What the Happiest (and Unhappiest) Retirees Know

It’s always nice to know where you’re heading, and what experiences people arriving before you have had on their journey.

Retirement is certainly no exception to this rule. Learning from the happiest retirees can inform your decision making and planning.

But perhaps more telling information would come from an interrogation of what retirees who assess themselves as unhappy share, at least in terms of traits and circumstances.

ESI Money continues his look at a book profiling retirees, their happiness, and their conditions, and gleans some interesting insights from its contents.



Today we continue our coverage of the great retirement book What the Happiest Retirees Know: 10 Habits for a Healthy, Secure, and Joyful Life. It is packed full of solid information and statistics about the state of retirement today.

So far we’ve just covered an introduction to the book and if you missed that you may want to read it first before getting to this post.

Like with other books I’ve reviewed on ESI Money, I will share some key passages from this one and give my thoughts on their conclusions.

Let’s get started.


Unhappy Retirees


In this post, we’ll be discussing chapter 2 which covers the characteristics of unhappy retirees, or UROBs, as the author calls the unhappiest retirees on the block.

As we get deeper into the book we’ll highlight the traits of happy retirees (HROBs — happiest retirees on the block) in depth, but before we do that, it’s helpful to see what the unhappy ones do. If we can avoid their habits and pick up ones from happy retirees, that’s a win-win.

The author begins this section with the following story:

In my role as a managing partner at Capital Investment Advisors, I’ve met a lot of unhappy folks. Some were entrepreneurs who worked 24/7 for 30 years and literally didn’t know how to stop. What’s the point of retirement if you have no interest in or curiosity about anything else? Golf, tennis, walking, hiking, biking — it’s all boring and unproductive to this type of UROB. He or she never “has the time,” even when staring at a blank social calendar.

Some of the UROBs I’ve met are “pretend rich” like Uncle Roman, and some are legitimately rich like J. Paul Getty. Most have allowed work to define them, rather than actually living their lives like HROBs do. Now, in retirement, they’re reaping the compound interest of 20, 30, 40 years of accumulated bad habits. That’s not the kind of interest anyone wants.

If your career starts to become who you are (versus what you do), then who are you when you leave that career?

That’s the issue so many people face — especially high-powered, successful individuals like lawyers, doctors, and business executives.

Others can fall into the same traps as well.

But it’s not just the issue of not being able to let go of your career (which has become your identity). The author goes on to list seven traits of unhappy retirees in Jeff Foxworthy’s style.

You Might Be An Unhappy Retiree If…


1. You Might Be a UROB If You Drive a BMW

I love this one (though it seems strange to me for reasons I’ll state later).

Let’s first share what the author has found and some of his thoughts on this issue:

My research showed that the number one luxury brand for unhappy retirees was BMW.

But why do UROBs drive BMWs? I’ve had a lot of time to ponder this. I’ll tell you what I think: there’s something about the performance-oriented, fine-cutting, hard-driving, expensive-to-repair flashiness of a BMW that leads to unhappiness in retirement.

I don’t know any other way to describe it. To this day, when I look at a BMW, it just screams: I’m trying to prove something! To whom? To my friends? To my spouse? To myself? Maybe all of the above. To me, it connotes a level of insecurity in the driver, suggesting there’s a gap he or she is trying to fill. Rather than finding an organic, self-reflective, and healthy way to do it, the person is deflecting these feelings of inadequacy onto “The Ultimate Driving Machine.”

So funny. But probably true as well.

I remember leaving the office of the financial planner we met with a couple of years back.

We left the same time he did and as we were pulling out I noticed he got into a nice, brand-new BMW. Yep, he was trying to prove something, to project an image.

My wife and I just laughed at it. It was the “big hat no cattle” factor playing out from The Millionaire Next Door. He wanted to look rich and successful, but odds are he was not that way.

So I get that part.

I think there are other professions, such as real estate agents, that use their cars to project how wealthy they are. When I see an expensive car I simply laugh inside, knowing that odds are the person is paying a fortune for it when they probably should be saving more.

But what I don’t understand is this:

The happiest retirees don’t need the flashiest luxury brand, but they still want to enjoy the ride. Think Lexus. Think Acura, Buick, or Toyota. Leave the BMW on the lot.

Also, I wonder where Teslas fall into this group. Certainly, it’s a luxury brand. I just want to know if it falls into the “look at me” category. I think it does personally.


2. You Might Be a UROB If You’re Too Keyed up About Investments


The summary:

There is a big difference between being actively involved in your investment portfolio and taking on a second career as a stock trader.

Don’t get me wrong. It’s a good idea to spend time with your finances, and you certainly want to have at least a base level of financial literacy. But once you get too far into the weeds, it’s a red flag. Tormenting yourself over fast-moving facts and figures almost always leads to poor investment returns over time, not to mention the ongoing emotional toll and burden. Being glued to every drop or rise in the Dow Jones Industrial Average while you’re in retirement? That’s not making you more money. It’s a formula for anxiety because investing is a bumpy, unpredictable game in the short term. Compulsion won’t guarantee you returns, but it will guarantee that you drive yourself crazy. Obsession is not your friend.

I wasn’t keyed up about my investments on the way to retirement and I’m certainly not going to get keyed up in retirement.

It is a bit disconcerting initially when you retire as it’s a new feeling and many may wonder if they have enough.

But in my experience, that feeling goes away quickly – in the first week, for me. So just set your investments, resolve to not touch them the first week or so, and everything should sort itself out.

And find other things to do that obsess over your investments. Studies will show that being an active trader is one of the main ways to lower your overall return. So, at least for the most part, set it, and then forget it.


3. You Might Be a UROB If You Live Far Away from More Than 50 Percent of Your Children


The summary:

What do I mean by far away? Anything you can’t reasonably drive to. A two-hour drive is fine. Three roadside hotels and 5 tanks of gas? Not so much.

Of the nearly 2,000 retirees I surveyed, the retirees who lived near at least half their children were five times more likely to be happy than those who did not.

The happiest retirees say it’s impossible to put a price tag on life experiences, especially memories made with children and grandchildren. Often, proximity to children isn’t just about the parent-child relationship, but about being able to be good grandparents. An overwhelming amount of research is devoted to parent-child dynamics, yet, as other research shows, close grandparent-grandchild relationships are themselves a marker of strong family ties and come with their own distinctive benefits to well-being.

My take on this:

  • Our kids both live in our city — 15 minutes or so from us. We see our daughter and son-in-law at least once a week if not several times and see our son once a month or so. It’s pretty nice. We also do big vacations together.
  • “Five times more likely” is a big difference, something you should consider strongly before you ignore it.
  • We don’t have grandchildren yet, so my comments in that arena are TBD.


4. You Might Be a UROB If Your Adult Children Still Live at Home


Their thoughts:

Living near your adult children is a good thing. Living with your adult children is not.

While you can’t control whether your kids ultimately get hitched, statistics indicate an important point: Unmarried adult kids who live at home are significantly more likely to be dependent on mom and dad. The financial and emotional burden of this is just too hard for many retirees. This period of life requires tremendous adjustment: careers, relationships, financial planning — all of these are in flux. Parents may struggle with how to appropriately care for or relate to a child who has become an adult but still resides in their home. They may also find themselves resenting the unexpected extension of parental responsibility in a season that was supposed to be “about them.”

When our son told us he was quitting his non-profit experience early, we tried to dissuade him, but he was adamant about leaving.

So we told him it was his life and up to him, but that he was not coming back home to live. He was 25 and it was time to get out on his own.

Which is exactly what he did.

Sometimes the bird flies out of the nest like a rocket (like our daughter did). Sometimes you have to push them out of the nest. 😉


5. You Might Be a UROB If Your Kids Are on Your Payroll


The summary:

I’ve written in the past about the importance of moving adult kids toward independence. While every child-retiree relationship is complex, every circumstance different, and every financial situation unique, the data shows that taking kids off the payroll — or at least giving them a pay cut — also boosts happiness in retirement.

Unhappy families average $714 a month in support of their twenty, thirty, and forty something-year-old “kids.” Happy retirees spend less than $500 a month on their adult children. If your children are not financially independent, you are 1.5 times more likely to be an unhappy retiree. Think about it. If a happy retiree is living on $5,000 or $6,000 per month, $700 is a lot, right? That means 10 to 20 percent of your budget is going to your kids instead of fueling the next chapter of your life.

My study found that over 40 percent of retirees are giving their adult children some level of financial support. This doesn’t include children with special needs or the occasional gift of a trip to Disneyland or Christmas cash. It means support from parents to subsidize everyday life. I’m talking about private schools for grandchildren, car leases, rent, mortgages, paying down debt, and more — because the kids can’t afford the lifestyle they keep.

I’m not saying you’re a bad person for helping your kids out. Heck, almost half of American retirees do it! The problem is that your generosity can have, at best, a negative impact, and at worst, a devastating effect on your own finances and happiness levels.

A CNN article from September 2020 showed that 52 percent of young adults in the United States are living with their parents. Blame whatever you want — the economy, Covid-19, TikTok — but you can’t argue with facts: 52 percent is the highest that percentage has been since the Great Depression. This is a double-edged sword. We want to have our family close, as we’ve learned from HROBs. But overspending on our adult kids for BMW payments and private schools for grandchildren can weigh heavily, create resentment, and lead to higher levels of unhappiness.

I think we all know that Americans have some “unique” money habits.

And by “unique” I mean “terrible.”

This is just another set of data points that confirms this.

We do not have kids at home and we do not support any of them on a regular basis. We’re happy about it. 😉

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6. You Might Be a UROB If You’ve Been Divorced Twice or More


Their thoughts:

HROBs get one marriage redo. More than that, and you’re more likely to be unhappy. Marital status is a critical variable of retirement happiness. If retirees are not married or have never been married, they are 4.5 times more likely to be unhappy. Happiness levels rise when you’ve been married one or two times. Beyond that, if you increase the number of times you have been married, you’re asking for trouble — and I don’t just mean from your ex.

There are lots of reasons someone might be unhappy if they’ve been divorced many times, but one that comes to mind is financial.

That’s because divorce is expensive.

Let’s take a large amount of money — enough for most people to retire on. Let’s say $3,000,000.

Now let’s look at how divorce decimates this large amount of money pretty quickly if it gets divided up in half again and again:

  • After one divorce a person has $1,500,000.
  • After two divorces a person has $750,000.
  • After three divorces a person has $375,000.

There’s a big difference between $3 million and almost one-tenth of that! What about people who have been divorced more than that? (My biological father has been divorced five times, so I’ve seen this play out first hand.)

But worse than this is the compounding you lose. You never get the chance to get even close to $3 million as you split the money and lose half of your compounding nest egg — so you’re at a huge disadvantage. You lose both money and the time where your investment could be growing.


7. You Might Be a UROB If You Had Two or Fewer Core Pursuits Before You Retired

The summary:

If the happiest retirees I know are the most curious retirees, it is likewise true that the unhappiest retirees I know are the most incurious. They say curiosity killed the cat, but I think in retirement, it’s the opposite. A lack of curiosity about new pursuits and passions can lead to an uninteresting, uninspiring, dull, and less purposeful life.

It’s difficult to develop and start focusing on core pursuits that didn’t exist before retirement. Just like saving money, you want to start nurturing your passions early. We all know there’s a compounding effect when it comes to saving money. It’s easier for us to accumulate higher levels of wealth if we start earlier. The same math applies to developing core pursuits.

It’s tough to start playing golf at age 60. It’s really tough to start playing tennis at age 70. It’s almost impossible to become social when you’re 80.

We’ve covered this before and will do more so in the review of this book, but just to repeat:

Anyway, that’s the list.

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What’s your take on happiness in retirement?

1 thought on “What the Happiest (and Unhappiest) Retirees Know”

  1. I really like the work done by Wes Moss on happy retirees. His list of 10 habits of the happiest retirees focuses more on the social aspects of retirement rather than financial issues. Not saying that the financial aspect is not important but what are you going to do with six Saturdays a week and one day of rest? Being a person that enjoys alone time it is going to be difficult to reach out and connect more often with friends and social events. It is going to have to happen in conjunction with defining those core pursuits. My list is not up to 4 core pursuits yet but I am working on it.


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