Preview of what we’ll cover today:

🚨 Comparison Trap – Why measuring yourself against others backfires

🧭 What “Enough” Means – Retirement readiness is lifestyle-driven

📊 The Real Math – Income needs matter more than account size

🧠 Emotional Confidence – Why even good savers feel behind

🎯 Action Steps – What to do if you truly are behind

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More About This Episode:

Nothing wrecks financial confidence faster than comparing your savings to coworkers, siblings, or someone bragging online. Ryan unpacks why comparison is not a retirement plan, and how it can distort what “behind” really means. You’ll also hear about what actually determines your retirement readiness.

Go Deeper Into The Episode:

0:00 – Intro

1:07 – Listener Question – Am I Behind?

3:11 – Emotional Reassurance

4:33 – Question Your Assumptions

8:13 – Strategies to Catch Up

10:59 – Get Real Data

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: You know, nothing will mess with your retirement confidence faster and more severely than comparing your savings to your brother, your sister, your coworkers, or even that guy on YouTube who said he retired at 35. And you can do it, too. Uh, sometimes as exciting as those things sound, they’ll actually get you down in the dumps. When you start playing that comparison game, it might make you feel like you’re behind on your savings. Well, this resonates with a recent question we got from a listener to the podcast. We’re going to cover their question and talk a little about what to do if you are behind and how to tell if you’re even behind in the first place when it comes to your retirement savings. Let me grab Ryan and we’ll get started today on the Pilot’s Advisor. Ryan, great to talk again with you today, my friend. We’ve got a great listener question to cover and, uh, dive into here a little bit if, uh, you’re new to the show. By the way, I’m Walter Storholt. I’m always joined by Ryan Fleming. He is the pilot’s advisor. If you are a pilot and need specific advice, guidance, help, when it comes to retirement and financial planning, he is the person to turn to and to talk a little bit about your situation and what to do about it going forward. Uh, you ready for the listener question here, Ryan? I’ll read it out to you.

Ryan Fleming: Uh, sure. I guess I don’t have a choice. I hope they said no.

Walter Storholt: It would kind of be a short episode, I guess.

Ryan Fleming: Well, hopefully it’s a good question that I can answer because I don’t know what you’re throwing at me. So here we go.

Walter Storholt: All right, so the listener says, I don’t have a name for this one, but listener says, I thought I’d done a good job of saving over the years, but it seems like I’m probably behind where I should be. My brother has nearly $2 million saved, and it seems that most of my colleagues at work are in a similar stratosphere. But my husband and I are barely over the million dollar mark and we’re now in our early 60s. What should we be doing to get caught up?

Ryan Fleming: Well, I think the big premise here that we got to ask the question is, you know, you can compare yourself to someone all day long, but everybody lives their lifestyle completely different. Um, I know many people that live well within their means and don’t spend that much, so they don’t need that much in retirement. I know other pilots that live large and they have a Huge nut to crack every single month. And they probably need $500,000 of income to sustain life. So those are going to require two totally different, uh, savings. I think the bigger factor is to understand how much you truly have to save in retirement to replace the lifestyle that you currently live. And what I like to tell people is, you know, $1 million at a safe withdrawal rate is going to spit out between 40 and $50,000 a year. And then you need to factor in Social Security and then maybe any pensions you might have, and you can start doing the math on retirement and starting to figure out if you’re okay or not. But it really, really is a case by case basis.

Walter Storholt: Yeah, that’s a great point. I think that is kind of the, the real issue here is that, uh, comparison is not a financial plan. So that you’re not digging into anything. You’re not helping yourself really with that comparison game because you’re learning information about their situation, not your situation. And that’s what you’re getting to the heart of, Ryan, is that you may live a completely different lifestyle than that person you’re trying to compare yourself to. And it’s, it’s not, we’re not talking about a thousand dollar difference. We’re talking about wildly different numbers depending on those lifestyle differences.

Ryan Fleming: Well, the other thing that I’ve learned from, from working with clients is everybody wants that emotional reassurance. Um, I’ve found that the people with the most money worry the most about money. And some of the people that don’t have a clue what’s going on don’t worry about it at all, but don’t realize how much of a conundrum or an issue they’re about to run into in retirement. I think that, um, everybody probably feels a little bit behind. I don’t think everybody sits there and go, oh, I’m done. I’ve already saved for retirement. I think it’s, it’s more likely that you’re going to feel inadequate or a little bit behind and feeling like you don’t have enough saved. Um, but once again, like we talked about, the comparisons don’t, uh, help either because everybody has their own situation, lifestyle. Maybe you have some inheritance or different expenses out there. Maybe you’re trying, you know, some people have debt, um, health issues. So there’s so many variables out there. So you really have to analyze your current and specific situation to really have it make sense.

Walter Storholt: Yeah, it’s really reframing that conversation. What’s enough for you, not what’s enough for somebody else? And something else that strikes me in this question, Ryan, is, you know, a lot of people, I’m sure you see this in your office all the time or on zoom calls with, with potential clients is, uh, the amount of assumptions people make. And this listener, uh, this question, um, and it’s a great question. We’re glad that you asked it, by the way. Listener. Certainly not trying to throw you under the bus here, but just some honest conversation about it. Lots of assuming in this question. Right. And a lot of people assume they’re behind on their savings without doing the digging. And I’m sure you see assumptions pop up in more than just this area.

Ryan Fleming: Absolutely. And I always try to question the assumptions because, you know, people, when they think about assumptions, they’re going to leave those out there as variables that you’re not going to attack. And I think you should do the exact opposite and turn into those assumptions and say, well, why, why are we assuming that?

Walter Storholt: Yeah, um, let’s assume is for other areas in life, in financial, uh, planning, we want as few of those let’s assumes as possible.

Ryan Fleming: Yeah, well, and it’s amazing too, how people just have completely different lifestyles of what they envision in retirement. There’s, there’s couples that are like, I’m not leaving a dollar to my kids, and there’s others that, uh, want to basically spread out the whole generational wealth for their children.

Walter Storholt: Yeah.

Ryan Fleming: And then some people don’t have kids.

Walter Storholt: And then two, a couple of variables that dramatically change the situation.

Ryan Fleming: Absolutely. And. And you know, most of the time I start having these conversations with pilots where they’re 60 and they’re start trying to get near the end and they want to retire. But every once in a while I’ll have, I’ll have a conversation. As a matter of fact, recently I’m going to bring this one up where, um, I had a conversation with one of my clients, and he’s doing very well. He’s always been a good saver. I would say he’s more intelligent than the average bear, but he’s 50 and he’s like, I’m done. I don’t really want to do this anymore. And I’m like, whoa. You know, I’m not used to having this conversation with somebody that’s 50. Um, but he’s, you know, he’s like, I don’t need more money. I don’t need to, you know, live off, you, uh, know, I know what I need to live off of, and I don’t need more than this. And he’s very comfortable with, um, the, the numbers that we’re looking at. So it’s, it’s, it’s just interesting to see the different dynamics of all the different people out there and how they think and what’s important to them. Is it more money or is it more time or travel? And, and, and I think that really defines how you’re going to come up with that plan.

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Walter Storholt: Great point. Let’s say you do dig into the numbers and somebody is actually behind where they need to be. So pivoting here a little bit, we’re tackling this question in the first half as. All right, let’s make sure you’re actually behind. Now let’s say someone is actually behind. Um, what are your opinions about the various catch up strategies available to folks out there?

Ryan Fleming: Well, this is where it becomes a difficult conversation. And I always say that I give tough love, but I’m going to tell you how it is. And the one, the one, the biggest factor and the one thing you can’t change is time. So if you’re behind, I’m going to tell you you’re behind. And then we’re going to start talking about the sacrifices you’re going to make to be more aggressive, to get caught up. Because especially in the pilot career field, we have an end game and that end game is 65 years old or any health issue. Uh, you know, there is some other opportunities out there, whether you’re a sim instructor or you go fly a couple more years for NetJets, but there’s no magic equation here. It’s just saving it’s putting money away and then letting. Letting that money work for you. Um, I’m amazed at how much people don’t understand tax, strategic tax planning, how they don’t understand the distribution phase, how they don’t. Don’t understand that you have to pay income tax on what you saved or just not taking advantage of all the little details that your 401k or your. The benefits that your airline may provide for you to. To fill all these holes and squares that we have to fill to be prepared for retirement. I have conversations every single day with somebody that might have been at the airline for 25 years and has not taken advantage of some of the benefits or the little details inside their 401k that could have got them in a much, much better position.

Walter Storholt: Yeah, that’s a great point. And what I’m hearing you say is there’s just a lot of levers that can be pulled to help change the math, change the strategies. But we’ve got to look at them. We got to know that they exist. We got to try whether it’s putting a little bit more in those last couple of years into your retirement accounts to make up that gap, or, hey, delay retirement by a year, and that accomplishes everything. Is that a doable option? Um, you can then combine a whole bunch of those different things, from a tax strategy to adding a little bit more to your savings, to delaying it maybe only two or three months. Like, I’m sure there’s all sorts of different things. You can say, hey, we’ll. We’ll make seven small tweaks, and it’ll equal one large tweak. So many different things that you can do to help somebody get over that hump if they are indeed behind a little bit.

Ryan Fleming: There are so many variables, and I think the one thing that doesn’t work is ignoring it, kicking the can down the street, or at least not ordering the toolkit and setting up a call. And let’s discuss your financial situation, because there’s probably. Or, uh, what I always like to say is, you don’t know what you don’t know. So there’s many pilots out there that think they’re doing just fine or think they have it under control, but there’s this whole space and all these variables that they don’t even know are part of the game. And I think just having a conversation, I can tell right away when somebody’s flying blind or somebody that actually has a radar that’s working.

Walter Storholt: I’ll wrap it up with one last comment on assumptions and that is if you assume you’re going to be okay in retirement. Or the opposite, if you’re assuming I can’t retire, I just need to keep working. Uh, neither one, uh, may be correct. And so reach out, uh, to Ryan, Order the toolkit. It sets you up for that free portfolio analysis that we talk about all the time here on the show where you can have a one on one conversation about your plan, where you are right now, where you’re headed into the future, whether you’re a good fit to work with one another, what kind of differences can truly be made about your specific situation. If you’re a pilot, take advantage of that opportunity. Again, there’s a link in the description of today’s show where you can order the toolkit. That’s all you have to do. And then, uh, Ryan will connect with you and take it from there. But it’s going to get you some books. Great resources, lots of fantastic information to help pilots retire successfully and much, much more. Ryan, thanks for, uh, a great episode and answering this listener’s question, and we’ll talk with you again soon.

Ryan Fleming: Sounds wonderful, Walter. Everybody out there, fly safe. Order the Toolkit. And I look forward to meeting with you.

Voice: 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.