Preview of what we’ll cover today:

🎖️ Veterans Day Greetings: honoring service and sharing personal updates

🧠 Emotional & Financial Security: balancing independence with connection

💬 Open Communication: why honesty about money is essential for trust

💵 Retirement Readiness: aligning income, savings, and lifestyle goals

👨‍👩‍👧 Family Dynamics: protecting children and legacy from previous marriages

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More About This Episode:

Getting married in your 50s often means you’re combining lives, but not necessarily combining finances. How do you build a retirement plan together when you’ve both already built your own? In this episode, Ryan answers a listener’s question about navigating financial and emotional security in later-life marriages. Financial independence and emotional connection aren’t opposites, you can keep your accounts separate, but your retirement plan should still be built together.

Go Deeper Into The Episode:

0:00 – Intro

2:31 – Marriage Later in Life

3:52 – Financial Planning in Second Marriages

6:29 – Having a Shared Vision & Emotional Security in Late-Life Marriages

8:40 – Practical Advice for Financial Planning

12:09 – Importance of Communication with Your Spouse (Especially with Kids)

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

On today’s edition of the pilots advisor, we’re talking about marriage, and actually, it’s a topic that I think will resonate with a lot of pilots, and it’s what happens when you marry later in life. How do you prepare for retirement? This is inspired by a listener and a viewer question on the show, and so we’re gonna dive into that next I’ll grab Ryan and we’ll get started. You. Ryan, welcome everybody to a new episode. This is the pilot’s advisor Walter Storholt alongside Ryan Fleming and looking forward to our conversation today, a little bit about marriages later in life and how to handle those things, Ryan. But before we dive into all of that, we’re recording today on Veterans Day. So Happy Veterans Day, my friend, thank you for your service. And you had the Air Force hat a second ago. I thought you were going to rock it on the on the show a little.

Ryan Fleming  00:46

I could throw it on. I could throw it on, and you actually helps me with the big forehead I have. You know, these cul de sacs keep growing. I’m not young like Walter, but there we go. I don’t mind give a little love out there, but

Walter Storholt  00:59

and the sweater as well, I guess, yeah,

Ryan Fleming  01:04

yeah, nice, and it is, yeah, I know I do the black and white, but it’s green. This is all, you know, kind of camo looking. But you know, Walter, I appreciate that many, many of our listeners are veterans, so I want to present, want to say Happy Veterans Day to everyone. Thank you for your service and sacrifice, even especially those that made the ultimate sacrifice. So we are recording this on Veterans Day. I also want to point out that Walter fell down the stairs today, and Walter also had a a baby boy two weeks ago.

Walter Storholt  01:38

That’s right, just a little over two weeks from the day. So we’re pretty excited over here. The lack of sleep was the reason for the fall down the stage.

Ryan Fleming  01:46

An amazing congratulations. He might be a little lacking on sleep, and so he might not just be as amazingly professional as he normally is, because he’s barely

Walter Storholt  01:58

awake right now, if I say anything incoherent, you know why? Right? Perfect.

Ryan Fleming  02:01

I love every bit of it, because, guess what? We’re real people in life happens, and having your first child is an amazing event in your life. So congratulations, man, that’s awesome. Well,

Walter Storholt  02:12

we’ll get him on here with with a pilot’s advisor hat before too long, and have him make a camo cameo appearance for you. So absolutely, let’s go well Veterans Day and having a new baby. No real great segues from those things, Ryan to our actual topic today that we’re diving into. But sometimes you don’t need the segue, right? So we’ve got this question from a listener, and wanted to bring it up to you on the show today, because you identified this right away as, hey, this is something that pilots deal with. It’s a tough career, right? So there’s often divorces, second marriages. It’s just tough on on a marriage. I mean, that’s the reality of it, right. Before we even get into this question, there’s a lot of remarriages. I think in the industry, would you say, from what you’ve seen, yeah,

Ryan Fleming  02:56

I would definitely say that. And, you know, I hate to say it, but a lot of my job, in many cases, is kind of counseling, and a lot of case, you know, like, with a lot of different situations, and I’ll have a client of mine, and he’ll be in, I hate to say he, but many cases, it’s a he, where he’s down in the dumps and, you know, he’s talking about how he’s getting a divorce, or this is going on and, and I’m like, Dude, you are not the first pilot that I’ve ever worked with that is divorced, you know, or getting a divorce. Unfortunately, it is a tough business. You’re gone a lot. It takes a special type of person to be able to handle a relationship like that. So, yeah, I would say there’s a higher percentage of divorces in our industry. For sure, it’s

Walter Storholt  03:37

got a lot of challenges in it, I guess, much like military and deployment. So there’s our segue with it being Veterans Day. So I would very much agree with that 100% Yeah, odd schedules not fitting into the rest of the mold that the rest of the world kind of operates on. Well, we won’t focus so much on that divorce side of the equation, and we’re focusing more on that, okay, I’m getting remarried side. So here’s the question. Lister says, I’m about to get married. We’re both in our 50s, and it will be my second marriage and her third. I’d like to keep all of our assets separate so that we each have our own financial lives and don’t have to fight about money. But how do we plan for retirement if we don’t really know what our total numbers look like? Great question, I’m sure this is kind of echoes some of what you’ve heard before from folks.

Ryan Fleming  04:23

Yeah, I think we just need to have an open discussion about it, and I’ll tell you what I’ve seen or what I feel. I think, in a first marriage, when people keep their finances separate, I’ve found that it’s not necessarily a good thing, because it’s almost like you’re not going all in on this marriage. And my advice, if I, if I’m asked, is that, no, I think you guys should combine your finances and start planning for your future and for your retirement together with one pot of money. Okay? And I’ve just found that people keep their keep their finances separate, tend to not do well. However, once. Moving on to that second marriage. And the other thing that I find that anybody that gets a divorce says they’re never going to do that again. And two to three, two to three years later, whatever might have happened, it’s time for them to do it again. And all of them get married again, in most cases. So I’m never doing that again, but here we are, three years later, she’s different, he’s different. We’re going to try this again. But I find with that second that second marriage, or third marriage, in many cases, yes, they do keep their finances separate and and from for various reasons, I you know, I think it’s, it’s a different kind of marriage, usually, if it’s one later in life, because they’ve maybe both been married, they’ve have some battle wounds from what happened before, and want to make sure that they don’t make those same mistakes going forward. So I think communication is a lot better from a financial standpoint, but also keeping keeping the finances separate is normal, and I feel like it’s it’s not so much that the people in this relationship don’t want to combine their finances, but I think that emotions are a little more out of it, and it’s more about like financial security and just knowing that that they’re going to be taken care of no matter what happens

Walter Storholt  06:16

sounds like, no matter whether it’s an early marriage or a marriage like In this person’s question happening in her 50s or his 50s. Defining ground rules early is an important step. It just means those rules might look a little bit different, but let’s communicate about them, and open up those lines of communication early in the process, 100%

Ryan Fleming  06:36

and you know, Walter. Thank you for being here to always keep me. Get me back in line. Get me back in, inside the the lanes here. But yes, I mean, I talked talking about things and setting the ground rules. And if you are going to have a separate accounts, you need to have a shared vision. Yes, you can actually manage portfolios and have investments with one household, but in different accounts. And we just can, you know, look at the whole picture when we start looking at things, yeah, but I think that them talk, them talking about building a joint retirement, what that timeline looks like, what age they want to stop working. Obviously, for pilots, it’s kind of defined at 65 but I think from the very get go, having a vision of what retirement looks like and how that’s going to be, how travel is going to be, is a good place to start for them to when they’re even putting those accounts together, and start building and planning for the

Walter Storholt  07:34

retirement 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 homepage, there’s a beacon flashing. Get my free toolkit. 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. Yeah, it’s a great point, because you don’t have to. I mean, everybody’s shared finances are going to look a little bit differently whether they’re truly merged in an account or, Hey, they’re in separate accounts. But I know what you have. You know what I have? Do we split the bills? 5050, do you pay? Hey, you’re covering the electric bill. I’ll cover the water bill. All those arrangements can look differently, I suppose, but as long as they’re following that same vision, and you can build towards similar goals. That’s what you’re really trying to it sounds like walk couples toward when you’re involved in these discussions, yeah.

Ryan Fleming  09:10

And the funny part is, even if it was a first marriage, many accounts are individual retirement accounts. Like I get people to ask me to try to make it a joint account all the time. And right? Well, I can’t do that by definition. An IRA or a Roth IRA is an individual retirement account, no different than a 401, K. So keeping things separate, a lot of things are separate all together, except

Walter Storholt  09:33

for, where do I have to log in information or not? Right? Yeah. And

Ryan Fleming  09:37

where it merges is, you know, taxable investment accounts and checking accounts. You know those can be joint or individual, but if you are married, in many cases, you know protected by the state or as a primary beneficiary is normally that other spouse, so you can still have a lot of transparency without merging accounts, because it’s kind of a normal thing. But yes, the merging of. Bank accounts and the merging of taxable investment accounts is really that that area that that sometimes where you got to draw the line. And another thing that actually happens is pilots marry other pilots, and I found that when that happens, you know, they keep their accounts separate from the time prior to them getting married, but then, going forward, they decide to have a joint investment account. So they’re they’re keeping separate what they’ve done up to their lives at that point, and now we’re going to move forward together. So there’s many ways to skin the cat, but no different than what we’re talking about, I think transparency, where you can see each other’s accounts, even though you might not have access to them and or be a beneficiary on them, or and also, communication are huge. Where I think it gets messy, and you know it’s you got to talk about these things. Where it gets messy is many times in a second marriage, the couples have already had kids previously, so now you might have a kid at home, or two kids at home, or you might not have any, but you know that you still have a conglomeration of of children. And when you start thinking about estate planning and beneficiaries, many times there, you know there’s that gray area where they don’t want to talk about all my money going to her kids, or I don’t want my money going to his kids. So I’ve been put in some uncomfortable conversations where you like, Okay, well, we’re not having this conversation here, and they might want to talk to me offline, and that’s fine, but I think these are, these are, I mean, life happens. Life is messy, and I think the more that you can have have transparency, get on the same page, maybe you shouldn’t be marrying somebody if you can’t truly talk to them about your your hopes and desires for, you know, for your your children and your your combined family. But you need to have those conversations. It’s tough if we

Walter Storholt  11:54

were more like a sports show with, you know, lots of animation and things like that, Ryan, I might say that you just dropped a truth bomb there at the end, right? Like, if we can’t communicate about these things, maybe a red flag, but that’s very realistic, and probably not something they’re hearing from enough people, if that’s the case, and that’s where you as that neutral third party, as the advisor, can kind of not that you want to be doling out marriage advice and those kinds of things all the time, but that might be where that neutral third party is able to say, hey, maybe you guys are approaching this the wrong way. What about looking at it through this lens, or looking at it through this angle? I can just see how important and helpful that can be. But your point on the kids too? I mean, that’s whole different can of worms, right? And that’s often what it is, is it’s like, hey, spouse to spouse, we don’t really care about the whole shared finances thing, but it’s when it comes to the kids. Is where it is, especially if you’re getting married later in life, like you weren’t a parent necessarily, to those kids growing up, right? You may not have much of a relationship with the other spouse’s children. Therefore, that’s why people, I think, view that separation of those finances really important in that regard. So you said it, it’s messy, and that’s why it’s an important question, not to just gloss over,

Ryan Fleming  13:01

yeah. And, you know, obviously one size doesn’t fit all. But maybe the estate planning conversation, you know, setting up wills, beneficiary designations amongst the kids, you have to have that conversation and get it set up early on, because it could be a point of contention later on that could lead to the next moving on to the next divorce. But, you know, and that’s where, you know, we talk about them, we talked a little bit more about emotional trust, that late life marriage, it’s a lot more about emotional security, as much as financial security, like making sure. Because I think, I think when you decide to get married again. A lot of it is, hey, I want to share my life with somebody. I don’t want to be alone. But those needs are actually a bit different than they were the first time around. I think that people a little bit younger, marry more with emotion, follow that lust and then kind of figure out, oh, that kind of goes away. And I married, you know, hopefully you married your best friend and that, that teammate that you wanted to be with for the rest of your life. And I think that marriage a little bit later in life, whether it’s your 40s or 50s, you you’ve taken some of that, that that emotional side out of it, and you can take a step back and say, Hey, is this my best friend and somebody I want to share life with, and it’s a little bit more of a, I don’t know if I’m using the right term, I’m not a I’m not a counselor, like, I mean, you know, I get to be one. This is an interesting topic. Walter, bringing this one up, yeah,

Walter Storholt  14:32

opens up a whole bunch of other offshoot conversations we could dive into on other episodes, absolutely so, but I think you’ve covered it well, bottom line is, plan together still, please, so you can achieve those retirement goals even if one of you, even if you don’t see the other person’s account and have access and logins, and one’s paying the water bill and the other the electric and so on and so forth. When it comes to planning for your financial future and retirement like, let’s at least have a shared. Vision of the big picture, otherwise you’re seeing lots of stumbling blocks in the road if we’re not sharing that big picture. So there’s definitely sort of the short term, or like micro view of the day to day, and then the larger view that needs to be more open and have a conversation about it if you want us to have success. It sounds like

Ryan Fleming  15:17

what Walter said, That is perfect. Have those conversations have transparency and set some ground rules. Up front.

Walter Storholt  15:25

I may be going on lack of sleep, but we dug deep back there to pull out some wisdom. So about that? Well, hey, if you are looking for an advisor to not only talk about some of these kinds of issues, you may not be going through a new marriage late in life, but maybe some other financial problem that is kind of bothering you or on your mind or that you’ve got questions about, Ryan’s always there for you as the pilots advisor. It’s easy to get in touch with him. All you have to do is, of course, go to retire pilots.com we’ve got a link in the description of today’s show. In fact, whether you’re watching on YouTube or listening on your favorite podcasting app, where you can then go and download Ryan’s toolkit. It’s going to walk you through all the important things that pilots need to know about retirement, about financial planning. It’s packed with his books, special reports, lots of goodies in there as well. Physical box that Ryan’s going to send out to you order that toolkit. It also comes with a review of your portfolio as well, in a one on one setting with Ryan. So if you’d like to take advantage of that again, click the link in the description. If you’ve never done that before, go ahead and schedule that time to meet with Ryan, in addition to getting your toolkit and you’ll be well on your way to getting a bunch of those questions answered about your retirement future, Ryan, thanks again for your service and Happy Veterans Day to you, and we’ll catch up with you on the next episode. Sounds great. Walter, everybody. Fly safe, take care. We’ll see you again next time, right back here on the pilot’s advisor.

Speaker 1  16:48

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