5 Signs It’s Time to Retire - Right Now

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers.

Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly moving the goalpost while trading away your most vibrant, healthy years.

In this episode, we explore the critical difference between lifespan and healthspan. While many Americans live into their 80s or 90s, our healthiest years typically decline around age 66. Waiting too long to retire may leave you with more money, but fewer active years to travel, hike, or be present with grandchildren.

We also unpack the emotional side of retirement: the identity loss many face when stepping away from their career, and how this psychological barrier—paired with strained relationships from decades of overwork—can keep people stuck longer than they should be.

Retirement isn't just about having enough money. It's about having enough life left to enjoy it.

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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.

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Episode Transcript

Speaker 1 (00:00):
Imagine real quick that you're 90 years old.
You're looking back on yourlife and all that happened.
Are you thinking about thefinal bonus that you had, or are
you thinking back on the timethat you didn't spend with loved
ones?
Far too often, the regretspeople actually have have
nothing to do with finances andhow much money they didn't spend
, the bonuses they didn'treceive.
They regret the things theydidn't do with family, with

(00:21):
loved ones, the activities thatthey wish they would have done
more of.
That's why the topic of today'svideo is five signs that it
might be time for you to retire.
I'm a financial advisor that'sworked with hundreds of people
over the course of my career, soI know that financial readiness
is the key.
But there are also theseoverlooked reasons that people
don't spend enough time thinkingabout when it comes to their
retirement decision, and that'swhat I want to cover today.
So let's go through the fivereasons that might be time for

(00:43):
you to retire now.
And reason number one is timeis the only non-renewable
currency.
What I mean by that is time isthe only thing you can't get
back.
Theoretically, you can alwaysmake more money.
It might get increasingly moredifficult the older that you get
, but you can always make moremoney.
You can never make more time.
When we're young, we reallyprioritize money because we
think that time is endless andso we need to prioritize money

(01:04):
building our money, saving ourmoney because that creates the
freedom to do the things we wantto do.
But as we start to get older,there comes a point where
there's a crossover.
Now, of course, none of us knowhow long we have, but at some
point we need to start realizingthat it's that time that's far
more important than money.
What I see too often is peoplewho think about retirement and
all the wonderful things that itcan bring.
But there's so much in thismindset of I need to work, I

(01:27):
can't pass up another bonus, Ican't pass up another round of
stock investing, so it'sgoalpost planning.
They keep pushing back andpushing back and pushing back,
thinking that at some point, onemore bonus, one more portfolio
milestone and they'll feel moreconfident to retire.
That never comes, unfortunately.
What does come is what comes isa sense of regret of people who
push retirement to 65, then 67,then 70.

(01:49):
And they realize that those areyears of their life that
they're never going to get back,and not just years of their
life, but the healthiest yearsof their life, the years they
could have spent traveling, theyears they could have spent with
family, with grandchildren,doing activities that they loved
, and because they viewed moneyas a thing to get more of, not
from a selfish mindset, not froma greedy mindset, just from the
mindset.
That's what they've alwaysprioritized.

(02:10):
That's what their financialplan has always been about.
They have not spent enough timethinking about time.
How much time do we really have?
And that is a non-renewablecurrency.
So, yes, we need balance.
We need to have enough money tolive, but we can't constantly
trade our time for money,because at some point, that
money is not actually going tofulfill its intended purpose if
we don't make the time to use it.

(02:31):
The second reason it might betime for you to retire is
because you need to invest inyour health before it's too late
.
We need to acknowledge thatyears and decades of work and
stress and burnout are not goingto be the only way to make a
difference in our lives.
It takes a toll on our healthand if we are not prioritizing
our health, we're not going tohave the thing our bodies, our
healthy bodies that are actuallynecessary to do the things we

(02:51):
want to do in retirement.
There's a growing number ofretirees who are experiencing
depression, anxiety,stress-related, chronic health
conditions and we don't think ofthat in retirement.
We think of retirement asstress-free, as relaxing, as
like a vacation.
But the reason for this is theypushed so hard, they never
prioritized their health andwhat they now have is a

(03:11):
retirement where they haveplenty of time but they're not
able to use that time how theyotherwise would have wanted to
because they didn't prioritizetheir health.
So if that's you, it might betime to retire.
How do you prioritize yourhealth?
How do you prioritize exercise,the way you eat, the things
that you do with your body, withyour mind, with your spirit?
These are the things that youcan't get back.
These are the things that, ifwork is preventing you from

(03:33):
doing everything you need to doto maintain those and you're in
a financial position to do so,it might be time to retire now.
The third reason it might betime to retire now is so that
you can prioritize yourrelationships.
Let's think about your workweek relationships.
Let's think about your workweek.
You spend 40 to 50 hoursworking.
You're commuting for somenumber of hours per week.
You're running errands, you'redoing the things around the home
.
How much time do you actuallyhave left and not just time, but

(03:54):
quality time to invest inrelationship with your spouse,
with your children, with yourfriends, with the people that
actually make life worth living?
So much of your happiness andeven your lifespan in retirement
is going to be dictated by thehealth of your relationships.
If you get to retirementwithout these relationships,
it's not going to matter howlarge your portfolio balance is.
You're not going to have themeaningful, fulfilling, joyful

(04:17):
retirement you otherwise wouldhave had had you prioritized
relationships along the way.
So hopefully you can do thiswhile you are working, but if
your work is preventing you fromdoing so, if you're not able to
find the time to invest inthose relationships, it might be
time to retire now.
The fourth reason it might betime to retire now is to
maximize your health span, notjust your lifespan.
Here's what I mean by that.

(04:38):
Let's say you're 62 years oldand you think you might live
until 92.
In fact, let's say that youcould guarantee it.
Obviously you can't, but forthe sake of this, let's
illustrate that you know thatyou have 30 years left.
So what do you do?
You say I need to max my socialsecurity so I have a strong
income source to get me to age92.
So you work and you work, andyou work from 62 to 70.
You've maxed your socialsecurity benefit, you've maxed
your 401k, whatever else youmight be doing, and you think

(05:02):
that now you have 22 years tofully enjoy that.
Well, you have 22 years of lifeleft.
In this example, that doesn'tmean you have 22 years of
healthy life left.
There's a very big differencebetween our health span and our
lifespan.
Our actual health span in theUS, on average, is age 66,
meaning age 66, that's theaverage age at which health

(05:23):
conditions chronic healthconditions sometimes prevent us
from actually doing the thingsthat we could do with a healthy
body.
So if you're working from 62 to70, that example sure, you have
22 years of life left, but youjust used up all of your health
years.
And not just that, but I wouldargue that in many cases, the
longer you continue to workassuming it's a high stress,
high demanding job that doesn'tactually bring you contentment

(05:45):
and joy you're actually burningsome of the healthspan that you
have left in a faster waybecause of the added stress,
because it's more time pushingoff prioritizing your health.
It's actually shortening yourhealthspan while simultaneously
working those years to age 70,like I'm talking about in this
example.
So understand that it's notjust lifespan that we're looking
at when it comes to designing awonderful retirement, it's

(06:07):
healthspan.
How do we make sure that, whenwe envision all we can do in
retirement, some of those thingsneed to go in the earlier years
.
Some of those things aren'tgoing to be able to be done in
your later 70s, 80s and beyond?
Very big difference betweenyour healthy retirement years
and the years where you'reliving but don't have the health
to do what you actually want todo.
And finally, the fifth reasonwhy it might be time to retire

(06:28):
now is you need to break thecycle of working for work's sake
.
I want to be clear here.
Work is not a bad thing.
In best case scenario, youcontinue to work throughout
retirement, but you do so in away that it's not taken away
from relationship, from travel,from adventure, from the things
that also bring you joy andcontentment.
Work by itself is not evil orbad.

(06:49):
Work is actually a wonderfulthing.
What you want to avoid, though,is when work isn't a good thing
in your life, when work's justadding stress, when work's
deteriorating your health, whenwork's preventing you from doing
the things you otherwise wouldbe doing.
That's what we're talking abouthere.

(07:11):
So if you are on that hamsterwheel, I've talked to so many
clients over the years of doingthis where financially they were
in a wonderful position toretire and they didn't like
their jobs.
So to me when I was younger inthis profession, it seemed
obvious well, go retire now.
But I was always confused whypeople wouldn't retire.
They kept staying on thehamster wheel.
They kept saying one more year,one more bonus, one more round
of maxing out my 401k.
And what I realized is it was abit of a hamster wheel.
Their identity had been so tiedinto what they did for work,

(07:32):
even if they didn't do it, evenif they didn't actually like
what they were doing for work.
And so the fear of retirementbecause of this loss of identity
, this loss of who I've been forthe last 30, 40 plus years,
that prevented them from takingthe step and actually moving
into retirement.
So if that's you, where you'reboth financially in a position
that you could retire but you'recontinuing to work because

(07:52):
there's that fear, so you stayon the work hamster wheel and
might be time to retire now.
Now, obviously, all five ofthese things are contingent upon
do you have the financial means, the financial resources to
support all of this?
But there's a very fine andvery delicate balance between
getting the financial side rightand not going so all in on the
financial side that you continueputting off life, you put off

(08:13):
retirement, you put off yourhealth.
That's what we want to avoid.
How do you make sure that youhave a financial strategy that
can support what you want lifeto look like, but you're using
those finances to actuallysupport life?
You're not continuing to worklonger, save more, invest more
and constantly pushing thesethings off and deferring them
for another day.
So my call to action is thisEvaluate in a very honest way

(08:35):
where you are today.
First ask are you financiallyready?
Then ask what's preventing youfrom retiring now or at the time
when you will be financiallyready?
Maybe nothing, which iswonderful, but I know a lot of
you watching.
There is something that'skeeping you tied to work and it
might not be a healthy thing.
So understanding how thesenon-financial factors, things
like health relationships,purpose, understand how that

(08:58):
plays a huge role in yourability to enjoy your retirement
years, hopefully will help topush you to take the steps
necessary to retire when itmakes sense for you.
Once again, I'm James Canole,founder of Root Financial, and

(09:19):
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.