Ready For Retirement

5 Signs It’s Time to Retire - Right Now

James Conole, CFP® Episode 297

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers.

Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly moving the goalpost while trading away your most vibrant, healthy years.

In this episode, we explore the critical difference between lifespan and healthspan. While many Americans live into their 80s or 90s, our healthiest years typically decline around age 66. Waiting too long to retire may leave you with more money, but fewer active years to travel, hike, or be present with grandchildren.

We also unpack the emotional side of retirement: the identity loss many face when stepping away from their career, and how this psychological barrier—paired with strained relationships from decades of overwork—can keep people stuck longer than they should be.

Retirement isn't just about having enough money. It's about having enough life left to enjoy it.


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The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Speaker 1:

Imagine real quick that you're 90 years old. You're looking back on your life and all that happened. Are you thinking about the final bonus that you had, or are you thinking back on the time that you didn't spend with loved ones? Far too often, the regrets people actually have have nothing to do with finances and how much money they didn't spend, the bonuses they didn't receive. They regret the things they didn't do with family, with loved ones, the activities that they wish they would have done more of. That's why the topic of today's video is five signs that it might be time for you to retire.

Speaker 1:

I'm a financial advisor that's worked with hundreds of people over the course of my career, so I know that financial readiness is the key. But there are also these overlooked reasons that people don't spend enough time thinking about when it comes to their retirement decision, and that's what I want to cover today. So let's go through the five reasons that might be time for you to retire now. And reason number one is time is the only non-renewable currency. What I mean by that is time is the only thing you can't get back. Theoretically, you can always make more money. It might get increasingly more difficult the older that you get, but you can always make more money. You can never make more time. When we're young, we really prioritize money because we think that time is endless and so we need to prioritize money building our money, saving our money because that creates the freedom to do the things we want to do. But as we start to get older, there comes a point where there's a crossover. Now, of course, none of us know how long we have, but at some point we need to start realizing that it's that time that's far more important than money.

Speaker 1:

What I see too often is people who think about retirement and all the wonderful things that it can bring. But there's so much in this mindset of I need to work, I can't pass up another bonus, I can't pass up another round of stock investing, so it's goalpost planning. They keep pushing back and pushing back and pushing back, thinking that at some point, one more bonus, one more portfolio milestone and they'll feel more confident to retire. That never comes, unfortunately. What does come is what comes is a sense of regret of people who push retirement to 65, then 67, then 70. And they realize that those are years of their life that they're never going to get back, and not just years of their life, but the healthiest years of their life, the years they could have spent traveling, the years they could have spent with family, with grandchildren, doing activities that they loved, and because they viewed money as a thing to get more of, not from a selfish mindset, not from a greedy mindset, just from the mindset. That's what they've always prioritized. That's what their financial plan has always been about. They have not spent enough time thinking about time. How much time do we really have? And that is a non-renewable currency. So, yes, we need balance. We need to have enough money to live, but we can't constantly trade our time for money, because at some point, that money is not actually going to fulfill its intended purpose if we don't make the time to use it.

Speaker 1:

The second reason it might be time for you to retire is because you need to invest in your health before it's too late. We need to acknowledge that years and decades of work and stress and burnout are not going to be the only way to make a difference in our lives. It takes a toll on our health and if we are not prioritizing our health, we're not going to have the thing our bodies, our healthy bodies that are actually necessary to do the things we want to do in retirement. There's a growing number of retirees who are experiencing depression, anxiety, stress-related, chronic health conditions and we don't think of that in retirement. We think of retirement as stress-free, as relaxing, as like a vacation. But the reason for this is they pushed so hard, they never prioritized their health and what they now have is a retirement where they have plenty of time but they're not able to use that time how they otherwise would have wanted to because they didn't prioritize their health. So if that's you, it might be time to retire. How do you prioritize your health? How do you prioritize exercise, the way you eat, the things that you do with your body, with your mind, with your spirit? These are the things that you can't get back. These are the things that, if work is preventing you from doing everything you need to do to maintain those and you're in a financial position to do so, it might be time to retire now.

Speaker 1:

The third reason it might be time to retire now is so that you can prioritize your relationships. Let's think about your work week relationships. Let's think about your work week. You spend 40 to 50 hours working. You're commuting for some number of hours per week. You're running errands, you're doing the things around the home. How much time do you actually have left and not just time, but quality time to invest in relationship with your spouse, with your children, with your friends, with the people that actually make life worth living? So much of your happiness and even your lifespan in retirement is going to be dictated by the health of your relationships. If you get to retirement without these relationships, it's not going to matter how large your portfolio balance is. You're not going to have the meaningful, fulfilling, joyful retirement you otherwise would have had had you prioritized relationships along the way. So hopefully you can do this while you are working, but if your work is preventing you from doing so, if you're not able to find the time to invest in those relationships, it might be time to retire now.

Speaker 1:

The fourth reason it might be time to retire now is to maximize your health span, not just your lifespan. Here's what I mean by that. Let's say you're 62 years old and you think you might live until 92. In fact, let's say that you could guarantee it. Obviously you can't, but for the sake of this, let's illustrate that you know that you have 30 years left. So what do you do? You say I need to max my social security so I have a strong income source to get me to age 92. So you work and you work, and you work from 62 to 70. You've maxed your social security benefit, you've maxed your 401k, whatever else you might be doing, and you think that now you have 22 years to fully enjoy that. Well, you have 22 years of life left. In this example, that doesn't mean you have 22 years of healthy life left.

Speaker 1:

There's a very big difference between our health span and our lifespan. Our actual health span in the US, on average, is age 66, meaning age 66, that's the average age at which health conditions chronic health conditions sometimes prevent us from actually doing the things that we could do with a healthy body. So if you're working from 62 to 70, that example sure, you have 22 years of life left, but you just used up all of your health years. And not just that, but I would argue that in many cases, the longer you continue to work assuming it's a high stress, high demanding job that doesn't actually bring you contentment and joy you're actually burning some of the healthspan that you have left in a faster way because of the added stress, because it's more time pushing off prioritizing your health. It's actually shortening your healthspan while simultaneously working those years to age 70, like I'm talking about in this example. So understand that it's not just lifespan that we're looking at when it comes to designing a wonderful retirement, it's healthspan. How do we make sure that, when we envision all we can do in retirement, some of those things need to go in the earlier years. Some of those things aren't going to be able to be done in your later 70s, 80s and beyond? Very big difference between your healthy retirement years and the years where you're living but don't have the health to do what you actually want to do. And finally, the fifth reason why it might be time to retire now is you need to break the cycle of working for work's sake.

Speaker 1:

I want to be clear here. Work is not a bad thing. In best case scenario, you continue to work throughout retirement, but you do so in a way that it's not taken away from relationship, from travel, from adventure, from the things that also bring you joy and contentment. Work by itself is not evil or bad. Work is actually a wonderful thing. What you want to avoid, though, is when work isn't a good thing in your life, when work's just adding stress, when work's deteriorating your health, when work's preventing you from doing the things you otherwise would be doing. That's what we're talking about here.

Speaker 1:

So if you are on that hamster wheel, I've talked to so many clients over the years of doing this where financially they were in a wonderful position to retire and they didn't like their jobs. So to me when I was younger in this profession, it seemed obvious well, go retire now. But I was always confused why people wouldn't retire. They kept staying on the hamster wheel. They kept saying one more year, one more bonus, one more round of maxing out my 401k. And what I realized is it was a bit of a hamster wheel. Their identity had been so tied into what they did for work, even if they didn't do it, even if they didn't actually like what they were doing for work. And so the fear of retirement because of this loss of identity, this loss of who I've been for the last 30, 40 plus years, that prevented them from taking the step and actually moving into retirement. So if that's you, where you're both financially in a position that you could retire but you're continuing to work because there's that fear, so you stay on the work hamster wheel and might be time to retire now.

Speaker 1:

Now, obviously, all five of these things are contingent upon do you have the financial means, the financial resources to support all of this? But there's a very fine and very delicate balance between getting the financial side right and not going so all in on the financial side that you continue putting off life, you put off retirement, you put off your health. That's what we want to avoid. How do you make sure that you have a financial strategy that can support what you want life to look like, but you're using those finances to actually support life? You're not continuing to work longer, save more, invest more and constantly pushing these things off and deferring them for another day.

Speaker 1:

So my call to action is this Evaluate in a very honest way where you are today. First ask are you financially ready? Then ask what's preventing you from retiring now or at the time when you will be financially ready? Maybe nothing, which is wonderful, but I know a lot of you watching. There is something that's keeping you tied to work and it might not be a healthy thing. So understanding how these non-financial factors, things like health relationships, purpose, understand how that plays a huge role in your ability to enjoy your retirement years, hopefully will help to push you to take the steps necessary to retire when it makes sense for you. Once again, I'm James Canole, 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 wwwrootfinancialpartnerscom.

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