Episode 21: Getting Honest With Your Money — So You Have More Options
In this episode, Brent and Rob explore one of the biggest hidden barriers to your next great act: truly understanding your personal expenses. From the “one-off” costs that somehow show up every year to the money stories we carry from childhood, they unpack why avoidance makes finances feel more complicated than they need to be. This isn’t about budgeting or restriction — it’s about clarity. By revisiting the two numbers — what you spend and what you have — they explain how getting honest with your annual spending can simplify your financial life and create real optionality for what comes next.
Links, resources, books mentioned:
The Psychology of Money — Morgan Housel
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
The gap between what you think you spend and what you actually spend can be meaningful — and that gap shapes what you believe is possible.
“One-off” expenses rarely stay one-off — they’re part of the rhythm of life.
Avoidance is what makes personal finances feel heavy and complicated. Clarity simplifies the story.
This isn’t about budgeting. It’s about truth.
Simplifying your accounts — both expenses and assets — can give you a clearer, calmer view of your financial picture.
The money stories you carry quietly influence how you earn, save, and spend.
When you know your numbers, you stop guessing — and that’s where optionality begins.
Transcript:
Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.
Lena: When was the last time you actually looked at what you're spending each year? Not guessing, not estimating, actually looked. Today on Midlife Circus, Brent and Rob tackle one of the biggest barriers to your next great act, your money story. From one off expenses that show up every year to the assumptions we never question, they explore how clarity, not budgeting, creates optionality. This isn't about restriction.
It's about understanding your reality. Before we begin, remember to follow Midlife Circus on Apple podcasts or wherever you listen, and join us in the Midlife Circus community on Substack. Let's dive in to getting honest with your money so you have more options.
Brent: Rob, when you look back at your expenses from the last year, was there anything that genuinely surprised you?
Rob: A couple of things surprised me in the expenses, but I actually answer this question, I'm going to go back beyond just the one year. And I'm going to look over the last just couple of years when I look back at expenses. What I would say the biggest surprise, and it's going to sound really weird, is the consistency of one off expenses. Every year, you have one off expenses. Right?
So we had the transmission on our pickup truck went out, so we had to replace the transmission, in the pickup truck. And early on, was thinking, yeah. That that's not going to happen again. And so we won't have that expense going forward. But it gets replaced with a different expense every year or every couple of months.
There's these random one off expenses. So I'll give you a couple examples of some of those expenses that have happened in the last year. Transmission or truck went out, and so rather than buy a new truck, we got a new transmission installed in the truck. As you know, our bicycles got stolen on a road trip off the back of our van when we were parked in inside our friend's house, so that's we ended up replacing our bicycles. Not something you plan on doing every year, but, you know, that's a hand every, you know, five, ten years out that might be a replacement, but we had to do that.
Medical procedures, those things pop up. I know you just had a recent medical procedure that there was a pretty significant expense that came from that. The trees in our backyard died, and so we had to replace a number of trees outside of our house, and so we did that in the last year. We decided to replace a couple of really old pieces of furniture in our house that we didn't have to do that, but that was more of an aesthetic thing we wanted to. And then even in the last year, we upgraded the stairs into the attic space in our house.
We used to have the Christmas vacation staircase that kind of accordion out of the out of the ceiling, and I, I was always anxious I was going to fall off this thing. So we had a real staircase entered up into our attic space in the garage. So the consistency of these one off expenses, they just keep happening. You had your boiler go out recently. Right?
That's another one off expense to go and get fixed. And I early on when we did the math on retirement, we factored in some, you know, kind of a budget for those one off expenses, but it seems to be larger than what I had originally anticipated. Because they're more frequent than I thought they would be.
Brent: It's interesting how you describe that, is it is consistent. So I did the same exercise. I looked back at the last year and I was so surprised at some of the things, but then I looked at the previous year and the previous year. So house maintenance, car maintenance, one off medical expenses. Well, they're all pretty consistent from year to year.
Now the good thing is they're not growing. Right. You know? So my medical expenses are not getting more expenses at this point in time. So that's a good thing.
The house expenses, you think you got it all figured out. You fix one thing. So you mentioned my boiler. Hey, I fixed that. Well, guess what happened the year before?
Refrigerator. What happened the year before? Washing machine. So it just happens and it's just part of the running a house, part of being a human. You just have expenses that do come up.
So how this ties into this episode, Rob, is we're going to talk about the whole concept of getting honest with your money. And really this is a tie into one of our previous episodes. And I think it's probably the most talked about episode when I talked with friends and listeners is the two numbers. And we think about if somebody wants to go pursue their next great act, they've got to figure out the two numbers. And one is how much are you spending?
And the other is how much do you have? And one of the things that people have to get honest with themselves is how much are you really spending? Because it's a shocker. It is amazing when you start to put it out. So some of the things last year that I looked at that I was like, Oh, really?
Taxes? That was one thing that came up. I was like, I know I write that quarterly check, but I never really look at the combined amount. I'm like, dang, that's just part of living in America. Pay your taxes.
Don't have a problem with it. It's just it was a line item. The other one for me, kids in college. That one showed up, and I'm just used to writing the checks here and there, you know, and you're just paying for tuition and housing. And one of my kids moved from one college to another college, and so the other college a little more expensive.
And I saw the bottom line. First time I saw it was this morning from last year because I didn't pay attention to it. And I was like, wow. That's a big number, a little bit more than I thought. So I'm going through this, but the one I'm most proud about in every year I look at this one is vacation and travel.
When that number's up, it means there's probably some really good adventures that took place. So I'm proud of that number. But the other ones like the home maintenance, I'm not necessarily not proud of them, but I'm just not excited about them, but I know that they're a part of it. So it was an eye opening experience, but I will tell you, I only spent ten minutes and just looking because I do capture it using some money tracking apps. And it was interesting just to see the outcome.
And I was like, dang, Uncle Sam, you're taking a lot from me.
Rob: My grandfather was an IRS agent, Actually, he managed multiple IRS branches, and every year, he'd help me as a young kid prepare my income taxes. So it's kind of fun having the guy who would audit me actually help me prepare my in income taxes. And I just started as, you know, fifteen, fourteen, fifteen, sixteen years old complaining about having to pay income taxes. And my grandfather would say, well, you know, Rob, it means you made some money. So it's probably a good thing.
You should be proud of the fact that you get to pay your income taxes because you're making some money because alternative is likely worse.
Brent: Absolutely. Or that's how it works. And so I don't I don't get upset about paying uncle Sam. It's just part of if you made a little bit of money, you're going to give a little bit of money, and that goes to support our country. So there's going to be two key takeaways for the conversation today, and then we'll dive in.
The first is how do we get honest about getting clarity around our personal finances? We're going to talk about the lessons learned there, what we see, what we read about. And the second one is what happens when you avoid understanding your personal finances? Because there's a big portion of the population that actually avoid understanding where they're spending money for one reason or another. So that's going to be the main two themes for today's conversation.
But Rob, as we dive into this, I mentioned it briefly, the really popular episode that we had was understanding the two numbers before you jump into your next great act. Why don't you just take us a little bit through the journey, but more importantly, as you're doing this, describe how you got there because of your background and how many people you've interacted with to actually better understand the simplicity behind the two numbers.
Rob: Financial planning and preparation for any big adventure or big endeavor, I should say, really is is complex, Brent. There's a lot of moving parts from a financial standpoint. In fact, we can probably have an episode just right name off all the different moving parts when it comes to whether or not somebody can or can't retire or move on to the next great thing. And in working with both advisors and clients historically, one of the biggest roles I see advisors place playing is trying to simplify things. The industry is really complex with a lot of jargon and really great financial advisors will simplify things for clients.
And one of the simplest things as a client to think about are really just two numbers, and you mentioned them earlier, is what you spend on an annual basis. That's something you actually have some level of control over. You have some discretion on some of those expenses. So what you spend on an annual basis is guaranteed expenses or fixed type of expenses or regular living expenses. So it'd be like food and groceries.
It would be medical cost. It would be your shelter. So your home, your house payment, your rent payment, those types of things. And they're really nondiscretionary expenses. Then you have the discretionary expenses.
So going out to eat, clothing, travel, all of those things are discretionary. And really understanding what that is on an annual basis, which we're going to spend time today talking about. The other number is is how much you have you need to have set aside to create that income for yourself. So if you're going to spend a certain amount on an annual basis during retirement, what do you need to have set aside to create that level of spend? And there's a lot of numbers and a lot of ways you can calculate that, but those are really the two numbers that as a client you should focus on is what's the nest egg you need to have set aside, and then how much are you going to be able to spend, and how much do you need to spend on an annual basis?
Brent: So you've got an expense side and you've got a savings side. Exactly. And today we're going to focus in on the expense side and really understanding how do we get honest with our expenses. So the first question that I have for you is, going back to the opening question I had for you, as you look back at last year, did there anything outside of the surprises? Did you make any adjustments or any changes as you evaluated?
Because I know you and Tara pay special attention to this because especially because you left your job a couple of years ago and you want to make sure that you're not, you know, running out your savings quicker than you anticipated. So as you looked at your expenses, is there anything that you started to say, we need to make some adjustments?
Rob: A little bit. Yes. And this goes back, Brent, I would say now twenty seven years. I actually don't manage our budget. Tara actually manages all of that.
She does a really good job managing our budget and monitoring our spend rate. Since I left work, I'd kind of had numbers in my head. I mean, I look at the credit card statement from time to time, which we pay off every month. Right? I look at those things.
I say, I I kind of had an idea what we were spending on an annual basis. And at the 2025, we were in a discussion. I'm going to call it a discussion. It wasn't an argument. It was just a nice discussion around our spend rate, and she told me what the number was.
I said that that's not right. That can't be right. No. No. No.
That they're not even close. I here's what I've been looking at the credit card statements. Almost everything we have goes there, and this is what I think it is. So we have plenty of wiggle room. We could go do this or we could buy that.
Right? It shouldn't be a problem. And she said, why don't you go through the math? And so I did. I actually went through the statements month by month on the statements.
I went through what we had is automatic withdrawal from our savings account, so not just things that were going on to the credit card, added everything up, and it was 25% higher than I thought it was mentally. And that was a surprise. I thought I was pretty close. I've been working numbers my entire career. Like, I could eyeball it.
I could I could guess pretty close, and I was 25% low, which is pretty significant in the grand scheme of things. Now we're still okay financially, but it's tighter than I anticipated. I thought that we had quite a bit more wiggle room in terms of the discretionary spending, and we don't. And so because it's a little bit tighter, we pulled back a little bit on some things like going out to eat as often. Some of the major purchases, we've decided to push off a little bit and not do them right away and try and just get some, get some more money into our cash reserves.
But that was probably the biggest shock to me is the gap that existed between what mentally I was thinking we were spending and what our actual spend rate was.
Brent: What you just identified there is a significant challenge that we all face. So I'm a numbers person similar to you. And what I think about is it's easy to understand one month, one week, one day at a time. But when you start to accumulate those over a period of time, it's really hard to say January, March, April, like all these different months, what happened in February. And you may have forgotten that, yeah, we actually did do that transmission.
You may have thought you did it in January. Maybe it was last year's expense. No, it actually wasn't. It was this year's expense. So when you start putting all those things together, it's not a surprise to me.
And I had the same experience. And I always have a specific number to say, this is usually the monthly spend. Now I always know at the beginning of the year, it's a little bit more expensive than later in the year just because you've got taxes associated with our houses. I think that's usually due in the first quarter. And there's some things that show up in the first part of the year.
So I know it's expensive and I always felt like, well, it kind of evens out over time. It didn't last year because other expenses came in. As I mentioned, like the college expenses, how they come in and when we're spending money on college. And it's just really fascinating when you look at the whole collective and how you're monitoring it. And for me, the challenge that I have is behaviorally, so then what am I going to do about it?
And how do you address that? Like what is that when you were off by 25%, you said you're going to pull back deferred expenses, but then there's that challenge that we now have that you and I have the exact same experience, which is we used to have these consistent paychecks. Now we've got other income that we're generating through some of the work that we're doing. And we've talked about that on previous episodes. So you and I do some coaching work.
We do some consulting work, but it's not the same income as we used to have. So how do you think about that? Because psychologically, that's a really challenging piece of this process on expenses because you used to be able to make up for it.
Rob: Right.
Brent: Because you knew there was a routine paycheck or bonus period kind of covered. For me, it was always the bonus time of the year that kind of picked up for some of the extra expenses. Like, ah, now I'm even again.
Rob: Yeah. And my bonus typically paid right around this time of year too, is when we always got the bonus for, know, based upon previous year's results, right?
Brent: March is happy month. That's right. Every year, March is usually March or April was always from the companies that I worked at that were larger companies. It was like happy time. Everybody's nervous in January and February, and everybody's trying to be good kids in the office.
Because they're like, this is when I'm being evaluated. Saying it's, you know, we're evaluating last year's performance, but everybody's all happy and, you know, doing really good stuff in January and February because I know March and April is when the big paycheck comes.
Rob: Kind of, I would say, Brent, a little bit of a shame on me. And this goes back, as I said, you know, twenty five, twenty seven years that I have not paid attention to the day to day budgeting. And that's a decision that we made in our household pretty quickly after we got married, Tara would actually manage the day to day budgeting. And the rationale for that, I think it's common in most households, is one of the spouses will actually manage budgeting, one might manage investments and they might just split the work there or one might do everything and one doesn't actually get involved at all. Given the role I was in both in financial services looking at that stuff every day, think that I would naturally gravitate towards managing all of that.
And early on in my career, it actually stressed me out. It I had variable income, so my income would fluctuate. Then I start looking at expenses, then I looked at our budget. I was looking at what was coming, and I it my anxiety kept growing, and I kept getting more and more and more stressed. And so we decided that Tara would actually manage our budget on a week in and week out basis, so I didn't have to know what we had in our savings account.
I didn't have to know what expenses were coming up, and Tara would just let me know, can we spend the money or not? And can we go do something or not? And that was really healthy for us at the time. And so I haven't paid attention to our spend rate, and that was early on in my career as my income kept growing. We kept having more flexibility in our spend rate in the last number of years, and I think this is going to be the most the case for most of our listeners.
In the most recent years before they actually decide to leave work, they're probably in their highest income years and likely not having to think about what the expenses are on a weekly, monthly, or annual basis. They're able to spend. They're saving money. They have their retirement plans growing, and they're not actually having to watch what their spend rate is. And so it can become quite shocking to not have that income stream coming in on a on a regular basis where it's every other week and then the bonus check that makes things whole and builds that account back up throughout the entire year.
Right now, I get to see my cash account start to be depleted, and that's part of the plan. My cash accounts will deplete as part of my retirement income and distribution strategy, which will likely be one of our future episodes as some of the distribution the ways of thinking about distribution strategies. We're not going to get in the weeds on that, but thinking about that. But my cash will get depleted, which I'll keep replacing over time as well. But watching that account balance go down, knowing there isn't any other money coming back in.
And one of the things that I've decided is not to include some of the consulting income into that equation as well because that would just muddy the waters a little bit. I keep my consulting income completely separate from the retirement assets and things like that because I use that to just run and manage the businesses that I'm involved with.
Brent: How you're describing this is one of the things that I've learned because I've had to help in the last couple of years, a family member with their finances. And this family member is in their kind of later stages of life and their partner used to do it for fifty years, let's say for the relationship. And they decided to make a change. And so the other family member is going to take it. They had no idea, like no idea.
They never looked at things because everything was always fine. It was a thumbs up. Like, how are doing? We're doing great. Thanks.
That's the conversation. So one of the first things that I did is let's give you visibility into it. So we use a cup There's a couple different apps out there. There's actually a lot of apps that help track finances. But what was interesting going through this, as I said, the first thing we need to do is get clarity on where you're spending money.
And what was interesting is there was secret accounts. I this credit card that I use just for my stuff. I have this little savings account over here that's just for me and both people in the relationship are doing. This is a marriage that's been around for like fifty years. And it wasn't anything trying to hide from one another.
It was just something that they always did is like, oh, this is my little, my cash kitty. And they just had a little separate account. I said, all right, let's get the whole picture in here and let's roll it all in. And the beautiful thing about apps today for tracking finances is they can connect the dots for everything. And what was interesting is one of the pitfalls that we have with our generation that I find with people tracking their finances is when we were all at the college years, let's say, or in our early twenties, that's when credit cards were given away like candy.
And I remember on, I was in college on campus and all those students are like, Here, dollars 500, just sign up and you'll get a $500 credit limit. So you accumulate all this debt because you'd have not just one, because you're going to burn through 500 quick, you might have two or three. So then we carry that into our adult life and we might have a credit card for our favorite retail furniture store. We might have a credit card for a place that we shop for clothes. We might have a credit card for an electronic store.
You get all of those, and yes, they're going to give you the perks and the bonus, and that's your justification. It's like, but Brent, the rewards are great. Yeah. They are.
Rob: 0% interest for six months. It's like free. Can get in, my investments will grow. I can let them sit in the market or I can let it sit in my savings account. It's free to do it this way.
Brent: Yeah, it's the story that we tell ourselves. And it's really the marketing story that they sold you on it. 2% cash back, get special perks. So you have all these things and those are great. Let's not lose sight of the importance of those things as well, but I call it tentacles.
There's all these tentacles out there that is you're spending in all these different places and rarely are you bringing it all under one roof. So that's the first thing that I always do with people when they ask about personal finances and I'm not a personal finance professional. I've just done a lot of this for myself and my family for thirty plus years. And so I'm always the one who leverages technology, trying to figure out what is the latest and greatest app that's going to be the most efficient for me. And I make sure that we put it all in there, no hidden stories.
And I don't get overly critical on trying to be so precise with every penny of like, where did we spend this? What was that $6 transaction? Sometimes I have a miscellaneous bucket. I just don't let that miscellaneous bucket grow. I just want to make sure we're capturing everything.
But what's fascinating when I did this exercise for myself as an example, and this was several years ago, is I was shocked on how many credit cards that we had. And some of them were dormant, that's fine. But we would use them periodically because we get those special points. They reach out with that special email. We're like, Oh, we got to spend it now.
We got to do it. And so that becomes challenging. So it's consolidating everything has been a helpful part of the process. And then spending a little bit of time on categorizing everything and understanding where's your buckets that you spend. You talked about it earlier, shelter.
So what's your house expenses? What are your car expenses? What are your clothing expenses? And the benefit of these apps now is they do a lot of that work for you. And then you go into this maintenance mode.
And for me, I did this this morning just in preparation for this. And I looked at last month's expenses, just the reconciliation. In the app, it took me ten minutes, ten minutes per month. So, you know, it's going to take me a couple hours per year to truly understand my financial expenditure story. Super powerful, but it is hard to convince myself the importance of doing this, but I really have owned it, especially in the last couple of years.
I don't have the normal paycheck coming in on a regular basis. I just got to understand the outflows. Let's make sure I know what's going on. How do you look at the story behind it? Because you've always taught me different ways of how you've seen people mismanage their money.
How do you look at this so it's not a cumbersome exercise that it's a version of the truth and it's something that you guys can rely on?
Rob: I'm going to go back real quick, Brendan. As you said that we, you know, in college, we had all those credit card opportunities. You had the tables in the quad where you had your buddies are actually working there. You it was friends that were trying to get you to sign up for credit cards, and you had Visa, Mastercard, Discover, and American Express all had a table for you to go sign up for. But that's not where we learned to be consumers.
We learned a lot sooner than that about being consumers and having things. Right? I think about when Toys R Us opened up its doors in Oregon, the first Toys R Us. I I'm sure I waited in line. I'm pretty confident we waited in line to go inside and look at everything that was there.
Right? I mean, you remember going into Toys R Us for the first time? I want this. I want that. I want this.
Right? Cartoons growing up that we had Saturday cartoons. It wasn't on demand where you can just fast forward through commercials. We got to sit through the commercials of buying more stuff and having this, you know, the sugary cereal or whatever it was. So we were all conditioned to actually be consumers from a very young age, and that continues today with even the ability to order things and have it delivered to your house within a couple hours of ordering it.
Right? Well, I don't have to wait. There's no delayed gratification on anything really anymore to be able to have access to it. And so that's I think that's part of the problem that we all face, especially in our generation. It's not the immediacy of having stuff is that we were very early on, you know, conditioned to consume.
And we consume food, we consume media, we consume news, and we consume stuff. And just being mindful of the stuff that you are consuming. Right? How much stuff are you bringing into your house and really looking for as you make that next jump or that next transition is, do you have a chance to simplify? And that's likely the biggest thing out of this episode I would suggest for anybody to think about is it is just simplifying the day to day.
And so whether it be all the stuff in your house is going through and doing a big purge, I knew it's is it Marie Kondo that's asked, does this bring you joy and simplifying the things? You know, I've read books that talk about paradox of choice and the amount of clothes that you have and turning around. I did this this year, Bert. I turned around all the hangers in my closet to see if I don't wear something this year, I'm going to purge it at the end of the year. Changing some of the lifestyle habits around consumption will help with this, but then simplifying from a financial standpoint so it's easier to look at things.
And you mentioned there's apps that are available to help people, you know, consolidate information, but that adds a layer of complexity because you got to take the step to put all of that information in. And I and I think a lot of people get stuck in the world of I don't want to know the information, so I'm going to leave it complex. And they may not say that directly. Is it it's complex, so it's hard to figure out. Well, you could take the time to reduce some of complexity.
Right? So you have five credit cards consolidate to one, but they say, well, this one has a lower interest rate, so I'll leave some money over here, or I like to spend it on this card. It again, it it perpetuates the consumerism in all of us, and it keeps things being complex. So it's hard to understand and then make changes or tweaks and adjustments along the way. And so we've tried to simplify things as much as possible in our household.
So having, you know, a singular credit card that we use for almost every expense. Now I'll tell you that becomes a real hassle when your credit card gets compromised and you have to go through and change all the numbers, but you only have to do it for one card. Right? So, yes, it's one credit card that we have to change every account on. I don't have five cards floating out there that all make it compromised at some point.
And so it does simplify when things do go wrong. We don't get all the perks, so we might miss out on some of the travel perks or some of the 0% interest. I'm okay with that because it's simpler. I actually don't have to worry about complexity. It's easier to manage.
It's easier to understand. It's easier to look up and figure out what things might I want to adjust moving forward. I'd say the biggest thing is as we all go into this next phase is looking for opportunities and ways to simplify finances as much as possible.
Brent: And if we go back to the whole premise behind this episode is we want to understand the real story, but the whole goal here is to give you optionality on your next great act. And we find that this is a barrier that people have is their personal finance. And I think one of the challenges that I had definitely earlier on in, let's say my career earlier on in just my adulthood was I never liked to budget. Because I'm like, I'm earning good money and I want to just go spend it. I want to enjoy life.
This is not a budgeting exercise per se. This is a truth exercise and just getting clarity. And it's surprising. There's those commercials that have how much, like there's apps out there that help you identify how many subscriptions you have. And it's amazing.
So I try to do at least once or twice a year. I just go on my phone, look at my subscriptions, and I'm like, I signed up for that? Like, I use that once and I'm paying $10 a month for it. It all adds up. And one of the interesting things that I've got to observe in my professional career, as many of you know, I spent the last several years of my professional career in the investment space and I often interacted with very wealthy, wealthy individuals.
And what I found with wealthy individuals is a lot of them are incredibly frugal. They don't like to spend $25 on that subscription. It's because it's in their DNA. They're great savers. They're great accumulators.
They believe in compounding their money. It's interesting because you go out and you'll watch I've watched people get into their car and be like, that car is 15 years old and it's falling apart. And you have enough money to buy 5,000 of those cars, and you won't even notice in your bottom line. And so it's a interesting behavior, but what we're trying to say is like, how can you start to simplify this process and challenge your assumptions? The assumptions of, well, I need to have this card because I get these perks or I need to have this extra card just in case one of them doesn't work and all those things.
Okay, that's all right. Maybe you need two cards. One of the things that I've done to help myself navigate that type of the process is, and I think it's a good best practice for anybody is have all of your credit on freeze, you know, with the major credit agencies. So you actually have to go and unfreeze your credit if you want to get a new credit card or you want to get a loan. It's just a simple step.
It's easy to do. It's easy to actually unfreeze it, but it's a step that challenged me like, do I really need to do this? Do I really need that extra credit card? Because I just know it's just one more thing to manage. So we've talked about this simplifying aspect, Rob, and we believe in that wholeheartedly.
And there's a lot of great ways to do that. And you've described even one layer is being a consumer and the consumption. And we grew up in this consumption. I mean, we grew up with catalogs and we grew up with commercials. And now, I mean, this generation today is growing up with social media where you're getting thrown ads your way and it is so easy to buy.
But we're just trying to say is like, okay, how do you consolidate those buying behaviors so you have a clear picture? But I want to step back a little bit and go back to one of the conversations that we had in the past. And I know it was an emotional conversation was when you were talking about some of the beliefs that you had growing up, maybe you can talk a little bit about how you came about and just understanding money through your upbringing and then maybe how it changed your behaviors as you became adult when you had your own money.
Rob: So as I've shared, Brent, that there were times growing up that money was tight, really tight, I was the oldest of four kids. And there were times that my parents just didn't have resources. We had a ton of experiences as kids growing up. My parents gave us great experiences, but I did not have the financial resources that a lot of my friends did. And that has shaped a lot of my financial decisions.
It's just around scarcity around money, but it hasn't stopped me from spending money. That's the other weird thing too is I I'm probably more of the spender in our household even though we had scarcity because we I do have resources, and so I do want to splurge, and then I justify the fact that I have the money so I can splurge right now. I can spend this and I worked hard to generate this income so I could spend this money. So a lot of your upbringing from your childhood impacts how you view money today for a lot of people.
Brent: The story that I have is I grew up in an interesting household. Mean my mom, she had a very blue collar upbringing. Things were tight. Her mother, my grandmother is a cook at the local high school. My grandfather or my mother's father, he worked in a machine shop.
I don't know if they got past eighth grade education. And so things were tight, but it was just how they grew up. And then my father, he grew up, we say, on the other side of the tracks where they had money. It wasn't crazy amount of money, but it was different than my mom's experience. So growing up, I had this conflict always in my house.
My mom was the ultimate saver. She was the one that would always save every penny. My father on the other hand was the ultimate spender. Whenever there's money coming in, let's go buy something new because he was a professional consumer. He just wanted to always buy things and it was the next great thing.
It became as I became older, it was bigger things. Let's get a different house. Let's get another car. My mom would always be like, but why? We already have all the things we need.
So that was this push and pull that I had. But something happened to me or to our family when I was I think I was in maybe the first year or maybe my last year of high school, first year of college, where my parents were forced to sell their house. My dad made a few investments that didn't go well. His business was doing okay, but it was tough decision. Now they didn't run out of money, but they knew that they needed to make some changes.
And they had a really nice house. It was the dream house. They built it. It was beautiful, but they needed to sell it. So it caused this challenge in the house because my mom was now living in her dream house and her dream was taken away from her.
My father on the other hand was like, well, I'll just earn it and we'll build another house. So they navigated that one and they actually didn't take them long to recover. But what happened to me because I was in such an impressionable age is I told myself in my late teens, I never want to put my family through that. And I witnessed it, I got to observe it, and I was like, I do not want to put my wife through that, my kids through that. So then I had this baggage for the next thirty years, and I literally did unpack that baggage until last year.
And my brother was so kind to have this really good conversation with me because I was always afraid of running out of money. And so my brother, he's like, Brent, why are you holding onto that story? He's like, first off, you're not mom and dad. Second off, you learn from mom and dad. Third is, you've been really smart with your money for thirty years.
So why are you holding on to their story thinking it's going to be your story? And it was an interesting awareness for me. And I I can't thank my brother enough because he set me free. He set me free from the story that I'd been holding onto that wasn't even my story. I was always afraid of losing our house.
I was always afraid of having to make some really significant lifestyle adjustments. And so I was very protective of that. What it did for me, Rob, and it created a different challenge. It created, and I'll flat out say it, workaholism. Because I was so fixated on working and earning an income because I never wanted to run out of money.
Now, how does this tie back into the bigger arc of this story that we have is I wouldn't look necessarily at my expenses. I wouldn't look necessarily at my income. I just worked really, really hard, but I never understood my story. And I literally didn't understand my story until a few years ago when I started to look at the big picture. I'm like, why am I still holding onto something from thirty plus years ago?
That was a story that I held. Now you had a story from thirty plus years ago as well. Everybody has their own story. The challenge that I have is, is that story holding you back? Is that story, that narrative causing you not to manage your money well?
Is it causing you to over manage your money? Being overly critical about your expenses. There's yings and yangs here. There's different things we got to look at it, but I learned a lot about myself and understanding the baggage that I've been carrying. And I cannot I say I'll say it again.
Thank you to my brother because he helped me through that because he's like, that is not your story, Brent. Why are you trying to own their story? It's that was their mistakes or whatever they did. You've write you're writing a better version of it. So I'm happy that I did that, but it was a part of the bigger picture, understanding the expenses.
It all kind of came together for me.
Rob: It's interesting as you as you shared your story, Brent, I was thinking, you know, with that background and your and my background having some similarity there, we also ended up pursuing careers that, you know, entrepreneurial, that had variable income streams and had great upside opportunity, but they also had pretty significant downside opportunity as well. And so that fear, we didn't remove the fear. It was always it was always there for us. We could have easily taken a job that had a fixed salary. I know what my income is.
That seemed like the safety net. That never seemed like a safety net to me as having a guaranteed income stream. I want a little bit more control over my income, which now is gone because I'm not generating any income. I'm not working significantly to generate income. So there is that fear that kind of does can and can creep back in, that, that we had from our from our childhood.
Brent: I remember the conversation I had with my dad. So coming out of college, I went and worked for General Electric and I was in GE Capital or division of General Electric and it was a great job. I was there for four years and then I had this amazing opportunity to go work for PricewaterhouseCoopers in their management consulting division. I decided to pursue that. I was there for a few years and my dad loved it because he never did that.
He was always the entrepreneur growing up. The running story is my dad, apparently he went to like five different colleges and never graduated, but he was a heck of an entrepreneur. I mean, he was so gritty and he was really successful. And it was just interesting. He just leveraged his strengths and he just knew he could go start any business and go be successful in it.
But I remember when I decided to leave management consulting and go launch my own consulting company, my dad said, Why? I said, Dad, I just think this is a great opportunity. He goes, I just always hoped that you would just stay working for a big company that would give you a consistent income because I never have had that. And I just thought that you would just love that. And I'm like, no, I think there's other opportunities here.
And he goes, you're going to be a great entrepreneur. And so then he flipped the script really quickly, but I just could see the letdown because he never had a consistent income for his entire professional career. Now he was consistent enough to keep the lights on and do really well. And so he was just like, Why would you give that up? I'm like, But dad, I'm doing what you did.
He goes, But I don't want you to do that. But then he was super supportive after that.
Rob: Well, the as you're talking about spending, and I think we'll talk about assets here in a second as well, but the spending piece, Brandon, it's really more art than it is science. I mean, you we talked about the science of understanding what the number is, but the art of spending and we're not telling people to stop spending. That's not the message that I'm trying to convey at all. So if you if you regularly get massages and there's an important part of your life of having a regular massage, I'm not telling you to stop doing that. It's just be conscious of what the expenses overall are for you, right?
That regular cup of coffee, that fancy cup of coffee that you regularly get, those might be two very important items for your health, for your mental health, for your physical health. It allows you to keep working or allows you to be in a stressful environment or from a massage standpoint, it allows me to keep doing physical activities by going and getting a regular massage. So we're not passing judgment on what your expenses are, but simplifying what your expenses are allows you to understand what they are. And then you can actually manage and control that art a little bit better.
Brent: When you describe that, Rob, what's really interesting through the whole process of understanding your expenses is getting into the psychology of money. And for those of you who have read this book or you haven't, I highly recommend it. So there's an author, his name is Morgan Housel. He's written a few books, Psychology of Money, The Art of Spending Money. They're just really good.
And they're not about being smarter with money. It's more about the psychology and the honesty with yourself around the process. As an example, when I read The Psychology of Money, I was so impressed by it because it helped me understand me a little bit more. And that was a good part of the learning journey for me. But this is a handful of years ago and I actually paid my kids $100 each to read that book and tell me what they learned from that book.
And they're like, dollars 100? I mean, that's a lot of money for a kid. Did they both do it? They did. They did.
And they did a great job. They didn't I didn't make it like this overly formal book report. I just said, I want to sit down and have a conversation with you because they're both in their teens at the time. And I said, I think this is an important part of your journey because you're starting to have your jobs, your part time jobs after school or in the summers and understanding money and the psychology of it is a really important part of thriving throughout your entire life. And if you understand why you make purchases when you make them, how you make them, how you track your expenses, I can't say that they're going to be great at the process one way or another, but I was just trying to set some foundation.
So I highly recommend the work that Morgan Hassell done. He's been on a ton of podcasts as well. And I just think he's so smart about teaching how we think about money in a way that's very, very relatable. It was a great book that when I read it for the first time, was like, or the original one, Psychology Money. I know he's done a ton of great work in this space.
He's just really good at his craft.
Rob: Beyond the psychology and the art, it's the simplification. That's the biggest pieces as we're going into this next stage of life is trying to look for ways to simplify a lot of areas of your life. And so as we talked about the two numbers today, but also in the prior episode, I would also say it's about simplifying the assets that you have set aside and the number of accounts that you have that'll eventually create income or that'll be what you spend during retirement and trying to simplify your life there. So if you have multiple four zero one k's from previous companies, looking for ways to consolidate those. Right?
It it's trying to find ways that all of the information you need is easily accessible in one place. That's the other thing to look for from a simplicity standpoint to get your arms completely around what the financial picture is.
Brent: I had a call recently from my financial advisor. He called me and said, would you mind if we consolidate a few of your accounts? And I said, yeah, I don't mind. And he goes, I think you'll appreciate it. It's much easier to just look at the bigger picture.
And why I had multiple accounts was exactly what you said. I had 401k’s that I moved over and rolled over and it had its own account. And then I had some sort of reason why I needed to open a new account at one point in time. Next thing you know, you got four or five different savings accounts or investing accounts, and they're all doing the same thing. They're part of the long term assets, but having multiple doesn't always give you the best picture because you might look at one and you're like, oh, the balance in that one's great.
And then you're like, oh, why is that so low? It actually doesn't matter. They're they need to be consolidated into one eventually anyways, or a couple if you've got different reasons for having more than one. So that was interesting you say that because I actually just experienced that phone call with a couple of weeks ago, because he's like, I'm going to help you here. I'd actually didn't prompt it.
He just said, I know you had a reason when you had these, but let's simplify this because then it helps him with his reporting back to me. So it's a better story in the long run. I'm glad you said that, Rob, because simplification needs to show up on the expense side and the asset side or what your savings are. It's the same drill. If you've got savings accounts and investment accounts all over the place, and you've got one at Schwab and another one at Merrill Lynch and another one at Vanguard, that's great.
That's probably a lot of legacy stuff, but it doesn't necessarily help you get the benefit of maybe getting lower fees. That's the same thing with credit cards. If you've got them consolidated, you might have a little bit more leverage to say, hey, this is my credit limit, and I want to have a better structure with you, better terms. So it's the same thing on the investing side. So I'm glad you bring that up.
So Rob, one of the things that you've talked to me about in the past is this whole theory of don't put all your eggs in one basket. And we're talking about consolidating accounts and we're talking both on the expense side and the asset or investment side. What's your strategy or what's your viewpoint on the whole eggs in one basket theory?
Rob: Yeah. It's interesting, Brandon, as you talked about the different accounts at different places. Right? And a lot of people think, well, I don't want to put all my eggs in one basket because if something goes wrong, I want them to be safer. And how I react to that, I think I mentioned this to you and you started laughing around it was I said, you're absolutely right.
Any smart chicken farmer would know you should never put all your eggs in one basket, but you might have all of your hens in one hen house. And when I say that, it it's not meant to be a joke, but by you're getting diversification already with your investments. Right? So within your IRA, you're diversifying a portfolio in that IRA, in that individual retirement account or in your Roth IRA. You're you have diversification between different types of investments, whether it be small cap, mid cap, large cap.
Right? But having all of those accounts at one financial institution allows for you to have that that diversification more effectively managed. When you have multiple accounts at different investment institutions, it's hard to actually understand even as an individual how much of your portfolio might be invested in a large cap stocks for per se, and that was the big trend in the in the late nineties and early two thousands was large cap. And most people's portfolios that I would see would be highly invested in just one asset class lacking very little diversification because they had multiple accounts at different places, they were judging the returns on each of those accounts differently versus actually a cohesive investment portfolio that encompasses all of those things. And putting it in one investment institution allows for a simplification of diversification.
So you're able to diversify your portfolio even more effectively because you're not having to manage it at different places.
Brent: And I would say with that is it's really, really important that you do your homework. Absolutely. Because some financial institutions are stronger than others. And we've unfortunately, we've heard stories of people. They go to somebody that's a crook, you know, the Bernie Madoff, and they've got all of their assets tied up with somebody that's not playing a straight game.
So you got to be careful there. And I think what you're saying, Rob, is we want to make sure you have clarity to your story. And when you have it in so many different places, it's hard to formulate the true story. So it's understanding where is your money? How is it being housed?
Is this a safe place? We're not going to make recommendations here because you got to do your own homework, but we've done it on our side and there's some very credible firms out there. And we just encourage you to think about it, but it's all about the story. If your expenses are scattered and you don't really have a good understanding of it, then you don't understand how you can improve it. You don't understand your What could you do?
What's your optionality in life? If you wanted to change jobs as an example, or maybe go on a sabbatical or do go on that big trip. If you don't have a clear picture, you may be delaying it just because you haven't spent a couple of hours to understand your story. So that's the goal of all of this is truly understanding your story so it can give you optionality on your next great act. So Rob, as we wrap up today, one of the things that I think about is the complexity that's associated with this and how people get frozen when you ask them about their expenses.
And we're not saying we're asking all of our friends, tell me your expenses, but people do not like this process. How do you coach people, advise people to really get a good grasp on how they're spending their money? What's the first few things that they can do to take the pain out of this process?
Rob: It's starting the process, Brent. It is looking at, you know, consolidation option, whether it be through an app that allows you to consolidate and look at what do all the numbers mean. Right? How do they add up? What is that expense rate look like?
What do all of your assets look like? And really do it from a place of seeking to understand, not from a place of judgment. Not that you're doing something wrong, but the bigger opportunity is if you if you have a chance to simplify and you actually start taking the chance to simplify, you might notice you have an opportunity in front of you that you can actually step away from work in the next six months, in the next year, or you can do the math easier to figure out it's two years out before you can, you know, pursue your next great act. That's the mindset I would suggest you want to go into this with. It's to look for opportunities and to look for the positive outcome of these actions.
It's not going to be to say, well, you know, just because I do this exercise, I'm going to have to, you know, stop buying that coffee or stop getting massages. That's not the intention of this at all, But it's the positive piece of is, oh, wait. I can still get the massages on a monthly basis and I can retire in two years? That is really cool. That that excites me to understand that now.
Now I'm really happy. I can move forward. I don't feel the guilt because likely that some of these people still feel guilt around doing these activities on a regular basis. They feel guilty around it because they don't understand how it's going to impact them long term and they might absolutely be okay.
Brent: And that's the process. You might actually be okay. And it's getting that clarity. And it's funny because it's like cleaning up the closet. Sometimes if you just delay it, delay it, and then when you do it, you feel good.
Cause you're like, oh, I finally just gave away some stuff. I don't need it. I don't need some of these things. Well, this is kind of the same process. If you start to clean up your expenses and the way that you manage your money, you might get rid of some expenses.
You're like, I just didn't even know I had that. I mean, we had this one situation when I didn't even know it. We were getting charged for two Netflix accounts. Didn't even know it. Like, I think one of us signed up for it, another signed up for it, and then we just always kind of worked under one account.
And it would just show up Netflix through kind of the Apple ecosystem and then Netflix directly. And it was almost hidden in one area and not in the other. And how long did that happen? Here's the funniest thing that I learned on expenses. So I don't know how this came about, but when I moved into my house well over thirteen years ago, I had a phone line for all of five minutes.
And we said, we need to cancel that because we had cell phones, we're like, we don't need it. And we were thinking, oh, with kids, we need to have it. What happens if something happens in the house and they don't have cell phones at the time and they were younger, so they didn't. So we had a landline, but then we realized we didn't need it. So I called the phone company and canceled the landline.
Well, they didn't eventually cancel it. So what happened is, and it could have been a mistake on my part, their part. So then I was going through the line item with trying to reduce the overall cost of the monthly expenditure for cable or whatever it was, or for internet. And I saw this line item of $25 And I said, what is this? Oh, that's your landline.
And I'm on the phone. I'm like, how is that still there? I said, I canceled that, like, thirteen years ago. And he goes, oh, no. It's been on your bill every month.
And it was kind of buried nestled in, and you have to really look through the line item. And I didn't know if it was just one of those standard fees, but it literally once I read it, my fault. Once I read it so $25 per month times twelve months times well over ten years. Darn. So there are benefits for going through this exercise, and I am guilty of some of those hidden expenses where I just didn't even pay attention.
And I'm the one who manages the money in the house. I should have known that.
Rob: You needed that a that that, landline for your dial up AOL at the time.
Brent: You know that's what it was Definitely. For Armageddon when all cell phones go out in the world. Like, something's going to happen. So Rob, as we close out today's conversation, we've had the whole idea here was getting honest with your money. This isn't a budgeting exercise.
This is not a restriction exercise. This is about understanding your reality. And the avoidance of this is really makes your life a little bit more complicated in my perspective, because you don't have clarity. You don't understand how you could simplify things, but may give you those options that you've been asking for. You may trim a few things.
You're like, gosh, that just feels better. I trimmed $200 a month. I didn't even know I clearly did that a few times. So it creeps up and doing this doesn't force you to make a decision on anything. It doesn't force you into a pigeonhole.
It may just give you that direction that you need to really give you confidence on where you're headed next. So I'm super excited that we had a chance to talk about this because I've learned throughout my entire adult life so much about this topic, all the pitfalls that I've made. But once I really started to consolidate things down, make my life a little bit simpler, it just gave me much more clarity. So as we like to close out episodes, and this is something that we've been doing more recently, is we like to give a shout out to one of our listeners or a friend or somebody that makes a comment. And a little while back, we had an episode with a guest, his name is Ron, and where he went back to law school.
And one listener at the age of 50, and he finished law school and he did something completely new and unique. So one listener responded on Substack and he said, wow. He goes, I've got something that I want to do. I want to run a marathon, specifically the Disney marathon. So here's my challenge to that listener.
Go for it. Done a few marathons. Rob, you've done a few marathons. There's a lot of ways you can prepare for a marathon. Go for it.
It's a rewarding experience. I won't say that it's easy because it's not, but it could be a ton of fun. And I'm assuming I've never done the Disney marathon, but I'm assuming it would be amazing because it's a part of the theme parks and all the things and all the activities. So my challenge back to that listener is go for it. We believe in you.
We're cheering you on. So thanks everybody for listening today. And always remember, you are the director of your next great act.
Lena: That's it for this episode of Midlife Circus. Visit midlifecircus.fm for show notes, transcripts, and all the latest happenings. And be sure to join us in the Midlife Circus community on Substack. Follow Midlife Circus on Apple podcasts, YouTube, and wherever you get your podcasts so you never miss your next great act. Quick reminder, the opinions and stories shared here are personal reflections, not professional advice.
This show is for entertainment and inspiration only. Thanks for listening, and we'll see you under the big top next time. Midlife Circus is a Burning Matches Media production.