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These 5 Questions Reveal A Lot About Your Financial Plan

Financial Symphony / John Stillman
The Truth Network Radio
October 2, 2026 4:00 am

These 5 Questions Reveal A Lot About Your Financial Plan

Financial Symphony / John Stillman

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October 2, 2026 4:00 am

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446   Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Jake 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 what we discuss in this episode:   🧞 Financial Constraints: Identify worries holding you back ❤️ Purpose: Define what matters beyond money 🔙 Past Regrets: Learn from previous financial choices 🧠 Money Mindset: Recognize habits shaping retirement decisions 🪣 Bucket List: Turn future dreams into goals 📅 Retirement Stages: Plan around changing life seasons   Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

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Talking about money is hard for some people, and sometimes it just takes the right questions to get things rolling. Here are five questions that can reveal a lot about your retirement plan. Hello and welcome in. I am Ben George with Jake Dozer of Rosewood Wealth Management. Today we got five questions that are going to tell you a lot about kind of where you stand with your financial plan.

A lot of people kind of wonder, "Hey, am I in good spot? Am I on the right track? Should I be doing things differently?" Well, today's questions will help you kind of answer some of those things.

So let's jump right in, Jake. I'm going to start with this first one.

So I'm going to give you the question. You kind of tell us, you know, what this answer is going to reveal for a certain person.

So, yeah. Here's the first one. Picture yourself retired. It's ten forty-five on a Tuesday. What are you doing?

And I mean, ten forty-five in the morning on a Tuesday.

So, what are you up to?

So, what is that question going to tell us?

Well, look, if it's ten forty-five on a Tuesday night and you want to talk about that too, by all means, I'm sleeping at ten.

Well, I'm either sleeping or feeding my three-month-old baby at ten forty-five. There you go. But I love this question because the goal of these questions is to peel back the onion and recognize first and foremost, retirement is not just "I'm done working." You know. If your mindset is I want to retire, and you're exhausted from work, that's fine. But understand, you're not retiring from from something alone.

You're retiring to something as well.

So the question is: Is what are you going to be doing at Tuesday at ten forty-five? Meaning, what is life going to look like for you in retirement? Because it needs to look very different than what it did before. But there needs to be purpose assigned to it. I just got a text from a client this morning who was laid off.

And it was actually an answer to prayer because he was kind of hoping to get laid off because he wanted to retire this year and was hoping.

Well, if I get laid off in this round of layoffs, I could end up with severance and actually get paid for longer than my employment had. I give a notice, and so it was. It was kind of like we were. You know, silver lining, hoping it would happen, but also there's an element of the emotionally didn't want it to happen. But I loved what his mindset was, which was like, you know, how do I make lemonade out of lemons?

But then also, what am I retiring to? Because he has got grand designs of what him and his wife's retirement are going to look like.

So it's so much easier to start with having a vision for what you want your retirement to look like, so that you can then work back. Into what should my retirement plan be built around, as opposed to what a lot of folks do, which is like, well, I've got this portfolio of money, and you know, I might not say it out loud, but I'm afraid to spend it because I'm afraid of the taxes, and what if I spend too much? Because I don't know how much I can afford to spend, and can I really afford to live the lifestyle I want? And you're always making these second-guess, anxious decisions, as opposed to having a clear vision of what you want to accomplish. Then.

Aligning your investment and overall retirement plan towards that vision, so that you can have freedom and peace of mind and confidence to live the retirement lifestyle that you have clearly mapped out, even though it can change, because you've planned for it, not because you're stumbling in and through it.

So much better. Yeah, know what you're retiring to. That's kind of the whole point of that question. All right, right. Second one here.

So if if I was a financial genie, what are three money problems that I would wish to have?

Solve so, obviously these are things are going to be keeping you up quite a bit here, and that's a good way to kind of address what's really kind of hanging over you in the back of your mind. Yeah, I mean this is a similar question to what a lot of business owners and managers go through. It's a thought process of if I did not have constraints, what would I want to happen in a perfect and ideal world? And what it allows you to do is think beyond our constraints. A lot of times we think, well, I'd like to do this, but perfect example.

I met with some folks that are very close to us. He said, "We we need to stop spending the amount per month. We need to scale back." And I said, "Well, what makes you say that?" They're my clients. I know where I'm going with this. You know, in my mind.

And they said, "Well, you know, it's intimidating." And I said, "Whoa, whoa, whoa! You haven't first asked yourself, 'Can I afford to spend what I'm spending monthly?'" Because if you knew that answer, then you could make an informed decision of do I need to slow my spending down, as opposed to the fear leading you to believe you need to slow your spending down, and the guilt associated with that spending.

So similarly, if you're thinking about your retirement, think: Let's take everything off the table. What is my dream retirement? Then let's shape the planning we do around that dream. Because a, it's likely that you are underestimating the capacity that you have to spend. Most folks come in, and unless they've woefully been unprepared, they probably can afford to spend more than they think they could.

But they need to take the blinders off and first start with again. A vision of what they want before they do the planning. Don't allow the plan or the investments you've chosen to dictate how you live your life. Request that the investments serve how you want to live your life. That's the right order of operations.

All right, that's a good question and something to really think through. Third one here, Jake, is if I gave you all the money that you thought you could ever possibly need. The only thing I want to ask, though, in exchange for that, is that you actually get up every day and do something that you're very passionate about. What would that one thing be?

So I guess remove the whole financial element of what's driving you and motivating you. Right. What are you left with? What do you care about? You know, that's really what it boils down to.

Is what is your identity? You know, this is a great litmus test. To help you understand the difference between what you do for work and money, and what you care about, you know what's that old adage? I'm probably going to butcher it, but it's if you love what you do, you never work a day in your life. And not all of us have the benefit and the luxury of of getting that.

I realize that that's unrealistic for everyone to to do, but it's a certainly a worthwhile exercise to aspire to. And it doesn't just stop with your career; it should also translate to your retirement life. And so it really. Speaks to that again—that part of what is my identity, where am I drawing my value and my purpose from? For me, it's my family.

For me, it's my my faith. For you, it could be your community. It could be giving back and volunteering. Whatever it may be, there's going to be something that you need to occupy that 10:45 a.m. slot on Tuesday, like we mentioned earlier.

And you have to ask yourself, outside of just the work, outside of being a slave to the dollar, what do I care about? Gets me up every morning, and what causes and people are the motivators in my life because that's what's going to occupy your time once the nine to five ain't there anymore. All right, here's one that I think maybe would. We think people are a little curious. Why are we asking this question, Jake?

So, knowing what you know now, what would you have done differently financially?

So, what are we trying to figure out with that question? Ooh, that's a great question, and it's a question I particularly enjoy talking about in the line of like thinking about generational wealth and thinking about family. What this question does is it opens the doors to identifying regrets and lessons that we might. That folks might not be as comfortable bringing up with us unless we prompt it. Why does this help us?

Because a lot of times we enable what are like these biases in our lives, and I don't necessarily mean that in the twenty twenty twenty six context of like bias against a person, but rather things that sort of are defaults in our mind that steer us one direction or another. You know, if you walk into a restaurant and you were told nothing but bad things about it. You're probably not going to love the experience because you're going to be jaded in your mind. Similarly, if somebody, your best friend, comes in and hypes up this movie, I've got a friend whose favorite movie is Top Gun Maverick, and he cannot do anything but like proselytize about this movie to the point where I'm like, "It's a good movie, but is it the best movie?" I don't know if it's anyone's best movie, you know.

So here's the thing: is I can't in my mind get around thinking it's the best movie ever because. He's so incessant about thinking it's the best movie ever.

Now take that concept and apply it to the past regrets and the way you think about money and approach it. That may unconsciously steer you one direction or the other. The person that spends their whole career save, save, save, always being so frugal, maybe growing up the child or grandchild of depression era people, that probably results in being good frugal savers but awful spenders in retirement.

Well, that's a good problem, but it's a problem nevertheless. Because you built this money up, and now you don't know what to do with it or how to give yourself permission to use it, right?

So, until you identify the challenges that will stop you from living the lifestyle you want in retirement, you have to you have to identify those so that you can move forward and grow past them, and it'll help you enjoy retirement and detach yourself from maybe the feelings of guilt or or you know the militant mindset. Mindset about saving or whatever it may be.

So, if you want to get into retirement and not only enjoy the lifestyle you want, but also enjoy peace of mind while doing it, you're going to have to address some of those skeletons in the closet, some of those biases that live there. I one last question here that's going to tell you about your financial kind of where you stand, but it's not really a money question, right? What do you want to cross off your bucket list in the next ten years to look back and really feel like you've accomplished something?

So, again, a great question here, Jay, kind of setting you up for that next chapter of life. You know, I don't know anyone who. Is on their deathbed and thinks, you know, I really just did too much good stuff in retirement. That's just not a concern people have, but plenty of people have regrets. Like the previous question we talked about, plenty of people wish they would have enjoyed time with their family more.

They would have given to their kids and grandkids more. They would have spent more time volunteering and less time worrying. That's because a lot of times it's really hard for us to set goals and quantify them. You know, life we can allow we we can either live our life. Or alive, let our life live us, you know.

In in in reality, when you're thinking about retirement, retirement is often a 20 to 30 year process, but it's broken into kind of three stages: the go go years, the slow go years, and the no go years. You don't want to be entering the no go years, wishing you could get back to the go go years because you forgot to do, maybe not forgot, but you chose or felt like you couldn't because of a lack of clarity. Do what you wanted to, so. Identifying those bucket list items forces you to start planning for them. It forces you to take these like concepts and and put a task to them and put a budget and allows you to put pen to pad and actually plan for them as opposed to thinking about maybe a one day.

But it takes your dreams and makes them a plan because until you have a plan for the different components of retirement, you have a retirement dream, not a retirement plan. And so start. Creating accountability in your life in the best way possible, so that you can enjoy the retirement that you deserve.

Well, all of these questions, Jake. But how do you actually take these and apply this to how you're helping someone plan at Rosewood Wealth Management? What do these What do these questions actually change about the the way that you look and address someone's situation? It all comes down to what's our mindset and what is the relationship that you're looking to have with a financial planner or a professional of any sort in your life. You know.

Do you want your relationship to be? Here's an example. I'm going to get a haircut in two days. When I walk into that barber shop, I'd like to be able to say, "Here's what I want to accomplish." You make all the decisions. You're the barber, not me.

When I walk into an attorney's office, I don't want to say, "I want a will." I want to this type of trust, and I'd like this, and I'd like boom, boom, boom. You just print that for me. No, I want to go in and say these are my concerns and my fears. What documents do I need to address those? Right.

So similarly, our role as financial planners, specific specializing in retirement planning, is not well. You come in and tell me what you want, and I'll give you the tool to do there. No, no, no. That's that's totally eliminating any expertise and experience that we can bring to the table. Our role is to say, help us.

Let's dream forward together. If let's describe this ideal retirement. Let's talk about your hopes and fears, and then let's plan to address those things as opposed to just throwing. A handful of products on the shelf at the problems in a bunch of jargon, so it allows us to really shape your priorities, your timelines, and the trade-offs. If if you want this, you're going to have to give up that or that or vice versa, as opposed to you filling out some sort of financial inventory or form alone.

That's just you're missing the forest for the trees there. Yeah.

Well, none of these questions are about money, and that's really kind of the point, right? A good conversation about your financial status and your financial. Future starts somewhere entirely many times, and that's what happens oftentimes at Rosewood Wealth Management as they address your concerns, fears, goals, and help start looking at what's going to take to get you there down the road.

So, reach out if you have questions, you want to begin that planning process, or hey, address something that we discussed here today in this video. But we also ask that you subscribe if you enjoyed this content, as well more coming pretty soon with Jake and also John as well.

So, we'll talk to you again at that point. Take care. Carolina Wealth Strategies, doing business as Rosewood Wealth Management, is a registered investment advisor in the state of North Carolina. The material presented is intended to be general information and should not be construed by any consumer as the rendering of personalized investment advice.

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