April 3, 2025 • 22 mins
Many professionals find that retiring isn’t just about having enough money—it’s about feeling ready to leave behind the structure, identity, and comfort of a career.
In this Root Financial podcast episode, James and Ari explore the emotional hurdles of retiring from a high-paying, high-stress job, even when financially prepared. They highlight the value of aligning retirement with your future self’s goals and priorities, not just your current fears.
Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here
Timestamps:
0:00 - A comment from the Collective
3:03 - A first-day-of-school analogy
4:25 - What would my future self do?
6:47 - Helpful feedback
8:32 - Make sure you're ready financially
10:20 - A life you don't retire from
13:18 - The opportunity cost
16:39 - More words of wisdom
18:44 - Making the decision is the scary part
Create Your Custom Strategy ⬇️
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:02):
This is another episode of Ready for Retirement.
I'm your host, james Canole,and I'm here to teach you how to
get the most out of life withyour money.
And now on to the episode.
All right, you and I knowthere's a big difference between
being financially ready toretire and actually being ready
to retire, which of courseextends beyond just financial,
and that's what we're going totalk about today.
(00:23):
We actually have a comment fromsomeone in the Root Collective
which is asking that exactquestion of look, I've run the
numbers, I'm ready to go, I haveenough, but I can't bring
myself to not just leave my job,but leave my high stress job
that also happens to be veryhigh paying.
And this is a predicament wesee time and time and time again
(00:44):
of we work all our livesthinking that as soon as we have
enough money, we're going tocall it quits.
We finally get there and itbecomes very difficult to
actually pull the trigger andcall it quits.
Will you read for us thequestion?
Not the question, but thecomment that's in the Root
Collective.
Speaker 2 (01:00):
I will.
And for those who do not knowwhat the Root Collective is, it
is our free community, so youcan go join this and see exactly
what we're looking at under thetab that we call the what I
Wish I Knew Earlier and thiscomes from DT Lyons, who says
taking the big leap.
Curious to hear from othersthat have stepped away from high
stress, high paying career andretired early but continue to
(01:22):
work doing something they'repassionate about at the fraction
of the salary.
I'm in that situation.
My analysis says I can do it,but it's hard to take the leap.
Speaker 1 (01:32):
We see this a lot and , as I just alluded to the
reasons why is it's not just amath problem, it's not just a
spreadsheet problem.
There's a lot that goes beyondthat.
So I'm curious are you see thatquestion?
You see that comment?
We've got some really goodcomments, people responding to
that from the collective, whichwe're also going to point out.
Where does your mind go first?
Speaker 2 (01:52):
Yeah, my mind first goes to.
It would be really weird if youwere to be like, oh my gosh, I
can retire, I have no worries,no political concerns, no
economic concerns.
I know exactly what I'm goingto do in retirement.
That would actually concern meas an advisor, cause I'd be like
look, how could you really know?
You haven't done it yet.
So you can ask friends and youcan kind of see on some online
(02:13):
forums, even like this rootcollective, and see what people
say.
But there's always going to beprobably some piece of you that
goes look, how could I reallyknow?
Like this whole concept ofretirement, having income for 40
or maybe 50 plus years, it'sweird.
It's like you're living offthis portfolio.
For so long You've been addingmoney to your 401k and now all
(02:35):
of a sudden you're supposed topull from it.
It's like no, no, no, I'm nevergoing to pull from it, I just
add money to it.
So I would start by saying thebig leap.
It's always going to be a leap,but how do you make it?
So when you jump in the waternot a perfect analogy, but you
jump in the water it's not thiscrazy splash where now all of a
sudden it's oh my God, who canyou hang out with and how much
(02:55):
income could you really support?
And it's more of a perfect divewhere you're in and you're like
, yep, I'm in the water.
I was more comfortable out ofthe water because I wasn't even
wet out of the water, but Ireally know I do want to go
swimming.
So it's first starting withthat.
Hey, it's going to be a leap.
How do we do it appropriately?
Speaker 1 (03:15):
Yeah, Tomorrow morning, my wife and I, we are
dropping off our daughter forher first day of preschool and
she's going to be I don't knowif nervous is the right word.
She just doesn't know what itis yet, but it's going to be
difficult.
I'm nervous, ashton's nervous.
This is a big change and Ibring that up because she's not
retiring, she's literallystarting preschool.
(03:36):
I think what we forget is thisis a very normal thing.
Your first day of school maybeyou remember, maybe you don't
Was that scary?
Probably Are you glad you tookthe leap and went to your first
day of school, maybe not beingcoerced into it by parents.
First day of high school Wasthat scary?
(03:56):
Probably so.
First day of college Was thatscary?
First day with a real grown upjob Was that scary?
Was that scary?
First day with a real grownupjob was that scary?
First time you asked out yourmaybe now spouse was that scary?
Ask him to marry you was thatscary?
Starting a family all of thesethings are scary and I think we
forget that because sometimesnot always, but sometimes by the
(04:17):
time that we're 60, 65, 70,like in those retirement years,
we haven't done one of those newthings in quite some time.
We're in that position where,like this commenter, say, hey,
I'm in a high paying job, whichprobably means you've hit your
stride, you've been there for awhile and you haven't.
Maybe you're not rememberingwhat it was like to be in that
job for the first time.
And so I think that one thingthat we have to do.
(04:39):
I always think like this.
Some people might think this ismorbid, but I always think
through.
I always think like this.
Some people might think this ismorbid, but I always think
through I'm going to die one day.
Am I going to be, if I have theopportunity.
When that happens, if I'mlooking back on my life and if
I'm this individual, am I goingto be looking back at myself,
kicking myself for retiringbecause I could have stayed in
that high stress job and I couldhave put more money in my
(05:00):
portfolio, which means, as I amgoing to my grave, I probably
could have had more money thatI'm going to die with.
Or am I going to be kickingmyself because I'm saying, look,
you stayed in that high stressjob too long.
It literally took years off yourlife, not just these extra
years of working that you can nolonger do the things that you
wanted to do, but the years ofyour health, that it took off
(05:21):
because your blood pressure wasout of control, because you
couldn't go to the gym, becauseyou couldn't eat healthy,
because you couldn't prioritizephysical health, mental health,
spiritual health, friendshiphealth, all those things.
Because of that, I don't know,but my guess is going to be it's
the latter.
So sometimes we have to askourselves the question of not,
what would I do in thissituation?
(05:43):
What will my future self do?
There is some study and I haveno idea where it's from so I'm
not going to try to cite itcorrectly.
But when psychologists look atour decision-making frameworks,
one of the reasons peopleprocrastinate which I think this
enlarged person may beprocrastination is our brains
(06:06):
literally think of ourselveslike James right now.
When James has somethingimportant that he doesn't want
to do in front of him and says,oh, I'll do it later, it's
because my mind is registeringfuture James as a completely
different individual, so it'salmost saying that person is
going to do it.
I'm not because it'suncomfortable for me to have to
do, but the problem is thatnever changes.
It's always that person, thatperson, that person meaning
(06:28):
later, later, later.
And if we could disconnect fromthat and try to think, no, that
both of those are me.
Both of them like at some pointwe need to make that decision,
is now the time to do it.
At some point we need to makethat decision, is now the time
to do it, and a lot of times thething that helps me is thinking
through the version of 85 yearold James, 95 year old James,
sitting there, hopefully inthose later years, being able to
(06:50):
reflect on a life and sayingwhat would I have been glad I
did?
And then trying, as best aspossible, to make the decision
that future me would have made.
So that's my thought.
Now we have some other goodcomments, I think in here to
this Username is Detroit Lions,dt Lions.
What are some other pieces offeedback this individual
(07:10):
received that stood out to you?
Speaker 2 (07:12):
So, first of all, you're not going to pass away
for much, much later, and I canonly imagine how you're feeling
right now with your daughterstarting tomorrow.
But my first thought is is shestarting tomorrow?
And there was no prep?
Was it just hey, you're goingto show up?
She doesn't even know whereshe's going.
Like, probably not You're.
You're probably told her, hey,you're, you're going to be
around other kids.
(07:32):
You might even know some ofthese kids that there's probably
some preparation that'soccurred that will make that
leap a little easier.
Now to your point, james.
Here we are giving analogiesabout your daughter jumping in a
pool.
It's not likely, as applicableto a lot of you who are going
hey, this sounds great, but youguys really aren't hearing me.
(07:53):
I'm about to retire, what do Ido?
And so here's the cool partabout this collective.
You get to hear from peoplelike Tommy C, who says the
following, and there's a littlelonger, but there's a few things
I want to read in here, so I'mnot going to read all of it, but
here's someone who says I tookthis leap 11 months ago, at age
56, and thought I would need tofind something part-time just to
(08:13):
keep my engineering by mindbusy.
Honestly, I haven't even missedwork.
Omg, the reduction of stressand the increase of time is so
liberating.
His guidance to once again,this Detroit Lions, this big
football fan, says here's what Iwould do.
I'd set up a plan to payyourself on the same schedule as
your current paycheck.
(08:34):
It'll feel like vacation planto keep yourself engaged with
your field and then go back ifyou want to, but you probably
won't want to.
And then the third one is justdo it.
And my only issue with this asa financial advisor where I want
to bring your thoughts in here,james is I love the idea of
just do it.
Nike's a cool brand.
I get why they started, just doit.
(08:54):
But it's really hard to do itif financially, you don't know
you're going to be okay.
And so, yeah, we're alwaysgoing to make sure people are
dreaming and think aboutretirement, because the worst
thing is you retire early and go.
Yep, I did it, I was over it.
Work was high stress, highpaying, but now you can't really
live your retirement.
Now you're retiring on eggs andtop ramen and that's probably
not ideal for most of you.
(09:15):
So, yeah, I like just do it,but the financial brain is going
.
I got to make sure you know youwon't run out of money.
Speaker 1 (09:23):
And I think this is a very important thing to
highlight.
Most people should not just doit.
Most people would do hey, thisis awesome, I loved retirement
for six months and then I ranout of money and it sucked.
I had to go back and that was.
That was me.
So we are making a bigassumption.
And not even a big assumption.
The reason we're jumping rightinto this is because username
Detroit lion says in mysituation, my analysis says I
(09:44):
can do it.
So he's run the numbers, runthe projections.
I don't know to what degree Iwant to double check those.
I'm going to see that.
But there there is this thingthat we've observed.
Another version of I'm going tocall it procrastination is.
I worked with clients beforewhere it's hey, you're in a
position to retire, awesome, andit's cool.
Let's run one more analysis, soone more analysis, so one more
analysis, and it becomes thisform of distraction, because
(10:07):
it's easier to address that, toaddress the thing that we know,
which is the financial side.
Way easier to do that than tosay what do I actually want to
do when I'm retired?
Who am I going to become?
What's life going to look like?
And I think that that's whystep one has to be are you
financially ready?
If you're not financially ready, do not just do it.
Work the hours you need to work, save the amount you need to
(10:28):
save.
Like, those things are not justthings.
You can leapfrog and go rightto the enjoyment phase.
But I think the point that wewant to make, though, is I don't
think I mentioned this enough,or reinforce this enough is I
actually think that a perfectlife is one that you don't
really retire from.
In some ways, like a perfectworld is you have a job that you
love and it fills you with somuch purpose and enjoyment and
fun that you can keep doing thatfor the rest of your life, or
(10:51):
at least until health no longerpermits.
Unfortunately, a lot of people,especially in high stress
corporate jobs, you just don'thave that freedom.
You can't make it somethingthat you want.
You have to pay your dues, youhave to trade your time for
money so you can invest thatmoney the right way and
ultimately live the things thatyou want to live.
But that's not to say retireinto nothing and saying, okay,
(11:11):
let's get away from that thingthat was high stress and
preventing you from the lifethat you wanted to live.
And now let's create that lifethat you do want to live and in
many cases, like some version ofwork whether or not it's for
money should be part of it.
Work can be something as simpleas everything from.
I know some people that verysuccessful careers and they're
now working at Trader Joe's,just because it creates this
structure and the sense ofcommunity and it's a fun
(11:33):
environment.
You know a lot of people thatgo work down at the golf shop.
I know a lot of people thatwork and they volunteer with the
local parks and rec becausethey want to just be part of
that and that's important tothem.
So keep doing something.
But to your point, ari, makesure the financials are in order
First.
We have plenty of podcastswhere we discuss how can you
tell if you're actually in aposition to retire?
(11:53):
We are just making theassumption or we're taking that
face value.
Making the assumption or we'retaking at face value Detroit
Lions comment, where he saysthat he is in a position to do
so, but it's hard to take thatleap.
Speaker 2 (12:03):
Yeah, james, check out to see if there's other
comments that you might want tobring up here, because I'm
curious and I'll tell everyone.
It's going to be a little toughlove for all of you.
And the reason I'm bringingthis up is I'm going to ask you
not to lie to yourself.
And it's going to be hardbecause some of you are going to
go.
You know what?
Yeah, I'm going to do apart-time job and it's going to
cover my healthcare costs.
(12:23):
And you're really still in thatmindset of, hey, I'm taking this
role because financially, Ineed it to do this or that.
Now, if you're taking a rolebecause financially you just
think, wow, this is going to addmore bonus money where I can
enter more pickleballtournaments and just show my
neighbors how much better I am,then I'm cool with that.
(12:44):
But if you're taking a role togo, you know what I really think
financially, I need to keepworking.
So I'm going to, and I don'treally love it, but it's for the
health care benefit and youknow, without that I'd have to
go pay 800 bucks a month on themarketplace.
I don't want to do that.
(13:05):
Well, it starts with that andthen it becomes okay, what next?
And what I'll see is people go.
Yeah, well, I have thispart-time job, but now I'm not
going to buy appetizers, becauseI was making 200,000 a year
before and now I make like30,000 a year and it just
doesn't feel right because Ijust I don't think I have it in
me.
And then the real problem isyou're 80 and you go.
I don't really think I need a$10 million and thinking about
kind of that morbid of, hey, I'mnot going to be here forever.
(13:26):
It's also the reality.
So are there other commentsthat you're seeing in there,
james, that resonate?
Speaker 1 (13:31):
Yeah, there's a few and I think, before I go, ari,
you do a good job of using thisexample.
A lot is to go back to DetroitLions comment of hey, it's hard
Like I should keep just um,working and saving and investing
.
Let's play that out.
If the goal is to keepimproving the financial
situation, why not always, neverretire, never stop saving,
(13:54):
fully, delay Social Security,cut out all the extra
discretionary spending on funstuff, cut out all the giving
that you do, cut out all, justkeep.
And obviously we hear that andsay, okay, that's absurd, and
obviously that's absurd.
And you can also be extreme inthe other direction, which is
why not just retire at the ageof 24, right after you started
your career?
Well, neither are good options,but it's about finding that
(14:17):
right point where you know thatyou're leaving on the table.
If you haven't invested in RSUs, I'm in that boat, but I've
decided enough is enough, enjoyyour retirement.
Here's another comment I want totouch upon, but that what he's
(14:37):
essentially saying.
Look, it's so hard when you sayhere's the opportunity cost.
The opportunity cost is there'smoney, a carrot that's dangled
in front of you that all youhave to do is stay employed till
a certain date and it's yoursand that is very true.
And that's very difficultbecause money is so tangible,
it's so quantifiable.
You know exactly what you'releaving on the table.
(14:57):
The reframe we'll try toencourage people with is there
is absolutely an opportunitycost to leaving money on the
table, and that's apparent, youknow it, and it's painful.
The thing that you don't see,the thing that's not apparent,
the thing that's just notobvious, is the opportunity cost
of continuing to work.
What's that year of healthworth to you?
(15:18):
What's that year of travelworth to you?
What's that year of adventureworth to you?
And, by the way, there's not aright or wrong answer.
In some cases it is the betteroption to work one more year to
get that extra bonus, more RSUsvesting, more contributions to
your 401k.
That is the necessary and wiseanswer sometimes, but other
(15:38):
times it's not.
And you have to be able to sayit's not just a one-sided
equation.
If it was just one side andjust about the money, never stop
doing this.
But when you realize it is abalance and there are other
things you need to consider,there is a very real trade-off
there.
It's just we don't see it.
And what makes us see it isthis comments that we get all
the time already on channels, onpodcasts and whatever it is, is
(15:59):
hey, I saved and saved andsaved, I finally retired.
I had all these dreams.
My wife and I were going to dothis and then she passed away a
year into retirement.
And it's like how much does thatperson wish they could go back
in time.
If that person could talk toDetroit Lions right now the
username for those of you tuningin late like what would they
(16:19):
say?
How much is money worth?
It becomes the thing thatdrives all of our decisions
until and this is why I thinkabout, like, wait, your future
self.
What are they going to think Atthat point?
Money is not a top 10 factoranymore.
So it just comes by looking atthis from all different angles,
all different sides, to say, yes, money is important.
We never want to discount that,but so too is the life that you
(16:41):
want to live and the thingsthat you want to do.
And what's the cost ofsacrificing those things just
for more money?
Speaker 2 (16:50):
And at some point, it's just no longer worth it.
Yeah, you always say that thesign of a good financial plan is
a life well-lived, and I knowthere's more comments that you
saw in there.
Were there any others youwanted to?
Speaker 1 (16:59):
reference.
Andy Wang had another one.
I won't read the whole thing,but he just talks about his
experience.
He says these podcasts from Ariand James have been helpful,
along with reading Die With Zero.
So that's a great book that Ijust like to recommend to people
to read.
Of this concept of what is moneyreally, how do we translate
that into its true value, whichin large part, is helping us to
(17:20):
have the experiences and do thethings that we want to do.
So, just for someone that's onthat edge and looking for that
sense of I don't want to saythat push, because we shouldn't
be looking for a push if we'renot financially ready yet, but
if we are financially ready weneed that push.
First and foremost, join theroot collective.
It's free.
There's a link in the shownotes here.
Go check it out.
Lots of great things you cantake away there.
But then that books a greatperspective, along with just
(17:43):
trying to put yourself in theshoes of your future self,
because your future self isgoing to have a more objective,
a more disconnected perspectiveon this than you will in the
moment.
Speaker 2 (17:53):
And by no means do James or I go.
Yeah, so everyone's going tolisten to this and just feel the
comfort to go to their firstday of school or to go retire.
That's not what we're expecting, but to join this collective
and see what other people sayand it's completely free, by the
way.
Just go hear from others.
You might take some ideas andyou might even feel that you
learn things you otherwisedidn't know.
(18:14):
There are people who are in thecollective talking about hey,
this feels really weird, butlike I think I'm in a spot to
retire, but like my neighbor, Iknow they have way more money
than me, in a way bigger houseand like I heard them talking
about working till 65.
And so now I'm thinking like,did I just miss something
entirely?
Because I don't think I'manywhere close to retiring, but
I also know that, like ourvalues are different.
(18:35):
And then someone else was inhere saying, oh my gosh, I felt
the same thing and I evenstarted working extra because I
thought I had to and you don't.
It's all custom based off thelife you want to live.
So certainly check out thatcommunity called the Root
Collective and you'll see it inthe description of this episode.
Anything else for today, james.
Speaker 1 (18:56):
I don't think so.
I think that that's a verynormal feeling to have.
As much as we say, do it asmuch as we say.
Here's the perspective.
It's going to be scary Anexample.
So when I started Root, someoneleft this comment that I liked.
Let me see if I can go to it.
Evan commented my job steppedaway from me a year ago so I
retired early.
You know somewhattongue-in-cheek, just saying,
(19:16):
look, I got terminated.
I know so many stories of peoplelike, hey, I got released from
my final job.
That was the best thing thatcould ever happen.
Like the boats were burned forme.
I didn't have to make thedecision.
I know when I started Root,that was the same thing it was.
I got let go from my previousjob and it's like, hey, the
boats are burned, go.
And it's like, oh my gosh, howscary was that.
Well, it was less scary becausesomeone else made the decision
(19:38):
for me.
It's the decision.
That's the scary part in manycases.
And once you make it and don'tmake it ill-informed, don't make
it if you're not prepared, butonce you make it, there's so
many good things on the otherside and one of the things we
try to help people do is how doyou live better lives?
Well, one way that you do thatis you get out of this high
stress job, no matter how highpaying it is, assuming you're a
good financial spot and youstart living, and it starts with
(20:01):
that decision.
So join the collective, reachout to root.
Speaker 2 (20:05):
If you need an advisor to help you do so, root
financialcom click see if youyour fit, but lots of great
resources out there to help withthat.
I, along with others, am sograteful that that boat burned,
which brought you to join andcreate Root and allow us to have
this community.
So to that one boat I'mgrateful.
Speaker 1 (20:22):
Awesome, I love it.
Well, thanks, ari.
Anything else you want to addhere?
That's it All right.
Thanks everyone, and we willsee you next time.
See ya, that's it All right,thanks everyone, and we will see
you next time.
See ya.
The information presented isfor educational purposes only
and is not intended as an offeror solicitation for the sale or
purchase of any specificsecurities, investments or
investment strategies.
Investments involve risk andare not guaranteed.
(20:44):
Any mention of rates of returnare historical and illustrative
in nature and are not aguarantee of future returns.
Past performance does notguarantee future performance.
Speaker 2 (20:52):
Viewers are encouraged to seek advice from a
qualified tax, legal orinvestment advisor professional
to determine whether anyinformation presented may be
suitable for their specificsituation.
Speaker 1 (21:03):
Hey everyone, it's me again for the disclaimer.
Please be smart about this.
Before doing anything, pleasebe sure to consult with your tax
planner or financial planner.
Nothing in this podcast shouldbe construed as investment, tax,
legal or other financial advice.
It is for informationalpurposes only.
Thank you for listening toanother episode of the Ready for
Retirement podcast.
(21:23):
If you want to see how RootFinancial can help you implement
the techniques I discussed inthis podcast, then go to
rootfinancialpartnerscom andclick start here, where you can
schedule a call with one of ouradvisors.
We work with clients all overthe country and we love the
opportunity to speak with youabout your goals and how we
might be able to help.
And please remember, nothing wediscuss in this podcast is
intended to serve as advice.
(21:44):
You should always consult afinancial, legal or tax
professional who's familiar withyour unique circumstances
before making any financialdecisions.
This is another episode of Ready for Retirement.
I'm your host, james Canole,and I'm here to teach you how to
get the most out of life withyour money.
And now on to the episode.
All right, you and I knowthere's a big difference between
being financially ready toretire and actually being ready
to retire, which of courseextends beyond just financial,
and that's what we're going totalk about today.
(00:23):
We actually have a comment fromsomeone in the Root Collective
which is asking that exactquestion of look, I've run the
numbers, I'm ready to go, I haveenough, but I can't bring
myself to not just leave my job,but leave my high stress job
that also happens to be veryhigh paying.
And this is a predicament wesee time and time and time again
(00:44):
of we work all our livesthinking that as soon as we have
enough money, we're going tocall it quits.
We finally get there and itbecomes very difficult to
actually pull the trigger andcall it quits.
Will you read for us thequestion?
Not the question, but thecomment that's in the Root
Collective.
Speaker 2 (01:00):
I will.
And for those who do not knowwhat the Root Collective is, it
is our free community, so youcan go join this and see exactly
what we're looking at under thetab that we call the what I
Wish I Knew Earlier and thiscomes from DT Lyons, who says
taking the big leap.
Curious to hear from othersthat have stepped away from high
stress, high paying career andretired early but continue to
(01:22):
work doing something they'repassionate about at the fraction
of the salary.
I'm in that situation.
My analysis says I can do it,but it's hard to take the leap.
Speaker 1 (01:32):
We see this a lot and , as I just alluded to the
reasons why is it's not just amath problem, it's not just a
spreadsheet problem.
There's a lot that goes beyondthat.
So I'm curious are you see thatquestion?
You see that comment?
We've got some really goodcomments, people responding to
that from the collective, whichwe're also going to point out.
Where does your mind go first?
Speaker 2 (01:52):
Yeah, my mind first goes to.
It would be really weird if youwere to be like, oh my gosh, I
can retire, I have no worries,no political concerns, no
economic concerns.
I know exactly what I'm goingto do in retirement.
That would actually concern meas an advisor, cause I'd be like
look, how could you really know?
You haven't done it yet.
So you can ask friends and youcan kind of see on some online
(02:13):
forums, even like this rootcollective, and see what people
say.
But there's always going to beprobably some piece of you that
goes look, how could I reallyknow?
Like this whole concept ofretirement, having income for 40
or maybe 50 plus years, it'sweird.
It's like you're living offthis portfolio.
For so long You've been addingmoney to your 401k and now all
(02:35):
of a sudden you're supposed topull from it.
It's like no, no, no, I'm nevergoing to pull from it, I just
add money to it.
So I would start by saying thebig leap.
It's always going to be a leap,but how do you make it?
So when you jump in the waternot a perfect analogy, but you
jump in the water it's not thiscrazy splash where now all of a
sudden it's oh my God, who canyou hang out with and how much
(02:55):
income could you really support?
And it's more of a perfect divewhere you're in and you're like
, yep, I'm in the water.
I was more comfortable out ofthe water because I wasn't even
wet out of the water, but Ireally know I do want to go
swimming.
So it's first starting withthat.
Hey, it's going to be a leap.
How do we do it appropriately?
Speaker 1 (03:15):
Yeah, Tomorrow morning, my wife and I, we are
dropping off our daughter forher first day of preschool and
she's going to be I don't knowif nervous is the right word.
She just doesn't know what itis yet, but it's going to be
difficult.
I'm nervous, ashton's nervous.
This is a big change and Ibring that up because she's not
retiring, she's literallystarting preschool.
(03:36):
I think what we forget is thisis a very normal thing.
Your first day of school maybeyou remember, maybe you don't
Was that scary?
Probably Are you glad you tookthe leap and went to your first
day of school, maybe not beingcoerced into it by parents.
First day of high school Wasthat scary?
(03:56):
Probably so.
First day of college Was thatscary?
First day with a real grown upjob Was that scary?
Was that scary?
First day with a real grownupjob was that scary?
First time you asked out yourmaybe now spouse was that scary?
Ask him to marry you was thatscary?
Starting a family all of thesethings are scary and I think we
forget that because sometimesnot always, but sometimes by the
(04:17):
time that we're 60, 65, 70,like in those retirement years,
we haven't done one of those newthings in quite some time.
We're in that position where,like this commenter, say, hey,
I'm in a high paying job, whichprobably means you've hit your
stride, you've been there for awhile and you haven't.
Maybe you're not rememberingwhat it was like to be in that
job for the first time.
And so I think that one thingthat we have to do.
(04:39):
I always think like this.
Some people might think this ismorbid, but I always think
through.
I always think like this.
Some people might think this ismorbid, but I always think
through I'm going to die one day.
Am I going to be, if I have theopportunity.
When that happens, if I'mlooking back on my life and if
I'm this individual, am I goingto be looking back at myself,
kicking myself for retiringbecause I could have stayed in
that high stress job and I couldhave put more money in my
(05:00):
portfolio, which means, as I amgoing to my grave, I probably
could have had more money thatI'm going to die with.
Or am I going to be kickingmyself because I'm saying, look,
you stayed in that high stressjob too long.
It literally took years off yourlife, not just these extra
years of working that you can nolonger do the things that you
wanted to do, but the years ofyour health, that it took off
(05:21):
because your blood pressure wasout of control, because you
couldn't go to the gym, becauseyou couldn't eat healthy,
because you couldn't prioritizephysical health, mental health,
spiritual health, friendshiphealth, all those things.
Because of that, I don't know,but my guess is going to be it's
the latter.
So sometimes we have to askourselves the question of not,
what would I do in thissituation?
(05:43):
What will my future self do?
There is some study and I haveno idea where it's from so I'm
not going to try to cite itcorrectly.
But when psychologists look atour decision-making frameworks,
one of the reasons peopleprocrastinate which I think this
enlarged person may beprocrastination is our brains
(06:06):
literally think of ourselveslike James right now.
When James has somethingimportant that he doesn't want
to do in front of him and says,oh, I'll do it later, it's
because my mind is registeringfuture James as a completely
different individual, so it'salmost saying that person is
going to do it.
I'm not because it'suncomfortable for me to have to
do, but the problem is thatnever changes.
It's always that person, thatperson, that person meaning
(06:28):
later, later, later.
And if we could disconnect fromthat and try to think, no, that
both of those are me.
Both of them like at some pointwe need to make that decision,
is now the time to do it.
At some point we need to makethat decision, is now the time
to do it, and a lot of times thething that helps me is thinking
through the version of 85 yearold James, 95 year old James,
sitting there, hopefully inthose later years, being able to
(06:50):
reflect on a life and sayingwhat would I have been glad I
did?
And then trying, as best aspossible, to make the decision
that future me would have made.
So that's my thought.
Now we have some other goodcomments, I think in here to
this Username is Detroit Lions,dt Lions.
What are some other pieces offeedback this individual
(07:10):
received that stood out to you?
Speaker 2 (07:12):
So, first of all, you're not going to pass away
for much, much later, and I canonly imagine how you're feeling
right now with your daughterstarting tomorrow.
But my first thought is is shestarting tomorrow?
And there was no prep?
Was it just hey, you're goingto show up?
She doesn't even know whereshe's going.
Like, probably not You're.
You're probably told her, hey,you're, you're going to be
around other kids.
(07:32):
You might even know some ofthese kids that there's probably
some preparation that'soccurred that will make that
leap a little easier.
Now to your point, james.
Here we are giving analogiesabout your daughter jumping in a
pool.
It's not likely, as applicableto a lot of you who are going
hey, this sounds great, but youguys really aren't hearing me.
(07:53):
I'm about to retire, what do Ido?
And so here's the cool partabout this collective.
You get to hear from peoplelike Tommy C, who says the
following, and there's a littlelonger, but there's a few things
I want to read in here, so I'mnot going to read all of it, but
here's someone who says I tookthis leap 11 months ago, at age
56, and thought I would need tofind something part-time just to
(08:13):
keep my engineering by mindbusy.
Honestly, I haven't even missedwork.
Omg, the reduction of stressand the increase of time is so
liberating.
His guidance to once again,this Detroit Lions, this big
football fan, says here's what Iwould do.
I'd set up a plan to payyourself on the same schedule as
your current paycheck.
(08:34):
It'll feel like vacation planto keep yourself engaged with
your field and then go back ifyou want to, but you probably
won't want to.
And then the third one is justdo it.
And my only issue with this asa financial advisor where I want
to bring your thoughts in here,james is I love the idea of
just do it.
Nike's a cool brand.
I get why they started, just doit.
(08:54):
But it's really hard to do itif financially, you don't know
you're going to be okay.
And so, yeah, we're alwaysgoing to make sure people are
dreaming and think aboutretirement, because the worst
thing is you retire early and go.
Yep, I did it, I was over it.
Work was high stress, highpaying, but now you can't really
live your retirement.
Now you're retiring on eggs andtop ramen and that's probably
not ideal for most of you.
(09:15):
So, yeah, I like just do it,but the financial brain is going
.
I got to make sure you know youwon't run out of money.
Speaker 1 (09:23):
And I think this is a very important thing to
highlight.
Most people should not just doit.
Most people would do hey, thisis awesome, I loved retirement
for six months and then I ranout of money and it sucked.
I had to go back and that was.
That was me.
So we are making a bigassumption.
And not even a big assumption.
The reason we're jumping rightinto this is because username
Detroit lion says in mysituation, my analysis says I
(09:44):
can do it.
So he's run the numbers, runthe projections.
I don't know to what degree Iwant to double check those.
I'm going to see that.
But there there is this thingthat we've observed.
Another version of I'm going tocall it procrastination is.
I worked with clients beforewhere it's hey, you're in a
position to retire, awesome, andit's cool.
Let's run one more analysis, soone more analysis, so one more
analysis, and it becomes thisform of distraction, because
(10:07):
it's easier to address that, toaddress the thing that we know,
which is the financial side.
Way easier to do that than tosay what do I actually want to
do when I'm retired?
Who am I going to become?
What's life going to look like?
And I think that that's whystep one has to be are you
financially ready?
If you're not financially ready, do not just do it.
Work the hours you need to work, save the amount you need to
(10:28):
save.
Like, those things are not justthings.
You can leapfrog and go rightto the enjoyment phase.
But I think the point that wewant to make, though, is I don't
think I mentioned this enough,or reinforce this enough is I
actually think that a perfectlife is one that you don't
really retire from.
In some ways, like a perfectworld is you have a job that you
love and it fills you with somuch purpose and enjoyment and
fun that you can keep doing thatfor the rest of your life, or
(10:51):
at least until health no longerpermits.
Unfortunately, a lot of people,especially in high stress
corporate jobs, you just don'thave that freedom.
You can't make it somethingthat you want.
You have to pay your dues, youhave to trade your time for
money so you can invest thatmoney the right way and
ultimately live the things thatyou want to live.
But that's not to say retireinto nothing and saying, okay,
(11:11):
let's get away from that thingthat was high stress and
preventing you from the lifethat you wanted to live.
And now let's create that lifethat you do want to live and in
many cases, like some version ofwork whether or not it's for
money should be part of it.
Work can be something as simpleas everything from.
I know some people that verysuccessful careers and they're
now working at Trader Joe's,just because it creates this
structure and the sense ofcommunity and it's a fun
(11:33):
environment.
You know a lot of people thatgo work down at the golf shop.
I know a lot of people thatwork and they volunteer with the
local parks and rec becausethey want to just be part of
that and that's important tothem.
So keep doing something.
But to your point, ari, makesure the financials are in order
First.
We have plenty of podcastswhere we discuss how can you
tell if you're actually in aposition to retire?
(11:53):
We are just making theassumption or we're taking that
face value.
Making the assumption or we'retaking at face value Detroit
Lions comment, where he saysthat he is in a position to do
so, but it's hard to take thatleap.
Speaker 2 (12:03):
Yeah, james, check out to see if there's other
comments that you might want tobring up here, because I'm
curious and I'll tell everyone.
It's going to be a little toughlove for all of you.
And the reason I'm bringingthis up is I'm going to ask you
not to lie to yourself.
And it's going to be hardbecause some of you are going to
go.
You know what?
Yeah, I'm going to do apart-time job and it's going to
cover my healthcare costs.
(12:23):
And you're really still in thatmindset of, hey, I'm taking this
role because financially, Ineed it to do this or that.
Now, if you're taking a rolebecause financially you just
think, wow, this is going to addmore bonus money where I can
enter more pickleballtournaments and just show my
neighbors how much better I am,then I'm cool with that.
(12:44):
But if you're taking a role togo, you know what I really think
financially, I need to keepworking.
So I'm going to, and I don'treally love it, but it's for the
health care benefit and youknow, without that I'd have to
go pay 800 bucks a month on themarketplace.
I don't want to do that.
(13:05):
Well, it starts with that andthen it becomes okay, what next?
And what I'll see is people go.
Yeah, well, I have thispart-time job, but now I'm not
going to buy appetizers, becauseI was making 200,000 a year
before and now I make like30,000 a year and it just
doesn't feel right because Ijust I don't think I have it in
me.
And then the real problem isyou're 80 and you go.
I don't really think I need a$10 million and thinking about
kind of that morbid of, hey, I'mnot going to be here forever.
(13:26):
It's also the reality.
So are there other commentsthat you're seeing in there,
james, that resonate?
Speaker 1 (13:31):
Yeah, there's a few and I think, before I go, ari,
you do a good job of using thisexample.
A lot is to go back to DetroitLions comment of hey, it's hard
Like I should keep just um,working and saving and investing
.
Let's play that out.
If the goal is to keepimproving the financial
situation, why not always, neverretire, never stop saving,
(13:54):
fully, delay Social Security,cut out all the extra
discretionary spending on funstuff, cut out all the giving
that you do, cut out all, justkeep.
And obviously we hear that andsay, okay, that's absurd, and
obviously that's absurd.
And you can also be extreme inthe other direction, which is
why not just retire at the ageof 24, right after you started
your career?
Well, neither are good options,but it's about finding that
(14:17):
right point where you know thatyou're leaving on the table.
If you haven't invested in RSUs, I'm in that boat, but I've
decided enough is enough, enjoyyour retirement.
Here's another comment I want totouch upon, but that what he's
(14:37):
essentially saying.
Look, it's so hard when you sayhere's the opportunity cost.
The opportunity cost is there'smoney, a carrot that's dangled
in front of you that all youhave to do is stay employed till
a certain date and it's yoursand that is very true.
And that's very difficultbecause money is so tangible,
it's so quantifiable.
You know exactly what you'releaving on the table.
(14:57):
The reframe we'll try toencourage people with is there
is absolutely an opportunitycost to leaving money on the
table, and that's apparent, youknow it, and it's painful.
The thing that you don't see,the thing that's not apparent,
the thing that's just notobvious, is the opportunity cost
of continuing to work.
What's that year of healthworth to you?
(15:18):
What's that year of travelworth to you?
What's that year of adventureworth to you?
And, by the way, there's not aright or wrong answer.
In some cases it is the betteroption to work one more year to
get that extra bonus, more RSUsvesting, more contributions to
your 401k.
That is the necessary and wiseanswer sometimes, but other
(15:38):
times it's not.
And you have to be able to sayit's not just a one-sided
equation.
If it was just one side andjust about the money, never stop
doing this.
But when you realize it is abalance and there are other
things you need to consider,there is a very real trade-off
there.
It's just we don't see it.
And what makes us see it isthis comments that we get all
the time already on channels, onpodcasts and whatever it is, is
(15:59):
hey, I saved and saved andsaved, I finally retired.
I had all these dreams.
My wife and I were going to dothis and then she passed away a
year into retirement.
And it's like how much does thatperson wish they could go back
in time.
If that person could talk toDetroit Lions right now the
username for those of you tuningin late like what would they
(16:19):
say?
How much is money worth?
It becomes the thing thatdrives all of our decisions
until and this is why I thinkabout, like, wait, your future
self.
What are they going to think Atthat point?
Money is not a top 10 factoranymore.
So it just comes by looking atthis from all different angles,
all different sides, to say, yes, money is important.
We never want to discount that,but so too is the life that you
(16:41):
want to live and the thingsthat you want to do.
And what's the cost ofsacrificing those things just
for more money?
Speaker 2 (16:50):
And at some point, it's just no longer worth it.
Yeah, you always say that thesign of a good financial plan is
a life well-lived, and I knowthere's more comments that you
saw in there.
Were there any others youwanted to?
Speaker 1 (16:59):
reference.
Andy Wang had another one.
I won't read the whole thing,but he just talks about his
experience.
He says these podcasts from Ariand James have been helpful,
along with reading Die With Zero.
So that's a great book that Ijust like to recommend to people
to read.
Of this concept of what is moneyreally, how do we translate
that into its true value, whichin large part, is helping us to
(17:20):
have the experiences and do thethings that we want to do.
So, just for someone that's onthat edge and looking for that
sense of I don't want to saythat push, because we shouldn't
be looking for a push if we'renot financially ready yet, but
if we are financially ready weneed that push.
First and foremost, join theroot collective.
It's free.
There's a link in the shownotes here.
Go check it out.
Lots of great things you cantake away there.
But then that books a greatperspective, along with just
(17:43):
trying to put yourself in theshoes of your future self,
because your future self isgoing to have a more objective,
a more disconnected perspectiveon this than you will in the
moment.
Speaker 2 (17:53):
And by no means do James or I go.
Yeah, so everyone's going tolisten to this and just feel the
comfort to go to their firstday of school or to go retire.
That's not what we're expecting, but to join this collective
and see what other people sayand it's completely free, by the
way.
Just go hear from others.
You might take some ideas andyou might even feel that you
learn things you otherwisedidn't know.
(18:14):
There are people who are in thecollective talking about hey,
this feels really weird, butlike I think I'm in a spot to
retire, but like my neighbor, Iknow they have way more money
than me, in a way bigger houseand like I heard them talking
about working till 65.
And so now I'm thinking like,did I just miss something
entirely?
Because I don't think I'manywhere close to retiring, but
I also know that, like ourvalues are different.
(18:35):
And then someone else was inhere saying, oh my gosh, I felt
the same thing and I evenstarted working extra because I
thought I had to and you don't.
It's all custom based off thelife you want to live.
So certainly check out thatcommunity called the Root
Collective and you'll see it inthe description of this episode.
Anything else for today, james.
Speaker 1 (18:56):
I don't think so.
I think that that's a verynormal feeling to have.
As much as we say, do it asmuch as we say.
Here's the perspective.
It's going to be scary Anexample.
So when I started Root, someoneleft this comment that I liked.
Let me see if I can go to it.
Evan commented my job steppedaway from me a year ago so I
retired early.
You know somewhattongue-in-cheek, just saying,
(19:16):
look, I got terminated.
I know so many stories of peoplelike, hey, I got released from
my final job.
That was the best thing thatcould ever happen.
Like the boats were burned forme.
I didn't have to make thedecision.
I know when I started Root,that was the same thing it was.
I got let go from my previousjob and it's like, hey, the
boats are burned, go.
And it's like, oh my gosh, howscary was that.
Well, it was less scary becausesomeone else made the decision
(19:38):
for me.
It's the decision.
That's the scary part in manycases.
And once you make it and don'tmake it ill-informed, don't make
it if you're not prepared, butonce you make it, there's so
many good things on the otherside and one of the things we
try to help people do is how doyou live better lives?
Well, one way that you do thatis you get out of this high
stress job, no matter how highpaying it is, assuming you're a
good financial spot and youstart living, and it starts with
(20:01):
that decision.
So join the collective, reachout to root.
Speaker 2 (20:05):
If you need an advisor to help you do so, root
financialcom click see if youyour fit, but lots of great
resources out there to help withthat.
I, along with others, am sograteful that that boat burned,
which brought you to join andcreate Root and allow us to have
this community.
So to that one boat I'mgrateful.
Speaker 1 (20:22):
Awesome, I love it.
Well, thanks, ari.
Anything else you want to addhere?
That's it All right.
Thanks everyone, and we willsee you next time.
See ya, that's it All right,thanks everyone, and we will see
you next time.
See ya.
The information presented isfor educational purposes only
and is not intended as an offeror solicitation for the sale or
purchase of any specificsecurities, investments or
investment strategies.
Investments involve risk andare not guaranteed.
(20:44):
Any mention of rates of returnare historical and illustrative
in nature and are not aguarantee of future returns.
Past performance does notguarantee future performance.
Speaker 2 (20:52):
Viewers are encouraged to seek advice from a
qualified tax, legal orinvestment advisor professional
to determine whether anyinformation presented may be
suitable for their specificsituation.
Speaker 1 (21:03):
Hey everyone, it's me again for the disclaimer.
Please be smart about this.
Before doing anything, pleasebe sure to consult with your tax
planner or financial planner.
Nothing in this podcast shouldbe construed as investment, tax,
legal or other financial advice.
It is for informationalpurposes only.
Thank you for listening toanother episode of the Ready for
Retirement podcast.
(21:23):
If you want to see how RootFinancial can help you implement
the techniques I discussed inthis podcast, then go to
rootfinancialpartnerscom andclick start here, where you can
schedule a call with one of ouradvisors.
We work with clients all overthe country and we love the
opportunity to speak with youabout your goals and how we
might be able to help.
And please remember, nothing wediscuss in this podcast is
intended to serve as advice.
(21:44):
You should always consult afinancial, legal or tax
professional who's familiar withyour unique circumstances
before making any financialdecisions.
Popular Podcasts
40s and Free Agents: NFL Draft Season
Daniel Jeremiah of Move the Sticks and Gregg Rosenthal of NFL Daily join forces to break down every team's needs this offseason.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.