The Real Reason Most People Struggle in Retirement (It’s Not Money)

Retirement planning is often framed as a numbers game where you can get lost in focusing on maximizing your 401(k), minimizing taxes, and chasing investment returns. But financial security alone doesn’t guarantee fulfillment. The bigger challenge many retirees face is psychological, not financial.

The transition from decades of work into retirement often sparks an identity crisis. A career provides structure, purpose, and community—when it’s gone, retirees can feel adrift. Without clarity on what truly matters, it’s easy to copy someone else’s blueprint for retirement and end up feeling unfulfilled.

As Morgan Housel points out, without a clear definition of happiness, people mimic those who appear successful. We can o measure success in houses, cars, or vacations. Yet those measures don’t guarantee joy. The key is asking the right questions: Which relationships matter most? What brings genuine purpose? How do you want an ordinary Tuesday morning to look?

One revealing exercise highlights these priorities: imagine receiving $25,000 that must be spent in a week. The choices made often uncover what really matters and form the foundation for a retirement vision that feels authentic.

When that vision is clear, financial strategies can support your goals, whether you dream of world travel or your ideal life routine at home.

Retirement isn’t just an ending; it’s the start of a more authentic chapter.

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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.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Episode Transcript

Speaker 1 (00:00):
Most people watching this video think retirement is
all about the numbers.
How much have you saved?
Can your portfolio withstandthe next downturn?
Do you have the right taxstrategy in place?
And while all those things areimportant, if that's all you're
focused on, you're really goingto struggle when it actually
comes time to retire.
But here's the truth that noone actually talks about.
The number one reason peoplestruggle in retirement actually

(00:20):
has nothing to do with money,and while money can be a
supporting factor here, thenumber one reason people
struggle is they don't actuallyknow what they want their life
to look like.
And if you don't actually knowwhat you want your life to look
like, then no amount of moneydoesn't matter what your
financial strategy is.
Nothing can replace that interms of giving you the type of
retirement that you're lookingto live.
In one of his blog posts, morganHousel had this to say.

(00:42):
He said if you have no strongviews on what kind of life you
want to live, who you are, whatyou desire, what makes you happy
and what doesn't, you're likelyto want to mimic the most
visually appealing person youcome across, which is often the
person with the biggest house,fastest car or nicest clothes.
That may work, it may not.
We see this all the time.
We have goals for retirement.

(01:02):
We know that by a certain agewe should retire.
We know we should max out our401k, we know what to do to
optimize social security.
And then we get there and wefreeze.
And we freeze because we thinkwhat am I actually going to do?
The past 30 years, the past 40years, all I've been doing is
working and grinding and raisinga family and doing all these
things that matter, but I'velost the sense of who I am and
what I want to do.
So when I set goals for myretirement, it's not actually my

(01:29):
goals.
I don't even know what my goalsare.
I'm just going to mimic what Isee other people doing.
They must be happy, right.
They have the nice cars, theytake the nice trips, they do the
things that seem to make themhappy.
Maybe that's what I want for myretirement.
But if that's the way thatyou're approaching it, you're
going to be let down.
You're going to retire.
You might enjoy it for a short,brief period of time, but then
you're going to feel this senseof loss.
Why?
Because your job was youridentity.

(01:49):
Your job was your structure.
Your job was your socialconnection.
Your job was this thing that,even if you didn't absolutely
love it, provided these thingsthat all of us need, provided
this purpose that gave you thissense of identity.
And then one day, just likethat, all that changes.
You now have the money, youknow how, the time you've
retired from that, but what haveyou retired into?

(02:09):
And that's what I want toaddress today.
How do you avoid that scenariowhere, even if you have the best
financial strategy in the world, you may have a very tough
retirement if you don't addressthese questions first?
So what do you do?
Well, if it's not about lookingat other people's homes, other
people's golf trips, otherpeople's idea of what a good
retirement looks like for them,what should you be doing?
What you do is you start withclarity, not money.

(02:32):
So here's a relatively simpleframework for that.
Instead of thinking, what do Iwant to do with my retirement?
That's an enormous questionthat's going to cause a lot of
anxiety just thinking about that.
Think about what do you wanteach of these components or each
section of your life to looklike?
What would you want yourrelationships to look like?
Who are you spending time with?
Who's most important to you.
Think about that.
What about your health?
What does that look like?

(02:54):
What about hobbies?
What about faith?
What about travel?
What about giving back?
What about all these thingsDoesn't have to be super
complicated, but if you canidentify these are the things
that actually matter most to me.
Not what my neighbor's doing,not what my old coworker's doing
, but these things bring me joy.
These things bring me a senseof purpose.

(03:16):
Write down one or two, maybethree things for each of those
and then simply say how can Iprioritize that?
Imagine you're retired today andit's a Tuesday morning, not a
weekend, not an extravagant trip, it's a Tuesday morning.
What are you doing with each ofthose things?
You don't have to do all ofthem in one day, but what can
you do to prioritize yourrelationships, purpose, hobbies,
adventure, whatever that mightbe?
Sit with that and think aboutit.
For as much time as we spend onthe financial side of things,

(03:39):
can you spend just a little bitof time with this?
Who are you and what do youwant to do?
If you want a fun thoughtexercise that goes along with
this, let's explore this.
You get $25,000 in your bankaccount today under one
condition you have to have spentit within the next seven days.
Anything you spend, it getstaken back.
And spending does not meansaving it or investing or even

(04:00):
paying down debt.
Spending it means what are thethings you would actually spend
that money on.
What comes to mind.
It's a good exercise to gothrough to help you understand
what do you actually care aboutNot just indefinitely saving
something for the future, butwhat would you spend money on
today if you were forced tospend it because it would be
taken back if you didn't.
Then once you have some of thosethings in place, then you can
plan backwards.
If your idea of a wonderfulretirement is four luxury

(04:22):
vacations a year all across theworld, that's gonna be a very
different financial strategythan someone who also wants to
take a lot of trips, but theiridea of a fun trip is driving to
the mountains for a longweekend and spending that hiking
and backpacking.
So what matters to you?
Don't just say travel what typeof travel?
Don't just say relationshipswhat would you be doing?

(04:43):
What types of relationships?
Don't just say hobbies whatspecific hobbies?
Because once you have thatclarity, once you know what your
life is going to look like,then you can design the
financial strategies to supportthat.
A financial plan without acorresponding life plan is
somewhat meaningless.
At the end of the day, it's notgoing to matter how much you
have in your 401k when youcollect social security, how

(05:04):
much you save in taxes to theright withdrawal strategy, if
you don't have a bigger purposethat it's connected to, you're
not going to have the impactfultype of retirement that you
should have.
So if you're struggling withthis, reach out to us.
This is exactly what we do hereat Root Financial Not just a
financial piece, but helping toconnect that financial piece,
helping to be a thought partner,a thought leader with you to
say what can life look like?

(05:24):
What does this look like if Iget out of the rut that I've
been in for the past 30, 40years which, by the way, it's
not a bad thing.
That's just life.
Life sometimes takes us on thisjourney of over the course of
our careers, we do less and lessof what we think we want to do
and we look back one day and sayI'm 55, I'm 60, I'm 65.
And those things I used to enjoyI don't do any of it anymore.

(05:45):
I've been so focused on careerand responsibilities and
preparing that I've lost sightof that.
How can you get to this pointwhere you start to have a vision
for what retirement can looklike and then take the necessary
steps financially to move inthat direction?
But here's the bottom lineRetirement should not be the end
of your story.
Retirement should be the verybeginning.
Retirement can be scary, it canbe overwhelming, because you

(06:08):
have to think of those biggerquestions.
What will you actually do whenyou have the time, the resources
, the freedom to be whatever youwant to be?
But if you can go through theseexercises, if you can start to
think about what actuallymatters most, think about what
that practically looks like on aTuesday morning in retirement,
on a Thursday afternoon inretirement, and then work
backwards to say what financialmoves should I make today to

(06:30):
move in that direction, that isgoing to make all the difference
.