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Longevity & Retirement | Jeremy Keil - E127

January 14, 2026 / 53:37

This episode of Personal Finance for Long-Term Investors covers retirement planning, fixed indexed annuities, and withdrawal strategies. Host Jesse Kramer is joined by Jeremy Kyle, author of Retire Today.

Jesse begins with a review of listener feedback and discusses the complexities and hidden costs of fixed indexed annuities, emphasizing their high commissions and limited upside potential. He warns listeners about the misleading sales tactics often used to promote these products.

Jeremy Kyle joins to discuss retirement longevity and common misconceptions about retirement age. He highlights the importance of understanding personal longevity estimates and the emotional hurdles retirees face, such as transitioning from saving to spending.

They also address social security claiming strategies and the significance of tax planning in retirement. Jeremy shares a five-step process for creating a retirement master plan, focusing on spending, income, tax efficiency, investing, and estate planning.

The episode concludes with Jeremy promoting his book and podcast, Retire Today, while encouraging listeners to take control of their retirement planning.

TL;DR

Jesse Kramer and Jeremy Kyle discuss retirement planning, fixed indexed annuities, and effective withdrawal strategies for retirees.

Video

00:00:00
Welcome to personal finance for
00:00:02
long-term investors, where we believe
00:00:04
Benjamin Franklin's advice that an
00:00:06
investment in knowledge pays the best
00:00:08
interest both in finances [music] and in
00:00:10
your life. Every episode teaches you
00:00:12
personal finance and long-term investing
00:00:14
in simple terms. Now, here's your host,
00:00:18
Jesse Kramer. Welcome to Personal
00:00:20
Finance for Long-Term Investors, episode
00:00:22
127. My name is Jesse Kramer. By day, I
00:00:25
work at a fiduciary wealth management
00:00:26
firm helping clients nationwide. You can
00:00:28
learn more at
00:00:29
bestinterinterest.blog/work. [music]
00:00:31
The link is in the show notes. And by
00:00:33
night, I write the bestinest blog and I
00:00:35
host this [music] podcast. I also put
00:00:36
out a weekly email newsletter, which as
00:00:38
of now uh just crossed 4,000 active
00:00:41
weekly readers did the newsletter and
00:00:43
and all those projects, the blog, the
00:00:45
podcast, and the newsletter, help busy
00:00:47
professionals and help retirees avoid
00:00:49
financial mistakes and grow their wealth
00:00:51
by simplifying their investing, their
00:00:53
taxes, and their retirement planning.
00:00:55
And today I'm going to focus this
00:00:56
episode on the act of retirement itself
00:00:58
in part today helped by the author of
00:01:00
the book Retire today and that author is
00:01:02
Jeremy Kyle. But first we'll do a quick
00:01:04
review of the week. This one comes from
00:01:06
CJ from NorCal Northern California. CJ
00:01:09
says, "Must read for financial
00:01:11
education." Maybe CJ means must listen,
00:01:13
but you know what? I write a blog, too.
00:01:14
So anyway, CJ says, "Jesse Kramer talks
00:01:16
personal finance in an easy to
00:01:18
understand, entertaining, and empathetic
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way that will get you thinking the right
00:01:21
way about your money choices. From the
00:01:23
teenager to the retiree, this should be
00:01:25
near the top of everyone's podcast
00:01:27
library." Well, thank you CJ very much
00:01:29
and I would be happy to send you a
00:01:31
Supersoft podcast t-shirt. Simply uh
00:01:33
email me jessebinest.blog
00:01:36
and we will get you hooked up with that.
00:01:37
And before Jeremy Kyle joins us today to
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dive into some of his favorite
00:01:40
retirement topics, I have a little
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monologue where I'm going to dive into
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some of my recent, you know, the little
00:01:46
corners of the retirement planning world
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that I've been diving into. And the
00:01:49
first one is from an article I recently
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wrote. And the article is called about
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that free steak dinner. We will include
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a link in the show notes. It was
00:01:57
inspired by a a reader named C. And and
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the short version of C's story is that
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she went to a lovely free dinner uh
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sponsored by a financial investment
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company who would like to take her
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traditional IRA and convert it to a Roth
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IRA via something called a fixed indexed
00:02:12
annuity. They would pay uh C a 17% bonus
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on her roughly $600,000 in traditional
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IRA and SE IRA and 401k and then over
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the course of 10 years they would
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convert that amount to Roth dollars
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keeping her income low enough to not
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trigger any sort of Irma increase and
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that's again their language to her and
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then as she understands it her only risk
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and this is again is her quoting the
00:02:35
financial institution here her only risk
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is the opportunity cost of not
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maximizing market gains and so see thank
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me in advance for any insights she was
00:02:43
willing to provide. Well, when I read
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what she had outlined, my my radar
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detector rapidly kind of wore to life,
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and I was getting ready to sound a loud
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red alert like they do on uh Star Trek:
00:02:53
The Next Generation.
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>> Red alert. All hands stand battle
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stations.
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>> So, first, let's define this lackluster
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tool. What exactly is a fixed indexed
00:03:03
annuity? A fixed index annuity, FIA, I
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I'll just call it a fixed index annuity.
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It's easier than probably saying FIA is
00:03:10
an insurance product that promises two
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things. First, it promises you principal
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protection that your initial investment
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can't lose value due to market declines,
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but then [snorts] it also promises you
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some upside potential because the
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returns of the annuity are tied to a
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market index, say like the S&P 500, uh,
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but only partially tied. So, here's how
00:03:29
it typically works. The insurance
00:03:31
company, they take your premium, your
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initial investment if you will, and they
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invest it conservatively, mostly in
00:03:36
bonds. Then they use some of the
00:03:38
interest earned from the bonds to buy
00:03:40
options, option products on a a market
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index like the S&P 500. If the index
00:03:46
goes up, you get a portion of that gain
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through something that's called a cap or
00:03:50
a participation rate. If the index goes
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down though, you earn zero. You don't
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lose money either, but you earn zero.
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So, it kind of sounds nice, at least the
00:03:58
way I've described it so far. There's no
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real downside. There is some upside, but
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as you might guess and as you might know
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from my previous episodes and previous
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blog posts and everything I really do, I
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think there are way more reasons to
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dislike fixed index annuities. The first
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one, the very high opaque costs. The
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commissions paid to salespeople of these
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products are often in the 6 to 10% range
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upfront, hidden from the investor. those
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costs are just baked into the product's
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kind of internal mechanics, resulting
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in, of course, a lower crediting rate
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and slower growth for the client. So,
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for this fixed index annuity that the
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original reader C was considering, the
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$600,000 in principle that she would
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have put into the product upfront
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probably would have resulted in a $35 to
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$60,000 commission for the salesperson.
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And that fact alone ought to give us
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some pause. It makes me think of that
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famous Charlie Munger quote, "Show me
00:04:52
the incentives and I will show you the
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outcome." If you're going to pay someone
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$50,000 to sell a product, they're
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really going to push that product
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probably whether it's a good fit for you
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or not. The second reason to dislike
00:05:03
these products is just the complexity
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and the confusion. I think the jargon
00:05:06
behind annuities is complicated, right?
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I've already used some of these words,
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cap rates, participation rates, spreads,
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reset periods, surrender charges, and
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and here's a quote from the annuity
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industry itself. One reason annuities
00:05:19
can be confusing is that the language
00:05:20
used is often complex and technical. The
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Alliance for Lifetime Income, that's a
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industry organization, learned that the
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current jargon makes most consumers feel
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confused and disengaged. In response,
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the Alliance for Lifetime Income,
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created a plain language annuities
00:05:37
language glossery to help you better
00:05:39
understand the beneficial retirement
00:05:40
income option. In other words,
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everybody's confused by the language,
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including many professionals. the
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numbers and then the way those numbers
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interact. It's usually much more
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complicated than the jargon. And that's
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a problem, too. Every annuity uses its
00:05:53
own verbiage in unique ways and then
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combines confusing semantics with
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actuarial math. It's nearly impossible
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for a lay person to fully understand
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what they're getting. It's often
00:06:02
impossible for financial professionals
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to understand what some other person's
00:06:06
annuity was. I think that complexity, it
00:06:08
hides the fees and it hides the the
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limits, the upper limits of what these
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products can do. I've had to work with
00:06:14
people looking to unwind these annuities
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and I I just simply detest how complex
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they are. I'd like to think that I can
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understand complex things and even I
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oftentimes struggle unless I really
00:06:25
really really dive into the details to
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understand what is going on under the
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hood of these products. My third reason
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for disliking them, limited upside. The
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fact that a fixed index annuity is
00:06:34
market linked is a misleading promise.
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If the market grows by 15% and your
00:06:38
fixed index annuity has a 6% cap, well,
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you only see 6% of the 15% growth. Now,
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they're sold as market linked to make
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you think you're getting a real shake at
00:06:47
the market growth. But over time, these
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products really lag behind market growth
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by a significant margin. The fourth
00:06:53
reason to dislike them, liquidity traps.
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Most of them lock up your money for 7 to
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10 years before you can annuitize them
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and start to live off of an income
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stream. And if you want out early,
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you'll face some sort of heavy surrender
00:07:03
penalty in addition to that 6 to 10%
00:07:06
commission you paid up front. This
00:07:07
inflexibility just it runs counter to
00:07:10
sound investor centered financial
00:07:12
planning. Fifth, I already referred to
00:07:14
this one, the misaligned incentives,
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annuities are often sold, not bought nor
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advised. And because of those big
00:07:20
commissions, many non-fiduciary
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salespeople pitch them aggressively to
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retirees seeking safety, sometimes
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overstating the returns of the product
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or understating the downsides. So, one
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thing I haven't even talked about yet,
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and now we're going to pivot back to C's
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specific question. What about that whole
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annuity plus Roth conversion thing she
00:07:38
was mentioning, if you recall, she said
00:07:40
she was sold the idea of a fixed index
00:07:42
annuity in particular for using it as a
00:07:44
vehicle for a Roth conversion. And there
00:07:46
are some other sales language in there,
00:07:48
too, which I'll address first. She was
00:07:50
promised a 17% bonus. The bonus isn't
00:07:53
free money. It's not even real money. It
00:07:54
sounds amazing, of course, but that's
00:07:56
the headline they use to hook people. A
00:07:58
real 17% bonus would result in actual
00:08:01
money sitting somewhere in an account.
00:08:02
But this bonus that is often tied to
00:08:04
annuity products, it is not a cash
00:08:06
bonus. It's a contract value credit that
00:08:09
only applies to income calculations
00:08:11
after the 10-year holding period, not to
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the actual account value that you could
00:08:15
walk away with today. That 17% bonus is
00:08:18
therefore offset by lower caps on your
00:08:21
returns over the next 10 years. Right?
00:08:23
Your index growth gets throttled down.
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It's offset by longer surrender periods
00:08:28
like the 10 plus year uh surrender
00:08:30
periods that are very common or it's
00:08:32
offset by reduced liquidity, right? You
00:08:34
can't easily access your money without
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penalties over this long 7 8 10 year
00:08:38
period. You've got really high annual
00:08:40
fees going on at the same time too. That
00:08:43
17% bonus pretty quickly gets eaten
00:08:45
away. And like I said, besides, it's not
00:08:47
a lump sum bonus. It's it's a uh a
00:08:50
crediting bonus on the income that
00:08:52
you'll collect a decade from now. My
00:08:54
second issue that the 10-year Roth
00:08:55
conversion plan certainly sounds smart,
00:08:58
but it's also structured to benefit the
00:09:01
annuity company, not the client, not the
00:09:03
investor. A a gradual Roth conversion
00:09:05
over time certainly can be a smart thing
00:09:07
to do by spreading your tax payments out
00:09:10
over time to avoid jumping into higher
00:09:12
tax brackets or sure to avoid triggering
00:09:15
Irma, but a fixed index annuity isn't
00:09:17
needed to do that, right? You can hold
00:09:19
investments in a simple lowcost IRA and
00:09:22
still control the pace of your Roth
00:09:24
conversions every year. They don't care
00:09:26
about the Roth conversion. They care
00:09:27
about locking your money into their
00:09:29
product. That's why they suggest the
00:09:31
10-year timeline, right? It's a trap,
00:09:33
just like in Star Wars. It's a trap. It
00:09:35
It's a trap that pays the agent a large
00:09:37
commission and keeps you from easily
00:09:39
changing course once you realize how
00:09:41
limiting the contract is. Point number
00:09:43
three, and this is one thing that C
00:09:44
wrote to me where she said, "I think the
00:09:46
only thing going on here, Jesse, the
00:09:47
only risk is opportunity cost, and that
00:09:49
is the sales line, but it's misleading
00:09:51
because the real risks include liquidity
00:09:53
risk, complexity risk, right? You may
00:09:55
not understand how the product works
00:09:56
until it's too late, return risk, of
00:09:58
course, right? These fixed index
00:10:00
annuities just lag simple 60/40
00:10:02
portfolios by a lot every year. And then
00:10:05
inflation risk, the returns might not
00:10:07
even keep up with the cost of living."
00:10:09
And the fourth issue is the the Roth
00:10:11
angle. Again, it's a smoke screen. The
00:10:13
sales pitch uses Roth conversions to
00:10:15
sound like they're doing careful tax
00:10:16
planning, but the fixed index annuity
00:10:18
company isn't optimizing your taxes.
00:10:20
They're selling a contract. A real tax
00:10:22
planner could help you do the same Roth
00:10:23
conversions without all the added costs
00:10:26
or restrictions. So, the bottom line is
00:10:28
that you can absolutely do a multi-year
00:10:30
Roth conversion strategy. You just don't
00:10:32
need a fixed index annuity to do it.
00:10:34
Adding one into your retirement often
00:10:36
makes things worse, not better. Again,
00:10:38
annuities are sold. They're not bought.
00:10:40
And so for some people, see, that steak
00:10:43
dinner you attended might have been the
00:10:44
most expensive free steak dinner of your
00:10:47
lives. I know this might sound like
00:10:48
scary fear-mongering, and yeah, I
00:10:50
apologize for that, but I think it would
00:10:52
be scarier if you said yes to buying one
00:10:54
of these products. And last, uh, before
00:10:56
Jeremy joins us, I'm going to read from
00:10:58
another article, and the the the title
00:11:00
of this article is pretty
00:11:01
straightforward as to what the topic
00:11:02
will be about. It's, "Are dividends and
00:11:04
income part of my retirement withdrawal
00:11:07
rate or my safe withdrawal rate?" And
00:11:09
again, this comes from a question from
00:11:10
Barry. Barry said, "Jesse, I'll need
00:11:11
about $100,000 per year for my portfolio
00:11:14
in retirement. I currently have $3
00:11:16
million in my retirement portfolio. It's
00:11:18
producing about $60,000 in income and
00:11:20
dividends per year for me, meaning I
00:11:22
only need to sell about $40,000 net of
00:11:25
taxes of the principal value to fund the
00:11:27
rest of my need." And again, listeners,
00:11:29
that's $60,000 in income and dividends
00:11:31
and then $40,000 in actual sales of the
00:11:34
investments. And uh Barry says, "By my
00:11:36
math, the $40,000 that I'll need to sell
00:11:39
divided by the $3 million portfolio
00:11:42
value, that's about 1.3%." In other
00:11:44
words, his withdrawal rate is way less
00:11:46
than the four 4% rule, right? It's 1.3%,
00:11:49
not 4%. Barry says, "Am I thinking about
00:11:51
this correctly?" So, we we are going to
00:11:53
answer this question. We are going to
00:11:54
let Barry know if he's thinking about
00:11:55
this correctly. I won't bury the lead.
00:11:57
He's not actually thinking about it
00:11:58
correctly. And so, we'll point out why.
00:12:00
But before answering Barry's question,
00:12:01
we have to ensure we're all on the same
00:12:03
playing field. So, first, the 4% rule.
00:12:05
If you're not familiar with the
00:12:06
nitty-gritty details of the 4% rule, uh,
00:12:08
I've got some excellent primers that we
00:12:10
will link in the show notes for you.
00:12:12
Some stuff about the basics, what the 4%
00:12:14
rule is based on, uh, why many people
00:12:16
are using the 4% rule wrong. We talk
00:12:18
about is the 4% rule too risky. We talk
00:12:20
about all the conservatism that's built
00:12:22
into the 4% rule and why actually, uh,
00:12:24
you know, many retirees, if you, uh,
00:12:26
look at historical back tests, could get
00:12:28
away with four and a half, five, five
00:12:30
and a half, six% withdrawal rates,
00:12:32
something like that. So, I won't dive
00:12:34
too much into that topic right now. It's
00:12:36
just worth understanding what the 4%
00:12:37
rule is if you're not familiar. What's
00:12:40
more interesting and getting really to
00:12:41
the point of today's question, let's
00:12:43
talk about where investment returns come
00:12:45
from. No, this isn't the kind of
00:12:46
question that children ask their parents
00:12:48
and involve storks, we need to discuss
00:12:50
where investment returns come from.
00:12:52
Where does the growth come from? If you
00:12:54
own stocks, if you own bonds, if you own
00:12:55
real estate or anything else, how does
00:12:57
that return on investment end up in your
00:12:58
pocket? The answer of course is
00:13:00
different for each investment class, but
00:13:02
most investments provide their return to
00:13:04
investors via two separate mechanisms.
00:13:06
The first mechanism is that they
00:13:08
regularly return some sort of cash flow
00:13:10
to their investors. It could be interest
00:13:13
from a bond. Could be a dividend from a
00:13:15
stock, which is really like profit from
00:13:17
a stock, right? I should say interest
00:13:19
from a bond is because you lent someone
00:13:21
your money and now they're paying you
00:13:22
interest. A dividend from a stock is
00:13:24
because you own a company. that
00:13:26
company's making profits and they give
00:13:28
you some of those profits as an owner.
00:13:30
If you own real estate, you might be
00:13:32
charging rent and you're collecting some
00:13:33
of that rent, you know, net of any
00:13:35
expenses as the owner of the real
00:13:37
estate. So the point is that investments
00:13:39
oftent times return cash to their owners
00:13:42
in some way. But then the second
00:13:43
mechanism is that the investment itself
00:13:46
appreciates in value over time. This
00:13:48
could be a stock, a company increasing
00:13:50
in price over time as the underlying
00:13:52
company grows and becomes more
00:13:53
profitable. It could be the building you
00:13:55
own, the real estate you own growing in
00:13:57
value due to capital improvements or due
00:13:59
to increased demand in its local market.
00:14:01
In the bond world, it could just be a
00:14:03
bond value going up because global
00:14:05
interest rates decrease. And now all of
00:14:07
a sudden, your bond, which is paying a
00:14:09
higher interest rate, becomes more
00:14:11
valuable to investors. So for a typical
00:14:14
retirement portfolio, portfolio growth
00:14:16
equals dividends plus interest plus
00:14:19
capital appreciation. So dividends and
00:14:21
interest are are kind of one thing.
00:14:23
That's the cash flow back to you. And
00:14:24
then capital appreciation is the second
00:14:26
thing. It's the value of your assets
00:14:28
actually going up over time. So when
00:14:30
someone says, you know, a 60/40
00:14:31
portfolio grows at 9% per year on
00:14:34
average, what they're actually saying is
00:14:36
that 9% equals average dividends plus
00:14:39
average interest plus average capital
00:14:41
appreciation over time. So, getting back
00:14:43
to Barry's question, do dividends and
00:14:45
income count toward that 4% rule, the 4%
00:14:48
annual withdrawal rate or whatever rule
00:14:51
you want to use, 4%, 5%, 6%. The answer
00:14:54
is yes. If dividends and income are
00:14:56
leaving your portfolio, they are part of
00:14:58
your withdrawal rate. If you extract 2%
00:15:01
of your portfolio via income and
00:15:03
dividends and then another 1.3% via
00:15:05
selling assets, which is kind of what
00:15:07
Barry outlined in his math above, then
00:15:09
Barry's withdrawal rate is 3.3%. It's
00:15:12
the sum of the dividends and income,
00:15:14
which was 2% plus 1.3%, which was
00:15:17
selling assets for capital gains. Those
00:15:19
dividends and income, they are not free
00:15:21
money. Don't need to get into that topic
00:15:23
right now. Some of you might have heard
00:15:25
me talk about it before. You might have
00:15:26
heard other people talk about it before,
00:15:28
but dividends and income are not free
00:15:30
money. They are one of the key
00:15:31
components of your overall portfolio
00:15:33
return. And if you weren't extracting
00:15:35
those dollars via dividends and income,
00:15:37
you'd reinvest them or the companies
00:15:39
would reinvest them on your behalf and
00:15:41
and compound those dollars over time.
00:15:43
Believing that dividends are are free is
00:15:45
one of the biggest misconceptions in
00:15:47
especially DIY investing. I think very
00:15:50
few professional investors think that
00:15:52
dividends are free. They know better.
00:15:54
But I think there is an interesting
00:15:56
clutch of DIY investors on the internet
00:15:59
who uh are really convinced that
00:16:01
dividends are free. Very interesting. So
00:16:03
that really is the answer to Barry's
00:16:04
question. You know, I know Barry was
00:16:06
quoting the 4% rule. And as many of you
00:16:08
know, the the 4% rule, any withdrawal
00:16:11
rule, it's just a rule of thumb. It's a
00:16:12
starting point. It's a good way to do
00:16:14
some back of the napkin math, but it
00:16:15
does become pretty limited. You need to
00:16:17
go deeper. And so, Barry, I would
00:16:19
recommend you try to do maybe a
00:16:20
long-term cash flow model to analyze
00:16:22
your portfolio's planned withdrawal
00:16:24
sequence over time, including, of
00:16:26
course, income or dividends from your
00:16:28
taxable account. That withdrawal
00:16:29
sequence, it's likely to be lumpy,
00:16:31
right? It's not going to be constant.
00:16:33
It's not going to be 3.3% every year.
00:16:35
It'll change for sure once you start
00:16:37
collecting social security. It'll change
00:16:39
again when you hit RMD age. Some years
00:16:41
are probably going to include Roth
00:16:42
conversions or or the realization of 0%
00:16:46
capital gains or something like that.
00:16:47
You should do your best to try to plan
00:16:49
that out all ahead of time. And starting
00:16:50
your retirement without taking that
00:16:52
detailed step is probably a risky move.
00:16:54
So, if you haven't taken it yet, there's
00:16:56
no better time to start than right now.
00:16:57
Thank you very much for that question,
00:16:59
Barry. Here's a quick ad and then we'll
00:17:01
get back to the show. Every January we
00:17:03
make the same promises. Eat better, work
00:17:05
out, read more books, and of course,
00:17:07
something about money. You know, this
00:17:09
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00:17:10
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00:17:12
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currently accepting new clients. You can
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and fill out the short form. Let's make
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better finances the resolution that
00:17:33
actually sticks this year. And with
00:17:35
that, let's bring Jeremy Kyle onto the
00:17:37
show. Jeremy is a certified financial
00:17:38
planner and chartered financial analyst.
00:17:40
He works with clients from uh from his
00:17:43
home near Milwaukee, Wisconsin. He hosts
00:17:45
the Mr. Retirement YouTube channel and
00:17:47
he hosts a podcast called Retirement
00:17:49
Revealed. He also recently published a
00:17:52
book called Retire Today. Jeremy, you
00:17:54
could say, likes Retirement and I'm glad
00:17:56
he's here to share with us today.
00:18:02
>> [music]
00:18:04
>> Jeremy, you know, you you've built a
00:18:05
career around helping people step
00:18:08
confidently into their retirement. So,
00:18:10
when you zoom way out, maybe we can
00:18:12
start there. We zoomed way out. Here's
00:18:14
just a a a maybe this is a softball
00:18:16
question or maybe this is actually a
00:18:17
hard question. I could see it going both
00:18:19
ways. What do you think people
00:18:21
misunderstand the most about the
00:18:23
retirement decision itself? The biggest
00:18:26
misunderstanding with retirement is how
00:18:28
long you might actually be in
00:18:30
retirement. And there's two parts of
00:18:31
that equation. That's why I call it the
00:18:33
retirement longevity number. It's not
00:18:35
just life expectancy, but how long you
00:18:37
might be in retirement. And there's the
00:18:40
beginning, there's the end of your
00:18:41
retirement. At the beginning, if you ask
00:18:43
a 55year-old when might you retire or
00:18:46
when you planning to retire, they'll
00:18:47
tell you 65. But if you ask a 65year-old
00:18:51
when did you retire, they'll tell you
00:18:53
62. Most people retire three years
00:18:56
earlier on average. Which is why I
00:18:59
encourage you to be ready to retire
00:19:01
three years earlier.
00:19:03
>> Whatever your number is in your
00:19:04
spreadsheet of I'm going to retire at
00:19:05
this date, subtract three. That's your
00:19:08
target so that you'll be ready to retire
00:19:11
in case you're like the average American
00:19:12
who retires early. Or maybe you do the
00:19:15
math, you get there and you say, "Why am
00:19:16
I stick around for 3 years?" So that's
00:19:18
the beginning part of retirement. But
00:19:20
there's a lot of misunderstandings on
00:19:22
the end of retirement. your life
00:19:23
expectancy. How long might you expect to
00:19:27
retire? It's tough. I can't blame you
00:19:29
for getting it wrong, but chances are
00:19:31
you're getting your life expectancy
00:19:32
wrong. One part of it is when you read
00:19:35
the news articles about how long people
00:19:37
live, you're going to read 78.
00:19:39
>> Yeah.
00:19:40
>> 78 is the average life expectancy in
00:19:42
America for a newborn child. If you are
00:19:46
planning to retire, you're a lot closer
00:19:48
to 65 than you are to zero. And you need
00:19:52
to plan for your retirement based on
00:19:54
being 60 years old, 55 years old, 65
00:19:57
years old, whatever it is. And your life
00:20:00
expectancy is a lot closer to 85 than it
00:20:02
is to 78. But who cares what the
00:20:05
averages are? Go out, get your own
00:20:07
personal longevity estimate place called
00:20:10
longevity illustrator.org.
00:20:12
Free site. And I am such a huge fan
00:20:15
because you can get your own
00:20:16
personalized longevity estimate and then
00:20:20
you're almost there. You're almost there
00:20:21
because you need to understand what life
00:20:23
expectancy means. It's the median. It's
00:20:25
just the halfway point. Half the time
00:20:27
you'll die before that. Half the time
00:20:29
you'll die after that. You'll live
00:20:31
longer than that number. And so you want
00:20:34
to get an accurate number, but you also
00:20:36
want to consider what happens on both
00:20:37
sides of that line. What happens to you
00:20:40
and your spouse and your finances if you
00:20:43
die before you hit that number? What
00:20:45
happens to you, your spouse, your
00:20:47
finances if you happen to make it past
00:20:49
that number? So, get an accurate
00:20:51
estimate, but understand what happens on
00:20:54
both sides of that. I've got a couple
00:20:56
interesting follow-up questions. That
00:20:58
was two you you sparked two really
00:20:59
interesting thoughts for me. So, the
00:21:01
first one, let's go back to the the
00:21:02
pre-retire who you said, you know, the
00:21:05
average retiree ends up retiring three
00:21:08
years earlier than what they once
00:21:10
predicted they would retire at. So, the
00:21:13
question that naturally came to my mind,
00:21:15
it's kind of a two-parter, is when does
00:21:17
that change occur? So, you said, you
00:21:18
know, a 55-year-old will say 65, but
00:21:21
then by the time they're 65, the answer
00:21:22
actually ended up being 62. So, it's
00:21:24
kind of when does that change end up
00:21:26
occurring for people? I'm putting my
00:21:28
shoes my my myself in the listener's
00:21:29
shoes right now. But then also, what are
00:21:32
those biggest approximate causes that
00:21:34
lead that average retiree to pull back
00:21:37
their retirement date by 3 years? That's
00:21:39
a great question and I'm going to make
00:21:42
some assumptions. I'm going to assume
00:21:43
it's between 59 12 and 62. At 59 12, you
00:21:48
know that your IRA and 401ks are
00:21:50
available and that's very tempting where
00:21:52
you start thinking, do I really want to
00:21:54
put up with this anymore? you can get
00:21:55
the money out without a penalty. So,
00:21:57
that's a big trigger.
00:21:58
>> 62 is another big trigger because
00:22:00
>> do I want to put up with this anymore? I
00:22:02
can just quit and get paid to not work
00:22:04
by social security. So, I think those
00:22:06
two are big ages kind of in between.
00:22:08
That's a big turning point. So, there's
00:22:10
a bit of the the retirement I call it a
00:22:12
retirement age trigger.
00:22:14
>> Like you don't you're retiring, you're
00:22:16
doing something because it's just kind
00:22:17
of a a number that the government gave
00:22:19
you or your company gave you, but
00:22:20
there's still a trigger and a lot of
00:22:22
people come with that. Sometimes it's
00:22:24
your health. Often times it's your
00:22:26
parents' health. If you're 60 years old,
00:22:28
your parents are 85 to 90. They start
00:22:31
needing your help or your grandkids are
00:22:35
just born, they're 5 years old, you need
00:22:38
to somebody needs to get them to the the
00:22:40
bus stop, right? There's a lot of
00:22:42
triggers that are family related.
00:22:43
Everyone kind of thinks, "Oh, I might
00:22:45
have to retire early because of my own
00:22:47
health." It's usually somebody else's
00:22:49
health or you're taking care of the
00:22:51
grandkids or you got a new boss that's
00:22:53
younger than your son and you think I
00:22:55
can get social security and I don't have
00:22:57
to put up with this.
00:22:58
>> That's really interesting. Well, let's
00:23:00
pivot then to the on the tail side of
00:23:02
retirement. You said it was it was
00:23:03
longevityestimator.org.
00:23:06
>> longevity illustrator.org. It's put out
00:23:08
by the Society of Actuaries. There's no
00:23:11
one more qualified in the world to tell
00:23:13
you how long you might live than the
00:23:15
Society of Actuaries.
00:23:17
That's okay. We'll we'll make sure we
00:23:18
include that link in the show notes. And
00:23:20
just for the the listener who maybe
00:23:22
wants to check it out but but hasn't
00:23:24
checked it out yet, what kind of
00:23:26
questions do they ask you? And then in
00:23:29
your experience, I mean, I think you did
00:23:31
a good job of explaining. They still
00:23:33
present you with a median outcome,
00:23:35
right? They don't have a crystal ball,
00:23:37
but I'm I'm really interested to
00:23:38
understand kind of how accurate their
00:23:40
medium projected longevity ends up
00:23:43
being. This is the number one most
00:23:45
important number to your retirement
00:23:46
planning uh is your longevity, how long
00:23:48
you might live. So, take five minutes to
00:23:50
understand it ahead of time. You're
00:23:52
making million-dollar decisions here.
00:23:54
Learn about your longevity ahead of
00:23:56
time. What they do, they only ask four
00:23:58
questions. They ask your age. They ask
00:24:01
your gender. They ask if you are a
00:24:02
smoker or not a smoker. And they ask
00:24:05
your general health. Are you average
00:24:06
health, excellent health, or poor
00:24:09
health? And you might think that's four.
00:24:11
Come on. Yeah. And so I had Dale Hall,
00:24:13
the uh head researcher for the Society
00:24:16
of Actuaries on my podcast, Retire Today
00:24:18
podcast. And I asked him that. He said,
00:24:20
"Well, we need to combine being accurate
00:24:24
with also people going through and doing
00:24:27
it. And how much precision do you really
00:24:29
need?" Right? If I ask you four
00:24:31
questions and I get you 95% of the way
00:24:33
there or ask you a 100 questions and you
00:24:36
don't even bother doing it, which one's
00:24:38
a better deal? And a lot of times all
00:24:41
these other factors about, you know,
00:24:42
family health, your own health, you have
00:24:44
a good idea and just answer it. Am I
00:24:46
average health? Am I excellent health?
00:24:48
Am I poor health? That's going to get
00:24:49
you most way there. And those are the
00:24:51
most important factors. Your age, your
00:24:53
gender, are you a smoker or not? And
00:24:55
just your overall level of health. So
00:24:57
they get very specific just off of those
00:25:00
and they'll give you the median. More
00:25:02
importantly, they'll give you the whole
00:25:03
probabilities. A lot of people come to
00:25:05
my office and they're asking me about
00:25:06
social security and what's the break
00:25:08
even age and what are the odds I'll make
00:25:10
it to the break even age. I said let's
00:25:12
go here and let's find the odds that
00:25:14
you'll make it to the break even age. So
00:25:16
you can go through and say oh the odds
00:25:17
are 72%.
00:25:19
>> So is that a number you want to make? Do
00:25:21
you want to take those odds? Those are
00:25:22
pretty good odds. If you walk into
00:25:23
casino you will take those odds.
00:25:25
>> But also they do something called joint
00:25:27
life expectancy. If there's two of you,
00:25:30
it's harder for two people to die than
00:25:32
one person to die. Or kind of the
00:25:34
inverse of that, it's on average, if
00:25:36
there's two of you, one of you might
00:25:38
make it not there. You'll be die below
00:25:40
average. One of you will live longer
00:25:43
than average. And you can't just look at
00:25:45
your own individual life expectancy.
00:25:48
You've got to look at the life
00:25:49
expectancy of the couple. You got to
00:25:50
look at the life expectancy of the
00:25:52
person that's likely to make it above
00:25:55
average. So, it's that joint life
00:25:56
expectancy is a huge thing to look at
00:25:58
when you're a couple.
00:26:00
>> Yeah, totally totally agree with that.
00:26:01
That's really interesting. The the the
00:26:03
four questions are really powerful and I
00:26:05
think it it illustrates to me for
00:26:08
example, I know the one question was
00:26:09
about smoking. I I know if that's one of
00:26:11
their top four questions obviously that
00:26:14
smoking that binary option must play a
00:26:17
really large must have a really large
00:26:19
influence in the outcome of how long you
00:26:21
live. And the other thing you made me
00:26:23
think of, Jeremy, is that quite
00:26:24
understandably, I think people, we have
00:26:27
a hard time with what I would call
00:26:28
conditional probabilities. And you
00:26:30
brought it up earlier. I I liked your
00:26:32
example with um you know, you look it up
00:26:34
in the newspaper, you see an article,
00:26:35
the average person lives to 78, right?
00:26:37
That's the average newborn. But once
00:26:39
you're already listening to this podcast
00:26:41
today and you're 55, the question should
00:26:43
be, what's the average age that you uh
00:26:46
live to conditional upon the fact that
00:26:49
you're already 55 years old? Maybe I'm
00:26:51
phrasing that in a way that a
00:26:52
statistician wouldn't appreciate, but
00:26:54
the point is that all these
00:26:56
probabilities that retirees have to deal
00:26:58
with. You've already avoided some of the
00:27:01
negative outcomes. So, it's really, you
00:27:02
know, how long will you live conditional
00:27:04
upon the fact that you're not a smoker,
00:27:07
that you happen to be a woman, that
00:27:08
you're already 58 years old, and you're
00:27:10
in great health. That is a really
00:27:12
important and fundamentally different
00:27:13
question than just how long does the
00:27:15
average person live? So, I I I really
00:27:17
like the fact, and I think that's really
00:27:18
unique take that you have. It's kind of
00:27:21
simple in a way like once you hear it,
00:27:22
but right I think there's so many voices
00:27:24
in this space that simply are not asking
00:27:27
that fundamental basic question and it
00:27:30
takes you five minutes to get there. And
00:27:32
speaking of probabilities, here's
00:27:34
another thing that people get wrong with
00:27:36
life expectancy. They talk about their
00:27:38
own life expectancy as if it's their
00:27:40
death certainty. Like people don't say,
00:27:43
"I might live to 80 or I've got a 50%
00:27:46
odds of getting to age 82." They say,
00:27:48
"I'm going to die at 80. I won't make it
00:27:51
into my 70s." No, that's not correct.
00:27:53
I'm a math guy. I like looking at stuff.
00:27:55
I looked at another math longevity
00:27:58
table. It's from the Social Security
00:28:00
Administration. Nobody else in America
00:28:02
knows more about Americans dying and
00:28:05
living than Social Security because
00:28:07
they're paying out or not paying you
00:28:08
out, right? And if you look at their
00:28:10
chart and you're 55, 60, 65 years old,
00:28:14
whatever the number is, and you look at
00:28:16
your life expectancy, I'm 62 years old.
00:28:19
My life expectancy is 87. And the odds
00:28:22
that you actually die at 87, 4%.
00:28:25
>> 4%.
00:28:26
>> You have less than 4% chance of actually
00:28:28
dying at your life expectancy. You have
00:28:31
a near certainty of not dying at your
00:28:34
life expectancy. So get the number
00:28:36
correct and then think about what is the
00:28:39
near certainty that I won't actually
00:28:41
live to that number and make your
00:28:43
decisions based on that. That's so
00:28:45
funny. That's so interesting. Well, I
00:28:47
guess speaking of those conditional
00:28:48
decisions, Jeremy and and you already
00:28:50
did mention social security. I really
00:28:51
liked your take on the on the spousal
00:28:53
decision about or or maybe the fact that
00:28:55
you know one spouse is likely going at
00:28:57
least one spouse is going to live a long
00:28:59
time. that might play into the social
00:29:01
security decision at all. But I don't
00:29:03
want to lead the witness here. I mean,
00:29:05
what is your take on social security
00:29:08
claiming strategies for lack of a better
00:29:10
term? Yeah. So, two parts of social
00:29:12
security is one, you ought to learn the
00:29:14
math and actually do the math. And when
00:29:16
you look at social security, especially
00:29:18
if there's two of you, if there's two of
00:29:19
you,
00:29:20
>> your benefits grow by roughly 8% per
00:29:22
year by waiting. But if there's two of
00:29:25
you, one of your numbers is bigger. and
00:29:27
8% on a bigger number is a bigger
00:29:30
number. Your default thought is you
00:29:33
probably want to take that bigger number
00:29:35
and wait a little bit longer than you
00:29:37
expected and you probably want to take
00:29:38
that smaller benefit and maybe take it a
00:29:41
little bit earlier than you expected
00:29:42
because it matters a little bit less.
00:29:44
It's a smaller number and the rules of
00:29:47
social security, the survivorship is
00:29:50
going to show up to be the higher
00:29:52
number. the survivorship option. If
00:29:54
there's two social securities, one of
00:29:56
them is going to go away. It's a smaller
00:29:58
one. So, you got a smaller number that
00:30:00
doesn't grow as much, that doesn't last
00:30:02
as long. Feel okay taking that a little
00:30:05
bit earlier than perhaps you wanted or
00:30:07
plan to, but then the bigger one is a
00:30:10
bigger number and it's a bigger deal for
00:30:12
a longer time. Probably wait a little
00:30:14
bit longer on there. So, that's kind of
00:30:16
a just a quick thought on it. But if you
00:30:18
want one thing to say, how should I
00:30:20
approach and make my social security
00:30:22
decision, forget the probabilities I
00:30:24
talked about earlier, forget about the
00:30:27
break even calculator that you already
00:30:28
have in your spreadsheet right now. I
00:30:30
want you to think of social security in
00:30:32
terms of its official name. The official
00:30:35
name for social security is the old age
00:30:38
survivor insurance program. It's there
00:30:41
to help you in your old age. It's there
00:30:43
to help your survivor. It's there to be
00:30:46
insurance in case you live longer than
00:30:48
you expected or inflation came in higher
00:30:50
than expected or your market returns
00:30:52
weren't as much as expected. So when
00:30:55
you're looking at your social security
00:30:56
and thinking of it of how does this help
00:30:58
me in my old age? How does this help my
00:31:01
survivor? How does this help the
00:31:03
insurance aspect of my retirement and
00:31:05
things in case things don't go as well?
00:31:07
That's how you approach social security.
00:31:09
>> Got it. And that that makes sense. And
00:31:11
and going back to the the spousal
00:31:13
decision-making, just to make sure that
00:31:15
I'm following along and and the
00:31:16
listeners are following along. The way
00:31:17
I've heard it described before, let's
00:31:19
think of this imaginary couple with two
00:31:21
different benefits, one larger benefit,
00:31:23
one smaller benefit. I I think the way
00:31:25
I've heard it described is you know that
00:31:27
when the first spouse dies, no matter
00:31:30
what, the smaller benefit is going to
00:31:32
drop away and the larger benefit is
00:31:34
going to continue on with the surviving
00:31:36
spouse. And it really doesn't matter.
00:31:38
You know, it's either the larger spouse
00:31:40
dies first and the smaller spouse
00:31:43
inherits that survivor benefit or the
00:31:46
smaller spouse dies first and okay, the
00:31:48
larger spouse now continues that. So,
00:31:50
you just know either way, the larger
00:31:52
benefit is going to outlive the smaller
00:31:54
benefit and you'd rather just wait to
00:31:56
let the larger benefit grow and grow and
00:31:58
grow a little bit extra. I mean, is that
00:32:00
the underlying logic?
00:32:01
>> That's exactly it. You should you should
00:32:03
become a financial adviser.
00:32:04
>> Yes. Right. Right. I should start a
00:32:05
podcast. Well, I mean, thinking about
00:32:07
the way that these different, you know,
00:32:09
we've talked about social security, but
00:32:11
we know there are all these different
00:32:13
aspects of retirement planning and
00:32:16
holistic planning, I found, can feel
00:32:19
overwhelming to people. There are tax
00:32:21
consideration, there's income planning
00:32:23
in retirement, how should that affect my
00:32:25
portfolio? Do I need to think about
00:32:27
estate planning? And sometimes in the
00:32:29
early conversations with people, it's
00:32:32
almost like, I know I've got eight
00:32:34
different things I ought to be concerned
00:32:35
about. I don't know which one I should
00:32:36
start with. So, how do you tend to
00:32:38
sequence your conversations so that your
00:32:40
clients or just people that you're
00:32:42
talking to don't feel totally
00:32:44
overwhelmed and they have a a specific
00:32:46
order to approach these retirement
00:32:48
planning problems. Yeah, that's exactly
00:32:50
it. You want to take a comprehensive
00:32:52
look at your finances. You want somebody
00:32:54
that takes a comprehensive look at your
00:32:56
finances, but you want to do it in the
00:32:58
right order. It's kind of like you want
00:32:59
to make the first decision because it
00:33:01
informs the second decision and on down
00:33:03
the line. And you know what you're
00:33:04
referencing is the five steps I put in
00:33:06
my book. I've got my book retire today.
00:33:08
I call it create your retirement master
00:33:09
plan in five simple steps. One, because
00:33:12
there's five steps. It's what I've done
00:33:14
for 22 years as a financial adviser to
00:33:16
help you create your retirement master
00:33:18
plan. But the order I take them in, you
00:33:20
might be surprised. A lot of people
00:33:22
start with an order where way down the
00:33:24
line in my opinion. The first thing I
00:33:26
think you ought to do when you're
00:33:27
looking at your retirement is figure out
00:33:29
how much is it you're going to spend in
00:33:31
retirement which is a bit of how much
00:33:33
like what am I going to spend every
00:33:34
month or every year but it's also the
00:33:36
how long that we have already talked
00:33:38
about and a lot of people hit retirement
00:33:41
and they're almost afraid to do some
00:33:42
retirement planning because they feel
00:33:44
like I've got to do a budget and they
00:33:47
hate doing budgets so they just put that
00:33:49
off which means they put off the
00:33:50
retirement planning. I tell you don't do
00:33:52
a budget. The only thing you have to do
00:33:53
to figure out how much you might spend
00:33:55
in retirement is to look at is to look
00:33:58
at how much you are spending today. And
00:34:00
the easiest way to do that is look at
00:34:02
your paycheck. Whatever shows up in your
00:34:04
take-home pay into your checking
00:34:07
account, usually what goes into your
00:34:08
checking gets spent. You might make
00:34:11
150,000 for your salary, but if it's
00:34:14
only 3,000 every paycheck times 26
00:34:18
paychecks, it's $78,000 a year that
00:34:20
you're spending on what I call your
00:34:21
lifestyle spending amount because you're
00:34:24
it's coming in and you're spending that
00:34:26
money on whatever it is you do. And
00:34:28
that's great. Go do what you want to do.
00:34:30
What's interesting though about your
00:34:31
paycheck is it already took out your tax
00:34:33
cost. It already took out your health
00:34:35
insurance cost. So that's the next two
00:34:37
things you put into your budget. You
00:34:39
don't have to go out and build a budget
00:34:41
from the ground up. Just look at what's
00:34:42
my take-home pay, that's my lifestyle
00:34:44
spending amount. Then let me put into my
00:34:47
planning what's my likely health
00:34:48
insurance costs, what's my likely tax
00:34:51
cost. You've taken care of most of it
00:34:53
just right there. That's the first step
00:34:54
is to look at the the spending. Not let
00:34:57
me look at the investments. That's on
00:34:58
down the line. And I suppose I mean does
00:35:00
it matter after that point kind of
00:35:03
what's next? Now I don't you know we
00:35:05
don't have to go into every bit of
00:35:06
minutiae and detail. So, we start with
00:35:09
spending. I like the fact that your own
00:35:10
paycheck kind of back you into a a rough
00:35:13
outline of what your spending is, but
00:35:16
where do conversations go from there? Or
00:35:18
is it just a case- by case basis? And it
00:35:20
depends on what's going on in the
00:35:21
individual circumstances. The next step,
00:35:23
step two, is what is it you make? Just
00:35:26
because you stop working doesn't mean
00:35:28
you stop making money. You might be
00:35:30
making money in retirement from a
00:35:32
pension, from real estate, from some
00:35:34
annuity that you've already purchased
00:35:36
before. And definitely you'll have
00:35:38
income from social security. A lot of
00:35:41
these, especially with the social
00:35:42
security and the pension, you got these
00:35:44
one-time decisions that affect the rest
00:35:46
of your life.
00:35:47
>> So, it takes some time here to figure
00:35:49
out what is it that I need to do with my
00:35:52
decisions to help set me up for the
00:35:54
whole lifetime. That's the second step.
00:35:56
The third step is I know how much I
00:35:58
need. I know what's coming in from the
00:36:00
consistent lifetime income. How do I
00:36:03
keep more of my money? Step three is
00:36:05
keep. How do I project out and plan for
00:36:09
the times that I have a lower tax
00:36:11
situation and the times I have a higher
00:36:13
tax situation? And the way to do tax
00:36:15
planning in retirement is to kind of
00:36:16
even those out. If you see here's a year
00:36:19
down the road where I'm going to have a
00:36:20
high tax situation, I want to avoid
00:36:23
income showing up that year. But if I
00:36:25
have years down the road, often just
00:36:27
after retirement and before you turn on
00:36:29
social security, if I have a projected
00:36:31
lower income, lower tax rate situation,
00:36:34
you want income to show up at the lower
00:36:36
tax rate, usually through Roth
00:36:38
conversions. So the step three is the
00:36:39
tax planning, how to keep more of that.
00:36:42
Step four is finally to invest your
00:36:45
money. Most people think it's step one.
00:36:47
Most people think a financial advisor
00:36:48
job is step one to go invest your money.
00:36:51
You don't know what you're investing for
00:36:52
until you figure out the first three
00:36:54
parts of it. And the biggest thing you
00:36:55
want to think of with investing is when
00:36:58
do I need the money? It's not about
00:36:59
picking the perfect stock and bond. It's
00:37:01
about having the money available when
00:37:03
you need it. And if you need the money
00:37:04
in the short term, you need short-term
00:37:06
money. If you need it available in the
00:37:08
long term, you need long-term
00:37:10
investments. The thing that's
00:37:12
interesting with retirement, why I think
00:37:13
it's so scary, you spent your whole
00:37:15
career saying, "Invest for the long run.
00:37:18
It's down the road." And then you got
00:37:20
down the road and now you got the
00:37:21
shortterm. You got the short run and you
00:37:24
need some short run money, but a lot of
00:37:25
times you think that's all you need. No,
00:37:27
you still have a long ways away. You
00:37:29
need long-term money. You need
00:37:30
short-term money. You need the right mix
00:37:32
there. That's what you focus on in step
00:37:34
four. And then you get to the fifth
00:37:35
step, which is what is it you leave
00:37:37
behind? Some people leave behind their
00:37:39
money. Some people leave behind their
00:37:41
mess. And I'm guessing you'd rather
00:37:43
leave behind money to the next
00:37:45
generation versus leave behind a mess.
00:37:47
So step five is looking at it's a bit of
00:37:50
what's the amount you might leave
00:37:52
behind, but it's also what are the
00:37:54
things you've done to prepare the next
00:37:57
generation either the documents or the
00:37:58
the ways that you've set them up so that
00:38:01
you've kind of taken the risk off the
00:38:02
table and make sure that things are
00:38:04
going to turn out right even when they
00:38:06
don't happen to be all right.
00:38:08
Interesting. I like the five-step
00:38:09
process. I mean, it's it's very clean
00:38:11
and it's easy to remember. And I think
00:38:12
as humans, we're kind of naturally
00:38:14
aligned to we we like when things go in
00:38:17
order. And hey, five is an easy round
00:38:19
number to keep track of.
00:38:21
>> Here's a quick ad, and then we'll get
00:38:22
back to the show. Did you know my
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written blog, The Best Interest, was
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00:38:29
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00:38:37
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00:38:42
read them all at bestinterest.blog.
00:38:45
Again, the web address is
00:38:47
bestinterest.blog.
00:38:49
Check it out. I think I heard you,
00:38:51
Jeremy. I I want to say it was on
00:38:53
another podcast, although I'm not at
00:38:55
this point. I can't quite remember, but
00:38:56
I think I heard you say that tax
00:38:59
planning, so it was step three, it was
00:39:00
that keep step is the place where most
00:39:04
maybe you said where most retirees leave
00:39:06
the most money on the table or something
00:39:08
along those lines. So, I kind of wanted
00:39:10
to zoom in on that one. I mean, whether
00:39:12
it's a a single mistake that you just
00:39:15
see happening over and over again or
00:39:17
whether it's just a a lack of knowledge
00:39:19
and a series of just, you know, missed
00:39:21
opportunities that you see. I mean,
00:39:23
what's going on there that makes tax
00:39:24
planning so important, but yet also so
00:39:27
often overlooked? Yeah, your tax
00:39:30
planning is often overlooked because you
00:39:31
spent 35 years working not really having
00:39:35
much chance to actually affect your
00:39:37
taxes, right? If you're a W2 employee,
00:39:39
you don't own a business and you're
00:39:40
worried about that stuff. But if you're
00:39:41
a W2 employee, you get your W2, you give
00:39:44
it to your tax person, it's kind of too
00:39:46
late, and you didn't really have too
00:39:48
much you can actually do about it. But
00:39:50
you hit retirement, you have so much
00:39:52
more opportunity to actually affect your
00:39:55
taxes. And that's where the power comes
00:39:57
in of your tax planning where you get
00:40:00
the choice of when do you take your
00:40:02
money out and what type of money do you
00:40:05
take out, right? You could take money
00:40:06
out in December or January. It's two
00:40:08
different tax years. That's two
00:40:09
different tax situations. Or you've got
00:40:12
your brokerage account, your savings
00:40:14
account, your traditional account, your
00:40:15
Roth account. [clears throat]
00:40:16
That's four different types of money
00:40:19
with four different types of tax
00:40:21
situations. So when you plan out and
00:40:24
look ahead and say when do I want my
00:40:27
money to show up to me? When do I want
00:40:29
my money to show up on the tax return?
00:40:32
Which account am I going to take money
00:40:33
from? You can make positive changes to
00:40:37
your tax situation as in it'll be lower
00:40:39
in the long run. That's your projection.
00:40:42
And I often see a 20% projected lower
00:40:46
tax burden over your whole lifetime. And
00:40:49
if you want to depress yourself one day,
00:40:51
project out your entire level of taxes
00:40:54
you'll pay over your lifetime. You might
00:40:57
be sorely surprised. It's probably a
00:40:58
million dollars.
00:40:59
>> It's a lot of money that you are likely
00:41:01
to pay in taxes over your lifetime. And
00:41:04
if all it takes is a little bit of
00:41:05
planning and kind of forethought to say,
00:41:07
"Oh, I'm going to pay taxes when it's
00:41:09
lower. I'm gonna avoid taxes when it's
00:41:11
higher and you might get a 20% tax
00:41:14
savings. It It seems well well worth it
00:41:16
to me.
00:41:16
>> Definitely. One of my go-to phrases
00:41:18
there is that we all have an obligation
00:41:21
to to pay taxes or, you know, by law we
00:41:23
all have to pay taxes, but we also all
00:41:25
have, you know, a right to not pay any
00:41:27
more taxes than we otherwise have to.
00:41:29
And that's one of those foundational
00:41:31
ideas behind tax planning that really
00:41:32
resonates with me. I mean, speaking of
00:41:35
tax planning, Roth conversions, just to
00:41:37
talk a little more about those, I think
00:41:39
sometimes Roth conversions are talked
00:41:41
about like they're magic. Oh, and
00:41:44
really, I mean, it's pretty nuts and
00:41:45
bolts. How would you help someone
00:41:47
listening right now simply just figure
00:41:49
out if they're a good candidate for a
00:41:51
Roth conversion, whether it's today or
00:41:54
at some point in their future
00:41:55
retirement? I mean, how does someone
00:41:56
know if they're a good fit or if
00:41:58
actually it's just kind of not going to
00:41:59
work out for them? Well, everyone should
00:42:01
consider a Roth conversion. And what you
00:42:04
do is you project out what your tax
00:42:06
situation is going to be like. For me, I
00:42:09
have software that projects out every
00:42:11
tax return from here until the end of
00:42:12
time. I imagine you have software like
00:42:15
that as well, too. Chances are, if
00:42:16
you're a do-it-yourself individual, you
00:42:18
don't have access to that tax software.
00:42:20
But consider the kind of before and
00:42:22
after situations when your taxes are
00:42:24
likely to change before you're retired
00:42:27
and after you're retired, before you
00:42:29
turn on social security, after you turn
00:42:30
on social security, before your RMDs,
00:42:34
after your RMDs start. And one that's
00:42:36
often overlooked is if there's two of
00:42:38
you while you're a married filing joint
00:42:40
versus a survivor, a single tax return.
00:42:44
So that's eight before and after, as I
00:42:46
just said right there. take a little
00:42:48
time, maybe project out eight tax
00:42:50
returns and say, "Wait a second. There's
00:42:52
some times here where I'm in the 12% tax
00:42:54
bracket. There's some times there I'm in
00:42:56
the 24% tax bracket. What can I do to
00:43:00
try to pay taxes in the 12% lower tax
00:43:02
bracket to avoid the taxes in the higher
00:43:04
tax bracket? And often the way to do it,
00:43:06
the probably the best way to do that is
00:43:08
to do a Roth conversion. is to
00:43:10
intentionally pay taxes on purpose on
00:43:12
your traditional IRA by converting it
00:43:15
over to the Roth IRA so that that growth
00:43:17
now is tax-free and there's no RMD then
00:43:20
on the Roth IRA where you're not being
00:43:22
forced out to do that. So that's how you
00:43:25
look at it ahead. But the biggest
00:43:27
mistake people make when it comes to tax
00:43:29
planning is just thinking they don't
00:43:31
have the control. You do have the
00:43:33
control. take some time, put some uh pen
00:43:36
to paper, get out the spreadsheet, and
00:43:38
project out these different times, find
00:43:40
your low tax situations, try to pay
00:43:42
taxes then. Yeah, it totally lines with
00:43:46
my understanding. And uh cuz I think the
00:43:48
the funny situation that I thankfully
00:43:50
haven't run into much, Jeremy, but it's
00:43:52
come in a couple times from from
00:43:53
listener emails or reader emails is
00:43:56
people who say, "You know what? I I
00:43:59
haven't really figured out, they might
00:44:00
not even know this, that they haven't
00:44:01
figured out their long-term kind of tax
00:44:04
bracket projections yet." Here they go.
00:44:08
And they say to themselves, "I've heard
00:44:09
Roth conversions are good. I happen to
00:44:11
be 15 years old or 52 years old. I'm a
00:44:13
VP at some big company. I'm making
00:44:15
$400,000 a year." and I'm doing a whole
00:44:17
bunch of Roth conversions and I sit
00:44:19
there and [laughter] oh no, you're in
00:44:21
like the 32 or 35% tax bracket and odds
00:44:24
are if you're making Roth conversions in
00:44:26
that tax bracket, it's probably not
00:44:28
ideal for you. And just like you ended
00:44:31
on, I mean, the whole point is to
00:44:32
identify your lowest future tax years
00:44:34
between now and the end of time and to
00:44:37
consider stuffing those years with with
00:44:39
Roth conversions. People get convinced
00:44:41
that Roth conversions are magic and they
00:44:43
want the magic. So, they don't really
00:44:44
think about their tax situation, but uh
00:44:46
I don't know if that resonates at all
00:44:48
with you.
00:44:48
>> Yeah, you've got to think about your tax
00:44:50
situation because you want to project
00:44:51
out pay the taxes at the lowest time.
00:44:53
Figure out when it's best to pay the
00:44:54
taxes, that 52-year-old example there.
00:44:57
If they happen to do a withholding from
00:44:59
their traditional account, that's a 10%
00:45:02
tax penalty on the withholding because
00:45:04
they're below 59 and a half. So, you got
00:45:05
to figure out where you're going to pay
00:45:06
the taxes from. But a lot of people
00:45:08
think of the the binary of do I do tax
00:45:12
uh Roth conversions or not? And really
00:45:14
the answer is should I consider it? Yes.
00:45:17
Then the answer becomes well how much
00:45:19
and for how long and when? And so I had
00:45:22
a couple came into my office a few years
00:45:24
back and they kept getting hammered with
00:45:26
the Irma and the Medicare extra taxes.
00:45:29
And so I projected things out and said,
00:45:30
"Well, with your required minimum
00:45:32
distribution levels, you're just hitting
00:45:34
this one level just over and over again.
00:45:36
But if you happen to use up the entire
00:45:38
24% tax bracket, you will jump to the
00:45:42
next Medicare cost. It's going to cost
00:45:44
you extra Medicare for a couple years.
00:45:46
You're going to pay the taxes now at
00:45:49
24%. But hey, you're projected to always
00:45:52
be in the 24%, which at the time was
00:45:54
projected to go up even higher.
00:45:56
>> And so we did the math and said if you
00:45:57
just happen to take this, it was a
00:45:59
$600,000 account. if you convert it over
00:46:02
the next three years, 200,000 per year,
00:46:05
you'll save in the long run. It made a
00:46:07
lot of sense. This was late in the year,
00:46:09
December. I helped them do the Roth
00:46:11
conversion. I said, "We'll do the next
00:46:13
one in January, right?" Only four weeks
00:46:15
later. So, I called her and said, "It's
00:46:17
time to do the second of the three." And
00:46:19
she said, "Don't worry about it. No
00:46:20
need. It's already been done."
00:46:22
>> So, what do you mean? Our plan was to do
00:46:24
three years in a row. She said, "Yeah,
00:46:26
but you said it was a good idea, so I
00:46:28
just did the whole thing. I figured just
00:46:29
rip the band-aid off. It's not going to
00:46:31
matter anyways. No.
00:46:33
>> And by then it was too late. And I said,
00:46:34
"Well,
00:46:35
>> all right. Well, thanks for letting me
00:46:36
know." And I thought, I wonder how much
00:46:37
it did matter to her cuz she did not
00:46:40
stay in the 24% tax bracket for 3 years.
00:46:43
She jumped into the 32% tax bracket and
00:46:46
then the 35% tax bracket for that
00:46:48
particular year. I did the math. It was
00:46:50
$23,000 of extra taxes because she said,
00:46:53
"It doesn't matter. Let me just take
00:46:55
care of all of it." She follow what you
00:46:57
said. A lot of people think the Roth
00:46:58
conversion is a magic magic pill. You
00:47:00
got to plan some things out ahead of
00:47:02
time.
00:47:02
>> Yeah, that's a very painful way to rip
00:47:04
off the ba the band-aid. 20 $23,000
00:47:07
worth of tax pain.
00:47:08
>> Extra taxes. Yes. Exactly.
00:47:10
>> Right. Right. Extra taxes. Well, let's
00:47:12
pivot. I' I've got an interesting kind
00:47:14
of emotional question for you again. I
00:47:16
think that from my vantage point, there
00:47:19
are some big emotional hurdles that
00:47:21
people face, especially in either the
00:47:24
last few years leading into retirement
00:47:26
or sometimes the first few years at the
00:47:29
start of retirement. So, I'm just
00:47:30
wondering in your experience, what are
00:47:32
some of those really notable emotional
00:47:35
hurdles that that stick out to you that
00:47:36
that people face in that retirement
00:47:39
transition phase?
00:47:40
>> Yeah, I'd say there's two emotional
00:47:42
hurdles I see in there. One is people
00:47:45
think, "Have I have I done enough? Like
00:47:47
am I really going to be okay?" You know,
00:47:49
I've never done this before. A lot of
00:47:51
people say to me, I don't know what I
00:47:53
don't know. Like I'd hate to retire and
00:47:56
then realize I made a mistake and it's
00:47:58
too late to fix it. So that's why like
00:47:59
let me guide you through the process
00:48:01
that I've guided hundreds of people
00:48:02
before. So you feel a lot more confident
00:48:04
in your money when you know more about
00:48:06
your money. And that extra confidence
00:48:08
actually helps you make better money
00:48:10
decisions itself. So you want to have a
00:48:12
process. That's a a mistake, an
00:48:14
emotional, right? If you there's a lot
00:48:17
to worry about if you don't know what to
00:48:18
do, but if you know what to do
00:48:21
addressing each worry along the way. The
00:48:23
other thing people are concerned about
00:48:26
is I've been spending I've spent 35
00:48:29
years saving into my account statements.
00:48:33
I've spent 35 years adding to them. How
00:48:36
am I supposed to start taking the money
00:48:38
out? I'm a saver and that's a good
00:48:40
thing. and you want me to become a
00:48:41
spender and that's absolutely evil. So
00:48:44
there's this huge identity people put
00:48:46
into their minds about I am a saver and
00:48:49
I cannot become a spender. And my
00:48:51
encouragement there is you're not a
00:48:53
saver. You're not currently a saver. You
00:48:56
started out planning. You're a planner.
00:48:59
You've been planning towards retirement.
00:49:01
The tool, the tactic you were using was
00:49:04
saving, but you're still a planner. And
00:49:07
now it's time to use the next tool which
00:49:09
is spending. And so if you can think of
00:49:11
yourself of I'm a planner, not a spender
00:49:14
or a saver, you can continue on saying
00:49:17
I'm just always been planning. I'm still
00:49:19
planning. It's just I'm using a
00:49:21
different tool. But that's I hear that a
00:49:22
lot of I'm a saver. I can't become a
00:49:26
spender. And try to disassociate your
00:49:29
identity with those two words and add
00:49:31
back in the word that you've always
00:49:33
been. you're a planner and just because
00:49:34
you're taking money out of your
00:49:35
accounts, it still means you're a
00:49:37
planner.
00:49:37
>> I really like that. I, you know, it's
00:49:39
just a slight pivot, a slight pivot to
00:49:42
being a planner. I think that does, it
00:49:45
resonates with me. You can probably tell
00:49:47
by the way I'm stuttering over my words.
00:49:48
I would wager that resonates with a lot
00:49:51
of people out there, too, because it is
00:49:53
it's kind of like two sides of the same
00:49:55
coin, right? The saving and the spending
00:49:57
are two sides of that planning coin. I'm
00:50:00
curious, do you find any any sort of
00:50:02
issues? I shouldn't say issues, but in
00:50:04
your conversations with clients once
00:50:07
people are a year or two or five years
00:50:09
into retirement, do they ever come back
00:50:11
to you and say, "Boy, retirement isn't
00:50:13
really what I thought it would be." And
00:50:15
if they do come back to you and say
00:50:16
that, I mean, what are the usual reasons
00:50:18
why? That is interesting. If uh in the
00:50:20
financial advisor space in the
00:50:22
retirement researching space, that's a
00:50:24
big hot topic of you want to retire to
00:50:26
something instead of from something and
00:50:28
you want to have a a phase retirement
00:50:30
and you you want to change your identity
00:50:32
from being this worker person to being
00:50:34
whoever it is you want to be out there.
00:50:36
And I agree with that for a lot of
00:50:40
people. I just don't see it.
00:50:42
>> I just I really don't see it. The people
00:50:43
that come to me, they're not doctors and
00:50:46
lawyers and business owners. There are
00:50:48
people that have worked for the same
00:50:49
company, a public company with a pension
00:50:52
for 35 years. They've been looking
00:50:55
forward to collecting that pension.
00:50:56
They've been looking forward to spending
00:50:57
the time with their grandkids. They've
00:50:59
got this list of things they want to do.
00:51:01
And they retire. They love it. And they
00:51:04
tell me, "I wish I done it earlier." And
00:51:06
they also say, "How did I have any time
00:51:07
to do anything when I was working? I'm
00:51:09
not working and I'm still busy as ever."
00:51:12
So, it's this interesting thing. It's
00:51:14
like a a certain persona that happens to
00:51:18
be the persona that a lot of uh
00:51:19
adviserss and retirement researchers and
00:51:22
academics are in. I don't see that
00:51:24
outside of that. That's really
00:51:25
interesting. I I like that perspective
00:51:27
too. And uh I can admit I think both my
00:51:30
parents are very much in your court or
00:51:32
in the court of maybe your clients,
00:51:34
Jeremy, where um they both were public
00:51:36
school teachers. And I know especially
00:51:38
having some conversations with my dad,
00:51:39
he couldn't wait to retire. It's not
00:51:41
like he didn't like work, but he knew
00:51:43
exactly what he wanted to do with his
00:51:44
free time, and he never looked back. And
00:51:46
I he's just, you know, happy as a pig
00:51:48
and slop with with what he's spending
00:51:49
his time on in retirement. So, it really
00:51:51
is maybe, you know, to each their own,
00:51:53
and um there's a spectrum of outcomes
00:51:55
there. You know, Jeremy, you've shared
00:51:57
so much with us today from kind of your
00:51:59
real retirement focus, retirement
00:52:00
expertise, and I know you've mentioned
00:52:03
podcasting, I think YouTube, and your
00:52:05
book. Let's talk real quick. If someone
00:52:07
wants to follow up, if they want to
00:52:08
start consuming your content on a
00:52:09
regular basis, maybe they want to order
00:52:11
a copy of the book, where can they go to
00:52:13
check out the rest of your work? Yeah,
00:52:15
you're listening on the podcast now. Go
00:52:16
out and check out my podcast, Retire
00:52:18
Today, which is also the same name as my
00:52:21
book. The book is Retire Today, Create
00:52:22
Your Retirement Master Plan in Five
00:52:24
Simple Steps. You can find that
00:52:26
anywhere, but you can also go directly
00:52:28
to jeremyle.com, je.com.
00:52:34
If you're a video person, check me out
00:52:36
on YouTube. I'm Mr. Retirement on
00:52:39
YouTube. So, Mr. Retirement is what you
00:52:41
would type in to find me there. That is
00:52:44
an awesome screen name, Mr. Retirement.
00:52:46
Well, Jeremy Kyle, Mr. Retirement, thank
00:52:48
you so much for joining us on Personal
00:52:50
Finance for Long-Term Investors. Thanks
00:52:52
for having me on.
00:52:53
>> Thanks for tuning in to this episode of
00:52:55
Personal Finance for Long-Term
00:52:56
Investors. If you have a question for
00:52:58
Jesse to answer on a future episode,
00:53:00
send him an email over at his blog, The
00:53:03
Bestin Interest. His email address is
00:53:07
[music]
00:53:07
Again, that's jessevestinterest.blog.
00:53:11
Did you enjoy the show? Subscribe, rate,
00:53:13
and review the podcast wherever you
00:53:15
listen. This helps others find the show
00:53:17
and invest in knowledge themselves. And
00:53:20
we really appreciate it. We'll catch you
00:53:22
on the next episode of Personal Finance
00:53:24
for Long-Term Investors. Personal
00:53:27
Finance for Long-Term Investors is a
00:53:28
personal podcast meant for education and
00:53:31
entertainment. It should not be taken as
00:53:33
financial advice and it's not
00:53:34
prescriptive of your financial
00:53:36
situation.

Episode Highlights

  • Investment in Knowledge
    Benjamin Franklin's timeless advice reminds us that knowledge is the best investment.
    “An investment in knowledge pays the best interest.”
    @ 00m 04s
    January 14, 2026
  • CJ's Review
    CJ from NorCal praises the podcast for its accessible financial education.
    “Must read for financial education.”
    @ 01m 11s
    January 14, 2026
  • The Trap of Annuities
    Beware of fixed index annuities; they can be misleading and complex.
    “It's a trap!”
    @ 09m 33s
    January 14, 2026
  • Understanding Dividends
    Dividends are a key component of your overall portfolio return, not free money.
    “Dividends are not free money.”
    @ 15m 45s
    January 14, 2026
  • Start Planning Now
    There's no better time to start your retirement planning than right now!
    “There's no better time to start than right now.”
    @ 16m 56s
    January 14, 2026
  • Understanding Retirement Longevity
    Most people misunderstand how long they might actually be in retirement.
    “The biggest misunderstanding with retirement is how long you might actually be in retirement.”
    @ 18m 26s
    January 14, 2026
  • Life Expectancy Misconceptions
    Many people misinterpret life expectancy as a death certainty, which is incorrect.
    “You have less than 4% chance of actually dying at your life expectancy.”
    @ 28m 25s
    January 14, 2026
  • The Five-Step Process for Retirement Planning
    A clear five-step process helps navigate retirement planning effectively. 'It's clean and easy to remember.'
    @ 38m 09s
    January 14, 2026
  • Tax Planning: The Overlooked Opportunity
    Tax planning can save retirees significant money, often overlooked during their working years. 'You might be sorely surprised.'
    @ 39m 30s
    January 14, 2026
  • Emotional Hurdles in Retirement
    Many face emotional challenges when transitioning to retirement, questioning if they've done enough. 'Have I really done enough?'
    @ 47m 45s
    January 14, 2026
  • Retirement Realities
    Many retirees express joy and surprise at their newfound time and activities.
    “I wish I done it earlier.”
    @ 51m 01s
    January 14, 2026
  • Mr. Retirement
    Jeremy Kyle shares insights on retirement and promotes his podcast and book.
    “Check out my podcast, Retire Today.”
    @ 52m 15s
    January 14, 2026

Episode Quotes

Key Moments

  • Misconceptions15:45
  • Common Resolutions17:12
  • Retirement Longevity18:26
  • Budgeting Myths33:52
  • Spending Awareness34:21
  • Emotional Transition47:40
  • Changing Identity50:26
  • Mr. Retirement52:41

Words per Minute Over Time

Vibes Breakdown

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