All Episodes

August 19, 2025 21 mins

When the numbers say you can retire, but you can’t step away. 

Many people with the financial means to retire keep working, telling themselves one more year will make the plan even stronger. But at what cost to your time, health, and relationships?

This episode explores “the good pickle,” where chasing more financial security comes at the expense of other forms of wealth like time freedom, social connection, and well-being. You will learn why money gets prioritized, how to rebalance, and simple ways to protect all areas of life so your plan supports more than just the numbers.

Because the true measure of success is not just a perfect projection, it is a life well lived.

-

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.

Create Your Custom Strategy ⬇️


Get Started Here.

Join the new Root Collective HERE!

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Every retirement projection you run shows that
one more year on the job isgoing to pad your nest egg, but
at what cost?
To your time, to your health,to your relationships?
In this episode we're going tounpack the different kinds of
wealth that are crucial not justto a financially secure
retirement, but to an overall,purposeful and enjoyable
retirement.
So stay tuned to see how youcan maximize life, not just
maximize your numbers.

(00:20):
Aaron, in our last couplerecordings we talked a lot about
the financial things peopleneed to do to retire whether you
need a million dollars to makeit happen, whether it's more,
whether it's less, the threesteps to get to that point of
how do you actually understandthe specific amount that you
need.
And today we're going to do acontinuation of that, and a
story that I think will serve asa nice foundation for some of
this is a client conversation Iwas having.

(00:42):
This was a couple of years backnow and this client was in a
great position to retire.
They wanted to retire, we ranthe numbers, they had enough,
but they were caught in a littlebit of what you might call a
good pickle.
Every year they waited, theywere in their peak earning years
, they were making really goodmoney and that felt really good
because they had worked reallyhard to get to where they were.

(01:02):
They couldn't walk away.
Or they felt like they couldn'twalk away because there was
some six-figure bonuses comingin each year.
They kept working.
Every year they kept working.
More of their stock, more oftheir equity compensation would
vest Every year they keptworking.
They were putting more intotheir 401k, they were putting
more into their deferred compplan, and every time we met they
would want to update theirfinancial model, their financial

(01:24):
plan.
And every time we met, theywould want to update their
financial model, their financialplan.
And for people who arelistening, you might be doing
this on your own, whether it'sExcel, whether it's just basic
calculators, whether you have aprogram that you run your
financial plan through.
But I think this is probably acommon thing people feel is,
every time we ran their numbers,it made sense for them to
continue working.
Every time we ran their numbers.
The more you work, the higheryour probability of success.

(01:46):
The more you work, the moremoney you'll have at the end of
the day.
And they couldn't break out ofthis.
Well, why wouldn't I keepworking?
And what we had?
To take a big step back andremind them or talk through is
when you are making the decisionto retire.
There's different scorecardsthat you should be paying
attention to and this particularclient they were purely paying

(02:08):
attention to, and I think a lotof us fall prey to this or
guilty of this.
Just looking at the financialscorecard, just looking at well,
how is this going to optimizethe financial wealth I have, my
portfolio balance, my net worth,the amount of assets that I
have, and that was the lens thatthey were really focused on.

(02:29):
And so today, what I would liketo do with you is talk through.
Is that the right way toapproach it?
I think it's certainly, atleast partially, the right way
to approach it, but I also thinkthere's some other
considerations that we should bethinking about when it comes to
that decision.

Speaker 2 (02:47):
I think I agree with you.
It's one scorecard that we canuse and I think we also live in
this society like in America wetend to think of that as the
most important scorecard Atleast our society kind of tells
us that because that scorecardyou can put a number to.
But if we look at the othersides of wealth whether that is,
how much control do I have overmy time or what do my

(03:09):
relationships look like, howhealthy am I feeling?
Am I finding a way to balancemy mental well-being as well as
my physical well-being, as wellas bringing in a paycheck, I
think that picture gets a lotmore nuanced.
But you can't put a score toyour relationships, not in a
literal sense.
You can maybe objectively andsay, hey, maybe I'm not

(03:32):
investing as much into myrelationships as I should
because maybe I'm working toomuch.
But that financial scorecard wecan see our net worth go up
over time.
We can see that if I hangaround to capture this bonus for
$5,000, I can get that investedand I can bump up that
scorecard.
And because it's so easy tomeasure, I think it's so easy to

(03:59):
focus on.
But I think let finances be atool to set you up to use those
other ones.
So I would argue that financesare pinnacle, but they're
certainly not the most importantscorecard.
I think all of them are equallyimportant in order to have a
balanced life.

Speaker 1 (04:12):
Yeah, I think that what you said is exactly right.
There's this, it's so tangibleI save one more dollar.
I see my portfolio balance goup by one more dollar.
I work one extra year and runthe projection.
I see there's this very tightfeedback loop of I'm very
quickly rewarded for making adecision or at least committing
to a decision, and there's thatfeedback, there's that positive

(04:33):
reinforcement of why wouldn't Ikeep doing this?
And I think that what we get socaught up in is thinking that
financial planning in asuccessful retirement or
successful life even, is like amath equation.
It's a math problem.
Just get the numbers right andthe bigger the numbers are, the
better your life is going to be.
There's a book that puts thisreally well that I recently read
.
It's called the Five Types ofWealth.

(04:53):
It's by Sahil Bloom and what ittalks about is that word wealth
.
Even when we first think aboutit, what do we think of?

Speaker 2 (05:01):
We think of portfolio balances.
What do we think of we?

Speaker 1 (05:02):
think of portfolio balances, we think of income, we
think of how much do we have inthe bank.
Whatever we're thinking of, itall has to do with money, with
finances and the way he framesit is.
There are five types of wealth,and financial wealth is one of
those framings.
That is one type of wealth thathe writes about in the book,
but there's also time wealth,there's social wealth, there's
mental wealth.
There's social wealth, there'smental wealth, there's physical

(05:23):
wealth, and I think that, eventhough some of those things are
maybe more difficult to measure,they're not as objective or not
as quantitative as okay, I cansave more money in my portfolio.
I see the immediate impact.
They are no less important and,I would argue, actually
increasingly more important theolder you get.
And so I'll go back to theexample that I gave this

(05:43):
individual making great money,great bonuses, more stock
vesting.
Well, they were doing thatbecause it's a very high stress
job, very demanding job.
It was not allowing them toprioritize their health, it was
not allowing them to prioritizerelationships, it was not
allowing them to have any senseof mental well-being, because
they were always on 24-7, butthey couldn't pull themselves

(06:04):
away from it.
Because, if we look at thosefive types of wealth and think
of each of those as a scorecard.
They're very focused on one.
The way I would think about itis let's say this individual
working one more year.
We talk about Monte Carlo,probability of success and how I
think it can be verymisinterpreted and now it has

(06:24):
its use cases, but it's also adistraction, I think, in many
ways.
Say this individual, theirMonte Carlo probability of
success went from 95% to 98%because of this work.
That feels good when that's allyou're looking at.
But if I then say well, aaron,what about the other scorecards?
What about social wealth?
Hard to score that, but doesthat go from a 70 out of 100

(06:49):
down to 50 because of thisdecision?
What about your mental wealth?
It's already pretty low.
Does it get even lower?
What about your physical wealth, your health, your ability to
do the things you want to do?

Speaker 2 (07:00):
I feel like so often we justify the financial
scorecard saying that it enablesthe other cards.
Like if I say I work longer andI earn a bigger paycheck that
might allow me to put my sonthrough college or that would
allow me to pay for a vacationwith my family.
So we use that financialscorecard to justify the others.

(07:21):
But I think a better framing isto kind of say it's a trade-off
.
If I work late night this week,I've now lost the dinner
opportunity with friends.
I've lost the opportunity tobuild that relationship and have
that social impact.
I've lost the ability to watcha movie with my child.
I've lost the opportunity to goon a walk with my spouse.

(07:43):
Like, I think you have torealize it's not just that the
finances enable you to do theother ones, but they also come
with that trade-off.

Speaker 1 (07:53):
How do you get through that?
How do you break through that?
Because I think you're exactlyright and I think that, over a
lifetime of almost programmingourselves or creating this sense
of here I'm so hardwired to notspend, or I'm so hardwired to
invest, or I'm so hardwired tofill in the blank how do we
start to pull ourselves out ofthat?

Speaker 2 (08:13):
and prioritize if we need to be prioritized.
For me.
I am very, very type A, I amvery hardworking, I'm a hustler.
So I actually had to put rulesin place.
I have a hard stop.
At the end of the day, and forme that is five o'clock.
My spouse comes home, my soncomes home, my phone goes away.
So if somebody texts me I don'tsee it.

(08:34):
I used to work late into theevening and say, oh, I can catch
up on this and we'll just havefun on the weekends.
But I found I was like missingconnection time and I really
missed my family, even thoughthey were in the house with me.
So I've put a hard stop.
My employees can't reach me, Ican't do social media, my phone
is gone and I'm just forced tobe present and that to me, has

(08:56):
been so rewarding with my familyand it pays back in dividends.

Speaker 1 (09:02):
Was it difficult to do that?

Speaker 2 (09:04):
Yeah, I mean, imagine locking your phone up in the
other room.
We're all so glued to ourphones so I mean, I think it's
hard to instate new practices,to have new habits, but if you
stick with them they becomesecond nature.
Now, if I were to have my phoneby me and it would go off, I
kind of think, whoa, why am Igetting a text at night?
This is not something I do atthis time.

(09:26):
I don't want to be distractedfrom the fun I'm having.
I don't want to be pulled awayfrom watching this show together
or going on this walk together.
And we intentionally schedulefamily vacations.
And it was so easy for years tosay, oh, we'll do vacations
later, we can take nicervacations later, but now,
whether it's the nicest vacationor not, we schedule it.

(09:46):
It could be a weekend getaway,it could be two towns over, but
we make sure that we have thosereprieves from works because
it's so easy to just say I'llwork through it and I'll get to
it later.

Speaker 1 (09:58):
I think that's the same thing that I see all the
time with people who struggle toretire.
Yeah, it's difficult.
I remember when I first becamea financial advisor, I very much
viewed my job as being theproblem solver and by problem
solver I mean the math problemsolver.
Like I love math, I love thecritical thinking, I love the
problem solving.
I thought, wow, I could come upwith a financial strategy.

(10:19):
You need to save this amountand invest this way, withdraw
this amount and you're good.
And it always.
I remember being so caught offguard when people would get that
financial plan and they wouldkeep working or they get that
financial plan.

Speaker 2 (10:33):
Like I solved this problem for you, why are you
still going?

Speaker 1 (10:36):
Exactly.
Something wasn't clicking untilI realized this is so much
deeper than just a financialthing.
This is really an identitything.
In a lot of ways, this is verymuch who I am.
There's fears to all this.
There's fears to who am I goingto be when I retire.
What's that going to look like?
But I think that simply anawareness is a great starting
point for people.
You talked about our lastcouple episodes.

(10:57):
We talked about how much do youactually need to retire, and
the reason we're doing this nowis sometimes people reach that.
But then there's this fear ofwell, what am I going to do?
Or there's this fear of I couldwork another year and be even
better off.
There's this fear of why wouldI not keep optimizing?
And I think that myencouragement to people is never
stop optimizing, but askyourself what you're optimizing

(11:20):
for.
Are you, by optimizing for yourfinancial wealth, totally
obliviating or just totallyruining your ability to optimize
for your relational wealth,your mental wealth, your
physical wealth, your timewealth?
That time thing is probably themost important of one day.

(11:40):
None of it's going to matterOne day.
None of the long hours, none ofthe savings on the portfolio is
even going to matter and, yes,that gets really deep and
philosophical.
But I don't think you canactually have a really good
financial plan until you alsohave at least some semblance of
a life plan.
What do I want to do?
What does a successful lifelook like?
What is most important to me,and am I using my financial

(12:01):
wealth to enable these otherthings, or am I sacrificing
these other things simply tooptimize for my financial?

Speaker 2 (12:07):
wealth?
I think, truly, we don't askthat question that often.
You know, what do I really want?
I think we kind of get caughtup in the day to day of like, ok
, well, I go to work at nine, Icome home at five, like this is
just what I do, but how often doyou say is there something else
I would rather be doing?
Is there something else thatwould make my life more
enjoyable?
And I think the problem withthe other types of wealth the

(12:28):
social, the time, all of hours Iimmediately get a bump in my
paycheck, right.
But if I skip going to the gymthis week, that doesn't show up
in my health, it doesn't show upon the scale this week, it
doesn't show up in the way mybody moves and how I feel in my

(12:50):
body.
But do that for 10 years or 20years.
It's going to show up, butthere's a delay to it.
So I don't think we take it asseriously.

Speaker 1 (13:02):
Yeah, and I think that one of the most important
things with all of this is allof these are learned behaviors,
in some way of going back tolike what you said, because I've
had that same thing oh, I'llwork hard today so we can take
even better vacations, do evenbetter things as a family in the
future.
It's in some ways, like notjust a skill like if you neglect
your family for the first 15years of their life and then all
of a sudden want to take greatvacations, those vacations

(13:23):
aren't.
They're going to be very lavish, it's going to look cool on
Instagram, but it's not going tobe any type of fulfillment or
joy or or the type of lovingexperience you want that to be
for your family.
These are things that you needto invest in the relationships.
These are things that you learnhow to do.
There's so many people who Italk to that are retiring.
I don't even know what I wantto do for travel.

(13:44):
I don't even know what I wantto do for community, for
relationships, and it's becausethose are things that they have
neglected for so long, tellingthemselves I'm going to work
hard today so I can do those inthe future, If you never learn
how to do some of those things,or if you never invest in some
of those things, they don't justautomatically become second
nature.
You don't just automaticallyhave best friends.

(14:06):
You don't just automaticallyhave amazing relationship with
your spouse, with your kids,with your family.

Speaker 2 (14:13):
There was a quote from a musician that I loved.
Like you can't make new oldfriends.
Like you only get a chance forsomeone to know you when you
were 20 or 30 or 40 by showingup every single year in this
relationship.
You only have a 10 or 20 yearmarriage by being there.
For the 10 or 20 years itdoesn't count if you just phone

(14:33):
it in and you're 19.

Speaker 1 (14:35):
Yeah, exactly.
And so I think that when peopleare looking at retirement, when
people are looking at financialplanning, when people are
looking at wealth, hopefully, Ithink our encouragement in this
is, yes, the money absolutelymatters.
Without the money, you can't doany of this stuff.
Yeah, finances, but yourability to be physically healthy

(14:59):
, your ability to be mentally,spiritually, whatever healthy
all across the board, those arethe things that you ultimately
want your money to be able tosupport.
So when you can think of it in amuch more holistic is kind of a
buzzword, but like a much morebig picture way of what do I
actually care about?
What are my values?

(15:19):
Truly, that's a much better wayof making decisions.
If I go back to the examplefrom the very beginning, yes,
that individual, if all they'relooking at when it comes to
their wealth and wanting tooptimize is the financial side,
never stop working, Work untilyou're 90.
Your financial wealth willalways keep getting better.
But what have you missed alongthe way?

(15:40):
And when you take a more, abroader approach to what is true
wealth, you're going to makebetter decisions.
When you start to think throughwhat are the trade-offs I'm
making along the way.

Speaker 2 (15:51):
What do you think is the number one thing you can do
to kind of get to the pointwhere you say, okay, it's enough
, because when all of the datasays you have enough to step
away, what do you think?
There is a nudge or some kindof nugget of information that
you could be like okay, I feellike I have enough, not just
intellectually.
What helps you feel that way?

Speaker 1 (16:13):
I don't think you can do this unless you know thyself
, and this comes from journaling, meditating, being quiet.
We live in such a culture wherethe from the time that you wake
up until the time that you goto bed emails, instagram ads,
things, deadline, like we don'tactually know what we want to
know.
We don't actually know what wewant.

(16:33):
In many cases I would arguemost people don't, because from
the time they wake up to thetime they go to bed, their
attention is being pulled at orcontrolled in many different
directions and you neveractually get to the sense of
what do I actually want to do.
I know one of the things that'smost helpful for me is just
being up early before the familyand spending time, journaling,
spending time asking myself thisquestion what do I actually

(16:56):
want?
Why am I waiting for some ofthese things?
Why don't I start doing some ofthese things now?
Why don't I?
And it's not like the answersdon't just magically come to you
, but when you actually startseeking, you will find that, and
you you have to start by.
I think this is journal, read,write, meditate.
Just have some silence to saywho is Aaron and what's
important to Aaron.
Who is James and what'simportant to James If I think to

(17:20):
the end of my life.
One thing I like to think aboutis what are the things my
future self is going to begrateful that the current
version of me did?
If I think to the end of mylife, what's actually going to
be most important when I'mtalking to my spouse, my kids,
my friends, coworkers, et cetera.
What do I want thoserelationships to look like?
What do I want those outcomesto look like, et cetera.

(17:40):
What do I want thoserelationships to look like?
What do I want those outcomesto look like?
Great, what were the things Ineed to do today be to get there
?
And it could be very simplethings.
It could be exactly what yousaid.
I want to have a greatrelationship with my children.
How do I do that Presence Forthe age they are?
Today?
I'm not going to touch my phonefrom the time they wake up at
seven until I go to work at 8.30.
The time I come home at 5.30until they go to bed at 7.30, my

(18:01):
phone's.
I think that's a very simpleaction, but what it's doing is
it's a reflection of this iswhat's most important to me.
I could be answering moreemails.
I could be growing the businessmore by being on my phone more,
but that's not the wealth andthat sends a strong message to
your kid when you're like it.

Speaker 2 (18:17):
Like my son is just under two, he can't be like oh
okay, put your phone down.
But if I'm on my phone, like heknows, my eyes are not on him
and there are times like I'llput my phone down and I just
walk away.
He'll pick my phone up andhe'll bring it back to me and
honestly, that's a sweet momentbut it kind of breaks my heart
because he thinks like oh, youneed this.

(18:43):
Here you go, so I need to getbetter at the phone thing.
Yeah, and do you have any otherthoughts on that?
Erin, I think what you said isvery powerful.
You just make sure that youhave time for you, because it's
so easy to just have yourattention going in a million
different directions and forgetto even consider what's
important to me.
You spend your whole dayreacting to someone else that
it's easy to lose focus of whatreally matters For me.
I go on long runs and I run forlike an hour and during that

(19:05):
time I might listen to a podcast, I might listen to music or I
might just kind of like take inthe world around me and it gives
me an opportunity to say, okay,like how is my day going, how
are things going with my family,what are the things I want to
accomplish this week?
But it just gives me a mentalbreak from work, from people,
and allows me to spend time withmyself, and I feel like I

(19:25):
better nail down what I want togo after in life in those
moments.

Speaker 1 (19:29):
Yeah, awesome.
So that's our encouragement.
Take the time, set time aside,think who are you, what do you
want to do?
What does true wealth look likefor you?
Not just the financial side,but think of the financial side
as enabling the other aspects,enabling the relationships, the
purpose, the health, otherthings.
When you can just think throughthings in that lens, you don't

(19:50):
need like a perfect metric ofhow do I measure social
well-being, how do I measure,but that framework and that lens
can help you make the righttypes of decisions.
But that framework and thatlens can help you make the right
types of decisions.

Speaker 2 (20:01):
I will give the two cents of like.
Maybe it is worth writing outthese different categories time,
social, mental, physical,financial and giving yourself
some kind of score, because atleast if you say, oh, I'm really
dragging in social, maybe youspend some more time there.
So if you can put some kind ofmeasurement to it, maybe you

(20:24):
score yourself one out of 10,you can say where you need to
kind of focus a little bit more.

Speaker 1 (20:26):
Yeah, exactly.
And then again, the book thatI'm basing some of this on is
called Five Types of Wealth.
Go read it.
This isn't an endorsement,we're not going to pay for this.
I just thought it was a verygood book that helps to reframe
how you should think about aboutwealth to have.
I'll always say with clients,with the team, the sign of a
good financial plan is a lifewell lived.

Speaker 2 (20:44):
Yeah.

Speaker 1 (20:44):
It's not a 99% success score on your Monte
Carlo, it's not a certain networth, it's a life well lived,
and that covers all these thingsbroadly, with the financial
wealth being the bedrock thatsupports it all.
So anything else, erin, to addonto this before we wrap up for
today?

Speaker 2 (21:01):
I think that kind of covers it.
I would just say, you know,focus on the other areas, not
just money.

Speaker 1 (21:05):
See you all next time .

Speaker 2 (21:07):
See ya.
Advertise With Us

Popular Podcasts

Stuff You Should Know
My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.

The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.