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May 15, 2025 16 mins

Retired with millions—but full of regret?

In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential.

What you’ll learn:
Common regrets wealthy retirees confess after leaving work
Why financial freedom means nothing without health, time, or joy
How to avoid estate planning mistakes that burden your spouse or family
Why intentional living matters more than chasing a number
Simple, high-impact ways to prepare for retirement now

If you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for you

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

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 1 (00:00):
I'm going to guess that the majority of you
watching this content orlistening right now are good
savers.
That's why you are where youare.
That's why you're listening tothis content, thinking of ways
to further optimize yourfinances.
Now, some of you are thinkingmy partner is a great spender.
Okay, well, we're not talkingabout them right now.
We're talking about you in thissavers mindset, and one of the

(00:21):
coolest things that we haveright now at Root going on is
this community.
It's called the Root Collective,and in this collective, there
are certain prompts that I'llsee that will catch my eye or
James's eye, and that's how wecome up with what we want to
talk about today, and so todayis a really interesting one, and
this was prompted by Tommy C,who says the following For those

(00:43):
who are great savers beforeretirement and are now retired,
what are the little splurgesthat you now spring for that you
wouldn't before retirement?
And he has a couple in herethat might make you think a
little differently about how youwant to save or potentially
spend or give, or X, as we'lltalk about today.
James, when you're seeingsomeone talk about, oh my gosh,

(01:07):
what are some of these thingsthat maybe I wouldn't normally
do, but now that I'm retired,I'll consider doing what's
coming to your head Well, firstthing is number one let's not
wait until retirement to do someof these things.

Speaker 2 (01:19):
This isn't like a binary you don't do these things
before you retire, do thesethings after you retire.
But number two I think thatwe've heard a lot of cool things
, a lot of cool tips, if youwant to call it that, spending
strategies, of what are someexamples of people, of things
people spent money on and theyhaven't regretted it, because no
one wants to spend money andthen regret it Like, why did I
buy that stupid thing?

(01:40):
I never ended up liking it.
What a waste of money.
I feel dumb for doing it.
But there's other things peoplespend money on and they say I,
that was one of the best thingsI've ever spent money on.
And so I think that I, broadlyspeaking, categorize things into
one of five buckets where wesee these are like some pillars
of good spending and so we'll goover those.
And then you have some personalthings.

(02:01):
I know, I have some personalthings.
I know, and I, you know, whenwe're talking to clients, I
think one of the fun things isbecause our advice isn't just
about money, money, money.
It's really about how do youhave a, how do you live better
lives.
How do you live moreintentional lives Like these
aren't things that are unique toage 65 and above.
These are really principlesthat all of us can try to live

(02:21):
better by, and things that youand I personally try to live
better by, so we'll share someof those stories as well.

Speaker 1 (02:27):
We certainly will.
We talk about this phrase ofgoalpost planning One more year,
one more bonus.
Oh yeah, just one more project,then I'm going to officially
retire.
Now, if you're doing thosethings, some of you are like
it's because I don't know what Iwant to do in retirement.
Others of you are like you knownow that you've actually
brought it up.
I think you're right and Ithink when I'm hearing you guys

(02:47):
talk, it's resonating becauseI'm doing that, but I wasn't
even aware, am I doing that?
So what we want to do today isreally shed some light as to
some of these ideas, whichhopefully will make you think a
little bit more.
Intentional is the way I wouldsay it.
So, if it's okay, excuse me,james, I'd like to start with a
quick story, because it's afunny one and my clients like
when I share it.

(03:07):
So some of you guys alreadyknow this, but for those who
don't, my dad loves his phone toan unhealthy degree and I love
spending quality time with mydad.
My dad loves surfing.
I'm not a huge surfer, but Iwill go out with him in the
water because it's when I gettime with him.
Now he actually has his AppleWatch, so sometimes he takes
calls when we're in the water,which he knows he's not allowed

(03:30):
to do, and I feel like I'm theparent when that occurs.
But my brother and I werethinking for a long time how do
we get more quality time withour father?
And we can't surf all the timeif waves are up or it's windy or
whatever it is and so we boughta sauna to intentionally ensure
that his phone or Apple watchwould overheat, so he's forced
to talk to us.

(03:50):
Now some of you are thinkingwell, that's silly.
Why don't you just talk to yourdad for dinner?
And if it was that simple, wewould do that.
But we all know some of us havethese family members where it's
just more difficult to get themengaged, whether it be game
night or you just have to takethem out to dinner because at
home they're going to kind of bewatching TV.
So I am literally payingthousands of dollars, along with
my brother, to just get qualitytime with my father, and that's

(04:13):
something that I could wait todo until I quote unquote have
millions of dollars retired.
But I want the time now, whileit's valuable.
So we'll certainly get into,james, your stories, we'll get
into what prompted today, butthat's a quick story about just
financially, why doing the rightthing might not always actually
lead to the right result.

Speaker 2 (04:33):
Well, I think that's a perfect example of the.
Here's my five pillars.
There's nothing magical aboutthese as much as when I hear
great stories like that, by theway, of what people spend money
on that they feel really goodabout spending money on.
The first pillar is experience.
No one is ever upset that theyspent money to buy an experience
and in this case, theexperience was simply quality
time with your dad and that,theoretically, could have

(04:54):
happened on the sofa.
That could have happened.
Surfing, that could havehappened driving a car.
But, like you're saying, therewas a roadblock to that
happening.
You needed to eliminate theroadblock, which was overheat,
the phone so it couldn't be used.
But experiences, that's whattravel is, that's what doing fun
things is, that's what you'retalking about.
Number two is time.
No one ever regrets spendingmoney to buy their time back.

(05:18):
I've used this example before.
I do not like going to thegrocery store.
In fact, I hate going to thegrocery store.
And so he said how do we spenda few bucks to get food
delivered, groceries delivered,I think it's $10 per order, so
weekly it's 10 bucks, plus thetip that you leave.
How many hours does that saveof driving to the grocery store,
going through the aisles, andit's just not a fun experience.

(05:40):
So that's a couple hours oftime back that I now have.
So time, how do you spend moneyon time?
The third is giving.
No one's ever upset that theygifted money.
This could be gifted to acharity, to church, to family,
to friends, to whoever it isYou're not going to feel like
that's a great thing to quoteunquote.
Spend money on is giving.
Then you have health.

(06:00):
No one's ever upset that theyspend a lot of money on health.
You tell a lot of stories aboutthis, ari, of getting the best
doctor, of the physical therapy,of the things that you do, and
health is one of those things.
That.
What's the saying?
A healthy man has a thousandworries, a sick man has but one,
or something like that.
Like, until you don't have yourhealth, you don't think about

(06:23):
it.
But health is, health is whatallows us, of course, to enjoy
everything else that we have.
So spending money on yourhealth gym memberships, good
food for you, eating good food,spending money to do things that
makes you healthier is a greatthing to spend money on.
And then, finally, I'll justbroadly talk.
Call it environment.
You want to live in a beautifulenvironment you want, whether

(06:43):
that environment isaesthetically pleasing, and this
is about people who like todecorate their home a certain
way or do certain things fortheir home.
This environment could beproximity to people you love or
you care about.
The environment could beproximity to things you enjoy
doing.
So I think those are categoriesthat, broadly speaking, we
should be spending money on.

(07:03):
I like your example.
For me, an example that comesto mind is not so much spending
money, but spending time is.
You mentioned goalpost planningjust a bit ago, and it's the
sense of oh, I'm going to workone more year because I'm going
to get one more bonus, or I havesome more stock vesting, or
it's one more year of socialsecurity benefits increasing, or
it's one more year of maxing.
There's so many good financialreasons we can use to justify

(07:27):
that, and what we always pointto is they at some point you
could take that to the extremekeep working forever, keep
maxing your 401k forever, keepgetting bonuses forever, but you
missed the whole point.
You missed the movie.
Your life passed you by becauseyou spent it working.
Now I'm assuming you're workinga dead-end job Not a dead-end

(07:47):
job, but a job that you don'tlike A job that's not bringing
you fun and fulfillment in thethings you love doing.
So we try to help clients bevery intentional with.
That of money has a purpose, avery important purpose, but at
some point the money needs tonot be the main thing.
At some point you've crossedthis threshold where there is
enough that it can now supportyou doing the things that you

(08:10):
actually want to do.
And continuing to work to geteven more of it is actually
pulling you away from whatyou're actually trying to do.
To work to get even more of itis actually pulling you away
from what you're actually tryingto do.
I face that too, not because I'mtrying to retire.
I love what we get to do.
This is one of my favoritethings in the world.
To me, it's not a goalpostplanning of okay, I'm going to
stay at root for one more year.
Two more years is man.
I can get one more thing done,two more things done, three more

(08:32):
things done, and surfing issomething I claim to love to do.
I haven't done it in two and ahalf years and I blame it on
okay, well, we have young kidsand life's busy, and I blame it
on well, roots growing and thatkeeps me busy.
The reality is, I'm just notmaking time to be intentional
with it.
And Wednesdays is typicallywhen I record YouTube videos,

(08:53):
podcasts et cetera, and I alwaystell myself, okay, I'm going to
record and, like the, the, thereward for doing that is going
to be then I'll go surfing, orthen I'll go I don't know do
something fun.
I'll go do jujitsu, I'll gotrain.
But I fall into that same trapthat we encourage clients not to
not have.
Oh, there's one more thing Ican be productive with.
There's one more thing I cancheck off the list.
Look, I have three more hourstill I got to go home for family

(09:15):
dinner.
Like, look at all these thingsI can do.
And I fall into this trap andit's and, and just last week,
for the first time in two and ahalf years, I finally said you
know what I'm going to commit to.
Here's the things I need to getdone today the my enough.
Like, if I get these threethings done, which was filming a
certain amount of videos, I amgoing to go surf, and I did it
and I went surfing and I wasreflecting on the way back that,

(09:37):
as much as we tell clients todo this of don't goalpost plan,
don't don't keep pushing off thethings you actually want to do
I personally am guilty of now.
I love work, and so it's notlike I'm continuing to do
something that I dislike doing,but there's a certain amount of
intentionality that doesn't comefrom continuing to do the same
old, same thing.

(10:01):
Like, how, like, how do youconstantly reflect on what
should I be spending money on,like your story?
What are the things I can do tocreate more meaningful
experiences?
What are the things I can do toimprove, spend money on, to
improve my health, to buy backmy time to you know those
various things I talked about?
The same thing happens with howdo we spend our time Not just
how do we spend our money, buthow do we spend our time, and
sometimes it's thinking aboutthe life that we want to live.

(10:22):
It's thinking about whatactually matters to us, and
surfing is obviously not theonly thing that matters.
In fact, it's pretty low on thepriority list of the things I
actually care about but ingeneral, it is something that I
do want to do, and it's thissense of just constantly
reevaluating and reassessing.
Where are we and how can wespend our time, spend our money,
spend our energy, spend ourtalents, doing the things that

(10:42):
bring us closer to the life thatwe want to live.

Speaker 1 (10:45):
Now this is interesting.
What was it about last weekversus any other week in the
last two and a half years thatmade you go?
Today is the day I'm going togive myself the reward.

Speaker 2 (10:55):
You know I didn't think about.
Well, I'm glad you just askedthat, because I hadn't thought
about this until literally thesecond.
An office mate came in thismorning and said guys, we work
four blocks away from the oceanand we never get in the ocean.
How ridiculous is that Kind oflike, how dumb are we that we
live in this paradise and wedon't actually utilize the
paradise we live in?
And so I said, okay, well, if Ican get you're right, first and

(11:18):
foremost, and number two, if Ido this isn't to say abandon all
work and go.
If I can get my enough done, ifI can get my top three things
that are my priorities for theday done, instead of just saying
, okay, cool, there's alwaysmore things to do, so I'll just
pour myself into that Then I'mgoing to go do this other thing
that is called a reward forgetting those things done.

(11:39):
I don't want to call it peerpressure, but having someone do
this and I think in fact, thatcomment, ari, that you started
with from Tommy C mentioned thatI believe correct me if I'm
wrong, but one of hisexperiences, one thing he spends
money on, is doing somethingthat friends can come along, and
it's that sense of doingsomething with someone else

(12:01):
makes it way easier to do andway more enjoyable to do.

Speaker 1 (12:05):
It's so fascinating because, let's assume, you go
surfing every week and nowyou're happier at home, and now
your wife goes.
We're connecting more.
I don't know what's happening,but I just feel it's different
and you're more present and youcan't quantify that on some
spreadsheet, as hard as you try.
And there are financialadvisors as nerdy as us who will
try, but the reality is you arenot going to look back going.

(12:28):
Oh my gosh, I'm so glad I didthose 12 more projects and you
know I didn't need more timewith my grandkids, like we've
never heard anyone ever say that, and this is all we're doing
all day.
So I think when we're talkingto clients, we will pride
ourselves on being verytransparent.
We will pride ourselves onbeing very transparent.
We are not mean, but we aretransparent because, as you just

(12:51):
saw, what prompted James toactually right now go surfing
was someone came into the officeand said how dumb are we?
And so some of you are workingright now going.
I'm 60.
There's no way I could retirebecause I've never had
healthcare outside of myemployer, so surely I'm waiting
until 65 because, like, why not?
And then you'll see a videothat might wake you up and go
hey, maybe that's not the deal.

(13:12):
And then all of a sudden youmight have years back of
prioritizing health or family orfriends.
And next week we'll talk aboutan even bigger story actually
two weeks from now where there'san actual woman I spoke to who
was really upset that she had $3million, and I said, look,
that's just.
I don't want to be mean here, Ijust don't hear that every day.
Why are you mad that you have$3 million?

(13:33):
And she goes on to say that shedidn't need 3 million and now
she can't hike to the degreeshe'd like because of the health
impact from sitting at work.
So we'll talk more about thatin a few weeks.
But the point here isfinancially, there are things
that you can only do when youknow your plan allows for it,
but you don't have to wait untilthis magic date to actually

(13:54):
start doing some of these things.
So I think it would be helpfulto maybe give some of you guys a
few ideas here.
And, james, if there's anythingyou wanna add, please feel free
.
But this is straight from Tommyonce again in the community.
But this is straight from Tommyonce again in the community.
These are just a couple of hisideas, and so he says whenever I
have an experience, he springsfor the better and the closer
seats.
That might not be valuable toyou, but that's what he likes to

(14:15):
do he talks about.
Whenever he can.
He gets prepaid parking so he'snot worried about finding
street or cheaper parking orhaving to walk a mile to the
venue like James did when he wasyounger at the baseball games.
He says he'll upgrade to alarge or even extra large coffee
.
He says when I'm on a cruise, weopt for excursions that have
less people and they cost alittle bit more.

(14:36):
The experiences have been 100%worth it.
He tips more generously.
And then our favorite one thatwe read here is he said when I
buy experiences, I buy two extratickets.
This forces us to find twofriends to go with us.
If they pass back, great, andif not, I'm not worried.
More fun with friends is worththe additional cost.
So he goes on to say what littlethings do you splurge on that

(14:58):
makes you happy?
I don't think those are litterthings.
I think those are big things.
And I want to tell Tommy I'mproud of you because it's really
hard Unless you know.
I want to tell Tommy I'm proudof you because it's really hard
unless you know financiallyyou're in a good spot to go.
I'm going to buy two extratickets.
What if my friends don'tactually join?
So if there's anything you takeaway from today's episode, I
hope you think about it and letthis be.
Maybe this episode, the personwalking in to your office going

(15:22):
maybe today's the day to gosurfing.
Anything else, james, you wantto add?

Speaker 2 (15:25):
No, I James.
You want to add?
No, that would be it.
I encourage everyone listening.
Just keep it super simple.
How could you better spend yourtime and how could you better
spend your money?
My example was a time thing.
Your example was a money thing.
Now you're spending your moneyto get time and I think that
that's how do we live betterlives.
We look at those two things.
Where are we spending money?

(15:46):
How are we spending money?
I have five things that like tofall in those categories.
Again, experiences, time giving, environment or health.
If it's checking one of thoseboxes, I'm going to feel good
about it.
So what is one little thingthat we can do?
What gym can you go sign up forNot just sign up for a gym
You're probably never going togo.
Can you sign up for a personaltrainer to keep you accountable?

(16:06):
Can you sign up and do so witha friend, to keep you
accountable, to make it fun?
What are those things that youcan begin doing?
What are those experiences?
To me, the simple experience wasI'm going to go surfing for 30
minutes in the middle of the daybecause I got my enough done.
What are those things that youcan do?
I'm really glad I did it.
Whatever I would have gottendone in those 30 minutes pales
in comparison to the fun I hadbeing in the water, doing that,

(16:27):
having fun with a friend.
So just those little things.
So what's one single thing youcan do to stop?
I'm guilty of this?
You're actually really goodabout this.
I bet you're not actuallyguilty of this.
You get in the routine, you getin a thing that's comfortable
and it's hard to kind of pullourselves out of that until
someone comes along and showsyou those blind spots that by
nature, by definition, you'renot seeing in your own life and

(16:49):
you have to go make a change toget out of it.

Speaker 1 (16:52):
Well, thank you, and we're going to put the thread of
what Tommy said in the linkbelow.
So if you want to go comment onthe exact post, which is the
reason we're making this exactepisode, go comment in there and
let us know and we will readthose ideas on future episodes.
So you can check all of thatout in the description, whether
you're on YouTube or on thepodcast app.

Speaker 2 (17:12):
All right.
Thank you everyone forlistening and we will see you
all 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.
Any mention of rates of returnare historical and illustrative

(17:32):
in nature and are not aguarantee of future returns.
Past performance does notguarantee future performance.

Speaker 1 (17:38):
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 Once again.

Speaker 2 (17:49):
I'm James Canole, founder of Root Financial, and
if you're interested in seeinghow we help our clients at Root
Financial get the most out oflife with their money, be sure
to visit us atwwwrootfinancialpartnerscom.
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