November 10, 2025 • 14 mins
Retirement doesn’t come down to a magic number, it comes down to your number. This episode gives you a simple, personalized framework to decide when you can truly retire based on the life you want, not generic benchmarks.
First, get clear on monthly spending (baseline needs + lifestyle wants). Then reverse-engineer your target by layering in taxes, a sensible withdrawal strategy, guaranteed income (Social Security, pensions), and the one-time costs people forget—like cars, remodels, weddings, or big trips.
Beyond the math, we tackle the emotional side: purpose, identity, and designing days that feel meaningful, so the plan funds a life you actually want to live.
What you’ll learn
- A simple framework to find your number, not “the” number
- How to translate monthly spending into a retirement target
- Coordinating Social Security, pensions, and portfolio withdrawals
- Planning for taxes, RMDs, and estate basics without overwhelm
- Budgeting for big one-time expenses (and avoiding nasty surprises)
- Stress-testing returns and inflation—without getting lost in complexity
- Building purpose and rhythm in the first 1–2 years of retirement
If this brought clarity to your timeline, follow the show, share it with a friend, and leave a quick review—so more people can retire on purpose.
-
Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
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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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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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:00):
Having worked with hundreds of early retirees
one-on-one so that they canretire with confidence, I've
learned the shocking reasonpeople work past 60.
And it's not just, well, youknow, they didn't save enough or
they didn't think about theirpurpose.
Number one, it's health care.
Number two, it's the SocialSecurity timing.
And number three, it's the taxtraps that are associated with
(00:21):
withdrawal strategies.
And that's what I'm going to goover in today's episode.
This is a fun one.
This is going to be jam-packedwith just little hints and tips
and hacks and tricks that I'vegathered from working with
clients that hopefully you allresonate with.
Now, are things constantlychanging?
Yes.
That's why I say I don't dofinancial plans.
I do planning because healthcareis changing and subsidies are
(00:43):
going to be shifted based off ofincome and how you withdraw that
income.
And if you don't have asuperhero account and you're
pulling all your money from a401k, you're going to be paying
way more in taxes because that'staxed as ordinary income versus
capital gains.
So the reason I bring that up,and I'm already getting into it,
because you can tell I get soexcited, is there are people
that want to retire early so badand they feel they're on track,
(01:05):
meaning they feel they've savedenough.
Where if they were technically65, they'd have enough money to
last from 65 to 95, but they're57 or 58 today, and they're
worried I'm going to need to payfor healthcare.
So I feel like I should keepworking to stock some more extra
money away into this superheroaccount, which is going to help
me keep my income low so I caneither get healthcare subsidies
(01:28):
or do Roth conversions or payless on Social Security in terms
of taxes from let's call it 62to 70.
So I see a wide range of peoplethat retire.
And the fun thing for me is Iget to see and learn from these
situations and tell you allabout them.
So my request is if you'rewatching this on YouTube, let me
know what is your plan toretire.
(01:48):
How did you come up with it sothat we can all learn from each
other?
If you're listening on thepodcast app, there is a way to
rate and review the show onApple.
It's a little difficult.
I think you have to scroll downand you will see where you can
leave a star review based offhow you enjoy the show.
And then on Spotify oriHeartRadio, wherever you
listen, you'll see an optionthere.
And if you want to leave yourfeedback and what you're
(02:09):
planning to do for retirement,that helps more people find the
show.
So thank you in advance fordoing that and taking a second.
My goal is to help you allretire early with confidence.
My name is Ari.
I am the chief growth officerhere at Root Financial.
I am a CFP that stands forcertified financial planner.
And I love helping people, justlike you, make sure that when
you're retiring, you don't havethat little thing in the back of
(02:30):
your head going, Oh, is theresomething I missed?
Should I work one more year?
Or why didn't I do thoseconversions?
Or you're always talking aboutthis cauliflower stuff.
Do I need to be eating that?
So I have all these littlesimple analogies and examples
that I like to share because itwhat I find helps people
actually relax and go, okay,once I get a plan, I'm in a good
spot.
So the way I like to start theseepisodes oftentimes are with
(02:52):
little stories.
And the one I'm going to usetoday is a true story with me
and a soccer injury I had.
And I'm going to connect thedots here.
So when I play soccer, I'm overthe moon.
That is my flow state.
When I get injured, I am not funto be around.
I am hangry.
Worse than hungry and angry.
Put together, I am hangry.
Now, I am not fun to be aroundwhen I'm hangry.
That's what she says.
(03:13):
So she says, all right, you needto go get an MRI.
So I go get an MRI, and you'rethinking I'm going to be
miserable because I'm going tosee the, oh my gosh, am I hurt?
How long am I out for?
I'm actually at peace.
I now have the severity of myinjury.
That's like your financial plan.
You're going to see, got it.
This is what I'm on track for.
Whether I like it or not, thisis the truth.
Then I get to see my physicaltherapy.
I can see, got it.
(03:33):
So I'm going to need to do thisprocedure, then I'm going to
have to do this PT, then I'mgoing to be back on the field.
Once I have my plan, I'mactually pretty calm.
At this point, I'm not thinkingwhat's the worst case scenario,
what's going to happen.
I've got a plan.
So I know that plan's going tochange because if I'm doing
well, I could get on the fieldsooner, and vice versa.
Same thing for you guys.
You need to know, oh my gosh,are you on track to retire right
(03:55):
now?
Like, imagine you went and ranan analysis and you saw that
based off what you want to spendand when you know you want to
retire, that it was actuallydoable.
I mean, think about what itwould be like going to work
every day.
You'd be like, oh my gosh, thisis way easier.
I'm going to work and like I'mon track, like, versus what can
feel like a pipe dream at times.
So hopefully you guys resonatewith that.
(04:17):
And if you're going to work now,after listening to this, running
your plan, going, wow, it doesfeel different.
Let us know because this is whathelps inspire us all to keep
adding money to our own 401ks,myself included.
I want to be working as long asI enjoy what I do.
And that's the cool thing aboutgetting to run a business with
my partner James and all theamazing team members here at
Root, is our job is to make sureour clients have an awesome
(04:39):
experience and that our currentemployees that are internal love
their jobs, that they keepwanting to work here and
therefore service clients betterand have career opportunities,
and we all win.
So I am taking my work veryseriously, not because I have
to, but because I I want to.
My life is better by doing that.
And at the same time, I want tosave and invest for my future.
(05:00):
What if all of a sudden all ofour clients turn out to be
terrible and which would neverhappen, but pretend they're all
super mean to me for whateverreason and my employees are
saying, hey, we don't respectthe work you do.
Well, I wouldn't feel veryfulfilled.
I would ask myself, what am Idoing wrong?
But then I would go, okay, letme look into what I need to do
here.
And what if it got so toxic?
I want to have the financialfreedom to do what I want to do.
(05:22):
So I'm in the same spot as allof you.
So let's go into some of theseexamples here.
So health insurance, retiringbefore 65 means you're paying
for health care.
Okay.
Now it can be a significantcost, but it's not enough to
scare you away.
I have clients that spend a fewhundred bucks a month and I have
clients that spend$30,000 a yearin health care.
So I don't want you to hear thatand go$30,000 a year, how on
(05:42):
earth am I going to pay for thatfrom$60 to$65?
Like, where am I going tomagically come up with$180,000 a
year?
That's not what I'm expecting.
I'm expecting you to go, okay,let me look at the reality.
How am I going to withdrawincome in retirement?
And if you see you have theoption to do it in an effective
manner and keep a subsidy in areasonable state where maybe
(06:04):
you're paying$300 a month.
So yeah, that's significant.
Maybe it's$3,600 for you andyour spouse.
So now you're at$7,200.
Is that doable?
You might find it helps a lot towork two more years so that
you're in a spot to do that.
You might find you need toinstead of maxing out your$401K,
you just want to get the companymatch and defer the rest into a
savings account so that you haveenough money to travel the first
(06:26):
year of retirement because youhaven't set enough money aside
for that.
Or you want to do a home remodelor you still have kids in
college.
These are things that you needto make sure you're planning
for.
Because if not, healthcare canbe one thing that can derail
your early retirement.
But when I say derail, it's notlike you won't be okay.
Most of you, if you're planningwell and you retire, it's not
like you're not going to eat.
(06:46):
It's more of you're going tolook back and go, well, I can't
really go out to eat and geteverything I want.
Or I can't travel and if I wantto stay longer, extend my trip
because that wasn't in thebudget.
You don't want to be thinkinglike that.
It's just not fun, trust me.
So that's number one is planaround healthcare.
I have tons of videos andpodcasts where I go into great
detail on that.
But it's surprising becauseI'll, I'll, you know, I used to
(07:06):
think someone come to me, I go,look, you're on track for
retirement.
And it looks like from 65 to 95,you're great.
Like, what's the holdup?
And they're like, well, nomatter what you say, no matter
how many times you say it, itfeels weird.
I have kids in college.
And what if they want to go tograd school?
Like, am I going to pay forthat?
And I'll say, Do you want to?
And they'll say, Yeah, I wantto.
I go, okay, well, let's add thatin.
(07:26):
I'll say, what about uh helpingthem with a wedding?
And they'll say, Well, I neverhad help.
And I'll say, okay, so do youwant to help them?
They go, yeah, because that'ssomething I didn't have.
I go, great, let's layer thatin.
We keep layering in things.
Home remodels.
Are we going to downsize?
Downsizing is a big one.
I'll see people who go, Yeah, Ikind of want to plan for it.
I go, well, that's tricky.
And they go, why?
I said, are you going to planfor it or not?
(07:46):
Because if you plan for it asif, yeah, we're going to
downsize, and that's going toreally help our plan.
And then all of a sudden, you'relike, we don't want to downsize
because emotionally we love thishome and it's where our kids
grow up and they just told methey never want me to sell, but
you already retired.
Well, if we didn't seriouslyplan around that, and I had
assumed you were going to dothat, you might have to go back
(08:06):
to work, which we don't want youto have to do.
So a large reason people workpast 60 is not just financial in
terms of do we have enoughmoney?
It's okay, well, we're in a goodspot, but we could be in a way
better spot if I worked one moreyear, or if I work six more
months.
And that's what I often hear isoh, why don't I just we call
that goalposting, moving thegoalposts back.
(08:27):
Yeah, one more project, one moreyear, two more years.
In fact, I hear that so often.
What I'm gonna do, I'm gonnaclose my eyes, I'm gonna ask you
to do it with me.
Unless you're driving, don't getin trouble.
Don't make me get in trouble,don't sue me.
Okay, don't crash.
But if you are thinking, justlike I'm thinking, yes, have I
pushed the goalpost back?
Let me know in the comments.
In the comments, say, you knowwhat?
I just went and asked my spouse,and they said I've done it 10
(08:48):
times.
I just thought I did it once, oryou know, I kind of known I've
always been pushing it back oneyear, but it's not financial.
I just don't really know whatthe heck I'm gonna do.
And that's scary.
My partner James has a greatquote.
He says, When's the last timeyou've done something for the
first time?
And I think about that a lot.
I'm like, well, I just gotmarried for the first time, and
hopefully the last time.
Before that, I guess I graduatedcollege or I passed the CFP.
(09:11):
Like these are things that comeinto my mind.
So it's worth thinking about.
Okay, when's the last timeyou've done something truly for
the first time?
And when's the last time you'venot had income hit your bank
account?
Like, that's a scary thought.
Now it's coming from youraccount.
So that's number one.
Number two, Social Securitytiming and pressure around that
timing.
Oh, I hear this all the time.
Here's most of you, ready?
(09:31):
Most of you are like, yeah, Iknow I should retire at some
point.
I don't know when, but SocialSecurity, I paid into it for so
long.
I know it looks at my 35 highestyears of earnings.
I've worked that long.
I'm gonna turn it on at 62because I don't want to look
back and if Social Security getscut, wonder why didn't I turn it
on earlier and you know collectas much as I can?
But then there's another part ofyou that's like, well, what if I
(09:51):
do live till like 95 and itturns out I, you know, pass
away?
I want my spouse to make surethey get the largest amount.
And if they were at home withthe kids or just didn't have as
much of an earnings record,you're gonna regret if you turn
it on and you get$2,500 a monthwhen if you would have waited to
get$4,000,$4,000 is what theywould receive for the rest of
their life.
So there's that sense of, okay,yeah, I I know maybe I'm, you
(10:14):
know, let's call it 59 yearsold.
I know I could retire at 60, butit really is gonna help bridge
the gap because I don't have aton in the portfolio and 162
hits, I'm turning on SocialSecurity.
So I'm just gonna work one moreyear.
So you can see how we keepcoming back to that theme of
goalposting.
So if that resonates, let meknow in the comments because
these are things that I hearfrom my clients.
And if you guys don't chatbelow, I just am doing a weird
(10:37):
TED talk here right now.
So that's number two.
If I don't want to hear numberthree, all these tax traps.
Oh, what do I call the taxwindow?
The tax window is the time fromwhen you retire until Social
Security turns on until RMDsbegin.
So pretend you retire at 60 andyou turn on Social Security at
67, and RMDs, required minimumdistributions, begin at 75.
(10:59):
We've got a seven-year windowhere where we've got to do those
Roth conversions.
When would we do Rothconversions?
And what is Roth conversion?
Well, that's called eatingcauliflower.
You're paying a little bit oftaxes to avoid eating a lot of
taxes, or paying a lot,obviously, in the future, which
is what happens at that RMD age.
That's when you're forced totake out 3.8% as a starting spot
(11:20):
from your portfolio that ispre-taxed.
So some of you are like, bigdeal.
I've got like 200,000 in my IRA.
That might not be something yougot to deal with.
Other people are like, well, ifI have 2 million and that grows
to three and then 4 and then 5,I'm gonna have to take out 3.8%.
That's a significant amount ontop of Social Security, on top
of inheritance.
Like, am I gonna get taxed atlike 40, 50% on like millions of
(11:43):
dollars?
Yeah, sometimes that's the case.
So what do we do about it?
From 60 to 67 until SocialSecurity gets turned on, that's
where your income can bemanipulated as you see fit.
We can decide to turn on a levelof income when we do a
conversion that increases yourincome.
So if you retire at 61, well,we've got six years to do really
good conversions.
(12:03):
Because once Social Security ison, maybe that's 40,000, 50,000
bucks that's now helping us outon the portfolio side where it's
not fully up to your portfolioto create income for you.
But now that's 50,000 as astarting spot for Social
Security.
So in terms of income, yourmodified adjusted gross income.
So now we don't have as muchroom in terms of tax brackets to
(12:23):
do conversions at the bestpossible brackets.
Meaning if we have no income,theoretically, we could go do
Roth conversions and pay taxesat 10%, 12%, how great would
that be?
But if Social Security is comingin, we're already in the 12%
bracket.
So maybe if we do a conversion,we're gonna have to pay at 22 or
24 or 32.
So what we want to do is bereally effective with how we
(12:44):
withdraw income.
So I find a lot of people areretiring after 60 because they
go, wow, I didn't even knowabout this tax window thing.
I just thought if I keptworking, it would be better.
In a weird way, the earlier youretire, the more of a tax window
you have, the more opportunityto do more of these conversions
or harvesting.
Now, don't just go retire forthe tax window.
(13:05):
Make sure you're in acomfortable financial position
where you know it's gonna help,but it's not driving that.
You don't want the tax tail towag the life dog.
So hopefully, some some cooltips and tricks from today's
episode.
If it resonated, please let meknow.
I love getting to do this.
And then finally, this is whatwe specialize in here at Roost.
If you want to work with a teamthat loves this stuff, the tax
(13:26):
planning, the estate, thehealthcare, the withdrawal, the
Roth, the insurance, this iswhat we love.
And we want to help you.
So you can reach out to us atrootfinancial.com.
See you guys next time.
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.
(13:47):
I've not missed a single week inyears, and that is because I
love getting to do this.
Now, please be smart about thisbefore you actually execute any
strategy that you see me talkabout or hear me talk about,
should I say, please talk toyour financial advisor, your tax
preparer, your estate attorney.
Please be smart about this.
None of this should be construedas financial advice.
(14:08):
This is for fun, educational,informational purposes only.
Once again, just quickdisclaimer here, guys, please be
smart about this.
Appreciate you listening asalways.
And you can, of course, submit aquestion on my website, early
retirementpodcast.com.
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
(14:30):
single person.
And if I find it will be helpfulfor a lot of people, I will
absolutely make an episode onit.
At the very least, give you someinsight.
That's it.
Thanks, guys.
Having worked with hundreds of early retirees
one-on-one so that they canretire with confidence, I've
learned the shocking reasonpeople work past 60.
And it's not just, well, youknow, they didn't save enough or
they didn't think about theirpurpose.
Number one, it's health care.
Number two, it's the SocialSecurity timing.
And number three, it's the taxtraps that are associated with
(00:21):
withdrawal strategies.
And that's what I'm going to goover in today's episode.
This is a fun one.
This is going to be jam-packedwith just little hints and tips
and hacks and tricks that I'vegathered from working with
clients that hopefully you allresonate with.
Now, are things constantlychanging?
Yes.
That's why I say I don't dofinancial plans.
I do planning because healthcareis changing and subsidies are
(00:43):
going to be shifted based off ofincome and how you withdraw that
income.
And if you don't have asuperhero account and you're
pulling all your money from a401k, you're going to be paying
way more in taxes because that'staxed as ordinary income versus
capital gains.
So the reason I bring that up,and I'm already getting into it,
because you can tell I get soexcited, is there are people
that want to retire early so badand they feel they're on track,
(01:05):
meaning they feel they've savedenough.
Where if they were technically65, they'd have enough money to
last from 65 to 95, but they're57 or 58 today, and they're
worried I'm going to need to payfor healthcare.
So I feel like I should keepworking to stock some more extra
money away into this superheroaccount, which is going to help
me keep my income low so I caneither get healthcare subsidies
(01:28):
or do Roth conversions or payless on Social Security in terms
of taxes from let's call it 62to 70.
So I see a wide range of peoplethat retire.
And the fun thing for me is Iget to see and learn from these
situations and tell you allabout them.
So my request is if you'rewatching this on YouTube, let me
know what is your plan toretire.
(01:48):
How did you come up with it sothat we can all learn from each
other?
If you're listening on thepodcast app, there is a way to
rate and review the show onApple.
It's a little difficult.
I think you have to scroll downand you will see where you can
leave a star review based offhow you enjoy the show.
And then on Spotify oriHeartRadio, wherever you
listen, you'll see an optionthere.
And if you want to leave yourfeedback and what you're
(02:09):
planning to do for retirement,that helps more people find the
show.
So thank you in advance fordoing that and taking a second.
My goal is to help you allretire early with confidence.
My name is Ari.
I am the chief growth officerhere at Root Financial.
I am a CFP that stands forcertified financial planner.
And I love helping people, justlike you, make sure that when
you're retiring, you don't havethat little thing in the back of
(02:30):
your head going, Oh, is theresomething I missed?
Should I work one more year?
Or why didn't I do thoseconversions?
Or you're always talking aboutthis cauliflower stuff.
Do I need to be eating that?
So I have all these littlesimple analogies and examples
that I like to share because itwhat I find helps people
actually relax and go, okay,once I get a plan, I'm in a good
spot.
So the way I like to start theseepisodes oftentimes are with
(02:52):
little stories.
And the one I'm going to usetoday is a true story with me
and a soccer injury I had.
And I'm going to connect thedots here.
So when I play soccer, I'm overthe moon.
That is my flow state.
When I get injured, I am not funto be around.
I am hangry.
Worse than hungry and angry.
Put together, I am hangry.
Now, I am not fun to be aroundwhen I'm hangry.
That's what she says.
(03:13):
So she says, all right, you needto go get an MRI.
So I go get an MRI, and you'rethinking I'm going to be
miserable because I'm going tosee the, oh my gosh, am I hurt?
How long am I out for?
I'm actually at peace.
I now have the severity of myinjury.
That's like your financial plan.
You're going to see, got it.
This is what I'm on track for.
Whether I like it or not, thisis the truth.
Then I get to see my physicaltherapy.
I can see, got it.
(03:33):
So I'm going to need to do thisprocedure, then I'm going to
have to do this PT, then I'mgoing to be back on the field.
Once I have my plan, I'mactually pretty calm.
At this point, I'm not thinkingwhat's the worst case scenario,
what's going to happen.
I've got a plan.
So I know that plan's going tochange because if I'm doing
well, I could get on the fieldsooner, and vice versa.
Same thing for you guys.
You need to know, oh my gosh,are you on track to retire right
(03:55):
now?
Like, imagine you went and ranan analysis and you saw that
based off what you want to spendand when you know you want to
retire, that it was actuallydoable.
I mean, think about what itwould be like going to work
every day.
You'd be like, oh my gosh, thisis way easier.
I'm going to work and like I'mon track, like, versus what can
feel like a pipe dream at times.
So hopefully you guys resonatewith that.
(04:17):
And if you're going to work now,after listening to this, running
your plan, going, wow, it doesfeel different.
Let us know because this is whathelps inspire us all to keep
adding money to our own 401ks,myself included.
I want to be working as long asI enjoy what I do.
And that's the cool thing aboutgetting to run a business with
my partner James and all theamazing team members here at
Root, is our job is to make sureour clients have an awesome
(04:39):
experience and that our currentemployees that are internal love
their jobs, that they keepwanting to work here and
therefore service clients betterand have career opportunities,
and we all win.
So I am taking my work veryseriously, not because I have
to, but because I I want to.
My life is better by doing that.
And at the same time, I want tosave and invest for my future.
(05:00):
What if all of a sudden all ofour clients turn out to be
terrible and which would neverhappen, but pretend they're all
super mean to me for whateverreason and my employees are
saying, hey, we don't respectthe work you do.
Well, I wouldn't feel veryfulfilled.
I would ask myself, what am Idoing wrong?
But then I would go, okay, letme look into what I need to do
here.
And what if it got so toxic?
I want to have the financialfreedom to do what I want to do.
(05:22):
So I'm in the same spot as allof you.
So let's go into some of theseexamples here.
So health insurance, retiringbefore 65 means you're paying
for health care.
Okay.
Now it can be a significantcost, but it's not enough to
scare you away.
I have clients that spend a fewhundred bucks a month and I have
clients that spend$30,000 a yearin health care.
So I don't want you to hear thatand go$30,000 a year, how on
(05:42):
earth am I going to pay for thatfrom$60 to$65?
Like, where am I going tomagically come up with$180,000 a
year?
That's not what I'm expecting.
I'm expecting you to go, okay,let me look at the reality.
How am I going to withdrawincome in retirement?
And if you see you have theoption to do it in an effective
manner and keep a subsidy in areasonable state where maybe
(06:04):
you're paying$300 a month.
So yeah, that's significant.
Maybe it's$3,600 for you andyour spouse.
So now you're at$7,200.
Is that doable?
You might find it helps a lot towork two more years so that
you're in a spot to do that.
You might find you need toinstead of maxing out your$401K,
you just want to get the companymatch and defer the rest into a
savings account so that you haveenough money to travel the first
(06:26):
year of retirement because youhaven't set enough money aside
for that.
Or you want to do a home remodelor you still have kids in
college.
These are things that you needto make sure you're planning
for.
Because if not, healthcare canbe one thing that can derail
your early retirement.
But when I say derail, it's notlike you won't be okay.
Most of you, if you're planningwell and you retire, it's not
like you're not going to eat.
(06:46):
It's more of you're going tolook back and go, well, I can't
really go out to eat and geteverything I want.
Or I can't travel and if I wantto stay longer, extend my trip
because that wasn't in thebudget.
You don't want to be thinkinglike that.
It's just not fun, trust me.
So that's number one is planaround healthcare.
I have tons of videos andpodcasts where I go into great
detail on that.
But it's surprising becauseI'll, I'll, you know, I used to
(07:06):
think someone come to me, I go,look, you're on track for
retirement.
And it looks like from 65 to 95,you're great.
Like, what's the holdup?
And they're like, well, nomatter what you say, no matter
how many times you say it, itfeels weird.
I have kids in college.
And what if they want to go tograd school?
Like, am I going to pay forthat?
And I'll say, Do you want to?
And they'll say, Yeah, I wantto.
I go, okay, well, let's add thatin.
(07:26):
I'll say, what about uh helpingthem with a wedding?
And they'll say, Well, I neverhad help.
And I'll say, okay, so do youwant to help them?
They go, yeah, because that'ssomething I didn't have.
I go, great, let's layer thatin.
We keep layering in things.
Home remodels.
Are we going to downsize?
Downsizing is a big one.
I'll see people who go, Yeah, Ikind of want to plan for it.
I go, well, that's tricky.
And they go, why?
I said, are you going to planfor it or not?
(07:46):
Because if you plan for it asif, yeah, we're going to
downsize, and that's going toreally help our plan.
And then all of a sudden, you'relike, we don't want to downsize
because emotionally we love thishome and it's where our kids
grow up and they just told methey never want me to sell, but
you already retired.
Well, if we didn't seriouslyplan around that, and I had
assumed you were going to dothat, you might have to go back
(08:06):
to work, which we don't want youto have to do.
So a large reason people workpast 60 is not just financial in
terms of do we have enoughmoney?
It's okay, well, we're in a goodspot, but we could be in a way
better spot if I worked one moreyear, or if I work six more
months.
And that's what I often hear isoh, why don't I just we call
that goalposting, moving thegoalposts back.
(08:27):
Yeah, one more project, one moreyear, two more years.
In fact, I hear that so often.
What I'm gonna do, I'm gonnaclose my eyes, I'm gonna ask you
to do it with me.
Unless you're driving, don't getin trouble.
Don't make me get in trouble,don't sue me.
Okay, don't crash.
But if you are thinking, justlike I'm thinking, yes, have I
pushed the goalpost back?
Let me know in the comments.
In the comments, say, you knowwhat?
I just went and asked my spouse,and they said I've done it 10
(08:48):
times.
I just thought I did it once, oryou know, I kind of known I've
always been pushing it back oneyear, but it's not financial.
I just don't really know whatthe heck I'm gonna do.
And that's scary.
My partner James has a greatquote.
He says, When's the last timeyou've done something for the
first time?
And I think about that a lot.
I'm like, well, I just gotmarried for the first time, and
hopefully the last time.
Before that, I guess I graduatedcollege or I passed the CFP.
(09:11):
Like these are things that comeinto my mind.
So it's worth thinking about.
Okay, when's the last timeyou've done something truly for
the first time?
And when's the last time you'venot had income hit your bank
account?
Like, that's a scary thought.
Now it's coming from youraccount.
So that's number one.
Number two, Social Securitytiming and pressure around that
timing.
Oh, I hear this all the time.
Here's most of you, ready?
(09:31):
Most of you are like, yeah, Iknow I should retire at some
point.
I don't know when, but SocialSecurity, I paid into it for so
long.
I know it looks at my 35 highestyears of earnings.
I've worked that long.
I'm gonna turn it on at 62because I don't want to look
back and if Social Security getscut, wonder why didn't I turn it
on earlier and you know collectas much as I can?
But then there's another part ofyou that's like, well, what if I
(09:51):
do live till like 95 and itturns out I, you know, pass
away?
I want my spouse to make surethey get the largest amount.
And if they were at home withthe kids or just didn't have as
much of an earnings record,you're gonna regret if you turn
it on and you get$2,500 a monthwhen if you would have waited to
get$4,000,$4,000 is what theywould receive for the rest of
their life.
So there's that sense of, okay,yeah, I I know maybe I'm, you
(10:14):
know, let's call it 59 yearsold.
I know I could retire at 60, butit really is gonna help bridge
the gap because I don't have aton in the portfolio and 162
hits, I'm turning on SocialSecurity.
So I'm just gonna work one moreyear.
So you can see how we keepcoming back to that theme of
goalposting.
So if that resonates, let meknow in the comments because
these are things that I hearfrom my clients.
And if you guys don't chatbelow, I just am doing a weird
(10:37):
TED talk here right now.
So that's number two.
If I don't want to hear numberthree, all these tax traps.
Oh, what do I call the taxwindow?
The tax window is the time fromwhen you retire until Social
Security turns on until RMDsbegin.
So pretend you retire at 60 andyou turn on Social Security at
67, and RMDs, required minimumdistributions, begin at 75.
(10:59):
We've got a seven-year windowhere where we've got to do those
Roth conversions.
When would we do Rothconversions?
And what is Roth conversion?
Well, that's called eatingcauliflower.
You're paying a little bit oftaxes to avoid eating a lot of
taxes, or paying a lot,obviously, in the future, which
is what happens at that RMD age.
That's when you're forced totake out 3.8% as a starting spot
(11:20):
from your portfolio that ispre-taxed.
So some of you are like, bigdeal.
I've got like 200,000 in my IRA.
That might not be something yougot to deal with.
Other people are like, well, ifI have 2 million and that grows
to three and then 4 and then 5,I'm gonna have to take out 3.8%.
That's a significant amount ontop of Social Security, on top
of inheritance.
Like, am I gonna get taxed atlike 40, 50% on like millions of
(11:43):
dollars?
Yeah, sometimes that's the case.
So what do we do about it?
From 60 to 67 until SocialSecurity gets turned on, that's
where your income can bemanipulated as you see fit.
We can decide to turn on a levelof income when we do a
conversion that increases yourincome.
So if you retire at 61, well,we've got six years to do really
good conversions.
(12:03):
Because once Social Security ison, maybe that's 40,000, 50,000
bucks that's now helping us outon the portfolio side where it's
not fully up to your portfolioto create income for you.
But now that's 50,000 as astarting spot for Social
Security.
So in terms of income, yourmodified adjusted gross income.
So now we don't have as muchroom in terms of tax brackets to
(12:23):
do conversions at the bestpossible brackets.
Meaning if we have no income,theoretically, we could go do
Roth conversions and pay taxesat 10%, 12%, how great would
that be?
But if Social Security is comingin, we're already in the 12%
bracket.
So maybe if we do a conversion,we're gonna have to pay at 22 or
24 or 32.
So what we want to do is bereally effective with how we
(12:44):
withdraw income.
So I find a lot of people areretiring after 60 because they
go, wow, I didn't even knowabout this tax window thing.
I just thought if I keptworking, it would be better.
In a weird way, the earlier youretire, the more of a tax window
you have, the more opportunityto do more of these conversions
or harvesting.
Now, don't just go retire forthe tax window.
(13:05):
Make sure you're in acomfortable financial position
where you know it's gonna help,but it's not driving that.
You don't want the tax tail towag the life dog.
So hopefully, some some cooltips and tricks from today's
episode.
If it resonated, please let meknow.
I love getting to do this.
And then finally, this is whatwe specialize in here at Roost.
If you want to work with a teamthat loves this stuff, the tax
(13:26):
planning, the estate, thehealthcare, the withdrawal, the
Roth, the insurance, this iswhat we love.
And we want to help you.
So you can reach out to us atrootfinancial.com.
See you guys next time.
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.
(13:47):
I've not missed a single week inyears, and that is because I
love getting to do this.
Now, please be smart about thisbefore you actually execute any
strategy that you see me talkabout or hear me talk about,
should I say, please talk toyour financial advisor, your tax
preparer, your estate attorney.
Please be smart about this.
None of this should be construedas financial advice.
(14:08):
This is for fun, educational,informational purposes only.
Once again, just quickdisclaimer here, guys, please be
smart about this.
Appreciate you listening asalways.
And you can, of course, submit aquestion on my website, early
retirementpodcast.com.
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
(14:30):
single person.
And if I find it will be helpfulfor a lot of people, I will
absolutely make an episode onit.
At the very least, give you someinsight.
That's it.
Thanks, guys.
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