Ready For Retirement
Ready For Retirement
The Surprising Regrets of Wealthy Retirees | Root Talks
Retired with millions—but full of regret?
In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential.
What you’ll learn:
Common regrets wealthy retirees confess after leaving work
Why financial freedom means nothing without health, time, or joy
How to avoid estate planning mistakes that burden your spouse or family
Why intentional living matters more than chasing a number
Simple, high-impact ways to prepare for retirement now
If you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for you
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I'm going to guess that the majority of you watching this content or listening right now are good savers. That's why you are where you are. That's why you're listening to this content, thinking of ways to further optimize your finances. Now, some of you are thinking my partner is a great spender. Okay, well, we're not talking about them right now. We're talking about you in this savers mindset, and one of the coolest things that we have right now at Root going on is this community.
Speaker 1:It's called the Root Collective, and in this collective, there are certain prompts that I'll see that will catch my eye or James's eye, and that's how we come up with what we want to talk about today, and so today is a really interesting one, and this was prompted by Tommy C, who says the following For those who are great savers before retirement and are now retired, what are the little splurges that you now spring for that you wouldn't before retirement? And he has a couple in here that might make you think a little differently about how you want to save or potentially spend or give, or X, as we'll talk about today. James, when you're seeing someone talk about, oh my gosh, what are some of these things that maybe I wouldn't normally do, but now that I'm retired, I'll consider doing what's coming to your head Well, first thing is number one let's not wait until retirement to do some of these things.
Speaker 2:This isn't like a binary you don't do these things before you retire, do these things after you retire. But number two I think that we've heard a lot of cool things, a lot of cool tips, if you want to call it that, spending strategies, of what are some examples of people, of things people spent money on and they haven't regretted it, because no one wants to spend money and then regret it Like, why did I buy that stupid thing? I never ended up liking it. What a waste of money. I feel dumb for doing it. But there's other things people spend money on and they say I, that was one of the best things I've ever spent money on.
Speaker 2:And so I think that I, broadly speaking, categorize things into one of five buckets where we see these are like some pillars of good spending and so we'll go over those. And then you have some personal things. I know, I have some personal things. I know, and I, you know, when we're talking to clients, I think one of the fun things is because our advice isn't just about money, money, money. It's really about how do you have a, how do you live better lives. How do you live more intentional lives Like these aren't things that are unique to age 65 and above. These are really principles that all of us can try to live better by, and things that you and I personally try to live better by, so we'll share some of those stories as well.
Speaker 1:We certainly will. We talk about this phrase of goalpost planning One more year, one more bonus. Oh yeah, just one more project, then I'm going to officially retire. Now, if you're doing those things, some of you are like it's because I don't know what I want to do in retirement. Others of you are like you know now that you've actually brought it up. I think you're right and I think when I'm hearing you guys talk, it's resonating because I'm doing that, but I wasn't even aware, am I doing that? So what we want to do today is really shed some light as to some of these ideas, which hopefully will make you think a little bit more.
Speaker 1:Intentional is the way I would say it. So, if it's okay, excuse me, james, I'd like to start with a quick story, because it's a funny one and my clients like when I share it. So some of you guys already know this, but for those who don't, my dad loves his phone to an unhealthy degree and I love spending quality time with my dad. My dad loves surfing. I'm not a huge surfer, but I will go out with him in the water because it's when I get time with him. Now he actually has his Apple Watch, so sometimes he takes calls when we're in the water, which he knows he's not allowed to do, and I feel like I'm the parent when that occurs. But my brother and I were thinking for a long time how do we get more quality time with our father? And we can't surf all the time if waves are up or it's windy or whatever it is and so we bought a sauna to intentionally ensure that his phone or Apple watch would overheat, so he's forced to talk to us.
Speaker 1:Now some of you are thinking well, that's silly. Why don't you just talk to your dad for dinner? And if it was that simple, we would do that. But we all know some of us have these family members where it's just more difficult to get them engaged, whether it be game night or you just have to take them out to dinner because at home they're going to kind of be watching TV. So I am literally paying thousands of dollars, along with my brother, to just get quality time with my father, and that's something that I could wait to do until I quote unquote have millions of dollars retired. But I want the time now, while it's valuable. So we'll certainly get into, james, your stories, we'll get into what prompted today, but that's a quick story about just financially, why doing the right thing might not always actually lead to the right result.
Speaker 2:Well, I think that's a perfect example of the. Here's my five pillars. There's nothing magical about these as much as when I hear great stories like that, by the way, of what people spend money on that they feel really good about spending money on. The first pillar is experience. No one is ever upset that they spent money to buy an experience and in this case, the experience was simply quality time with your dad and that, theoretically, could have happened on the sofa. That could have happened. Surfing, that could have happened driving a car. But, like you're saying, there was a roadblock to that happening. You needed to eliminate the roadblock, which was overheat, the phone so it couldn't be used. But experiences, that's what travel is, that's what doing fun things is, that's what you're talking about. Number two is time. No one ever regrets spending money to buy their time back. I've used this example before. I do not like going to the grocery store. In fact, I hate going to the grocery store. And so he said how do we spend a few bucks to get food delivered, groceries delivered, I think it's $10 per order, so weekly it's 10 bucks, plus the tip that you leave. How many hours does that save of driving to the grocery store, going through the aisles, and it's just not a fun experience. So that's a couple hours of time back that I now have. So time, how do you spend money on time?
Speaker 2:The third is giving. No one's ever upset that they gifted money. This could be gifted to a charity, to church, to family, to friends, to whoever it is You're not going to feel like that's a great thing to quote unquote. Spend money on is giving. Then you have health. No one's ever upset that they spend a lot of money on health. You tell a lot of stories about this, ari, of getting the best doctor, of the physical therapy, of the things that you do, and health is one of those things. That. What's the saying? A healthy man has a thousand worries, a sick man has about one, or something like that. Like, until you don't have your health, you don't think about it. But health is, health is what allows us, of course, to enjoy everything else that we have. So spending money on your health gym memberships, good food for you, eating good food, spending money to do things that makes you healthier is a great thing to spend money on. And then, finally, I'll just broadly talk. Call it environment, like you want to live in a beautiful environment you want, whether that environment is aesthetically pleasing, and this is about people who like to decorate their home a certain way or do certain things for their home. This environment could be proximity to people you love or you care about. The environment could be proximity to things you enjoy doing. So I think those are categories that, broadly speaking, we should be spending money on.
Speaker 2:I like your example. For me, an example that comes to mind is not so much spending money, but spending time is. You mentioned goalpost planning just a bit ago, and it's a sense of oh, I'm going to work one more year because I'm going to get one more bonus, or I have some more stock vesting, or it's one more year of social security benefits increasing, or it's one more year of maxing. There's so many good financial reasons we can use to justify that, and what we always point to is hey, at some point you could take that to the extreme. Keep working forever, keep maxing your 401k forever, keep getting bonuses forever, but you missed the whole point. You missed the movie. Your life passed you by because you spent it working. Now I'm assuming you're working a dead-end job Not a dead-end job, but a job that you don't like A job that's not bringing you fun and fulfillment in the things you love doing. So we try to help clients be very intentional with that of. Money has a purpose, a very important purpose, but at some point the money needs to not be the main thing. At some point you've crossed this threshold where there is enough that it can now support you doing the things that you actually want to do. And continuing to work to get even more of it is actually pulling you away from what you're actually trying to do. To work to get even more of it is actually pulling you away from what you're actually trying to do.
Speaker 2:I face that too, not because I'm trying to retire. I love what we get to do. This is one of my favorite things in the world. To me, it's not a goalpost planning of okay, I'm going to stay at root for one more year. Two more years is man. I can get one more thing done, two more things done, three more things done, and surfing is something I claim to love to do. I haven't done it in two and a half years and I blame it on okay. Well, we have young kids and life's busy and I blame it on well, roots growing and that keeps me busy.
Speaker 2:The reality is, I'm just not making time to be intentional with it. And Wednesdays is typically when I record YouTube videos, podcasts, et cetera, and I always tell myself, okay, I'm going to record and, like the, the, the reward for doing that is going to be then I'll go surfing, or then I'll go I don't know do something fun. I'll go do jujitsu, I'll go train. But I fall into that same trap that we encourage clients not to not have. Oh, there's one more thing I can be productive with. There's one more thing I can check off the list. Look, I have three more hours till I got to go home for family dinner. Like, look at all these things I can do.
Speaker 2:And I fall into this trap and it's and, and just last week, for the first time in two and a half years, I finally said you know what I'm going to commit to. Here's the things I need to get done today the, my enough. Like, if I get these three things done, which was filming a certain amount of videos, I am going to go surf and I did it and I went surfing and I was reflecting on the way back that, as much as we tell clients to do this of don't goalpost plan, don't don't keep pushing off the things you actually want to do I personally am guilty of now. I love work, and so it's not like I'm continuing to do something that I dislike doing, but there's a certain amount of intentionality that doesn't come from continuing to do the same old, same thing.
Speaker 2:Like, how, like, how do you constantly reflect on what should I be spending money on, like your story? What are the things I can do to create more meaningful experiences? What are the things I can do to improve, spend money on, to improve my health, to buy back my time to you know those various things I talked about? The same thing happens with how do we spend our time Not just how do we spend our money, but how do we spend our time, and sometimes it's thinking about the life that we want to live. It's thinking about what actually matters to us, and surfing is obviously not the only thing that matters. In fact, it's pretty low on the priority list of the things I actually care about. But in general, it is something that I do want to do, and it's this sense of just constantly reevaluating and reassessing where are we and how can we spend our time, spend our money, spend our energy, spend our talents, doing the things that bring us closer to the life that we want to live.
Speaker 1:Now this is interesting. What was it about last week versus any other week in the last two and a half years that made you go? Today is the day I'm going to give myself the reward.
Speaker 2:You know I didn't think that. Well, I'm glad you just asked that, because I hadn't thought about this until literally the second. An office mate came in this morning and said guys, we work four blocks away from the ocean and we never get in the ocean. How ridiculous is that Kind of like, how dumb are we that we live in this paradise and we don't actually utilize the paradise we live in? And so I said, ok, well, if I can get, you're right, first and foremost, but number two, if I do this isn't to say abandon all work and go.
Speaker 2:If I can get my enough done, if I can get my top three things that are my priorities for the day done, instead of just saying, okay, cool, there's always more things to do, so I'll just pour myself into that Then I'm going to go do this other thing that is called a reward for getting those things done. I don't want to call it peer pressure, but having someone do this and I think in fact, that comment that you started with from Tommy C mentioned that I believe correct me if I'm wrong, but one of his experiences, one thing he spends money on, is doing something that friends can come along, and it's that sense of doing something with someone else makes it way easier to do and way more enjoyable to do.
Speaker 1:It's so fascinating because, let's assume, you go surfing every week and now you're happier at home, and now your wife goes. We're connecting more. I don't know what's happening, but I just feel it's different and you're more present and you can't quantify that on some spreadsheet, as hard as you try. And there are financial advisors as nerdy as us who will try, but the reality is you are not going to look back going. Oh my gosh, I'm so glad I did those 12 more projects and you know I didn't need more time with my grandkids Like we've never heard anyone ever say that, and this is all we're doing all day. So I think when we're talking to clients, we will pride ourselves on being very transparent. We are not mean, but we are transparent. We will pride ourselves on being very transparent. We are not mean, but we are transparent because, as you just saw, what prompted James to actually right now go surfing was someone came into the office and said how dumb are we? And so some of you are working right now going. I'm 60. There's no way I could retire because I've never had healthcare outside of my employer, so surely I'm waiting until 65 because, like, why not? And then you'll see a video that might wake you up and go, hey, maybe that's not the deal. And then all of a sudden you might have years back of prioritizing health or family or friends. And next week we'll talk about an even bigger story actually two weeks from now where there's an actual woman I spoke to who was really upset that she had $3 million, and I said, look, that's just. I don't want to be mean here, I just don't hear that every day. Why are you mad that you have $3 million? And she goes on to say that she didn't need 3 million and now she can't hike to the degree she'd like because of the health impact from sitting at work. So we'll talk more about that in a few weeks. But the point here is financially, there are things that you can only do when you know your plan allows for it, but you don't have to wait until this magic date to actually start doing some of these things. So I think it would be helpful to maybe give some of you guys a few ideas here. And, james, if there's anything you wanna add, please feel free. But this is straight from Tommy once again in the community. But this is straight from Tommy once again in the community. These are just a couple of his ideas.
Speaker 1:And so he says whenever I have an experience, he springs for the better and the closer seats. That might not be valuable to you, but that's what he likes to do. He talks about. Whenever he can, he gets prepaid parking so he's not worried about finding street or cheaper parking or having to walk a mile to the venue, like James did when he was younger at the baseball games. He says he'll upgrade to a large or even extra large coffee.
Speaker 1:He says when I'm on a cruise, we opt for excursions that have less people and they cost a little bit more. The experiences have been 100% worth it. He tips more generously. And then our favorite one that we read here is he said when I buy experiences, I buy two extra tickets. This forces us to find two friends to go with us. If they pass back, great, and if not, I'm not worried. More fun with friends is worth the additional cost.
Speaker 1:So he goes on to say what little things do you splurge on that makes you happy? I don't think those are litter things, I think those are big things and I want to tell Tommy I'm proud of you, because it's really hard, unless you know. I want to tell Tommy, I'm proud of you, because it's really hard unless you know financially you're in a good spot to go. I'm going to buy two extra tickets. What if my friends don't actually join? So if there's anything you take away from today's episode, I hope you think about it and let this be. Maybe this episode, the person walking in to your office going maybe today's the day to go surfing. Anything else, james, you want to add?
Speaker 2:No, I James. You want to add? No, that would be it. I encourage everyone listening. Just keep it super simple.
Speaker 2:How could you better spend your time and how could you better spend your money? My example was a time thing. Your example was a money thing. Now you're spending your money to get time and I think that that's how do we live better lives. We look at those two things. Where are we spending money? How are we spending money?
Speaker 2:I have five things that like to fall in those categories. Again, experiences, time giving, environment or health. If it's checking one of those boxes, I'm going to feel good about it. So what is one little thing that we can do? What gym can you go sign up for Not just sign up for a gym You're probably never going to go. Can you sign up for a personal trainer to keep you accountable? Can you sign up and do so with a friend, to keep you accountable, to make it fun? What are those things that you can begin doing? What are those experiences?
Speaker 2:To me, the simple experience was I'm going to go surfing for 30 minutes in the middle of the day because I got my enough done. What are those things that you can do? I'm really glad I did it. Whatever I would have gotten done in those 30 minutes pales in comparison to the fun I had being in the water, doing that, having fun with a friend. So just those little things. So what's one single thing you can do to stop? I'm guilty of this? You're actually really good about this. I bet you're not actually guilty of this. You get in the routine, you get in a thing that's comfortable and it's hard to kind of pull ourselves out of that until someone comes along and shows you those blind spots that by nature, by definition, you're not seeing in your own life and you have to go make a change to get out of it.
Speaker 1:Well, thank you, and we're going to put the thread of what Tommy said in the link below. So if you want to go comment on the exact post, which is the reason we're making this exact episode, go comment in there and let us know and we will read those ideas on future episodes. So you can check all of that out in the description, whether you're on YouTube or on the podcast app.
Speaker 2:All right. Thank you everyone for listening and we will see you all next time. See ya. The information presented is for educational purposes only and is not intended as an offer or solicitation for the sale or purchase of any specific securities, investments or investment strategies. Investments involve risk and are not guaranteed. Any mention of rates of return are historical and illustrative in nature and are not a guarantee of future returns. Past performance does not guarantee future performance.
Speaker 1:Viewers are encouraged to seek advice from a qualified tax, legal or investment advisor professional to determine whether any information presented may be suitable for their specific situation Once again.
Speaker 2: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.
