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May 12, 2025 14 mins

Even when the financial plan indicates you're on track, many people experience anxiety—especially between ages 50 and 65, before traditional retirement benefits begin. This episode explores ways to prepare for that critical transition with clarity and confidence.

• One of the most impactful retirement risks is withdrawing too much from your portfolio in the early years
• Many individuals are “qualified rich, cash limited” with the majority of assets in tax-advantaged retirement accounts
• Building a taxable brokerage account can provide additional flexibility before age-based access to retirement funds
• For some, temporarily adjusting retirement account contributions may help support short-term liquidity needs (consider your specific situation and consult a financial professional)
• Planning ahead for early retirement expenses—such as travel, healthcare, or home projects—can reduce surprises
• Avoiding large discretionary expenses early in retirement may help reduce stress on your portfolio
• Focus on what you can control: spending, timing of retirement, asset allocation, and strategic withdrawals



Advisory services are offered through Root Financial, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship. The Early Retirement Academy is an educational resource offered by Root Financial. Participation may involve a fee. Use of the tool does not establish a client relationship or constitute personalized advice. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements. 


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Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.


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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
You can be on track for retirement and still feel
worried.
And here's why I bet that youare right now on track for
retirement from, let's call it,65 to 95.
But you're wondering, hey, whatif something goes wrong?
Markets go down, I want tospend more than I think,
healthcare costs go up, my kidsdon't get a scholarship to go

(00:20):
play football in college,whatever.
Well, now all of a sudden, yeah, I think my retirement's okay,
but it's this 50 to 65.
That's kind of given me theanxiety, because what if it
turns out I retire one year tooearly?
Or what if it turns out onceagain, markets go down,
healthcare goes up, I livelonger than I think.
So the point here is, mostpeople are worrying about this

(00:43):
gap from 50 to 65 because that'swhen, all of a sudden, they go.
Well, after 65, if I reallyneeded to, I mean I could turn
on social security.
I'm probably going to spendless when I'm in my 70s and 80s
on travel versus my early yearsof retirement.
And I'll say that's correct.
And they'll say, well, thenhelp me out.
Like, what do I do in thissituation?

(01:04):
And what we do is we do a lotof what if?
Scenarios that I'm going toexplain today.
But the biggest thing and I'mgoing to this is the number one
takeaway which you're going tohave right now is don't put
everything on your portfolio inthe first year.
And so here's what I mean.
I will see people who reach outand they go look, I have 2

(01:25):
million bucks.
I feel that I want to spendabout 60, $70,000 a year in
retirement.
I've done some basic math.
I think I can do that.
But my concern is right now Ihave extra healthcare costs
because I don't have Medicareyet.
I want to travel more when Ihave my health.
My kids are not in college yet,so I'm going to need to cash
flow that we really do need anew car and we need to remodel

(01:53):
the bathroom.
So the risk here is markets godown and they get unlucky In the
one year when they retire.
Now, all of a sudden, they needlet's call it $200,000, but
their $2 million is not at $2million anymore.
Now it's at $1.8.
Well, they still need that200,000.
So now, all of a sudden,they're at 1.6 and they need
income for the next 40, 50 years.

(02:13):
So the point here is you can belegitimately on track for
retirement and still haveanxiety about hey, can I really
retire early?
So that's number one isvalidating the way you feel
right now, because some peopledon't know why they feel this
way.
They're like I feel like I haveenough.
I mean, I've got a million anda half, I've got two million,
I've got three, five, 10 millionbucks.
Why is it?
I still have this feeling thatsomething is missing.

(02:40):
And the way you protect againstthat is by running enough what
if?
Scenarios to understand yourprobability of success.
Now, if you were to ever gohave a surgery and they say
there's 100% chance that you'llbe okay, they're lying to you.
Something could always go wrong.
Now maybe it's 99.99% chance,but the reality is you'll
probably be fine.
I've had multiple surgeries.
I'm grateful they exist becausemy life is better.
But the point here is I can'tguarantee anything and

(03:02):
retirement is about confidence.
And if you knew right now, if Isaid hey, ari, hypothetically,
right now, I know you want toretire early at 55.
I know I look 55.
So that's why I'm saying this Iwant to retire early at 55.
And if markets were to go down30% and I live till I'm 100 and
my legacy goal is to leave 2million to each of my future

(03:24):
children.
I can still do that, but you'regoing to have to live with this
amount of volatility.
I would be able to say, well, Icould live with that.
I could today.
But me at 55 might say I don'twant that level of volatility.
So I have an option I can spendless, I can work longer, I can
change my allocation.
But the big ones is how much Iwant to spend and how long I

(03:44):
want to work.
Those are the two things reallyin your control.
Yes, it's in your control.
Your allocation, how muchequities or fixed income you
have yes, it's in your controlto the degree of course you
travel.
That goes back to spending.
But the big things that are outof your control, look, you
can't control how markets aregoing to perform.
I don't believe in markettiming.
I do like companies likeVanguard and Dimensional and

(04:07):
Fidelity that they're not tryingto pick and beat the stock
market.
It's.
You've done a good job savingand investing.
You now need income for therest of your life.
So it's really 50 to 65 thatwill dictate the quality of your
retirement.
So what do I encourage you to do?
If you're still working todayand you've got a few years until
you actually retire.

(04:28):
I encourage you, can you?
Maybe it makes sense totemporarily halt some of your
401k contributions.
If you find that your 401k isin a comfortable position, maybe
it makes sense for you to starttackling some of these things,
like a new car or a remodel orcollege savings or a travel fund

(04:50):
, before you retire.
So if you retire and markets dogo down because you get unlucky
, it's not like your portfoliohas this gigantic pressure of oh
my gosh, we have to be able toafford all of these things all
at once, because if it's time topay for college, you're not
going to tell your kid nocollege for you.
Sorry, markets are down.
No, they're going to go tocollege and if we don't have

(05:12):
enough cash on the side, that'sa problem.
You're probably not going towant to push back travel in
retirement.
I see people willing to travelless meaning hey, we're going to
take 60,000 worth of big tripsand now it's 40,000 worth.
I'll see that, but I don't wantyou to have to do that.
I want you to be able to.
You worked really hard 30, 40years, I imagine to save and
invest so you could retire earlyone day.

(05:32):
Maybe you sold a company, maybesomething else happened that's
allowing you to be in thisposition of even talking about
an early retirement, which which, by the way, is success in its
own Just even the fact that youare right now listening, trying
to put yourself in a position tolegitimately not have to work
ever again doesn't mean you haveto stop working.
But if you knew you didn't haveto keep working, you would feel

(05:53):
different.
You'd have less stress.
You'd maybe take on lessprojects, knowing, hey, if they
were to say you're out of here,okay, well, financially I'm fine
, you will put less pressure onyourself, and so kudos to you
for listening to this, trying toget yourself in a good spot.
So this is the number one thing.
Once again, it's can we avoidputting everything into one year
?
So this is why I harp onsomething called the superhero

(06:15):
account, the taxable account,the brokerage account, the joint
account, the individual account, the after-tax account it's all
called the same exact thingsuperhero account.
Now, if you call Vanguard andsay I want to open a superhero
account, they're going to bevery confused.
Okay, it's not a real name, butthat's what I like to call it.
So this brokerage account thisis where a lot of people will

(06:35):
find wait a second.
I have a million bucks in my401k and I'm going to retire in
three years.
Maybe it makes sense for me todrop my contribution from doing
the max to just getting theemployer match and then putting
the rest of that money into myfuture travel fund or my home
remodel fund or my new car fundand it's getting really

(06:57):
intentional.
Now maybe it doesn't make sensefor you because you're in such
a high tax bracket.
Getting that 401k deductionreally is helping your tax
situation and money's reallytight, so it doesn't mean it's
for you.
But if you're like, hey, I haveextra every month, I'm in my
highest earnings years right nowI'm bringing in 200, 300,
500,000 a year.

(07:17):
I've got extra money.
What's the most optimal thing?
Well, it's not always maxingout your 401k.
That's a common mistake If youalready have a lot of money in
there.
I call it qualified rich, cashpoor.
My parents they are house rich,cash poor, beautiful home in
Malibu, california.
They it's house rich, cash poor.

(07:38):
That's not throwing off income.
They don't want to leave.
If they were renting it out,different story.
So they're working in their 70sbecause they like their job and
they are big spenders now.
Luckily, they like what they do.
So they're still working.
But if it was up to them, theywould not work to the extent
that they're currently working,and this is in large part
because they receive poorfinancial advice.
Thus why I became a financialadvisor.

(07:58):
So that's's house rich, cashpoor.
I just said qualified rich,cash poor.
That's where you have so muchmoney in qualified assets like a
401k and you want to retire at54.
Good luck.
You have to pay the penalty.
Now there's certain things youcan do.
There's something called asubstantially equal periodic
payment, sep.
There's something called a ruleof 55, which I have different

(08:18):
episodes explaining.
So if truly all your money isin a 401k and you're thinking,
is there any way I can use thismoney, tap into it to start
retiring early?
Yes, but those are not theoptimal options.
It's better if you have abrokerage account.
So this is the number one thingCan you have a brokerage
account and get that to a reallyhealthy position?

(08:39):
At the same time, can you startthinking about yeah, we're
probably going to want to buy anew car and do a remodel.
So can you limit the number ofbig expenses in the early years
of retirement?
Because what happens is if youspend too much too quickly and
markets go down.
Now, yeah, you'll be okay from60, 65 to 100, but you won't be
spending to the same degree andnow you don't have income that's

(08:59):
coming from any other sourceother than you, which is
stressful.
So my biggest tip this is ashorter episode, but once again
biggest tip superhero account.
Try to at least think aboutadding money to and it can be a
high yield savings account.
It can be a balanced portfolio.
It doesn't need to go superaggressive, but have something
that you can start socking awayinto travel fund, college fund,

(09:22):
car fund.
I wouldn't do a legacy fundbecause and even long term care
I would say that's going to do adeeper analysis on things like
that but health care beforeMedicare, make sure that you're
optimizing that, which a lot ofpeople don't do as well.
But just quick tips, real quick.
Well, but just quick tips, realquick.

(09:43):
Those are the things that, whenit comes to why most people are
worried about a retirement, mostpeople are always thinking the
biggest risk is the stock marketor the biggest risk is what if
it turns out I live longer?
Those are two big risks.
That's not the biggest.
The biggest risk to an earlyretirement is you get unlucky,
which is out of your control,and so we're trying to limit
what is once again in ourcontrol so that we can go wow, I

(10:07):
have taken care of what Ireally need, whether it be,
let's assume, home remodel,travel, wedding, whatever.
And now you retire and all you,because once again you have
these other things saved for.
Now you're like I just needportfolio to give me my 7,000 a
month or my 8,000 a month thismonth, because that's my

(10:28):
traditional living and that's it, because you already understood
that you have money saved,because you were aware of that
and saved ahead of time.
The other thing to think aboutis think about are there things
that aren't necessary that year?
Now, sometimes, if your carbreaks down, you need a new car
and don't drive around in anunsafe vehicle.
But certain things can bepushed back, like a home remodel

(10:51):
or downsizing, a wedding notalways easy to really push back,
college not really easy to pushback.
So there are certain thingsthat truly are out of your
control.
So my only ask from this is youget really intentional Now.
You don't need to do this.
If you're like 10 years out fromretirement, you don't other
than the superhero account?
Yes, I would do that.
But the other things like, hey,thinking about kids' weddings,

(11:14):
look, you're not going to beable to plan out to the nth
degree, what year is that goingto be?
And if you know, that'sprobably five years plus away we
want that money growing.
So I'd put it in a superheroaccount and I would make sure
it's growing.
But don't hyperanalyze to thepoint of well, I didn't look at
every single degree, so I can'tretire early.
Don't do that.
That's you cheating yourself.
What I would encourage you todo if you are more than five

(11:35):
years out from retirement,enroll in the Early Retirement
Academy, which you can see inthe description.
That is an actual software toolthat you can use to see when you
are on track to retire.
I mean, you will know instantlyand you'll be like, okay,
here's the different variables.
What if I spend more?
What if I get unlucky?
What if, yada, yada?
And that should give youconfidence.
You might go, wow, I'm furtherout than I thought and this is
good for me to see.

(11:55):
I need to increase my savingsor I need to decrease my
spending.
You might find, hey, I'm in abetter spot than I thought.
Maybe I can retire earlier.
What am I worrying about?
So I use that as a tool.
It's not a recommendation interms of it's not going to be
like, hey, here's how muchexactly you should be um saving
to exactly meet your goals.

(12:16):
It's not, it's not thinking,it's just software that you can
put your numbers into.
Now you do have me as yourguide and there are custom
videos to help along the way.
So I find a lot of people find,hey, this is really helpful.
And then, once I'm actuallyretired early, now I want root,
the company I work at, to helpactually make sure all these
goals accomplish, getaccomplished in the correct

(12:36):
manner, because I don't want anew job as an advisor in
retirement.
That's what I hear a lot of.
So that's it.
If you want to work with Root,of course please look in the
description of this episode.
If you want access to the EarlyRetirement Academy, you can
check that out as well.
And then I encourage you ifyou're like, hey, this is
interesting stuff.
I like hearing about taxstrategy and healthcare and
withdrawal and these differenttopics, I invite you to

(12:57):
subscribe.
I love getting to do this.
So please do.
If you enjoy it, like it andshare it with someone you want
to retire early with.
That's it, thanks guys.
Thank you all, as always, forlistening to the early
retirement podcast.
I love getting to host theseshows and make different content
for you guys every single week.
I've not missed a single weekin years and that is because I
love getting to do this.

(13:18):
Now, please be smart about this.
Before you actually execute anystrategy that you see me talk
about or hear me talk about,should I say Please talk to your
financial advisor, your taxpreparer, your estate attorney?
Please be smart about this.
None of this should be construedas financial advice.
This is for fun, educational,informational purposes only.

(13:38):
Once again, just a quickdisclaimer here.
Guys, please be smart aboutthis.
Appreciate you listening, asalways, and you can, of course,
submit a question on my website,earlyretirementpodcastcom, if
you, of course, want me toaddress a specific case study or
topic.
I will not promise I can get toit, but I respond to every
single person and if I find itwill be helpful for a lot of

(14:00):
people, I will absolutely makean episode on it, at the very
least give you some insight.
That's it, thanks guys.
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