Afford Anything - Q&A: You Made a Money Mistake. Now What?

Episode Date: March 25, 2025

#593: An anonymous caller is brooding over a mistake he made in 2023 when he decided to contribute to his Roth instead of a pre-tax account. How does he get over this? June is annoyed that she triggered short-term capital gains and wash sales when she sold assets in her taxable brokerage last year. How does she avoid these issues in the future? Zerai wants to add mid and small-cap exposure, but his 457 plan has a limited selection of mutual funds. What’s the proper way to select the best fund among the available options? Former financial planner Joe Saul-Sehy and I tackle these questions in today’s episode. Enjoy! P.S. Got a question? Leave it https://affordanything.com/voicemail For more information, visit the show notes at https://affordanything.com/episode593 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe, have you ever made a financial mistake and then just brooded over it? I thought you were asking me if I ever made a financial mistake. No. I've never made a mistake, ever. Well, we are going to answer a question from a caller who is wondering, how do you stop ruminating and self-flagellating over these financial mistakes? We're also going to answer questions about short-term capital gains, about mid and small-cap exposure, about all of the, financial questions that keep us up at night that hopefully won't become mistakes.

Welcome to the Afford Anything Podcast, the show that understands you can afford anything, but not everything. Every choice carries a tradeoff. And that applies to your time, money, focus, and energy to all limited resources you need to manage. This show covers five pillars, financial psychology, increasing your income, investing, real estate and entrepreneurship. It's double eye fire. I'm your host, Paula Pant, every other episode. We answer questions that come from you, and I do so with my buddy. The former financial planner, Joe Salcie High. What's up, Joe? Hey, Paula, what's happening? I'm so excited to answer three fantastic questions, the first of which comes from Anonymous. Hi, Paula and Joe. Thanks for a

great podcast. Love listening to it, especially the Q&A episodes. My name's Anonymous. I wanted to call in because I've been listening with really great interest the last few weeks when you've been discussing this Roth versus pre-tax decision that people have to make in various forms. And I think personally, I just made a mistake. After I listened to the discussion, I went back and I looked at what I had done in 2023 and 2024. And I think I just made a categorical error. You know, I'm sure I'll make many more errors in the future.

It'd be great to know how to just shrug it off and move on if you have any personal takes us to the best way to do that. So the categorical error that I think I made here is in 2023, I maxed out my 401k in Roth dollars at the 32% tax bracket, even though I knew in the next year I would be in the 24% tax bracket. Isn't this an error because I should have done pre-tax in 2023, knowing my tax bracket would drop the very next year, and then I could just do a conversion of my 401k dollars into Roth dollars the very next year and shave off a few percentage points from 32% to 24%. And I think I can hear Joe saying, who cares, it's only 8% and you can't optimize everything in life. But,

you know, people like us, we like to try to optimize things. And sometimes it's fun. To provide a little bit more context, the contribution in 2023 would have been my only pretext dollar. So when I did the conversion, it literally would have been just the 23K getting converted. Did I make a mistake here? And if I did, do you have advice generally as to how to go about dealing with things like this? And by the way, I hope you tell me I didn't make a mistake. That would be even more ideal. if there's any way in which I didn't, feel free to let me know. But I appreciate your input. I appreciate your advice. And thank you again for a wonderful podcast. Anonymous, thank you for a wonderful question. And before we answer it, the first thing we need to do is give you a name.

Well, no, he said his name is anonymous. But really, Paula, nobody names their kid anonymous. I mean, come on. So you're right. I suppose we should give him a name because that's awful. I wonder if, is there like a birth certificate registry? Are there people who are actually named anonymous? there's got to be somebody. Yeah, there's got to be at least in a country of 330 million people. There's got to be at least one person. I heard a comedian recently talking about how he met these two people. Maybe it was Nate Pagasy. He talked about he met these two people and their names were Bill and Jane Doe. And he goes, what's the chances? He goes, and that took me 20 years to realize. They were messing with me the entire time. I thought it was normally John Doe, right? John Doe and Jane Doe?

It very well might have been. That was probably my memory. memory leaking right there. See, I make mistakes too, anonymous, right there. I probably made another one. A couple weeks ago on stacking Benjamin's, I said, we are making lemons out of lemonade. I actually had a friend who once said, hey, when life hands you melons, and then he like stopped and didn't know how to finish the sentence. And so from that moment forward, all of us keep teasing him about, hey, make melanade.

You got to make melanchade out of your melons. Make some melanade. Come on. But okay, so we've got three things to do. We've got to give anonymous name. Then we've got to answer whether or not he made a mistake. And then the most interesting part of the question, in my view, is going to be opening this up to a broader discussion around. How do you deal with financial mistakes?

Psychologically? How do you deal with the guilt, the shame, the rumination, the self-flagellation, the kicking yourself for what might have been? because I think this is something universal. This is something I believe every single person who is listening to this podcast has experienced or is experiencing. Because no matter who you are, you've made mistakes. And guess what? You're going to make even bigger mistakes in the future. And you're going to make mistakes with more zeros on the end.

You're going to make orders of magnitude bigger mistakes than you have ever made before in your life. You've got that to look forward to. Well, this is a mistake. And I think he already knows this. Paula. I don't think that's going to end the way. world for him. And you know what? The fact that he's saving more money is still pretty badass already. So I think if we look at a mistake that ended up being serendipity, I think that's my favorite

word lately, serendipity. I think that's the way we go. So John Kellogg one night had, have you ever, Paula, had this? It is called Wheatberry dough. Wheatberry dough. No. I've never had. Oh, delicious. I don't even know what wheatberry dough is. But a guy named John Kellogg left out a batch of wheat berry dough. And he had been rolling some things for his bakery to make these different items. Well, the next day it was all stale.

And he decided rather than throw it out to run it through his rollers and he toasted it. And that developed maybe the best selling cereal of all time, the cornflake. Oh, so Kellogg's cornflakes was actually a mistake. A mistake. It was a mistake that turned into an empire. How about that? So I think we can call him John. That story reminds me of a similar story that I read about in The Economist a couple of weeks ago. In 1888, in a coastal province in southern China, a man by the name of Li Kumshung was boiling some oyster soup on the stove.

He forgot about it, left it out a little bit too long, and, when he remembered that he was cooking this oyster soup, it had boiled down into this really thick gravy. Well, that became oyster sauce. And he went on to package it, sell it, and turn it into a company that now has a worth of $17.7 billion. Wow. Wow. For himself and his airs. How about 3M, Paula, try and develop a substance that would never give up that would stick things together forever like a super super glue? And instead, they accidentally created something that would never completely stick, aka the Post-it Note. Mildly successful product, the Post-it note. Don't know if you've ever heard of it. But I'm sure John is wondering,

John, our anonymous caller, is wondering, are these examples relevant? Because his mistake is not something that's going to lead to business growth. He didn't accidentally create a new product. He simply may have contributed to an account with the suboptimal tax treatment. That's not something that spurs innovation, like the examples that we're sharing. Is that a mistake that has redemption? Here's the thing that I was thinking, Paula. Yes, this is a huge mistake. He's going to pay for it forever. I would be so incredibly frustrated. with my life. I'm not sure I would ever recover. Oh, Joe. And I hope John and everybody else, here's my sarcasm, because for me, we go to college, not everybody, but many of us go to college,

or we take courses and we pay for that education. The way I think I look at this, Paula, is this was an education cost, because you know what, this might happen again. And even if it doesn't happen again, the fact that now he has a mental process of thinking, okay, what's happening next year? What is my overall tax strategy as I look at this? I chalk this up to education cost, 100%. Not something that's going to, I love him already preempting me on this. This isn't something that's going to ruin his ability to retire or not retire. It's just simply the cost of education as he learns a lesson that's not.

not the end of the world. Right. I call it the school of hard knocks. And tuition in the school of hard knocks can be expensive. And the thing is, in his particular case, it sounds as though he had absolute certainty that his tax bracket was going to drop in the following year. But for a lot of people listening, they don't have that level of certainty. So there are a lot of people listening who are in a high tax bracket in one given year. And then the following year, they suspect that they might be in a lower bracket, but they don't necessarily know that. Sometimes you have unexpected bursts of income, you get a random commission check that you weren't expecting, you get a bonus that you weren't expecting. Sometimes you just get unanticipated income that leads you to make more

money than you thought you would. And so it sounds as though in his particular case, he anticipated dropping into a much lower tax bracket in the following year. And it sounds as though that is what actually happened. But in many cases, even if you do anticipate dropping into a lower tax bracket, that ends up not happening. Or the tax bracket differential is not as steep as you thought it would be because of some unanticipated income. Well, and I see when people flagellate themselves over things that they didn't know because they didn't like the outcome that came. And they go, oh, look at what happened. This is absolutely horrible. Those are the ones, Paula, that when I was a financial planner drove me crazy. There was no way to see it come.

There was no way to see the Black Swan event coming. You look at all the things that you did and you're still not sleeping at night because the outcome wasn't something that you wanted. This for me comes down to outlook more than anything, like how we see the world in our place in it. Right. But I think the harder situations are the ones in which you say to yourself, oh, I should have known better. In John's case, because he knew with such clarity that his tax bracket was going to drop, it's easy for him to say, well, I should have known better. I should have anticipated that. I think that's where that self-flagellation comes in. Sure. And for many of us, it's easy to carry that same line of thinking into all kinds of financial decisions. Oh, I had too much of my portfolio invested in crypto and I knew that my asset allocation was out of whack, but I got a little irrationally exuberant. I should have known better, but I did it anyway. I think it still comes down to outlook, though. I think it still comes down to where I see my place in the world, this self-judgment of I should have seen that. I should have. have not done that. I think it's because we're expecting ourselves to be perfect. Let me tell you,

Paul, I guess what I'm driving at here is that I really like this idea of a growth mentality, and I love the idea of paying tuition cost because when I'm paying tuition costs, I'm going to school, and I'm thinking of my life as a science experiment, and I'm the guinea pig. And then I think that when I think of a science experiment, I'm not going to get the experiment right the first time. It's not always going to happen. So I'm approaching everything with a curiosity that includes, oh, guess what? That didn't work. That's amazing that that didn't work. That's fantastic. It didn't work. I just found out that didn't work. And that's great. But when we expect perfection from ourselves, that's what I think creates the self flagellation. Right. Exactly. I love the guinea pig analogy, especially for people that are thinking about what do I want to do when I'm old. How many people do you know that retired early and they thought it was going to be all unicorns and rainbows, Paula? And then they show up and they're still the same exact person. And that person is not unicorns and rainbows.

It's exactly the person I was the day before I decided to make this move. So instead of thinking about the future as if it's something disconnected from today, if I look at the actions I take today to connect them to the future, I'm saying, okay, you know what, I'm going to take a vacation in these places where I think I might want to move to when I'm older, let's say. If I'm going to do geo-arbitrage, let's try those out. How many times have we heard from people that go, oh, yeah, I went to this country and I thought it was going to be amazing because everybody said that Panama's amazing and it turns out I didn't like it at all. I'm going to Panama in a few weeks, Joe. And you think it's going to be amazing. I do think it's going to be amazing. Absolutely. We will find out. I will let you know in April. But how much fun does it make your vacation today when it's a lab rat for who you're going to be tomorrow?

You know what I mean? Now all of a sudden, I'm going to Panama and I'm going, okay, what are the locals like? How would I fit in here? What are the cost of apartments right now? What is the political climate like? How many people speak English? How much am I going to need to speak the local dialect versus the broader tongue? Just all of these exciting things that I can dig into.

In that case, I'm a lab rat. versus I get to financial independence. I moved to Panama. I've never been there before and I hate it. And then I self-flagellate and go, why did I decide to move to Panama? That was stupid. No, it wasn't dumb at all.

You're focusing, I think, on the wrong aspects. Joe, I like your point about how kicking yourself about mistakes can often be a sign of perfectionism, like expecting too much from yourself because we are, to use the words of Rameet Safi. cognitive misers. There is only so much cognitive bandwidth that we can give to anything. And thinking about X comes at the cost of thinking about Y. That's the whole notion of affording anything. It's the notion of opportunity cost. And so, John, I bet that in the absence of thinking about arbitraging your top marginal tax bracket, in the absence of devoting cognitive bandwidth to that, you were probably thinking about other very important things. You were probably thinking about

how do I make sure I'm maintaining good cardio health? How do I make sure I'm still maintaining good muscle as I age? There are all of these aspects of a good life that require brain power. I mean, even something is as seemingly simple as how do I develop a routine in which I am regularly flossing, something that I know I quote unquote should do, and yet I don't, right? How do I bake that into my routine? Because once it becomes a habit, then it's mindless, but the very act of making that a habit requires upfront cognitive load. And that cognitive load has to come from somewhere. And so you simply can't think of everything and you can't devote that cognitive space to everything and it's okay to let yourself be at the 80-20 of certain things so that you can make sure

that you're directing your very limited attention towards the few things that will actually matter. And I love that you bring up the things that actually matter because the word that comes to mind when it comes to any type of pain is the word useful. because I believe that mulling over something over and over and over, if I don't turn it into something that affects my future, that's not a useful time. And I understand that for some people, that they're having trauma issues, Paula, so I don't want to address those. That's a whole different issue. But for people with this passing, I should have done the Roth IRA differently, right? With something like this, I think I have to think about utility. And my first thing, thought when I start to self-flagellate is, and this is a learned skill over time during my life, it isn't something I used to do. But I actually had a mentor that taught me this that when I start to self-flagellate, think, how do I make this useful? Is there a way to make it so that I do something different in the future? So, as an example, if we're talking about this Roth IRA move,

is there a checklist that I can create that I run down like a pilot getting ready in pre-flight, right? Oh, gee, my co-host on stacking Benjamin's is a pilot. Whenever we get in his plane, he runs down, Paula, this checklist that people have made over time to make sure that some of these awful accidents we've seen lately don't happen or they minimize the chance of them happening. So is there a checklist he can create? You know what's funny, Paul? Even if I never look at the checklist again, the act of making the checklist and making it useful stops the self-flagellation.

Right. I use a lot of checklists in my rental property business. And one of the things that I routinely do is every time something new comes up, I'm like, oh, great. This is something that I can add to the checklist. So, for example, checking the batteries and just checking the batteries. and just checking the connection in the smoke alarm at every turnover, just verifying the smoke detector at every single tenant turnover. Even if you outsource to property managers,

your property manager is not necessarily going to be doing that. Sure. But I want to make sure that that happens. And so that's checklist. And the way that it came onto the checklist was, I had a tenant once, this was years ago, the tenant moved in and on move-in day, they contacted me. And they said, oh, my smoke detector is like, it's beeping, right?

It's going off. Yeah, it's going off. It's got that really annoying beep going on. And, of course, I'm an out-of-state investor. So that meant that I had to call a contractor and dispatch him out there. He had to charge me a rush fee, right? So it cost $150 to change out the batteries in that smoke detector. Oh, man.

And what the advantage is to being an out-of-state investor is that you only make that mistake once. The first time that you're paying $150 to dispatch a contractor on a rush job to change out a smoke detector, you do that once and boom, it goes on the checklist. That's some tuition right there. Yeah, you never make that mistake again, right? Versus if I had been local, then I might have just gone there myself and done it, and then it wouldn't have ended up on a checklist. The advantage of being out of state is that you are motivated to systematize in that manner.

There's another point here, which is that if you make mistakes again in the right frame of mind, I love the idea of the growth mentality, that these mistakes also become stories that we can use not just for ourselves, but for the people around us to help others in the future. That story that you just told Paula, I bet there's a bunch of your real estate fans that have now just add and check the batteries to their checklist. These growth narratives that we learn from failure are always some of my favorite stories. When I hear people that I think are successful in many areas of their life, share a story about something they really messed up, that also truly resonates. And what's interesting to me is that I feel like those failures, if they're treated

correctly in that vein that they become stories, it helps with our sense of purpose, which increases longevity, because now my purpose is not just to do the thing for me, but it's also to share my mistakes, to share the things that I've learned over time. And if my goal is to serve a greater community, every study shows that increases longevity. And then the second thing that increases longevity is this idea of connections, right? Even if we're a severe introvert, we need these personal connections between people. And so the fact that I can help other people learn from the pain that I had. So a big story that I've shared over the years is when Cheryl and I were very, very seriously dating.

I was thinking about asking her to marry me. I planned this beautiful trip to Chicago, Paula. I buy this hotel room that is at a hotel way above my head. We open up the door and there's this refrigerator that's just full of food. It is just amazing food and drinks and these little alcohol bottles. And we're getting ready to go out for the night. We're going to go to this cool jazz club. So she goes in the bathroom to get ready.

She comes back out. I've got a bud light and a can of pistachio nuts. And she's like, what are you doing? And I said, it's amazing. There's a refrigerator over there that's completely full of food. And she goes, I think you have to pay for that mini bar. And I said, I don't think you know. how much I paid for this room. This is just, this room is insanely expensive for a college and a

college student. And, well, as we were checking out a couple days later, having hit the mini bar many times, and then they refill it, by the way, which also, Paul, is amazing. So I go down to checkout. This is before mobile checkout. And I'm waiting in this really long line. And I go up to the, finally, it's my turn in front of the woman. She goes, how did you enjoy your stay? I said, this was amazing. and she goes, did you enjoy the mini bar? And the inside Joe thinks to himself, what the hell business of yours is that? But I, you know, being polite, Joe, I said, well, I enjoyed it very much. Thank you.

And she takes this sheet of paper. She goes, okay, we've recorded the things you had the first two days. Just check everything that you had on this sheet of paper. Well, what she didn't know, Paula and what Cheryl didn't know, because I told her to go down early, was that I'm a frugal dude and knowing this refrigerator was full of food and we have this long drive back to East Lansing from Chicago. I backed my suitcase up to this refrigerator and took my left hand and clean that baby out and it's all sitting everything in that fridge is the tober lumbars like everything

is in my suitcase right next to me. And so I look at the woman and I look at my suitcase and I look back at the woman and I look back at my suitcase. And finally, the guy behind me goes, because he's been waiting forever too. And I look at the woman and she's like, is everything okay? And I go, I had all of it. And she goes, excuse me? And she was like very professional. Her mouth only turned up for just a second.

Like, are you freaking kidding me? Just for a second. And I go, yeah, I had all of it. So what's funny is I could be embarrassed by that. But you know what? There's a lot of people that grew up not getting the memo and not knowing. And hopefully that story helps a few people learn that that refrigerator is not free, Paula. That refrigerator is way more money.

And guess what? It didn't kill me, right? Right. So you're a lab rat. Be a lab rat. Yeah. Well, thank you, John, for the question. And I'm going to go so far as to applaud you for dedicating that cognitive space to other big,

important things. So in that regard, I would argue it wasn't a mistake at all. It was a reallocation of your attention. Well, and I want to applaud John, too, for having the bravery to call in and in front of the whole afford anything community talk about his mistake. Because that's the other thing we don't do, right? We just try to bury it and covered up. And I hope a lot of people also learn from John's mistake that will not kill him and will make him stronger.

Right. Well, speaking of regretting past decisions, our next caller, June, is frustrated by the fact that she triggered short-term capital gains when she made some moves in her taxable brokerage account last year. What can she do in the future? We'll discuss that next. Fifth Third Bank's commercial payments are fast and efficient, but they're not just fast and efficient. They're also powered by the latest in payments technology built to evolve with your business. Fifth Third Bank has the big bank muscle to handle payments for businesses of any size. But they also have the fintech hustle that got them named one of America's most innovative companies by Fortune magazine.

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Hi, Paula. With tax season coming up this year, I realized that in selling some of my taxable brokerage account, I realized some short-term capital gains and some wash sales. Primarily, I had long-term capital gains, but I was wondering if you had any advice for how to avoid and notice that you're doing a short-term capital gain or a wash sale, particularly using the Vanguard interface, which I'm sure many of your listeners also use. Thanks for all you do. June, thank you for the question.

So in terms of short-term capital gains, if you have held assets for less than a year, those are generally going to be taxed to short-term capital gains. If you rebalance annually, what I like to do is I like to go for one year plus one day. So just to be on the safe side, give it 366 days in order to make sure that you have held the stock for over a year. The extra day is probably unnecessary, but I like to just give it that little margin of error just out of an abundance of paranoia. So that's my approach to locking in long-term capital gains and avoiding short-term. Well, and I also just think, Paula, whenever I sell anything, if it's outside of a tax shelter, I just want to go back and do a quick look at when I bought it.

I want to look at what I paid for it. So I can do a calculation before I sell about approximately what my tax cost is going to be. And so because that's going to give me the date of purchase as well, then I can work backwards onto what the cost of this transaction is going to be. Right. And if you have an account with a lot of different assets that have all been purchased at different times, you want to check to see if it's FIFO or LIFO. FIFO means first in, first out. LIFO is last in first out. So basically think of it this way. With FIFO, let's say you've got Alvin, Theodore, right? You've got three different assets. We'll call them Alvin, Simon, and Theodore. You buy Alvin in October. So Alvin is the first in. You buy Simon in November. And then you buy Theodore in December. Wait a minute. We're buying chipmunks. Yeah, yeah. We're buying chipmunks. We're in the word chipmunks commodity traders. Big money. I use this analogy because Alvin, Simon, and Theodore always go in that order. Nobody ever says Simon, Theodore, and Alvin. It's never ordered like that. We know that the order of the chipmunks is always first Alvin, then Simon, then Theodore, in that order.

Theodore gets it every time. Right. And so Alvin is always the first. Theodore is always the last. So imagine that you bought Alvin in October. You bought Simon in November. You bought Theodore in December, right? Alvin is always. always the first one that you buy. Theodore's always the last. So if it's FIFO, you're selling Alvin first. And if it's LIFO, you're selling Theodore first. And when you're looking at the way the assets are sold out of an account, check to see if it's FIFO or LIFO so that you know, based on date of purchase, is this account, when you make that trade, are you going to be selling Alvin or are you going to be selling Theodore? That's what you want to find out. Well, I may think that way in my head, I would not explain that to the help people at Vanguard. I'm trying to sell Theodore.

Really, you want to sell Alvin. You want to sell Alvin. Right. You totally want to sell Alvin because Alvin is the one that you will have held for the longest period of time. And therefore, that's going to be most likely to be the long-term capital gain. Theodore is way more likely to be the short term. But using our lingo, June finds yourself on the Vanguard Blacklist.

people who they won't talk to. She gets a call from like Wildlife Rescue. Peter's on the phone. I will say this June is that all brokerage accounts have upsides and downsides. Vanguard is known for two things. The first one is they're incredible low pricing. And it's partly because of the way that that company is owned. when you're a shareholder, you actually own a piece of the company.

The bad thing about that, though, Vanguard is also known for maybe Paula, the clunkiest interface of all the major brokerage houses. And it's the thing that everybody bemoan. So if you don't have an account at Vanguard, just be ready. And I'm not saying don't have it at Vanguard. It is clearly something that you can use.

You can navigate around. But it's also not the most user-friendly thing. But I think also you shop at Aldi. You have to pay for the shop. cart. I think there's an analogy there. Well, technically, they give you the quarter back when you return the card at the end. I don't know about you. I always pay it forward at Aldi, though. I always hand my cart to the next person. Ah, tune, you asked about two things. You asked about both short-term capital gains as well as

wash sale rules. With the wash sale rule, you pretty much just don't want to buy the same thing within 30 days. So if you're planning on selling out of something and then buying back into it again, wait for 31 days. And that's not a tactical nature that we want to wait 31 days. My question is, when somebody's dealing with wash sale rules, what you're trying to do, I think far too often, Paula, is bet on something. You're betting something's going to go down, so you sell it, and then the thing either doesn't happen, or it does happen, right?

It goes down and you avoid the pain so that you go to buy it back, and then you end up with this wash sale. I'm just not a fan of that. The only time for me that from a strategic standpoint, wash sale rule actually comes into play is if it's the end of the year and you're walking through your portfolio, aka my analogy, I'm about to use, your garden, right? And you're weeding your garden, meaning you're looking at some of these ETFs that you bought and they're headed down.

So I want to make lemons for my lemonade. So what I do is I go. I go and I sell those things. And then after the beginning of the next year, I go buy them back. It's just so that I can create this taxable event. Now, if I do that within 30 days, I didn't do that because the wash sale rule applies. And the government goes, no, you really didn't sell that. You really still hold it.

So in that case, I get it. But in these other cases where I see wash sale rule apply, it drives me crazy. I actually know a professional that got caught up in this, Paula. they sold back early on in the pandemic. If you remember, the market took a sharp drop. And a lot of people thought, especially some pros, that this is the beginning of a doomsday scenario of a Black Swan. So it got to what ended up being the bottom and they sold.

And I know a story of one young professional who will remain nameless because I don't want to shame anybody that really. realized that for their clients. They sold it. They had what was called discretion in the client's accounts, meaning they could do whatever they thought was right. And then if you remember that sharp drop at the beginning of the pandemic in March, the market literally came right back and realizing this wasn't the end of the world, they bought everything back. All they did was they locked in a loss. And because it was a washed sale, the client couldn't even take advantage of that loss and of costing their clients.

just tons and tons and tons of money. Ooh. There's a story. See, John, you don't have a bad. That's bad. That's what I might ruminate over. Yeah. Especially doing that with somebody else's money.

Professionally. Ooh. Yes. Not a professional move at all. A, panicking when you're telling your clients not to panic, you panicked. And then you don't understand the wash sale rule. Yeah. Pretty amateur across the board.

Joe, have you seen? people accidentally trigger the wash sale rule because they think that they're rebalancing, but they, in an attempt to rebalance, end up buying a security that, unbeknownst to them, is so similar to what they thought they were buying, selling out of, that they end up really just trading one's security for a different security. Yeah. They think that they're diversifying, not realizing that the two securities are so similar that it triggers the wash sale rule because.

they've just traded an apple for another apple rather than an apple for an orange. So I'm going to tell you first that I am not a tax advisor. I'm not an accountant. I don't even play one on TV, not a CPA. So get tax advice from people that are in that area. But what you're talking about, Paula, is I sell SPY, which is the S&P 500, and I buy IVV. Yeah, exactly. Which is the I-Share's version of the S&P 500. Yeah. I've seen people do that and I have seen that not, not trigger the wash sale rule. And frankly, I think it should. And I think you probably think it should too.

Yeah. But I've seen people do that. And I think it's because the IRS truly hasn't paid attention that much. And again, I am not your tax advisor. This is not tax advice. I even said out loud, I think it probably should. But I've seen people do it and it didn't. So yeah, I haven't seen it.

I know exactly what you're talking about and I have not seen that happen. Wow. And maybe somebody else, maybe somebody in the Ford Anything community has seen it happen. I'd love to hear that, that story as well. Well, June, there are your answers. Don't try to time the market by selling in and out of the same security. If you are going to do so, wait for at least 31 days. And when you are annually rebalancing, wait for one year,

plus one day. Wait, and there's one more, Paula. Oh. Try to sell Alvin. Alvin. Exactly. Sell Alvin, hold Theodore. Alvin's like, damn it.

Well, thank you, June, for the question. Hello, Paula here. Okay, so this portion is actually being recorded later after our original conversation. I went down a rabbit hole. You know, earlier in the episode, Joe and I talked about mistakes that turned into unexpected wins. like corn flakes and oyster sauce and post-it notes. After we finished recording, I was like,

what other examples are there? I did a little digging, and here are three more examples where something unexpected led to innovation that changed the world. In the 1940s, Percy Spencer was an engineer working at Raytheon. He was building magnetrons, which are high-powered vacuum tubes,

used in radar technology. And this one day, while he was standing near an active radar set, he noticed that the candy bar in his pocket had melted. So he was like, huh, wonder what else would happen if I brought some more food around here? So he just started bringing food around. He brought in popcorn kernels, which popped. He brought an egg, which exploded.

After seeing all of this, he built a metal box that could contain and direct the microwaves, which allowed for controlled cooking. And he patented the idea in 1945. and two years later released the first commercial microwave oven. It cost $5,000, which adjusted for inflation is about $70,000 today. So he built a $70,000 microwave. But the whole discovery was an accident. He noticed something totally unexpected and then got curious about it.

And I think it speaks to, this is a theme we've been talking about on the podcast, follow your curiosity. Okay. on Velcro. So in 1941, a Swiss engineer named George de Mestral went on a hunting trip, and he noticed that these burrs from burdock plants were stuck to his pants and stuck to his dog's fur. You know when you go out in the woods and get covered in burrs? Most of us just like pick the burrs off and forget about it. Well, he decided to look at one under a microscope and And what he saw was a series of really tiny hooks that latch onto any fiber that has loops like dog fur or fabric, pants fabric.

And so he realized that he could replicate this mechanism and use it as a fastening system. So then he went to all these fabric manufacturers, and they all told him it's not going to work. They're like, look, making loops is simple, but creating really tiny durable hooks that could hold securely but still separate when needed. that's going to be tough. So he tried for years and finally found a manufacturer in France that was working with nylon blended with cotton. And he was able to use this material to handcraft these microscopic little hooks and attach it to a separate piece of cloth that had loops.

And so he patented it in 1955 and named it Velcro, which is a combination of the word velvet and the word crochet, which is French for hook. And so that, again, began as an accident, began sort of as an everyday annoyance that just sparked some curiosity. It sparked a peek under a microscope and a question of,

how could this be useful? Third and final story of an accident are Toll House cookies. The funny thing about Toll House cookies is that they're widely believed to be accidental, but that might not be the full story. So the widely told version of the story is that in 1938, Ruth Wakefield, who was the owner of the Toll House Inn, was making cookies and she ran out of Baker's Chocolate. And so supposedly she chopped up this Nestle semi-sweet chocolate bar and added it to the dough and she was expecting it to melt.

But it didn't melt and the chocolate held its shape and that created the chocolate chip cookie. But her biographer, Carolyn Wyman, disputes this telling. She says that's not what actually happened. So Wakefield was a very experienced and very meticulous baker, and she wasn't, according to Wyman, she wasn't actually out of ingredients. She was intentionally experimenting to try to create a cookie with a different texture. And so she wanted pieces of chocolate embedded into the dough rather than uniform chocolate. So whichever version of the story that you believe, what ultimately happened was that she,

She chopped up a semi-sweet chocolate bar that was gifted to her by Andrew Nestle. That turned into the Toll House cookie. The lesson is that often what looks like a mistake or what may be widely interpreted as a mistake is actually just a well-executed experiment. So, in keeping with the theme of happy little accidents, mistakes that turn into these unexpected wins, those are three stories with a bit of wisdom embedded in. All right, we're going to take a break. And when we return, we'll hear from Zerai, who's figuring out how to get small and mid-cap exposure in his 457 plan. Stay tuned. Our final question today comes from Zerai.

Hey, Paul and Joel. This is Zerai from Seattle. Thank you very much for all you do. And I've been listening to your podcast for, I think, three, four years. And I've found you through Paul Merriman's website. And I have been a very referring people to your podcast and appreciating your podcast and appreciating you're teaching and analysis of different questions. So I have a question for you here today.

My question is I have a 457 with my job, and we have limited mutual funds, and I am currently at 65% SNP-35 international, but they have two mid-cap funds that is available to us, and I was not sure which ones would be better. So the first one is the Fidelity Extended Market Index Fund, FSMAX, and the other one is the Wellington CIF2S Midcap Research Fund, which you can't really find a lot of information on the Wellington one, but the fee is a little bit higher for that versus the Fidelity Extended Market Index Fund. And I was just trying to add the midcap or small cap to my portfolio, and I wanted to

get your feedback on which one would be a better product. And any help you can provide, it would be greatly appreciated. And this is arrived from Seattle. Joe, I met you on the stacking Benjamin's meetup in Bellevue and appreciate all your assistance and looking forward to your answers. We had so much fun, Paula. I shared a few beers with Zerai and great to hear your voice again, my friend. Ah, that sounds like a lot of fun.

It was a dangerous place we held our meetup at. It was a place called Tapster, Paula, in downtown Bellevue right across the lake from Seattle. It was pour your own beer. Oh, that sounds great. I know. I have to trust my own ability to say no, which I have to say is not, when my, when my hotel is kiddie corner from Tapster was not that strong. Yeah. This from the guy who literally took his arm and grabbed everything in the mini fridge, everything from that, put it all in his suitcase. It turned out those beers weren't free either. Who knew? Actually, I did know that time. But Zerai has a. interesting question here, Paula, on a couple different fronts. So I, Zari, then went and looked up

these two funds. The number one place that I believe, Paula, you go to first at the same place, I go to Morningstar.com when I'm looking up any 401k, 403B, 457 funds. Zari, you're right on. The Fidelity Extended Market Index Fund is in Morningstar. Your Wellington CIP2 fund is not. I was able to find it. It turns out, Paula, that fund, not surprising to me, is actually a fun that Wellington has made for annuities. And a lot of small to medium-sized companies, 401K, 403B, 457 plans are annuity-based. Also, a lot of the time when a company, if it is a hospital or a municipality, they don't have a big, budget to run those things. So unfortunately, they pass the cost onto the participants.

So these annuity companies will run the fund for a very low cost for the provider and instead pass the fees on. So I will confirm that yes, Zerai, the Wellington Fund's fee structure is more expensive just by the type of beast that it is. It's not a true mutual fund. It's what's called a separate account. And the other thing I don't like about the Paula is because it's not a Morningstar, I can't track it. And you and I know you don't want to track your stuff all the time, but I want to have the freedom to whenever I want, be able to find up to the minute data. And there's so many funds out there like the Fidelity Extended Market that do that, that I don't want to choose a fund if I've got two choices that doesn't. So for that reason, I like the Fidelity Extended Market. But I'm going to question

this even more, Paula, which is, so Zerai right now has large companies and has international stocks, 7030. If I am broadening that out, what I would push back on is, why am I going mid-cap next? Why am I going mid-sized company? Because when I think about the points of diversification, mid-size squeezes up next to large-cap. And in fact, it's funny when you look at, you look at a lot of data, midcap and small cap, while the companies don't overlap, how they react in similar markets tend to overlap, much more than small and large wood. If I'm doing a third point on my triangle, I think I'd think long and hard about small cap versus midcap. Yeah, most of Paul Merriman's research really points to the value in having a mix of large

cap blend and small cap value. Yeah, those two really work well together over long periods of time. Yeah. I question that. But looking at the Fidelity Extended Market Index, Paula, do we want to take a second? Yeah. Div in a Morningstar on this. Yeah, absolutely. Yeah. Let's see it for people watching on YouTube if I can share my screen. Ooh. And even for people listening, I'll try to make sure that this is interactive. Now, when I go to this fund on Morning Star, the first thing people look at, Paula, is the fact that this is a three-star fund. On a scale of one to five, it's a three-star fund. This is what everybody looks at first. I'm not going to evaluate that yet. Having a growth mentality means, not how am I right, but what don't I know? I want to know why this is a three-star fund. Why does Morningstar

call this three stars on a scale of one to five? That gives me kind of a research goal of why it's there. So the first thing Zerai talked about was the expense ratio, and that's right on the front page take a look at this paula 0.03 percent very very very low cost fund so that makes me happy again not the first thing that i look at but definitely definitely there now what's funny is the category is mid cap blend but look at the investment style the investment style says small blend. Well, that's really interesting. So I'm going to come back to that. But the next thing is I, as I go through the tabs, there's tabs across the top of each Morning Star page for the fun that you're looking at. And as I go across these tabs, the tab that I click on first is performance. And this shows

me over long periods of time, over a 10-year period specifically, how this fund compared with other investments in its class and how it had compared versus the index. And the index for people watching is in red. The category is in yellow. This fund is in blue. So you'll find that the index outperformed everything over 10 years. This fund finished second. The average fund in its category finished behind it.

I also look at then quartile rank. Cortile rank is how did this fund perform versus its competitors? So we'll see in 2015 it was in the second quartile. So top 50%, top 50%, top 50%, top 50%, top 50%. top 50, top 50, top 25, top 75, so not a great year in 2021, 2021, 22, top 50, then top 25, top 25. So far this year, it's in the bottom. Well, that's interesting because what it shows me, as I look at the chart, we'll notice that

from 2019 until through 2020, it really did really, really well, but then it did much worse. So it actually outperform the index. And then it did much worse than the index in 2021. And then it's kind of come back during these good years in 2023 and 2024, but it still trails the index. So what that kind of tells me is I'm expecting this. It's almost like I'm a wine connoisseur looking at wines by smelling it, looking at the color.

I'm expecting the taste of this investment to be taking more risk than the, investments in its category take. And I also see that when it said small blends. So next I'm going to go over to risk. So I'm going back up to the tabs and I tab over to risk. And when I look at risk, I'm going to look first at this chart. Looks very much like the charts that we look at when we look at the efficient frontier, right? We've got total return on the left. We've got standard deviation, aka risk, on the right. And look at what's interesting. The red dot, paula, is the index, and blue is this particular fund. Very similar returns over a three-year period, and I can click up here at the top, I can click on five years. Very similar returns over five,

very similar returns over 10, but look at where it is risk-wise. So Zari, what this leads me to is this. I would think about small companies first, but what's funny is this, this is, this is, this. This is this is take so much more risk like a small company fund does that this fund is is closer to being on the on the small company meets mid company line than mid company meets large company line so if you don't have a small company fund available this might be a decent substitute because it's going to have more of those characteristics than it will the large company fund but it's also if you're looking for a mid company fund this is going to bounce around more. which is why, Paula, I believe they name this three stars.

If you're looking for a mid-company fund, five-star is going to be low-cost and act like a mid-company fund. This is going to be low-cost and act like a fund that's a small company fund. So that volatility is the reason that it's three stars. Yeah, 100%. Because you can get there, if you're looking for a mid-sized company fund, what this shows is, heck, let's not take the volatility of this fund. Let's buy the mid-cap index.

which is going to be a lot less volatile. Well, you make a great case for the fund. Just the fact that I can do that research, just the fact that I could look at that versus the Wellington Fund, my choice of the two. Beautiful. Well, thank you, Joe.

And I guess are we supposed to give a disclaimer here of this is not investment advice? It's purely educational. It's well, it's 100% educational. But you can see, and my goal is just education to show you what my funnel is. When I look at and how I look at it.

And notice, by the way, fee people, how little the fees were a part of my analysis. I just want to pour a little more salt in that. Attention to fees is necessary but not sufficient. It is. And there are many more things that we should be also considering. It's on the list, but it's not nearly as high on the list as a lot of people that I roll over make it. Right. Well, thank you, Zerai, for the question.

And thank you, Joe. for that walkthrough. That was incredible. Joe, where can people find you if they would like to hear more of you? You will find me and the Paula Pant, among other amazing characters at the Stacky Benjamin show every Monday, Wednesday, Friday. If you want to watch us and how we make the show live and watch Paula as she says amazing things for most of the episode and then crashes and burns on our trivia question. Yep.

You can also find us live every week. If you just subscribe to the channel and hit the button, it'll notify you when we're going live. Usually it's Wednesday afternoons, but you can watch us make the show, which is also pretty fun. Yeah, I constantly come in last place in that trivia contest. It actually defies a statistical probability. Totally does. Right? Because, I mean, if we were randomly guessing, I would get it right one third of the time.

But no, I consistently get it wrong. Three out of three times. It is incredible how consistent you are. Yeah, there is no reversion to the mean. None. Someday, Paula. We can all dream. Well, thanks to all of you for tuning in.

If you enjoyed today's episode, please share it with your friends, your family, your coworkers, your neighbors, share it with the people in your life. Also, subscribe to our newsletter at afford anything.com slash newsletter. and if you want to talk to the community about how to make melons out of melanade, you can do so at affordanything.com slash community. Thanks again for being an afforder. This is the Afford Anything podcast. I'm Paula Pants.

I'm Joe Salcci-Hi. And we'll meet you in the next episode.