“We’re worth $1.25M, so why is he afraid to get a $15 gym membership?”

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I find finance discussions intimidating, threatening, almost at times awkward. I'm very avoidant to the conversations.

Jesse is not a planner.

Jesse was. You agree with that?

Yes. I'm very fly by the seat of the dance.

How would you describe the way you feel right now?

Mad at myself as I don't think I realize what I created.

What did you create?

An environment where, you know, Jesse doesn't see the big vision of what he's capable of doing. I'm sorry, Jesse. Love you so much. But, like, it's so clear that you're so anxious on this conversation the deeper we get in because, like, you're using, like, buzzwords to try and, like, talk effectively instead of just being like your yourself. I want Jesse to be interested in what we're doing with our money. And I feel like I. I created that. Like, I've created this dependent relationship that's not. It's not sustainable.

Meet Stacy, who's 37, and Jesse, who's 38. They've been married for 11 years and they live in Canada. What makes them fascinating is not the fact that Stacy makes five times what Jesse makes. It is the dynamic between them. For example, when they got invited to be on this podcast, they first attended a screening call with my producer. And here's what Stacy wrote. I booked time Thursday for the screening call and added my husband Jesse's email to the invite. He may be able to join, too. This is actually a huge red flag. We require both partners to be on the call. We state that very clearly. So the fact that she took the lead and said he may be able to attend got our antenna up. How would you handle it if you had a relationship dynamic where one person took the lead on everything and wished that the other would get engaged? You can watch this entire episode on YouTube and I always love to do that because it lets you see their body language and facial expressions, which gives you a whole new insight into the dynamic between the two of them. All right, let's get to it.

The day I applied to go to the show, to be on the show was a day where Jesse and I were arguing around. He was debating to get a gym membership. So he's had some physical ailments in the last couple of years. His physiotherapist recommended a gym, or rather, a treadmill. We didn't want to buy a treadmill to fit in the house. So there's a gym near our house and near Jesse's business that he can easily go to. It's like 15 bucks a month. And he hemmed and hawed about, like, whether we could afford it. And I was like, we're not poor anymore. We can afford that. It made me realize, A, he doesn't understand that, and B, that such an insignificant amount of money per month. He felt like he had to figure a way around not spending it instead of just talking to me about the expense.

And so what happened?

We had, like, a discussion about it, and I was like, we're not poor anymore. Like, you can get this. And I think it still took him two weeks to actually buy the gym membership.

When you said, we're not poor anymore, what was Jesse's response?

Yeah, I think. Yeah, I know, but.

But what?

Like. But, like, I can figure out a way to, like, not spend this money, or maybe I'll look into cheaper options, but I'm like, you're not really going to find a cheaper gym. It's already a discount gym.

A lot of very sensible reasons. Did it work?

Yes, but it took him a couple. I think, a couple weeks to. To buy it and, like, pull the trigger.

Jesse, what happened in that conversation? What do you remember? The first glimmer of the treadmill discussion.

Being I drag my feet on a lot of, like, random expenses because I'm always trying to save money. I just have it in my head that. Well, I mean, I don't personally make a whole lot, so I feel like the household doesn't necessarily make a whole lot, which is not really the case. So about a week later, I did finally pull the trigger. Got the membership. And I've been trying to do as much stepping or walking. Sorry. As. As I can.

Cool. I'm glad you got the membership.

Thank you.

Would you consider that discussion or series of discussions a success?

Yes. Oh, 100. I still try and tighten my belt, and to Stacy's point, I do it nonsensically at times as. As this instance was, I'm just very uncomfortable spending money.

Always been like that?

Yes. Yeah.

All right, gotcha. When you eat Out. Do you eat every single thing on your plate?

Yes.

Your parents taught you that?

My father? Yes.

What did he say?

Oh, God, a lot of like, father esque things like if you don't eat that, they're starving children in Africa was a very common line. Oh, God, you can't leave the dinner table till you're done, that sort of thing.

Okay, okay, cool. All right, I got it.

I don't even like spending money on public transit. If I, if it's within, you know, tens of kilometers, maybe I'll bike. It doesn't matter weather or anything. Just to save myself six bucks if it's raining. I think a more rational person, I feel, would probably just spend money for public transit, whereas I would prefer not to.

Got it. All right. Hearing what you just told me, Jesse, and really listening to yourself and what you just said to me, do you hear any themes?

I noticed that I'm very. I don't want to say miserly, but that's probably a really good word about it to use.

Miserly means what.

I want to keep, what possession I have because I don't, I don't have. Yeah, Mars Lee is a poor word because I don't, I feel like I don't have a lot and for the longest time I didn't. We're somewhat better. I don't have a very steady income for the past year because I just started a new business. So it's been really messing with my brain on how much funds we have available to spend.

So what else do you notice about your answers to me? If you were like a scientist examining the transcript of what you just told me, what would you note?

That I'm uncomfortable spending, nervous, Uncertain.

Because he's not involved in the finances, he doesn't know where that threshold is. He still thinks that threshold for what we can spend was the same when we were in our early 20s. I want Jesse to be like, I'm getting this Gym membership, it's $15. This is the decision I'm making. And just buy it.

This is what I mean when I say focus on the $30,000 questions, not the $3 questions, or in this case, the $15 gym membership questions. Jesse's gone for such a long time agonizing over whether to join this gym all for $15. Imagine the costs of worrying about a $15 purchase and all the opportunities that you're leaving aside. And with people who worry about tiny questions like this, it's never just one purchase. In fact, with Jesse, there was a worn out bag that he didn't want to replace. There was a desktop computer that he used until it completely failed. He bikes or walks around town to save $6 even when it's raining. My point is not that you should just spend money on everything. My point is that some people live their entire lives trying to spend as little money as possible, and that has significant costs.

I was 18, just in my first year of university and just 19. Yeah. No money.

No money, no money. I was a musician dropping out of college, going on tour.

When did you start to make some amount of money, A comfortable amount of money?

26, 27.

So let's go back to when you were in your early 20s, even 25. 26, 27, when you would talk about money. What were those conversations like?

Our roles were very much reversed because Stacy was in school until she was 24. 25. 24, yeah, 24. And I had a full time job just in retail since I was the, I'm not one for talking finances and I was the one with all the funds. We really didn't have a lot of conversations back then because we stayed in a really, really cheap apartment. So it wasn't that difficult to live the life we wanted without actually thinking about anything.

And it seems like you were on the upswing with your income at that point as well.

Okay, yes.

All right. So at what age did the roles reverse where you, Stacy, started making more money?

27.

So you started making more than him. What changed when you started making more than him?

I made the life decisions like anything that was a financial life decision. So we had this huge lump sum for a down payment and then we went to find another home. I made the decisions around how we saved for that, how much we put down.

And did you get Jesse involved in those decisions?

He's shaking his head. I'm like, I don't remember. Probably not. Probably very little. Yeah. It's more like I, I do all the homework.

Who is the one who tracks the spending, makes sense of the spending, manages the spending? Stacy. That Stacy. Okay. Who's the one who plans investments, decisions about big. Okay, that's Stacy. So, Stacy, you do everything with the money?

Yes, everything. So I'm like very much a type a planner, organized.

You don't say?

No. Shocking.

So you do the homework. What does that mean, homework?

We had a lump sum of money.

How much?

I said, can't remember. 200 grand. You know, it was up to me to figure out like, where could we find afford a home? What was going to be the best value so that we could Live the life we wanted to live.

And it was up to you. Because what?

Jesse is not a planner.

Oh, Jesse, would you agree with that?

Yes. I'm very fly by the seat of the pants.

And Jesse, what is your role as it relates to money in your relationship?

Not a lot.

You know, I once remember I hired a consultant when my business was in trouble, and he came in, he took a look at all the numbers, and he said, tell me what you were doing when your business was at its peak and tell me why you stopped. So I walked him through all the initiatives that we used to do, and I laid out all the very rational reasons that we stopped it. The cost of revenue was too high for this program, et cetera. He gave it some thought, and he said, I recently spoke to another CEO. Business is also in trouble, and he had very good reasons for every decision that he made, just like you. But you can have all the right reasons and still get the wrong outcome. In Stacey and Jesse's case, they both have stories that are not serving them and certainly not getting them the outcome they want, or at least Stacy wants. Stacy describes herself as type A, which, by the way, is not really a thing. And they both agree that Jesse is bad with money. But how would they ever know? They've never really given Jesse responsibility and accountability over money itself. You grew up poor or lower middle class?

Lower middle class.

And what about you, Stacy? What did you grow up? You grew up the same?

Yeah.

Yeah.

Are both your parents together or they separated?

No, they separated when I was five.

Yeah. Who'd you live with? Primarily, my mother. Okay, and what's your mom like?

She is also very cautious about her money and spending.

We both were raised by immigrant mothers, and we. We were both raised to be like, make the most of what you have, work really hard to have what you have, and, like, don't take stuff for granted. Jesse takes that really to heart. And I think I'm at a point in my life where we. We were both like that. I think we're on the same page. I don't think we'd be where we are today if we didn't have that mentality when we were younger.

What do you remember her saying about money growing up?

Well, we didn't, like, enjoy anything. Like, we didn't go on vacations. We went on one my entire childhood. Yeah. Like, my parents sacrificed a lot so that they could help pay for my university. But I'm proactive. Where. So my. My mom and I think my dad, who are still together, they think life Happens to them. I think I control my own destiny, and I've lived my entire life with that MO. So where'd you get that from? Flight or fight mode is like, what I live in constantly. So I'm always thinking plan A, B, or C. Do you have siblings? Yes.

Are they the same as you?

Yes, My brother. Yeah, I have one brother, I'd say. Yeah.

So you both have taken control of your lives. You sort of carved out your own path. And would you say that your parents are still more passive?

Yes.

Wow. That seems to have hit a nerve.

Yes. Bless them. But they are. They drive me crazy.

They're passive. Like what? They don't want to confront any issue. Restaurant sends the wrong thing, they just take it. They never send it back. That kind of thing.

Yes. They will get taken advantage of. They are retired, but, like, don't take advantage of, like, their retirement. Yeah.

How are they doing financially?

I don't know.

Why? What?

They don't. They don't tell us.

What?

Yeah. So I think.

Do you know how much money they made when you were growing up or whatever?

Yeah, I'd say we were, like, lower middle class as well. My dad worked for the government, had, like, an average salary, and it was just him. My mom stayed home.

So you decided to take control your money, you're on top of it. How many different Excel spreadsheets and budgets do you have? Tell the truth.

One Google spreadsheet. But it probably has 20 hidden tabs over the last 10 years.

How'd I know that?

Yep, there's.

And how diligent have you been in tracking your spending? Let me guess. Extremely. Go ahead.

Correct. We both have used an app that I love for the last 10 years to track every expense. Anytime we swipe our credit card, it goes in. And I trained Jesse to do the same thing.

Jesse, you do that?

Yeah.

Wow.

I am not as diligent as her, but, yeah, it will track down to the penny, even on cash.

And what does that get both of you?

It's very satisfying for me to have the data to tell me what we're spending on. It actually helped us when we were filling in the conscious spending plan. Like, you mean when you.

You personally were filling it in?

No, no, no. We did it together. We did it together.

What?

I don't believe that 100%. To be clear, she filled it out once by herself prior to having the conversation with your coworker.

That's not doing it together. What are you talking about?

But we did do it together.

Again?

Yeah, again.

Okay.

Before she Told me we were appearing on this podcast.

All right, fine. So you track everything you're tracking, like the price of Brussels sprouts over time, so you can trend that for from.

2010, but, like, how much we spend on groceries per month, you know, clothing, transportation.

How many categories do you have?

More than we should. I like how many.

Tell me, tell me.

Hang on.

She's gonna pull it up right now. This is amazing. Oh, my God. Look at that. She's like, finally. It's been 13 years, and finally someone asked me a question about my app. Okay, tell me, how many categories?

Do you want subcategories too, as well?

High level categories?

No, I want all of them. Don't. Don't BS me. Oh, wow. She just took, like, a deep swallow, probably. Everybody watch. However long this takes, I'm going to run completely dead air. I will burn literally gigabytes right now just watching them. Look, he's still counting. This is unbelievable.

32.

32 cat. Wow. So simple. You ever hear me say that phrase, fight for simplicity in your finances? You ever heard me? Yeah, she's going, yeah. She goes, yeah, that's a great phrase. I chose not to adopt that. That's great for other people, not for us.

I'm learning. I'm learning.

Okay, this is hilarious, but also fucking insane. Tracking four categories, like in my conscious spending plan, is good. Tracking 32 categories is absolutely bonkers. And it gets you nothing. Correction. It gets you a sense of control, but does not actually get you closer to your goals. There's an epidemic of us doing things that make us feel productive but actually accomplish nothing whatsoever. And tracking 32 categories is a perfect example of that. And you can tell because when I asked what they got out of it, there was a very long silence. Their tracking. Excuse me. Her tracking is more like scratching a scab off a little tick. That makes her feel better in the temporary moment, but it's certainly not giving them the information as to how to save, how to invest, how to spend their money going forward. It's not serving them. But because she obviously takes a lot of pride in this, it's now become a part of her identity. So what changed?

Two years ago, we went to couples counseling because of this. It was heavily influenced by. By. By money and finances and stuff.

Okay, good. I'm glad to hear that you did that. Has that been helping?

Yeah.

Yes. Oh, yes.

I think we still don't have the tools in our toolkit to communicate effectively about money, because I feel like I'm always pulling Jesse along. I want Jesse. To be interested in what we're doing with our money.

Okay. That's honest. I appreciate that. And, Jesse, what do you want, in your own words.

To be less uncomfortable with money.

Can I ask a couple questions, Jesse?

Of course.

Do you want to be engaged with money in the relationship? Deep down?

No. I find finance discussions intimidating, threatening, almost at times, awkward. I'm very avoidant to the conversations.

Are you avoidant in other parts of life?

Yeah, I avoid confrontation quite a lot. Hmm.

Have you made that connection before?

Yes. Oh, yes.

All right. So deep down, you don't want to engage with money, that's what you're saying?

Yes. That is like my base. But, you know, through counseling, through talking for years, I know that that's not productive, and I would like to change. Okay.

What's the consequences for both of you if nothing changes?

A lot of. Probably a lot of resentment. Maybe divorce.

Yeah, I'd say. I'd say resentment. I've felt that before. The life we've kind of set up in the last year is I handle the finances and work. Like, Jesse works too. My job is bringing in the income, and Jesse takes care of the household, social engagements, groceries, the things we need for the home. I think the other thing, too, is we started to talk about, like. Like planning our rich life. Like, what are our goals? Because when we were younger, it was just like, get a home. It was such a big goal for so long. Now it's like, what are the goals we're going to have for the rest of our life? Okay, we want to do this by this year. How do we work backwards from that? And I find that I'm the one who always is figuring out how to work backwards from that. I'd like to see a little bit.

More input because it would mean what?

I'm not the only one creating the life we want.

And if you're the only one, what does that mean?

I just don't. That doesn't feel like a relationship.

What is it?

It's like, once. It's like. Like we're roommates. Like we're not creating our life together.

She's very much just dragging me along for the ride.

Are you enjoying the ride?

I would be lying if I said I. I wasn't enjoying the. The comfort of that. She is. She has given us because she makes considerably more than me and is, you know, infinitely better at finances than I am. But I don't want it to. That to be the status quo.

Are you uncomfortable in any other parts of life? Parts of life that you're good at. Like, last night, I went out to eat Indian food. Okay. And I got it really spicy. So when I eat really spicy food, I start to sweat a lot. My eyelids are sweating. The back of my head is itching. I'm, like, wiping away, like, lots of sweat. Right. I was physically uncomfortable, but I also love it. I'm good at it. I know how to eat Indian food. There are parts of life sometimes that we are uncomfortable at, but we're good at it or we enjoy it. Do you have any parts of life like that?

Yes. So as a musician, I am a very crippling stage fright.

Okay.

And at least I would like to think I am very good at performing.

Wow. A great example. I couldn't have named a better one myself. So stage fright, that's very uncomfortable. But somehow you still get up there and you perform and you do well, right?

I'd like to think so, yes.

How about you just say yes?

Yes.

Love it. Okay. So is it possible that you might feel a little uncomfortable with money and you might also be a very good participant in your relationship?

Yes, I hope so.

Okay, how about. Let's try that again. Is it possible?

Yes.

Okay. I agree. I agree. It's okay to be uncomfortable when you're first starting to learn about money, talk about money, think about money differently, and you can be a good participant.

To be fair, it was a rather important decision that I had to partake in because I had to close my checking account in order to join hers. When we. When we combined our checking accounts, we.

Think of our money as like a communal pot. It's not like Jesse pays a certain percentage based on his income versus me.

Who made that decision, by the way.

We've always done it that way since we were poorer.

I do believe it was your decision, though, when you joined accounts. Yeah. Back. Back in 2012, I believe.

Guy pulls out receipts.

Part of what I do. I had an old boss that said, the art of what I do is facipulation, which is I facilitate, but I'm really manipulating people.

That's so interesting. Any connection to what's going on here? Anyone? Okay. Do you see my point?

Yeah.

You take something and say, here we go. This is what I want to do. And you even use words like, this is what we want to do.

Yes.

We set a budget.

Yeah, I know.

Is it working for you?

Well, I. I'd say the budget has worked pretty well. We do pretty well with our lives. The unintended consequence was Jesse's passive viewer versus a participant.

Do you want him to be?

No.

What role are you playing in Jesse not speaking up forthrightly about what he wants?

Well, because I'm in control and probably because, like, we've been together for 18 years. Just our life is an example. Jesse makes what, 20% of what I make. So, like, the life he has is from my labor, you know?

California has had a drought for many years, and this year, suddenly there was a ton of rain. And all of a sudden, people realize that California is not capturing the rainwater. The water just flows right out to the ocean. And everyone said, what we need to capture this rainwater? Well, the system was designed decades ago to get rainwater out to the ocean as quickly as possible. And guess what? That is exactly what the infrastructure does efficiently and quickly. Like California, Stacy is getting exactly what she designed for careful tracking over their spending, which she does. Total control over their money for her decisions they ostensibly make together, but she really makes. She's getting everything she designed for, except the one thing she claims she wants for the two of them to do it together.

If we both have goals, I want a partner who participates equitably in achieving those goals.

Do you know if he has goals?

Jesse, do you have goals?

I have. I have goals with my business. And that's. That's about it in my life at the moment. I'm not sure what else to say.

What do you think hearing that, Stacy?

It's a symptom of, like, Jesse doesn't really, like, think ahead and just kind of like, life happens day by day. We'll figure it out.

Why does that concern you?

Because then you're never thinking of, like, how life can be better. I try and, like, get Jesse to dream bigger because I try to get.

Him to dream bigger. How do you do that?

By providing. I have worked really hard to provide a life so that he doesn't have to worry about money as much, so that, like, he can do something more adventurous. So he just started a business last year, and I, like, encouraged him to do that because he was working retail. And I'm like, you can't work retail forever.

When you say to him, you can't work retail forever, what message are you communicating to him?

I'm probably communicating that, like, the path he's chosen is not ideal or, like, it won't lead to success. It, like, won't make you happy forever. It'll wear you down. It was wearing on his body.

Did. Do you think that he knew that deep down that retail was probably not good for him physically?

Probably deep Down.

But he wasn't making a change, was he?

No.

And so you decided to what, shove.

Him off a cliff?

Well, let's ask Jesse. Jesse, take us back to the time where you were working retail. How much were you making back then?

65K at the very end. Okay.

And did you enjoy the job?

I enjoyed the job up until covet happened. And then we basically became a warehouse. Even though I was retail management, they basically treated me like a workhorse, and I broke my body.

Are you still recovering from that now?

Yeah, two years later still. I'm on the better end of it, but yes.

I'm sorry to hear that. So you were kind of put into this labor role, and that was tough on you. How long did you do that for?

6 years. In that one position for that one company? I had been retail for two decades.

Okay. Oh, you've been retail for two decades?

Thereabouts, yeah.

Okay. Did you enjoy it for two decades?

Yeah. I thought I was pretty good at selling stuff.

Great. And what would you say to her about your day at work?

Of course. So as Stacy's already familiar, but I'll say it again, my manager at the time didn't come in today, called out, and I had to do her job, my job, and probably 10 other jobs. And I'm not getting paid for this. And I've complained to her boss about this for the umpteen time, and nothing is changing.

Stacy, go ahead and respond the way you used to respond.

Have you tried?

Oh, that's all I need. That's all I need. Thank you very much. What do you notice is happening in that dynamic?

One person is venting. One person is trying to problem solve.

Imagine that someone shoves you one time, 10 times. Imagine they shove you for 18 years. At a certain point, it becomes hard enough to even remember how to walk on your own.

Yeah.

You think that might be happening here?

Yeah, I think you hit the nail on the head.

You two are talking past each other. Stacy's looking off into the orbit right now. She's realizing, I did this today.

You did it today.

I'm pushing him off the cliff again. It's highlighted that I have, like, years of habit to. To break.

You see the issue? You have no fingerprints on your finances at all. You're merely a passive observer in your financial life. And she doesn't like it. And if she gets hit by a bus tomorrow, you're. Actually.

He's not that.

That is the conversation we've had.

What do you mean? He can get a big old life insurance check that doesn't mean he's going to know how to use it.

That's true.

Stacy controls everything financially related in their relationship and therefore disempowers Jesse. When Jesse has a problem, she tries to solve it, thus further disempowering him. This is a classic example, only it's usually with the genders reversed. And Stacy really has a massive blind spot around how she's helping Jesse. Even in the last comment where I pointed out that Jesse would be screwed if she got hit by a bus, her response was actually not. She really believes that handing over a check from her life insurance would help Jesse, who's functionally unable to deal with money in his 30s. Her disempowerment has lots of costs that are totally invisible to her, but I think she's starting to realize them. And Jesse plays a part in this. He's sitting back, relaxing. Stacy's running around tracking 32 categories. Why would he change? Life is good. The dynamic is really what stands out to me. So in order to understand it more, let's take a look at the numbers. Their combined gross monthly income is $19,867. Their gross annual income is $238,000. Assets, 1.32 million. Investments, 319,000. Savings, 50,000. Their debt, a mortgage, is 435,000, therefore bringing their net worth to $1.1.25 million. How do you feel about $1.2 million in your 30s?

I think I've done very well for myself.

Okay.

And I hope to grow it further in the next 30 years.

Good. All right. That's a good answer. I love that answer. It's very confident. Did it feel real to you to say no?

A lot of it is in our house, so not a whole lot of is liquid.

So what does that mean?

When I say the number aloud, My first thought is, wow, we're doing pretty well for our age, where we're living. But then my second thought is, not a lot of it is accessible or usable, even in retirement.

You like to worry?

Less so than Stacy, but yes. Still.

What do you get out of it?

Out of worrying?

Yeah.

I. I worry a lot that what you had just mentioned, and Stacy and I have had that very same conversation many times before, that if she suddenly is out of the picture for whatever reason, I am in a lot of trouble.

Because if she were hit by a bus. By the way, I love this morbid conversation where we're talking about one person's premature death who just happens to be sitting right in front of Us, we're okay.

We're both European. We talk about death a lot.

Fantastic. All right, great. So if she were to get, you know, hit by a bus, you still have $1.2 million and you're a young, able bodied guy. So it's not the number that concerns me, it's that everything beneath it, which is you would have no idea how to manage it on a day to day basis. No idea how life insurance works, no idea what investments are or how they interact with your savings. None of it. Would you agree?

I would agree. And more to that effect, I also don't even have a lot of working income because I just started a business in a market that is not known for making any money.

And how long are you going to go on that business before deciding if it's worth it or not?

Ideally until retirement. The, the goal is to grow it through expansion.

Okay, great. How much do you need to make.

From this business in order for me to like, maintain what, where we are now?

I don't know, just how much do you, do you have a goal for how much you're going to make with this business?

My goal is to double that within the year.

4,000Amonth. Okay, that's good. And would you be happy, would you be satisfied at that number?

I would, yes. But again, that is, I would be happy with that number if I still have a loving and, and a healthy wife.

All right. Stacy, do you see what the dynamic that you have co created has done here? She's nodding. Say it out loud.

I think what I heard was one, I don't like if Jesse does not have the means to manage financially if I'm not around. And then two, what I heard is with regards to his business, just like small goals, a small sense of what could be.

Yeah, like 4,000amonth. While impressive for a business to start, I mean, Jesse used to make 65,000 in retail. Like, shouldn't a business make more than you can make working retail? Jesse?

Yes.

I'm not blaming you. You haven't been given the authority, you haven't been given access, you haven't even been encouraged to take control of some of these aspects of finance. But it's now caused some really serious effects that are not even obvious right now. Let's also remember you're not in dire financial straits. You have tons of money. $238,000 a year. Is that a lot or a little? What do you think?

I'm proud of what I have achieved personally in terms of my own career success. But I Never feel good about money.

Yeah.

Because I always think they're like, we need more buffer.

Right. Oh, if you make an extra 50k, maybe you'll feel good then.

I won't. No. No, I absolutely won't.

Who taught you that?

You did.

That's so crazy, though. But what if you make 100k? Would you feel better then? No.

No, because I'll never feel like it's enough. I'll continue to worry. Like, if I was richer, I'd be like, the folks you have on the podcast who have, like, 5 million in their 30s, and I would still be crazy.

I could literally calculate the exact month that you're going to have that much. And you're right. You will come back on the show and feel exactly that way. It's a guarantee. Unless we make some changes.

Yes.

What do you think those changes and broad strokes have to be, Stacy?

I need to share responsibilities and actually share them and hand them off, not continue to partially own them. I think the other thing, I don't know if Jesse was feeling this way, but why I was quiet just now is like, I always thought encouraging Jesse to start his own business was such a good. Like, I thought I did a good thing, and I'm feeling like I didn't do a good thing because I. I probably, like, Coach coached him in the direction to go instead of, like, really just letting him make his own decisions, and then now he doesn't dream big enough.

How would you describe the way you feel right now?

Like, mad at myself.

Mad. Why mad?

Because I don't think I realize what I created.

What did you create?

An environment where, you know, Jesse doesn't see the big vision of what he's capable of doing, whether that's finances. And I'm. I'm sorry, Jesse. Love you so much. But, like, it's so clear that you're so anxious on this conversation the deeper we get in because, like, you're using, like, buzzwords to try and, like, talk effectively instead of just being like your. Yourself. And I feel like I. I created that.

How do you receive that, Jesse?

A little confused, a little frustrated. The way I've created, structured my business, it likely will never grow beyond a certain point.

How much?

I. I don't know exactly what the dollar amount is, but probably not much more than 4 to 6k a month. I know that that causes Stacy a lot of anxiety and pain.

Do you want to talk to her about it?

I feel conflicted, Stacy, because you pushed me. I. I feel rightly so into pursuing this, this business. And I am happy that you did and I am happy with the company that I've created for myself. But I, it also pains me to know that I will be unable to financially contribute as much as you ideally would like. As much as I ideally would like. Like in, in a perfect world. So it's, it's, it's difficult.

Do you have a question for her? Ask the question that you're afraid to ask.

When I lost my job and you said, jesse, start your business, do something that you love. You have a number of hobbies, make money doing one of them, and I pursued it and I, I felt I was upfront about how it would not be a great moneymaker. But I need to know if you.

You understand that the thing I'm going to push back on you is I think you're self inducing that limitation before you start. You're saying it's never going to be bigger. You create your own destiny. And I didn't ask for a specific number and you don't have to make a certain amount. But what really pains me in this conversation is I, I'm worried I created an environment where you, you're not even. It's not about trying. It's that like you're, I don't know if like you really believe that having one location of your rehearsal studios or two locations is enough or you could even dream bigger. I feel like you're hemming yourself in before you can even explore the possibilities. It's not really about what I expect because we can live off my income. That's why I pushed you to do that. If $4,000 is as much you're going to make in the next year, and then that might be the next 10 years, I'm fine with that.

Honestly, if I were in Jesse's shoes, I would be really confused right now. First Stacy told me that, yeah, it's okay I don't earn a lot of money. Then she told me I should start a business, which I did. Then she wants me to earn more money. But a few seconds later she says it's okay if I don't earn more money. Stacy's message is that she wants control of, but she also wants Jesse to participate. But when he tries, she says, not like that. This is all very confusing.

It's quite the weight off my chest to hear that out loud. It feels like it's, you know, it's always something looming over my head where I worry because, you know, Stacy is the kind of person that is always concerned about money and not having enough of it. And to your point, you know, it's like, well, you. We make X amount. You've structured it so that we are stable. But it seems like the narrative is always, we need to make more. We need to make more as a household. So it's good to hear you say out loud that it's okay if I fail essentially with. With income.

Was that your intention, Stacy? Is that what you meant to communicate?

No, I. I meant to say, well, I mean, yes, it's okay to fail, but what I meant to say is. Don't make decisions based on what I said.

Say.

I want to hear your own thought. I think in this conversation I've heard you parrot back some of the things I've said or Ramit says. What I'm missing is like your perspective, like, what do you want? Because when I hear you say, like, I'm doing this business, I'm making a small amount of money, but I'm taking care of the home. I fed you that narrative. I don't know if that's what you really want, and I don't know if you're being honest that that's what you want. Is that honestly what you want?

That is honestly what I want. I enjoy cooking. I enjoy being at home because Cissy works from home, so I get to see her a lot more than I used to when we were both working out in the world.

What else?

It's. I guess it'd be like the fruits of your labor. Again, I'm sorry for using buzzwords, but it's something that I can see that, that I'm. There's. There's an A to a B.

Now. That's an honest answer. I like that. That's a perfectly respectable answer.

It's.

You're right. I don't get that in my business either. There's always projects that are ongoing, blah, blah, blah. It's rare that it's just done and clean and perfect. Stacy, do you think that you're having unrealistic expectations for Jesse to suddenly become a long term career planner?

Yes.

How long have you been trying to get him to think like you?

Forever. Forever. Probably since we met.

You think he picks up on that?

Yes.

Because there's this narrative that he believes you need to have more money. Is that true?

Yeah. Yeah. Jesse thinks I'm like, money obsessed. And like, as. As if I'm. We've had this discussion before. He's like, you're obsessed with money to the point of like, it's like greed. But what we've talked about in the past. And I guess. I guess Jesse is, like, still not clear, maybe is, like, what I'm. Why I obsess about money is for safety. I'm obsessed about it from a sense of, like, security. And I want to just make sure there's enough not just to survive, but to be able to, like, retire comfortably.

And is obsessing going to help you achieve that?

It has so far.

So you should keep doing it.

No.

Why not? It's gotten you here. Got a million bucks in the bank. Why not just keep doing it, obsess and make 3 million?

Because clearly it's caused the sacrifice. I'm like, what I'm losing is in our relationship. Like, I've created this dependent relationship that's not. It's not sustainable.

You are, in your own words, obsessed with money because it provides you safety, and you. What, you want to change that obsession or you want to keep going? I'm not asking a loaded question. I'm legitimately curious.

I do not want that. Continually optimizing won't change any thing.

You optimize a lot.

Yes.

Like.

Like, I'm always looking at, like, how much am I putting away in our investments, and I, like, want to increase how much we're putting away to retirement so that in, I think it's like, 10 years, we'll have enough that we'll need for retirement, and then I don't have to worry about putting so much away.

Oh. And I said you're gonna stop worrying.

Yeah.

Come on.

Why you. Why are you doing this to yourself? You listen to every episode of the podcast. You've read my book, right?

Yes.

Do you think I use the word obsessed with money management?

No.

It's boring. It should be, like, what would you cook? Anything simple, like eggs or something at home.

Yeah.

Are you obsessed with eggs?

No.

You throw the egg on the thing, put a little butter. It's done. Right. It's a utility. At a certain level of money mastery, you don't even have to be a high earner, but at a certain level of knowledge and mastery over your psychology.

Yeah.

Money management itself is really boring, and it should be. The problem is that there's actually a real cost to doing that with your money.

Yeah.

What might you get out of changing your approach to money?

I feel like I have everything to gain.

Then why haven't you done it already?

Because I've worn, you know, like, the finances have been like, my cross to bear. Willingly cross to bear.

Like, it's as if it's a negative thing.

Yeah. Or Like. Like, it's. Like, it's. It's my responsibility.

Tracking a budget for what? Tweaking a spreadsheet for what? And also having all these negative conversations where you're always lecturing him, yeah, you really should make more money, blah, blah, blah. And then you don't even care if he makes more money. It's like, what's the point?

Yeah.

Is there a way for you to have fun with money?

We are going on a trip to Italy in about three months. Two. Two months?

What the. Hold on. That's awesome.

Okay.

Round of applause. All right. I'm getting the sense that I might have been wrong, but let's play it out. That is awesome. How long are you going for?

Three weeks.

Just. I have three weeks. Yes.

Damn. All right, cool. Who came up with the idea?

This was a big plan. It's been planned for, like, two years.

Wow.

Okay.

And you both are excited. Have you ever been to Italy before? No.

No.

So cool. All right. What are you two in particular excited about?

Generally, just travel, as Stacy mentioned earlier. Conversation. She. Or when she was growing up, she went on a vacation. I did not go on my first vacation until I was 22.

Where'd you go?

Azores. It's where I'm. My family's from.

Portugal.

Portugal.

So you're going on this trip, and has this gotten kind of the juices flowing in terms of, like, ooh, where else might we go?

Exactly that.

Well, okay, so Italy is the big one for this year. Next year is renovating our backyard and redoing our fencing at the house. So started thinking about that.

Wow, that's so cool.

And then the year after that is Japan.

Yeah.

Is there some reason that you take one trip per year?

We don't even do that.

Yeah. Is there a reason for that? I mean, it's not like you're making, like, $20,000. You make $240,000 a year.

Because when I look at our numbers, I think we're behind on saving for retirement. So I. I want to focus more money towards retirement than.

Yeah.

Travel.

Yeah. Good. The. The one thing that neither of you are really excited about, you want to focus on that. The thing that. And the thing that lights you two up. Let's. Let's wait another 10 years to do that. Y' all realize how ridiculous that sounds? Look at the rest of this CSP. We didn't even finish it. Your fixed costs are 39% of your take home. That's one of the lowest numbers I've seen on this show. 39% that's good. Do you realize that?

Yes.

Maybe too good. It's actually. It can be so good that it's bad. I'm not saying that's the case, but I'm just saying, wow, you got a lot of extra money to play around with every month. Your investment's 21% of take home. That is extremely good. At 21%, it tells me either you're, like, way too frugal or you have a pretty high income. In your case, I think you have a very good income. That's fantastic. Above 25%, I would start to get a little wary. I would say, why aren't they spending some money on life?

I want to double that number.

I'm not surprised. All right. And you can. And if you double it, you will certainly achieve your goals faster and you will be miserable, and you will cost immeasurable, unmeasurable cost to your relationship. Number one, you're both depriving yourselves of enjoying these experiences. Taking one trip every three year makes no sense. And second, actually not giving ownership. This is an amazing opportunity to give ownership to Jesse. Say, Jesse, I notice you love traveling. I love traveling. I would love it if you would be the person in charge of travel, helping us schedule our travel. Can we have a conversation about that? He's nodding. He's going, yeah. He's getting excited. I see that smile. Okay. It's a lot of layers here. I find it very interesting. What do you think?

So when we started this conversation, you said, what did you want to get out today? I'm like, I'm hoping you see something we can't see. And you did. You've seen that. We've. I've optimized the system. I'm getting exactly what I put in and reaping it. And I've created that for a really long time. What I'm recognizing is if I look at this as a scale, maybe I have this 100% optimized. What I'd actually like is maybe 80. And there's certain areas where I would value Jesse's involvement, but it doesn't have to be in the details, and we can balance it out more effectively.

Okay, that's pretty. That's pretty perceptive. I agree. Jesse, what do you think so far?

Very much the same thing. I felt Stacy had a narrative she wanted coming in, which was, I think she wanted to have a conversation on how to better optimize our savings for our retirement and how to enjoy the. The latter half of our life. Not. Not just like 65 plus, but like 4 plus.

Really? Is that true, Stacy?

What the is there were two sides to my.

What are the sides?

Well, I knew, like, there were definitely hang ups we had about money in our, like, our dynamic that needed a lens. And then the other thing that this, this is the problem that I'm mostly worried about when we talk about finances. I'm worried that we will have a. Not have enough for retirement and that we're, like, enjoying life enough.

Yeah. Okay, you're worried about retirement and you're not worried about the fact that one partner is totally disempowered and disengaged from money. You already know the answer to your question about retirement. I'll answer it anyway. But it's not a retirement issue. That's not going to be your challenge in your relationship. Your challenge is staring you right in front of the face. What is it.

That it's one sided.

Yep. And Jesse, what else?

Codependent.

That's a good way to put it. But when you say codependent, you mean what?

Stacy has created a system where I don't have to be involved.

Yes.

But I very much should be. Or. And she very much would like me to be.

Yes, yes, that's accurate. So what would happen if you just flip the switch tomorrow and both of you reverse rules? Stacy, you're keeping the house clean. Look at. She's already laughing. And you better keep that kitchen, you know, spotless according to Jesse's standards. And Jesse, you're managing all finances, you're planning, retiring, making all decisions. What would happen?

I mean, I would, I would like to think. Sorry, you want me to speak more confidently? I apologize. I would likely look at the budget as written and try to stick to it as closely as possible. I think I can handle that.

I think he would learn and figure it out.

Before I get to the follow ups from Stacy and Jesse, which are fascinating, I'd like to ask you to do two things which really help. The first, go to Apple Podcasts and leave a written review. That really helps us. And second, get on the podcast newsletter where I share new material every single Saturday. Go to iwt.com podcastnewsletter and you will find a lot of material that I never share publicly. All right, let's get to the follow ups. The first from Stacy. I got out of the conversation what I had hoped to see, something I myself was blind to. I walked away understanding that I had created a system for an inequitable partnership in our finances. And I've got work to do with Jesse to unpack and rebuild that relationship. I watched the first two episodes of the new show and I do not want to have the relationship Matt and Amani displayed. I was reinforcing an unbalanced power dynamic that I did not actually want. My biggest takeaway was that I have been swooping in to save the day when it comes to money. It's created an environment of intimidation instead of curiosity. The day after your call I started to change that. We started to take steps to give Jesse skin in the game when it comes to our finances. We readjusted our CSP yesterday evening. Instead of looking at our total income, we looked at Jesse's income and broke out the household spending under his responsibility and allocated investment savings per proportional to his income. He's going to pay for and own the budget for anything household related. He will also set up a recurring deposit for his investment account based on 20% of his income. We also rebooked our regular financial check ins. We rescheduled it to a date we could commit to. Jesse will be taking ownership of the agenda and on and on they go on to share more and more details. We looked at what we want to achieve in the next year and whether our savings targets would get us there. This left us with a much healthier 21% guilt free spending allocation in our CSP. Thank you for the coaching and guidance. Step by step, I know Jesse and I will create a more equitable financial partnership. Jesse wrote a follow up and said my feeling before going into the conversation was a fear that I was going to be blamed for not being involved with our finances and accused of being disinterested. I was surprised by your observations of our relationship dynamics over the past 18 years and how they fostered these feelings of anxiety, avoidance, avoidance and disinterest. I was even more surprised by your insistence that we needed to start spending more money on ourselves in the everything else category of the csp. The following night we sat down and discussed our budget and I'm now handling our day to day spending including groceries, pets, house supplies, etc. We have a long road ahead of us, but we will not be skipping our monthly meetings any longer. Fantastic work. To Jesse and Stacy, thank you for the courage in coming on this show. We all appreciate it. And for everyone who's listening and watching, go to iwt.com podcastnewsletter because I've got new material to share with you this Saturday and every Saturday afterwards.

Ra.