The BEST Retirement Advice (From 909 Real Retirees)

What if the riskiest move isn’t retiring too early, but waiting so long your best years pass by? This episode unpacks the real regrets of 909 retirees and the practical steps they wish they’d taken sooner. Design purpose. Spend on what matters. Do it while health and energy are on your side.

Beat the “one more year” trap. Working longer can look safer on a spreadsheet, but life isn’t a spreadsheet. Learn how to prototype purpose before day one, shift your identity from saver to spender without guilt, and choose a retirement location that supports daily joy and long-term care needs.

Avoid the hidden tax hazards that derail cash flow. Understand RMDs, Social Security taxation/stacking, and Medicare IRMAA. Use Roth conversions and bracket smoothing to lower lifetime taxes and protect your spending plan.

Put relationships ahead of returns. Money gives options. Connection gives meaning. With simple guardrails and a clear plan, you can spend earlier and more intentionally on experiences, travel, and family, instead of hoarding for a “someday” that never comes.

Ready to align your retirement plan with the life you actually want to live? Listen as James gives you the framework and the nudge to start now.

-

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!

Episode Transcript

SPEAKER_00 (00:00):
If you think your biggest regret in retirement is
going to be spending too much,then I have news for you in
today's video.
We reached out to thousands ofpeople to collect their
responses about their biggestretirement regrets, and we heard
back with wonderful feedbackfrom 909 people.
Some of the regrets that thesepeople share have to do with
finances, but many of them didnot.
It has to do with purpose, howyou spend your time, unexpected

(00:22):
costs, things of that nature.
And in today's video, I'm goingto share with you the real
feedback we heard from 909people, the regrets they have,
and the advice they would havegiven to their younger selves so
that you can take this and applyit as you prepare for your
retirement.
So here's the advice we receivefrom people who have actually
done it, who have actuallyretired.
The first piece is that workinglonger is not necessarily safer.

(00:43):
How many of us have been caughtup in that?
We run projections.
We see here's the impact of onemore year of work, maxing out my
401k, one more year, paying intoSocial Security, one more year.
And on paper, it has tremendousbenefits.
We see what that does to ourlong-term financial projections.
But here's the thing that moneyis pointless if it's not helping
us fund the type of life we wantto fund.
In that life that we want tofund, so much of it has the

(01:06):
potential to pass us by if we'renot able to appreciate the
opportunity in front of us.
In other words, I've seen fartoo many people work too long
trying to maximize the financialside of things that life has
passed them by.
This was a common regret peopleshared, and therefore a common
piece of advice is workinglonger isn't necessarily safer.
Sure, there's positive financialbenefits to it, but are you

(01:27):
missing out on life by doing so?
Are you missing out on youryouth, your health, your vigor,
your ability to do the thingsyou actually want to do in
retirement because you keeppushing retirement off?
Some direct quotes we heard whenwe surveyed people is I wish I
had retired earlier.
I wish I'd spent more money ontravel sooner.
I wish I hadn't cut back myspending so much due to fear.

(01:49):
Now, this is where a goodfinancial plan comes into place.
You do need to make sure you'renot overspending, because that
too would be a regret.
But so many people are driven byfear in their planning.
And they just thought that if Ispend less or work longer or
save more, that's magicallygonna make my retirement that
much better.
That could not be further fromthe truth.
Work as long as you need to workto prepare for what you need to

(02:09):
do, but do not put offretirement if you're only doing
that because you feel like nextyear you'll feel more
comfortable.
The following year you'll bemore ready.
There's not gonna be a magicfeeling.
And if you wait too long, toomuch of your greatest retirement
years might pass you by.
The second piece of advice thatwe heard from these people,
these real retirees, wascultivate your purpose ahead of
time.

(02:30):
Don't just think that I'm gonnaretire and life's magically
going to turn into a vacation.
I'm gonna travel, I'm gonnagolf, I'm gonna sleep in.
That might be fine for someperiod of time.
And that might even be fine tocontinue doing on an ongoing
basis if you also have things ofpurpose mixed into that.

But here's the thing (02:45):
you're not just gonna magically stumble in
to your purpose.
In the same way, you don'tstumble into maintaining your
health, you don't stumble in tosaving well, you don't stumble
in to doing good things onpurpose.
You're not gonna stumble intofinding that purpose.
So think about it, work throughit, try different things.
What is it that's truly gonnagive you that sense of joy and

(03:05):
satisfaction throughout yourretirement?
Retirement has the potential tobe so incredibly good for so
many people, but not if we'remissing that purpose.
What do we want to do?
Who do we want to spend timewith?
What do we want to prioritize?
What are the things we can dotoday that 20 years from now
we'll look back upon and saythat led and contributed to a
meaningful, joy-filledretirement?

(03:26):
Think about that beforeretiring.
The challenge so many peopleshared is they were so focused
on work and theirresponsibilities and saving and
preparing and getting ready toretire, they forgot about what
they actually wanted to be whenthey retired.
In surveying retirees, they saidthis led to feelings of
loneliness, of boredom.
It was hard to transition frombeing a saver and a spender
because they didn't understandwhat was next.

(03:47):
So, yes, financially prepare forretirement, but also prepare
mentally.
What do you want to do and whodo you want to be?
And how can you start thinkingabout that in the same way you
think about how much you need tohave in your 401k, when you're
gonna collect Social Security,what Roth conversions you're
gonna implement along the way.
If you're not doing both ofthese things, your retirement is
not gonna be as joyful andmeaningful as it otherwise could

(04:07):
have been.
The third piece of advice thatretirees gave in this survey is
that location matters.
Location of where you actuallyretire to.
So it doesn't mean you need tomove.
You don't need to be somewhereelse when you retire.
But here's what they meant bylocation.
Yes, part of it was weatherrelated.
Some people wanted to avoidextreme hot or avoid extreme
cold.
Maybe they were in a certainlocation because work demanded
of it.

(04:27):
And now that they're retired,they can move elsewhere.
But what about location of thethings that matters?
What do you want to do when youretire?
Do you want to be near the lake?
Do you want to be near an ocean?
Do you want to be near themountains?
Do you want to be near yourfamily, your friends, hospitals,
healthcare networks?
What are the things thatactually matter to you?
And how do you choose a locationin retirement where you have
access to all of that?
Think about this especially asyou age.

(04:49):
You don't want to just thinkthrough the terms of where can I
get the best medical care.
That is going to be anincreasing consideration.
So can you choose a place whereyou're close to the people you
love, you're close to the thingsyou love doing, and you're close
to the type of care that youmight need, especially as you
age, the place that you retireto, that location matters a lot.
And we heard that directly frompeople who retired.

(05:10):
The fourth piece of advice waswatch out for tax spikes.
So often people just assumethey're going to be in a lower
tax bracket in retirement, andthose assumptions are confirmed
their first couple of years ofretirement.
Maybe they retire in their 60s.
In the first few years, theirtax bracket isn't all that high.
But they don't do anyforward-looking planning.
And then one day they wake upand required minimum
distributions kick in.

(05:31):
And that's on top of theirsocial security benefit.
And that's on top of their otherincome sources.
And all of a sudden, thesepeople that were in a lower tax
bracket get whacked when they'reforced to start taking money out
of their accounts.
So watch out for the impact ofrequired minimum distributions.
Another related thing to this isIrma surcharges.
People are taking money out.
They see, okay, I'm taking thisfrom my IRA or my Roth IRA, my

(05:53):
brokerage account, whatever itis.
And then they get a bill fromMedicare or their premiums go
up.
And they say, why are mypremiums going up for Medicare?
It's because their IRMAsurcharges went up.
Their modified adjusted grossincome maybe stayed under
certain thresholds for federalincome taxes or state income
taxes, but there's this otherthing called IRMA, Medicare
surcharges that people also haveto be aware of.

(06:15):
And your income also impactsthat.
So be aware of all the potentialtypes of taxes that you might
pay in retirement and make surethat you plan accordingly.
Some of the specific things weheard on the survey are people
saying, I wish I'd used the RothIRA earlier.
I wish I hadn't put too muchinto my traditional 401k.
I was very surprised at theamount of taxes that I owed.
I was very surprised by the RMDimpact.

(06:37):
So be aware of this.
When you are retired, if youdon't have a tax strategy to go
along with your income strategyand overall retirement plan, you
have some missing pieces.
You have some gaps.
So make sure that you'replanning for those surprise tax
hikes.
The fifth piece of advice thatthese retirees gave was
prioritize relationships overspreadsheets.
There is this overwhelmingsentiment that feeling that more

(06:59):
money would magically lead to ahappier retirement would
magically solve any potentialproblems people might have.
So it's easier.
Put your head down, grind, work,save, invest.
One day I'll wake up andeverything will just work.
Everything will just make sense.
But that's not the case.
The things that matter most havenothing to do with money.
And to put it bluntly, it's yourrelationships.

(07:20):
The quality of your retirementis largely going to be driven by
the quality of yourrelationships.
So if your only priority isgetting the financial component
of things dialed in forretirement, yes, that's
important, but you're missingout on the bigger picture.
I can't tell you how many peopleI've worked with that have had
the perfect financial strategy.
They have more than enoughincome to meet their needs.

(07:40):
They've implemented the taxstrategies to save lots of money
over retirement, the perfectinsurance is the perfect estate
plan.
Everything was good except forthe relationships, except for
things that mattered.
So don't fall into that trap.
The thing about money is it's sotangible, it's so easy to see,
it's so easy to keep track ofand have a scorecard for that
you can optimize that.
And it feels good.

(08:01):
There's an immediate feedbackloop that you are doing better.
That's not the case withrelationships.
Relationships can start toquietly drift.
And if you're not aware of it,one day you wake up and realize
that you and your spouse aredistant.
You and your old friends don'tmaybe talk as much anymore.
You and your children don't havethe type of relationship you'd
want to have.
So yes, prepare financially, butalso yes, prepare relationally,

(08:23):
because those relationships aregonna be a crucial part of your
retirement plan.
Then finally, the last piece ofadvice that I wanted to share
from this survey is people wishthey had spent more.
I know this ties in a little bitto the first piece of advice of
don't wait too long to retire,but this part is don't wait too
long to spend.
Even once you retire doesn'tmean you're automatically going
to feel permission or feel safeor feel like it's okay to

(08:46):
actually start spending money.
Now, this feeling that peoplehave is very much backed up by
data, very much backed up byresearch.
In fact, research shows thatyou're far more likely, assuming
you only spend 4% of yourportfolio, you're far more
likely to have much more moneyat the end of your retirement
than you do today, at thebeginning of your retirement.
The goal of life isn't to carrythat money with us to the grave.

(09:07):
The goal of life isn't to keepgrowing that portfolio over the
course of our lifetime.
That portfolio is simply a toolthat allows us to do the things
that we want to do.
So spend freely, spend wisely,spend prudently, but identify
those things you actually wantto spend money on.
What are the things you want tospend your time doing?
What does matter most to you?
What does your vision for aperfect life look like?

(09:29):
And how do we use this portfolioto support all that?
The piece though that tripspeople up is very difficult to
do that.
It's very difficult to go from alifetime of saving money, maxing
my 401k, putting money intoIRAs, and also not to pull that
money out of my account.
Not to pull that money out of myaccount even when the market's
going down.
That doesn't feel good to a lotof people.

(09:50):
So it's a habit that must bedeveloped, but it's a habit that
absolutely is crucial to yourability to actually live the
type of retirement that you wantto live.
So don't wait too long to spend.
It can be a difficult shift.
And yes, have guardrails inplace.
Make sure you're notoverspending, but I see far too
many people who underspendbecause of fear.
But if you have the plan, if youhave the guidance, spending

(10:13):
money is one of the best thingsthat you can do to create the
retirement you want to live.
The overwhelming takeaway as wewrap up today, I saw very, very
few responses of people saying,I just wish I had more money.
The overwhelming sentiment thatthese retirees shared is they
wish they started moving onthese things sooner.
Prioritizing relationshipssooner, prioritizing retirement

(10:34):
sooner, prioritize spendingsooner.
Don't let this be a one-daything.
Make this be a thing that youfocus on right now.
So the best time to take actionon this is today.
Whether you're 40, you're 50,you're 60, you're 70, it does
not matter.
The best thing you can do foryour future is to start this
planning today, start thisintentionality today.
If you need help with that, wecan help.

(10:56):
Root Financial, this is what wedo all day, every day.
We have a team of advisorshelping people with just this.
You can reach out to us.
Link is in the show notes below.
But regardless of who you'reworking with or not working
with, take these principles toheart.
Start doing these things todayto create a better retirement
for you, for your family, andfor those around you.