51: 10 Tips for Your First Day of Retirement

“Don’t retire to recliner. Your best days are ahead.”

In this episode of Up Your Average, Keith and Doug give salient advice on how to make retirement the best years of your life.

In this episode, you’ll learn:
➡️ The best questions to ask the first day you retire
➡️ Why you should still find work to do when you retire
➡️ How to manage your investment money to last 30+ years

Episode Transcript

Doug (00:00):
We had a client, and this was so sad. They had a ton of

(00:03):
money. And when one of themdied, the surviving spouse said,
man, Doug, we we could have goneto Hawaii. So she wanted to go
to Hawaii. They had theresources to do it, but he never
knew the depth of her wanting togo there with him.
And so do that. If you candefine whatever it is that would

(00:24):
be a successful retirement, godo it.

Caleb (00:27):
Welcome to the Up Your Average podcast, where Keith and
Doug give no nonsense advice tolevel up your life. So buckle up
and listen closely to Up YourAverage.

Keith (00:47):
Good morning, Doug.

Doug (00:48):
What's up? What's up? What's up?

Keith (00:50):
It's a beautiful day in the neighborhood. I am excited
about the fall time.

Doug (00:55):
Yeah, I am too. Well, I'm just excited about life.

Keith (00:58):
Me too.

Doug (00:59):
Life's good. I mean, when you live in Indiana, you have a
hard four seasons like fall islegitimately good. So is summer.

Keith (01:10):
I have a favorite thing in the woods during the fall,
and that is picking up a walnutand chucking it at something or
somebody.

Doug (01:22):
Is At somebody?

Keith (01:24):
I mean, generally not at somebody. In my in my younger
days, we did have all thatfight. So I have, you know, I
have to resist that temptationas an old guy.

Doug (01:36):
We did our annual fall thing last week. We had a lot of
fun. We went and picked apples.One of our boys, me, Caroline,
and my father-in-law, Larry, whoturns 80 coming Happy birthday.
Thanks.
Yeah, go Larry. And we we pickedlike seven, eight, five gallon
buckets full of apples. AndCaroline's been making

(01:56):
applesauce. And it's just abeautiful thing. Fall is a
beautiful thing.
Life is a beautiful thing.

Keith (02:02):
I know I'm going to sound like a just a kid who fell off
the apple cart is I celebratedRosh Hashanah.

Doug (02:14):
Yeah. Yeah. I know. I know you did. You sent me pictures of
your celebrations.

Keith (02:18):
Yes. And it was in honor of our friend Stan, and it is
the celebration of the JewishNew Year. And with that, it was
tied back to the apples. It wasapples with honey on it. And
what I learned about theircelebration is that it's it's
it's a way to look for apleasant and sweet year.

Doug (02:37):
Yeah, that's so cool.

Keith (02:39):
That was one of my highlights that I had fun with
this week. So that was good.

Doug (02:43):
Yeah, right on.

Keith (02:44):
Next week, I have a friend retiring and I thought we
might offer some advice and doit in a anonymous way with a
hypothetical character by thename of Paul Williams.

Doug (03:01):
Alright, I have a picture in my mind of who Paul Williams
is.

Keith (03:04):
Paul Williams is, we're going to call him 60. Okay. What
would his wife be named? Whatwould Paul who would Paul be
married to? Bridget.
Bridget Williams is 60 as well.I don't know any Bridget's from
my age, but I guess there wouldbe a Bridget. Bridget Bardo,
maybe. Bridget is 60 and sheretired a couple years ago. And

(03:29):
so I thought we could do threethings before Mr.
Paul Williams in celebration ofhis October 1 retirement. One of
the things is normally whenwe've I would say it's fair to
say we've helped hundreds ofpeople retire from Gimbal
Financial over the years, and alot of the work we do is prior

(03:50):
to the October 1 time where wesit down, talk through the
numbers, talk through the risks,talk through the possibilities.
And so this is the decision ismade. So what do we do now? And
with that, let's jump into ifPaul Williams was sitting here
right now, Doug, and you wantedto offer him some caution as he

(04:14):
goes into retirement, what wouldbe a couple, two or three pieces
of cautionary insight you mightoffer him today?

Doug (04:23):
Yeah. Well, one of the things that comes to mind is is
just retirement is is such anemotional decision. There's a
lot of emotions that go into it.And I'd want to know, like, how
did he get here? How did he getto this place?
Had he always been dreaming ofage 60? Or did he get ticked off

(04:44):
at an email that was sent to himand then decided today is my day
that I'm retiring? And so 'dwant a little bit of the
backstory. But, the main reasonI'd be asking those questions is
to figure out, hey, Paul, whatare you retiring to? You know, I

(05:05):
hear you about what it's beenlike, but what are you retiring
to?
What are the things that aregoing to keep you alive,
climbing out of bed in themorning, and focused on a
purpose filled life?

Keith (05:20):
Boy, that's a good word. I was visiting one of the people
that trained me in Louisvilleearlier this week. He is, if my
memory serves me, 93. So had heretired at 60, that's thirty
three years.

Doug (05:38):
And that's what you have to plan for.

Keith (05:39):
You have to plan for thirty years. And while I was
sitting there talking to him,Caleb was sitting next to him,
and over the top of his head, Isaw somebody walk into the
restaurant, and I heard somebodyannounce that fella's name. I'm
in Louisville. I don't knowanybody in Louisville. And then
I asked this fella, I said, thatguy's name is this, Is that

(06:03):
would that guy have trained methirty five, forty years ago?
And it was.

Doug (06:07):
So

Keith (06:07):
there were two people. This guy was probably a little
younger than our our friends, sohe was probably he probably if
he had left at 30, he or at 60,he probably had been at least
twenty five years retired. Andso that that retirement's a long
time.

Doug (06:24):
Yeah. You know, and and another concern would be, hey,
are you willing to be thinkinglong term? Or are you are you
making an in the momentdecision? And so from an
investing standpoint, are youare you willing to understand
that you're going to be a longterm investor, even though
you're hanging up your earningsyears.

Keith (06:45):
Well, and when we talk about that, I don't know if
we've said it on up your averagebefore. But if you just think
back ten years and flip thecalendar back ten years, what's
happened in the markets in tenyears? Yeah. You go back twenty
years, what's happened in themarket? We used to be able to,
you know, say 09/11 was in that,who could predict?

(07:07):
Now you gotta go back 25 for09/11, basically. But if you
then flip the calendar forward,you have no idea what's gonna
happen in your thirty plus yearsof retirement.

Doug (07:19):
What do you think? What are some of the things that come
to your mind?

Keith (07:22):
Well, cautionary wise, I wrote down a couple prime things
that I would caution you to do.One is to get physical. Like,
don't retire to a recliner. Ithink that's really a Did

Doug (07:35):
you say retire to recliner? Yeah. Man, can you,
like, trademark that or

Keith (07:40):
something? That's that's pretty good. I just have a I
have a mental picture of whatthat looks like.

Doug (07:46):
Yeah. I'm picturing like, you could sell that to La Z Boy.
Yeah.

Keith (07:51):
Like the one we just put it in the basement of Gimbal.
And and so get physical, and Ialso think get a physical
because there's some decisionsyou'll have to make in your
sixties that has to do with yourhealth. Like when do I turn the
switch on with Social Security?Well, if there's a health

(08:11):
limitation, I would say probablyyou want to turn it on sooner
than later to get what you havecoming to you. But so the get
physical and get a physicalwould be some cautionary things.
And then secondly, I would sayupdate your estate documents
because you may not have them.Like, a lot of people don't have
them. So today is the day to getthem. And then secondarily, I

(08:37):
would instruct the role bearers.I would not just get the
documents and have them sittingon a shelf somewhere, but the
role bearers that you're goingto need in retirement might be
your executor, your trustee,your healthcare power of
attorney is the one that I'mreally thinking about, because

(08:59):
my experience has said mostpeople, as they get more years
under their retirement days, aremore hard headed and less likely
to listen to feedback when theymight need it most.
So if you need to quit driving,which you don't add sixty, then
maybe seventy five, and thoseyears will go fast, to sit down

(09:21):
with the role bearers in yourdocuments and give them
permission to live out thoseroles, I think is some
cautionary advice I'd offer.

Doug (09:29):
Yeah, that's that's all good. I think another one that I
would really focus on whatwhat's her friend's name?
Bridgette I would I would have areal honest conversation. I'd
say, I'd say, Hey, Paul, haveyou and Bridget had a real deal
crystal clear conversation onyour hopes, your visions, and

(09:52):
your fears about retirement.Like what, what happens when all
of a sudden you're at home orshe's at home, the income spigot
is not turned on yet.
I mean, you haven't flipped onsocial security. You're not 62
yet. You're not 67 yet. You'renot 70 yet. And so, you know,
what what are your visions, youryour your fears?

(10:13):
How are you going to handlegiving money to one of your
kids? You know, when one of youwants to do it, and the other
one doesn't want to do it? Imean, what what would that look
like? And so I I think thesediscussions are all centered
around, again, the the kind ofthe the the more emotional sides
of of money type decisions. Andvery few couples talk about

(10:36):
anything of importance anyway.
I know it's hard. I'm marriedtoo. But talking about money and
retirement, that's one that youreally have to spell out
together.

Keith (10:49):
I would and I think right in that same lane, Doug, is at
60, talking about your healthwith one another is probably
less emotional than at 75. Soprobably right now is the time
for the two of you to have a cupof coffee and say, what are we
going do when one of us getssick? How are we gonna move
forward with that? And I knownobody wants to have that

(11:12):
conversation, but I don't if ifyou don't have it, you probably
aren't going to have it. Like,it's just gonna be one of those
things that's in the room, thatbig old elephant that nobody
wants to talk about.
And while you're healthy, whileyou're both healthy, let's just
talk about it today, put somesome guidelines out there and
how are we gonna bring you know,if one of our kids is the health

(11:33):
care power of attorney, how arewe gonna bring them into the
process so that they might beinvolved in helping whichever
one isn't sick first, right?

Doug (11:43):
And that's a great segue into, hey, the conversation of
one of us is probably going tolive ten to fifteen years after
the other one.

Keith (11:52):
Most likely. That's been our experience.

Doug (11:54):
So what does that look like for us? You know, what type
of home do we want to be in?When do we want to make that
move? When do we want to clearout the attic and actually move
into a place that one of uscould live in for those ten or
fifteen years? Boy, that's It'sgetting maybe simplifying
things.

Keith (12:12):
Yeah. So those cautionary things, of those things are fun
to even jump into, but I thinkit's a gift to everybody
involved if you're willing to dothat. Let's jump over to just
straight up advice. So Paul issitting there, and he didn't
really ask for our advice, butwe're going to give it to him.
So so so what is the first?
Is that Wednesday? So that's hisfirst day. So we'll say

(12:36):
Thursday. What's what's youradvice for him Thursday going
forward?

Doug (12:39):
Well, my my first advice would be, hey, Paul, you you
picked a pretty good time toretire. I think a lot of people
think I'm going to work untilyear end. And that's cool if you
are retiring and your residenceis in Miami. But if your
residence is in Carmel, Indiana,January 1 is a lousy time to

(13:02):
retire. So way to go, Paul, Iwould just encourage you to just
enjoy a couple of weeks of justsome downtime.
Don't don't have anythingplanned. Just enjoy a couple
weeks of downtime.

Keith (13:16):
That fits in with one of my straight up pieces of advice
is sometimes the ramping up forretirement, there's a lot of
moving parts. And our friendMark Minervini brought in, I
don't even know if you werethere, a trainer to teach us how
to box breathe. And boxbreathing is basically breathing
in four seconds, holding it fourseconds, and breathing out. And

(13:38):
the process of that is to relaxyour body, and probably your
body's been stressed out alittle bit coming into
retirement. Oh, man.
You don't necessarily have tobox breathe, but I wrote down
just breathe.

Doug (13:50):
Like I get all worked up if I leave Gimbal for a week.
I'm like ramping up to leaveGimbal for a week. Do you get
that leg? And can you imagine ifyou're trying to finish like
with as much integrity and ontop as possible? That's a lot of
pressure.

Keith (14:04):
Right. It I would guess it's gonna take you six months
to even know what happened.Like, in six months, I think
your body is gonna recognize,wow, I had a lot more stress on
me than I thought. So boxbreathing, if you want to give
it a shot, you can Google it andthey'll tell you how to do it.
Here's a key piece of advice.
This is I think it's safe to sayI know about retirement, even

(14:28):
though I haven't done it likemost people. I defined it as
doing what I want to do back in1996, and I've lived that kind
of retirement. I do what I wantto do, not arrogantly, but I've
gained control of my time. Andthere's not a lot I do anymore
than I'm not willing to just sayI want to do that. But here's

(14:48):
what I would encourage you,having walked through retirement
with many people, create yourown news.
We don't have local newspapersso much anymore that have like
what's going on in thecommunity. You have some local
TV news, but a lot of things inthe news are sent to you from

(15:10):
some talking heads in some placethat don't really know what's
going on. And if you create yourown news, you don't have to
watch the news anymore. Andcreating your own news might be,
what am I going to do in mycommunity to make a difference?
And I think that piece of advicewill give you a more uplifted
mindset for your entireretirement than watching news.

Doug (15:32):
Yeah, I think that's a great call. I think quick little
check ins are, are good to dotoo. That could be with your
kids, that could be with yourfinancial advisor, but, but not
like long, you know, two hourcheck ins, just quick little
check ins with each other sothat you're actually staying
current and staying on people'sradar. Because it'd be easy to

(15:54):
just drop off and do your ownthing.

Keith (15:56):
Right. Right. And and with with that idea of creating
your own news, I think how youcreate your own news is expand
your friendship. Because really,only I don't know you know, we
could worry about what's goingon in Africa today or whatever.
But if I expand my friendships,and then they become my news and

(16:20):
they become my curiosity, thenreally interesting things will
happen.

Doug (16:24):
Man, maybe just watch a couple episodes of Up Your
Average the last few weeks.That's what they should do their
first week of retirement. Imean, we've got some good expand
your world view stuff out there.

Keith (16:35):
They should click like and share. That's what we say.
But one of our friends, Gene, hewas sharing with me and kind of
our my prep work for this thathe has volunteered in retirement
and he's golf course ranger. Andin that, it's a repetitive type

(16:55):
of volunteering thing. So with avolunteering event, repetition
will expand your friendshipsbecause you're going to see the
same people over and over again.
And one of the things that youmight not consider as you're
going into retirement thatyou're unplugging from friends
that you sit in the same roomwith every day. And so the idea
of volunteering and adding newfriendships may not if you're an

(17:19):
introvert like me, it may not beeasy to add friendships, but if
you volunteer someplace, you'regoing get a repetition of new
people back in your life.

Doug (17:27):
Yeah. I think another piece of advice that I would
give as a financial advisor isI'd want to talk about how do
you want to be paid in yourretirement? Like, you do you do
you want a paycheck to come inon a monthly basis? Do you want
a paycheck to go annually? Or doyou just want to, when you need
money, call?

(17:47):
And in different strokes fordifferent folks. I mean, you all
have unique strengths. And so Iwant to figure out about Paul
and Bridget and just how they'veoperated in the past. If they
like a monthly paycheck comingin, they can do that. And I
think it just needs to bereinforced that you've got
options.

(18:07):
You don't have to do it likeyour friend did it or like your
dad did it. You can you cancreate your own solutions.

Keith (18:14):
Absolutely. Absolutely. And and I think getting into my
my final thing I threw out toyou, Doug, was what challenges
would you offer to them? Howwould you challenge them to jump
into their future at this point?And one of them goes along.
One of them I had written downwith that idea was I wrote down

(18:35):
inflation is real. When I firstgot in the investment business
in the eighties, they justpounded that into our heads as
young stockbrokers that you needto let people know inflation is
real. That was coming out of theseventies and eighties where we
had like hyperinflation and soyour money would just vaporize

(18:55):
really, really quickly. And Istill hype on that with you
guys. I send you the anchor outonce a year with about 100
stamps on there to point out howyour money is shrinking.
It's not the retailers, it's notyour grocery, it's your
government that's shrinking yourmoney. And if inflation is real,
how am I going into retirementgoing to address that? And not

(19:19):
many financial advisors wouldsay this, but this is what I'm
going to tell you. Spend somemoney today. Yeah.
Because if you want to go toEurope, it's not going to get
cheaper twenty years from now.So why not go do it today while
you're spending current dollarson something that's going to
cost a lot more down the road?Plus you're healthy. Yeah. And
and so spend some money today tooffset inflation.

(19:41):
That's kind of a you're probablynot gonna hear that from a lot
of financial advisers, but it'sa way to chase your dreams today
while you're healthy and do itwith similar dollars to the cost
of things.

Doug (19:51):
I think just again, defining what a successful
retirement looks like for forBridget, ask her, hey, what what
does a successful retirementlook like to you? And then for
Paul, for Paul to define ithimself, like we had a client,
and this was so sad, they had aton of money. And when one of
them died, the surviving spousesaid, Man, Doug, we could have

(20:14):
gone to Hawaii. That's what shesaid, we could have gone to
Hawaii. So she wanted to go toHawaii.
They had the resources to do it.But he never knew the depth of
her wanting to go there withhim. And so do that. If you can
if you can define whatever it isthat would be a successful
retirement, go do it.

Keith (20:36):
That may have been one of my that conversation may have
been one of my defining momentsas a financial advisor. Like,
there there was legitimate angerin that conversation, and it was
kind of heartbreaking-

Doug (20:47):
It was.

Keith (20:48):
To realize that money the money in both of them have
subsequently passed away. Themoney there's a proverb that
says you don't know who willinherit your money. And that's
kind of what happens is youdon't know what's going to
happen. And I think along thelines also, Doug, with the
inflation is to not sellyourself short. Like the gig

(21:10):
economy is alive and well.
And if you need to you probablyneed to expand your social
network, whether you think it ornot. Having watched this long
enough, you probably do. It'sgoing to get skinnier and
skinnier over time. And so onethe pieces of advice I got from
someone is that they decidedthey were gonna just do one gig,

(21:32):
like one consulting thing, andbackfill that in there. It does
a number of things.
That money will help you withinflationary issues. It'll keep
you relevant. It'll and it'lladd to the broadening of your
friendships.

Doug (21:46):
Yeah, I mean, I can think of a couple really strong,
awesome, successful retirementsthat we've been able to have
relationships with here atGimbal. And both of these guys
went back to work doingsomething that they just really
liked. And it might have broughtin $15,000 18,000 extra a year.

(22:06):
I'm not talking about, you know,slaving over that the desk or
the keyboard. But those littleadd ons, the money was great,
the 15 to 18 was great.
But really, it was just thepurpose factor, and doing what
they were cut out to do.

Keith (22:22):
And we talked, I think in a recent Up Your Average about
expanding your world, but alsowhat is your worldview. And if
you've not taken time to thinkabout purpose, I would really
encourage you to go find a shadetree or go for a walk in the
woods and explore that idea.Because I think the more

(22:42):
purposeful you can live today,tomorrow, and the next day,
whether you're Caleb's age oryou're Paul retiring at 60, a
purposeful life is just one ofthe most meaningful things there
is.

Doug (22:55):
Yeah. Just don't sit under a walnut tree.

Keith (22:58):
Or sit near it because you might get clocked.

Doug (23:03):
Here

Keith (23:04):
here's you had mentioned look at some up your averages. I
I like they're available on mostof the podcasting things, but I
like the YouTube versions ofthem.

Doug (23:15):
It's easier to find them on YouTube, I think.

Keith (23:18):
Right. And they're all numbered and sequential out
there if you look properly. Thatwasn't good. So what I would say
is watch Up Your Average number16. Which one's that one?
That's with Mitch Anthony.

Doug (23:34):
Oh, yeah. Tell us who Mitch Anthony is.

Keith (23:37):
Mitch Anthony wrote a book called The New Retire
Mentality. Here's a version ofit right here. Highly recommend
it. Mitch is a great man. He's agreat friend of Gimbal Financial
and has been for many, manyyears.
And and so that interview wasjust us talking to him about

(23:58):
retirement and mindsets that youmight want to have. And so if
you are a reader and you're inretirement, this is a great
read. It's a good one to givesomebody who is retiring. But
yeah, watch that video.

Doug (24:09):
Think of Mitch Anthony from time to time. He's like,
you know, like Jerry Maguirehad, his mentor, Dicky Fox, who
would like come into play andwith a quote or with something
great to say. And Mitch Anthony,he he just like Keith's mission,
he thinks differently aboutretirement.

Keith (24:26):
And we'll probably have him back on here before long,
it's worth your time to do that.Final thing I wrote down for the
challenge to those of you whoare retiring or are retired is
to get and we have these littleidea cards. So if you're around
Gimbal, we'll give you one. Andwrite 10 ideas on it. Ten's a

(24:48):
big number, and most peoplewon't do that.
You probably won't do it. Somaybe do three ideas. And those
ideas are what are three to 10things that you know that
somebody else should know.That's a suggestion for you to
take and put legs on today.Because if you have three to 10

(25:12):
things that you know thatsomebody else should know, then
that gives you a bridge tosomebody younger than you to
help them see some ideas thatmaybe they haven't seen yet.
And I think your wisdom thatyou've built up, Paul, to age 60
shouldn't stop just because youstopped working. You should pass
that on to somebody who reallywould benefit from it.

Doug (25:34):
Yeah. And you know, one of one of my friends, he struggled
with alcoholism. And I asked himonce I said, Hey, have you ever
figured out like, the painpoint? What causes you

Keith (25:47):
to

Doug (25:47):
drink? And we were friends enough where I could ask him
that and him not punch me. Andhe said to me, Yeah, I think I
have. He says, I get these thesethoughts that my best days are
behind me, that they were theones in my childhood, with my
family. And Keith, one of thethings that you you say quite

(26:09):
often is your your best days areahead of you.
And so I would encourage you,I'd challenge Paul and Bridget.
And I'd challenge him with thisthought is, hey, are your best
days in front of you? Could yourbest days in front of you? Could
that actually be true? And thenwhat would that look like?

Keith (26:28):
I am really grateful with that idea, Doug, from Mitch and
his writings, because Idiscovered this book shortly
after I had redefined retirementfor myself. And we've said
several times on that I'm kindof cynical about a lot of things
in life. And just as a youngman, I feel humbled that God
gave me the wisdom to recognizethe financial services industry

(26:52):
was, I don't know if you'd usethe word brainwashing, but
they're propagating ideas thatdevalued work. And I think
Gimbal has long believed, Ithink because of Jim Pingson's
influence, he said it succinctlythat work is honorable. And so a
lot of people find their valuein their work.

(27:13):
But what I would tell you isthat quitting working, I. E.
Retirement, is not a validpursuit in life. Like if that's
your goal in life, if that'syour destination, you're leaving
so much of who you are on thetable. I think everybody at

(27:34):
Gimbal views every one of you asinvaluable, like unbelievably
valuable.
And the value isn't what you dofor work, it's who you are and
your inner person. And the moreyou can kind of connect that
going towards your ultimateretirement, I think is going to
bring unbelievable fulfillmentyour way.

Doug (27:53):
Yeah, congratulations to Paul. Congratulations, I think
to Bridget. Paul's going to bearound more.

Keith (28:00):
Yeah, I don't know what to tell you, Bridget, when he's
when he's walking around there.We we are just humbled that you
guys would spend some time withus on, this this morning, and
hopefully, it's brought somewisdom your way. And if any of
you that are joining us areretired, we'd appreciate any
other feedback you want to emailus or shoot our way. Your

(28:20):
weekend. Again, thanks forjoining us today.