Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Jude goes over a few today that he thinks are worth asking. None of these questions are really about money. That’s kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely.
📌 Here’s some of what we discuss in this episode:
🏔️ Financial Freedom: Moving from accumulating wealth to using money to buy back your time
🎯 Your Why: Putting purpose at the center of your wealth once you reach retirement
💭 Dream Sessions: Using thought-provoking questions to uncover what really matters
❤️ Retire to Something: Finding passions, experiences, and meaningful work beyond your career
🪣 Bucket List: Prioritizing experiences based on timing, health, and mobility
🧠 Financial Psychology: Why shifting from saving to spending can be one of retirement’s hardest transitions
0:00 – Intro
0:43 – Financial Life Phases
1:43 – Putting the “Why” in Wealth
4:08 – If Jude Was a Genie…
6:10 – Retiring to Something
7:53 – Looking Back at Financial Decisions
9:47 – Prioritizing the Bucket List
12:19 – Psychology of Spending After Saving
13:24 – Reach out to Jude
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Episode Transcript
Note: This transcript was produced using AI, so please excuse any typos and inaccuracies…
Marc Killian 00:00
All right, Jude. This week on the Roth Guy, we’re going to come at this from a different angle. We’re going to talk about money questions that aren’t really about money. So I’ve got some different ways here to phrase some questions that you guys probably already phrased to to clients or potential clients. We’ll have a little fun with this. It’s a different take on how to, you know, just kind of think about the I guess the esoteric and the philosophical questions of retirement.
Jude Wilson 00:33
Yeah, and and the way that I like to have the conversation with our clients, you know, there’s two phases of your financial life. There’s the accumulation phase. I like to write it like going up a mountain. Every dollar that you save gets you closer and closer to the top of the mountain, and that’s where what we call financial freedom. Where no, you’re no longer spending your time to make money. Now you’re at the top of the mountain. You’re using your time to buy back 123, Now you’re at the top of the mountain, and you’ve accumulated a significant net worth. So now you’re using your money to buy back your time. So it’s no longer about you know piling in a lot of money into your net worth. It really is about making the quality of your life better, and what we tell clients at this stage of your life, it’s about putting the why at the center of your wealth.
Marc Killian 01:29
Yeah, well, and talking about money sometimes just makes people look. Even people that say, “I know I got to see an advisor, they come in, they’re doing the initial consultation, but they’re still a little closed off about truly opening up about money, I get it. It’s tough. So these are some fun things to think about. Maybe Jude, you look at a prospect across the table and you say, “All right, I got one for you. Picture yourself. You’re retired. It’s 1045 on a Tuesday morning. What are you doing, right? Because I think a lot of times what we do is we go, “Oh, I can’t wait to get to retirement, and every day is going to be a commercial. I’m going to be on the boat, or I’m going to be fishing. I’m going to be golfing, and I’m going to be playing with the grandkids in Disney World. Well, there’s also just random Tuesday mornings at 1045 where you don’t have anything to do. Not saying you got to plan every day here, Jude, but sometimes I think people just don’t think they don’t think about the the day to day of retirement, and it’s a new animal coming your way.
Jude Wilson 02:22
Well, it goes back to what we were saying about the why at the center of your wealth, and this question I like particularly because when we break down the why at the center of your wealth, we break it into three different components. What are the experiences you want to have while you’re in retirement? You know, you’re right. There’s only so much golf you can play now. Some of my golfer friends may disagree with me.
Marc Killian 02:44
They will be very upset with you. Yes, yes.
Jude Wilson 02:47
You know what are the experiences you want to have? What are the comfort items that you just want to buy because you want to buy it? You know that second home or the the most expensive car you’ve ever owned, and then what is the significance that you want to have in your life now while you’re living, and the legacy you want to leave behind? So when when I ask that question about, hey, it’s 1045, what are you doing? It’s really to get the clients to think, how am I going to transition into really fully enjoying this retirement? Because you know we do all the math and all the problem solving and all the strategies. That’s one thing, and and that’s important. But the other thing to have a real fulfilling retirement, we’ve got to ask a question like this, and and and have you what we call at the firm? Let’s have a dream session. So yeah,
Marc Killian 03:46
okay, okay. So
Jude Wilson 03:46
that that that’s one of my favorite questions because it really gets people thinking. Okay, yeah, what am I doing at that time?
Marc Killian 03:53
Yeah, yeah, exactly. Because you’re you’re trying to get past the abstract, like I said, of just the the big ticket items, and really start thinking about you know, there’s just regular life sometimes too, and even in the what you know what we hope is going to be an awesome retirement, there’s still just regular life as well. All right, number two, Jude, and you’re the Roth guy, but what if you were a financial genie and you said to a client, “Hey, look, if I was a financial genie, what three money problems would you wish for me to solve for you, right? And maybe that gets them talking about, okay, this specific thing here really worries me. Maybe they weren’t quite being as upfront in internet consultation as you’d like them to be. So you phrase it this way, and they go, “Well, I really wish we could fix X, Y, or Z. I
Jude Wilson 04:36
tell you the top ones I hear in this question. One, yeah, how can I make sure and never have to worry about income again for the rest of my life? And that’s more going back into the strategy, but it still is a good question because it gets them to thinking about what their true concern is. The next one that I hear is, you know, how can I make sure that if I predecease my spouse? He or she is going to be okay, and then the third one that I that I hear is, look, when I am no longer as independent as I am now, I want to know what’s going to happen. I want to. I most people tell me nowadays. I used to ask, well, what does that look like? Are you in an assisted living facility? Are you living with with your children? What does that look like? And I tell you, the answer has changed over the last 10 years. I hear more people say, “I want to have care at home. I don’t want to go to assisted living community. I want to be taken care of in the home that I’ve lived in, and so it’s it. And you hear so many great stories of people that say, you know, when my mom was going through this, what we had to do. This is a really deep question.
Marc Killian 05:52
Yeah, and I, you know, again, you’re thinking about the fact that you know you’re going to be hung up on money, right? So it’s like, you know, okay, if you are, then let’s find those things that really, really stress you out. That’s you know, it’s just another way of thinking about that sleep at night conversation. What do you need to tackle that helps you sleep at night? And this one’s kind of similar, but a little bit different. If you if you back away for just a second, Jude. So trying to separate, you know, folks, when you’re listening to this and we’re and you’re checking out Jude and I talking, what you do for income and what you’d actually like to do, right? Especially in retirement. So this question kind of goes to the look: if you had all the money you needed for retirement and you didn’t have to worry about that, but the only requirement was you had to get up each day and chase something or do something that you had passion for, what would that be? So this is that retiring to something conversation.
Jude Wilson 06:42
Yeah, and this is the one that goes back to our three categories. A lot of times, this is about experiences. I’ve heard great answers to this question. Well, you know, when I was a teenager, I used to play the guitar, and then you know, life got in the way, and and I I just haven’t picked up a guitar in 30. I’d love to take
Marc Killian 07:03
lessons again, right? Yeah. Yeah.
Jude Wilson 07:05
Or you know, one of the things that I’m really passionate about is you know I’ve worked for 40 years and I was really good at what I was doing, but the next generation there’s a there’s a knowledge gap in my industry, yeah, and I and I I want to help the next generation do as well as I did. The answers that I get when I hear this, no two answers are ever the same, but you can start to see the real passion in people. What’s really important to them when you ask this question?
Marc Killian 07:38
There you go. I like it, and and that’s really what you’re trying to do. You’re trying to come at this from just a different. So tell me what you want, mr. mrs. Jones. Tell me what’s you know instead of that kind of cliche kind of thing. Sometimes we want to get a little you know deeper in there and maybe think about things in a different way. Number four, knowing what you know now, and I know you asked this question pretty closely. What would you like to have done differently financially, or what would you have done differently financially? And usually, the top answers are like, “I would have saw an advisor sooner. I would have asked about the Roth sooner. You know,
Jude Wilson 08:10
you hit it. Number one, I get from every almost every client that I talk to is, “I I wish I had started sooner, or you know, I wish I had you know gotten some advice sooner, and it cuts across all financial spectrums. I mean, some of my most affluent multi-multi millionaire clients to you know the regular teacher that just retired with a pension, they all seem to ask that have that that that in the back of their mind, and for us, it’s almost like being financial psychiatrist at that point. Because
Marc Killian 08:48
yeah, and it’s not just the regret. Like, let’s not like, hey, I want you to share all your regrets. It’s just saying, you know, what what would you like to have done differently, and then how can we kind of learn from that, right? Yeah, that we’re not making similar mistakes.
Jude Wilson 09:01
Well, I once we get through the strategy part, and we’re able to help clients see that you’re going to have the income to live the lifestyle that you’ve become accustomed to, and we’re going to ask you a question every year-one simple question: How’s your income? Because once you figure that out, there’s no use in looking in the past to what you would you have done differently back then. We’re in the present now, and we’re looking toward the future. And if we could check that box off that you have the income that you want, and we can check off some of those financial concerns that we talked previously about, then let’s just enjoy your life.
Marc Killian 09:40
Yeah, then Bob’s your uncle, as the saying goes. Then you’ve knocked, you’ve checked it off, and you’re, you you know, got it done. Yep. All right, fifth one here, last one. Everybody’s got a bucket list. Typically, when they come in to see a financial advisor, for sure, they’re sitting at home making up. You know, we all kind of have them at different stages in life, but certainly when you get close to retirement. So let’s just reframe. That just a little bit, and just say, okay, cool. Let’s say mr. mrs. Jones or mr. mrs. Smith or whoever walk in the door, and they’ve got 20 items on a bucket list. Well, now let’s look at those 20, and let’s break them down to what do you want to tackle in the first five years, right? Or what do you want to tackle in the second five years? Because the reality is, a the money, sure, but B, what’s your body gonna let you do, right? So, if on that list of 20 things you’ve got some items that you know that maybe don’t require a lot of physical stuff, maybe those get pushed down to a little bit later, and you know, you know, walking all around Europe gets moved to the top of the list while you still can do
Jude Wilson 10:40
- 100% and the way that we strategize this for clients is we kind of break down your retirement life in three phases. You’ve got your go-go years, yippee! I’ll have to punch a clock. I don’t have to answer another email, and you want to go out and take that Viking cruise, or or you know visit Rome and do all of the walking, and then there’s the slow-go years where you’re you’re kind of pulling back a little bit. You know, you’re just kind of chilling, and then the the no-go years where we’ve got to really plan on you know your care and making sure that you can live independently, even if you’re not as independent as an individual as you used to be, and so crossing off that bucket list is really important because you’ve got to have the resources to do those things and prioritizing. So sometimes when I ask this to clients, they they look at me kind of weird because I thought I came to talk to you about Roth conversions. What are we talking about this this bucket list, but that’s just one part of the puzzle. To really have that fulfilling rest of your life, I want you to enjoy as much of that bucket list as you can. Yeah,
Marc Killian 11:52
it’s just trying to reframe the the priority questions, timeline questions, trade offs. Obviously, the money has to be part of these conversations as well, but they are the tool. They’re still it’s still about the items that are on the bucket list or on the wish list or on the you know who am I kind of list, and that’s tough for people to get into sometimes. So maybe kind of coming at this at a different angle helps.
Jude Wilson 12:16
And and and the last point that I’ll make about this is that for most of the baby boomers that I know, and and some Gen Xers like us, they’ve been just saving all of their life, and that has been the number one priority. So it’s kind of hard to turn that switch and say I’m going to go from saving to spending. Yeah, and and it’s a it’s part of the psychology of financial planning. You know, I see a lot of firms that are actually very good at the X’s and O’s piece. You know, how much should we invest here? You know, how much should be in in bonds versus how much should be in equities? But to me, a completely holistic financial plan includes these questions because it’s not about how many dead presidents that you have. It’s really about looking at how do we use those resources to make this the best quarter of your life.
Marc Killian 13:16
Yeah, I mean the Benjamins are important, you know, as Ice Cube and made his movie. It’s all about the Benjamins a while back, but they’re just a tool, like I said earlier, right? And so you need some guidance. You need some planning. I mean, that’s what the GPS is all about, right? It’s that guidance planning solution. So 100%
Jude Wilson 13:33
I like how you put that in there exactly right.
Marc Killian 13:35
I’ll tweak that in. So look, at the end of the day, just think about questions in a different way from retirement, other than what do I got? Will it last as long as I do? I want to take six trips with the grandkids. Yeah, all that stuff’s important, right? But we ask it in the same way over and over again, and sometimes it starts to kind of fall on deaf ears. So reframe those questions a little bit: how you want to think about retirement, what you need. Go see an advisor. Go talk to two or three. Find the one that talks to you in a way that relates to you, that makes sense to you, that maybe even thinks outside the box a little bit. And of course, as always, if you need help, reach out to Jude and the team. But you know, before you take any action with anything, again, talk with a few people, find the right fit for you, and then see how it affects you know your specific life and your specific situation. And that’s what Jude and his team do really well with their GPS system. So reach out to them, get started today. 800-779-4592. It’s on the screen. It’s on down in the show links below, along with the links to click onto the website and get started that way as well, and lots of other good tools, tips, and resources that you can find. So with that, we’ll say thank you very much for hanging out with us. This is the Roth guy. He’s the Roth guy. Subscribe to us on Apple, Spotify, and YouTube. And my friend, thanks for hanging out.
Jude Wilson 14:45
Hey, don’t forget to put the Y at the center of your wealth.
Marc Killian 14:48
There you go. And we’ll see you next time right here on the Roth Guy.
Speaker 1 14:56
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