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One of the most important lessons I've ever learned about financial planning actually came from a children's story we all know. Shel Silverstein. He wrote the book the Giving Tree, a book beloved by many. He also wrote a poem called Smart. I'm going to read this poem to you and I'm going to show you how One of the most important lessons you can learn or you can realize about financial planning comes straight from this poem. It goes like, My dad gave me $1 bill because I'm his smartest son. And I swapped it for two shiny quarters because two is more than one. And then I took the quarters and traded them to Lugh for three dimes. I guess he didn't know that three is more than two. Just then along came old blind Bates. And just cause he can't see, he gave me four nickels for my three dimes and four is more than three. And then I took the nickels to Hiram Coombs down at the seed feed store. And the fool gave me five pennies for them and five is more than four. And then I went and showed my dad and he got red in the cheeks and closed his eyes and shook his head, too proud of me to speak now. It's a cute poem. It's a fun poem. We read this and this little boy of course doesn't understand that value doesn't come from the amount of something. It comes from the intrinsic worth of something. Now we read that and think, how cute. But that boy is all of us. That boy in his mind is trading for more of something. For more of something that he perceives to be valuable. And what he perceives to be valuable is simply that it's more. What he doesn't realize is the intrinsic value of what he's trading is worth less and less every single time that he does it. So here's the planning application for all of us as we approach our retirement years. We're typically in our higher income earning years. We're typically at that point where we're making meaningful progress in terms of increasing our portfolio balance. Increase in our net worth, increasing that thing that we perceive to be most valuable. And that thing is very valuable, that portfolio, that income. That's what enables us to do the things that we want to do. But here's the pitfall I see far too many people fall into. They get to that point where they've reached the point at which they could be financially independent. Yet they keep working. And what they end up doing is they end up trading things that are more Valuable for things that are less valuable. And what I mean by that is every single year you keep working, every dollar you keep saving after the point of financial independence. In many cases this isn't always, but in many cases, you're trading something far more valuable to get that. You're trading your time, you're trading your health, you're trading your ability to pour into the relationships that you have. Now, I know these aren't necessarily mutually exclusive, but I've seen time and time and time again people who, once they are in those ending stages, those latter stages of their working years, it's so difficult for them to step away. They're earning a lot, they're paying more into Social Security, they're maxing out their 401k. It's difficult to get out of that. And just to be clear, you probably shouldn't get out of that if you're not yet financially independent, if you don't yet have enough of a portfolio to support what you want to do in your retirement years. But just like that, boy, we trade these things. Time, health, relationships. These things that the older we get, the more valuable they become. We're not guaranteed health for the rest of our life. Let's not trade it away. We're not guaranteed any amount of time at any point in our lives, but certainly the older we get, the less and less time we have left remaining on this earth. What about those relationships? What about those experiences, these things that by nature, the older we get, the less and less and less of them we're going to have, and the less of them that we're going to have, the more valuable they become. We trade those in exchange for dollars. Like this little boy who goes from $1 to 2/4 to 3 dimes, to 4 nickels, to 5 pennies, so proud of himself for what he did. That's us. We continue to build. We continue to get more of something that is increasingly less value over time. And we exchange the thing that's a true value. So what can we do to prevent that? Well, number one, create a financial plan. The reason you plan is, yes, to optimize the financial resources that you have. This is everything to do from your investments to your tax strategy, to your estate plan, to your retirement strategy, your withdrawal rate. All these things should be optimized with the right financial strategy. But if that's all you're doing, you're missing the bigger picture. Don't just optimize them. Optimize them so they can fully support the life that you want to live. You can do the things that you want to do. You can prioritize your health, your relationships, your travel, your adventure, whatever a beautiful life looks like for you, do that now. If you're that person who's maybe watched dozens of these videos, hundreds of these videos, and you still don't feel totally confident in your financial plan, reach out to us at Root. We are financial advisors. This is exactly what we do for our clients all day, every day. If you're not ready to work the financial advisor, click on the link below. The Retirement Planning Academy. It's your chance. It's a guided process to help you create your own financial plan. And it comes with some of the software that we actually use for our clients here at Root. But whatever you do, if you don't already have a financial plan, create one. A financial plan is going to give you that sense. It's going to give you that clarity. You need to understand, can I actually step away? When is that time? If it's not now, what can retirement look like? And once you have that framework, then you can answer the bigger questions of what do you want to do with your life? What do you want to do to ensure that your retirement is as meaningful and as special as it possibly can be? And then the second thing you can do is identify what you really treasure, what you really value. Now, really, this should be step one, because a financial plan should be constructed around those things that you value and that you treasure. That being said, sometimes it's easier to start with a financial plan. You have no idea what you can even dream about. You have no idea, can I dream big? What do I need to do? What does retirement potentially look like? And sometimes a financial strategy gives you some clarity. It helps you understand this is what you can realistically spend without running out of money. It does help you to understand those things. And then you can work backwards and understanding what do I want things to look like between myself and my spouse? If I'm married, with my children, with my friends, with my community, with my health, with my sense of adventure, activities, hobbies, whatever it is, this should be a reflection of what's most important to you. The goal is to be able to look back on your life one day and not say that you accumulated tons and tons and tons of pennies like this little boy did. But you had what really mattered. You had that true value. And your financial plan should not exist in isolation. Your financial plan should exist to support that vision. So when you can have a very clear understanding of what it is you want to do, and why it's important to you and what that looks like for you to pursue it. The financial plan is one of the most powerful things you can do to actually enable that lifestyle. So as we look back on this story, don't just look at this story and think of the cute little boy who had no idea where value really lied. Look at that little boy and say, how can I learn from him? How can I not be him? So that I can ensure that I'm pursuing the things that are actually valuable, not just the things that are more, not just the things that are easy to track and keep score of, such as a larger and larger portfolio balance. Once again, I'm James Knoll, founder of Root Financial, and if you're interested in seeing how we help our clients at Root Financial get the most out of life with their money, be sure to Visit us at www.rootfinancialpartners.com.
Podcast Summary: Ready For Retirement – Episode: "The #1 Way to Ruin Your Retirement (Most People Do This)"
Host: James Conole, CFP®
Release Date: July 29, 2025
In the episode titled "The #1 Way to Ruin Your Retirement (Most People Do This)", James Conole delves into a common yet often overlooked mistake that many individuals make while planning for retirement. Through engaging storytelling and insightful financial analysis, Conole highlights the importance of understanding true value versus perceived value in the context of retirement planning.
[00:00]
Conole begins by referencing Shel Silverstein’s poem, "Smart," to illustrate a fundamental lesson in financial planning. He reads the poem aloud:
"My dad gave me $1 bill because I'm his smartest son.
And I swapped it for two shiny quarters because two is more than one.
And then I took the quarters and traded them to Lugh for three dimes.
I guess he didn't know that three is more than two.
Just then along came old blind Bates.
And just cause he can't see, he gave me four nickels for my three dimes
And four is more than three.
And then I took the nickels to Hiram Coombs down at the seed feed store.
And the fool gave me five pennies for them
And five is more than four.
So proud of himself for what he did."
[02:15]
Conole explains the moral of the poem:
"The boy doesn't understand that value doesn't come from the amount of something. It comes from the intrinsic worth of something."
This narrative serves as a metaphor for how individuals often prioritize increasing their financial assets without recognizing the diminishing returns and the true value of non-monetary aspects of life.
[03:40]
Transitioning from the poem, Conole identifies a prevalent pitfall among those approaching retirement:
"They reach a point where they could be financially independent, yet they keep working."
He emphasizes that continuing to work beyond financial independence often leads to trading invaluable personal aspects—such as time, health, and relationships—for financial gain. This mirrors the boy's futile trades in the poem, where each subsequent trade diminishes the actual value received.
[04:25]
Conole elaborates on what people are trading when they continue to work past financial independence:
He warns that these sacrifices often go unnoticed until it's too late, leaving retirees with significant regrets despite having substantial financial resources.
[05:10]
To avoid these pitfalls, Conole advocates for creating a robust financial plan. He outlines the key components:
Optimize Financial Resources:
"Optimize everything from your investments to your tax strategy, to your estate plan, to your retirement strategy, your withdrawal rate."
A well-structured financial plan ensures that your monetary resources are managed efficiently.
Support Your Desired Lifestyle:
"Optimize them so they can fully support the life that you want to live."
Financial planning should enable you to prioritize what truly matters, such as health, relationships, travel, and personal fulfillment.
[06:45]
Conole stresses that a financial plan should not exist in isolation but should be intertwined with your personal values and life goals. By doing so, you ensure that your financial decisions enhance, rather than detract from, your overall quality of life.
[07:20]
The next step, according to Conole, is to identify what you truly treasure and value. He suggests:
[08:00]
Conole offers practical advice for those unsure of their values:
"Sometimes a financial strategy gives you some clarity. It helps you understand this is what you can realistically spend without running out of money."
This approach allows individuals to dream big and understand the financial feasibility of their aspirations, thereby creating a harmonious balance between financial security and personal fulfillment.
[09:10]
Conole encourages listeners to take proactive steps towards financial planning:
Engage with a Financial Advisor:
"If you don't feel totally confident in your financial plan, reach out to us at Root."
Use the Retirement Planning Academy:
"It's your chance. It's a guided process to help you create your own financial plan. And it comes with some of the software that we actually use for our clients here at Root."
These resources are designed to help individuals create comprehensive financial plans that reflect their personal values and life goals.
[10:30]
Conole wraps up by reiterating the primary lesson from the "Smart" poem:
"Look at that little boy and say, how can I learn from him? How can I not be him? So that I can ensure that I'm pursuing the things that are actually valuable, not just the things that are more."
The episode emphasizes the importance of balancing financial growth with the preservation of personal well-being and relationships. By avoiding the pitfall of endless financial accumulation, retirees can achieve a more meaningful and fulfilling retirement.
Final Thoughts
James Conole’s insightful discussion in this episode serves as a crucial reminder that retirement planning is not just about amassing wealth but about creating a life that aligns with one’s true values and desires. By crafting a thoughtful financial plan and prioritizing what truly matters, individuals can avoid the common mistake of trading invaluable personal aspects for financial gain, ensuring a secure and fulfilling retirement.
For more information and to access the Retirement Planning Academy, visit www.rootfinancialpartners.com.