Preview:

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money.

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More About This Episode:

Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. Ryan unpacks the financial “pranks” people may fall for—from too-good-to-be-true returns to myths about Social Security, taxes, and healthcare in retirement.

Through stories, examples, and a few laughs, we’ll break down why these beliefs are so tempting—and how they can quietly derail your long-term goals. You’ll also hear why obsessing over dividends, blindly trusting the 4% rule, or assuming you’ll “just keep working” can be risky habits if left unchallenged. This episode is a sharp reminder to stay curious, question assumptions, and always plan with eyes wide open.

Here’s what we cover in this episode:

💸 Healthcare costs are no joke in retirement

📉 How taxes fool more people than they realize

🧠 Why “guaranteed returns” are a red flag

🪙 Dividend chasing can backfire

0:00 – Intro

2:08 – Frontier’s New Standing Room Only Policy

4:06 – Guaranteed High Returns

6:05 – Social Security Scams

9:16 – Tax Time Bomb

10:32 – Medicare Myths

11:07 – 4% Rule

12:21 – Dividend Paying Stocks

13:24 – Penny Pinching: Pro or Con?

15:56 – Returning to Work

17:17 – F.I.R.E


Resources:

Retire Pilots – https://retirepilots.com

Get your FREE Retirement Toolkit – https://bit.ly/3ZmZsaX

Pilot Tax – https://pilot-tax.com/

The Pilot’s Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Connect with Pilot-Tax: https://pilot-tax.com/

Episode Transcription:

(Note, this is an automated transcription. Please forgive any errors.)

Walter Storholt 

Well, we had April Fools get a couple of us recently. Maybe you avoided any of the major pranks on that day, but it got us thinking a little bit about some of the beliefs that are out there that fool retirement planners and savers the most so on. Today’s episode, we’re gonna break down some of those top areas, some of those top beliefs that get people in trouble, why they fool folks, and how you can avoid being fooled in the financial world. We’ll dive into that with Ryan Fleming coming up next, another episode of the pilots advisor. I’m Walter Storholt alongside Ryan Fleming the pilots advisor. It’s great to always have him here. And Ryan, did you pull any pranks on anybody this year or have a prank pool pulled on you at all talking about April Fool’s Day, yeah, for April Fool’s earlier this month? Yeah. Well,

Ryan Fleming 

what do I remember about April Fool’s Day? I can’t remember any pranks. I didn’t pull any pranks on anyone, but there was something that happened that I’ll comment on. Okay, so on April Fool’s Day, the Clemson athletics decided to release the fact that they are going to start selling alcohol at all these sporting events. So it was like the worst marketing effort ever, because half the people thought it was an April Fool’s joke. They’re like, Is this for real? Are we? Is this actually going to be a thing? And and then they finally had to come back out, like the next day, and say, this was not an April Fool’s joke, where this is really happening, and it’s going to happen this weekend and and so I think a lot of people are around here are getting excited because, you know, some of the sporting events might be a little bit more fun, and it’s, it has been a dry campus this whole time, gotcha. But, yeah, I thought that was pretty hilarious. Marketing to put that out on April Fools, and everybody just was in Yeah, uproar, thinking it was a joke. Clemson

Walter Storholt 

fans are already pretty, pretty rowdy, and so that’ll that’s only going to add a little something to the mix there for the Tigers. I think, I

Ryan Fleming 

think so too. And I think that people, rather than leaving at halftime to go back out to their tailgate, will probably stay in the stadium now, and it’ll probably be a little bit more raucous and loud into the third and fourth quarter, even when it’s not a close game. Well,

Walter Storholt 

I actually got fooled a little bit this year, and it was as actually related to the pilot world, to the airline industry. So I don’t know if you saw this one, Ryan, it got me because I technically didn’t get fooled until April 2. You know how your you know how your phone recommends articles to you? Well, I’ve noticed now, over the last couple of years, that it’s not April 1 that you get fooled. It’s the second or third day after April Fools, when the articles from April 1 are starting to filter through to your recommendations, but you’re no longer on guard, because it’s no longer April 1 interesting. So this is what got me. Was the frontier article, or the prank about Frontier Airlines offering standing room only flights for $9 on their on their airline. That one got me because I was like, I could totally believe that for a frontier with, you know, all the like, little tiny things and add ons and ways to save money and at a discount airline. And I was like, I would do a $9 flight and hang on. I think it started to get a little unbelievable. I mean, it was pretty unbelievable to begin with, but, you know, it caught me in a weak moment, I guess. But I actually thought it was pretty awesome, because I was like, Well, how are they going to safely do that? And they said in the article they were going to use, like, you know, when you go to the amusement park and they have the standing rides, but they drop down the like, the shoulder harnesses that kind of your arms go over the shoulder harness, that kind of thing. And then there’s a little thing kind of in between your legs that you’re sort of sitting on, but still standing. I was like, Oh, now I could totally see that that would keep you safe, right? And strapped in, in a way, but then let you just stand up. But anyway, it was just believable enough to be like, I could see them doing something crazy, like this. Well,

Ryan Fleming 

there’s so much misinformation out there, and there’s so many articles now where it’s just a total joke, but you read it and you’re just going, you know, you catch yourself sometimes going, oh, yeah, this one’s definitely a joke, but, yeah, but we’re in such a crazy world nowadays that some of it’s believable. So let’s

Walter Storholt 

look at some of the beliefs that fool retirement savers. Unfortunately, Ryan, it’s not just kind of that one day of the year that gets retirement folks. It’s we can be susceptible to being fooled any day of the year. And so we got to be on guard a little bit. So I got a list here. We’ll run through some of these to see why these are fooling folks guaranteed high returns. And if you see some some belief or some marketing that it can be easily attained, it you know, it might sound too good to be true, like that, some of those articles and some of those things that have gotten us in the past, but people still fall for this all the time, don’t they? Well

Ryan Fleming 

and guaranteed is not even a word you can use in the investment world from a compliance standpoint, because there is no guarantee anytime you invest in the market. I mean, it’s risk. I think because of we’re in that day and age, we have a lot of these tech stocks that have got these amazing, crazy returns, or if you look at what Apple’s done over the long term. Or the mag seven, even holding up the s, p, I think people have a very warped vision of what investing looks like now, and what and what good return should be. I mean, historically, if you can get 8% return, eight to 10% return over an equity position, over the long term, you’re you’re killing it. You’re doing a great job. And I think that that uh, people probably don’t see it that way anymore, and, and there’s definitely no guarantees in this world, and that’s why you have to lower your risk by being diversified.

Walter Storholt 

Yeah, that’s a big one. I I start to think scam when I see guaranteed that, just like just I found it safe to immediately make that association, and then I have to approve it otherwise, right? Started there.

Ryan Fleming 

Pilots have all these crazy, crazy ideas, and it happens all the time. And I don’t know how many times they’ve come with me, like, all this, that or whatever, and I go, Well, it sounds to me like it’s too good to be true. And, you know, it might take a year or two, and then they come back and go, Yeah, I got scammed, and I lost all my money. And, I mean, it’s, it’s happened multiple times. So any guarantees, you know, or there’s no free lunches? I mean, that’s true. We

Walter Storholt 

could do a whole show about where people get fooled about social security stuff, but let’s just throw one of these in there, one of these sort of Social Security myths, and that it’s you better claim it as soon as possible, before it runs out. And I think that leads a lot of people to making kind of knee jerk decisions when they hit retirement. It’s

Ryan Fleming 

amazing how much social security conversations have changed. You know, it used to be, Hey, when are you going to die? Of course, nobody knows when they’re going to die, but if we can make an estimate on that, then we can just run the numbers and figure out when’s the best time for you to take Social Security nowadays, where, you know, people are scared that it’s going to go away or and I think more realistically, Social Security is not going to go away. It’s going to be reduced at some point, just because it’s unsustainable where we’re at right now, you know. And maybe that might all change with Doge and what’s going on now, but I think the reality is it’s going to get reduced and or unfortunately, it may get means tested one day. But because of all those things, the narrative on Social Security has totally changed. Yeah, I see a lot of people now taking it earlier just to get it or hoping that they’ll get grandfathered in before it gets reduced. You know, there’s a lot of justifications for for actions, but I think it’s an individual thing. But yeah, Social Security alone may be a myth at this point. I don’t even know what to think anymore, but we’ll see what the future holds. It

Walter Storholt 

definitely seems like a death by 1000 cuts sort of thing, versus it just disappearing overnight one day, like it’s just gonna get slowly eroded away. And I guess that’s better than just disappearing overnight. But well,

Ryan Fleming 

here’s here’s the reality of it. Though, all of us has paid into Social Security all these years. But how about this idea Social Security is supposed to be there for us to help us out in retirement, maybe just like a 401 k plan. The government still takes all your social security where it’s forcing you to save, but that’s your 401 K plans. You almost have your own social security bucket. How about that? Yeah, yeah. I think that’d be amazing, right? Because then, you know, hey, I paid into Social Security all these years. The government forced me to do it, but that’s actually my money, and I will get it back one day.

Walter Storholt 

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Ryan Fleming 

I think that they just don’t understand the problem. And I think that they don’t understand what’s going to happen to them later on. I think that this goes down the same path of kick the can down the street, and I won’t worry about the problem and the big, the big difference with pilots versus any other profession out there, because all these airlines lost their pensions. Almost all the major legacy carriers are dumping 18, 19% of whatever you make into your 401, K, which is a great thing, but it’s all tax deferred money. And you see a lot of people, Hey, I don’t want to pay. Tax on any of this money, and they keep dumping more and more money into these tax deferred or traditional 401, KS, not having any clue how big the tax problem is going to be later, because that money is going to grow all these years, and you have this massive amount of money, but it’s not yours. You’re still in a partnership with the US government. You’re going to get destroyed when RMDs come around. And it’s amazing to me that most investors out there are completely, completely oblivious to this until it’s too late. I

Walter Storholt 

know healthcare is where people get fooled in retirement, specifically about Medicare, and they misunderstand it a little bit, and they kind of think, Oh, it’s just going to make the process really easy. It covers everything once I can get Medicare. Life just kind of takes care of itself. From that standpoint. Where are people misguided on that

Ryan Fleming 

well? And the worst part about that is once you find out it’s almost too late, and then you start seeing it eating away at your retirement savings. And I would put that as one of those other myths that people just don’t think about, they don’t think about taxes, they don’t think about inflation, and they don’t think about health care, all three of those can blow up your retirement portfolio. Yeah.

Walter Storholt 

What about the 4% rule? Is that a belief that fools people today, or is that still kind of a good starting point for retirement savers to kind of use as a rule of thumb in the retirement world? What’s your opinion on that? I look

Ryan Fleming 

at it as like a big fat crayon number, you know, like, hey, it’s a WAG to see, you know, what you’re looking at. No different than, you know, they have all those percentages out there of how much you have to save, of your actual, you know, annual income, and then your, that’s your number for retirement. I think that you got to get much more detailed into that when you start looking at true Retirement Planning. But it’s a good, good number to start with, per se,

Walter Storholt 

okay? But it’s a very, like, very high level understanding number, not something that you’re then going to really utilize going forward. It’s it’s just, hey, here’s where we begin. It got you asking the right questions. It got you thinking the right way. But now let’s get more sophisticated quite quickly. Is what you’re 100%

Ryan Fleming 

and then on top of that, it changes. You got to constantly reanalyze because depending on what’s going on in the market or your spending habits, you got to constantly reanalyze that based off of what’s going on, whether it’s inflation, taxes, the market, yeah, I mean, it’s, it’s very gray area, for sure, as we

Walter Storholt 

talk about people getting fooled. Do you see those who ever Chase or obsess over dividend paying stocks? Maybe that’s the way to save for retirement that they’ve been kind of taught over the years, and so that becomes their obsession.

Ryan Fleming 

I can’t stand having conversations about dividend paying stocks. It’s like one of my pet peeves. Because number one. If you’re if you have it in a taxable account, all it’s doing is giving you more taxable income that you don’t want. Okay, so I see that all the time, and I don’t really care if I’m making money via the dividend or because you’re keeping those, ultimately keeping those dividends inside the stock price, and you’re getting better returns without having a dividend. You know, it’s all one in the same to me. But I people talk about dividends all the time. And I don’t know if there’s mass marketing out there to get people to be so interested in dividend paying stock, but it’s an interesting conversation. We’ll say,

Walter Storholt 

you’re saying there’s better ways out there to structure a portfolio and a plan. We certainly shouldn’t be obsessing or chasing those absolutely not okay. What about the fear of spending? Just to take things from a little bit of a different angle, here, we’re talking about, again, things in general that could fool retirement savers the most is there a time when frugality is no longer a virtue. We were kind of talking about our frugality of flying and sometimes how that frugality doesn’t make a whole lot of sense. I’m

Ryan Fleming 

going to answer this one a little bit carefully, because I think the far majority of pilots, Americans out there aren’t saving nearly enough, and they have no clue how much they have to save for retirement. But yeah, there’s a case where frugality becomes a problem. I think some good examples of that would be my mother right now. They have, you know, her husband has a pension. They have plenty of money, but she’s, she grew up on a farm, and they had no money, so she still, you know, scrolls it all away, and they won’t spend anything and, and I’m like, Mom, you guys are are doing fine. Like, go get the driveway fixed, go buy a TV. Like they wouldn’t buy a TV. They’re waiting on this TV to die before they were going to go buy a TV. And I’m telling you, it was like, maybe 1010, to 12 inches. I mean, this tiny little TV, and I’ll be over there,

Walter Storholt 

like, like, like, there’s, there’s bigger tablets out there than,

Ryan Fleming 

you know, they’re complaining about not being able to see it. And I’m like, I can’t see it. Like, what are you guys doing? And then, you know, it was like, well, we’ll, we’ll get, we’ll get a new TV. When this, one dies. Well, guess what? TVS don’t die anymore. I mean, this is not really a thing. Yeah, so I went to Walmart and I brought home, I brought home a 60 inch TV. I’m sorry you guys aren’t gonna live that long.

Walter Storholt 

They’re like, you’re like, now you can see, okay, great. I was gonna say either that or when they’re not looking, you need to go drop that TV on the ground and break it

Ryan Fleming 

  1. My father in law, you know, he’s got a couple pensions. He was a DEA agent. He’s 80 some years old, and I’m like, talking to him about, like, Randy, I get, you know, passing on a legacy to your grandchildren, what have you. But let’s start looking. I have him read it, read this book called die with zero, because it’s time to start spending this money, you know, like, go, go, do something that’s going to make you happy. Yeah.

Walter Storholt 

Uh, that’s, it’s neat. It’s probably a neat thing, though, when you’ve got to tell people to get more comfortable with spending versus the other conversation, right? It’s a little tougher when somebody is over spending and you got to reel them back in,

Ryan Fleming 

or they’re in retirement and they realize they’re going to run out of money, or their lifestyle is going to have to be way cut down from what they’ve been doing for the past 30 years. Yeah,

Walter Storholt 

so at least those are kind of fun problems to solve when somebody’s kind of that little bit of that penny pincher, and you’re trying to just get them to free up a little bit. So it’s still an issue. But can that’s

Ryan Fleming 

a money conversation when they don’t have a money problem, versus, hey, we got a problem well,

Walter Storholt 

and that’s that other issue that fools retirement savers. Some people are okay with that idea of, you know what? I’ll just keep working. Right? Either, if I don’t have enough money saved retirement, I’ll just keep working as late as I can, or if I start to run out, I’ll go back to work. But a lot of people don’t realize that that’s a that’s a big issue, and a lot easier said than done. Do you

Ryan Fleming 

realize how miserable that would be? And let me paint a picture for you, because I see it happening to people in the future where, hey, I’m an airline pilot. I make $300,000 a year. My family’s used to this $300,000 a year lifestyle. I haven’t saved enough money. Boom, I’m 65 Guess what? I’m done flying. And yeah, you’re going to have to keep working. But what are you going to do? You’re not going to have a job that is going to pay nearly as much than what you’re used to. I mean, you’re going to be working at the Home Depot per hour because you have to, yeah, and I think it’s sad. I think it’s sad because you could do a little bit of math and see what’s going to happen to some of these individuals, and guess what? It’s not going to cut it. And I think the kick the can down the road mentality, I’ll be okay. I’ll keep working. Well, the last thing I would want to do is when I’m in my late 60s and I’m doing something that’s, you know, on my feet, non stop, or much harder job than I was used to making pennies on the dollar.

Walter Storholt 

You’ve heard of the the fire movement is kind of big among my generation, and folks even younger than me, and the idea where you want to retire at 40, and I’m like, What are you going to do?

Ryan Fleming 

Oh, yeah. I mean, like, what are you going to take your time up? I don’t get that at all either,

Walter Storholt 

but it’s not so much that too, is that, just like, you know you’re going to retire at 40 and then you’re going to be, in two or three years, needing to get back into the workforce, and I feel like that break is going to hurt a lot of people if they truly try to do something like that. So

Ryan Fleming 

just because you got one last one to do. But I’m I we’ve had so much fun on this podcast, but I have a meeting that I got to get on right now, 1030 well,

Walter Storholt 

we’ll leave people hanging and say there’s another one that fools people. But in order to find it out, you got to get Brian’s retirement toolkit and then come in for an appointment. How about that, Ryan? We’ll turn it into a call. Now

Ryan Fleming 

we’ll do it. It’s the best one. It’s the best myth that we’re going to talk about. If

Walter Storholt 

you really need to know it, then you got to go get the toolkit. There you go, where we’re being a little tongue in cheek with a call to action there. But in all seriousness, go pick up the toolkit. Ryan has put this together. It’s for pilots. It’s where everybody starts. They go and check out the toolkit. Ryan’s gonna disappear. I’ll finish the show, Ryan, go for it. Can you finish the show up for me? You got it? Yeah, this is good. This will be a fun finish. So bye, Ryan. We’ll see you later. Everybody go to retirepilots.com check it out and get the toolkit. And you can make sure that you are on your way to and through retirement. It’s packed with Ryan’s books and other great material as well. It’s all at retirepilots.com that’s retirepilots.com We’ve got it linked in the description for Ryan. I’m Walter. We’ll see you next time on the pilots advisor.

Speaker 1 

Information is for illustrative purposes only and does not constitute tax investment or legal advice. Always consult with a qualified investment legal or tax professional before taking any action.