Preview of what we’ll cover today:

☃️ Snow Day Perspective: Why unexpected pauses reveal how prepared you really are

🛷 Delayed Gratification: How patience and discipline pay off over time

🌨️ Financial Storms: Staying steady when conditions turn volatile

🧥 Layers of Protection: Building resilience through diversification

🏔️ Freedom & Flexibility: Enjoying the payoff after years of preparation

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More About This Episode:

There’s something magical about a snow day. They slow everything down, and that’s exactly why they make such a powerful metaphor for money. Unexpected pauses, changing conditions, and the temptation to react emotionally all show up in both weather and finances. Ryan connects familiar winter moments to smarter long-term thinking, reminding us why preparation matters before the storm hits. Sometimes the best move isn’t doing more, it’s knowing when to stay put and let your plan work.

Go Deeper Into The Episode:

0:00 – Intro

1:31 – Memorable Snow Days

3:48 – Lesson #1: Sledding Down the Big Hill

6:16 – Lesson #2: Rolling the Snowman

10:39 – Lesson #3: Stay Put To Stay Safe

14:35 – Lesson #4: Dressing In Layers

19:50 – Lesson #5: Enjoying Snow Days and Financial Freedom

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  00:00

There’s something special about a snow day, and many across the country have certainly had a few of those recently, as we’re recording today in the heart of winter. And there are somewhat unexpected, maybe some memorable and maybe some routine things about a snow day, and it might bring back some nostalgia for all of us as well. What we’re going to do is borrow some of those classic snow day moments and help teach you a little bit about the financial world along the way. It’s financial lessons from a snow day a great combination. Let me throw a snowball at Ryan and get him in here, and we’ll get started. Welcome to another edition of the pilot’s advisor. Ryan heads up, Snowball coming your way, my friend, if

Ryan Fleming  00:43

anybody was wondering, Walter, missed me by like a mile. Did you play baseball growing up? What happened?

Walter Storholt  00:50

Man, yes, yes, I was a great fielder. Absolutely. I was a great thrower. Batting, not so much, although you’re right. I threw the snowball straight and we’re side by side on the screen. So it just went

Ryan Fleming  01:01

right through the screen. I was ready to juke, and then it was like, I need to throw it,

Walter Storholt  01:06

throw it this way. Or I don’t know if I’m going to be on, which side you’re going to be on, maybe that way.

Ryan Fleming  01:10

So I don’t know when people are going to listen to this, but we’ve just had that huge cold front that went across the country and affected everything. I’m in South Carolina, and we had snow and ice, and we’re about to get hit again.

Walter Storholt  01:22

Yeah, yeah, back to back storms, and I’ve seen some stuff that next week, Ryan, there may be even another little thing on the way. So it’s one of those three in a row kind of things.

Ryan Fleming  01:31

I grew up in Ohio and I live in South Carolina. To get away from this. I’m not into this, so I thought it would be good for us to do this, this snow day thing, but man, this is horrible. And you’re I’m gonna go ahead and throw on that here for today’s episode. Try I can stay warm and get through this.

Walter Storholt  01:50

Love it. All right, we’ve got the pilot’s advisor hat. We’ve got the Air Force snow beanie. We are ready to go for today’s show. I think I’ve got lots of great memories, Ryan, growing up. Now, you were talking about Ohio. I grew up in North Carolina, so not a ton of snows, but when they hit they’re usually pretty good snows, and so we I’ve got some great memories of those. You know, big snows. Back in the day, sledding down the big hill was obviously my favorite thing to do when the big snows happened. We lived across the street from a country park, we or county park. We’d go over to the county park and grating Hills all throughout the park. It was just absolutely, absolutely the best. So sledding was probably my highlight of any big snow day. I don’t know about you.

Ryan Fleming  02:33

Well, the big difference was with you, growing up in North Carolina, if it snowed at all, you guys had school off because you got that’s true. Didn’t know how to handle it. It’s like, oh yeah, white stuff, everybody,

Walter Storholt  02:42

if it snowed on Sunday, we weren’t going back to school until Friday. Yeah, that’s kind of

Ryan Fleming  02:46

what I’m dealing with right now. I mean, my kids haven’t been at school all week. It was like, Monday’s canceled. Tuesdays cancel. Wednesday’s canceled then. But anyway, at least in Ohio, we saw a lot more snow. I mean, the weather was, you know, winter was winter then, yeah. But yeah, absolutely. I mean, with if you get school off, everybody’s out, playing, sledding, building snowman. I mean, it wasn’t just just sleeping in. You were out, yeah, having a party.

Walter Storholt  03:12

I guess all the you know, homeschooling, like schooling from home, or the remote schooling, kind of ruined some snow days for some folks. You know, now there’s not that true snow day. They kind of load you up with work or what have you seen?

Ryan Fleming  03:24

You know, they call it an E learning day. I don’t know about your kid. You know, you have a little, tiny boy that’s not going to school yet, yeah, not yet. We’re not there yet. But they have these e learning days, like, you know, online learning. No, it’s not a thing, yeah.

Walter Storholt  03:39

Okay, gotcha. So color, color, with some pens and pencils, and then go play for the day.

Ryan Fleming  03:44

Gotcha acting like we’re actually having a school day, but we’re really not. Yeah.

Walter Storholt  03:48

All right. Well, on to the financial lessons, then sledding down the big hill. First thing I think about going down the best part, but Ryan, sometimes coming back up that big hill is the hard part. You know, it’s nice and smooth going down. It’s worth the effort for the struggle to climb back up each time, but you might be slipping and falling and then backtracking a couple of feet. It’s not like when my mom grew up and she tells stories about the neighborhood snowmobile who would take all the kids and ride them back up to the top, and they got to run down that hill many, many, many times. You know, if you’re on your own two feet, you might only have a couple of good sleds in you before you’re starting to wear out a little bit. But I got to imagine there’s a good financial connection somewhere in there.

Ryan Fleming  04:27

Yeah, I can definitely connect that. I mean, I, you know, my own personal experience, I feel like you got to put in the work to get results right. And I think that we’re able to look at that a lot with sports. You weren’t just going to be good. You had to put in the work. You had to go to the gym, you had to work for it. And I think that it’s healthy to work for something to get that gratification later. I think charging up that that hill is going to allow you to have a great retirement later, and that, or, you know, having the assets or the money to go go out to dinner and go. On nice vacations. And I think unfortunately, we have a little bit of a generation, you know that instant gratification, give it, just give me what the good stuff? Yeah, not, not any of the pain is a little bit of a problem with with the new generation, which makes it tough. Because I don’t think saving and investing is a hard thing. I think it’s pretty exciting, but you got to put in the work, meaning you actually got to let your money work for you, yeah? And I know, I know spending is fun too, but compounding interest is really cool, yeah.

Walter Storholt  05:29

Now great points, and easy to see the connection there with sledding down the hill, that that’s retirement, right? We work hard throughout our working years to then enjoy that retirement and see all that hard work pay off so well.

Ryan Fleming  05:40

And I kind of look at it like the work week. I mean, I don’t, you know, they call it work for a reason. I don’t, I don’t love working all week, but then at the weekends, right? Then you get the weekend. And how much better are the weekends if you worked your butt off all week long? And then maybe you could spend a little bit more money because you worked hard. You work hard, play hard, right?

Walter Storholt  05:56

Yeah, yeah. Maybe sledding is the, the ultimate microcosm of work hard, play hard, right? Work hard, getting up the hill and then enjoy it on the quick way down. That’s pretty about the same proportion of work to weekend time as well. You know, kind of a little bit longer on the work side going up, but in a little bit quicker on the way down. But fun nonetheless. What about rolling a snowman? Was that something you got into, or building a snowman, something you got into when you were a kid.

Ryan Fleming  06:21

Do you remember those days when you had just the perfect sticky snow, yeah, where you were, like, rolling a snowball, and it wasn’t just the snowball, like, it was almost like you’re rolling a rug, yeah, you know where it was rolling, like, outside of where you were rolling, because it was so sticky, yes? And it would just get great description, you’re absolutely right. Yeah, it was almost like you’re rolling a rug, because it got big. Because it got bigger and bigger, almost harder to roll the ball because it’s so sticky. Yeah, yeah. And you had, you’d have to almost reshape the ball because it was actually getting into like a square.

Walter Storholt  06:52

Yeah, those are good snows out here in Colorado. Now, Ryan, you know, we just get the we just get the dry powder, so it’s real hard to make snowmen out here. Yeah? Well, it

Ryan Fleming  07:00

just depends on what you get. Sometimes you get that nasty slush, you know, I went to school out there. Yeah, I know it very well. I know it very well. As a matter of fact, I might be seeing you a lot more. I think my daughter’s number one choice is still the Air Force Academy. Oh, very cool. You know, we’ll find out probably here in the next year or so, but it’s updated on that. That’s very cool. Yeah, she just took a visit to the Citadel, Charleston’s not far from us. Nice, and the Citadel has been recruiting her for soccer, so we just did that, which was cool, but, but, yeah, I still think, you know, she’s got the Air Force in her so,

Walter Storholt  07:32

very cool. Unfortunately,

Ryan Fleming  07:34

back to the snowball, back to the snowball. I think that this is an awesome metaphor. Yeah, you’re about to talk about,

Walter Storholt  07:43

oh, I’m pretty sure, I mean, it’s your favorite thing. You already hinted at. It, power

Ryan Fleming  07:49

of compounding interest, and it’s so hard to see it. I mean, it’s, it’s a, what I like to tell my clients is, you know, like, let’s say you made 10% on your money. Well, if you only have $100 it’s not very exciting. You made 10 bucks, you know, and that, but the compounding effect of that is now you have 110 right? Yeah. But even then, if you have a little, tiny snowball that does, that doesn’t that, that’s not exciting. But think about if you have a million dollars, saved 10% of a millions, $100,000 that you get for doing nothing in one year, because you put in the hard work and built that snowman, you know? So now you got to hunt $1,100,000 and then it compounds. So what happens is, it takes a long time to get to a million dollars, but 2 million comes really fast, really fast. And then guess what, 4 million pops on there. And so it gets more and more exciting, the bigger your snowball is. But you got to put in that early work, you got to climb that hill, you got to push that snowball and get it bigger. But once, once you get that bigger snowball, you see the power of compounding interest, which is just amazing. And I think it’s, I just don’t think you you see it early in life, you start seeing it later in life, and it makes you even go, Man, I wish I would have saved more in my 20s. Yeah, absolutely, just me, at least, wasn’t it Albert Einstein that had some comment about compounding interest being the eighth

Walter Storholt  09:13

wonder of the world, yeah, yeah. Believe that quotes credited to him, absolutely.

Ryan Fleming  09:17

And I mean it truly, once you see that compounding of a larger entity later on, it’s mind blowing. I love it. I love it. It gets me excited. Investment. I don’t know

Walter Storholt  09:29

if the next one will relate to compounding, but before we turn the page to that one, if you are wanting to plan a little bit better for your financial future, to discover that power of compounding, or if you have been discovering that power over your working years, but now you’re starting to wonder, as you get closer to retirement, what do I do? How do I reverse this now and pay myself out? What’s the best way to do that? How do I withdraw what? What is the right way to go about this whole retirement thing? Well, that’s where Ryan really specializes in helping pilots get to retirement, of course. But then those first couple. Years after it, and then all the way through it, that long term view, making sure that you are making the right decisions. If you’d like to talk with Ryan a little bit more about your particular situation, very easy to do that. All you have to do is click the link in the description of today’s show that’ll take you to where you can order the retirement toolkit, specifically built for pilots with Ryan’s books, some great resources and more information again, all you have to do is click the link in the description get that toolkit. It’ll also qualify you for a free portfolio analysis one on one with Ryan and the team, where they’ll be able to then really dive under the hood and take a look at what’s going on with your finances and have that conversation with you about your goals and how to accomplish them. So check that out. All right, Ryan, this next thing might be hard for you and I to do. I know it’s hard for me to do, and you just strike me as the kind of guy that likes getting in the car and going out in the elements to explore a little bit, but the common wisdom is probably to stay put and you stay safe, especially if the roads are pretty icy. Even the best drivers have trouble controlling their cars and their vehicles. You know, in snow and especially icy conditions. I gotta imagine that financial storms is the connection here, right? And it’s trying to stay safe in the storm.

Ryan Fleming  11:09

Yeah, we can make that connection. I think I’ve gotten better at this as I’ve gotten older. You know, where I think I agree that I used to want to go out there and play and see what’s going on, and see how many trees are down,

Walter Storholt  11:19

and see if I can do some donuts in the parking lot. Oh, yeah,

Ryan Fleming  11:22

watch my car slide a little bit. That was always kind of fun. Yeah, but I’ve gotten better at this as I’ve gotten older, and when I think about investing, it’s investors want to do something at the worst possible time. You know, we know market volatility is going to be out there. It’s just a matter of when it’s coming and the market has a correction or a 10% pullback, and investors panic, you know, at that point in time, they feel like they have to do something, and it’s that whole short term emotional decision where you do the exact wrong thing, when you just need to stay put and not do anything. Or I like to use the analogy that you know, if you’re flying an airplane and you hit turbulence, you don’t just jump out the window. You got to ride it out, right? It’s there. You got to ride it out. So just, just hang on. And those that do that and have that discipline and ride out the storm and stay safe, they get those long term returns that a portfolio is going to go that’s going to realize for you that it’s engineered to handle that that volatility, or those snow days, or that, you know, that ice storm, or what have you. But unfortunately, you know investors are their worst enemy, and they tend to want to do something at the exact wrong time. And I think that snowstorm would be it. Hey, you know, running outside, not having any food or water.

Walter Storholt  12:44

Yeah, that’s the problem. People go out in the storm without any tools to help them if they get into some trouble. I try to always go out with chains for the tires, always in the back of the truck, and we’ve got warm blankets. Always bring in extra bottles of water and food and flashlights and additional gloves and jackets and all the stuff and shovel just in case I need to get out of a jam. But a lot of people don’t have those things when they go out in those storms, and that’s where you’re calling emergency services and get in trouble.

Ryan Fleming  13:10

Well, that’s a great analogy too. Is just having enough diversification in a portfolio, so regardless of what’s going on in certain asset classes or even certain countries, you’re still good because you’re having your money spread out, yeah, 30,000 unique positions, 40 some countries. Well, guess what? It doesn’t matter what’s going on with us large cap stocks here. I think that happened last year. I mean, you know us, stocks weren’t doing very well. So if you’re all in us, large cap, all in the s, p, you weren’t very happy. But if you had a portfolio that was diversified. I mean, international stocks did great last year. So anyway, if you are going to go out in the storm, make sure you’re prepared and make sure you’re diversified, and you have all the stuff that Walter has in the back of his truck, there you go,

Walter Storholt  13:56

absolutely, yeah, prepare like it’s the end of the world, right? The Apocalypse truck is what we’re prep.

Ryan Fleming  14:01

You’re in Colorado, and you have to do that because the weather changes every 10 minutes. Yeah. And I used to hate watching on TV where, you know, Susie and Joey, or whoever it was, went out hiking, and, yes, you know, they were stuck out. They didn’t have any water, they didn’t have any clothes, you know, for the, you know, the storm that just came in, yeah. And you have to be careful with it out there hiking on the front range.

Walter Storholt  14:23

You get surprised, and it starts snowing and hailing on you, and temperature drops 30 degrees in five minutes of the summer. And it’s the middle of the summer, and you’re like, what? So a lot of people don’t, don’t know that lesson I am speaking of kind of being prepared for the weather. And from a more personal standpoint, I’m the king of shorts, Ryan, I love wearing my shorts. So dress. Dressing in layers is hard for me, not my strong suit. I There’s lots of pictures of Connie in like, 15 layers next to me, in shorts and a T shirt. We’ve, we’ve got, like, a whole album of photos of us, juxtaposed with how we dress.

Ryan Fleming  14:57

Are you guy that it’s snowing out and you’re in shorts? Yeah, I

Walter Storholt  15:00

was actually out in it, in my flip flops the other day, and, you know, the sun was out. You know, it was post storm, so it was kind of warm. But, you know, I’m a little, I’m a little crazy when it comes to snow like that.

Ryan Fleming  15:11

Off. To give a shout out to my nephew, Jackson Nutter, because he is the worst. He grew up in Aurora, up in Denver, yeah, and that kid, I don’t think he ever put I’ve never seen him with pants, ever, yeah, yep, and it would be freezing out, and he would have shorts on all the time.

Walter Storholt  15:27

Yeah, I’ll wear pants to church, and if we’re snowboarding, then I’ll put some pants on, because I’m going to be falling all the time, and definitely need them at that point. But that’s about the only time, basically,

Ryan Fleming  15:37

when you’re forced to Yeah, pretty much. So since you’re doing podcasting and all that, you do have at least shorts on right now, right

Walter Storholt  15:43

do you think I really have pants on under this desk?

15:50

I do have shorts on. I do have shorts

Ryan Fleming  15:53

lost all of our listeners with that one comment. And then everybody started having this horrible visualization. I’m sorry. Everybody’s off the podcast just like

Walter Storholt  16:01

that. Gotta be careful what you say. Oh, my God, we were doing

Ryan Fleming  16:04

pretty good, too. Walter, we started getting all these followers and stuff. I mean, we had a lot of

Walter Storholt  16:09

people now they’re all gone. They’re all gone. Oh, I gotta somehow bring that back into a financial comparison here. But yes, dress in layers. Be comfortable as the conditions change. I don’t know. Give me a financial lesson at addressing in layers.

Ryan Fleming  16:26

I think you kind of hit on it, you know? I think diversification comes into that. So we have our risk spread out. I think that different pots of money, different types of investments, and I really think going into retirement, that’s half of it. And the analogy I like to bring back to airplanes. I know we’re talking about layers for the snowstorm, but for airplanes, it’s we want redundancy. We want different systems in place so that if hydraulic system number three goes out, it’s okay. We’re going to be all right, because we have a we have design, we’ve designed a portfolio that can handle any of those conditions, and it’s ready for it. So I think having a well diversified portfolio, having layers, having different pots of money, having a bucket strategy in retirement, all those things, you got to prepare for the worst. If you don’t prepare, then you can’t handle the changing conditions.

Walter Storholt  17:20

Yeah, it’s a great point. You got to be prepared for the temperature to drop, the temperature to go up the market, to go up or go down or stay the same. You’ve got to have plans that fit into that. I’d imagine as a pilot, right? And with planes, these things are built to have a billion different fail safes and operate in lots of different environments, and they give you the tools to constantly adapt and change. That’s just like dressing in layers. It’s just like diversification, so that you can have something that’s doing well in your portfolio during a bad time for something else. I mean, it makes tons of sense.

Ryan Fleming  17:51

There’s a couple of things I see with investors, too, that I just want to talk about, and that is, I think one of the biggest mistakes I see is people not being aggressive enough. You know, like, time factor is the biggest factor, but you got to, you got to let your money work for you. And there’s this whole thing right now of when the markets at an all time high, or things are really good, people are panicked and they want to, you know, they create in their mind because of the short term noise that there’s going to be this huge crash. And, you know, a mentor of mine, a very smart guy, he always said, don’t fight the trend, man. You know, if the market, first of all, you have to have all time highs to continue to have the market go up, it’s just the way it is. Yeah, so don’t be afraid of an all time high. That just means the market’s doing what it’s supposed to do. But, but rather than fighting the trend, jump on there and ride it. Ride that wave. You know, fight it. Ride the wave.

Walter Storholt  18:45

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Ryan Fleming  20:50

It actually is, I mean, and I think those of us that are a little bit type A and we, I won’t say we like to work, but that’s just a part of our purpose in life, you know, is to be productive. It is hard, and this snowstorm for me has been a little hard, just because sitting around for multiple days in a row at the house, not, you know, not not leaving, not going and doing something, is difficult. Thankfully, I have a back injury right now, so I’m not moving too much. But yeah, get, you know, watch the snow fall, brew up that cup of coffee, that hot cocoa, whatever it is, and sit back and enjoy it. And I think that, I think that with investing, retirement is that much sweeter when you know you worked hard, you know you did all the right stuff, you know you saved, you know you put in all that work so that you can enjoy those go, go years, sit back, travel with your companion, and not worry about finances, not worry about money, because you get in that, that backside of all when you put in all that work, you’re not worried about running out of money, because you’ve already got that compounding interest working for you, and life’s good.

Walter Storholt  21:59

Yeah, my final thought is that snow days don’t last forever, but the memories that they create certainly do, and I think it’s the same with finances and building toward retirement, your working life retirement, we know it’s not going to last forever, but we can create some awesome memories with good, solid planning. It’s going to give us freedom. It’s going to allow us to have fun on those days. We’re going to be ready when the conditions change all the things that we’ve talked about here, Ryan, so go out there, build those memories. Save hard, play hard, and you’ll be in good shape.

Ryan Fleming  22:30

Yeah. And I just look at that, and I think about just making a little bit more sacrifice day to day right now, saving just a little bit more will make all the difference. In the end, when you’re in retirement or nearing retirement, and you’re you’re on the better side of that curve where you’re not trying to play catch up, and it’s really sad when people are trying to play catch up before retirement because they they didn’t put in the work early, because it just doesn’t work the same way. Yeah, that time factors gone.

Walter Storholt  22:58

Ryan, let’s take lesson from our show that we’ve just recorded. You got snow on the way, so go get ready for it. Enjoy it with the kids, and hope it’s a good time. Don’t, don’t be all ba humbug about the snow.

Speaker 1  23:09

Did you just throw another snowball at me? Are you over here? Or maybe you’re over here?

Ryan Fleming  23:16

Well, that’d be a good closing I’m gonna go hunker down for this the next snowstorm that’s coming in and and then just imagine going out in the snow, and you remember those snowball fights where you’d have all your buddies and you’d be winging snowballs at each other, for

Walter Storholt  23:32

sure, absolutely, that’s what I think. Go out there and do some of that. All right, everybody, thanks for joining us. We’ll see you again right back here on the pilots advisor. Take care. See you.

Speaker 2  23:41

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.