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Most people watching this video think retirement is all about the numbers. How much have you saved? Can your portfolio withstand the next downturn? Do you have the right tax strategy in place? And while all those things are important, if that's all you're focused on, you're really going to struggle when it actually comes time to retire. But here's the truth that no one actually talks about. The number one reason people struggle in retirement actually has nothing to do with money. And while money can be a supporting factor here, the number one reason people struggle is they don't actually know what they want their life to look like. And if you don't actually know what you want your life to look like, then no amount of money doesn't matter what your financial strategy is. Nothing can replace that in terms of giving you the type of retirement that you're looking to live in. One of his blog posts, Morgan Housel had this to say. He said, if you have no strong views on what kind of life you want to live, who you are, what you desire, what makes you happy and what doesn't, you're likely to want to mimic the most visually appealing person you come across, which is often the person with the biggest house, fastest car, or, or nicest clothes. That may work, it may not. We see this all the time. We have goals for retirement. We know that by a certain age we should retire. We know we should max out our 401k. We know what to do to optimize Social Security. And then we get there and we freeze. And we freeze because we think, what am I actually going to do? The past 30 years, the past 40 years, all I've been doing is working and grinding and raising a family and doing all these things that matter. But I've lost this sense of who I am and what I want to do. So when I set goals for my retirement, it's not actually my goals. I don't even know what my goals are. I'm just going to mimic what I see other people doing. They must be happy, right? They have the nice cars, they take the nice trips. They do the things that seem to make them happy. Maybe that's what I want for my retirement. But if that's the way that you're approaching it, you're going to be let down. You're going to retire. You might enjoy it for a short, brief period of time, but then you're going to feel this sense of loss. Why? Because. Because your job was your identity. Your job was your structure. Your job was your social connection. Your job was this thing that even if you didn't absolutely love it, provided these things that all of us need, provided this purpose that gave you this sense of identity. And then one day, just like that, all that changes. You now have the money. You now have the time. You've retired from that. But what have you retired into? And that's what I want to address today. How do you avoid that scenario where, even if you have the best financial strategy in the world, you may have a very tough retirement if you don't address these questions first? So what do you do? Well, if it's not about looking at other people's homes, other people's golf trips, other people's idea of what a good retirement looks like for them, what should you be doing? What you do is you start with clarity, not money. So here's a relatively simple framework for that. Instead of thinking, what do I want to do with my retirement? That's an enormous question that's going to cause a lot of anxiety just thinking about that. Think about what do you want each of these components or each section of your life to look like? What would you want your relationships to look like? Who are you spending time with? Who's most important to you? Think about that. What about your health? What does that look like? What about hobbies? What about faith? What about travel? What about giving back? What about all these things? Doesn't have to be super complicated, but if you can identify, these are the things that actually matter most to me. Not what my neighbor's doing, not what my old coworker's doing. But these things bring me joy. These things bring me a sense of purpose. Write down one or two, maybe three things for each of those, and then simply say, how can I prioritize that? Imagine you're retired today and it's a Tuesday morning. Not a weekend, not an extravagant trip. It's a Tuesday morning. What are you doing with each of those things? You don't have to do all of them in one day, but what can you do to prioritize your relationships, purpose, hobbies, adventure, whatever that might be? Sit with that and think about it. For as much time as we spend on the financial side of things, can you spend just a little bit of time with this? Who are you and what do you want to do? If you want a fun thought exercise that goes along with this, let's explore this. You get $25,000 in your bank account today under one condition. You have to have spent it within the next seven days. Anything you spend it gets taken back and spending does not mean saving it or investing or even paying down debt. Spending it means what are the things you would actually spend that money on, what comes to mind. It's a good exercise to go through, help you understand what do you actually care about, not just indefinitely saving something for the future, but what would you spend money on today if you were forced to spend it? Because it would be taken back if you didn't, Then once you have some of those things in place, then you can plan backwards. If your idea of a wonderful retirement is four luxury vacations a year all across the world, that's going to be a very different financial strategy than someone who also wants to take a lot of trips. But their idea of a fun trip is driving to the mountains for a long weekend and spending that hiking and backpacking. So what matters to you? Don't just say travel, what type of travel? Don't just say relationships. What would you be doing? What types of relationships? Don't just say hobbies, what specific hobbies. Because once you have that clarity, once you know what your life is going to look like, then you can design the financial strategies to support that. A financial plan without a corresponding life plan is somewhat meaningless. At the end of the day, it's not going to matter how much you have in your 401k when you collect Social Security, how much you save in taxes through the right withdrawal strategy. If you don't have a bigger purpose that it's connected to, you're not going to have the impactful type of retirement that you should have. So if you're struggling with this, reach out to us. This is exactly what we do here at Root Financial. Not just a financial piece, but helping to connect that financial piece, helping to be a thought partner, a thought leader with you to say, what can life look like? What, what does this look like? If I get out of the rut that I've been in for the past 30, 40 years, which, by the way, is not a bad thing. That's just life. Life sometimes takes us on this journey of. Over the course of our careers, we do less and less of what we think we want to do. And we look back one day and say, I'm 55, I'm 60, I'm 65. And those things I used to enjoy, I don't do any of it anymore. I've been so focused on career and responsibilities and preparing that I've lost sight of that. How can you get to this point where you start to have a vision for what retirement can look like and then take the necessary steps financially to move in that direction. But here's the bottom line. Retirement should not be the end of your story. Retirement should be the very beginning. Retirement can be scary. It can be overwhelming, because you have to think of those bigger questions. What will you actually do when you have the time, the resources, the freedom to be whatever you want to be? But if you can go through these exercises, if you can start to think about what actually matters most, think about what that practically looks like on a Tuesday morning in retirement, on a Thursday afternoon in retirement, and then work backwards to say, what financial moves should I make today to move in that direction, that is going to make all the difference. It.
Host: James Conole, CFP®
Date: September 15, 2025
In this episode, James Conole explores the deeper, often overlooked challenges people face in retirement—those unrelated to finances. Drawing from personal experience, client stories, and wisdom from thinkers like Morgan Housel, James argues that the true struggle in retirement comes when people don’t know what they want their life to look like after work ends. The episode provides frameworks and exercises designed to help listeners gain clarity on their non-financial goals, revealing why purpose and identity—not just planning and savings—are at the heart of a fulfilling retirement.
On the mistake of copying others’ retirements:
“If you don’t actually know what you want your life to look like, then no amount of money… nothing can replace that in terms of giving you the type of retirement that you’re looking to live in.”
– James Conole (00:34)
On the trap of comparison (Morgan Housel):
“You’re likely to want to mimic the most visually appealing person you come across, which is often the person with the biggest house, fastest car, or nicest clothes. That may work, it may not.”
– Quoted by James Conole (00:51)
On identity loss:
“Your job was this thing that even if you didn’t absolutely love it, provided these things that all of us need… Then one day, just like that, all that changes.”
– James Conole (02:11)
On financial plans serving a purpose:
“A financial plan without a corresponding life plan is somewhat meaningless.”
– James Conole (07:05)
On starting retirement fresh:
“Retirement should not be the end of your story. Retirement should be the very beginning.”
– James Conole (09:12)
James Conole’s central message is clear: Money alone doesn’t guarantee a happy or meaningful retirement. The real work is in defining what a good life looks like for you—and only then creating the strategy to support it. He encourages listeners to take practical steps toward envisioning their daily retired lives, stressing that clarity and purpose pave the way for decisions that will lead to satisfaction, fulfillment, and lasting peace of mind.
“If you can start to think about what actually matters most … and then work backwards … that is going to make all the difference.” (10:04)