This Is Why Financially Ready People Struggle to Retire

Even with a strong financial plan in place, many professionals find themselves hesitating at the retirement decision—stuck in the cycle of “just one more year.” The numbers say it’s possible, yet the fear of leaving behind a paycheck, a title, or a sense of purpose keeps them working long past the point of “enough.”

This episode reframes retirement readiness through the lens of the five dimensions of wealth: financial, time, physical, social, and mental. Financial wealth is just one piece. Time wealth—measured in the limited seconds of healthy, vibrant life left—is often the most undervalued. Physical health determines whether retirement years are active or restricted. Social wealth, built through decades of relationships, directly impacts longevity and joy. And mental wealth—peace, clarity, purpose—often gets sacrificed in the name of financial optimization. 

For those who’ve diligently saved and planned, the biggest risk may not be running out of money. It may be running out of time to fully live.

Explore how shifting the question from “Can I afford to retire?” to “What am I giving up by staying?” can lead to a more fulfilling path forward.

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The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

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Episode Transcript

Speaker 1 (00:00):
In today's video I'm going to give you five reasons.
It might be time for you toretire right now.
But before I do so, I want tofirst illustrate why it's so
difficult for people to makethis retirement decision in the
first place.
I wrote to a lot of people andI remember specifically a couple
years back I was meeting withan individual who had saved lots
of money for his retirement.
By all measures, by all means,by all objective standards, this
person was in a great positionto retire, but the challenge was

(00:23):
he was in a great position toretire, but the challenge was he
was in a very high-paying job.
He'd worked years and years andyears to get to this point and
every single year he continuedto work.
He had more stock fest, he hadanother bonus that he would
receive, he would pay more intosocial security, he would max
out his 401k and it became verydifficult for this individual to
retire.
And what I started to realizeabout this situation is this

(00:43):
individual, much like many of us, was optimizing for one very
specific type of wealth.
What so often happens is welook at financial planning, we
look at retirement planning andwe think that it's a math
problem, and that math problemsays the more I can optimize,
the more I can improve, the moreI can build my portfolio, my
savings, etc.
The better off I'm going to be.
Now this individual had gottento a point where his financial

(01:05):
wealth, his ability to retire hewas there, but it was very
difficult to pull himself awayfrom work knowing how much he'd
be leaving on the table Everyyear.
Longer he worked, his MonteCarlo probability of success
increased.
His ending portfolio balanceincreased.
His portfolio balance todayincreased.
So why should he walk away?
Well, I'm going to go over thefive reasons I believe this

(01:26):
individual should walk away andas I go through this, I'm going
to walk through this through hisspecific context.
But I think these principlesare relatable to all of us, and
these principles have to do withthe fact that there's different
types of wealth.
We need to look at wealth notjust from the financial side,
but from a truly holisticstandpoint, and the first thing
that I would look at with thisindividual when recommending

(01:46):
that he retire was the conceptof time wealth.
Yes, we can look at financialwealth, and that's what we
always do.
That's your portfolio balance,that's how much you have in cash
, that's your financial position, but time wealth is something
that becomes increasingly moreimportant the older you get.
We all look at Warren Buffettand we say, well, warren
Buffett's a billionaire, look athow wealthy he is.
But there's this concept of atime billionaire.

(02:08):
A time billionaire is anindividual who has at least a
billion seconds of liferemaining.
Now, one billion seconds oflife roughly translates to about
32 years.
So those of you that are maybe60 years old, if we have a life
expectancy of, say, 92, thatmeans you have about a billion
seconds left.
So you take a Warren Buffettwith a net worth of billions and
billions and billions ofdollars.

(02:29):
My guess is he would be willingto trade all of that to get the
time wealth that you haveremaining in your lifetime.
So if all we're looking at isthe financial side of things, if
we're just looking at how canwe optimize the numbers, what
you're going to do is you'regoing to end up at this point
where you have optimizedeverything.
You have a wonderful portfolio,a wonderful net worth, but you
no longer have any time left toenjoy it.

(02:49):
So the concept of time wealthis, yes, you can over optimize
your financial wealth and missout on time.
None of us has any idea howmuch longer we have left, and
time is only non-renewablecurrency.
You can always go back to workif you need to.
You can always earn more moneyif you need to.

(03:10):
Sure, it gets harder to do theolder that you get, but you
always could to some extent ifyou needed to.
Time is something we never knowhow much longer we're going to
have.
So if all we're looking to dois optimize the financial side
of things, then what we're goingto do, even if it's
unintentionally, is we're goingto start to squander our time
wealth.
So how much are we willing totrade off in terms of more
financial wealth in exchange formissing out on that time wealth
?
And don't just think of time interms of how much longer do you
have to live.

(03:30):
Think of it through the lens ofhow many more holiday seasons
do you get to spend with yourparents?
How many more vacations do youget to have with your family
before your kids or yourgrandkids they start getting
married and having families oftheir own, and it gets more and
more difficult to get the wholefamily together to do things.
Time is this very finite,limited resource that, if we're
over-indexing, over-optimizingfor the financial side of things

(03:51):
.
We're not paying enoughattention to time.
If we don't have time, itdoesn't matter how much money we
have, we're not going to beable to enjoy it.
The second reason that thisindividual I think it was time
for them to retire was the senseof health.
Physical wealth Doesn't matterhow much money you have.
If you don't have your health,if you don't have your physical
well-being, you're not going tobe able to enjoy it.

(04:13):
There's this saying that ahealthy person thinks of a
thousand things, a sick personthinks of just one.
So when you're that physicallyhealthy person and you're
optimizing for the financialwealth, don't neglect your
health.
As soon as you lose it, as soonas you become very sick, as soon
as you deteriorate beyond thepoint that you can recover, none
of the financial side is reallygoing to matter.

(04:35):
Sure, some matters of do youhave enough to afford long-term
care?
Do you have enough to fund someof the medical procedures that
you might need?
But beyond that, what good isthat wealth actually doing for
you?
So if all we're doing isfocusing on the financial side
of things, optimizing thefinancial plan, we're missing
out on the reality that ahealthy body is going to be the
thing that enables us toactually enjoy all this, the
thing that actually allows us topursue what we want to pursue,

(04:56):
to spend time with the people wewant to spend time with, to
actually enjoy what we'veaccumulated and what we've grown
on the financial side.
So the second reason I believethat it was time for this
individual to retire was so thathe could prioritize his
physical wealth.
He was in a very high payingjob, but that was taking a toll
on him Long hours, stressfuldeadlines, was not able to
prioritize his health, and if hedid that long enough, he

(05:19):
wouldn't actually be able toultimately enjoy his wealth.
The third reason I believe itwas time for this individual to
retire was to prioritize hissocial wealth, and so I think
you can start to see a themehere.
There's different types ofwealth and, by the way, many of
these principles come from abook called the Five Types of
Wealth.
Check out that book.
I have no relation to it, butit's a wonderful and a powerful
book if you want to properly setthese things in proper

(05:41):
perspective of understandingthat wealth isn't truly just a
financial thing, but it's goingto encompass many different
aspects of your life.
So back to social wealth.
This individual earning a lot ofmoney, continuing to work,
large bonuses, large stockvesting very difficult to walk
away from because all he saw washis financial scorecard was
increasing Every single wholeyear.
He worked longer, he wasgetting better off financially,

(06:02):
but from a social standpoint,you cannot create a best friend
overnight.
You cannot invest in wasincreasing Every single whole
year.
He worked longer, he wasgetting better off financially,
but from a social standpoint,you cannot create a best friend
overnight.
You cannot invest inrelationships and have those
flourish overnight.
What I see too frequently is, bythe time that people retire,
one of the scariest things to dois what am I actually going to
do when I retire?
I don't have the friendships, Idon't have the relationships,
because all of my time was spentworking.

(06:22):
All of my time was spent eithercaring for my family, managing
responsibilities or doing thethings I need to do at work,
which are all very importantthings.
But if we're not investing inrelationships now this includes
family Ideally your firstpriority should be investing in
your family, but what are theother relationships you're
investing in?
Those aren't things that aregoing to blossom and flourish
overnight.
What can you begin doing todayso that you have those strong

(06:47):
social support structures forthe rest of your life.
Many, many, many studieshighlight the importance of your
social well-being.
In fact, one of the largestindicators or predictors of your
overall quality of life andlongevity of life is going to be
the strength of yourrelationships.
So if you don't have those,it's not going to matter how big

(07:08):
your portfolio is if you don'tfeel as if you're in a position
to actually enjoy yourretirement, to have the
happiness that comes from strongsocial relationships.
So this individual is notsimultaneously able to continue
working to optimize financialwealth and also optimize his
social wealth.
Sometimes you can do both.
If you can do both, wonderful.
But if you are in the positionwhere you're like this
individual and you'reover-optimizing for the
financial side and other areasare suffering, it might be time

(07:31):
to retire so you can prioritizewhat really matters.
The fourth reason that it wastime for this individual to
retire was so that he couldprioritize mental wealth, as
I've already mentioned a fewtimes now.
Wonderful compensation,wonderful financial benefits for
continuing to work, but it wastaking a major toll on him
emotionally.
His ability to have a calm mind, his ability to live

(07:51):
stress-free, anxiety-free, wasinhibited by this work.
Sometimes these things aren'tmutually exclusive.
Sometimes you can have a veryhigh-paying job and you can have
a calm mind.
You can have an anxiety-freelifestyle.
In this particular instance,that was not the case.
So for every step he tookforward to optimize his
financial well-being, he wassimultaneously taking a step

(08:12):
backwards in terms of his mentalwell-being.
One of the things that I'lloften say is the sign of a good
financial plan is a lifewell-lived.
A life that's filled withanxiety, a life that's
characterized by constantlybeing on edge, losing sleep, not
feeling your best that's not alife well lived.
So how do we prioritize ourmental well-being, our ability
to pursue the things that lightus up?

(08:33):
Now, a lot of these things areintertwined Our relationships,
our health, our mentalwell-being all of these things
aren't mutually exclusive.
They all support each other.
So what we're looking at hereis what are the things that we
can do to support all of thesethings?
And in many cases, all of thesethings are difficult to do when
working those high stress, highpaying jobs.
Now here's the final reason itwas time for this individual to

(08:54):
retire.
He was in a financial positionto do so.
He already had the financialwealth he was in a position to
where we looked at his goals,what he wanted to do.
He was there.
He could retire today and doall those things.
The trap that he was in was hecould work longer and do even
better.
The trap that he was in was hiswhole life.
He thought about how do I build, how do I grow, how do I save,

(09:16):
how do I optimize?
And he was truly optimizing,but just for the financial side
of things.
So what my guidance to him was,as we look at these five reasons
, wasn't stop optimizing.
It was by optimizing for thefinancial side of things, the
other areas of your life thatare going to be more indicative
of a higher quality of life youare simultaneously letting those
deteriorate.
You're letting those areas slip.

(09:38):
And so when you look at thisholistically, it doesn't matter
how optimized the finances are.
I don't care if your portfoliovalue today doubles or triples
or quadruples.
If that happens, will all theseother areas of your life suffer?
You're not going to be happy,you're not going to have that
life.
Well-lived.
That, I say, characterizes agood financial plan.
Now, this would be dramaticallydifferent if this person was

(09:59):
very undersaved, if they had nomoney.
You have to make the sacrificesto get to that position where
you are financially able toretire.
So all this is under theassumption that you've done what
you need to do, or you're ontrack to do what you need to do
to be financially okay.
But the financial side of thingsshould support the other areas
of your life, should support theother types of wealth that you
should be pursuing.
It should never take the placeof them.

(10:20):
So how can you start to viewlife through this lens of all
these things?
In some regard should be like ascorecard.
When you look at a decision,what's going to be the impact of
that decision on your financialwealth?
You absolutely should look atthat, but don't neglect to also
understand what is the impact ofthat decision going to be on
your mental wealth, yourphysical wealth, your time

(10:41):
wealth, your social wealth.
When you look at all thesethings and again I'm borrowing
these terms directly from thebook the Five Types of Wealth,
it's a great way of framing itwhen you look at every decision
through, how is it going toimpact these things?
You're going to make betterdecisions.
You're going to make decisionsthat don't only optimize the
financial side of things, butthey'll optimize for overall
well-being, for overall qualityof life, so retirement isn't

(11:03):
something that everybody needsto do.
But if you get to the pointwhere you are starting to make
decisions purely for thefinancial side of things and
letting everything else slip,then I would encourage you to
take a look at these fivedifferent types of wealth to
help you understand whatdecisions you should be making
today to prioritize your overallwell-being in the future, their

(11:37):
money.
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