Ready For Retirement
Ready For Retirement
5 Things Retirees Regret - And What You Still Have Time to Get Right
After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning.
Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets:
- No clear purpose after work: Retirement without direction quickly turns from freedom to restlessness.
- Neglecting health too long: Wellness is what fuels the retirement you’ve dreamed about—don’t wait to prioritize it.
- Losing social connection: The workplace offers more structure and belonging than many realize until it’s gone.
- Expecting retirement to feel like a vacation forever: It won’t. But with intention, it can become a reinvention.
- Being too afraid to spend: Your money is a tool to live—not something to hoard while life passes by.
Don’t wait to think about what really matters. The best retirements are built not just on financial security—but on vision, relationships, health, and joy.
Start designing a life you won’t regret.
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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
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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I've had the privilege of working with hundreds of people as they've prepared for and entered their retirement years over the past dozen plus years or so. I've seen the good that comes with this and I've seen the regrets that people have when they don't do things right or when they don't prioritize the right things ahead of time. And what's most interesting to me is these regrets typically aren't financial related. They have everything to do with time, relationship, purpose, and those are the things I want to talk about today. There are five of these regrets I see most commonly, and it's these I want to share with you today, because if you are watching, it means there's still time. There's still time to understand what these regrets are so that you can take steps to avoid them as you plan for your future. The first regret that I see is people plan for their retirement but they don't actually plan for life after work. In other words, they knew when to retire, but they did not know what to retire to. The reason this is so common is we have this misconception that retirement is all about getting the numbers right. It's a math problem to be solved Do I have enough? How do I allocate my portfolio? How much can I take out each month and, yes, those are very important, but that's only half the equation. The other half of the equation is what are these numbers actually doing for you? What are the withdrawals doing for you? What does a life well lived look like for you? And if you don't have a clear picture of that, it doesn't matter how good the numbers are, you're not gonna be fully satisfied with your retirement. In fact, you're going to regret the fact that you didn't spend time thinking about what you actually wanted to do. The best way that I've seen this put is there's two types of freedom there's freedom from and there's freedom to. What people preparing for retirement so often dream about is that freedom from, freedom from the alarm clock, freedom from the deadlines, freedom from the reports, freedom from the commute, freedom from all the things that you don't like about work. And that freedom from is great. But after a few weeks, after a couple months, that just becomes a new normal. You're used to not waking up with an alarm clock. You're used to not having to submit that report at that time. You're used to not having to do performance reviews with your direct reports or your superiors. That just becomes a new normal If you don't have the freedom to, the freedom to do the things you want to do, the freedom to be with the people you want to be with You're not going to actually have the type of retirement that you've always envisioned. So, yes, the freedom from is good, but if we're not simultaneously understanding the freedom to, if we don't know what we're going to actually do with our time, the numbers, they're important but they're incomplete.
Speaker 1:So that's the regret I see people have is they didn't plan for life after work. So once the honeymoon phase ended and it always ends, honeymoon phase ended and it always ends they were left with this regret of wishing they had spent more time thinking about what they actually wanted to do in retirement. So, if that's, you, think about it Now. It doesn't actually matter if you're in that phase right now. If you're preparing for that phase, think about what you want to do, who you want to spend time with, who you want to be. What does life look like? For this to be one of the best seasons of your life possible? There's no reason. It can't be. You no longer have the commitments of work. You no longer have the responsibilities that you once had. You get to create whatever you want to create. But don't just focus on the financial. Also focus on what you're retiring to.
Speaker 1:The second regret that I see people have is they underestimate the importance of health. Too many people say I'll get healthy when I retire, I'll get healthy when I don't have to wake up early and work late and come home tired. But here's the problem Once you lose your health, it's very difficult to get it back. And if you keep thinking that one day you'll prioritize your health, that one day is constantly going to get pushed further and further into the future and before you know it, you're going to have a health event, you're going to have a chronic disease, you're going to have something that you can no longer go back and change. So the earlier you can prioritize your health. This can be simple walks, this can be stretching, this can be eating well, do the things that are necessary to move your body, to nourish your body, to do the things so that you can actually enjoy retirement.
Speaker 1:Health in and of itself is wonderful, but what people don't realize is that if you don't have that health, you can't take the trips you envision taking. You're not going to be able to play with your grandchildren the way you envision playing with them, you're not going to be able to golf the way you want to golf. All these things are in some way dependent upon you having a healthy body, a healthy mind, the ability to do them. So prioritize health today. Even if it's just 10 minutes here, 20 minutes there, do the things that you need to do, yes, for your health, that alone should be enough, but also so that you can enjoy all the things you've dreamed about with your retirement. And if you can start thinking about compound interest, not just as it pertains to your portfolio, but also as it pertains to your health, there's going to be a very big payoff in the things you do today to invest in your health, prioritize your health. Without it, nothing else is going to be as enjoyable, is even going to be as realistic to accomplish as you otherwise would have wanted it to be.
Speaker 1:Third regret I see clients have when they look back upon their retirement is that their relationships drift. A very common sentiment is they did not realize how much work was a thing that bound together some of their social relationships, some of the social dynamics. Even if you didn't love your job, chances are good there's at least some people at your workplace that you enjoy connecting with. Maybe, if you don't realize you enjoy connecting with them. There's something healthy, there's something beneficial of having other adults to connect with. I remember one of my first jobs out of college, when I got into this profession. We had some clients that they would come into the office all the time, and at first I thought, okay, this is because they want to review their portfolio, they want to review their financial plan. And what I started to realize is that's not the case at all. I think some of these people are actually working with us because they retired. They don't have those social connections. We are not a social connection for them. We are that thing for why they exist. And so what I encourage clients is establish those connections. Establish those relationships. Do not let them drift.
Speaker 1:Don't fail to realize how much work, whether you love it or hate it, tends to pull you together, tends to keep you close with other humans, and that relational aspect of who we are and what we're doing cannot be underestimated. There is a Harvard study of adult development and this study is one of the longest running studies on aging and happiness and it had this to say about the importance of relationships Close relationships, more than money or fame, are what keep people happy throughout their lives. Those who are most satisfied in their relationships at age 50 were the healthiest at age 80. People with close social ties they get sick less, they experience less cognitive decline. They actually live longer. So relationships isn't just about having someone to talk to, it's not just about the fun that comes along with it. There are very real, tangible mental health benefits, physical health benefits, life expectancy benefits to having those relationships.
Speaker 1:The problem is is if we're not actively maintaining those, if we're not actively investing in those, they're going to slip away once you retire. So the takeaway is this Be proactive with family relationships now. Be proactive with friendships you have now. If you're not proactive, it's very easy for those things to slip away and it's much harder to rebuild that later on. This is a regret I see with clients. Learn from that and make sure that you're going into your retirement years building a healthy social dynamic.
Speaker 1:The fourth regret is people who tell me they expected retirement would feel like a vacation. Now here's the reality. It does feel like a vacation for many people for the first several weeks, maybe even the first several months, but at some point that just becomes a new normal and if you expect it to feel like a vacation for a very long time, you are going to be let down and you're going to regret not doing things to proactively build what you want your retirement routine to look like. You're going to feel let down when you go into retirement thinking this is going to feel like a vacation and all of a sudden you start to feel lost. You start to feel purposeless, you start to feel like you're drifting and there's a disconnect between how you thought you would feel and what the reality actually is.
Speaker 1:I recorded an episode with Dr Riley Moynes several months back now, and Dr Riley Moynes gave a TED Talk that's been viewed by several million people and he talks about the four phases of retirement. The first phase is that vacation phase. You retire, you're no longer waking up. At the time you don't want to wake up. You don't have to report to the person you don't want to report to, you don't have to do the projects you don't want to do, and that feels great. You feel like you're on vacation, but that doesn't last very long.
Speaker 1:Phase two then comes into play. Phase two is feeling lost and lost. You lost some sense of purpose. You lost some sense of community. You lost some sense of structure and routine in your life and you're feeling a little lost in life. Where are you going? What are you doing? What's your purpose and why are you actually here? It's very difficult to feel or think that that's the feeling that you're gonna have when you're in the middle of your working career, when you're in the middle of a high-stress job or you're in the middle of a very demanding thing that you're doing. That's all you can dream about. I would love to feel a lack of this purpose here, and it does feel great when you lose that, but only to an extent.
Speaker 1:From there you can move to the third phase if you're intentional about it, and the third phase is trial and error. Really, what you're doing is you're reinventing yourself. That version of you that was you from age 20 to 60 or 20 to 65, whatever it was that's no longer you. Now, of course, there are aspects of that. Hopefully you're building in good habits, with relationships, with family, with hobbies, with health, all these things. Hopefully those continue. But the thing that you did for 40, 50 hours a week, that's no longer there.
Speaker 1:So phase three is trying to reinvent yourself. You're experimenting. Don't expect to just find that thing right off the bat. Try new things, try woodworking, try volunteering. New things, try woodworking, try volunteering, try pickleball. Try new hobbies, try, try, try. And when you keep trying things you're going to find that some don't work for you, and that's perfectly fine. You should expect that. What you'll also find is that you might find a new hobby, you might find a new purpose, you might find a new thing to volunteer with that you never thought to do before. That's the importance of trying and experimenting.
Speaker 1:And if you get that phase right, then you move to phase four, which is reinvention and purpose. You now have your new identity. Typically there's some service element to this, there's some giving back element to this. But what you've done here is you've gone through the honeymoon phase and did the feeling loss and lost to reinventing and trying new things and to find that purpose again. You find that person that you want to be and that's what makes for meaningful retirement.
Speaker 1:But if you expect retirement to feel like a vacation, you expect it to feel that way for the entire 20, 30 years that you're retired. You're going to be let down. So that's a regret people have, as. They wish they would have understood the highs and the lows that were gonna come. And, by the way, there's a very real way to avoid those lows If you're proactive today about understanding what are those relationships that you wanna build and maintain. How about your health? How about your hobbies? How about that sense of purpose, of giving back, of community, start those things today. This isn't really a retirement thing, this is a life thing. The only difference is with retirement, you now have those 40, 50, 60 hours a week freed up that otherwise were taken, that otherwise were committed to a job that you're no longer going to.
Speaker 1:And then, finally, the fifth regret the retirees have that I see quite a bit, is they were too afraid to spend. There's this very difficult shift that's gonna take place. If you start working, maybe in your early 20s, and you save and you invest and you defer and you grow your 401k, you grow your Roth IRA, you grow your brokerage account and you get to retirement. So used to putting money into your portfolio, but now it's time to start taking money out. It's a very scary feeling for most people. Now you're taking this thing that you spent your whole life building up and you're pulling money out of it. And not only are you pulling money out of it, but you're doing so when the markets are up and when the markets are down.
Speaker 1:That can be terrifying, and what I see so often is people who spend their whole lives building this portfolio. They start to think of that portfolio as the goal in and of itself. That portfolio is what they felt like they were building towards, and if that's the identity that you're building towards, you're going to be very afraid to pull money out of it. If you can instead shift the thinking of. This is not the thing that matters. This just enables to think that matters, which is the life you want to live Doing things with people you care about, prioritizing your health, prioritizing your relationship. These are the things that matter. This is just the thing that makes it all possible.
Speaker 1:And if you spend your retirement years too afraid to spend this, what's going to suffer isn't your portfolio. Your portfolio is going to keep growing if you don't spend it, but these other things that actually matter are going to gradually deteriorate. You're not going to be able to take the trips you want to take. You're not going to be able to do the things you want to do, and one day you're going to look back when you're in your late 70s, your late 80s and you're and you can have a portfolio. In many cases that's far beyond the portfolio of your wildest dreams.
Speaker 1:But you're going to look back with regret, saying I missed the opportunity to spend that when I had my spouse with me. I missed the opportunity to spend that when I had my full health and vitality. I missed the opportunity to spend that when I had young grandchildren and family could easily get together. So avoid that regret. Avoid the regret of not spending by having a healthy vision of what your portfolio is actually designed to do, so that you can turn that success, that financial success, into the peace of mind and confidence of a life well lived. So, even if your retirement is years away, these are things you should absolutely begin building now.
Speaker 1:And if you want more tips on how can you live better in your retirement years, make sure that you subscribe to this channel. And if you're wondering how you can design a financial plan that helps you take these principles and incorporate them and tie them into your actual finances, reach out to us. At Root, financial Link is in the show notes below. But the main takeaway is this is if you can start to understand these regrets that future you might have if you don't take action today. You can take the appropriate action today to avoid them and live out the remainder of your retirement doing the things you want to do, without the regret that's so common to many. 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.
