Preview:

The market’s been shaky and pilots are wondering how the volatility impacts their retirement and investment decisions. In this special mailbag edition of the show, we’ll answer real questions from aviators facing turbulence in their retirement plans.

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More About This Episode:

Whether they’re near retirement, sitting on cash, or watching everything dip at once, today’s questions all circle one theme: how do I respond when markets get rocky? Join us for guidance on how to chart a steady course.

Ryan covers how to stay grounded in volatile markets, the myths about getting more conservative with age, and why timing the market is often a losing game. With the precision of a pilot and the mindset of a planner, we’ll help fellow aviators navigate the kind of financial headwinds that leave others guessing.

Here’s what we cover in this episode:

💡 The truth about timing the market

✈️ Diversification myths: are you as protected as you think?

📊 Rebalancing during downturns: risk or opportunity?

🧠 Emotional decisions vs. system-driven strategies

0:00 – Intro

0:23 – Watching A Portfolio Dip Near Retirement

3:58 – When Is It Not Time to Stay the Course?

5:37 – Sitting on Cash, Should I Wait or Dive In?

8:03 – Will Diversification Even Help Me?


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 

On today’s episode of the pilots advisor, we’ve got questions from viewers and listeners like you other pilots who are wondering what to do about their finances. Specifically, all of today’s questions have to do with crashes and market downturns and how to react. So we’ll cover a couple of different angles here. I’ll grab Ryan. Let’s get started. Well, Ryan, today’s episode should be a fun one, because we’ve got questions from pilots out there who are wondering about how to react when we have market downturns like we’ve had in 2025 already, before and future ones that come down the line. Hopefully this advice would be helpful to folks to hear today. So you ready to get peppered with some of these questions? I’ve not given you much advanced warning on these. Warning

Ryan Fleming 

on these. Yeah, I know. I mean, we record these podcasts, but this is almost like us recording live, because I have no clue what’s coming at me. Hopefully I won’t say something stupid, but serve it up on a silver platter. Walter, let’s go.

Walter Storholt 

All right. This one’s from Mike, who flies for Delta. Mike says I’m about two years from retirement, and watching my portfolio take hits freaks me out. How do I protect myself without locking in losses when the market goes down?

Ryan Fleming 

Well, I think you only lock in losses if you make an emotional decision and sell or get out while the market’s down. I mean, that’s the only way you lock in losses. And when you build out a portfolio, I mean, we know that these market corrections or the volatility is going to happen, it’s all engineered into your portfolio that we’ve built out. The other thing to consider, when you think about getting closer to retirement, most people think that they have to get a lot more conservative. And that’s just the way it is. Like, Oh, I’m 60 now, or I’m 62 I need to really pull the throttles back, and I need to be like, in a, I don’t know, a 6040 model or asset allocation. And what I mean by that is 60% in stocks, 40% in bonds, having having a more conservative approach and a lot less volatility. But the reality is, it really depends on your time horizon for the money. Okay? If you’re planning on working till 65 you don’t need to pull the throttles back when you’re 60 there’s probably two or three market cycles in that five year period. So I think it’s so important to just not be emotional in the short term.

Walter Storholt 

That’s huge. Trying to control our emotions will be kind of an element, I would imagine, of a lot of these answers, because that’s certainly what it comes down to.

Ryan Fleming 

And I want to add something to that too. I think I’m just trying to think back on the question. I know he talked about locking in losses, but I think he said something about, how do I protect myself? Well, in the markets, there’s risk. Obviously, if you put your money in the market, you’re taking on risk, but ways that you protect yourself is by being diversified. Okay, the more diversified you are, you actually can actually lower your risk and increase your return, which is modern portfolio theory. I think other ways that you protect yourself is by being unemotional. Don’t, don’t make short term emotional decisions with your money. Always think long term, other ways that you protect yourself as having a system in place, you know, so that it, it keeps you from pressing that button, or, you know, jumping out of the market when, you know when it hurts. And I actually think that’s one of the values of having an advisor, because I watch it all the time with with do it yourselfers, when the markets are really bad and they feel the pain, well, they have the ability to click a couple buttons and get out of the market. When you have a financial advisor, that’s not the case. I mean, there’s, there’s going to be a conversation that’s going to happen, you know, and many times I’m going to try to talk you off the ledge and and that level of protection, that would be another way that you could protect yourself is actually having a financial professional who understands how markets work, studies this stuff, studies behavioral finance and and that’s a way to have protection. Or, you know, for airplane airplane redundancy in your systems, per se. All

Walter Storholt 

right. Another question here is from Terry, who flies for American and Terry says the market has dropped in the past this year, and it’s really hard for me not to panic when this occurs. I know from listening to one of your previous episodes, I’m supposed to stay the course. But how do I know if I actually need to make some changes to my investments? Is there a trigger, Ryan, when you say, okay, staying the course is great, but we got to make some some adjustments here.

Ryan Fleming 

Well, I think being long term is definitely a way to think, but any market downturn or any volatility in the market might trigger an opportunity for you to reallocate your assets. I see this all the time, when people fall in love with the stock, and they might have lost, you know, a lot of money in the stock, and they’re sitting there on it, waiting for it to come back. I mean, at some point you just got to cut your losses and sell out of that and reallocate and be more diversified. So I see, you know, there’s no magic pill say, When should I change my investments? But I think that that’s the problem when. People are doing it themselves is they really don’t know how to take advantage of market volatility, whether it’s up or down, to either lock in some gains or tax loss harvesting in a taxable account with with a down market. And so this is, this is why you want to hire a professional and, you know, I think about it with taxes. Yeah, I understand taxes pretty well, but I know that I’ve saved way more in taxes by hiring a CPA, and somebody that’s constantly in the news constantly has their finger on the pulse with all the all the changes and that little bit that you’re going to pay them more than they can, more than make up for it with stuff that you wouldn’t have thought about or weren’t doing. This is

Walter Storholt 

an interesting question here from Arthur. Arthur says I have some cash on the sidelines. I was planning to invest it slowly, bit by bit over time, but now I’m wondering, should I just put it all in and buy the dip next time there’s a small decrease and go for it? Or should I just keep waiting things out? It sounds like he’s trying to time the market. Well,

Ryan Fleming 

100% he’s trying to time the market. And if I could predict the future, I could tell you exactly what to do. The reality is, the biggest factor in investing is time. So if you looked at it that way, you’d go, we’ll put it all in right now and let it do its thing. We don’t know where the market bottom is, but we know anytime there’s a market that’s depressed or has had a big sell off, it’s an opportunity. So, yeah, I would, I would buy the dip. I mean, buy when things are low, you know, and other options, it’s whatever is going to make you feel okay. I mean, if you want $1 cost average your money into the market, you can do that as well. And of course, as time happens, it’ll play out and and we’ll know if that was a good decision or not, you know, depending on what the market does, but, but I still think about it, where you got to take the emotion out of it. You got to know that the markets up on average, three out of every four years, and that time, time and asset allocation in the market is the biggest factors.

Walter Storholt 

Attention aviators, when you’ve spent years in the cockpit managing the complexities of flight, isn’t it time you navigated your retirement with the same precision? Introducing retire pilots.com right at your touchdown zone on our home page, there’s a beacon flashing. Get my free tool kit. Click that, and you’ll be cleared for a direct route to Ryan’s retirement toolkit, tailor made for pilots like you. Inside, you’ll find two of his important works, the pilot’s advisor and pilots retire early. Between these two books, you can decipher the nine critical decisions when retiring before 65 and discover the seven lessons to help pilots land safely in retirement. But that’s not all. This toolkit is packed with altitude high value, including extras to get your retirement plans off the runway and light the afterburners on your 401 k vector, on over to retirepilots.com to grab your toolkit and let’s embark on this journey together. All right, we got one more question here from Larry, who flies for JetBlue. Larry says, I’ve got a diversified portfolio. This is a good one, Ryan, but when everything is going down at once, like it did earlier this year, what’s the point of diversification? Is there anything that actually helps when the market’s taking a dive.

Ryan Fleming 

Well, I think it’s happened in the past where, you know, there’s there’s no solution when everything’s going down. Okay, that’s just the way it is. But in most market conditions, that’s not the case, where everything’s going down at once. So diversification is still your friend. Even earlier in 2025 when the US markets were actually having a nice pullback. International markets were doing just fine. So if you had a diversified portfolio, you weren’t losing money like you would have been if you just had US stocks. So diversification is always your friend, but, and that’s a long term way to look at it. Now there might be short term where everything is going down, but that doesn’t mean you abandon a principle that we’ve studied and looked at for decades to help you lower your risk in your portfolio, and that’s diversification. Yeah,

Walter Storholt 

it sounds to me too, like maybe somebody in Larry’s position thinks they’re diversified, but if they’re seeing their accounts go down just as much as the broader markets, maybe they’re not as adversified diversified as they think. So that might be a good idea to get a review of your situation. Larry, if that’s what’s occurring, I would 100%

Ryan Fleming 

agree with that. And you know, first question you could ask is like, how how many holdings Do you have? And what actually is diversification? I mean, I don’t look at 2000 unique holdings as diversified now, 30,000 unique positions in 42 countries all around the world. That’s a diversified portfolio. And, you know, looking at the three factor model and Eugene fauma and Kenneth French, these are some of the things that you should study and look at to really engineer that quote, unquote diversified portfolio. Well, these were some

Walter Storholt 

great questions. Questions today. Appreciate everybody who submitted those to us, so we’ll have to answer some more questions like these again in the future. By the way, if you want to submit questions to us, you can certainly do that at retire pilots.com Just look for the comment form there, but that’s also the place to go to get your free retirement toolkit. This is packed with all sorts of great information, like you heard on today’s episode, but even more in depth, covering even more angles of the financial and retirement planning world. It’s packed with reports, Ryan’s books and so much more. So I always encourage people to go check out the toolkit as a starting point for advancing your retirement planning. But here’s a cool side benefit that comes along with getting the toolkit is you also qualify to then meet with Ryan for a portfolio review and analysis, and Ryan, this is where you get to really kind of go under the hood of somebody’s specific situation versus the broader things that we’re able to talk about here on the show.

Ryan Fleming 

Well, I analyze portfolios seven, seven days a week. I mean, you know, multiple a day. And so I’ve seen it all, but it’s so valuable to actually go in and see what a person’s doing with their investments. We can go back and pull their historic returns, you know, as many years back as as they’ve been invested, we can go look at those numbers and see how they compare to what we were doing here at the pilots advisor. And I just call it an IQ test, because, you know, the whole reason why we invest our money, the whole reason why we’re here, is to make our money grow. So let’s, let’s check it out, and let’s see if there’s a better way. Because, you know, if there’s a better way, and I can show you a better way via the numbers, why wouldn’t you do it? So I think having anyone look at your portfolio and get another analysis, or, as doctors used to say, let me get another another opinion, per se.

Walter Storholt 

Yeah, get that second opinion Absolutely. Well, again, all you have to do is go to retire pilots.com you’re going to see a nice big button there for the toolkit. Click on that, put in some of your basic information, and then Ryan will be reaching out to you, not only with the toolkit, but to set up that time to talk as well, to go through that analysis. And you can go really again under the hood with your personal situation. That’s the difference maker. See how your portfolio stacks up against what it could be with proper planning. And Ryan’s going to walk you through all of that. Well, great episode today, Ryan. Thanks for helping us out and answering these questions from our viewers and listeners, and we’ll talk to you soon.

Ryan Fleming 

Everyone fly safe. We’ll talk to you soon.

Speaker 1 

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