The Role of Wisdom in Financial Planning

Our 2 Cents – Episode #135

Welcome back to another great Our 2 Cents episode with Steve and Gabriel Lewit! In store for today is a thoughtful conversation about the wisdom that comes with age and experience, and how it impacts your financial planning. Plus, they’re sharing fun quotes and big money regrets!

  1. Gabriel’s Quote Picks of the Month:
    • “If you’re shopping for stocks, choose them the way you’d buy groceries, not the way you’d buy perfume.” – Benjamin Graham
    • “You can live to be a hundred if you give up all things that make you want to live to be a hundred.” – Woody Allen

  2. The Role of Wisdom in Financial Planning:
    • How does age impact wisdom, and wisdom impact your financial planning?
    • Why you should be thinking deeper about your retirement, not just surface level planning.
    • The importance of incorporating your, and other people’s, life experiences and lessons into your financial planning.
  3. Baby Boomers’ Big Money Regrets:
    • From swimming pools and recreational vehicles to lavish weddings and more! Baby Boomers are sharing what purchases they made after retiring that they regret.

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Podcast Transcript

Announcer: You are listening to Our 2 Cents with the team from SGL Financial, Building Wealth for Life. Steve Lewit is the president of SGL Financial and Gabriel Lewit is the CEO. They’re here to discuss all the latest and financial news, trends, strategies, and more.

Gabriel Lewit: Hello everybody. Welcome to Our 2 Cents. This is Gabriel Lewit. Steven Lewit and producer Katie sitting on the background. In the background.

Steve Lewit: In the background. How do you sit on the background?

Gabriel Lewit: You can’t.

Steve Lewit: It’s impossible.

Gabriel Lewit: But we are all here to give you a great show today and we’ve got a couple fun topics lined up for you.

Steve Lewit: Yeah. Should be good.

Gabriel Lewit: Not a lot currently I’d say happening in the news.

Steve Lewit: Well, there’s a lot, but I’m getting tired of talking about it. I think that’s more… We’re tired of talking about it.

Gabriel Lewit: It’s funny, we sometimes say you shouldn’t read the news because there’s hardly ever anything good on it. You just hear about all sorts of negative things. So today I think we’re going to talk about some different topics other than current events and just continue to give you some insights into the world of financial and retirement planning.

Steve Lewit: And thinking, retirement thinking and also planning and thinking.

Gabriel Lewit: Sure. Yeah, yeah, of course. So actually, speaking of thinking, I’m going to give you some thoughtful quotes here to kick off today’s show that we’ve custom curated for you.

Steve Lewit: See how I led you into that transition?

Gabriel Lewit: Oh yeah.

Steve Lewit: Totally by accident folks.

Gabriel Lewit: All right, so here’s your first quote for today, and this one comes from the famous Benjamin Graham. Okay. It says, if you’re shopping for stocks, choose them the way you’d buy groceries not the way you’d buy perfume or cologne.

Steve Lewit: Oh, Who’s Benjamin Graham?

Gabriel Lewit: I don’t know.

Steve Lewit: I don’t know either.

Gabriel Lewit: That’s why I said “the” famous.

Steve Lewit: Right. Okay. I thought you actually-

Gabriel Lewit: I’m assuming if somebody quoted him, he’s famous.

Steve Lewit: I thought you actually knew who this person was.

Gabriel Lewit: I don’t see any quotes for Gabriel Lewit on the website.

Steve Lewit: Katie’s on the ball. Her fingers are moving and she’s typing.

Gabriel Lewit: Oh, American economist. Okay, here we go.

Steve Lewit: Benjamin Graham. I never heard of Benjamin. I’m an economist.

Gabriel Lewit: You haven’t heard of Benjamin Graham?

Steve Lewit: I studied a lot of economy and I’ve never heard of Benjamin Graham.

Gabriel Lewit: He Was a British born American economist. The father of value investing. Oh yeah, that’s where I heard his name before. Yeah, no, I definitely had heard of him. I just had forgotten who he was. But what do you think about that quote?

Steve Lewit: All right, could you read it again because we got off on to a side-

Gabriel Lewit: You drank a cup of coffee.

Steve Lewit: I drank my coffee. We went on. Who was this guy? Read it again, Gabriel.

Gabriel Lewit: Everybody ready?

Steve Lewit: Everybody’s ready.

Gabriel Lewit: If you’re shopping for stocks choose them the way you’d buy groceries, not the way you’d buy perfume or cologne.

Steve Lewit: Well, what he’s saying I think is that-

Gabriel Lewit: Do you really not know?

Steve Lewit: I know what he’s saying. He’s saying you don’t buy stocks because they look great or they’re showy. He’s saying buy the staple kinds of stocks because of the father of value investing, and value investing it says, what’s the inherent value of the stock, not is it growing because it’s got a hot topic or a title like its pharmaceuticals or its technology and you’re buying it because it’s really a shiny object.

Gabriel Lewit: So, you want to know what’s funny?

Steve Lewit: What’s funny?

Gabriel Lewit: Is I was prepared for you to say something totally what I would consider probably incorrect, and you actually surprised me. I think, I don’t know. That’s not what I was thinking he meant by it. But I actually think you might be onto something there.

Steve Lewit: Once in a while the dog finds the bone once in a while. So what did you think? What did you think?

Gabriel Lewit: I thought he was just speaking of diversification. You’re only going to buy one bottle of cologne and when you go to the grocery store, you usually buy a wide variety of groceries.

Steve Lewit: And you know what? Had we not looked it up and told he was the father of value investing I would’ve said the same thing as you.

Gabriel Lewit: You might be correct on that.

Steve Lewit: Yeah, I would’ve said the same thing as you do.

Gabriel Lewit: Or maybe both are applicable. Maybe he meant two and one.

Steve Lewit: No, no, he’s a value investor.

Gabriel Lewit: Oh, you think yours is the correct interpretation?

Steve Lewit: Well, based on my understanding of who he is and how he thinks, value is, what is driving his decisions, what is the value, the real value, not the superficial value.

Gabriel Lewit: We need a seance now with him to see who’s correct.

Steve Lewit: No, no, no, no. I’m being serious.

Gabriel Lewit: All right, I got another quote for you.

Steve Lewit: Are we done with that one?

Gabriel Lewit: I was moving on from it.

Steve Lewit: Yeah, I guess we are moving on.

Gabriel Lewit: Well, I didn’t want to spend too much time on them. Okay. So this one’s from the famous Woody Allen. Okay. Do you know who he is?

Steve Lewit: Shush. Go away.

Gabriel Lewit: Should we Google him too?

Steve Lewit: No, the question is do you know who he is. Of course, I know who he is.

Gabriel Lewit: He’s a director, right?

Steve Lewit: I grew up with Woody-

Gabriel Lewit: He’s a film director.

Steve Lewit: Film director, comedian. Kind of a weird person.

Gabriel Lewit: Yeah. So he says you can live to be a hundred if you give up all the things that make you want to live to be a hundred.

Steve Lewit: That’s crazy. What do you think of that?

Gabriel Lewit: I think there’s some truth to that. You know, read all the health tips and they’re like, never eat any sugar ever. Never eat any alcohol ever. Or drink alcohol ever. Never. It’s like, yeah, by the time you’re done, you would live probably 20 years longer, but you’re not going to have any fun.

Steve Lewit: Yeah, Woody Allen was a weird guy. You should watch some of his stuff.

Gabriel Lewit: I think I remember I used to watch some of it, and I didn’t love it back in the day.

Steve Lewit: Well, he was very talky, just ordinary talk. All of his movies are that way and kind of weird angles of kinds of stuff. Kind of interesting. He was never one of my favorite people because I thought he was like a woos and just a complainer.

Gabriel Lewit: A woos?

Steve Lewit: A complainer. You know people that complain all the time and well, that kind of person. That was Woody Allen to me.

Gabriel Lewit: So, you don’t like complainers?

Steve Lewit: And I don’t like his quote.

Gabriel Lewit: You don’t like his— Why don’t you like his quote?

Steve Lewit: I don’t know. It’s just like, yeah, okay. Yeah. I want to live to a hundred. I’m not going to give up anything.

Gabriel Lewit: Well, okay, that’s a good idea. Yeah, I mean that’s a good goal.

Steve Lewit: Yeah, I think folks, you just set your goal. You want to live to a hundred, then live a hundred.

Gabriel Lewit: Smoke like a pack a day. Drink a couple six packs every day. Give it a whirl. See what happens.

Steve Lewit: Does it really matter if you live to a hundred?

Gabriel Lewit: Never exercise.

Steve Lewit: No, I didn’t say that because your body needs to feel good. You need to feel good emotionally. You got to treat yourself sometimes to the pastry after the end of the meal. You got to do good things to make you feel yourself feel better. And that’s how you get to a hundred. Now you need a little luck too.

Gabriel Lewit: This isn’t a philosophical analysis. It’s a quote.

Steve Lewit: No, I’m being totally practical. Is that if you want… That’s Woody Allen. You see it’s kind of sly things in there that are… It’s like Woody, stop it.

Gabriel Lewit: Folks. I think I pushed the button.

Steve Lewit: Just stop it. If you want to live to a hundred-

Gabriel Lewit: I didn’t realize you had such strong anti Woody Allen feelings.

Steve Lewit: Here’s how easy it is.

Gabriel Lewit: I would’ve picked a different quote for us.

Steve Lewit: You set your time that you want to live to and just keep doing it and if it works out, great.

Gabriel Lewit: From Steven Lewit. Katie, let’s get that on the website.

Steve Lewit: If it doesn’t-

Gabriel Lewit: You set the time you want to do things to and then you just do it.

Steve Lewit: You just do it. If it doesn’t work out, it doesn’t work out. If it works out, you say, man, I did it.

Gabriel Lewit: You heard it here folks. Steven Lewit.

Steve Lewit: First. You heard it here first, not just heard it here. You heard it here first.

Gabriel Lewit: All right, let’s move into our topic for today.

Steve Lewit: Are we off on a compelling start or is this kind of-

Gabriel Lewit: I’m not sure yet.

Steve Lewit: I hope we’re compelling you folks.

Gabriel Lewit: Well, I think we made some good progress with our metaphors and examples here. And quotes. Yeah. All right. Well, Steve picked out our top for today. I picked a couple options for him and he has selected the following for us here, folks. And it’s basically talking about age and wisdom that is learned from age. Which is kind of went well with that quote, I guess. So you’re seemingly in a philosophical mood, so this might be a good one for us today.

All right, so basically, how does age impact wisdom? And then how does wisdom impact your financial planning? That’s effectively the theme of what we’re going to discuss here for the next 5 or 10 minutes. So naturally, when you learn things as you get older, you can look back and talk to your younger self and say, man, if I had only known X, Y or Z, I would’ve done A, B, or C differently.

Steve Lewit: All right, Gabriel, so I want to back up.

Gabriel Lewit: Have you ever had that before?

Steve Lewit: I want to back up. What is wisdom? I want to back up and because this is so important because wisdom… Is wisdom always a matter of learning stuff or because I’ve met… I think you’re a wise person. You have less years on earth than I do.

Gabriel Lewit: So, I think wisdom-

Steve Lewit: But I think you have a lot of wisdom.

Gabriel Lewit: Well, wisdom as tells us right now, it says the quality of having experience, knowledge, good judgment, and the quality of being wise. Of course, you’re not supposed to use the, they should know better than that. They can’t use-

Steve Lewit: The word wise. Yeah. The definition of wisdom.

Gabriel Lewit: Come on now Well, so if it’s the quality of having experience and knowledge, then the older one is just by default they would have generally speaking, more experience and more knowledge to pull from.

Steve Lewit: Exactly.

Gabriel Lewit: That is wisdom.

Steve Lewit: Well, it’s part of wisdom because this makes it seem like you have to be old to be wise. And I don’t buy that.

Gabriel Lewit: No. It’s saying you typically will get more wisdom as you get older. Doesn’t say they have to go hand in hand. But let’s not get bogged down here in the definition of wisdom.

Steve Lewit: All Right. So in financial planning, I agree. In financial planning, wisdom is I think what wisdom we bring to the table, for example, you and I, is the experience of dealing with this subject of retirement 24 hours a day and seeing all the things that other people can’t see. And so is wisdom being able to see things that other people can’t see, and is that wisdom gained by all the experience? I’d say yes.

Gabriel Lewit: Yes.

Steve Lewit: Yes.

Gabriel Lewit: I think we’re in agreement there.

Steve Lewit: Yes. So wisdom and financial planning is understanding and knowing, look, this could go wrong, this could go right. There are times that the market collapses, there are recessions and being able to see into that, so it’s not fearful.

Gabriel Lewit: Yes. I think those are good points.

Steve Lewit: You’re not going to say anything more than that.

Gabriel Lewit: You want me to give you a hard time?

Steve Lewit: No, no, I just want-

Gabriel Lewit: What kind is that, Steve?

Steve Lewit: I don’t want to dominate the philosophical argument here.

Gabriel Lewit: No, no. I think that’s setting the table well for us here.

Steve Lewit: Yeah, for example, as you get older, your financial goals change. And you have to recognize that as you get older, you don’t want to invest like you are when you are a child or a young person or a young adult. So wisdom is seeing these changes. It’s like your body, you get older. I work out, but I can’t work out like you work out.

Gabriel Lewit: Why?

Steve Lewit: Because I hurt myself.

Gabriel Lewit: You’re assuming I’m working out right now.

Steve Lewit: I didn’t want to go there.

Gabriel Lewit: Yeah, I see why you put that in the show here.

Steve Lewit: No, but wisdom is understanding your body, what it can do and what it can’t do. And that comes from living a long life or living years on earth. When I talk to your sister who is 22, she has some very wise things, but there’s other things that she’s blindsided. She can’t see it because she doesn’t have the life experience to see it.

Gabriel Lewit: So, I think that’s really important when it comes to retirement planning. And there’s a couple key areas that can get into, okay. And the first is, I think when you’re younger you don’t really fully understand. I’ve asked younger clients of mine, “Hey, what are your goals for retirement?” And most of them sort of stare at me blankly and they’re just like, “I don’t know, you just retire and live comfortably.” Because they just never thought about it.

Steve Lewit: Exactly.

Gabriel Lewit: Many young people. Now, I think about it a lot because I coach clients on it a lot every day. And so it’s a little different, but I’ve even talked to people five years away from retirement and I say things like, “What would you like your ideal or dream retirement to be?” And they look at me like, “Ah.” So from my perspective, having gone through it so much, it’s similar to someone that’s been through their retirement and then they could look back and say, “Hey, I probably should have done this, or maybe I really like doing this, or I didn’t like doing this.” And so they have the benefit of hindsight and experience more wisdom. And I think part of our job as advisors is to help give people that have not yet experienced certain things or have the chance to go through it those perspectives so that they can look ahead and plan more effectively.

Steve Lewit: Which is sharing your wisdom.

Gabriel Lewit: Exactly.

Steve Lewit: With someone that’s willing to listen. What I find unfortunate is that a lot of younger people are not hiring advisors. They’re not looking, they think they know how to do it, and they know up to a point how to do it, but they really don’t know.

Gabriel Lewit: This is not a new phenomenon. I would say most, many, not most, many younger people have, what’s it called? Headstrong? Is that the word? Stubbornness.

Steve Lewit: I wasn’t like that when I was younger.

Gabriel Lewit: You know where they think they know better than those with more age and more experience and more wisdom.

Steve Lewit: I never had that.

Gabriel Lewit: So that’s also very common too. And those two tend to go hand in hand. Parents are always trying to teach their kids. Kids think they know better than their parents.

Steve Lewit: I listened to everything my parents told me.

Gabriel Lewit: And kids? Just kidding.

Steve Lewit: That’s not true.

Gabriel Lewit: Well, okay, what are some of the things that I see? Let’s get into some meat and potatoes here. Your wisdom. So first is if you’re younger or even approaching retirement and you’re thinking about your retirement, you really want to start thinking deeper, I think would be my phrase. So many people that I talk to just give this sort of stock answer like, “Oh, I just want to be comfortable.” And look, at the end of the day, you want to turn your brain off of what’s called autopilot. I read a great book, I can’t take credit for this phrase. And basically what he was saying is everybody goes through life sort of on autopilot, and they don’t take the time to stop and set aside and really think. And so the autopilot answer is, “Oh, I’m going to retire 65 and I just want to live a comfortable lifestyle and maybe travel just a little bit.”

And I must hear that answer eight out of every 10 times I ask that question. And then the other two out of 10 times I get a response that shows me someone’s really, I think sat down and taken the time to know themselves, to think about who they are, what they want. And I get answers like, “I’d like to go travel to so-and-so where my relatives grew up. I’d like to go do this. I’d like to take up a couple new hobbies. I’d like, yeah,”

Steve Lewit: Yeah. I had a client, “I want to go to the Corvette Racing School.” And it’s like, that’s great. I love that. That’s an actual plan.

Gabriel Lewit: And I think we get so hung up in our lives where we don’t have time to really sit and think about the future that you just stick on autopilot in cruise control, and you don’t really even realize there’s truly probably 10,000 unique things that you could do in your retirement. And so many times people are just saying, well, I guess when I get there, I’ll figure it out. But then they keep going through life on this autopilot mode and then they look back later and they say, “Wow, I should’ve done X, Y, or Z differently.”

And that’s what we’re trying to help you avoid is having any of that hindsight regret. I’ve had other clients that they’re 80 years old or upper seventies with multiple millions of dollars, and I’ll have conversations with them and they say, I probably should have spent more or saved a little less when I was younger because now what do I need all this money for? I’m never going to spend it.

Steve Lewit: So, wisdom is opening that window to people who may not see it for themselves. And I love this. That’s a very philosophical quote you gave about living autopilot. Life becomes a habit. It’s just something we do the same thing every day and we work out. And you know what that does? It dulls your brain. It really dulls your aliveness. So what you’re suggesting is to take yourself off autopilot for a day or two or a week, or a year, or forever, and explore in yourself for retirement. What is it I really want to do?

Gabriel Lewit: Well, yeah, it was an interesting book that I read and if anybody wants to know what it was, you can email me, and I’ll share it with you. But there’s some things I liked about it a lot and a there’s a couple things I didn’t. But the other idea was it was semi money related naturally as an advisor, that’s kind of the stuff I read. But it was also just talking about you don’t necessarily want to wait until retirement to start living your life. And I try to share this philosophy a lot with my clients, which is, hey, having a financial plan serves two purposes. Number one, it gives you a roadmap for the future. When you’re at the mall and you see the map of the whole mall and then it says you are here and you see exactly where you are and where you’re trying to get to the store on the other end of the mall.

Steve Lewit: Or it’s like going to the food store to a Whole Foods or wherever you’re shopping, and you have a shopping list. You’re not walking around saying, what did I need again?

Gabriel Lewit: Yeah, so your plan will help you have a roadmap of the future. But the other thing that allows you to do is let’s say for example, we build a retirement plan, we stress test it for you, and I can look and you say, you know what? You’re saving enough, Steve, like you’re on track, the lifestyle you’re living today, if you keep saving max out your 401k, an extra 10 grand here, another five grand here, you’re good. You’re going to have all the money you need.

What you can then do without stress or guilt or worry or fear is take any other money you now have over and above that and spend it and enjoy yourself if you want to. Which would the argument would be, why wouldn’t you? Because when you get to 60, 70, 80, and if you already had all the money you needed to be on track, then you’re probably not going to spend all that money later on in life and you should be, what’s the word, spreading it out over your life to enjoy it along the journey as well.

Steve Lewit: Surely. Surely.

Gabriel Lewit: So that would be some-

Steve Lewit: So, what is the wisdom in that is… What would you say?

Gabriel Lewit: Don’t always put everything off to the future. There’s a balance that you may want to explore.

Steve Lewit: While you’re working.

Gabriel Lewit: While you’re working, while you’re living, while you’re saving.

Steve Lewit: So, some people will sacrifice the early parts of their lives by working 24 hours a day and spending time away from their family and not taking vacations in order to get to the time they can enjoy themselves. And sometimes they don’t get there, or when they get there, they find out it isn’t what they thought it would be, and then they look back and have a sense of disappointment.

Gabriel Lewit: Well, it’s one of the reasons I like reading a lot, and they say people that read lots of books, you’re learning from others. You’re learning from other people’s experiences and perspectives and that can really open up your world of experiences and perspectives as well. So I think that’s a great idea. If you like to read, get out there, buy some new books and check things out. Let’s see, one other, well, let’s maybe pick one other thing. What else can you think of age and wisdom when it comes to retirement planning? And I do have a transition from this into our next topic, which I’ll get to in just a second, but-

Steve Lewit: I felt you were leading me on here.

Gabriel Lewit: We’ll get there in one minute. Anything else you can think of related to what comes top of mind to you, dad, as you think through your client meetings and discussions?

Steve Lewit: I think this is a little philosophical, again, who’s surprised, but the wisdom I like to share with my clients, that is not to look back. In other words, don’t look back and regret what you’ve done because you’ve done it. And I would value what you’ve done rather than say, well, I didn’t do this and I didn’t do this. The question to me, the wisdom I like to bring to the tables, what are we going to do now? What is the plan from today?

Gabriel Lewit: Well, yeah, I think that’s actually really smart, especially-

Steve Lewit: It’s wise. It’s wise.

Gabriel Lewit: Well, I didn’t want to use the word wise again. I was trying to mix it up.

Steve Lewit: No, but we’re talking about wisdom. You have to use the word wise. You can’t use the word smart. It’s different.

Gabriel Lewit: That’s genius.

Steve Lewit: There you go.

Gabriel Lewit: That’s genius.

Steve Lewit: There you go.

Gabriel Lewit: Is that better?

Steve Lewit: Much better.

Gabriel Lewit: Well, because yeah, let’s say you took what I was just saying, man said, wow, I’m maybe you’re 60 and you’re like, wow, I’ve already 60. I didn’t do what Gabe was saying. I haven’t been spending my money. Well, to your point, when would be the next best time to start?

Steve Lewit: Like this afternoon.

Gabriel Lewit: Or they say the next, if you haven’t saved for the future in the past and you’re trying to plan for your retirement, when’s the best next time to start saving?

Steve Lewit: I find a lot of people-

Gabriel Lewit: It’d be today.

Steve Lewit: A lot of people spend time in woulda coulda shoulda. I should have done this. I would’ve done that. I could have done that. And it’s like sometimes I appreciate their perspective and I really appreciate their thinking about it, but sometimes I’d like to pinch them and say, okay, can we stop? Let’s go forward. Because life is going forward not backwards. I think.

Gabriel Lewit: Yeah. All right. Those are some good ones there.

Steve Lewit: I’m waiting for the transition though.

Gabriel Lewit: Well, the transition is… Our next topic is things that people, baby boomers have revisited big money purchases that they decided that they ended up regretting in retirement.

Steve Lewit: So, after that whole lecture on going forward, we’re going backwards. Sort of.

Gabriel Lewit: Well, the idea here is to look at some of the things that other people have experienced and have created opinions upon. Learn from those and then see if they can apply to you. Sometimes things apply and sometimes they don’t.

Steve Lewit: So, let’s talk about you, Gabriel.

Gabriel Lewit: Me?

Steve Lewit: Yeah. We’re going to talk about you. So you are about to spend a small fortune building a pool in your backyard.

Gabriel Lewit: I’m debating it. Yes.

Steve Lewit: Yes. I think you’re going to do it.

Gabriel Lewit: It’s fairly likely. I’ve been thinking about it for a number of years.

Steve Lewit: I’m not sure you’re going to build a pool house.

Gabriel Lewit: I am a perfectionist. I want everything. Give me the deck, the landscaping, the pool house.

Steve Lewit: The deck, the landscape, the pool house, pool here, pool and blah, blah, blah, blah, blah. And you’re probably hiring attendants to take care of it for you.

Gabriel Lewit: I do like that. That would be nice.

Steve Lewit: Like that idea? Okay.

Gabriel Lewit: Definitely no.

Steve Lewit: All right, so lot of baby boomers built pools and you think they regret it or millennials, do you think they regret it?

Gabriel Lewit: Well, I do think some people strongly, you hear it a lot. A lot of people regret building a pool. Yes, but many people love their pool. Yes. So this is one of those. So this is a big purchase, and if you’re thinking about buying or installing a pool, it is one that you want to think long and hard about, which is what I’ve been doing for the last three years.

Steve Lewit: You have.

Gabriel Lewit: Four years.

Steve Lewit: He’s taking his time on this.

Gabriel Lewit: I am taking my time on it because the bigger the purchase, generally speaking, the more cautious you want to be and really make sure you’re thinking it through.

Steve Lewit: Yeah, yeah. It’s interesting. And I don’t want to dampen your enthusiasm because-

Gabriel Lewit: You couldn’t. You couldn’t.

Steve Lewit: Because I’m all in favor of you building a pool and I want you to build a really big pool house, so I have a place to stay for the weekends, but most people-

Gabriel Lewit: It’ll have the pool equipment in there.

Steve Lewit: Most people in this environment that have pools, I sense a regret in their pooling because once the kids are older, they don’t use it.

Gabriel Lewit: Well, to be fair, I have a seven-, six- and three-year-old.

Steve Lewit: Yeah, and I think that’s great.

Gabriel Lewit: So, I think we always like going swimming and we like having the pool, and so I think we’ll get a lot of use out of it. But the regret is that people spend a lot of money on these pools, but they’re just in the house, them and their spouse, and they have all these other things that they want to do in their retirement, and they’re out traveling and they’re out doing X, Y, or Z, and they realize, wow, I barely even use the pool.

Steve Lewit: Exactly. Yeah.

Gabriel Lewit: So, if you’re going to host pool parties a lot, if you’re super social, you have a lot of events at your house, you have the kids and grandkids over a lot, that can be a very different story. But that’s just one of the big items that many people do have regret upon later on down the road.

Steve Lewit: Now, will you regret not putting your pool inside like a pool house that opens-

Gabriel Lewit: Inside?

Steve Lewit: So you can use it in the winter?

Gabriel Lewit: No, I don’t like that.

Steve Lewit: No?

Gabriel Lewit: Nah.

Steve Lewit: All right.

Gabriel Lewit: No, I’ll just get a hot tub for the winter.

Steve Lewit: Okay, I like that. Yeah, I approve.

Gabriel Lewit: All right. What else is on the list here? Well, you’ve got, believe it or not, weddings is another big one. So some retirees, baby boomers, they help their kids with big lavish weddings or grandkids with big lavish weddings and weddings these days, the costs are getting a little bit out of control and actually all sorts of events, bar mitzvahs, weddings, you name it.

So actually one of my neighbors is a event coordinator, and this one moved in down the street a little bit and we got talking and he was showing me pictures of some of the events that he was putting together for birthday parties, for graduation parties, for bar mitzvahs, and some of these people were spending 200, $300,000.

Steve Lewit: And the people that can’t afford it.

Gabriel Lewit: On these lavish, lavish, lavish, 18-year-old graduation parties and just craziness, craziness. I was looking at them like, who does this? So that’s the question. Sounds great in the moment, you’re going to have a great party, but unless you’re obnoxiously rich, are you going to look back and have financial regret there.

Steve Lewit: Well, even if you’re obnoxiously rich, you spend $300,000 on a wedding and two years later your kids get divorced.

Gabriel Lewit: Right.

Steve Lewit: It’s like, wow, I’m not going to do that again.

Gabriel Lewit: Yeah. So the question is what’s your purpose in spending big bucks on a wedding like that? And certainly no one’s saying, don’t chip in for your kid’s wedding or help them out if they need it and you want to, but be cautious on how much you spend there because there’s a lot of regret potential down the road for that kind of expense.

Steve Lewit: I like that. So every decision has regret potential in it. I like that a lot. Great.

Gabriel Lewit: So that’s another one. Another big one is RVs.

Steve Lewit: Oh, I was thinking of buying an RV. What is it? What does it say?

Gabriel Lewit: Well, it says a lot of people buy RVs and then realize they don’t like RVing.

Steve Lewit: Well, can’t they just sell it then.

Gabriel Lewit: Well, like anything new, you drive it off a lot what happens to its value?

Steve Lewit: Goes down.

Gabriel Lewit: Plummets, right? So yeah, the recommendation there is make sure you love RVing first before you buy the RV. Maybe rent one for a weekend.

Steve Lewit: I was thinking of renting an RV for the summer. I said I’d rather buy one than rent one.

Gabriel Lewit: Okay, Steve, I have one that’s very much right up your alley here.

Steve Lewit: It’s got to do with tennis?

Gabriel Lewit: No.

Steve Lewit: Opera.

Gabriel Lewit: The other next big regret is buying a timeshare.

Steve Lewit: Oh, my favorite regret.

Gabriel Lewit: You care to share?

Steve Lewit: No.

Gabriel Lewit: Come on, relive.

Steve Lewit: No, I got suckered in.

Gabriel Lewit: Relive the memory.

Steve Lewit: It’s so easy to get suckered in.

Gabriel Lewit: Come on, share your wisdom. This is wisdom. Learn from experience.

Steve Lewit: You do not take a deal-

Gabriel Lewit: Glean. That was what I was going to say.

Steve Lewit: Everybody knows everybody out there has suffered through timeshare presentations, but I suffered and bought one.

Gabriel Lewit: You’re not going to give me any context from the shop?

Steve Lewit: No. I bought a timeshare. Folks, I never use it. Well, I used it when my kids were young. I used it for you. I have a beautiful timeshare. Anyone wants to use my timeshare just let me know because I don’t use it. You should use my timeshare.

Gabriel Lewit: Why? Can I break it to you?

Steve Lewit: What?

Gabriel Lewit: If you Google. I did look it up.

Steve Lewit: You didn’t Google.

Gabriel Lewit: No, I Googled it. People say don’t go to use these timeshares, because even when you own the timeshare, if you go to use it, they sucker you into new timeshare presentations.

Steve Lewit: Well, you don’t have to go.

Gabriel Lewit: They, well, they say they harass you.

Steve Lewit: They won’t. No, they don’t. No, no, no. They don’t do that.

Gabriel Lewit: I don’t want to do that on my vacation.

Steve Lewit: There are some timeshares though that I think are pretty compelling.

Gabriel Lewit: So, any regrets on your end there, Steve?

Steve Lewit: Yes and no. My regret is that I have to keep pay, even though I’ve paid off the whole thing. I have to pay the maintenance every year and I don’t use it. I’m going to give it to… I’m donating my time… Here, folks. I’m donating my timeshare to the company.

Gabriel Lewit: I don’t want it.

Steve Lewit: I’m giving it to the company.

Gabriel Lewit: Me and you own the company. No one else to give it to. I don’t want it.

Steve Lewit: Let our employees use it.

Gabriel Lewit: I think you should just donate it to somebody who wants it.

Steve Lewit: Katie, you want to use my timeshare? Come on. Why wouldn’t you want to use… It’s beautiful. It’s a great timeshare. Folks. Do not buy a timeshare. You will regret it. Now I have two clients that have timeshares. They use them all the time. Yeah, they have gotten every dollar out of it.

Gabriel Lewit: I guess like anything here, it depends. And this is why we’re sharing these things. You want to really think about them.

Steve Lewit: I regret I bought it. I do regret it.

Gabriel Lewit: Let’s see. How about the next one that some people claim that they regret. This was all off of an article, by the way, folks, I didn’t come up with these. Are these really, really expensive, longer term cruises.

Steve Lewit: What’s a long mean? Eight weeks or 12 weeks.

Gabriel Lewit: Yeah, seven, eight weeks or longer. Those kind of things. So some people have claimed that they did not enjoy that experience.

Steve Lewit: Did they get bored, or does it say?

Gabriel Lewit: The point is they realize after they’re stuck on a… One week is one week that they got on a boat and realized they’re stuck on it for seven weeks. This reminds me, there is a boat now. Funny enough folks, I forget the name of it. Katie, I was going to try to give you something to Google, but where you can buy a condo.

Steve Lewit: On the boat?

Gabriel Lewit: Own it on the boat.

Steve Lewit: That’s a cool idea.

Gabriel Lewit: And you live on the boat full-time, and it just travels around the world. Okay. Oh, it’s called Storylines. Yeah, that’s what it is. Storylines. Okay, so now generally speaking, these are fairly expensive for very small condos on the boat. And then you have to pay like $5,000 a month. And that covers everything. That covers food, whatever. And that’s your budget. And you live on the ship and you cruise around the world.

Steve Lewit: That might be pretty interesting, actually. That might be pretty interesting. I had this, I know we’re running out of time, but I grew up in Manhattan and Manhattan has different docking state, what do you call it? Piers, where you put the sailboats and all of that? Well, I had a friend who had a houseboat right on the Hudson River. And to me that was like, this is so cool.

Gabriel Lewit: I mean, you should get a houseboat.

Steve Lewit: We went to his houseboat. It was just the coolest thing in the world. And he lived on a houseboat.

Gabriel Lewit: There you go. There you go. I could see you doing that.

Steve Lewit: But a condo, that means I got to go home to the boat.

Gabriel Lewit: The boat is your home.

Steve Lewit: The boat is my home.

Gabriel Lewit: There is nowhere else to go. You don’t have a yard. If you’re in the middle of the ocean, you can’t run to the grocery store. You are on the boat.

Steve Lewit: You’re on the boat, but the boat docks.

Gabriel Lewit: And if you don’t like your neighbors, you’re on the boat.

Steve Lewit: You’re on the boat.

Gabriel Lewit: So yeah, to each their own, I suppose. I don’t think I would like that.

Steve Lewit: I bet it’s a good investment. I bet people would buy that.

Gabriel Lewit: I don’t know.

Steve Lewit: I’m going to look it up.

Gabriel Lewit: There you go.

Steve Lewit: Oh, I’m going to regret that too.

Gabriel Lewit: Speaking of regrets, boats, people tend to regret their boats also.

Steve Lewit: Oh, always. Always.

Gabriel Lewit: All right guys. Well that was our show here for today and we hope you had a good time joining us for some conversation and thoughts. So if you have any questions on anything there or you want to share any of your experiences with us, we’d love to hear. You can reach out to us at or if you want to call us to schedule a time to talk about anything or schedule an appointment. Our number is (847) 499-3330. Otherwise, we just hope you have a terrific day. How about this amazing spring weather we’re having?

Steve Lewit: I am loving it.

Gabriel Lewit: It’s terrific. And then also go Bulls because on the date that we’re recording this, they at least won their first play in game. Avid Bulls fan.

Steve Lewit: They’re going to lose today.

Gabriel Lewit: And they are going to win on Friday against the Heat, which we’ll know by the time you listen to the show, if I’m right or wrong.

Steve Lewit: They’re not going to win.

Gabriel Lewit: And then they will be officially in the playoffs where they’re going to go and win the championship.

Steve Lewit: I may regret I said that.

Gabriel Lewit: So that’s my hope and dream at least. All right, well have a wonderful day. We’ll talk to you on the next one.

Steve Lewit: Stay well, stay safe. See ya.

Announcer: Thanks for listening to Our 2 Cents with Steve and Gabriel Lewit. For any questions about your finances, give SGL a call at (847) 499-3330 or visit us on the web at and be sure to subscribe to join us on next week’s episode.

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