Wealthy Retirees ALL Regret These 5 Mistakes… Don’t Be One of Them

Added: 2026-05-09

[00:00:00]Time after time, we see people in their 60s who come to see us, who come work with us, and they all have these five regrets. And so, in today's episode of Joe Knows Retirement, we're breaking down each of these five regrets so that you can learn and you don't repeat these regrets to make sure you can truly live this retirement that you have been dreaming of all these years that you've probably been working really hard for, maybe only 30, 40 years, and you've probably been at that same employer knowing that most of the people who watch this channel have that pension and have worked a long careers at the same place. And so, we're going to make sure that you are enjoying this retirement and learning from these mistakes and just be very grateful for these folks for making these mistakes for you to learn from so you don't have to pay tuition for mistakes and you can learn from other people having to pay tuition for their mistakes. So, let's jump into this video of Joe Knows Retirement.

[00:00:52]Joe Knows Pensions.

[00:00:55]Joe Knows Taxes.

[00:00:58]Joe Knows Midwestern Millionaires.

[00:01:01]Joe Knows Pickleball?

[00:01:03]No.

[00:01:06]This is Joe Knows Retirement.

[00:01:12]My name is Joe Schmidt, and the CEO and founder of Peak Retirement Planning. We are a retirement planning firm who serves those in the 50s and 60s who have pensions, who have a million dollars or more saved. That's the crowd that we work with. So, these five things that I'm talking about here today, we hear very, very often. And so, I'm glad to bring this to you to hopefully allow you to further your retirement and better plan moving forward. Now, the first regret that we hear, and and the one that we hear most often at that as well, is I wish I would have spent more money in the past, right? And again, you have to understand that we work with a crowd called the Midwestern Millionaires.

[00:01:46]There's a There's a book that I wrote on this topic of people. And so, they are extremely hard working, they are extremely frugal, and they are the best savers and the absolute worst spenders.

[00:01:55]And because of that, they really struggle to keep this fist from opening up, from opening up to enjoying and spending their wealth not only in the past but also throughout retirement. And so, regardless of what age you are watching this, I think this is something that any age group can struggle with.

[00:02:12]And so, what you see that when you're in your 60s is that, you know, when we run numbers for our clients when they first come join us, you know, that's one of the first things we do is we show them, "Here's an analysis of where you are and here's how much money you're going to be left with if you do nothing, right? If you just keep doing what you're doing, here's how much is going to be left." And it's usually a very generous amount there. A lot of times it's way more than they would have ever expected knowing they've lived paycheck to paycheck over all these years, right? These Midwestern millionaires are those who are hard working, diligent savers. They never made millions of dollars a year, but they just did the right thing year after year and just were disciplined. And so, they find themselves in a situation where they're just almost shocked. It's almost a paradigm shift because all their life they've been clipping coupons, they've been saving money. I've done a video on the 100 things these Midwestern millionaires do and you've probably were watching say, "That's me. That I I did the same things, right?" And that's what got you to this point. But, you've heard that saying all the time, "What got you here doesn't have to get you there." And so, these people in their 60s they realize like, "Wow, I I wish I would have told the kids yes more." Or, man, I wish we would have started to gift to our kids sooner so they could actually start to use it more in times when it could have been valuable for them and their families.

[00:03:25]These are the types of things we hear from our clients in their 60s. So, what can you do to get ahead of that? Well, just start to run your numbers to realize that you're probably in a better place than you think. And if that's the case, I got to challenge you. You can't take this money with you. There's no U-Haul behind a hearse. You can fly first class or your kids will fly first class is something that we always say.

[00:03:45]And so, whether that means you spend that money for more enjoyment, maybe that means you're you're gifting money uh your loved ones. Maybe that means you're giving more to charities. But finding ways to use that money more purposeful for what your goals are. So, I hope I don't have to tell you twice to spend more money. That should be pretty easy for you to do if you get permission and knowing that the the the the uh the plan's not going to fail if you do so.

[00:04:08]But obviously with this Midwestern Millionaire crowd, it sometimes takes seven times of telling them something before it resonates. As we know, that's a proven stat that typically it takes seven times of saying something for us as humans to to write that resonate. So, I'll keep telling you to spend your money and I just hope you'll continue to think about it and start planning for how you'll actually put that into action. Especially if you have that pension and a million plus saved because again, you're in that 2% club, which is another book I wrote, which again, you're in a unique situation, which is going to allow you to have more flexibility in what I call financial freedom. And financial freedom simply doing what you want, when you want, with who you want. So, my hope for you is that you don't regret that and you actually take action into doing it.

[00:04:46]Don't get into your 70s and say, "I wish I would have done more traveling. I wish I would have spent more money on the home improvements. I wish I would have spent more on my health so I could be healthier." All of those things are things that we hope you start to get ahead of now. The second regret that we hear from this crowd is I wish I would have retired earlier. And this comes off of the point number one as well as that they're in such a good financial situation that most of these people can afford to retire in their 50s because of their guaranteed incomes from their pension, but also knowing they have a million dollars or more saved, they can buy themselves an early retirement. And one of the the the concerns we hear from this crowd is, "Well, what about health insurance? I've got to pay for health insurance until I start Medicare at 65."

[00:05:28]And that is true, but sometimes employers will carry that coverage all the way to 65 or you just get it on the private marketplace. Yes, it is very expensive, but again, back to point number one, their biggest regret is spending more. Maybe that's something that's worth spending on to get that time freedom back, to be able to do the things you want to do, travel, spend more time with grandkids, be able to not be tied down to a 9-5 every single day, is something that we hear often. Now, also I want to make it clear, too, one of the other regrets that we see on retiring earlier can also be on the opposite side. So, people wish they retired earlier because of all the things I just mentioned, but for those people, we really want to see them have purpose in their retirement. We don't want to just see them retire and go golf every day because they're going to not have that thing to get up in the morning to get out of bed. They need to have some sort of fulfillment and purpose in their life. And so, that's the other regret of this point number two is retiring earlier can also be a negative because now you don't have that socialize aspect to your life from going to work every day. You don't have that competitiveness of being better every single day if you're just going to retire to lead it. So, what I'm saying to that is our clients typically say is that some of them are fine retiring early. They just need to make sure they have something else to step into. And those are when we see the most success from clients. And whether that's another job that maybe is less tied down, maybe it's not a 9-5, maybe it's more flexible, or maybe it's more of a mentorship leadership role where they can pour into others, which again is going to fulfill them and pour that into their cup as well. And so, those are all realistic things to think about. But you can see that some people regret they wish they were to retire earlier because they see the fun that it can happen in retirement if you do the right things. But all the others regret that they wish they wouldn't have retired so early or more so had a plan to think about afterwards.

[00:07:18]So, definitely deep concept for you to understand if you're either thinking about early retirement or if you already did early took an early retirement, maybe you're not enjoying it at this point. Those are two big regrets that we see in this aspect. So, my biggest hope for you is to plan this and think this out. What do you want that retirement to look like? Are you going to be able to fill 168 hours, right? We're going to sleep for probably 8 hours a day, but what are you going to do with the rest of the 16 hours every single day? and if you don't have those days filled, what is that going to look like for you? Are you going to feel okay not having that um you know, next thing to do, you know, every day? The third regret that we hear is more of a financial regret. And this one comes in two forms as well. This one comes from I wish I would have found a team sooner. You know, a financial planning team sooner to take this off their plate, to get better results, to do all the work for them. We also hear that I wish I would have found a different team sooner. And this is a team This is a person who's already worked with an advisor, but maybe they're not doing the full comprehensive work for them, and they've been missing opportunities, whether that's tax planning, or maybe that means they're not doing all the items all in one place under the one-stop shop, and so they've had to pay extra cost for everything.

[00:08:27]And so this is something that we see a lot of people say that their investment their advisor only does investment planning, and now they're getting to a point where they wish they would have gotten some of these things done sooner.

[00:08:37]Tax planning is a perfect example. Since 2017 Tax Cuts and Jobs Act, we've been doing really intentional tax planning for clients since that point. If you've been working with an advisor team who hasn't done that, that could have been missed opportunities where you're leaving money on the table, and now you've have to make up for it at this point. So you can't change your past, but you can change your future. And then we also hear too, like we work with a lot of DIYers, which is that first boat that I talked about, where they wish they would have worked with a team sooner. Because they DIY it because they think if I do this on my own, I'm going to save money, I'm going to have more control, but then when they realize like, oh wait, working with a professional management team, and this is something a study of Vanguard did, but they Vanguard says that if you work with a professional investment management team, you'll do 1 to 3% better versus DIYing.

[00:09:24]And so once we see that those DIYers trust a team, and they see the results, and they see the impact, and they see the freedom they have, they are just regret it entirely that they haven't done it sooner, right? And that's how it should work, right? If you work with a financial planning team, if they're not offering you value, then you shouldn't work with them, right? Fees are only an issue in the absence of value. So, if you're getting the value, should make that fee all worthwhile. It's also like where that business relationship should make sense. Something we tell our clients all the time is, "Hey, look, if you're unhappy at any time or you don't feel like you're seeing the results, we would never require someone to stay with us. We would encourage them to leave. We don't want to collect a fee if there's not enough value for that person to see that." And so, you know, we have a 99% retention rate because I believe that a financial planner serving a specific crowd that does that every day with more advanced strategies can do much better than someone just DIYing. And that's typically the case that we see for that crowd. And so, that's one part of actually getting better results, but what a lot of people don't think about is the amount of time it takes to DIY their retirement. You know, first and foremost, this is the only retirement they've ever planned, so they don't really have much experience. I like to say like, "Hey, would you ever go to a advisor who just started and trust him with your retirement?" Like, probably not. You want someone who's done it hundreds of times, thousands of times to make sure that they actually know what to look for and have proven successful in the past. And so, that, but also the amount of time it takes to plan for retirement, to develop all the spreadsheets, to develop all the software, to learn the softwares, to be able to know what even to look for, it requires a lot with also risk of missing things and not knowing what they don't know is what we typically see. And so, once they find a team, we typically see that they just remove emotion. We had a guy come to us and he said, "Joe, I'm 6 months in and I fully trust the team. I don't even look at this stuff anymore."

[00:11:08]And he came from a place where he looked at this stuff every day and did it on his own all these days as well. So, if that's you, maybe something to look into of working with a team. And also to have someone there to be there for your spouse if you pass away. That's something we see with a lot of clients we work with. One reason they come to us is for that that point there. But also again, the other time, if you're already working with a team and they're only doing investments, it is time to move on. Find a team who does everything for you all in one place, for probably the same fee or even less as what we often see. So, don't be getting taken advantage of there. Make sure you're taking advantage of that and getting ahead of that now. The fourth regret that we see is that people have not starting on tax planning sooner. So, I just touched on this in point number three, but I want to talk about specifically a point here in four about them wishing they would have done Roth conversions sooner. And so, this is again something we see from this crowd because they have so much in tax deferred, they have such a high guaranteed pension income for the rest of their life. That is a tax nightmare for this crowd. And so, often times we see that maybe their advisor tells them to go see their CPA when it comes to looking at Roth conversion planning or tax planning, and so they're not getting that done or accomplished. Or we see the DIY crowd basically say, "I don't know how much to convert. I don't know the optimal amount. I could guess, but I don't know if that's going to cause me to pay more or less taxes over time."

[00:12:24]And so, they just are left unsure of what to do. And so, that's why we recommend work with a team who's going to put together a long-term Roth conversion plan. And I can tell you right now, majority people we work with right now are doing Roth conversions.

[00:12:37]Not everyone. And especially those without pensions or million dollars saved, most of them should not even do Roth conversion at all or so very little amounts. But those from the 2% club, a strategy like this can start to make much more sense. So, understand the value of Roth conversions can save you hundreds of thousands dollars over your retirement if you're in this crowd. So, make sure you're looking into that and you have a long-term plan that factors in future RMDs, Medicare premiums, capital gains, and certain credits deductions you could phase in and out of as well to make sure you're truly optimizing that decision. The fifth regret that we hear has to do with estate planning. Now, there's many regrets from an estate planning perspective because many people don't want to think about this. They don't want to think about the time when they are no longer here. But I can tell you if you really want to leave a legacy behind, this is a really important concept to grasp. The number one regret that we see people have at this point is, "I wish I would have gotten my estate planning documents done sooner."

[00:13:32]I mean, they're sweating when we start to have this conversation and we asked uh you know, people looking to work with us, "Hey, do you have estate planning documents yet?" Majority people say no.

[00:13:41]So, if that is you, I don't want to tell you any more clearer and direct than this, you need to get this done. So, if you're not working with a team and you're looking to work with a team, work with a team who has this all built out so they can help you do it at one place to help you facilitate all the documents you need to make sure you're not going to miss anything there, you have everything aligned on your accounts afterwards, and just get that check marked off because we know that anything can happen at any time with us. And so, always being over prepared is better than being under prepared. So, that is one of the biggest regrets that we see people have at this point. And then we see once they get those documents done, it's like a weight off their shoulders.

[00:14:15]They've got it in place, they've got it good to go, and they don't have to worry about it anymore. It is good to check those documents every 5 years or so to update anything that you need. But again, if you work with a team, they'll cover all that for you. And then again, uh the other regret on our estate planning I want to cover here, I already talked about it earlier, but they regret not gifting more to their kids. So, we talked about spending more, but what about gifting more to your kids now?

[00:14:36]Because what we see is a crowd in their 60s, they start to realize I may leave my kids behind 5, 10 million dollars when I pass is what the analysis shows, where maybe they aren't going to really benefit from that much money at that time, but they really could use it now.

[00:14:51]Maybe to pay off debt, maybe to save and maximize their retirement accounts, pay for kids' educations. There's so many expenses that come up for working person, and you know that. You're the Midwestern Millionaire. You never made millions of dollars a year, you live paycheck to paycheck. That may be the same for your children, especially in today's economy, that you could really add a lot of value to their situation if that's a goal of yours, and it probably will not impact your financial goals in any way possible. And so, you can still do what you want, but also be able to impact them now. And if you ask them, would you rather have this when I pass or now, I can guarantee you all of them would say now, but that's your decision to decide if you think that would be worthwhile or not. And so, those are the five regrets that we see from people who are in or near retirement and those who are in their 60s. So, if you are watching this channel, I would love to know what your retirement regrets are.

[00:15:40]What can you give back to our community to add value to explore more of what regrets are out there because as you know, with this channel, we're all trying to grow together and provide an environment for those with pensions of a million plus to get the best content possible on YouTube is our number one goal. And so, with that being said, that's all I've got on today's episode of Joe and his retirement, and we will see you on the next one.