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Making Retirement As Simple as Possible, but No Simpler (AMA, E138)

May 06, 2026 / 47:36

This episode of Personal Finance for Long-Term Investors covers retirement finance, portfolio rebalancing strategies, withdrawal rates, and social security claiming strategies. Host Jesse Kramer answers listener questions about simplifying financial planning and avoiding overcomplication.

In the first segment, Jesse addresses a question from Wes regarding investment losses and capital gains. He discusses the implications of generating losses to offset gains, emphasizing the importance of understanding the long-term effects of such strategies.

Next, Jesse responds to Cliff's inquiry about withdrawal rates in retirement. He critiques the suggestion of a 5% withdrawal rate based on an 8% return, explaining the risks associated with early withdrawals and the importance of considering market conditions.

Lucy asks about the timing of social security claims, and Jesse provides a nuanced view on the potential impacts of claiming early versus delaying benefits. He highlights the importance of considering individual health and family history in these decisions.

Finally, Nicole inquires about portfolio rebalancing strategies. Jesse explains the difference between time-based and drift-based rebalancing, ultimately recommending an annual rebalancing strategy to maintain the desired risk level in a portfolio.

TL;DR

Jesse Kramer answers listener questions on retirement finance, withdrawal rates, social security claiming, and portfolio rebalancing strategies.

Episode

47:36
00:00:00
Are you over complicating your finances
00:00:01
in retirement? Or are you maybe making
00:00:04
things too simple? That's the theme on
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today's Ask Me Anything episode,
00:00:08
including some interesting new ideas I
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learned during my research about optimal
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portfolio rebalancing strategies. Stay
00:00:14
tuned. Welcome to Personal Finance for
00:00:16
long-term investors, where we believe
00:00:19
Benjamin Franklin's advice that an
00:00:20
investment in knowledge pays the best
00:00:22
interest both in finances and in your
00:00:25
life. Every episode teaches you personal
00:00:27
finance and long-term investing in
00:00:29
simple terms. Now, here's your host,
00:00:32
Jesse Kramer. Welcome to Personal
00:00:34
Finance for Long-Term Investors, episode
00:00:36
138. I'm Jesse Kramer. I'm a financial
00:00:38
planner working with retirees and busy
00:00:40
professionals thinking about retirement
00:00:42
across the USA. You can learn more at
00:00:44
planwithjesse.com.
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Yes, that's a new web page for those
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avid listeners. Planwithjesse.com.
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Today is our 16th AMA ask me anything
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episode. Before we dive in though, this
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week's super soft t-shirt winner is
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Growing the Valley podcast, who left a
00:00:59
five-star rating and review on Apple
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Podcast. So, hey, Growing the Valley,
00:01:03
thank you for the kind words. Please
00:01:04
drop me an email to
00:01:07
so I can get that supersoft t-shirt sent
00:01:09
out to you. Now, on with the ask me
00:01:11
anything episode. As a reminder, these
00:01:13
are real questions from listeners just
00:01:15
like you. So, please don't hesitate to
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email me a question to the email address
00:01:19
jessebestinterest.blog.
00:01:21
Again, Jesse bestinterest.blog. I read
00:01:24
every single email that you guys send.
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Now, a few questions I've gotten over
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recent months reminded me of the the
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Einstein quote. Everything should be as
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simple as possible, but no simpler.
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That's the theme of today's episode. I
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truly think financial planning and
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investing and retirement planning is
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usually often over complicated
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especially in the DIYer world and the
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online forums where I I'll see arguments
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erupt about 3/100ths of a percent as a
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fee or whether small cap value is a
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mandatory requirement in your portfolio
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or not. I've seen groups of people kind
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of plant themselves on topics like
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social security where they say, "Hey, if
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you don't claim as early as possible,
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you're a moron." And they are opposed by
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people who plant themselves on the other
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side who say, "If you don't delay social
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security until you're 70, well then
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you're a moron." So anyway, my point is
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that a lot of people have strong
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opinions, strongly held, and sometimes
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there is complexity involved. But I do
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think something I see more often than
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not is over complexity. So yes, you
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know, retirement has its complexities,
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but we can simplify it. at least we can
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simplify it to a certain point because
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you know maybe there is 10 or 20% of the
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ideas that I hear where I feel like
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those ideas might be too simple or too
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easy. So anyway, the last thing I'll say
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in this preamble is I realize that yeah,
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there's some subjectivity to this idea
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that I'm talking about today. And and
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what I'm kind of saying is there's a
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line in between too complex and too
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simple. And I am subjectively drawing
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that line here today. Fair enough. I
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won't deny that fact. So, if you think
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I've drawn the line in the wrong place,
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feel free to call me out by sending an
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email to jessebinest.blog. I'd love to
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read your email. And we're going to dive
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into question one right now from Wes.
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Wes says, "Jesse, I appreciate the
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podcast and the blog content that goes
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beyond personal finance 101. Speaking of
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complex things, I have a question about
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generating investment losses to offset
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appreciated assets or the income from a
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Roth conversion. My adviser has been
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talking about a long short strategy that
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I'm researching. However, I was thinking
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I could either short a stock I think
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will go up, risky, or simply buy a
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leveraged ETF, less risky, that is the
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inverse of the S&P 500. It seems like a
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simple strategy, but I don't see much
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content out there about this. So, I'm
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guessing I'm missing some pitfalls. Can
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you give me some input? I Yeah, thanks
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for the question. Very interesting
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question. Now, normally I would kind of
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dive into all the details behind your
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question first. I'm going to do it
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slightly out of order listeners in this
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question, but don't worry, you will get
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an understanding of exactly what Wes is
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asking here, but I'm I'm going to paint
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a little picture first. Now, let's say
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you've invested money in the past and
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you've got $10,000 in capital gains,
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which you haven't realized yet. But when
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you do realize it, we'll be subject to a
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we'll say a 15% capital gains tax. So,
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you'd owe $1,500 in tax. But then, let's
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say you pursue a strategy, maybe similar
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to a strategy that Wes is outlining
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here, that creates $10,000 in capital
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losses. those losses offset the entire
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gain, eliminates the tax, and you're
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thinking to yourself like, "Nice, you
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just eliminated $1,500 in tax." However,
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we kind of glossed over the fact that
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you just generated $10,000 in losses.
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So, the $10,000 in losses totally wipe
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out the $10,000 in gains, and you no
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longer actually profited from your
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investment. The losses offset, wipe out
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the gains. So, the question is, would
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you rather have $10,000 in gains and and
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pay $1,500 in taxes or have no gains
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whatsoever? I would take the first
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scenario every day. You know, why lose
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$10,000 to save $1,500? Now, what I've
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just painted there is a very, very
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simple scenario. And most of the
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strategies that professionals are going
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to use are certainly more nuanced and
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yes, more complex than what I've just
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outlined. Now, what they hope to do is
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create some losses and some gains. The
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losses are going to be realized, but the
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gains will be unrealized. In other
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words, the assets that are sitting at a
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loss, the professionals will sell those
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assets so that you, the investor,
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actually have losses that appear on your
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tax return. But the gains, they say,
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we're not going to sell those assets.
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We're going to hold on to them because
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the whole point here is that we want to
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we want to wipe taxes away. We don't
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want to create more taxes for you. So,
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we are not going to realize the gains,
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at least not yet. So your realized
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losses can be used to lower this year's
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tax bill, of course, which is nice.
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Those new unrealized gains, we kick them
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down the road to a future tax year. We
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don't have to pay taxes on the
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unrealized gains, at least not yet. So
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the question becomes, will we ever have
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to pay taxes on the unrealized gains?
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And and that's why I think in some way
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whenever we're talking about these kind
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of capital gains, capital loss
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strategies, if the problem involves
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kicking the gains down the road to a
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future year, that's fine. But the truth
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is, you can't really ever outrun that
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tax problem except by dying. Yes, by
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dying. When you die, your taxable estate
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goes to your heirs at a what's called a
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stepped up cost basis. And it totally
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wipes out the capital gains and it
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totally wipes out what would have been
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your tax bill. And that brings about a
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little side note, brings about a funny
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little pattern in financial planning
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circles where we have to balance two
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competing ideas. that the first idea is
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that everyone will die someday and we
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must treat death as a reality, as an
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eventuality. But the second idea is that
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we need to be a little cautious about
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treating death as a win and treating
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living as a loss. And this scenario is
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one example. You know, sweet, you die
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with unrealized capital gains and your
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heirs get a big win. It's true, but
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you're still dead and you didn't get to
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spend that money of yours while you were
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alive. or another one. You claimed
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social security at 62 and that ended up
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being super smart for you because you
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died at 71 and age 71 is well before the
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break even age for delaying social
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security. So, it's a good thing you
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claimed early and got yours. Well, who
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are we talking to here? The dead
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71year-olds. I mean, did they really win
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the game? Another one. Oh, man. Jesse,
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you're you're wasting $2,000 a year for
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30 years on term life insurance. What a
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waste. Well, are you saying I failed
00:07:07
because I'm surviving? So epicat the
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point here is that death is a a reality
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and eventuality for all of us eventually
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and I genuinely think there does come a
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time when for example we ought to
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prudently say should we realize you know
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capital gains for this ill sick
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87year-old or do we discuss the idea of
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their death because for that person if
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they're going to die soon does it make
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sense to realize capital gains right now
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yeah unfortunately at some point that
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conversation does become a reality but
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I'll get emails from a 55-year-old who
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thinks they're going to kick the can
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down the road on their highly
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appreciated tech stocks until they die
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30 years out, 40 years out in the
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future. So anyway, a funny little aside
00:07:46
there. Let's go back to the main program
00:07:47
here about this capital gains long short
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strategy, that kind of thing. So short
00:07:52
of dying like we talked about though,
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what these sort of loss strategies
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attempt to do again is create some
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losses this year while not actually
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losing you money on net. Now for
00:08:03
example, you know, Wes talks about a
00:08:04
long short strategy in his question.
00:08:07
these long short strategies. What
00:08:08
exactly is going on here? Well, often
00:08:10
what these strategies do is they use
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leverage, right? They use some form of
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borrowed money to give you extra
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investment exposure. It's a weird
00:08:17
concept. Let me see if I can explain it.
00:08:18
So, let's say you have $100 to invest,
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but on top of that, you borrow another
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$100 and that's the leverage. And the
00:08:25
leverage comes with a cost to it, right?
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Borrowing money, taking a loan, that has
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a cost. And so, we'll put a pin in that
00:08:30
cost for now, but you had a hundred of
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your own dollars and you borrowed a
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hundred more. So, you now have $200 to
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invest. and you choose to invest 150 of
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that into the S&P 500. If you want to
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get more technical, you're probably
00:08:42
building a direct index of the S&P 500
00:08:44
by owning all 500 companies. But either
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way, you have $100 invested in the S&P
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and that's long, right? In investment
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world, when you're betting for
00:08:53
something, that's considered long. When
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you're betting against something that's
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considered a short, like the big short.
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So anyway, this is a long short
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strategy. $150 is invested long in the
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S&P and then you take the remaining $50
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you have and you short the S&P 500. Yes,
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in some way you are betting against
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yourself, but on net though you have
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$150 long and you have $50 short. So
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your net exposure is $100 long. In other
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words, you have the same investment
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exposure as if you had only invested
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your own $100 in the S&P 500. Right?
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Even though you you have that borrowed
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money, you're actually not taking any
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extra investment risk with it. You're
00:09:31
not doing anything super risky, but you
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know that in most years, at least some
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part of your portfolio between the 150
00:09:38
long and the $50 short, at least one of
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those two parts is going to be at a
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loss. Or if you went the direct indexing
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route, you know that some of your
00:09:47
individual holdings, some of those
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individual companies are definitely
00:09:50
going to lose money on an annual basis.
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So, let's say some of your shorts lose
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money, you sell them. Those losses can
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then be used to offset other gains from
00:09:57
your portfolio. They can be used to
00:09:59
offset the taxes from Roth conversions,
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which would be an income tax or other
00:10:02
forms of income tax. The point is that
00:10:04
you can use your losses to offset taxes.
00:10:07
And your adviser, Wes, would likely say,
00:10:09
"Hey, and you didn't actually lose any
00:10:11
money because your longs are up. The
00:10:13
longs have these unrealized gains that
00:10:15
more than make up for the shorts losing
00:10:17
money." That's a totally factual
00:10:18
statement. The question is, and I'll go
00:10:20
into this in more detail, the question
00:10:21
is, would you have been better off just
00:10:23
being 100% long in the first place and
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not dealing with any of the losses in
00:10:28
the first place? I'd wager, at least for
00:10:30
a lot of people, the answer there is
00:10:32
yes. So, in my experience, the best
00:10:34
strategies for using any sort of kind of
00:10:37
capital losses to offset gains, it
00:10:39
occurs when the losses are incidental,
00:10:42
not when the losses are purposeful. And
00:10:44
not all of us in our investing lifetime
00:10:46
are going to have those incidental
00:10:48
losses in our lives, let alone on a on
00:10:50
an annual basis. And that's totally
00:10:52
okay. In other words, what I'm saying
00:10:54
here is for some people, your portfolio
00:10:56
will do nothing but go up. Or at least
00:10:58
it'll go up so much that by the time it
00:11:01
goes down, you're still up. You're not
00:11:03
below where you started because your
00:11:04
portfolio has grown so much since the
00:11:06
start. So if you find yourself in this
00:11:09
situation, that's not a bad thing. Your
00:11:11
portfolio is up. So sometimes you might
00:11:14
get some incidental losses and you can
00:11:16
use those incidental losses to offset
00:11:19
capital gains to offset some income
00:11:21
taxes. That's great. But one of the big
00:11:23
questions I have is should we let the
00:11:26
tax tail which might be a 15% tax tail
00:11:29
wag the investing dog which is going to
00:11:31
be 100% of the underlying money right
00:11:33
the investments themselves. Now direct
00:11:35
indexing has all the same issues. You
00:11:37
know this strategy what I should say a
00:11:38
long short direct indexing strategy has
00:11:40
all the same issues as all direct
00:11:42
indexing strategies which we discussed
00:11:43
on episode 121. You know those issues
00:11:46
are higher costs some tax pitfalls
00:11:48
especially when it comes to the wash
00:11:50
sale rule tracking error against the
00:11:52
index diminishing benefits over time
00:11:55
asset minimums. Only relatively wealthy
00:11:57
people can even begin to participate in
00:11:59
these strategies. And then it only
00:12:01
applies to taxable accounts here. Right?
00:12:03
None of this applies to retirement
00:12:04
accounts cuz those are all qualified in
00:12:06
the first place. There aren't gains,
00:12:07
capital gains. There aren't capital
00:12:08
losses inside of a retirement account.
00:12:10
But the diminishing benefit over time is
00:12:12
a really big one, Wes, that I want to
00:12:14
focus on. A lot of these strategies
00:12:16
require forever maintenance because if
00:12:19
you recall, you're not really making the
00:12:21
capital gains totally disappear. When
00:12:24
your direct index, if one side of your
00:12:26
long short portfolio is kicking off
00:12:27
losses, the other side is creating
00:12:29
unrealized gains. And so to liquidate
00:12:32
this direct index long short portfolio,
00:12:35
you would have to realize all those
00:12:37
gains and that flies in the face of what
00:12:39
you're trying to accomplish in the first
00:12:40
place. Who would do that? So what ends
00:12:42
up happening is you're going to have to
00:12:43
maintain this this strategy for a long
00:12:45
time. But the costs of a direct index
00:12:48
portfolio or the costs of a long short
00:12:50
portfolio where there's some some
00:12:52
leverage, those costs will still be
00:12:54
there for a long time. So if you're
00:12:56
choosing to pursue one of these
00:12:57
strategies, I think it's important to
00:12:59
look at what your tax savings might be,
00:13:01
you know, this year, next year, and
00:13:02
other high tax years, totally important
00:13:04
to look at that. And it's important to
00:13:06
see how much in losses your portfolio is
00:13:07
going to generate because as long as
00:13:09
markets generally go up over time, the
00:13:11
fact is you will have fewer and fewer
00:13:13
losses as time goes on. We call that
00:13:15
loss decay or tax alpha decay. And then
00:13:19
you're going to need to measure against
00:13:20
that how much indirect index fees you'll
00:13:23
expect to pay not just this year, not
00:13:25
just next year, but for decades. And it
00:13:28
probably does feel amazing. It is
00:13:30
amazing that an investor who pursues the
00:13:32
strategy might get 3% or 4% in tax alpha
00:13:36
or in extra performance that comes from
00:13:38
saving so much money on taxes, but
00:13:41
eventually that tax alpha will drop to
00:13:43
zero and the fund is no longer creating
00:13:45
any sort of meaningful losses for you to
00:13:47
use. And even if it was, you might not
00:13:49
be in a tax situation anymore to use
00:13:51
those losses, but you're still paying
00:13:54
half a percent, 3/4 of a percent, 1% per
00:13:56
year. And so the tax alpha that you got
00:13:59
when you first started the strategy is
00:14:01
slowly getting eaten away by the much
00:14:03
higher than normal fees that you're
00:14:05
paying. And the people who use the
00:14:06
strategy, quote unquote, the best the
00:14:08
best candidates for this strategy, I
00:14:09
should say, are not, you know, the
00:14:11
late60s retirees. They're people in
00:14:13
their 40s and 50s. They're the higher
00:14:15
earners in the best years of their
00:14:17
careers. They're getting paid maybe an
00:14:19
equity compensation from a publicly
00:14:20
traded company. These are the people who
00:14:22
might have to hold that direct index
00:14:24
long short strategy for 40 or 50 more
00:14:27
years less they want to realize all the
00:14:30
capital gains that they avoided in the
00:14:31
first place. But holding the strategy
00:14:33
for 30 or 40 or 50 years as I just
00:14:35
identified has its own big problems. So,
00:14:37
in summary, I have some serious
00:14:39
reservations about this strategy, and I
00:14:40
think for the vast majority of people
00:14:42
out there, including many of the
00:14:43
wealthier people who might be listening
00:14:45
right now, I'd be cautious here. As
00:14:47
Einstein said, this is not as simple as
00:14:49
possible. Thank you for the question.
00:14:51
Uh, Wes, here's a quick ad and then
00:14:54
we'll get back to the show. I love
00:14:56
getting your questions and some of you
00:14:57
ask me questions about the wealth
00:14:58
management firm I work for in Rochester,
00:15:00
New York. Others ask about the best
00:15:02
interest blog and this podcast, Personal
00:15:03
Finance for Long-Term Investors, which
00:15:05
operate without advertising, without
00:15:06
pushy sales, and with no pay walls. How
00:15:09
can the blog and podcast stay afloat
00:15:10
without me dumping my own money into it?
00:15:12
Well, to answer both those questions, I
00:15:14
want to point you to episode 78 of
00:15:16
Personal Finance for Long-Term
00:15:17
Investors. I intentionally recorded
00:15:19
episode 78 to shine light on those
00:15:21
topics and inform you how you are
00:15:22
actually helping and can continue
00:15:24
helping these projects carry forward.
00:15:26
So, if you've ever been curious about
00:15:27
the business of my blog and podcast, or
00:15:30
if you're curious about my day job in
00:15:31
wealth management, please check out
00:15:33
episode 78 and let me know what you
00:15:34
think. And now on to question two from
00:15:36
Cliff. As I get closer to my retirement,
00:15:38
I wonder how long my retirement savings
00:15:40
will last. My wife has some of her IRA
00:15:42
with a trusted broker who is suggesting
00:15:45
a 5% withdrawal rate. She asked how long
00:15:47
it will last and he said likely forever
00:15:49
because it should return 8% on average
00:15:51
and we would only be taking 5%. Do you
00:15:54
agree with this, Cliff? Thanks for the
00:15:56
question. And I believe the explanation
00:15:57
that this broker suggested to your wife
00:15:59
is on the too simple side of things. It
00:16:02
is too simple. After all, if we use the
00:16:04
broker's logic, if it's returning 8% on
00:16:06
average, why can't your wife withdraw
00:16:08
7.9% per year? I think the same logic
00:16:11
ought to apply, right? 7.9 is less than
00:16:13
8 and that should probably last forever,
00:16:15
too. So, there's a problem there. Let me
00:16:17
try to add a little bit of nuance to
00:16:19
what the broker said. I think what the
00:16:20
broker should have said is history would
00:16:23
suggest that your portfolio will return
00:16:24
8% per year on average and therefore
00:16:26
most of the time you could easily
00:16:28
withdraw 5% per year, maybe even a
00:16:30
little more and be totally fine.
00:16:32
However, this simple framework overlooks
00:16:35
a really important fact, which is that
00:16:37
the earliest years of your retirement
00:16:38
matter the most by far. If the early
00:16:41
years have very bad investment returns
00:16:43
for you, it creates this chain reaction
00:16:45
that affects the rest of your retirement
00:16:47
timeline. We call this the sequence of
00:16:49
returns risk. And in order to mitigate
00:16:51
that risk, we recommend planning your
00:16:53
withdrawal rate in the four to 5% range
00:16:56
at least to start and then we can
00:16:58
revisit that withdrawal rate over time.
00:17:00
Now, that's obviously a longer, more
00:17:02
complex statement than what the broker
00:17:04
said, but if the broker had said
00:17:05
something like that, I think it would
00:17:07
have been much closer to the truth. If
00:17:09
you look at how the 4% rule was
00:17:10
originally created, what you see is that
00:17:12
in more than 50% of historical
00:17:14
scenarios, we actually could have
00:17:16
withdrawn more than 6% per year. We
00:17:18
could have used a 6% rule adjusted up
00:17:20
for inflation every year and been
00:17:22
totally safe. In fact, in some
00:17:24
scenarios, you could have withdrawn more
00:17:25
than 8% per year and been totally safe.
00:17:28
But in the worst scenario, in the back
00:17:30
testing, you could only withdraw 3.9%
00:17:33
per year to avoid depleting your
00:17:35
portfolio. And again, that's with all
00:17:36
the 4% rule, Trinity study assumptions
00:17:38
of a 50/50 portfolio and etc., etc. We
00:17:41
won't get into all those details on this
00:17:42
episode. The point is that we draw the
00:17:45
line at 4% because in one of the 100
00:17:48
back tests, 3.9% was the place where it
00:17:52
failed. So that's why we draw the line
00:17:54
at 4%. And I think the question is,
00:17:56
should you let that one worst case
00:17:58
scenario define your retirement? And and
00:18:01
one of the big problems is just that
00:18:02
there's so much luck of the draw, right?
00:18:04
someone who retired in the early 1980s
00:18:06
and if you're not, you know, a student
00:18:08
of market history, a big bare market and
00:18:11
kind of the stagflationy7s
00:18:13
which were really bad that really ended
00:18:15
in in about 1982. Starting in 1982 was
00:18:19
what some people consider and and kind
00:18:20
of if you look at the numbers might be
00:18:22
the best bull market of all time. 1982
00:18:24
through 1999 stopped by the uh internet
00:18:28
bubble. And you could also point to
00:18:30
maybe like March of 2009 through today
00:18:32
as being another one of the greatest
00:18:34
bull markets of all time. Anyway, if you
00:18:35
retired in the early 1980s, you could
00:18:37
have lived your entire 30-year
00:18:38
retirement withdrawing more than 8% per
00:18:41
year adjusted each year for inflation,
00:18:44
right? They could have retired and and
00:18:45
think about that. The 4% rule means you
00:18:47
have to save 25x your portfolio. Well,
00:18:50
this particular retiree who retired in
00:18:52
the early 80s, they could spend more
00:18:54
than 8% per year. They could have
00:18:55
retired with only 12 times their annual
00:18:58
spending saved in their portfolio. They
00:19:00
don't need 25x. They only needed 12x.
00:19:03
But someone in the same circumstance as
00:19:04
retiring in the mid60s, they, as I
00:19:07
mentioned before, that was the the worst
00:19:08
case scenario. They could have only
00:19:10
withdrawn 3.9% per year and would have
00:19:13
needed the full 25 times their annual
00:19:15
spending to retire. And that's a massive
00:19:17
difference in how much you need to save
00:19:18
to retire. And it's solely due to, in
00:19:20
this case, the good or bad luck of
00:19:22
timing. So, here's my personal
00:19:25
recommendation or personal solution for
00:19:27
how to think about this problem. I think
00:19:28
you can use the true 4% rule as a
00:19:31
starting point, but only a starting
00:19:32
point because that 4% rule creates a
00:19:34
conservative bookend that kind of limits
00:19:37
one side of what your retirement might
00:19:38
look like. If you want an easy, but
00:19:41
admittedly still flawed, rule of thumb
00:19:43
to be a little more optimistic, it's
00:19:44
that a 5% withdrawal rate has been safe
00:19:47
in most historical scenarios. that a 6%
00:19:50
withdrawal rate has been safe for about
00:19:52
half of historical scenarios. And
00:19:54
obviously your specifics matter a lot
00:19:55
here. And I think if you're willing to
00:19:57
be flexible, specifically by decreasing
00:19:59
your spending during poor market
00:20:01
periods, then you're probably going to
00:20:03
avoid many of the bad outcomes that come
00:20:06
from higher withdrawal rates. When you
00:20:08
hear about the 4% rule, the 5% rule, the
00:20:10
6% rule, when you hear people like me
00:20:12
describing them to you on a podcast,
00:20:14
that particular retiree in the
00:20:16
simulation, so to speak, never adjusted
00:20:18
their spending once, right? There are
00:20:21
people, and there were investment
00:20:22
markets where the market was down 30%,
00:20:24
their portfolio was down, you know,
00:20:26
whatever, if they're if they're
00:20:27
halfinvested in stocks, their portfolio
00:20:29
might have been down 15 or 20%. Maybe
00:20:31
they lived through the.com bubble. Maybe
00:20:33
they lived through the great financial
00:20:34
crisis. Their stock side of their
00:20:36
portfolio was down 50%. And they never
00:20:39
once adjusted their spending. Now,
00:20:41
that's probably not realistic, right?
00:20:43
Most of you, most of us are going to
00:20:44
adjust your spending. So, that's why I
00:20:46
say if you're willing to be flexible,
00:20:48
specifically by decreasing your spending
00:20:49
during poor market periods, you'll
00:20:51
surely avoid many of the adverse
00:20:53
outcomes that come from higher
00:20:54
withdrawal rates. And then ultimately,
00:20:56
if you want precision, which many people
00:20:58
do, then your unique retirement
00:21:01
attributes and really what I think about
00:21:03
here is your unique kind of spending
00:21:04
profile over your retirement has to be
00:21:07
used to hone in on a better answer for
00:21:09
you. So again, because the 4% rule is
00:21:12
kind of based on some really rigid
00:21:13
inputs that went in to create it, we
00:21:15
need to add some flexibility to those
00:21:17
inputs. So what I think we should do
00:21:18
there is you should say, what exactly
00:21:20
does safely spend mean to you? How will
00:21:23
your spending change from year to year
00:21:24
throughout your retirement? How is your
00:21:26
portfolio allocated among different
00:21:28
assets? Because 4% rule is just 50%
00:21:30
stocks, 50% bonds. How long will your
00:21:32
retirement last? The 4% rule is based on
00:21:34
a 30-year retirement. Maybe your
00:21:36
retirement is going to be different.
00:21:37
What does inflation look like during
00:21:39
your retirement period? I realize that's
00:21:41
impossible to know, but inflationary
00:21:43
assumptions are extremely important for
00:21:45
any kind of projection, retirement
00:21:46
projection, especially over multiple
00:21:48
decades. And then of course, what will
00:21:50
investment returns look like during your
00:21:51
retirement? Again, impossible to know in
00:21:53
advance. But what is very uh easy to
00:21:56
find out and what I think we all need to
00:21:58
find out is basically if I spin the
00:22:00
dial, if I dial up or dial down
00:22:01
inflation, if I dial up or dial down
00:22:03
investment returns, how does that affect
00:22:06
my results? And that's where some
00:22:07
analytical retirement tools uh can do a
00:22:09
lot of heavy lifting. So, what I've
00:22:11
described here certainly isn't easier or
00:22:13
simpler than what Cliff's wife's broker
00:22:16
said. It's much more nuanced than what
00:22:17
Cliff's wife's broker said. But I think
00:22:20
it's important that we understand that
00:22:21
not everything can be simplified all the
00:22:24
way down to hey so easy that a third
00:22:27
grader can do it. So thank you Cliff.
00:22:28
Good question. I appreciate you writing
00:22:30
in. And now Q3 is from Lucy. Lucy says
00:22:33
we're both 60 years old and looking to
00:22:35
retire soon. My husband has been sending
00:22:36
me some articles that really push for
00:22:38
both of us to claim social security as
00:22:40
early as possible due to future social
00:22:42
security liquidity concerns. Can you
00:22:45
play devil's advocate against his idea?
00:22:47
Lucy, I would love to be the person. I'd
00:22:49
love to be the man who argues against
00:22:51
your husband. That's definitely a role
00:22:53
that I want. You know what? Just call me
00:22:54
up anytime you want. If you want to
00:22:56
prove him wrong, I'm sure he's going to
00:22:57
understand and uh he'll just play along
00:23:00
nicely. Hey, a strange guy on the
00:23:01
internet with a podcast is telling me
00:23:03
how I'm wrong. No, I'm kidding, Lucy.
00:23:05
I'm happy happy to help. And I hope I I
00:23:08
add enough nuance here to, you know,
00:23:10
maybe just expose your husband to some
00:23:12
interesting ideas that he hadn't thought
00:23:13
about before. Let's first discuss the
00:23:15
liquidity or viability of social
00:23:17
security itself and then we'll talk
00:23:19
about the good, better, and best social
00:23:20
security claiming strategies. So yeah,
00:23:23
will social security still be there when
00:23:24
you need it to be? Many of you might
00:23:26
have seen or heard that the social
00:23:28
security trust fund could be depleted
00:23:30
sometime in the mid 2030s. And to many
00:23:33
people that sounds like the system is
00:23:35
about to break apart and and probably
00:23:37
will stop paying benefits. But that is
00:23:39
not the truth. And that's far far far
00:23:41
from what the projections actually say.
00:23:43
So when the trust fund reserves are
00:23:45
depleted again 2033, 2034, 2035, social
00:23:48
security will still be there. What's
00:23:50
going to happen though is that incoming
00:23:52
payroll taxes are going to fund most of
00:23:54
the benefits. And and that's actually
00:23:56
what's going on today. It's just that
00:23:57
most of us don't realize it. Every
00:23:58
working person, right, pays social
00:24:00
security taxes every year. And those
00:24:02
taxes currently support something like
00:24:05
80% of all the social security outflows.
00:24:07
The trust fund, which is going to run
00:24:09
out eventually, the trust fund covers
00:24:11
the remaining 20%. So, if the trust fund
00:24:14
went away today, the current social
00:24:16
security taxes that we are all paying
00:24:18
would make retirees about 80% whole.
00:24:21
Now, that's not a good outcome.
00:24:23
Obviously, we don't want that. We
00:24:24
shouldn't accept that. We want to make
00:24:26
everybody 100% whole. But what I just
00:24:28
described being 80% whole is far
00:24:30
different than saying that your social
00:24:32
security benefit is going to zero. If
00:24:34
you'd rather have a story that deals
00:24:36
with numbers, think of this. 70 million
00:24:38
Americans collect Social Security
00:24:40
benefits today. And looking at the
00:24:41
population distribution by age, those
00:24:44
numbers are pretty unlikely to change
00:24:45
over the next 10 years. So again, 70
00:24:47
million people will be collecting social
00:24:49
security roughly by the mid 2030s. All
00:24:52
of them are voters, right? They're over
00:24:53
the age of 18. And if you tell 70
00:24:55
million people that their income is
00:24:57
going to get cut either by $2,000 a
00:25:00
month if the system just totally
00:25:01
disappears or by even $400 a month,
00:25:04
which would be if the benefit cut gets
00:25:06
cut down to the 80% number, those 70
00:25:08
million people are not going to like
00:25:10
that outcome. And so where there's a
00:25:11
will, there's a way. And I would bet
00:25:13
that the retired electorate has a will
00:25:15
to not let Social Security benefits get
00:25:17
cut. Now, according to projections from
00:25:20
the Social Security Administration,
00:25:21
closing the gap could be achieved with a
00:25:24
bunch of different policy changes.
00:25:26
Increasing payroll taxes, which wouldn't
00:25:27
be fun. Raising or eliminating the
00:25:30
taxable wage cap, that's an interesting
00:25:31
one. You might know that only the first
00:25:33
$180,000 of someone's earned income is
00:25:36
subject to social security tax. You
00:25:38
know, Warren Buffett, who you know, I'm
00:25:40
a fanboy of, he loved to call out the
00:25:41
the BS on this fact because he paid the
00:25:44
same amount of social security tax each
00:25:46
year, which was about $10,000 on the
00:25:49
180,000. So, you know, Warren Buffett is
00:25:51
paying $10,000 a year in social security
00:25:53
taxes, and so was his secretary, right?
00:25:56
Every dollar that Warren Buffett earned
00:25:57
over $180,000 in a year is not subject
00:26:00
to social security tax. So, if they
00:26:02
raise that cap, it's an additional tax
00:26:05
basically on the highest income earners
00:26:07
for sure. But yeah, it would help close
00:26:08
that gap. Other policy changes, they
00:26:10
could gradually adjust benefits. I think
00:26:12
this is possible and likely. They could
00:26:14
increase the retirement age modestly. I
00:26:16
think that is also quite possible and
00:26:18
likely. And I think there's a unique
00:26:19
take that I haven't really heard
00:26:20
mentioned very often. They could
00:26:22
actually lower the retirement age below
00:26:24
62, but then pair that with a relatively
00:26:27
severe throttling of the benefits
00:26:29
themselves. You know, right now you
00:26:31
might know that collecting at age 62
00:26:33
gives you 70% of your full retirement
00:26:35
benefit. Or in other words, you take a
00:26:37
30% haircut for life if you choose to
00:26:40
collect uh social security at age 62.
00:26:42
Well, what if they allowed you to
00:26:44
collect at age 60 with a 50% haircut for
00:26:46
life or whatever the numbers have to be?
00:26:48
Cuz again, I putting myself in the shoes
00:26:50
of an actuary. I we need to do something
00:26:52
that lessens the overall stress to the
00:26:54
social security system. And there is a
00:26:56
way to say, "Yeah, we'll let you collect
00:26:58
early, but we'll give you such a big
00:27:00
haircut that actually it ends up being
00:27:02
better for the system overall." And none
00:27:04
of those changes require dismantling the
00:27:05
system. So Lucy, I think it's fair to
00:27:07
share those ideas with your husband.
00:27:09
It's very unlikely that Social Security
00:27:10
will be going away. And now that brings
00:27:12
us to the optimal time to collect. Let's
00:27:14
start with something obvious and simple,
00:27:16
but pretty important. If you knew
00:27:17
exactly when you and your spouse were
00:27:19
going to die, then you could precisely
00:27:20
pick your best, most ideal social
00:27:23
security claiming dates. And of course,
00:27:24
you don't know that. But I think it's
00:27:26
important to make the most educated
00:27:28
guess that we can because when it comes
00:27:30
to an optimal strategy, what we have to
00:27:32
do here is say, well, the probability
00:27:34
suggests that we are going to die at
00:27:36
ages A and B and therefore we should
00:27:38
claim our social security in this way.
00:27:40
Social Security uses this concept called
00:27:42
full retirement age, FRA, full
00:27:44
retirement age, to determine how much
00:27:46
your eligible benefit you will get to
00:27:47
collect. Your personal full retirement
00:27:49
age depends on the year you were born.
00:27:51
For most of well I shouldn't say for
00:27:53
most for all of today's retirees it's
00:27:55
either 67 or 66 or maybe 66 in a certain
00:27:58
number of months as I just alluded to
00:28:00
you can start collecting at age 62 or
00:28:03
before your full retirement age but
00:28:04
there's a price to pay and your benefits
00:28:06
will be permanently reduced but then if
00:28:08
you wait to collect until after your
00:28:10
full retirement age then your benefits
00:28:12
will be permanently increased. Now if
00:28:14
there's just one person involved so
00:28:16
there's not a spouse involved just yet.
00:28:17
If there's just one person involved and
00:28:19
all you have to think about is your own
00:28:20
benefit, then the pure logic and the
00:28:22
pure math is pretty straightforward. It
00:28:24
basically says if you die before age 77,
00:28:27
then collecting as early as possible
00:28:28
would have been best. But again, we have
00:28:30
to go back to earlier where it's like,
00:28:32
well, if you die early, is that really a
00:28:33
win? I know, I know. But pure math and
00:28:35
logic says if you die before age 77, you
00:28:38
will have wished you started collecting
00:28:39
social security at age 62. If you die
00:28:42
between ages like 78 and 80, early 80s,
00:28:45
then all the scenarios, all the ages are
00:28:47
roughly equal. And then really if you
00:28:49
die after age 80, especially it becomes
00:28:52
really clear if you die like after age
00:28:54
82, then having waited until age 70 to
00:28:58
start collecting will have been best in
00:29:00
hindsight, right? I think this makes
00:29:02
sense because your benefit goes up if
00:29:04
you wait to collect till 70 and
00:29:05
therefore the longer you live after age
00:29:07
70, the more likely that is to have
00:29:09
turned out to been a smart decision. But
00:29:11
there is much more to consider here. And
00:29:12
I think to get to the real meat of the
00:29:13
answer, you know, what are some
00:29:15
applicable strategies, thought
00:29:16
processes, if then scenarios that can
00:29:18
guide you and your family in social
00:29:20
security decisions? The poker player
00:29:22
Annie Duke, she'd like to say that two
00:29:24
things determine the outcomes in your
00:29:26
life. Thing one is the quality of your
00:29:28
decisions and thing two is luck. So, put
00:29:31
another way, there are some things in
00:29:32
your control and some things out of your
00:29:34
control. And so, whatever decision you
00:29:36
make regarding social security, you have
00:29:38
to accept that luck might strike and
00:29:39
your decision won't have been the
00:29:41
optimum one. And it's not because you
00:29:42
made a bad decision. It's just because
00:29:43
of luck. Even though bad luck might
00:29:45
screw you over, you still want to make a
00:29:47
a high quality decision if you can. You
00:29:48
want to try to get this right. So, let
00:29:50
me start with this. Social Security is
00:29:52
pretty close to a one-way decision that
00:29:54
you cannot undo. But the exception to
00:29:56
that is that once you start collecting
00:29:57
social security, you do technically have
00:29:59
up to 12 months to change your mind. And
00:30:02
if you do change your mind, then you
00:30:03
have to repay any of the benefits that
00:30:05
you'd received so far. They call that a
00:30:07
withdrawal. And you get one of those
00:30:08
withdrawals in your lifetime. A little
00:30:10
known fact, you can undo your decision
00:30:12
to start claiming Social Security. But
00:30:14
once you delay Social Security, right,
00:30:15
you can never go back in time and
00:30:17
reclaim your missed benefits. You can't
00:30:19
be 67 years old having never claimed and
00:30:22
say actually I want to retroactively go
00:30:24
back to 63 and and start collecting. So
00:30:26
ideally that's why you want to get this
00:30:28
decision right. You know in a perfect
00:30:30
world you you get it right the first
00:30:31
time. So let's think about you and your
00:30:33
spouse. Spousal benefits and survivor
00:30:35
benefits two different things. Spousal
00:30:37
benefits and survivor benefits. Many
00:30:39
rabbit holes in social security
00:30:41
planning. And spousal and survivor
00:30:43
benefits are two of those rabbit holes.
00:30:44
And I I mean rabbit holes because there
00:30:46
are many paths and they go pretty deep
00:30:47
and it's easy to get lost. The upshot
00:30:50
for basic social security planning is
00:30:52
that your decision to collect social
00:30:54
security not only affects you, but it
00:30:57
could affect your current spouse. It
00:30:59
could affect your expouse andor it could
00:31:02
affect your future spouse or your future
00:31:04
widow. So basically, it doesn't matter
00:31:06
who you're married to now, who you were
00:31:08
married to in the past, or who you might
00:31:10
be married to in the future. your
00:31:11
decision to collect social security is
00:31:14
likely going to affect them. So let's
00:31:16
say Bob has a primary insurance amount
00:31:18
of $3,200 a month. Again, that primary
00:31:20
insurance amount that represents what
00:31:21
Bob would have collected if he collects
00:31:23
at his full retirement age. So if he
00:31:25
collects early, it's going to be less
00:31:26
than 3200 a month. If he collects late,
00:31:28
it's going to be more than 3200 a month.
00:31:30
But we'll say Bob's primary insurance
00:31:32
amount is 3200 a month. Bob's married to
00:31:34
Sharon. Her PIA is 1,200 a month. And
00:31:38
let's say to make this simple, they both
00:31:39
opt to start collecting at full
00:31:41
retirement age. And thus, they're
00:31:42
collecting exactly 100% of the PIA
00:31:45
numbers we just described. 3200 for Bob,
00:31:48
1,200 for Sharon. Well, right off the
00:31:50
bat, Sharon will be collecting something
00:31:52
called a spousal benefit. Now, why? It's
00:31:54
because Sharon's benefit 1,200 is less
00:31:57
than half of Bob's. Bob's 3200. Half of
00:32:00
3200 is 1,600. So, Sharon's 1,200 is
00:32:04
less than half of Bob's. So, she is
00:32:06
eligible for 50% of Bob's PIA or $1,600
00:32:10
a month. So, she's going to collect her
00:32:12
own $1,200 benefit and then she's going
00:32:14
to get an additional $400 a month at no
00:32:17
sort of penalty to Bob at all. There's
00:32:19
no penalties involved. No one is losing
00:32:21
any benefits here. It's just that as a
00:32:23
spouse, you are eligible for 50% of your
00:32:26
spouse's PIA. And yes, Sharon is
00:32:29
collecting this while she's alive and
00:32:30
and while Bob is alive. This is the
00:32:32
spousal benefit and the ages that Sharon
00:32:34
and Bob choose to collect social
00:32:36
security. Again, if they had chosen to
00:32:37
collect early, if they had chosen to
00:32:39
collect late, those decisions do affect
00:32:41
what the spousal benefit looks like. So,
00:32:43
it's important to know that. Now, what
00:32:45
if Bob dies? Well, notably, if Bob dies,
00:32:48
Sharon is going to step up into Bob's
00:32:50
full benefit, receiving the full $3,200
00:32:53
a month that that Bob was receiving.
00:32:55
Sharon's own benefit would would drop
00:32:57
away. However, if Bob had started
00:32:59
collecting early at age 62, his benefit
00:33:02
would have only been about $2,300 a
00:33:04
month. And after Bob died, Sharon would
00:33:06
step into that $2,300 per month benefit.
00:33:09
And if Bob had started collecting, say
00:33:11
at age 70, his benefit actually would
00:33:12
have been about $4,000 a month. And
00:33:14
Sharon would have stepped into that
00:33:16
$4,000 a month benefit when Bob died. So
00:33:19
the point is that Bob's decision to
00:33:21
collect at 67 and collect $3,200 a
00:33:24
month. It didn't only affect his benefit
00:33:26
while he lived. It also had these side
00:33:28
effects on Sharon's benefits both while
00:33:30
they were alive and after Bob died. So
00:33:33
the point is again that spouses need
00:33:35
careful consideration when deciding when
00:33:37
to claim social security. They need to
00:33:39
consider various scenarios for which
00:33:41
spouse dies first and at which ages. So
00:33:44
some rules of thumb for you when it
00:33:45
comes to these spousal and survivor
00:33:47
benefits. Again, it's a spousal benefit
00:33:49
when they're both alive and Sharon was
00:33:51
collecting half of Bob's benefit. It
00:33:53
becomes a survivor benefit once Bob died
00:33:55
and then Sharon steps into Bob's full
00:33:57
benefit. So some rules of thumb here
00:33:59
that apply in a lot of cases, maybe not
00:34:01
every case, but apply in a lot of cases
00:34:03
is that the lesser earning spouse, so in
00:34:05
this case, Sharon, the lesser earning
00:34:07
spouse can often start collecting social
00:34:09
security as early as possible, but that
00:34:12
the higher earning spouse should delay
00:34:14
social security as long as possible to
00:34:16
age 70 because again, their decision to
00:34:19
do so has a 100% chance of affecting
00:34:21
their own benefit, but then also has a
00:34:24
roughly 50% chance of affecting their
00:34:26
spouse's eventual benefit. with, you
00:34:28
know, the Sharon and Bob scenario being
00:34:30
a perfect example. If Bob had waited
00:34:32
till 70, his own benefit would have been
00:34:34
higher while he was alive and also
00:34:36
Sharon's benefit would have been higher
00:34:37
after Bob died. Now, I think it's okay
00:34:40
too to dig into the probabilities of who
00:34:41
dies first. You know, to think of
00:34:43
health, illness, family history, that
00:34:45
kind of thing. The most common questions
00:34:47
that you can ask yourself surrounding
00:34:49
your kind of a married couple's decision
00:34:51
to collect social security revolve
00:34:53
around your personal health and and
00:34:54
family history. You should ask, does
00:34:56
anything there in your personal or
00:34:58
family history point to either an early
00:35:00
or a late death? If you're healthy and
00:35:02
all your relatives live to 100, it's
00:35:04
reasonable to assume that you might have
00:35:06
a similar fate. If you're chronically
00:35:08
ill and your relatives have all passed
00:35:09
away early, again, you could reasonably
00:35:11
assume that you might have a similar
00:35:12
fate. Certainly not a doctor here, but
00:35:14
the idea is that they say genetics load
00:35:16
the gun and environment pull the
00:35:17
trigger. The idea is, you know, yeah,
00:35:19
you aren't condemned to your family
00:35:20
history. You do have dials to control.
00:35:22
Don't forget that. But it's worth
00:35:24
understanding what either your family
00:35:26
history or your personal health history
00:35:27
looks like. Next, I would ask yourself,
00:35:30
do you really need to take Social
00:35:32
Security early? Like truly, do you have
00:35:34
a financial need to take it early?
00:35:35
Because if that extra income is going to
00:35:37
bridge the gap between cat food and a
00:35:40
normal human diet, well, maybe you have
00:35:42
to take it early. But if you don't need
00:35:43
it, why are you taking it early?
00:35:45
Delaying Social Security acts as
00:35:47
longevity insurance. In fact, the full
00:35:49
name of the Social Security program for
00:35:51
retirees has longevity insurance right
00:35:54
there in the name. So, protecting
00:35:55
against the risk that you're going to
00:35:57
live to 90 or 95 or beyond, that's
00:36:00
pretty important. And the longer you
00:36:01
wait, the higher your benefit will be
00:36:03
and the better your long-term outcomes
00:36:05
will be. Now, going back to Lucy's
00:36:07
original question, she mentioned that
00:36:08
they're retiring soon. But what if
00:36:09
someone wanted to keep on working? Are
00:36:11
there any interactions between your
00:36:13
normal work income and social security
00:36:14
income? The short answer here is yes.
00:36:17
there's a negative interaction if you
00:36:18
are younger than your full retirement
00:36:20
age, but there's no negative interaction
00:36:23
if you are at your full retirement age
00:36:25
or older. So, for that reason, it very
00:36:27
rarely ever makes sense for someone to
00:36:29
claim social security early if they are
00:36:31
also still working. But it can make
00:36:33
sense for someone to claim social
00:36:34
security at full retirement age even if
00:36:36
they are still working. You know, I
00:36:38
think the next idea is I think using
00:36:40
social security as a possible sequence
00:36:42
risk buffer can be a great idea. Again,
00:36:44
the idea is that you might start
00:36:45
retirement without having claimed social
00:36:47
security. Your plan is to live off your
00:36:49
portfolio, but if the markets perform
00:36:51
poorly and all of a sudden you realize
00:36:53
that you're subject or you're exposed to
00:36:55
some sequence risk because of that poor
00:36:56
performance. What do you want to do in
00:36:58
that situation? Well, in a perfect
00:37:00
world, you would give your portfolio
00:37:01
time to recover. You would lessen your
00:37:04
withdrawals in order to leave more money
00:37:06
in your portfolio to recover. How do you
00:37:08
lessen your withdrawals? Of course, you
00:37:10
can cut out spending. You can be
00:37:11
flexible like we mentioned a few minutes
00:37:12
ago. You can also turn on social
00:37:14
security and boom, right there you say,
00:37:16
"Oh, we have an extra $3,000 a month
00:37:19
coming in. That's $3,000 a month that
00:37:21
doesn't have to come out of my
00:37:22
portfolio." And that really does kind of
00:37:24
dampen or buffer your risk against a a
00:37:26
sequence of return risk. And last, I'd
00:37:28
consider some uh taxability concerns.
00:37:30
So, generally, claiming Social Security
00:37:32
will reduce your ability to do smart tax
00:37:34
planning, and it's certainly not the end
00:37:36
of the world, but it is a secondary cost
00:37:38
worth considering. In a perfect world,
00:37:40
you would leave your options open to do
00:37:42
smart tax planning. And the more income
00:37:44
coming in, usually the fewer
00:37:45
opportunities you have, and social
00:37:46
security does count as income. So, in
00:37:49
short, there aren't many situations
00:37:50
where I'd recommend a married couple
00:37:52
both collect early as possible. Lucy,
00:37:54
there might be one exception for being
00:37:56
really open-minded is that if both
00:37:58
spouses have a really poor health
00:37:59
history and a poor family health
00:38:00
history, suggesting that both of them
00:38:02
are likely to pass away before break
00:38:04
even age, I could see both of them
00:38:06
claiming early. But either way, many,
00:38:08
many different considerations when it
00:38:09
comes to social security claiming. Most
00:38:11
of those considerations suggest that at
00:38:13
least one of the two spouses delay their
00:38:15
claiming to 60 or 67. Here's a quick ad
00:38:18
and then we'll get back to the show. I
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00:39:08
And last question for today from Nicole
00:39:10
Jesse, could you please do an AMA
00:39:12
question about rebalancing your
00:39:13
portfolio? I feel like different experts
00:39:15
talk about doing it quarterly, doing it
00:39:17
twice a year, doing it once a year. A
00:39:18
lot of people talk about doing it based
00:39:20
on the calendar in that way, but then
00:39:21
other people talk about drift. For
00:39:23
example, if your 60/40 portfolio drifts
00:39:26
more than 5%, say to 65% stocks or to
00:39:29
55% stocks, then you rebalance it. How
00:39:32
do you rebalance, Jesse, and why? Well,
00:39:34
this is an awesome question, Nicole, and
00:39:35
and selfishly, I admit, I think it's
00:39:37
awesome because it gives me a chance to
00:39:39
really to flesh out some of my personal
00:39:41
thoughts on something I've always had a
00:39:43
a feeling for in the back of my mind.
00:39:44
I've never really gotten it out on
00:39:46
paper. And truthfully, I've never dug
00:39:48
into any sort of like alternative view
00:39:50
or what researchers have to say. So all
00:39:52
of a sudden now through answering this
00:39:54
question, I feel like I've really kind
00:39:55
of solidified my own opinion on it. So
00:39:58
it's just a win-win. So listeners, if
00:40:00
you're not familiar with rebalancing,
00:40:02
Nicole described it pretty well in her
00:40:04
question. So thank you, Nicole. The idea
00:40:05
is that an investor might decide, okay,
00:40:07
my portfolio should be 60% stocks and
00:40:10
40% bonds. Okay, that's great. But as
00:40:12
the value of that investor's stocks and
00:40:14
bonds change over time, their original
00:40:16
60/40 allocation is going to change,
00:40:18
too. And the act of rebalancing is that
00:40:20
investor deciding to bring the portfolio
00:40:22
back to 60/40. So the question is when
00:40:25
should that happen? But first I think a
00:40:27
good place to start this answer is why
00:40:29
do we need to rebalance in the first
00:40:30
place? Well, it's pretty simple. We do
00:40:32
need to rebalance to ensure that our
00:40:34
portfolio has the proper amount of risk
00:40:36
and so that our portfolio meets the
00:40:38
needs of our financial plan. We do not
00:40:40
need to rebalance because that's the way
00:40:42
to improve our long-term returns. So
00:40:44
I'll say that again. We do not and
00:40:46
should not assume that rebalancing will
00:40:48
lead to better long-term returns. It
00:40:50
might, but it might not. Increasing your
00:40:53
returns is not one of the reasons to
00:40:54
rebalance. So, the reason, as I said a
00:40:56
minute ago, is to make sure that your
00:40:58
portfolio is still doing what you need
00:41:00
it to do. It still has the right amount
00:41:02
of risk in it. It still has the right
00:41:03
amount of potential growth in it to meet
00:41:05
your long-term needs. It's all about
00:41:06
meeting your long-term financial plan.
00:41:09
Or another thing is, you know, I've
00:41:10
talked about it here before. I usually
00:41:12
look at everyone's portfolio through
00:41:13
some sort of asset liability matching
00:41:15
lens and we want to make sure that
00:41:17
everyone's portfolio has the right
00:41:18
amount of assets to meet their
00:41:19
short-term needs, their midterm needs,
00:41:21
their long-term needs. So sometimes we
00:41:23
need to rebalance to ensure we're doing
00:41:24
that. And so what happens if you don't
00:41:26
rebalance? Well, not rebalancing a
00:41:28
portfolio will cause it to drift from
00:41:30
its original target allocation, perhaps
00:41:32
resulting in these unintended
00:41:33
concentrations in your top performing
00:41:35
assets, often stocks, which brings
00:41:37
increased vulnerability to market
00:41:39
downturns. And so while the lack of
00:41:41
rebalancing may allow for higher returns
00:41:43
during bull markets, it can lead to
00:41:45
bigger losses during bare markets. So
00:41:47
with that preamble, let's now answer the
00:41:49
question, how often should you be
00:41:51
rebalancing? So first and foremost, you
00:41:53
can and should consider using your just
00:41:55
your normal portfolio activities to more
00:41:57
easily rebalance. Meaning every single
00:42:00
portfolio has some dividends coming in
00:42:02
or some interest, some new contributions
00:42:04
going into your accounts or some
00:42:05
withdrawals coming out of your accounts,
00:42:07
right? money is already moving in and
00:42:08
out of your accounts and in and out of
00:42:10
your portfolio. So, you can and probably
00:42:12
should use that money as part of your
00:42:14
rebalancing strategy anyway. If you're
00:42:16
contributing $1,000 a month into a
00:42:18
taxable brokerage account and that
00:42:20
account currently has too many stocks in
00:42:22
it, well, maybe you decide to have all
00:42:24
1,000 of your new 1,000 per month going
00:42:26
only into bonds for a few months. You
00:42:28
can rebalance that way. You don't need
00:42:30
to sell your stocks to rebalance.
00:42:31
Instead, you just use the new deposits.
00:42:33
Similarly, you could choose to turn off
00:42:35
dividend reinvestment for a while and
00:42:37
use all those portfolio income sources
00:42:40
to only go into one specific asset to
00:42:42
achieve some rebalancing over time. But
00:42:44
often times doing something like that
00:42:46
isn't actually enough. You need to take
00:42:48
some action above and beyond that to
00:42:50
achieve rebalancing. And as Nicole
00:42:52
mentioned in her question, the two most
00:42:53
popular styles of rebalancing are
00:42:55
timebased, once a quarter, twice a year,
00:42:57
once a year, something like that. And
00:42:59
then driftbased or threshold-based. You
00:43:01
rebalance when your assets get 5% out of
00:43:03
whack or 10% out of whack or you
00:43:05
rebalance when a particular allocation
00:43:07
is 25% different when it started than
00:43:09
than when it started. You know, if you
00:43:10
have a 5% allocation to small cap value
00:43:13
and that 5% goes down to 3%. Well,
00:43:15
that's a 40% change. So anyway, you can
00:43:18
have some thresholds set there. Now,
00:43:20
strictly speaking and you know, kind of
00:43:21
in theory, a drift or threshold strategy
00:43:24
makes a lot more sense because you're
00:43:26
rebalancing based on the characteristics
00:43:28
of the portfolio itself. the portfolio
00:43:30
and its risk are out of whack. That's a
00:43:32
great reason to rebalance. A
00:43:34
calendar-based strategy, on the other
00:43:36
hand, might dictate rebalancing when
00:43:38
it's really not needed. Like, okay, it's
00:43:39
October again. Well, what does October
00:43:42
have anything to do with your portfolio?
00:43:44
It's arbitrary, is my point. But the
00:43:46
problem, and this problem exists with
00:43:48
any rebalancing strategy, is to consider
00:43:50
the costs of doing so. There aren't that
00:43:52
many trading costs these days, which is
00:43:54
a good thing. But you still ought to be
00:43:56
aware of trading costs. They do exist.
00:43:58
Some of the mutual funds you own might
00:43:59
have a trading cost associated with
00:44:01
them. Taxes are another cost at least
00:44:03
inside of a taxable account. And then
00:44:05
your time is another cost, even though
00:44:07
sure that's a bit subjective. Some of
00:44:08
you uh it might be really easy for you
00:44:10
to rebalance cuz your simple portfolio
00:44:12
and you're pretty good at the math. And
00:44:14
for others of you, it might be a real
00:44:15
chore to rebalance. But the point is,
00:44:17
the more you rebalance, the more costs
00:44:18
you might be incurring. So, if your
00:44:20
threshold rebalancing strategy has you
00:44:22
making trades every single month, is
00:44:24
that really better than a a
00:44:25
calendarbased strategy that recommends
00:44:27
you do it once a year? So, that's what a
00:44:29
Vanguard research team wanted to look
00:44:31
into. And they published a paper in
00:44:32
2022, I'll link it here in the show
00:44:34
notes, that attempted to answer those
00:44:35
kind of questions. They tested all sorts
00:44:37
of various rebalancing strategies for
00:44:39
different portfolios. And they concluded
00:44:41
that for just about any portfolio
00:44:42
allocation, the optimal rebalancing
00:44:44
strategy is either once per year or once
00:44:48
per year only if your target allocation
00:44:51
is more than 1% out of whack. And those
00:44:53
two conclusions, they're basically the
00:44:55
same thing in my opinion. So anyway, the
00:44:57
whole point is it's once a year. The
00:44:58
optimal portfolio rebalancing strategy
00:45:00
is once a year. They looked at other
00:45:02
time periods, too. They found that daily
00:45:03
rebalancing is the worst thing you could
00:45:05
possibly do, but the next worst thing is
00:45:08
never rebalancing at all. And then if
00:45:10
we're going from worst to best, then
00:45:12
comes weekly, monthly, bimonthly, and
00:45:14
quarterly. So the point there is that
00:45:16
doing rebalancing too often, especially
00:45:17
if it has some legitimate trading costs
00:45:19
to it is more detrimental. And just
00:45:22
rebalancing once a year, was their
00:45:23
optimal solution. So how do we actually
00:45:26
execute that? Well, I think we still
00:45:28
want our routine portfolio activities,
00:45:30
again, the dividends and the interest,
00:45:31
the deposits and the withdrawals. We
00:45:32
still want those routine activities to
00:45:34
take rebalancing into account. If our
00:45:37
portfolio is drifting, there's nothing
00:45:39
wrong with using those activities to
00:45:41
bring the allocation back in line. And I
00:45:43
guess the reason why I say that is
00:45:44
because those activities are happening
00:45:45
anyway. There's no additional cost to
00:45:47
them because they're happening anyway.
00:45:49
You're playing with house money is the
00:45:50
way to think about it. So, you might as
00:45:52
well rebalance if you're playing with
00:45:53
house money. But beyond those routine
00:45:55
activities, we want to set a once-yearly
00:45:58
reminder to rebalance. And candidly, I
00:46:00
think that once yearly reminder can
00:46:01
serve as a time when you revisit your
00:46:03
entire financial plan if you want to,
00:46:05
ensuring that the conclusions you
00:46:06
reached 12 months ago are still valid
00:46:08
today. You can revisit your allocation
00:46:10
itself to ensure it's still the right
00:46:11
allocation for what your financial plan
00:46:13
needs. And then, of course, you can
00:46:15
execute whatever trades are required to
00:46:17
bring your portfolio back into line. I
00:46:19
think that's a pretty simple solution,
00:46:21
possibly much simpler than some of the
00:46:23
rebalancing advice you see online, but
00:46:25
it's certainly not sitting back and
00:46:27
doing nothing. So Nicole, thank you for
00:46:28
the question and listeners, thank you
00:46:30
for the awesome questions today. I hope
00:46:31
this convinced you that financial
00:46:33
planning can be pretty simple, but at
00:46:35
the same time, there comes a point where
00:46:36
we have to say, "Ah, we can't be simpler
00:46:38
than that." Thank you as always for
00:46:40
sending in your awesome ask me anything
00:46:41
questions. You can send future questions
00:46:43
00:46:45
I look forward to reading your emails
00:46:47
and thank you once again for listening
00:46:48
to Personal Finance for Long-Term
00:46:50
Investors. Thanks for tuning in to this
00:46:52
episode of Personal Finance for
00:46:54
Long-Term Investors. If you have a
00:46:56
question for Jesse to answer on a future
00:46:58
episode, send him an email over at his
00:47:00
blog, The Bestin Interest. His email
00:47:03
address is [email protected].
00:47:06
Again, that's jessevestinterest.blog.
00:47:10
Did you enjoy the show? Subscribe, rate,
00:47:12
and review the podcast wherever you
00:47:14
listen. This helps others find the show
00:47:16
and invest in knowledge themselves. And
00:47:19
we really appreciate it. We'll catch you
00:47:20
on the next episode of Personal Finance
00:47:23
for Long-Term Investors. Personal
00:47:25
Finance for Long-Term Investors is a
00:47:27
personal podcast meant for education and
00:47:29
entertainment. It should not be taken as
00:47:31
financial advice and it's not
00:47:33
prescriptive of your financial
00:47:34
situation.

Episode Highlights

  • The Complexity of Retirement Planning
    Retirement planning often becomes overcomplicated, but simplicity is key. As Einstein said, 'Everything should be as simple as possible, but no simpler.'
    “Everything should be as simple as possible, but no simpler.”
    @ 01m 29s
    May 06, 2026
  • Understanding Capital Gains and Losses
    Generating investment losses can offset gains, but it's crucial to weigh the risks. Would you rather pay taxes on gains or have no gains at all?
    “Why lose $10,000 to save $1,500?”
    @ 04m 40s
    May 06, 2026
  • The Reality of Death in Financial Planning
    Financial planning must consider the inevitability of death, balancing the benefits of tax strategies with the reality of living.
    “Death is a reality and eventuality for all of us.”
    @ 07m 11s
    May 06, 2026
  • Understanding the 4% Rule
    The 4% rule suggests a conservative withdrawal rate for retirement savings, but historical data shows flexibility may be possible.
    “In more than 50% of historical scenarios, we could have withdrawn more than 6% per year.”
    @ 17m 10s
    May 06, 2026
  • Social Security's Future
    Despite concerns about the social security trust fund, benefits are likely to continue with adjustments.
    “It's very unlikely that Social Security will be going away.”
    @ 27m 10s
    May 06, 2026
  • Impact of Claiming Strategies
    Your social security claiming strategy can significantly affect your benefits and those of your spouse.
    “Your decision to collect social security affects not just you, but your spouse too.”
    @ 30m 52s
    May 06, 2026
  • The Impact of Social Security Decisions
    Bob's choice to collect Social Security at 67 affected both his and Sharon's benefits.
    “Bob's decision didn't only affect his benefit while he lived.”
    @ 33m 21s
    May 06, 2026
  • Understanding Health and Social Security
    Personal health and family history can influence when to claim Social Security.
    “Does anything in your personal or family history point to an early or late death?”
    @ 34m 56s
    May 06, 2026
  • Optimal Rebalancing Strategy
    Research suggests rebalancing your portfolio once a year is the best strategy.
    “The optimal rebalancing strategy is once a year.”
    @ 44m 57s
    May 06, 2026

Episode Quotes

  • Why lose $10,000 to save $1,500?
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
  • Death is a reality and eventuality for all of us.
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
  • If you want an easy, but admittedly still flawed, rule of thumb...
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
  • If there's a will, there's a way.
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
  • If you don’t need it, why are you taking it early?
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
  • The optimal rebalancing strategy is once a year.
    Making Retirement As Simple as Possible, but No Simpler (AMA, E138)

Key Moments

  • Simplicity in Finance01:29
  • Capital Gains Strategy04:40
  • Reality of Death07:11
  • Withdrawal Rate Planning16:53
  • Claiming Strategies27:14
  • Social Security Decisions33:21
  • Health Considerations34:56
  • Rebalancing Strategy44:57

Words per Minute Over Time

Vibes Breakdown

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