the. But I just asked if you want to change it.

Yeah, a little bit.

You really should watch Tommy's facial expressions as I ask these questions. He's quite expressive, and it tells you a lot. Check out the YouTube video.

You could say, no, I'm not trying to lead you with a. If you don't want to change it.

Tell me, then I will answer a little bit. I feel like moving forward, this is. This is a big thing about how we spend our money. And I get. I get worried about it. And even our financial guy has said, hey, it's. You're good. You guys are good. Well, I don't know. I don't know how much we can spend each month. That's what I want to feel comfortable with, because if I know that, then I can chill. I can relax.

So you believe that if you have a certain number in front of you, that suddenly you're going to relax about money?

Yes.

Okay, here's a little pop quiz for you.

If you were in my chair, how would you approach the rest of your conversation with Tommy and Caroline? What route would you take? Think about it. Some people are tempted to emphasize the numbers. Tommy, you're a millionaire. But what if I told you Tommy already knows that, and he hasn't actually changed anything because of it. What else would you do? See, one of the things I'm trying to do here is, is to get as many of the details out of couples that I speak to, but I'm also evaluating the details that they give me. Most of it, candidly, is noise. Some of it is interesting, but it's a route with a dead end or a bad end. You'll sometimes hear me wave couples off of a certain conversation route. They're going, if I can tell it's not going to be good. Other times I. I will hear something and it's really important, but it's not as important as the burning issue. I'll give you an example from this conversation right now. Tommy has mentioned his finance guy. Now, I haven't gone down that route intentionally, but I'm willing to bet he's paying somebody a 1% AUM fee, which is a total waste of money, especially at their net worth. Now, ordinarily I would spend time talking about that, but I don't want to do that. Just like for any soccer referees out there, you know, the advantage clause, just let it go. Same thing here. I can see this mistake happening, but there are bigger things that I need to talk about. And frankly, if I were to bring up that AUM fee, he's probably paying a financial advisor, Tommy would welcome it because he wants to do anything except tackle the real issue here. Ah, the real issue, the burning pain. That is what I'm always looking for. Because if we can solve that, the $30,000 question, or in their case, the $10 million question, then the rest of their concerns are mere trivialities. So this is what I mean by focusing on the big wins. There's usually one main issue that is more important and meaningful than all the next nine issues combined. We want to search for it and take as long as we need to do to find it. But when we find it, we want to go full head on to confront that issue.

When I talk to new business owners, I hear a lot of the same motivations. I want to make extra money. I want more freedom. I want flexibility. But I will tell you something that I've never heard. I want to start a business so I can fill out a bunch of tax forms. That sounds like my hell. The good news is you don't need to be a tax expert to start your own business. Instead, you can use Gusto, this episode's sponsor. Gusto is online payroll and benefits software built for small businesses. It's all in one. It's remote, friendly, and it's incredibly easy to use. So you can pay, hire onboard, and support your team from anywhere. They offer automatic payroll tax filing, simple direct deposits, health benefits, workers comp, 401k matches.

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I don't know. $12,000 a month?

Is that enough?

I don't. Not really.

How much is enough?

I would think 15,000amonth.

Okay, Tommy.

If.

If we can afford it.

Well, I'm not asking if you can afford. I'm just asking how much is enough.

I don't know.

How much did the two of you make together? Like how much the two of you make right now? Every month together. Gross.

Yeah, I think mine's kind of tricky because I'm self employed, so.

How much do you pay yourself, nets?

3,750 every two weeks. Hold on.

Every time people give me these weird.

It's like 7,500.

7,500Amonth gross. No. Oh, that's net. Okay. Oh, God.

So gross. I think was about 7, 300 every.

Two weeks would be higher. Gross would be high.

I know, but the accountant takes out to the 401k to do other things, so.

Yeah, that's why I like to see gross. But whatever. All right, you basically make like 10, 12,000amonth gross. But you could pay yourself more, you could pay yourself less. You choose to pay yourself that much. Right, right. All right, fine. And Caroline, you make approximately 7,000amonth.

Three.

Fair enough.

Yeah, probably mine's going into 401k and medical bill.

Gross.

You.

You make more than that, Caroline. You're about 160 a year.

I just want to point out, as you two dig through your pay stubs and, and stuff, I just want to point out for everyone watching and listening, like, here we have a multi millionaire couple who doesn't even know how much they make. It's because I don't.

I don't look at the bank account.

That's awesome.

He should look at the bank account.

I do look at the bank accounts.

Yeah, it's like 13,000amonth. Yeah, I probably make 13,000amonth. I did 160 divided by 12.

Whatever. It doesn't matter to me. You all make a lot of money. Fine with me. Your money, your income is about to disappear, Caroline. Fine. And Tommy, you can basically pay yourself whatever you want to pay yourself. You choose to pay yourself that much, could you pay yourself more? Theoretically, you have the cash flow for it.

Yes.

Yeah. So, Tommy, can I ask you a couple of questions? So you're 60 years old. Yes. You're multi millionaire successful entrepreneur. Do you accept those things?

Yeah, the. The multi millionaire. No, I don't.

I mean, I'm looking at the numbers. There's a. There's multiple commas. Let's put it that way. You are a multi millionaire if you.

Look at it that way. Yes, I guess.

Yeah, the way. Like facts. Okay, so you are a multimillionaire, successful entrepreneur. How long you been running your business?

Little over 30 years.

Fantastic. All right, how many businesses do we know that even last that long? That's amazing. Okay, you're telling me that in 30 years and millions of dollars of accumulation, you have Never been able to figure out how much money you can safely spend every month.

We've been told about. Figure on $12,000 a month and you'll. You should be fine.

Okay. And do you accept that number?

I think so. I think. I think we can do that.

You told me a second ago I need to know the number because then I'm just going to hand over financial control to Caroline. Well, you know the number.

I don't know if that's the right number. I think it is.

I see.

I see, I see.

Okay.

Never been in a position like this. It doesn't seem real.

Okay.

I mean, I'm proud of what we've done. We've. We've saved a shitload.

Yeah.

And we've done it, I want to say, kind of the hard way. It's like making smart choices, you know, not over spending on stupid shit and not knowing our means.

Okay. And if we go back to you, you saved a lot. You're proud of what you did. You never thought you'd be in this position, and therefore, to think about spending more means what.

Man? If you don't follow the course, Tommy, you're gonna it up. So you better keep, you know, saving. Yeah, that's. I'm just being honest.

I appreciate it. I think that's real. What got you here could work. It would work with the mentality of where you were at 30 years old when you started this business. And at that point, probably you were actually about 30 years old. Right. When you started this business. Yeah. Hustling, trying to get your first client, et cetera. Every entrepreneur goes through that stage. I get that. But every entrepreneur is, in a way, trying to get to where you are. And what a shame if you still act the exact same way you did as when you were 30 years old, just starting out.

I guess I don't look at as being, you know, a shame. It's like, I gotta keep hustling. I got it. I gotta keep having that edge. I gotta keep doing this.

Can you hustle and still enjoy some of the benefits of what you've worked for?

I guess I know I should enjoy it more and more. You know, Caroline pushes me to do that, and I know I'm kind of a dick.

Tommy is showing you what happens to successful people who wrap frugality and saving into their identity. When they finally succeed, it is virtually impossible for them to change their identity. And you will see that successful people like this display a complete inability to get off the hamster wheel. Because when you've always lived for the future, telling yourself that someday you'll spend your money. You have actually let the skill of spending money meaningfully deteriorate. Now, if you are listening or you're watching this, Tommy's actually giving you a huge gift. He's giving you the gift of a crystal ball into your future.

Many of you, especially the ones who.

Have read my book and joined my earnable program and money coaching, you're going to end up with a lot of money. But if you don't learn how to meaningfully save as well as spend it, it's very likely you will end up with more money than you can use and no real ability or willingness to spend it.

Caroline will tell you this, that two things that I love to spend money on and I don't. She said traveling. I do. But when it comes to sporting events and concerts, don't care. I will go to as many as possible, and I'll try to get the best seats if I can. And I love doing that. That's my indulgence.

Okay.

You don't worry that you're spending too much on it?

No, because I feel I deserve it.

Oh, you deserve it. Where did that come from?

Because I wore a card. I mean, to me, that's pretty minor. Just saying, hey, I'm gonna spend it on concerts and sporting events.

Okay, Good answer. What else is best case for you? Concerts. You want to go to one every year? Quarter. What are we talking about?

Oh, shit. At least I'd like to go once a month, minimum.

Wow. Okay. What kind of seats you want to get there?

Oh, that'd be cool to have, like, really good seats.

You ever done that? Yeah, I got you. So, concerts, maybe once in a while, get some great seats, go every month. Fantastic. What else?

Sporting events. Yeah. I think it'd be cool. You know, I. I know so little about soccer, but I think it'd be cool to check out a World Cup.

That'd be cool. Sounds good to me. Do you think we might be able to apply that to some other parts of your life?

Caroline's laughing. I know. I guess I should.

But, Caroline, what does it mean to you to hear Tommy sharing these things? Any surprises?

No. And I mean eventually. Like your 401k, they make you take it out. So then I'm thinking, okay, when they make us take it out, Tom's probably going to put in another savings account. He's not going to spend it.

Yeah.

I mean, I can just hear it.

I know. I know from him. Now I know what retired men do. Like optimizers like you, Tommy. I know it because I talk to them and they take their rmd, you know, they're required to take it out, and then they literally put it right back in. They invest it again. I go, what the fuck are you doing? And they go, well, I don't even know what to spend it on.

And.

And this is where it goes from funny to haunting. They go, what would I spend it on anyway? And I go, let me get this straight. I don't say this to him because I'm not trying to psychologically devastate a 72 year old man, but I go, let me get this straight. You worked your ass off for basically 45 plus years to accumulate a bunch of money provided for your family. You did all that, but along the way you forgot what you actually wanted to spend it on. Maybe you never even built the muscle of knowing how to spend it meaningfully. What's the point of all that money?

I agree.

I sort of agree.

How about the way that the two of you deal with money together? Best case.

Not me bitching. That would be the best case scenario. Not me worrying about stuff because I slowly am believing that we do have enough to. So I can just relax more.

Okay, that's good. Maybe another 30 years, then you'll believe it.

What do you think?

I think 10 years. I think I'll be good. So.

So what changes 10 years from now that you don't already have?

I'll have more.

You'll have millions of compound.

Yeah, but I think it'll help. It'll help us.

Have the two of you ever considered just a legitimate question? Is there a point at which the two of you have invested too much money? Has that question ever come up between the two of you? No. That's what I thought.

Yeah.

Never. Because. Because that's not a question that middle class people ever really confront. It is you save, you invest, you kind of scrap and scrape it all together and hopefully by the time you retire, you've got enough to live a comfortable life and maybe travel fair. Fair. That's the archetype for how we live in America in the middle class. But first of all, I'm looking at that very nice tree behind you, Tommy. Now, I don't know if that's a middle class tree or not, but I'm gonna tell you something. I bought my first Christmas tree this year with my wife, okay? We went to the little tree lot. We got a little tree. I'm talking like, it's like three feet tall, okay? So we have no Idea. Does this tree cost like $10 or $150? We have no clue. So we get the tree, and then we're like, oh, man, we gotta get some lights for this thing. We go to Target. We. We get the light. We don't know how many lights to get. So we get one strand, and then we come home and we. We have to wrap. And we're like, in a budget way, let's just stretch this strand out. You know, it doesn't even go to the top. And I'm looking at your tree. I'm going, that is a very nice tree. Lot of ornaments. Probably took you 20 years to collect that. Plus the fact that I'm looking at many millions of dollars in your bank account. I'm going, maybe some of the old middle class rules don't apply to YouTube. Have you considered that?

Hell, no.

All right, Is it time to consider that now?

I don't know.

I mean, you're talking to a guy who grew up middle class, and now some of the rules don't apply to me. That used to. Maybe this is a good conversation for us all to have. What do you think?

Maybe a little bit I should chill a little bit more?

I mean, that's what you told me you wanted to do on this call. I'm giving you the option here, Tommy.

Caroline's like, yeah, keep talking to me.

She's loving it. Yeah, go ahead.

Definitely. I don't want to be upset about money.

All right, let's talk about it. There is a point where when you accumulate enough, it actually starts not making sense for you to continue saving and investing at the rate you were. Now, this really only applies to people with a considerable amount of money. Okay? The vast majority of people, they need to save more and they need to invest more. And it's very difficult for a lot of people, especially housing costs, all that stuff. You know, in your case, you're mentioning to me, Tommy, that you still put a ton of Money in your 401k, Caroline. Same thing for you. And all that is great. I love a good 401k. I love all these tax advantaged retirement accounts. But the fact of the matter is, Caroline, you're about to retire. Tommy, you're 60. And when I look at how much money you've got and the fact that you're going to continue working, et cetera, et cetera, I start to ask myself, what if you took, let's just say, $5,000 a month, just a round number, and instead of putting it in a 401k, or whatever savings vehicle. You just used it for cash flow and you used it for traveling and used it to not have to go two miles down the road for cheaper gas. And you used it for whatever it is you wanted to use it for. What would happen?

I'd have to work harder.

Okay. Because.

Get more jobs.

Huh? Because what?

Because that's. I. Because I need to keep, you know, invest. I need to go, you know, invest in the 401k and other things and.

Why?

Because it's like I don't. I don't believe I'll have enough or we'll have enough.

Yeah, that's a good answer.

And Caroline, you disagree?

I totally disagree. I think, like I said, my mom, I mean, not to use her as an example, it's probably not the best example, but she didn't have that much money, not anywhere close to what we have. And she still gave money to her kids when she passed. And the same thing with my dad. He didn't have a whole lot of money. And you know, everyone, his Tommy's kids will tell him, like, dad, go have fun. Go spend your money. We don't want any money.

What do you say to that, Tommy?

I tell them to mind their own business.

You know, I told the same thing to my parents. Did you know that?

What?

I sat down with them and I. Because my dad was telling me, you know, he called me and he told me some deal, he got on something and I said, you know, dad, you don't have to go for all the deals anymore. You have enough. And he and my mom, they didn't believe it. And so I sat down with them and I made their finances really simple. Even though my dad is. He's quite savvy with money. But being savvy with money versus knowing if you have enough, those are two very, very different skills. Very different. I said, we don't want any money. We want you to spend every last cent. And I even put em on like a travel budget, but not the kind you think. It's a budget where you have to spend this much every single month. And that actually has proven. It's taken a little bit of work, but it's proven to be a different way of looking at money. What do you think about that?

I think your dad should be instructing me right now.

Probably true.

This is a very interesting and advanced topic, and this is really only applicable for people who have enough money but have an inability or unwillingness to spend it. In this case, we do a bit of a reverse budget in many ways. It's what the conscious spending plan is for. That's why if you download the free conscious spending plan, I put the link in the show notes, you will start to automatically build this skill of spending money in areas that are meaningful to you. I'll give you an example. Let's say that you want to become a better photographer.

Okay, great.

In your conscious spending plan, specifically the fourth category, guilt free spending, you can allocate 200 bucks a month for photography classes or equipment, whatever you want. And you can look at your conscious spending plan and. And you can see what is important to you.

Now. Guess what?

Maybe you try it for six months.

You go, I'm not into this.

Let me put it aside.

Cool.

You just change your conscious spending plan and you shift it to something else. Your conscious spending plan and your calendar really reflect your season of life. And that concept of a season of life is really important. When I was in my 20s, I was very aggressive at saving and investing. And even though my income was relatively low to what it would become, just as almost everybody's income in their 20s is low compared to what it will become, I wanted to get my habits right. I was aggressively investing a larger percentage of income because I wanted those habits and I wanted that compounding to kick in. I was also spending a lot going out Taco Tuesdays. I was living in San Francisco, then New York. I was having a great time now. I couldn't do it all. There were things I couldn't afford then that I can afford now, but I was spending as consciously as I could have. Looking back, I think I could have done things a little differently. I would have probably spent more on having fun, but at least I gave it some thought. If you get to the point where you have more money than you actually need, this happens to a surprising number of people. It's just not talked about in the press. You start to encounter some very unconventional decisions that you may have to make. For example, for the vast majority of people to be able to max out their 401k is a dream. To be able to max out XYZ account is a dream. There may actually be a point where.

You go, I'm not going to max it out.

That money has higher utility to me now than to save it for retirement later. So again, this applies to like less than 3% of people. But on this podcast, I like to show you all Gamuts. Whether you're $800,000 in debt or you have over $10 million in net worth, I want you to know how to play the game of money no matter what level you are at.

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I'll tell you a scenario that.

You'Re.

Going to yell at me, but I feel justified. This past summer, Caroline's son and girlfriend came up. And of course, Caroline said, let's go to the best, most expensive restaurant, which is we love. We both love. And I'm like, why can't we just grill here and just chill? And long story short, it was at least 500 bucks for all of us to eat, drink.

How often do you see these kids?

Once a year?

Well, no, we see them more than that, but this occasion was once a year.

Was it worth it, Tommy?

It was fun. It really was fun.

Do you think 10 years from now, when you have millions more just purely based on compound interest, do you think you would feel differently about that type of meal?

I guess I look at it this way. I wouldn't have expected my parents to do that, and nor would Caroline expect her parents to do that.

Did either of your parents have millions of dollars?

No. No.

Did either of your parents have their own business that they ran for 30 years to this level of success and Caroline's income as well?

Never.

No.

It's hard to take an identity that's not our parents because in a way, deep down, it might even feel like we're rejecting what they taught us. They would never take us to eat at a place that's $125 a person. I get that. And you don't have to do it every day. It doesn't sound like you're doing that, but if you had the ability to ask your parents, mom, dad, if you had the money, would you have taken us out to a nice meal once in a year? What do you think they would say?

Yeah, I think he would.

You have the means. What's really more important than the amount spent on this one time dis dinner is the fact that you have kids coming home. Still a great relationship with them. To me, that's way more meaningful than how much you're spending. You could go to a pizza place for 20 bucks. It doesn't matter to me. But the fact that you all chose to go to this place and you created a memorable dinner, to me, that's way more meaningful than the amount you spent. And I actually think that the two of you have earned the right to focus more on meaning than on money. Most of us go our whole lives only thinking about money. By necessity. We gotta save. We gotta buy clothes for the kids. We don't have enough. But you won that game. You won and you can keep playing. Tommy, you never heard me once say anything about, I need you to retire tomorrow. That's your decision. You won that game of money, and now you get the chance to focus on meaning. And if you don't do that and you just keep playing the same game for the next 10 or 20 or 30 years, you're leaving so much on the field. That's how I look at it.

That's good. That's a good analogy. I like that.

Meaning over money. Think about that phrase. It's not something that would have resonated with me at 20. At 20, I was willing to work unlimited hours. I wanted to grow everything, grow my skills, grow my friend group, grow my net worth. Meaning over money would not have made sense to me in that season of life. And there's another example I want to give you. If you take someone who is struggling to pay their bills, this concept also makes no sense. It's just words. Meaning over money does not make sense, nor is it relevant to someone who's struggling to just pay their bills. But I'm not talking to those two groups right now. I'm talking to Tommy and Caroline, who are multi millionaires. And Tommy's in his 60s. It is a tragedy to live a smaller life than you have to. And for someone worth millions of dollars to even think about the price of a $500 he has once a year with his kids, that is too small for Tommy. Excuse me for being direct, but that is the truth. Focus on the menu. Focus on the ambiance. Focus on the stories you shared over dinner. Focus on anything, but not the price. You are too successful to fixate on the price of one dinner.

Yes.

There are situations where the price of something is totally and completely irrelevant. And this is one of them.

Let's open up that conscious spending plan. All right. Fantastic. Okay, let's. Before we. Before you look at all that. Caroline, just ballpark. Just looking at me without looking at the spreadsheet. How much money do you think you both have?

Okay, so I don't look at our cars and houses income. So I would say we have probably $3 million.

Okay. All right. And how does that make you feel?

I think that's a good amount.

Okay, great. All right. And your understanding of how much income you make per month, total ballpark. It for me.

Okay, so I. I made last year like, 165.

And Tom.

I'm going to say 180 or 200.

Let's say 200. And then we got the house, which generated 60K. Fair. Or even 100K, let's say, because it was grow. Let's gross it up.

Okay.

All right, so that's 465,000 last year. How's that gross? How's that sound? Ballpark.

Sounds like a lot.

Yeah, it does. It does. When you add it all up. Three numbers.

Yeah.

I mean, you guys see something? Look at this discomfort on your faces, by the way. I love it. Do you know what did you, both of you think you make together? Like, Let me guess, like, 180 to 200. Is that what you thought you make?

Well, no, I knew I made 165, but I didn't know.

I thought maybe 300 total.

That's. And do you know why there's such a disparity?

I have no clue.

One of the reasons that I like people to give me their gross number is that when you take the net, you're actually taking out, like, 20k here, 20k there for your 401k and all these other things.

And.

And you just don't count that mentally. That's one of the reasons the two of you have been so successful at investing, because you're just taking out 20k at a time and throwing it into your 401k and letting it compound. Amazing. For investing, growth. Horrible. For understanding how much you're actually making every year. So when you hear 465, hey, look, maybe I'm off by 30k, who the hell knows? But I'm in the ballpark. Would you say that's fair? I'm in the ballpark, right?

I guess. I guess so.

All right, I'm right. I'm in the ballpark. That's a lot of money, right? 465,000. Even if it's 430,000, that's a lot. In fact, it's over $130,000 more than you thought you were making. So it's important to be fluent in the basic language of finance. Now, Caroline, you mentioned earlier that you don't see the house's income.

I agree.

But I do see it as part of your net worth because it's paid off. Would you agree with that?

Yes.

Okay, so you have $2,700,000. No plans to liquidate it. Fine. But it is there, and it's worth $2,700,000. Fair. Fair. All right. All right. Very good. How about your investments?

Where? We're at $3,500,000.

That's a lot.

Yep.

What do you feel about that, Tommy?

We did good. I think we did really good. I'm proud of that.

That's awesome. Solid work. All right, Your savings. How much is in there?

I mean, in our bank, we. I think about $14,000.

Yeah, that's what I see. Why is that number so low?

Low. That's the way it should be. Uh, why would I want to put money that's earning nothing in savings?

You're a classic optimizer, Tommy. You're always optimizing. But if you only have $14,000 in your savings account, which for a multimillionaire is low, then guess what it means. What are the ramifications of that?

Means I'm doing good. I'm putting money in a good source, making interest.

Tommy, you have to wait over one year and three months to take a fucking trip to New Zealand when you have a net worth of over $6 million. It makes no sense.

You gotta save for stuff. You can't just, like, boom.

Yes, you can. Okay, let's flip this.

Take me.

If I want to take a trip to New Zealand, do you think I'm gonna wait 15 months to save up money to go to New Zealand?

I'm going to say no.

Why?

Because you're. You're way more of an optimist than I am when it comes to money.

Okay? What's the implication? Like, neither of us is running out of money anytime soon.

I'm doing it a smarter way than you are.

I like the confidence. Okay, maybe you are. Who knows?

He's still gonna have a savings.

Maybe not, though.

Yeah, I mean, that's a smart way of doing it.

Saving.

Because you know what? Here's a great way of looking at it, okay? If I do it my way, it's like, I am set now. I don't have to worry because I put that money aside and I'm. We can both totally relax, and we have a lot of money. It's like, I don't care what we spend now because I saved it.

I agree with that philosophy. All of it. When you go on your vacation, I don't want you worrying about eating out, ordering an extra drink, taking a little tour. I don't want any of that. I want you to be able to be comfortable. My question is, you casually mention that. That, oops, I Forgot to include $5,000 a month in net income from this property. You've got. Fine. We added it. No big deal. Like, where's that money going? Couldn't that money be applied directly to the trip? So you would, quote, have enough within four months?

Yeah, I guess. I know I act like I'm uncomfortable, because I am. Because what if I need that money for work? Like, because it's kind of been staying in the. The company.

I know, but, Tommy, you know and I know every entrepreneur knows they need to also take some of that money out of their business, or it will just get sucked up.

Yeah. I mean, I. I. Let me do it my way for a little bit. Okay.

Okay. Maybe. Maybe 10 more years. Yeah.

Right.

No, I mean, this.

This is helping.

Because the one thing so far. Not so far. I mean, a lot has. Has hit me. Your comment about looking back and saying, hey, the memory of going out to eat, the memory of doing something with the kids, that's huge. I mean, that's. That's everything to me. I love that.

Yeah. Let's create a little bit more of those. The fortunate thing is you've actually got the right ingredients here. You have the money. You have a pretty high income. You've been consistently investing for decades. And so everything overall looks great. I am very happy to be able to work with these kind of ingredients. The tricky part here is the psychology. And for everybody watching and listening, you can hear that it is real. You could have millions of dollars, Tommy. You have it. And it's still often hard to really feel like it's enough to really feel like you hit where you need to be. All right, you have zero debt. Again, you have only $14,000 in savings. I just want to point out it's a little bit irregular. It's not that big of a deal. Cause we could fill that up with $150,000 like that, but. Okay, what's your total net worth? Tommy, could you say that number out loud for me, please?

I believe it's a little over 6 million.

Caroline, what do you think about that number? Can you say it out loud for me?

Six million?

Yeah.

What's funny is, like, every time you'd sit there and say, God, I wish I'd win the lottery, and I'm like, well, we kind of have, and we still don't. We still wish we could win the lottery. It's kind of goofy.

Maybe it's not about the actual dollar amount, but it's also about the way you feel about money. And maybe we can use some of the money to help you connect that feeling and build the skill of Spending it. How about that? I know how your finance guy, I know where he came up with that $144,000 or $12,000 a month. He basically took $3,500,000, how much you've got invested, and he calculated 4% of that. That's a 4% safe withdrawal rate. And that's what that got you. Now, that number. That's where it came from. Tommy, you said, I don't know if that's right or not. I don't see any glaring problems with that calculation. It's a very simple back of the napkin calculation. If your money is properly diversified and invested, it's returning about 7% per year. I would safely calculate a 4% withdrawal rate. Some people like to be a little more conservative. They go 3.5 or 3. But with many millions of dollars, you know, you've got buffer. I see no glaring problem with assuming a 4% safe withdrawal rate. Cool. How do you feel about that? Feel good?

Yeah.

All right, cool. Let's not forget that there's also $5,000 of net income a month. There's, Tommy, your income, which, if we were just doing this safe withdrawal rate, you two would be making $12,000 a month, probably in a tax advantaged way. But you also have $5,000 a month. Plus, Tommy, whatever you're making, which is a lot, plus you're going to start getting Social Security and other distributions soon. That's kind of a lot of money.

I guess it is.

Meanwhile, your assets, your portfolio is continuing to grow over the long term. How does it make you feel to hear all this? What is the message you're taking away?

It sounds. It sounds cool, but it's like, yeah, I honestly, here's what I feel. If I go, what you just said, I become soft, it's like, you know, it's. I shouldn't work as hard, and it's going to make me soft, and I don't want to do that. And I know you're going to give me that old man story about some dude who is 72 years old who, you know, what's he going to do with it? What's wrong with that? Makes me feel good. It's like, yeah, I guess I look at it this way, and Caroline will laugh at this, because I hate being pigeonholed by an age, because I feel that I can do almost as much as I could when I was 40, and I strive to do that.

Yeah.

So just to me, if someone said, you know, you don't want to wait till you're 70. I'm like, fuck, I'll be fine when I'm 70. I know I will.

Well, you look like a healthy guy for sure. And I like the, I like the, you know, active guy. I like the fact that you're like, age doesn't define me. One thing that I have learned is it's not just ourselves. It's not like you're the average guy, financially speaking. You're not. Health wise, you're not. But there's also things that happen in terms of a family member. There's external things that happen sometimes that we just can't escape. Here's my point. If you have the money, the time and the mobility to be able to do a few of the things on your rich life list, why not do them now? The idea that it's going to make you soft, that might be true, or it might just be a story you tell yourself.

That's true. I could be just telling myself that I, I have to admit, I worry about the future. Don't worry about the past, don't give a shit about the past. Has taught me a lot. I need to live more in the present day. We can get in the psychological aspect, but I worry about the future. Like, will I have enough? Will I be able to do this?

What do you think we've been doing for the last two hours?

I know, I know and I. And it helps. Trust me. I'm not like throwing this the wayside.

I think we have to have compassion for Tommy here. If you've been thinking a certain way for 30 plus years, you can understand how hard it is to change. And we've heard this same thing happening on multiple episodes of the podcast. We've heard couples come on and one of them has trouble changing, even though they, their own attitudes and behaviors are not serving them. But it is simply hard to change. That is human behavior. So I think we need to have a little bit of compassion. And it becomes even more notable because if your attitude or behavior has actually made you successful, it's 10 times harder to change. Think about it. Tommy has saved diligently, he's always minded his money carefully. That has made him successful. And now you're asking him to essentially change that. I wouldn't say it's as far as cutting off a physical limb, but it is certainly changing a part of your identity. And if you can think about somebody coming to you and taking a part of your identity that you treasure, you're funny. And I go, don't be funny anymore. Be like the trolls who try to come at me on Twitter.

They're not funny.

Be like that.

You'd be like, no, I'm not gonna do that.

That's what Tommy's going through right now. But the fact is, it's not serving him anymore.

I know this sounds weird, but I'm thinking, okay, by hearing from my trades, hearing from my clients, hearing from past clients, oh, he's not working as hard or he's not doing that, and that would bother me. It'd be like, here I go. I shouldn't have done that. Now I got to get back.

You want some help on how to deal with that?

Sure.

Do you?

Yeah, I guess.

Okay, let's say that somebody says that. What would your natural reaction be?

I'm being honest. I'd say, fuck you. You know? What are you saying? Prove it.

Yeah, fuck you. I'm coming back, and I'm going to work twice as hard. And they'll see it. Fuck them.

Yeah, right?

It is.

I know. That's pretty whacked.

No, it's right on brand. It's exactly what I expected. Part of that is what got you here. You bust your ass, no one's going to ever see you as not putting in the work. They know you. That is your identity. I respect it. I think that sometimes identities are like layers. We can add on layers and we can remove layers, and we actually have more control over those layers than we think. What if just we try on this layer for a second? They said, oh, you know, Tommy used to be so responsive. He just doesn't answer my text anymore. He's losing his edge. And your response might be something like, hey, I'm so sorry to hear that. You know that I love every one of my clients, and I put you first. I've decided that I'm going to be spending more time with my family. But you're right that it's totally unacceptable for you not to get a response. I'm going to fix that so that you will always have one point of contact in my business who will respond to you within 24 hours. How does that feel?

That's a good answer, because I'm pretty good at putting together those kind of scenarios.

That.

That was a good one.

You put your client first. You acknowledge them. You even admit that was unacceptable, but you do not apologize for putting your family first.

I love doing that. That is what I do in earnable. We workshop your business ideas together. I do it live with you. I help you understand the psychology of your customers. I even script out what you can say to them. So if you are interested in earning more in starting a side business, even if you don't have an idea, we workshop that how to find a profitable idea. And every time I do this live, we have business owners in there who are already doing pretty well, and they want to know how to take it to the next level.

So I will put a link for.

The earnable program in the show notes.

I would love to see you so.

I can help you workshop just like I helped Tommy do it. Right there.

If you ever have scenarios like this, you know, I love doing this kind of stuff, but really, that gets to the core of your identity. I have no doubt you can come up with 20 answers like that on your own. You're very good socially, I can tell. But it's about you being able to say, I'm adding on this new layer to my identity. It's not going to take anything away from who I was. It's just going to add a new layer of richness to who I am. Would you be willing to explore that?

Yeah, I like that.

All right, that's cool. Caroline, what do you think about that?

Absolutely.

That's cool.

I did a couple of things there. That layers concept, I gave him a new framework that he can use. So if he finds himself feeling tension at having to change his identity now, he has some language that he can use to describe it. I actually would not be surprised if Tommy finds himself saying, oh, I'm trying on a new layer of my identity this week.

Okay.

Second, I gave him some specific words to use for a very real situation that he's worried about now. Remember, they came to me asking if they have enough to retire and how Tommy can feel a little more comfortable spending. How did we end up here scripting out his conversation with a hypothetical customer? Well, the answer is, as you start to unpeel the layers of what the real issue is, you discover these tiny little objections or reservations that somebody has. And from the outside, they seem so irrelevant, so small, but to that person, they are huge. They're absolutely huge. And so Tommy clearly is concerned about what his customers will say if he's off traveling around the world.

Boom.

Let's acknowledge that that's a real concern for you, Tommy. Let me show you the exact words to say. And once somebody gets one roadblock off, then another one off, hopefully they start to see that this is possible to change.

So my hope is that he can.

Tackle this, and then he can start to realize, oh, I can do this with one thing. I can do with many Others. I wondered what else Tommy and Caroline have talked about doing together.

Okay, well, he's talking about the New Zealand trip. I want to go to Italy. So maybe we can go to Italy in September.

Oh, wow.

We can go do New Zealand in January. February.

Okay. Talk about it. How would you decide on that decision? Have the conversation.

I'd like to plan a month in Italy. What do you think? I mean, I don't ask for much, so it's hard for me to even say that.

I. I'm great with that. I. I want to go.

Yeah. That's it. First of all, this is awesome. I love the discomfort, by the way. Your discomfort is my pleasure. Okay, Just so you know, now that's it. That's all you need to say before you go off and plan the whole thing.

Well, he'll probably want to know the expense, so I'll have to figure that out.

Why don't you two talk about it right now?

I.

Do you. Hold on. Do you think he actually. He didn't say that. Why do you assume he wants to know about the expense? Let him say that.

I guess so, normally, yeah, I think I would say to him, like, what. What do you think? And. And. And I'm thinking the same kind of money that we spend in New Zealand.

That's a lot. I don't think we need that much.

Why would it be more expensive in New Zealand versus Italy?

Hold on, hold on, hold on. There's so many things I just want to. I'm going to add my commentary, okay? This is my dream job. So first of all, that's a very nice tree you have behind you. You don't need a tree like that. But you still got it, didn't you? Yes. All right. You got a lot of nice stuff. You don't need it. I don't need Whatever, but I still got it. And I don't think either of us are highly materialistic, Tommy, but there are certain things that you mentioned yourself. You want the memories, the meaning. So instead of reacting with your instinctive reaction, which, when it comes to money, is what?

I gotta think it over. I gotta make sure we're good. I gotta analyze it.

Yeah, let's. Let's give a name to that little.

Little guy on your shoulder.

Who is it? What? What. What's the person's name?

Dickhead?

I don't know. Okay, did not expect that one. All right, little dickhead is over here. And what is little Lil D. Wearing? What is he. What is he outfitted in?

He probably looks like an accountant.

That's a good one. So what is he? Describe that for me.

You know, a straight lace guy saying, hey, you know, going like this, holding their. You know, rubbing their fingers against their chin like, you know. You sure?

What else does?

Think about this.

Keep going. What else?

Because this doesn't make a lot of financial sense.

Now.

Yes, you know, maybe go to Italy, but maybe you don't need to spend that much. Maybe we get a better deal.

Yes. Loves deals. This person's on, like, Orbitz or Expedia. Oh, have you considered this? What if you took the connection, the five connections on the way to Rome? Yeah. What else does this person say?

I'm not doing that.

They won't do that. We'll fly.

Give me a little bit of credit on something. I told her. I said, hey, I've been thinking about this New Zealand trip, and I want to go business class. What's her response? Well, of course it's really far.

Okay.

I'm thinking, what?

Okay, okay. We'll come back to that. I have a little coaching that might help with that conversation, but that's a cool conversation. I'm proud of that. So, little dickhead over here dressed like an accountant and always telling you, I don't think you're going to need that. Let's run the numbers now. Who's the other person on your other shoulder?

Mr. Chill.

Mr. Chill. What does Mr. Chill look like?

Maybe like the Big Lebowski.

Okay. Okay. Very good. And what does he say to you?

Just relax, man. You got it covered. It's all good.

Is Mr. Chill going to let you spend your way into running out of money?

I hope not.

No, he's your. He's your guy. So you can decide what he does. He doesn't have to be the guy who gets you bankrupt. It's your Mr. Chill. So you tell me, is he gonna let you go that far? No, I don't think so either.

No.

Mr. Chill is not Mr. Spend it all on yachts and stuff like that. Mr. Chill is more saying, what?

Have fun. Have fun, man. Just if it means you're going on a kick ass trip. Have fun. Go to the best restaurants. You're staying at some good places. You're not worrying about how you're going to get there because you got it off. Your travel agent has it all figured out.

I'm loving watching Tommy and Caroline's face as they go through this moment. You should see, it's dreamy, it's aspirational, and most of all, it's fun. This is how money is supposed to be. This is how it can be for Tommy and Caroline and for you.

Love it. Love it. And one last question. Each of them is holding something in their hand, Something that really demonstrates their worldview. What is little d holding in his hand?

My first visual was probably holding, like, you know, you read about teachers when they're really old, this big stick, like, whacking you on the back of the head or back, saying, you better think about it. And, you know, Mr. Chill's probably. Oh, he's got a Brian Alaskan amber in his hand and. Or pina colada, something like that.

Yeah, yeah. I'm thinking he's got the pina colada and he's got a camera or a little photo book, and he's just going like, this is what you're going to create these kind of memories, right? What do you think about that?

I love that part.

Yeah, I like this a lot. Especially for you, because you have these voices now. You've given a name to them, You've given a look to them. You even know what's in their hand. You got this guy, he's having his drink. The other guy's got that punitive little stick. And when you have these conversations right now, this guy, Mr. Punitive, he comes out, or little, as you call him, he's your first reaction. But you have the choice on who to listen to.

Now, here's the trick.

They're not going anywhere. They're both going to be there. My advice to you is not just get rid of one of them, because that's not going to happen. They are with you. They are part of you.

But you get to choose who to listen to.

Okay. And it's kind of nice to have a balance. But right now, would you agree they're a little out of balance?

Yes.

Okay. Okay. So. So let's try that whole last thing again. Caroline, you mentioned that when it comes to Italy, you have a general target budget in mind. Go ahead, bring it up. And Tommy, when you react, well, let's see what happens.

Okay, so I want to go to Italy for a month. And I. I'm thinking it's going to cost us around 20,000 with all the tours and going out to eat, nice places we'll be staying at. What do you think? I'll figure I'll have a portfolio for you, but I don't have it at hand. So maybe I think that's.

I mean, I love Italy, so I jump on that. Well, you know, I love traveling, so I'm good with that because I can ramit. Don't get mad at me for saying this, but I will be able to save for that. I'll do that. I like saving. It's okay.

Look, I'm not here to get mad at you. I'm here to help you listen to that voice. Okay. I really like that you said. Yeah, I can get with that sometimes. Look, you're still going to have a little bit of that accountant in your back pocket. It's never going to go away. That's okay. If you feel the need to have a little document where you write down, okay, I need to put aside $2,000 a month. Dah, dah, dah. Okay, but part of changing your dynamic sometimes is to start with the behavior first and often the attitude follows. You're figuring it out together versus I'm saying this and you're saying that. And like, why you're multimillionaires. Why the fuck are we arguing over $10,000? It makes no sense. Yes, let's argue about I want to go to this restaurant and you want.

To go to that.

Okay, fine, we'll do them both. But we're going to do one on Tuesday and one on Thursday. That's a cool argument. Yeah, right. We don't actually have to argue anymore.

We won.

In my mind, I'm not telling you to go drop 500k on anything. I don't even want to talk about that Florida condo. I don't think you should get it in the next 12 months. I think you should work on building up the skills of spending money first. Both of you should feel good.

You should come up with some conventions.

For how you're going to make decisions about money. Certainly if you want to go get an Airbnb, go get it. I would hold off on anything that big, but trips like Italy, New Zealand.

Dinners with the kids, It's a no brainer.

That should be getting done. That is a skill. It is time to build right now.

So what you're saying is next September, or is it this September? Are we going Italy? Well, it's.

Well, it's the one coming 2024. Whoa, what? Wait, 2023? That.

That.

Yeah. The coming September. Yes.

So we should do Italy. This.

Yeah, exactly. Yeah, absolutely.

Yes.

Okay.

Are you cool with that, Tommy?

Sure, why not?

Okay, that's cool. There you go. That's Mr. Chill Talking.

I don't mean this in a bad way, but this went way better than I expect because I didn't think you're going to tell me much at all. I'm Just being honest. I. I do have a better perspective. You know, you didn't tell me, hell, you shouldn't be saving. You know, that type of thing. You just gave me different perspectives. And I love looking at different perspectives, love seeing both sides. And then I will decide what works best.

Look, I was never going to convince.

In one phone call a successful 60 year old man what to do with his accumulated fortune. He's made it this far on his own, and I'm totally fine with his needing to make the final decision himself. What I hope happened is I gave him some new ways of looking at his money. I pushed him in a way that probably nobody around him pushes him. And he had to respect some of the things I was saying because I know the numbers. I also gave him these frameworks that he can use little people on his shoulder, which he can reference as he naturally responds in a way that he has honed over 30 years now. Tommy and Caroline both sent follow ups. Let me read them to you. Tommy said, I've learned that it's okay to say the following to clients, quote.

I've decided to spend a little more.

Time with my family.

However, I will still give you the.

Attention your project deserves, and I will.

Be continue to be available to your needs. Caroline said she learned each time I.

Want to plan something with Tommy, I should bring it up as a memory instead of money.

Wait, that's it?

We talked for that many hours and that's the conclusion? Tommy, your conclusion was how to talk to your clients?

Oh, okay.

Tommy also did say, quote, we're planning on spending a month in New Zealand.

In January or February, 2024. Okay, look, I'll take what I can get, okay? Sometimes I guess if you're 60, you're gonna do things your way. All right. In a way, I find it hilarious. I mean, we spent hours talking about money, psychology, and Tommy's conclusion was how to deal with a hypothetical problem client. In any case, I really appreciate Tommy.

And Caroline, both of you coming here, sharing your numbers, sharing the way that you talk about money. You can clearly see that there's a lot of love there. And you can see that Tommy does want to travel more.

He.

He enjoys the memories. There's a lot that he has to work through. Caroline, I know you've been very patient. I know that with your upcoming retirement, it's going to become even more important for you to start living your rich life. So my hope is that the two of you can really create a language and a habit to do it together. Thanks for listening. To I Will Teach youh to Be Rich. I'm Ramit Sethi. Please follow the show on Apple, Spotify, or wherever you listen to podcasts. If you haven't read I Will Teach you to be Rich my book. Pick up a copy. You can get it at any bookstore or any library and it will show you the specific tactics for how to build the I will teach you to be rich system into your personal finances.