Retirement Insights: How Current Retiree Experiences Guide Successful Retirement Planning

What do retirees who are truly happy have in common — and what do those who aren't wish they'd done differently?

In this episode, Brandon digs into the latest research on retirement success and retirement regrets to build a clearer picture of what actually separates retirees who are thriving from those who are struggling. The data tells a nuanced story — one that goes well beyond savings balances and rate-of-return targets.

You'll get a ground-level look at the current state of retirement security in America, including some eye-opening numbers on how retirees are actually spending their money versus how they planned to. From there, Brandon walks through the attributes most commonly shared by retirees reporting the highest levels of retirement happiness — and at least one of them will likely catch you off guard.

Retirement income and income planning take center stage as Brandon explores why the type of income you build matters just as much as the amount — and why the gap between guaranteed and non-guaranteed income has a surprisingly powerful impact on how retirees feel day to day.

The episode closes with retirement insights drawn from what current retirees say they'd do differently, distilled into an actionable framework for those who still have time to course-correct.

If you're building a retirement portfolio and want to protect more than just your balance sheet, this one's worth your time.

📌 CHAPTERS
─────────────────────────────────────
[1:18] — The State of Retirees
[4:33] — The Emotional & Social Side of Retirement
[6:31] — Two Very Different Retirement Experiences
[9:16] — What Successful Retirees Have in Common
[14:12] — The Control Factor
[16:15] — The Four Big Regrets
[23:58] — What's Ahead for Pre-Retirees
[29:29] — Your Action Plan

Transcript

00;00;20;14 - 00;00;49;07
Brandon
You are listening to the Yield to Reason podcast, where we help you build a bulletproof retirement portfolio with a keen eye on investment income, because independent wealth hinges on your ability to pay the bills. We're dedicated to solving retirement's biggest riddle how to turn your hard earned savings into spendable cash so you can enjoy the retirement you actually want and make it the retirement you truly deserve.

00;00;49;09 - 00;01;18;23
Brandon
I am Brandon Roberts. Thanks so much for joining me today. As we look at the current state of retirees and try to build an action plan for ensuring your retirement, success and happiness. It turns out the two are very tightly connected. Today we're going to talk about financial statistics because that's what I do. But we're also going to get into the weeds about less numerically driven aspects of retirement that are just as significant as a quote unquote, healthy rate of return.

00;01;18;25 - 00;01;54;21
Brandon
And consider that last statement, a good bit of foreshadowing on my part. So let's start where things stand. According to the 2025 Senior Citizens League Retirement Survey. Only 19.4% of retirees consider themselves financially healthy. 52.4% rank themselves as vulnerable, meaning that they're just trading expenses and 28.2% identify themselves as at risk, which means their generated income doesn't meet their expenses.

00;01;54;21 - 00;02;22;01
Brandon
They're having to go into savings, and the possibility of running out of money is significantly higher for this group of people. Now, there are a lot, a lot of data that have been published for us to look at that look at the savings rates of Americans, especially retirees, the amount of money that they have on hand. And and when we look at it in the context of averages, it looks quite bleak.

00;02;22;08 - 00;02;44;04
Brandon
But honestly, the data is not all that helpful because it doesn't give us much insight into what you can do. We know that a number of people simply didn't save enough. What they do from here is kind of up in the air, and there's not a whole lot that you can take from that outside of Save More, which we are going to get back to at some point.

00;02;44;11 - 00;03;13;09
Brandon
But we also want to look more finely under the hood here to figure out what is going on with retirees. Are they are they good or are they not good? Are they are they succeeding or are they failing? What's what is driving success or failure here? I want to start with some data from a very recent survey that discovered 67% of retirees are spending more on groceries than they planned.

00;03;13;11 - 00;03;33;07
Brandon
60% are spending more on home health and auto insurance than they planned. 43% are spending more on property taxes than they planned. 37% are spending more on medical care and prescriptions than they thought they would be. Now, here's some some, some very interesting stuff. 34% are spending more on technology than they planned to be spending at this point in their life.

00;03;33;09 - 00;04;01;26
Brandon
And 34% are spending more on transportation. So we've always heard that prices go up over time. There have been numerous calls to plan for inflation, but one of the weird things about headline inflation is we don't necessarily see people paying more all across the board, but we do see people paying more in certain areas that we didn't always think would happen.

00;04;01;26 - 00;04;33;06
Brandon
Groceries are a very weird one, and a particularly frustrating one because it's not easy to substitute out that expense. We also see from research conducted by the Every and CNBC. That way, more retirees are carrying credit card debt than before. 68% as of the most recent survey. That's up from 43% in 2020. We also know that new retirees are far more reactionary to market volatility.

00;04;33;08 - 00;05;13;04
Brandon
Those who are within the first five years of retirement were way more likely to make asset allocations in the face of recent market volatility than people who have been retired for a longer period of time than that. According to the Nationwide Advisor Authority Study, now looking a little less at numerical information and trying to get a sense of the overall well-being from a mental and social health standpoint, there is some interesting data that is going to play a pivotal role in a lot of today's discussion.

00;05;13;06 - 00;05;43;13
Brandon
So the Harvard Study of Adult Development, which is one of the longest standing research projects on a number of aspects related to adult life, but retirees are certainly looked at. It, identified that for them, loss of social connections in retirement was the primary challenge that they faced. It's more problematic than financial woes, the loss of daily structure and social connections.

00;05;43;15 - 00;06;11;02
Brandon
It leaves a lot of retirees feeling lonely and and isolated. And this is a very pervasive, threat to the overall well-being of retirees, because this one knows no boundaries with regard to how much money you save, with some small caveat, this is generally a very big shock, this social isolation, this loneliness feeling for for people, especially in the first several years of retirement.

00;06;11;08 - 00;06;31;17
Brandon
We do see from the research that people have been retired for a while, are a little less affected by this, perhaps because they're a little more accustomed to the lifestyle of a retiree. But it does come up as a big shock for a number of retirees just how lonely they are and how much they miss the social interactions that they used to have while they were going to work.

00;06;31;19 - 00;07;02;08
Brandon
Picking through the data on retirees and how they're doing and what is what is working and what is not working. It's pretty stark that we have a split in the retirement system, at least in the United States. That shows us that on the one hand, there is a group of people with relatively low savings. They have a decently high amount of stress in their life, and they are pretty isolated and somewhat miserable in retirement.

00;07;02;10 - 00;07;27;02
Brandon
And then, on the other hand, we have those who have achieved a relatively high degree of guaranteed income in retirement. They have a healthy amount of social fulfillment, which may be driven by their ability to to generate disposable income. More on that just a bit. And these are also, in general, healthier individuals who appear to be loving life.

00;07;27;05 - 00;07;53;12
Brandon
And to me, this was a relatively fascinating discovery. Picking through the data to get this, this podcast episode together. So for years I have been aware of the data regarding savings rate and average 401 K balance and stuff like that. And it looks in general pretty bleak. But I've also often wondered why we don't see more blood in the streets over this.

00;07;53;12 - 00;08;17;02
Brandon
Because if the data about the poor savings achievements among individual Americans in general is so bad and it follows through to retirees, we should see a lot more people begging in the streets than we than we do. But but this doesn't happen. So we do have a certain degree of success that's going on that we kind of overlook.

00;08;17;05 - 00;08;42;05
Brandon
But we also have for sure a segment of people who are struggling. And I do think that there are lessons we can take from both cohorts to build an actionable retirement plan, to not just talk about things like what your savings rate should be, what your expected rate of return should be, or what basket of of income style investments should you be focused on.

00;08;42;07 - 00;09;16;22
Brandon
That's all important, and it's all going to weave into some of this. But there are some other things that we need to be thinking about in the context of retirement preparation that we aren't. And some of these things, I'll be very honest, completely for me, came out of left field. Let's start with the retirement successes. And after pouring through a whole lot of research, what I kind of distilled everything down to are three attributes among the happiest, most successful retirees.

00;09;16;24 - 00;09;47;26
Brandon
And here's what they are. Number one, physical health. That's right. Physical health. This one I didn't see this one coming. This this was this was new to me. So research from MassMutual identified that retirees who took care of their health prior to retirement were happier than those who didn't. So it's often easier to address certain health problems when you're younger.

00;09;47;28 - 00;10;32;04
Brandon
It's also sometimes easier to address health items when you are still working, because a number of workers have more robust health insurance plans, which give them greater access or greater flexibility when it comes to getting things done that are going to require medical intervention. It's also a generally good idea to kick bad habits prior to retirement. It turns out that people who have neglected health issues in general, or compounded longstanding, unhealthy behavior, has left them in a certain amount of or with a certain amount of regret in retirement.

00;10;32;04 - 00;11;06;08
Brandon
And those who were kind of on the ball about their health have achieved greater success in retirement. They're happier individuals when they are in their retirement years. The next item on the list is guaranteed income. This one will not be new. Talked about it before on the Yield to Reason podcast. There are multiple studies that have identified that higher amounts of guaranteed income in retirement lead to happier retirees with far less stress.

00;11;06;10 - 00;11;29;12
Brandon
We have every data that shows us that the happiest retirees are those with pensions, annuities, or higher levels of Social Security income. Boston College research shows us happier retirees, or those with some level of annuity income when controlling for wealth. So that would mean if you and I had the exact same amount of savings, but you bought an annuity with some of that money and I did not.

00;11;29;17 - 00;12;06;01
Brandon
Chances are pretty good you're happier in retirement than I am. We have data that shows us public sector employees with pensions report better retirement outcomes, happier retirement outcomes than private sector employees who are under defined contribution plans, things like 400 and KS, etc. and here's the most striking one. Research released by the Retirement Income Institute in 2024 showed that retirees spend two times guaranteed income wealth compared to just investment, wealth and and a companion survey to this research.

00;12;06;03 - 00;12;58;09
Brandon
I'd read that more people feel comfortable spending on non-essential items if they have an additional $10,000 per year in guaranteed income than if they simply had an extra $140,000 in savings. And this cohort of people who I know, who I who answered in this fashion, had net worths in excess of $500,000. So these were not people who were necessarily doing poorly from a wealth accumulation standpoint, but they still identified the receipt of a relatively modest amount of guaranteed annual income as a a, a component that would make them feel much safer about non-essential expenditures than if they simply had an extra $140,000 lying around.

00;12;58;11 - 00;13;18;08
Brandon
The third item on the list is preparation. This is paying off debt before retirement, ideally, or having a plan to have it paid off at some point during retirement. The research does show us that retirees who paid off all of their debts sometime in the window of five years prior to retirement, tend to be the happiest in retirement.

00;13;18;10 - 00;13;45;23
Brandon
But creating a plan is more than just that. It's also sitting down and figuring out what retirement is going to look like, and what you're going to need to do to successfully manage through retirement. If you have a plan, you now have something that can ground you when things don't go the way you expected them to, and it stops you from making kind of, knee jerk decisions in the face of of fear because times get a little tumultuous.

00;13;45;26 - 00;14;12;21
Brandon
So planning is absolutely critical. I've talked about it before, and it is certainly an attribute that is critical when it comes to overall success and happiness in retirement. Now, I do want to mention that that in addition to these three attributes, there are a couple of other things that are a little less difficult to control that do stand out as differentiators when it comes to happiness versus displeasure in retirement.

00;14;12;23 - 00;14;45;14
Brandon
Control. Control plays a big, big role in how retirees kind of view retirement as it is unfolding. So those surveyed who mentioned that they themselves feel like they got to choose when they were going to retire are the ones who tend to be happiest in retirement, which means, conversely, that those who felt like they were forced into retirement, they generally do not respond as positively about the way they look at retirement.

00;14;45;16 - 00;15;06;18
Brandon
Now, there are certain things that are absolutely going to be under your control when it comes to when you ultimately retire. There are people for whom retirement is brought about by a downsizing at the company they work for, or by some sort of illness or injury that takes them out of work and they simply don't return. Those are things that are going to make people feel a little less in control.

00;15;06;21 - 00;15;36;13
Brandon
But, but, but one of the things that you can absolutely have at your disposal, to give you a little bit more sense of control in the face of, of downsizing or, or illness or whatever the item is that you don't necessarily get to control is a plan. And more critically than that, a an establishment already of some degree of passive investment income so that you know what to do, you know where to turn to.

00;15;36;14 - 00;16;15;02
Brandon
You have the resources to pay the bills prior to actually retiring. And then if you are forced into it, the transition is a whole lot easier. Now let's turn to the regrets that I retirees identify. So the data shows us that there are four categories of regret that I think everybody can actively plan to manage so that they don't fall in the same boat as the surveyed retirees are, regarding some of the displeasure that they're facing in retirement.

00;16;15;05 - 00;16;53;08
Brandon
Not surprisingly, the number one regret has to do with saving. The biggest consistently ID regret that retirees have is that they simply didn't save enough. And there's many different ways that this gets sliced. They didn't save enough. They didn't start saving early enough so they wish they'd saved sooner. And then the other one is that a number of people wish that they had saved more consistently, and that that last one, saved more consistently is probably the easiest one for everybody who is currently not retired.

00;16;53;10 - 00;17;29;07
Brandon
To address that could have a massively meaningful impact on your overall retirement success. Save more is tough. Sometimes the budget just isn't there. Save sooner. Well, once you are the age you are, you can't go back and save any sooner. But saving more consistently is absolutely a habit that you can try to commit to. And this one you don't need to save large amounts to make a likely large a significant difference in where your overall retirement assets end up.

00;17;29;09 - 00;17;57;22
Brandon
So starting with something and just being consistent at it has a very, very strong impact on overall growth of your retirement portfolio. Another interesting data point we're going to revisit this near the end of this episode. So the average baby boomer began saving for retirement at roughly age 40. Put a pin in that. We'll get back to it.

00;17;57;24 - 00;18;23;05
Brandon
Let's talk about the second biggest request or regret that retirees have. It's health related. So again, we know people who have addressed health issues, who have tried to take a little bit more care of themselves, tend to be happier in retirement. But a major, major regret many retirees identify is that they didn't take care of these things when they were younger, when they were working, when they had a different health insurance plan.

00;18;23;07 - 00;18;51;25
Brandon
The Medicare system is not that bad in most circumstances, and there is a lot of great health care that is available to retirees who are in the Medicare system. But there are certain health insurance plans that are more robust, and a number of people may feel more secure in pursuing various health care when they are in their working years.

00;18;51;27 - 00;19;17;22
Brandon
I've actually met a number of retirees, and it's this is this is an embarrassing admission because I already said that the health thing kind of blew my mind as I was going through this research, and this really didn't coalesce for me until after I was looking at this and thought back on it. I have I've met a number of retirees who are struggling with some sort of health condition, and they it definitely affects their day to day life for sure.

00;19;17;25 - 00;19;46;03
Brandon
And they are things that they totally could have. And many situations done at least a little something about years prior. But they didn't. And then they got to retirement and started to to address it. Or maybe it just got to the point where it couldn't be ignored anymore. In fact, this research shows us that 66% of retirees say they are now trying to address or improve some neglected health item.

00;19;46;05 - 00;20;15;12
Brandon
So it it is a disruptive force in a number of retirees lives, and it's not something that you should necessarily defer if you want to try to increase the probability of a very happy, very successful retirement. Number three on the list not planning. So a number of retirees realize that they totally missed the boat on setting out a plan for retirement.

00;20;15;14 - 00;20;39;16
Brandon
A number of of retirees, according to the Senior Citizens League, 40% of them mentioned that they never specifically saved money for retirement. I have a sneaking suspicion pensions probably played a big role in this. Individuals who kind of, thought that they they their their retirement plan was already taken care of because they worked for an employer that had a pension plan.

00;20;39;18 - 00;21;06;00
Brandon
There are still a lot of of baby boomers who were absolutely, a member of a pension plan and, still many who are receiving benefits, maybe not the original income benefit. They thought they were going to, but some degree of pension income in retirement. So I suspect pensions played a role in those who didn't really spend a lot of time planning, but for sure successful retirees are those who show early savings.

00;21;06;02 - 00;21;32;04
Brandon
They they plan out the process of of going into retirement. And they also make use of various retirement instruments. So for when KS, IRAs, etc.. And we do see that, that the less successful retirees, those who are not all that happy and not all that financially successful in retirement tend to be the exact opposite. They didn't save much.

00;21;32;06 - 00;22;06;23
Brandon
They didn't plan, and they also made very little use of various retirement instruments. Number four on the list is relationships. Social isolation and loneliness in retirement is real and it's somewhat dangerous. In fact, a 2024 meta analysis identified that isolation social isolation in retirement has a hazard ratio for all cause mortality of about 1.35 that is in on similar standing to smoking and obesity.

00;22;06;25 - 00;22;35;26
Brandon
It it has a very highly negative impact on just identified satisfaction, but also a negative impact on an overall mortality outlook. Now, if you're looking for a, a quick solution here, according to the same research, 100 hours, no more than that 100 hours annually of volunteer, work wherever you want it to be had a substantial impact on declining that mortality risk.

00;22;35;28 - 00;22;58;15
Brandon
Now, sadly, fewer than 10% of retirees reach out to old friends once retired. All of the ones who don't generally regret it. Many, many retirees surveyed know that in their mind it would be much, much easier or would have been much, much easier to develop, social bonds with people while they were working versus the position that they are now.

00;22;58;15 - 00;23;29;21
Brandon
Now that they are retired and, and a number of them feel a little nervous or cautious about having the money to even go out and pursue social activities. Research from Fidelity and Texas Tech showed us that social spending as a category is the biggest bang for the buck when it comes to retirement happiness. So of all the things you could possibly spend your money on, retirees identify things that that have to do with with social oriented activity.

00;23;29;23 - 00;23;58;03
Brandon
So these could be things like going out to eat, going to a concert, doing something, going to a, some sort of theme park with some friends or things that people get the most amount of enjoyment in, in retirement. Now they also identify these things as non-essential. So when you don't have adequate resources to do this, it it compounds and it makes life more miserable in retirement.

00;23;58;05 - 00;24;24;05
Brandon
So for those who are not yet retired, what's what's on the horizon? What can you what can you expect first? The data does show us that older people do tend to be happier. But there's a caveat to that because we're probably committing a little bit of survivorship bias. Those who tend to be happiest in retirement are those who are wealthiest, and those who are able to do the things that they want to do.

00;24;24;05 - 00;24;56;20
Brandon
And we do know that those people tend to live longer than individuals who are less financially well-off and generally less happy in retirement. So as age increases, the number of people still alive decreases, and we're probably over representing the individuals who are wealthiest and happiest in retirement. When we conduct some of these surveys. But we do know that there is a trend, kind of a four stage trend, that retirees typically fall follow.

00;24;56;22 - 00;25;26;15
Brandon
And it looks something like this. First, there's a honeymoon period where things are great. There's newfound freedom to do what you want, when you want, and just not the stress that once accompanied day to day life when it came to work. But then within kind of a 2 to 5 year range after retirement, there is a disenchantment phase that settles in where people start to get a little anxious.

00;25;26;15 - 00;25;51;10
Brandon
They get anxious about the money that they have and how well, how long it's going to last and the newness and the fun ness of, of retirement kind of wears off. And life isn't always as great at this point. Now, thankfully, once we get beyond this, roughly five years out from retirement, there's kind of a reorientation phase where retirees kind of accept their new normal.

00;25;51;13 - 00;26;15;07
Brandon
In a lot of cases, they've endured their first major financial catastrophe. They survived and find out that noone's probably not going to be the end of the world the next time one comes up, and then eventually retirees reach a stability phase where they're just kind of used to life in retirement, and they're not as bothered by a number of things as they once were.

00;26;15;09 - 00;26;43;26
Brandon
Now, in conjunction to this, we also know about the the so called retirement smile, which shows us that people go through kind of a go go year phase, then a slow go phase and then a no go phase. And that has to do with what they spend money on. And and the smile is identifiable by research. But the one thing I want to point out here is that it does not perfectly align with these four phases that have also been identified.

00;26;43;29 - 00;27;12;28
Brandon
So probably the best example I can give you on that is a number of people are still going to be pretty high in the gogo phase of the smile and entering the disenchantment phase of retirement. So while they're spending more money, there's still probably going to be this kind of decline of overall life satisfaction for whatever reason. The warning here is don't get too depressed because it's probably going to pass.

00;27;13;00 - 00;27;38;17
Brandon
And the other big thing to note is that this time it probably really will be different. So the next generation that will be headed into retirement is generation X, and they face a very different landscape than baby boomers did. 56% of baby boomers were part of a pension at some point in their working careers. That compares to 14% of Gen Xers.

00;27;38;19 - 00;28;08;29
Brandon
The amount of some degree of consistently guaranteed income will be substantially less for Gen X than was the case for baby boomers. And we also know that Social Security faces a number of question marks, given its its solvency woes that have been a topic for for news headlines for a number of years now. But interestingly, the timeline that a lot of of younger generations identify as when they're going to retire isn't that much different than baby boomers.

00;28;09;02 - 00;28;35;00
Brandon
So 56% of baby boomers expected to work until age 70, but the median age of retirement among them is 62. And 70% of baby boomers who ended up retiring early did so for reasons beyond their control. Something that we already addressed earlier in this episode. So younger generations are going to need to focus more of their attention on income generation within their assets.

00;28;35;02 - 00;28;59;28
Brandon
This could be guaranteed income, or it could be lesser guaranteed items for just income in general. But the one good piece of information here is that that subsequent generations have absolutely started saving for retirement earlier than baby boomers did. We mentioned earlier that the average age was around 40. Same research shows us that for Gen X, it was age 34, for Gen Y, age 28 for Gen Z 23.

00;29;00;02 - 00;29;29;05
Brandon
That's, that's an extremely early point in life to begin saving for retirement. So taking all this information, what what can we do? I think we need to keep three key things in mind. The successors for retirees. We need an income plan. We need we need to pay attention to and address health items. And we can't overlook the role social connections are going to play in our overall retirement happiness.

00;29;29;07 - 00;30;01;00
Brandon
And given the role, social connections and the attempt to avoid isolation will play. I think it is prudent not to overlook the significance of ensuring the budget line item for social spending. We know from this research that that gives us the biggest bang for the buck when it comes to overall retirement happiness. Everyone's going to be a little different, but this research shows us that on average, there's nothing else you can spend money on that would make you any happier.

00;30;01;03 - 00;30;26;00
Brandon
So build a plan, and within that plan, make sure that you're saving early, but don't stress out about it. Just be consistent about it. And do think about creating income. Put it on the horizon. Address your health problems. Now. They're only going to get worse and more expensive as time goes on. And find your tribe and make sure that you've got the money to actually do things with them.

00;30;26;03 - 00;30;35;04
Brandon
That's all from me for today. Thanks so much for stopping by and until we meet again, please remember real wealth doesn't just add up. It writes, checks.