Search Captions & Ask AI

The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140

May 27, 2026 / 39:22

This episode covers retirement planning, focusing on risks such as longevity, inflation, partner, market, sequence of returns, withdrawal, and health risk. Host Jesse Kramer discusses how to identify and mitigate these risks for long-term financial success.

Jesse Kramer, a financial planner, introduces the concept of inversion in retirement planning, inspired by Charlie Munger's approach to problem-solving. He emphasizes understanding potential failures before determining solutions.

The episode outlines the first seven of fourteen risks retirees face. Longevity risk is highlighted as the possibility of outliving savings, while inflation risk concerns the decreasing value of money over time.

Partner risk is discussed in terms of communication among family members regarding financial plans. Market risk is explained as the inherent volatility of investments, and sequence of returns risk focuses on the impact of market downturns early in retirement.

Withdrawal risk involves taking out too much money too quickly, and health risk emphasizes the importance of maintaining health to enjoy retirement. Jesse plans to cover the remaining risks in the next episode.

TLDR

Jesse Kramer discusses seven key retirement risks and strategies to mitigate them, focusing on longevity, inflation, and market volatility.

Episode

39:22
00:00:00
Let's experiment with an interesting approach to retirement planning that borrows from one of history's greatest
00:00:04
problem solvers. Most of us ask ourselves, "What does success look like and how can I achieve it?" But what if
00:00:10
instead we asked, "What does failure look like and how can we avoid it?"
00:00:14
Let's identify all the risks we might face or ways we might fail and only then
00:00:19
decide the positive actions we should take to mitigate those risks. Welcome to personal finance for long-term
00:00:25
investors, where we believe Benjamin Franklin's advice that an investment in
00:00:29
knowledge pays the best interest both in finances and in your life. Every episode
00:00:34
teaches you personal finance and long-term investing in simple terms. Now, here's your host, Jesse Kramer.
00:00:41
Welcome to Personal Finance for Long-Term Investors, episode 140. I'm Jesse Kramer. I'm a financial planner
00:00:46
working with retirees and busy professionals prepping for retirement across the USA. You can learn more at
00:00:52
planwithjesse.com. This week's review of the week is from Steve Stewart, who left kind words and a
00:00:57
five-star rating on Apple Podcasts. Steve, drop me an email to jesseb bestinest.blog and I'll get a supersoft
00:01:03
podcast t-shirt mailed out to you. Now, on with the show. I was listening recently to one of Charlie Mer's famous
00:01:09
parables. Probably the the 10th time I've heard him tell the same story. Charlie dropped out of Michigan to serve
00:01:15
in World War II and he entered the Army Air Corps, which was the predecessor to the US Air Force. And with Munger's math
00:01:21
background, he was a math major at Michigan. He was sent out to Caltech in California to learn how to be a weather
00:01:27
forecaster for the Army. Now, working for the Army Air Corps, he famously thought to himself, "How can I kill
00:01:33
these pilots?" Yes, how can I kill these pilots? He kind of turned the problem on
00:01:37
his head, and he came to two overwhelmingly strong conclusions. The most accidental yet obvious ways that he
00:01:44
could get pilots into trouble were by either one sending them too far a field kind of against the wind such that they
00:01:52
would actually run out of fuel before returning back home. And then number two was sending them into cold and wet and
00:01:58
icy conditions such that ice would build up on their wings. It would weigh down the planes and cause them to crash. So
00:02:04
those were the two most obvious and most common death mechanisms that Munger identified and he then became fanatic
00:02:10
about reverse engineering the best practices to ensure that he helped his pilots avoid those two fates. You might
00:02:17
have heard me discuss Charlie Munger's principle of inversion. This is the principle of inversion that we're
00:02:21
talking about. You might have heard me discuss it before, but we're going to
00:02:24
double down on the principle of inversion today. I'm going to walk you through the most common ways retirees
00:02:28
and long-term investors can fail at achieving their goals. We'll identify the biggest risks they face and the most
00:02:34
obvious failure points along the way. And then only after thinking about how we can get ourselves into the biggest
00:02:39
trouble will we invert our issues and find the smart solutions. So first my thought was let's identify these risks
00:02:46
that we're going to be talking about today. And I should say before we go any
00:02:50
further today's going to be part one because I've got a list of 14 risks and
00:02:53
we're going to dive into them with with some detail. We're going to cover the
00:02:56
first seven risks today on episode 140. We're going to cover the second set of
00:03:00
seven risks next week on episode 141. So, let's first compile this massive list of the 14 risks that retirees and
00:03:07
long-term investors face. And I'll do a kind of just a really quick description
00:03:11
before diving into more detail. So, number one, longevity risk. I think it's
00:03:15
probably the biggest, most obvious risk that I can think of when it comes to retirement. It's the risk that you live
00:03:20
so long that you run out of money. That you've only built a retirement plan assuming you'd live until 75 or 80 and
00:03:25
then you end up living till 95. That's longevity risk. Number two is inflation
00:03:30
risk, which a lot of these risks are going to be interconnected in some way. And inflation risk certainly has a
00:03:35
connection to longevity risk. But inflation risk is this everpresent and kind of modern economy's risk. Meaning
00:03:41
that today's dollar is going to lose spending power over time. And combined with living longer than expected,
00:03:47
inflation risk means our current dollars simply won't go far enough into the
00:03:51
future. That is inflation risk. And number three, I call it partner risk or household risk or stakeholder risk.
00:03:58
Maybe partner risk for short. And the idea is, you know, are you and your spouse or you and your kids or you and
00:04:02
whomever is important in your life. Are you guys on the same page? Could disagreements throw off your plan, your
00:04:08
financial plan in some way or could an untimely death, you know, the death of a partner throw off your plan in some way?
00:04:14
So basically the idea is there, you know, how contingent is your plan on the other people in your life and is that a
00:04:19
risk? That is partner risk. Number four, market risk. And just kind of in general, market risk. The idea here is
00:04:25
that investments can go down in value, meaning that there is a risk that investments actually hurt your plan more
00:04:31
than they help your plan. That's market risk. And then fifth is a specific type
00:04:36
of market risk that we've heard many times on this podcast before, I know, sequence of returns risk. That's number
00:04:41
five. It's a particular market risk. Even if your investments go up over the
00:04:45
long run, if they go down too early in your retirement, it can create this chain reaction that you never actually
00:04:51
recover from. That is sequence of returns risk. Number five. Number six, withdrawal risk. Your cash flow needs
00:04:57
are too much for your portfolio and you're simply withdrawing too much too quickly. That's withdrawal risk. Number
00:05:02
seven I have is health risk. And again, it's a general risk. Will you find yourself at 70 years old too weak or too
00:05:09
sick to, you know, hop on a plane to play with your grandkids to live whatever version of an active retirement
00:05:15
that you've been hoping for? That is health risk number seven. Number eight,
00:05:19
I call shock spending risk, but most specifically, I think of it as long-term care risk. It's the care of this sudden,
00:05:27
unforeseen, extremely large spending need. So, these kind of unforeseen large expenses are one of the biggest
00:05:34
derailers of a retirement plan. One of the most common culprits happens to be long-term care, which often costs more
00:05:40
than $10,000 per month for multiple years at a time. So, that's the eighth risk, shock spending/ long-term care
00:05:47
risk. Number nine, cognitive decline risk. It's related to health risk in general. It's also related to behavioral
00:05:53
risk, which we'll talk about next. But the idea here is that cognitive decline,
00:05:57
sure, it's got its own health risks associated with it. We'll talk about
00:06:00
those in the health section. But it also exposes us to maybe some irrational behavior, less logical behavior, more
00:06:07
susceptibility to scams and things like that. So that's why cognitive decline
00:06:11
risk has its own category here. Number 10, behavior risk. Will you get in your own way and make irrational decisions?
00:06:18
Will you let fear or greed or following the herd guide your decisions to your own detriment? That's behavior risk.
00:06:25
That's number 10. Number 11, I call assumptions risk. It's an interesting
00:06:28
one that sits kind of underneath a lot of the other risks. It's that overly optimistic return assumptions or
00:06:34
underestimating inflation or ignoring taxes or assuming a static spending rate over time. It's the risk that our model
00:06:41
itself, our retirement model is wrong. That's assumptions risk number 11. And
00:06:46
it's pretty prevalent among the DIYer community, I've got to say. Number 12,
00:06:50
policy, legislation, and tax risk. So think about tax rates, interest rates, social security policy, which I know is
00:06:56
a really hot topic for those people who are worried about if social security will somehow change in a big way over
00:07:01
their retirement. RMDs is another big one, estate taxes. There are a lot of vital inputs to retirement that are
00:07:07
frankly out of your hands. They involve the government in some way. So what can you do to kind of mitigate your risk in
00:07:13
these situations? That's number 12, policy, legislation, and tax risk. Number 13, I call identity and purpose
00:07:20
risk. If I can't scuba, then what's this all been about? What am I working
00:07:25
toward? >> Create from the office. So, forget about finances. What about your life excites
00:07:29
you? You know, is there any chance that you're going to find yourself with this
00:07:31
mid-retirement crisis because you're not sure what it's all about for you?
00:07:36
There's an interesting stat. I'm going to steal it real quickly from Fritz
00:07:38
Gilbert. I think it's that 28% of retirees at some point self-describe their feelings as depressive in some
00:07:47
way. Maybe they don't have full-fledged depression like a a psychiatrist would
00:07:50
diagnose, but they actually feel kind of this melancholy about their retirement.
00:07:55
So, that presents identity and purpose risk number 13 today. And that brings us to number 14, perhaps the most unique
00:08:02
one that I've added to this list. It's called the deep risks. Deep risk is a
00:08:06
term coined by Bill Bernstein, very famous investing writer, and it covers four massive risks to long-term
00:08:13
investing. Inflation is the most common deep risk and deserves its own call out which we've already done here. But the
00:08:18
other three are what I'm going to talk about here with number 14. The other three deep risks are deflation,
00:08:23
confiscation, and devastation. And I'll explain those all in detail when we get
00:08:27
to number 14. And the question here is, how will your retirement fare in the face of one of those sociopolitical deep
00:08:33
risks? So those are my 14 risks. And today I'm going to deep dive into the first seven of those 14. And we'll
00:08:39
finish the list next week on episode 141. So, let's work through the first seven risks to consider the the ways we
00:08:46
could mitigate and combat those risks. And as we step through this exercise today and next episode, here's what I
00:08:51
would encourage you to do. I do not think you need to take what I'm about to
00:08:55
say as some sort of dire warning that you must change your ways. I don't want
00:08:59
you to hear these 14 risks and these 14 sets of solutions and and think to yourself, you know, oh my god, I'm at
00:09:04
risk and I have to immediately act because our financial plans, our retirement plans, we do we should
00:09:10
measure them in decades. They are these kind of metaphorical uh aircraft carriers, right? That are slow to gain
00:09:15
momentum, slow to change direction, slow to do just about everything, but yet also very powerful over the long run.
00:09:22
And so for just about every aspect of our financial plans, we can and should take our time with these decisions. And
00:09:28
these risks that I talk about today and and the responses are something that perhaps you should take under
00:09:33
consideration, you should think about, but I don't want you to think that there's some sort of burning fire that
00:09:38
you must address today. So with that preamble, let's discuss our first risk,
00:09:43
longevity risk. Again, to me, the biggest, most obvious retirement risk that I can think of, it's the risk that
00:09:48
you live so long for one reason or another, that you run out of money. That you built a retirement plan, assuming
00:09:54
you'd live until age 75, but then you end up living to age 95. Now, the real
00:09:59
nasty part about longevity risk is that it's it's a risk magnifier. It's not
00:10:03
just about how long you live. It's really about how that extra decade or extra two decades of life interact with
00:10:10
many of the other risks that we've talked about today. Inflation, market volatility, health care costs, changing
00:10:15
spending patterns, etc. So longevity can sometimes magnify your exposure to the other risks. Nevertheless, let's talk
00:10:22
about some of the smartest financial planning strategies to mitigate and combat longevity risk specifically. So
00:10:27
here in the USA, every retiree, at least every retiree who's worked at least 10
00:10:32
years contributing into the social security system, every retiree has social security available to them. And
00:10:38
every retiree who has that social security available to them can choose to delay social security to age 70. That
00:10:45
is, in my opinion, the biggest single way to combat longevity risk. For a quick numerical example to explain that,
00:10:52
let's compare someone who claims social security at age 62 versus 67 versus 70.
00:10:57
And then let's think about longevity. So if we're talking about longevity risk,
00:11:00
we should probably think about someone who lives a long time. So for this example, they'll live to age 90. Now
00:11:05
using typical social security benefits, for those of you listening right now, a normal average scenario would see
00:11:10
someone claiming at age 62, they might collect $610,000 between age 62 and age 90. If they
00:11:18
delay, if that same person based on that benefit size, if they delay social security until age 67, they would
00:11:24
collect $720,000 by age 90. And if they delay claiming until age 70, they would collect
00:11:31
$780,000 by age 90. Now, so that's, you know what, between the worst case collecting at age 62 and the best case
00:11:38
collecting at age 70, that was a $170,000 difference in in how much they collected
00:11:44
over those years. And if this person lives to age 100, the total difference in benefits between the two claiming
00:11:50
strategies could easily surpass $300,000. Now, that's guaranteed income. Guaranteed income from social security.
00:11:57
It's a fantastic tool for longevity insurance for most retirees. But what else could we do? Well, we can also
00:12:04
build growth and inflation protection into the assets that we own. Now, the problem with that particular answer is
00:12:11
that growth and inflation protection aren't ever truly guaranteed. It's never
00:12:16
like a silver bullet. The assets I'm talking about here, for example, would be stocks. Stocks have a a great kind of
00:12:22
growth engine built into them that if you're diversified enough, should kind
00:12:25
of float on the rising tide of inflation over time. That's the way that stocks
00:12:30
behave. Real estate the same way. TIPS, which are Treasury inflation protected securities, have a small measure of
00:12:37
inflation protection built into the products themselves. And history would tell us that these assets hold up well
00:12:42
over the long run, even in the face of inflation. And to me, most of the time, that's kind of the best that we can do.
00:12:48
We use history to guide us into the future. But that's not quite a guarantee, at least not in the same way
00:12:53
that social security benefits are a guarantee. You could choose to also look at simple annuities here. Something like
00:12:59
a SPIA, a single premium immediate annuity. Or some retirees also like using a MIGA, a multi-year guaranteed
00:13:06
annuity, similar to a SPIA, but usually only lasts up to 10 years. Now, on episode 131, I recorded a deep dive on
00:13:12
annuities, including why most annuities in this world, I think are not good for investors like us. But I also admitted
00:13:19
in that episode that there are some annuities, including SPIA, including MAS, that at the very least I would
00:13:24
qualify, classify as acceptable. I don't know if I'll ever recommend one, but I'
00:13:29
I'd understand if someone chose to buy one. And the reason is that SPIA especially provide longevity insurance.
00:13:36
They provide guaranteed income for life. Now, most of us will die early enough such that the SPIA math does not work in
00:13:43
our favor. But some of us will live long enough to see the SPIA fundamentally improve our retirement finances. That's
00:13:49
how insurance products work, right? Most of us buy insurance and we don't get as
00:13:53
much money out of it as we put in. It's a losing deal for us. But for some people, insurance tends is a winning
00:13:59
deal. It saves their lives in some way. And annuities are that. What are they insurance against? Longevity risk.
00:14:05
Annuities are longevity insurance. Now, as for the rest of what we can do to combat longevity risk, it really
00:14:12
involves talking about some of the other risks. It talks about battling inflation, battling sequence of returns,
00:14:17
choosing spending and withdrawal flexibility, building protection for long-term care costs. But if there's one
00:14:22
major risk I think most retirees should focus on, it's longevity risk. Here's a
00:14:27
quick ad and then we'll get back to the show. I send a free weekly email to thousands of readers that shares two
00:14:32
simple things, just two. The first are my new articles and podcasts, so you'll
00:14:36
never miss when I publish new content. And the second is my favorite financial content from other corners of the
00:14:41
internet, so you can see what's been helping me the most. But Jesse, I don't
00:14:45
want another email. >> I hear you. I make this newsletter short, sweet, and full of essential
00:14:50
information, and readers enjoy that. About 85% of newsletter subscribers are engaging with the newsletter more than
00:14:55
once a month. They're enjoying it, and you will, too. You can subscribe for free on the homepage at
00:15:00
bestinterest.blog, blog and you'll get a free PDF of my white paper titled the
00:15:04
step-by-step guide to building your retirement paycheck. That's right, a free weekly email that thousands of
00:15:09
people like you are already reading, a free white paper to help you plan for retirement. And you can sign up for free
00:15:15
at bestinterest.blog. And that brings us to our second risk, inflation risk is the second one I want
00:15:21
to talk about. Inflation again is this everpresent phenomena in modern economies, meaning today's dollar will
00:15:26
lose spending power over time. And combined with living longer than expected, inflation risk means our
00:15:32
current dollars simply won't go far enough into the future to meet our needs. Now, the number one tactic, I
00:15:38
think, to combat inflation risk is to own assets that traditionally outpace inflation and minimize your exposure to
00:15:44
assets that get decimated by inflation. Bonds and cash, for example, they get decimated by inflation. There's no sort
00:15:51
of inflation adjustment built into cash and bonds. But with stocks and the companies that stocks represent, there's
00:15:57
a natural pricing mechanism at play where the companies will slowly but surely increase their prices over time,
00:16:03
increasing their revenues over time, meaning that your returns as a stock owner have this kind of tether to
00:16:09
inflation rates. Think of it as a buoy that floats up and down with a tide. If inflation rates are just going up up up,
00:16:16
the tide's going up up up, stocks in general tend to rise with that that rising tide. But that brings up this
00:16:23
really amazing interesting thing about stocks and bonds in particular. And the amazing thing is there's no perfect
00:16:29
asset for our long-term needs. Stock returns cannot be relied upon in the short and medium-term. We must use a a
00:16:36
more dependable, less volatile asset for those short-term cash outlays. Cash or bonds are a suitable choice for that.
00:16:44
And we must accept the lower returns from those assets as a price to pay. And we also must accept that we we might
00:16:50
lose pays to inflation. We might lose some ground to inflation, I should say, at least over the short run if we're
00:16:55
holding cash and bonds to meet our short-term needs. That's just the price we pay. Nothing is free in the world of
00:17:02
investing. For higher growth, the cost is more volatility, but for greater stability, to meet our short-term needs,
00:17:08
the price is less growth. And so cash and bonds help us fight sequence of returns risk, which we'll get to in a
00:17:14
minute. Cash and bonds ensure our financial plan has this really strong foundation over the near-term and the
00:17:19
medium-term years, but cash and bonds also expose us to inflation risk. So, we need to find a balance between fighting
00:17:26
inflation risk and then fighting sequence of returns risk and fighting market risk. And my point is that I've
00:17:32
got 14 unique risks I'm talking about today and between today and next episode, I should say. And some of the
00:17:38
tools we use to fight risk Actually expose us more to risk B. And some of the tools we're going to use to fight
00:17:45
risk C expose us more to risk D. And a big part of financial planning is finding that right balance where how do
00:17:51
we in general kind of minimize our exposure across this broad spectrum of risks? How do we identify which of these
00:17:58
specific risks we're kind of uniquely most exposed to in our situation? Anyway, it's why I think it's such a fun
00:18:03
exercise. That said, you know, stocks aren't necessarily the only asset that
00:18:08
tends to be kind of inflationproof over time. real estate, infrastructure, commodities. Generally, these assets
00:18:16
have some sort of income stream connected to inflation or simply go up in value with inflation. Real estate,
00:18:22
infra, in infrastructure, and commodities. But I do have some issues with these assets, I will say. So, if
00:18:27
you're owning individual real estate, you're subjecting yourself to a really
00:18:30
big concentration risk and quite a bit of hassle usually. If you decide to own real estate through a REIT, a real
00:18:37
estate investment trust, well, in that case, your investment risk actually looks a lot more like equity risk like
00:18:42
the stock market, then it looks like real estate. So, that's not necessarily
00:18:46
what you're going for. With commodities, you're not really owning an income
00:18:50
producing asset. I think the only economic argument for owning commodities is that you'll keep up with inflation
00:18:55
itself, nothing more compared to stocks. I don't really like that trade-off. But
00:18:59
at the same time, there are many plenty of long-term investing ideas that include real estate, include
00:19:04
commodities, include other alternatives, and they look good over historical back
00:19:08
tests. So to each your own, to each their own on this topic. The point is that inflation risk is a real threat in
00:19:13
retirement, and you need to make sure that your financial plan combats that risk. And number three here, I want to
00:19:19
touch on partner risk or household risk or or stakeholder risk. And again, are you and your spouse, are you and your
00:19:25
kids, are you and whomever, are you on the same page? And could some sort of disagreement or maybe an untimely death
00:19:30
throw off your long-term plan, your retirement plan? I think about different ages, different lifespans, different
00:19:36
spending habits, different levels of financial literacy, different priorities in life. This risk is much less about
00:19:42
any sort of investment decision, but really mainly solely about communication and the financial plan itself. So, first
00:19:50
you need to plan for both lifetimes, not just average outcomes. I think it's
00:19:53
important that you need to plan out and model a scenario where maybe one spouse lives significantly longer than the
00:19:59
other. Especially important if there's an age gap, if there's a health difference. It ensures that the
00:20:03
surviving partner doesn't run out of money later in life. And you also need to model out the the widow widowerower
00:20:09
scenario because you know what happens financially when one person dies. Some key things to evaluate could include a
00:20:15
loss or reduction of income because pensions might cease to exist or might be diminished after the pensioner passes
00:20:22
away. Social Security benefits can change a lot before and after a death. Changes in expenses are a major one,
00:20:29
right? Some expenses might drop away when one partner dies, but some expenses don't go away at all. There's some
00:20:34
pretty good stats out there that suggest that if the average married couple is spending 100%. Then after the first
00:20:40
partner dies, the surviving spouse is still probably spending somewhere between 60 and 70%. Because some
00:20:47
expenses don't get cut in half when one partner dies, they they remain the same.
00:20:51
Tax filing status is a big one, right? Filing jointly is more efficient than filing single. And after uh the first
00:20:58
spouse dies, I believe that the surviving spouse has a a full year to file jointly still, but then they have
00:21:05
to start filing single and that's less efficient than filing jointly. So these
00:21:09
kind of things, these issues are common points of failure, at least common points of inefficiency in otherwise
00:21:14
solid financial plans. Next, I think it's important that both partners truly
00:21:18
understand the plan. You know, a classic risk is that one person runs everything,
00:21:22
runs all the numbers, and the other partner says, "Yeah, well, I trust you.
00:21:25
You're the finance person. and you're the money person. But I don't like that.
00:21:29
I think both partners at least ought to know where assets are held, how income is being generated, or really what I
00:21:35
should say is kind of like how the retirement paycheck, so to speak, is being created, who to call for help. I
00:21:40
don't think that both partners have to be deep experts. That's maybe unrealistic, but you don't want one
00:21:45
partner to feel totally financially lost. Next, I think that every retirey couple should be on the same page about
00:21:51
spending. What's essential spending? What's flexible spending? How might you
00:21:55
adjust spending in bad market conditions? What does that cut back kind of look like? Because spending, as we'll
00:22:01
get to in in a few minutes, spending leads to withdrawing, withdrawal rates. Withdrawal rates are a slippery slope
00:22:06
toward heightened retirement risk. There's some other, you know, aspects of financial plans that are less have to do
00:22:11
with numbers, more have to do with documentation that both partners ought to know. updated wills and estate
00:22:16
documents, powers of attorney, beneficiary designations, clear account titling, and then you might not want to
00:22:22
always figure this out alone. Even if you are the most hardcore DIYer, your spouse might not be. So think about
00:22:28
building some sort of circle of trusted adviserss or at least trusted contacts. Whether it's an estate attorney, a
00:22:34
financial planner, an accountant, a trusted family member. The key is to have a surviving partner to have
00:22:40
hopefully somebody in the loop who they already know and trust. You know, there's a a decentsized list. Maybe I'm
00:22:46
I'm a little surprised by how long the list is, but there's a decent sized list
00:22:49
of listeners like you who have written to me with a perfectly nice email saying, "Jesse, I'm a DIYer. I plan to
00:22:55
be a DIYer until I die, but I told my spouse to call you when I die." Well,
00:23:00
thank you very much. That's an honor. I will say at times it might be important
00:23:03
to start those kind of conversations before death just to establish a little bit of a trusting relationship and maybe
00:23:09
get some ideas for improvement in place earlier rather than later. But the point
00:23:13
is that uh you don't want to overexpose yourself or your family to this partner
00:23:17
risk, household risk, stakeholder risk. Whether it involves one person dying sooner than anticipated, whether it
00:23:24
involves one person having all the information and the other person having none of the information, or maybe it
00:23:28
just involves disagreements between how the two of you want to approach your your spending, your investing, how you
00:23:33
approach the money side of retirement. Partner risk is a really big one that you want to mitigate over the long run.
00:23:39
Next up, number four on our list is market risk. In a very general sense, market risk is the idea that investments
00:23:45
can go down in value. Meaning that there's a risk that investments hurt you more than they actually help you. And
00:23:51
market risk is in a very kind of dictionary definition kind of way. It's a risk that you cannot diversify away
00:23:57
entirely. Market risk is the price of admission for long-term investing. If you want the long-term returns that the
00:24:03
market has to offer, you have to accept that sometimes those markets will fall. So, the goal isn't to eliminate market
00:24:10
risk. It's to survive market risk, to avoid being totally undone by market risk. And some of you might think, well,
00:24:16
market risk, sure, this is why I diversify, isn't it? This is why I I diversify my assets. And and yes, you
00:24:21
want to own thousands of stocks across different industries, geographies, market caps, etc. And that reduces the
00:24:27
risk that any one company's failure will derail your plan. But you still face
00:24:31
market risk. Even diversified stock portfolios drop by large amounts with, in my opinion, unsettling frequency.
00:24:37
Diversification means that you avoided kind of additional unnecessary risks, but you cannot diversify away market
00:24:43
risk. So to truly kind of defeat market risk, I think the first thing you need to realize is that time is your biggest
00:24:49
ally. Time. If you need money in two years, the stock market is a dangerous place to be. But if you need money in 20
00:24:56
years, the stock market's volatility really becomes your friend. Market risk
00:25:01
can be totally eliminated or very close to totally eliminated as long as you're
00:25:05
not forced to sell your stocks at the worst times. I think you can and should rebalance to combat market risk. That's
00:25:12
a big tool that you can use in your favor is rebalancing. I spoke about this in depth on episode 138. Generally, as
00:25:18
the stock market rises, especially as it rises quickly, market risk increases. Rebalancing though forces you to sell
00:25:26
what's gone up and buy what's gone down, thereby reducing your exposure to market
00:25:31
risk. A dollar cost averaging helps combat market risk, too. So whether you're in accumulation mode or de
00:25:37
accumulation mode, dollar cost averaging money in or out of the market helps diversify your your market risk through
00:25:42
time. diversifying through time over time. Dollar cost averaging, it smooths out the various entry and exit points
00:25:48
with money going in and out of your portfolio, and it decreases the likelihood that you'll need to sell or
00:25:53
buy some big dollar amount of of investments at the quote unquote wrong time. And last, I would say that that
00:25:59
the pain of market risk is almost always, not always, but is almost always accompanied by bad investor behavior.
00:26:06
And again, it's not that market risk itself has to be incorporated with bad behavior. It's that feeling, the pain,
00:26:12
actually recognizing the downside of market risk is almost always due to bad investor behavior. So that's selling
00:26:19
during a panic, right? That's chasing performance. It's abandoning your your
00:26:23
predetermined plan. Plans and portfolios fail if the investor can't stick with
00:26:28
them. So again, market risk. Market risk isn't a bug. It's a feature that creates
00:26:32
returns. It's everpresent. We all face it. If markets were stable and predictable, then returns would be
00:26:38
lower, right? That's just a the fact of how markets work. So market risk and
00:26:42
then volatility, we want it really and it's the cost that we pay for long-term
00:26:47
growth. That's market risk. Here's a quick ad and then we'll get back to the
00:26:51
show. I love getting your questions and some of you ask me questions about the wealth management firm I work for in
00:26:55
Rochester, New York. Others ask about the best interest blog and this podcast, Personal Finance for Long-Term
00:27:00
Investors, which operate without advertising, without pushy sales, and with no payw walls. How can the blog and
00:27:05
podcast stay afloat without me dumping my own money into it? Well, to answer both those questions, I want to point
00:27:10
you to episode 78 of Personal Finance for Long-Term Investors. I intentionally recorded episode 78 to shine light on
00:27:16
those topics and inform you how you are actually helping and can continue helping these projects carry forward.
00:27:22
So, if you've ever been curious about the business of my blog and podcast, or
00:27:26
if you're curious about my day job in wealth management, please check out episode 78 and let me know what you
00:27:30
think. Next up, number five on our list here is sequence of returns risk, which is a particular type of market risk. So
00:27:38
even if your investments go up over the long run and even if market risk is something that you can easily tackle
00:27:43
behaviorally, if your investments go down too early in your retirement, it can create this chain reaction that you
00:27:49
never really recover from. So I'm going to borrow from what I discussed in episode 126 because I have discussed
00:27:55
sequence of returns risk a bunch. We also did a deep dive on sequence risk back in episode 87 and I'll link another
00:28:01
article in the show notes about the the interaction between sequence risk and uh
00:28:04
required minimum distributions RMDs. For those unfamiliar, I think the one sentence definition of sequence risk is
00:28:10
that bad market performance hurts you disproportionately more in the early years of retirement than in your later
00:28:15
years such that we all carry a risk that our retirement will suffer an unlucky streak of bad returns early on
00:28:21
potentially derailing our long-term retirement dreams. Yes, that was one run-on sentence. So, let's talk about
00:28:27
how much it matters how sequence risk actually declines in time and what you can do to protect those early years. So,
00:28:33
in Wade Fowl's book, Retirement Planning Guide book, he attempts to quantify the
00:28:36
magnitude of sequence risk yearbyear leading into retirement. And we'll throw
00:28:40
a link to to Wade FA's chart into the show notes. And my takeaway from the study is this. The first six years of
00:28:46
retirement carry more sequence risk than any pre-retirement year. and Wadefoul study looked at a 60-year period 30
00:28:53
years before the retirement date, 30 years after retirement to evaluate each year's relative impact on final
00:28:59
portfolio value. So again, the first six years of retirement carry this really significant sequence risk and the first
00:29:05
year carries the most risk by far with each subsequent year falling off pretty significantly. And by the time you're at
00:29:11
year 10 of retirement, your sequence risk is actually far lower than it was for the entire decade before you
00:29:17
retired. Or put another way, if you're listening to this and you've been
00:29:20
retired for more than 6 years, I'd feel pretty great about that. If you've been
00:29:24
retired more than 10 years, you should feel really great about that. But going back to today's topic, thinking about
00:29:29
this risk, the risk itself, and how do we mitigate this risk? What do we do about sequence risk? In my mind, it's
00:29:35
actually pretty simple because as I've mentioned before, sequence risk is not
00:29:38
just a function of market returns. Of course, it is a function of market returns. It's also a function about how
00:29:43
much money we withdraw when our assets are depressed. Selling our assets when they're down 40% off their all-time high
00:29:50
will cause a major sequence pain in our retirement plan. And that's why we want
00:29:54
to build in some sort of safer or non-correlated assets into our retirement portfolio. In an ideal
00:30:00
scenario, it might look like well, it could look like a bunch of different things, but one example could be 6 to 12
00:30:04
months of pure cash, 2 to 3 years of short duration bonds, another 2 to three years of longer duration bonds. And when
00:30:11
we zoom out, we see right there, you know, five, six, seven years of spending in cash and relatively low-risk bonds.
00:30:18
And that should get us through most of that really risky sequence window. And most retirement portfolios, or at least
00:30:24
many retirement portfolios, already have this. So if you're entering retirement
00:30:27
with say 30% or more of your portfolio in cash and bonds, 30% or more, you almost certainly have at least 6 years
00:30:35
worth of spending right there in cash and bonds. Now, if you're retire entering retirement with 20% or 10% or
00:30:42
barely anything in cash and bonds, well, then you might have to make a hard decision because on the one hand, if you
00:30:48
own 100% stocks, let's say, you're not really that exposed to inflation risk,
00:30:52
and good for you, but you're very exposed to sequence of returns risk. And this goes back to that trade-off I was
00:30:57
talking about earlier. You've decided to combat risk A, but you're exposing
00:31:01
yourself to risk B. So the question for you is, do you intentionally accept the lower expected returns of cash and
00:31:08
bonds? Do you intentionally accept a little bit of additional risk exposure to inflation risk, but in order to
00:31:15
dissipate your exposure to sequence risk? Financial planning is chock full of those types of trade-offs. And
00:31:21
financial planning is also all about understanding and at least somewhat decreasing your range of potential
00:31:27
outcomes. So, here's a situation where if you're entering retirement with 100%
00:31:31
stocks, I would wager that rebalancing a little bit to give yourself some way to
00:31:37
combat sequence risk by adding some cash or bonds to your portfolio is probably is usually going to be a beneficial
00:31:44
trade-off for you. So, those are my thoughts on sequence of returns risk and how we can combat it. Our next risk
00:31:49
number six is withdrawal risk. you're simply withdrawing too much money too quickly, which most of the time I will
00:31:55
say is simply hidden language for you're spending too much money or it could be
00:32:01
hidden language for you didn't have enough money to retire in the first place. I I don't really think that
00:32:05
there's a big secret here when it comes to withdrawal risk. But as I said before, measuring your cash flow, right,
00:32:11
measuring the money that's coming into your life and going out of your life is
00:32:14
a simple lowhanging fruit that all of us can do. And yes, it can be a little tedious. It can be a little annoying.
00:32:20
There's a reason why I should say some people find it challenging to measure
00:32:23
their cash flow. Budgeting is a curse word to them. We're talking about the same thing here. But avoiding that
00:32:29
exercise, avoiding the measurement of your cash flow can lead to big retirement issues. The solution for
00:32:36
withdrawal risk is to stop withdrawing such large percentages of your portfolio every year. And one way to do this is by
00:32:42
spending less. Another way to do it is by increasing the cash that's coming in
00:32:46
the door, which might look like a part-time job. Another way to do it is by not retiring in the first place,
00:32:51
choosing to work a few more years and actually adding more money to your portfolio by saving than taking money
00:32:56
out by withdrawing it. And I realize that none of those solutions are too exciting. They aren't. Right? If my
00:33:02
answer to your problem is you got to spend less money, you got to get a part-time job. And actually, now that I
00:33:07
think about it, you shouldn't retire in the first place. Nobody wants to hear
00:33:10
that news, but that's at times the simple reality and the simple arithmetic of certain financial situations. But
00:33:16
withdrawal risk is a a serious risk in retirement and one that again there aren't really any silver bullets against
00:33:22
it. It's just some simple arithmetic about how do you take less money out of
00:33:26
your portfolio on an annual basis, but it's certainly something you need to be
00:33:29
aware of. And that brings us to the last risk number seven for today's episode.
00:33:34
Health risk. In a general sense, health risk. I think to myself, will you find yourself at 70 years old too weak or too
00:33:41
sick to hop on a plane to play with your grandkids or live whatever version of active retirement that you've been
00:33:46
hoping for? I'm not even focusing on the possible expenses of health issues right
00:33:50
here. I'm not even thinking about dying early right here, although those are
00:33:54
both serious risks worth considering. I'm just thinking about pain and suffering. I'm thinking about the loss
00:33:59
of lifestyle flexibility. Again, no longer able to sit in a car for 4 hours or pick up your grandbabies. There's
00:34:06
nothing financial we can really do when your body betrays your wishes. That's
00:34:10
kind of a scary thought. At least I I think it is for me. I know nothing about health in any sort of real capacity. So
00:34:16
So what follows here is mostly me just paring what other experts have to say or just kind of doing that anecdotal health
00:34:23
talk that some of us tend to do. It does seem from what I've read from some real
00:34:26
experts who know what they're talking about. It does seem that the biggest weapon we have against health risk
00:34:31
because that's what we're here to talk about. The biggest weapon against health
00:34:34
risk is to invest in your own health early and often. Simple things, exercise, nutrition, sleep, preventative
00:34:41
care, they're more than just lifestyle choices. We can and I think we should
00:34:45
think of them as the pseudo financial strategy. Certainly something that aligns perfectly with the topics that we
00:34:50
talk about on this podcast. In fact, episode 79 and episode 122, Dr. or Phil Pearlman stopped by to talk very
00:34:57
specifically about the intersections of wealth and health. Now, what does it actually mean to invest in your health
00:35:03
early and often? Which exercises are best? Which diet? How much sleep do you need? Those topics I'm way out over my
00:35:08
skis. I'm not going to pretend to prescribe to you good exercises, good diets, and how much sleep you need. But
00:35:14
I think it's worth asking yourself about what exercises, what diet, and how much
00:35:19
sleep you ought to be getting. There is something though that I go back to. I I think of it as the thousand person test.
00:35:25
It's very basic. Imagine we have two groups of 500 people each. So a thousand
00:35:29
people in total. Group A, those 500 people are what we'll call super healthy. Group B is what we'll call
00:35:35
unhealthy. So group A, they eat really well, they stay active, they get good sleep, they have positive relationships.
00:35:42
Group B is just the opposite on every metric. And then I think will there be some members of group A, the healthy
00:35:48
group, where they end up in a place where surprisingly they have some bad health outcome like cancer or dementia
00:35:54
or heart disease. The answer is probably after all 500 people is a lot of people
00:35:58
and some of them will have some bad outcomes. And then I think about group B and will some members of group B end up
00:36:03
in a place where surprisingly they actually have a good health outcome? They live until age 95 and they die of
00:36:08
natural causes and everything is fine. Well, probably because there's 500 of
00:36:12
them and it's a lot of people. the law of large numbers, there are going to be
00:36:15
some outliers. But if you measure outcomes across the entire group, I am willing to say despite my total lack of
00:36:21
medical expertise that group A is going to look way better and we all are going to wish we could end up in group A. So I
00:36:28
think it reframes our question a little bit. It's not necessarily, you know, how
00:36:32
do I make sure I avoid a heart attack? How do I make sure I avoid dementia? I mean, of course, if there were again
00:36:36
silver bullets, we probably ought to be taking those silver bullets, but I'm not
00:36:41
sure there are. I think therefore the question that at least I ask myself is what would a person do to end up in
00:36:46
group A? And when should that person start working toward ending up in group A? And as I've moved through life and
00:36:53
interacted with more and more people in their 60s and 70s and 80s, I just find it so fascinating that some people they
00:36:59
haven't even claimed their social security yet. That's how young they are.
00:37:02
But you can see their labored movements or their fatigue, their loss of independence, their cognitive fog, and
00:37:08
that's a little heartbreaking. And then there are people who are 85. They're
00:37:11
still moving around well. They've got presence and and posture and mental acuity and sharpness, and that's amazing
00:37:18
to see. And so, while we're here talking about finances, ask yourself, would you
00:37:23
rather have an A+ financial plan combined with a a D on physical health? Is that something you want? Or if you
00:37:30
had to refocus some of your time and energy and and resources, would you rather be willing to dial down your
00:37:36
finances to a B+ if it meant bringing your health up to a B+? Now, obviously, this isn't a game where we simply get to
00:37:43
dial our attributes up and down, but my point is that retirement is about more than just finances. Health risk, which
00:37:50
yes, is a cousin of longevity risk. To be sure, it should be one of the more important risks that you choose to steal
00:37:56
yourself against. Your 3% withdrawal rate means very, very little if you're dead at 68 years old, or even if you're
00:38:02
just kind of semi-incapacitated at 68 years old. Wealth without health, I think, loses a lot of its luster. Again,
00:38:10
wealth without health loses a lot of its luster and we need to ensure that we're
00:38:14
doing what we can to minimize that health risk. So, thank you for listening. I'm going to pause here today
00:38:18
and I'll continue in our next episode covering long-term care risks, cognitive
00:38:23
decline risk, behavioral risk, assumptions risk, policy, legislation, and tax risk, identity and purpose risk,
00:38:30
and then the so-called deep risks. Thank you so much for tuning in to this episode of Personal Finance for
00:38:36
Long-Term Investors. Thanks for tuning in to this episode of Personal Finance for Long-Term Investors. If you have a
00:38:42
question for Jesse to answer on a future episode, send him an email over at his blog, The Best Interest. His email
00:38:48
address is [email protected]. Again, that's jessevestinterest.blog.
00:38:55
Did you enjoy the show? Subscribe, rate, and review the podcast wherever you listen. This helps others find the show
00:39:02
and invest in knowledge themselves, and we really appreciate it. We'll catch you
00:39:06
on the next episode of Personal Finance for Long-Term Investors. Personal Finance for Long-Term Investors is a
00:39:13
personal podcast meant for education and entertainment. It should not be taken as
00:39:17
financial advice and it's not prescriptive of your financial situation.

Episode Highlights

  • The Principle of Inversion
    Instead of asking how to succeed, consider how to avoid failure. This approach can reshape your financial planning.
    “What does failure look like and how can we avoid it?”
    @ 00m 12s
    May 27, 2026
  • Understanding Longevity Risk
    Longevity risk is the danger of outliving your savings, a critical concern for retirees.
    “Longevity risk is the biggest, most obvious retirement risk.”
    @ 09m 47s
    May 27, 2026
  • The Role of Annuities
    Annuities can provide guaranteed income for life, acting as a safety net against longevity risk.
    “Annuities are longevity insurance.”
    @ 14m 05s
    May 27, 2026
  • Understanding Inflation Risk
    Inflation risk can erode your purchasing power, especially in retirement. It's crucial to combat this risk.
    “Inflation risk is a real threat in retirement.”
    @ 19m 12s
    May 27, 2026
  • Partner Risk in Financial Planning
    Communication is key in financial planning to avoid partner risk, which can derail long-term plans.
    “You need to plan for both lifetimes, not just average outcomes.”
    @ 19m 50s
    May 27, 2026
  • Market Risk Explained
    Market risk is the inherent risk of investments losing value. It's a price of admission for long-term investing.
    “Market risk isn't a bug. It's a feature that creates returns.”
    @ 26m 30s
    May 27, 2026
  • Sequence of Returns Risk
    The first six years of retirement carry the most sequence risk, impacting long-term financial health.
    “The first six years of retirement carry more sequence risk than any pre-retirement year.”
    @ 28m 44s
    May 27, 2026
  • Withdrawal Risk Management
    Managing withdrawal rates is crucial to ensure financial stability in retirement. Spending too much can jeopardize your future.
    “Withdrawal risk is simply hidden language for spending too much money.”
    @ 31m 51s
    May 27, 2026
  • Health Risk in Retirement
    Health risk is a significant factor in retirement planning that often gets overlooked.
    “Wealth without health loses a lot of its luster.”
    @ 38m 08s
    May 27, 2026

Episode Quotes

  • How can I kill these pilots?
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140
  • Longevity risk is the biggest, most obvious retirement risk.
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140
  • Nothing is free in the world of investing.
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140
  • You need to plan for both lifetimes, not just average outcomes.
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140
  • Financial planning is chock full of trade-offs.
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140
  • It's a scary thought when your body betrays your wishes.
    The 14 Retirement Risks - And How to Combat Them (Pt 1) - E140

Key Moments

  • Inversion Principle00:12
  • Longevity Risk09:47
  • Inflation Risk19:12
  • Partner Communication19:50
  • Market Risk26:30
  • Sequence Risk28:44
  • Retirement Realities33:08
  • The Thousand Person Test35:20

Tension Over Time

Words per Minute Over Time

Vibes Breakdown