November 22, 2025 • 39 mins
When your children launch or your career ends, a strange silence can set in—and with it, the big question: What’s Next?
In this inspiring episode, Jack Calhoun, founder of Encore Career Lab, shares a hopeful, practical path from drifting to purposeful direction. He discusses how many of us face an identity crunch when titles no longer define us—and how to use agency, values, and curiosity to craft a second act that truly fits.
Jack unpacks the paradox of choice—why having too many options can stall momentum—and offers a straightforward antidote: start with your why and non-negotiables, identify your caring audience, and run small, low-risk experiments. He emphasizes that purpose often follows action, not the other way around, and shows how both career-related and unrelated paths can thrive if your heart is in it.
This conversation challenges outdated retirement scripts, reframing work as a fulfilling, energizing part of life’s ongoing journey. Expect honest talk about fear, ego, and indecision, along with tactical advice on surfacing your “wisdom fingerprint,” setting boundaries, and testing new ideas without risking everything.
Key takeaways:
- The rise of entrepreneurship among ages 55-64
- Identity enmeshment with career and parenting
- Finding purpose through purposeful action
- Defining your core values and non-negotiables first
Jack Calhoun Bio
Jack J. Calhoun is the founder of Encore Career Lab and a seasoned entrepreneur with over two decades of experience managing a wealth management firm. After selling his business, Jack faced his own post-retirement questions about purpose and fulfillment, inspiring him to help others navigate similar transitions. He specializes in guiding high achievers—particularly those aged 50 and above—toward designing meaningful second careers that blend passion, impact, and income. Through his insights and frameworks, Jack empowers professionals to turn uncertainty into opportunity and create purpose-driven encore careers that enrich their lives well beyond traditional retirement.
Find Jack Online: LinkedIn, Website
BECOME A VIP SUBSCRIBER (Join Today!)
- Bonus Content for Subscribers Only
- Episode Shoutouts
- Thank You Emails
- Private Meet & Greets via Zoom
- + More
ENJOY THE SHOW?
Don’t miss an episode, subscribe via Apple Podcasts or follow on Spotify and many more.
Review us on Love the Podcast, Apple Podcasts, or Spotify -- reviews and ratings help others find us and we’d appreciate your support greatly.
LOVE THE SHOW?
Get THIS EMPTY NEST LIFE swag
CONNECT WITH JAY
Email, LinkedIn, Instagram, TikTok
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_03 (00:00):
We have two things that we would have really dearly
loved to have had more of whenwe were younger, which is agency
and autonomy.
And that's the ability to decidewhat we want to do and the
capability to make it happen.
And so we need to find thingsthat are going to align with our
values and are non-negotiables.
(00:20):
I think that's what's importantis to get clarity about that
ahead of time so we don't spinour wheels and stuff that
ultimately is just not going tobe the right direction for us.
SPEAKER_00 (00:28):
Welcome to this Empty Nest Life, the podcast
dedicated to helping you embracethis transformative season with
purpose, passion, and joy.
In each episode, we explorestories, strategies, and
insights to help turn your emptynest into an exciting new
chapter.
Whether you're redefining youridentity, pursuing new passions,
or finding peace in the pause,you're in the right place.
Here's your host, the Empty Nestcoach, Jay Ramsden.
SPEAKER_01 (00:50):
Hey there, my emptiness friends.
There are so many possibilitiesin our emptiness life to
consider (00:56):
downsizing, moving, second careers, maybe even
retirement.
But here's something I learnedthat just might pique your
interest if you've ever thought,hey, I have an idea for a
business.
Right now, there's a surge inAmericans aged 55 to 64 leading
the way in entrepreneurship,making up nearly a quarter of
all new startups.
Today I'm joined in studio byJack Calhoun, founder of Encore
(01:21):
Career Lab.
And after selling his successfulwealth management firm, Jack
faced his own what now moment.
And from that experience, hecreated a powerful framework to
help others craft themeaningful, impactful, and
fulfilling second acts.
And we're going to get into itright now.
Jack, welcome to this emptinesslife.
SPEAKER_03 (01:39):
Jay, thank you so much.
I appreciate your uh yourinvitation and I love the the
work that you're doing here.
So it's it's a privilege to behere with you.
SPEAKER_01 (01:46):
Well, thank you.
I'm excited.
Like the idea of Encore career.
Like, I love a the phrase encorecareer.
It's just like perfect andforgetful thinking, like, oh
yeah, I could have a secondthing here.
But you you sold a business thatwas thriving, and then you ended
up asking yourself, what now?
So take us through that.
Like, how did you end up fromthere to Encore Career Lab?
(02:09):
Well, impulsively.
All good decisions areimpulsive, I've heard I heard.
SPEAKER_03 (02:16):
The classic ADD creative type.
And uh, I uh backed into theinvestment industry.
My dad was was in it.
He had a small firm.
He had been a stock broker andhe didn't like the commission
pressure, so he went independentand just took some of his
clients with him and around thelate 80s, early 90s.
(02:37):
And I was off in the liberalarts land.
I was a journalism major and itwas in sports marketing, but I
was getting the itch to dosomething on my own.
I also realized I was far tooADD to ever work for anybody
else.
So uh so I went to work withdad, who was just like me,
except even more so.
(02:57):
And so we were a dangerouscombination.
Lots of ideas, not always a lotof execution, but um, but we
found some people who were greatfor executing and implementing,
and uh and we grew and we didwell, and I learned the business
along the way.
And one of the things thatprobably contributed to some
(03:17):
imposter syndrome on my part wasbeing a creative in a very
analytical industry.
Um and in hindsight, I realizedthat was a real advantage for me
because there are dime a dozenanalytical types in the
industry, but not many peoplethat can communicate.
And um, it's one of those thingsyou appreciate in the rearview
mirror, right?
SPEAKER_01 (03:37):
Exactly.
I see some parallels herebecause I was the same way.
I was a tech, I was a chiefinformation officer in schools,
again, but creative.
Not like I learned the techstuff because I needed to be
able to talk, I needed to findpeople who could do the tech
stuff so I didn't have to worryabout it.
But you're right, there issomething there in terms of how
do we make this work?
And I I think I should probablyreintroduce this episode as
(03:59):
welcome to this ADD life becauseI sit in that same circle as
you.
SPEAKER_03 (04:02):
Yeah, well, there's a big market for that too.
So maybe you and I can join upon one of those.
SPEAKER_01 (04:06):
But there you go.
Um tell me, yeah, tell me aboutthe Encore career and what is
that exactly?
What does it look like?
SPEAKER_03 (04:14):
Yeah, so I had I ended up buying the company from
dad, and then I ended up sellingthe company, and there was a lot
of MA and consolidation andwealth management about 10 years
ago, and and I didn't really seeit coming.
It was that the the offersstarted coming to us, and that's
when I was like, oh, hmm.
Well, I'm almost 50, or maybe Iwas 50, and I thought, well,
(04:38):
I've done this for 25 years orwhatever, and and it's been fun,
and we've done good work.
I didn't wake up every day whenI was eight wanting to be a
registered investment advisor.
SPEAKER_01 (04:50):
It was not on a dream chart of eight years old.
SPEAKER_03 (04:52):
I wasn't on my dream chart, and uh so I felt like I
had done that and I was readyfor a new challenge.
And I thought, well, I'll takesome chips off the table and
I'll reinvent myself.
And I'm a creative guy and andthis will be fun.
And it was really naive.
I was really naive becausehaving been in wealth
management, I I knew a lot aboutretirement planning and all of
(05:16):
those things that go into asound retirement.
What I realize now is theindustry is really missing a big
holistic view of thisexperience, right?
It's spot on it.
Very, very obsessed with solvingfor X, right?
You have Y amount of money, youhave you know X amount of years,
(05:38):
you have Z amount of assets.
Does this formula work?
And if it does, go forth andparty down.
And if it doesn't, keep working.
And and that's the view.
And so I thought that's what Iwas supposed to do.
I've got money or whatever youwant to call it, and and now I
can go do something fun and andreinvent myself.
What what I mis uh understood ordidn't value properly is how
(06:03):
much of our identity getswrapped up in our work.
And I think with empty nesting,it's very much your work for a
lot of us is parenting, too.
And and when that goes away,there is this sort of
existential crisis for a lot ofpeople, uh, particularly if if
(06:24):
you were really invested in inwhat you did.
And if that became, and this islike I say, we did one of my
clients is a recently retiredOBGYN.
And he he he didn't say I helppeople have babies, he said I'm
an OBGYN.
And say I help people withinvesting, I said I'm an
(06:46):
investment advisor, right?
I am what I do.
And if someone's a full-timeparent, you might say I'm a
full-time mom or dad orstay-at-home mom or dad, and and
that's what you and so then thatgoes away, and then there's just
this sort of vacuum, I think.
And and I know you've touched onthis repeatedly in your episodes
(07:09):
and with your guests, but it'sreal.
And and I think for my case,people who were very invested in
their careers, it it is thissense that who am I without this
thing idea, right?
And and I didn't see it coming,I guess, because I didn't think
I wasn't this super type A guyworking 80 hours a week,
(07:31):
sacrificing everything for thesake of the company or whatever.
I had a pretty balanced life,and and really I considered
parenting and being a goodfather and husband to be my top
value and priority, and work wasa big part of that because of
the other family stuff.
And and so I thought I waspretty balanced, and when it
went away, I thought I'll justreapply this to a different
(07:54):
area, and and it was reallyhard.
And one of the things that Irealized is when you can do
anything, how do you define whatanything is, right?
Oh, yeah, I love that.
Yeah, and it's this called theparadox of choice, right?
It's like we have too many.
And I was my wife, Nancy told meto go get some toothpaste at the
(08:15):
grocery store a few weeks ago,in addition to other things.
And so I'm on the toothpastedial, and there's like 50
varieties of the same threebrands of toothpaste.
I'm like, I just want thetoothpaste, man, you know, and
and it was overwhelming.
I just stared at this wall oftoothpaste for three minutes
until finally I just grabbedsomething and kept going.
(08:36):
And and that's kind of ametaphor for what we face when
we leave our career behind.
It's it's it's well, we've gotto actually start defining
things.
And in some cases, I thinkclosing some doors so that we
don't have this overwhelm.
And we start to get a sense ofconfidence that here are some
(08:57):
directions that that resonatewith me and that potentially
resonate with people that wouldwant to work with me.
And and let me pursue thosebecause I feel good about those.
And so the the purpose of theprogram, Encore Career Lab, is
really to help people gain thatsense of confidence that they're
headed off in the rightdirection.
SPEAKER_01 (09:16):
Yeah, I love that.
And and you touched on like thethe idea of choice and that the
way you framed it.
Like I call that the Baskin andRobin syndrome.
There's 31 flavors, like, wheredo I like what do I do?
Where do I go?
And I think that best describeshow empty nesters look at this
next stage.
It's like, oh, there I there areso many choices, I choose to do
(09:36):
nothing, or I just choose towait to be involved in my kids'
life, wait for the engagementand the wedding and the
grandkids, rather than saying,oh, how do I seize an
opportunity here in my secondlife?
In wealth management, you'relooking at retirement, and I'm
looking at, hey, how do youmaximize your life between the
time the kids launch andretirement?
(09:59):
Right.
But I I think you talk a littlebit about, ooh, when we get to
this point, we hit this thing, Ithink you call it the drift.
Right.
That leads us to into, I'm justjust floating.
SPEAKER_03 (10:12):
Yeah.
SPEAKER_01 (10:13):
So what what does that look like?
And how do people, when theycome to you for the encore
career, when they come to you,like how do you help them
through the drift to get themlike headed in a direction where
they actually have a rudder?
SPEAKER_03 (10:24):
Yeah, that's a great analogy.
And and I think the phrase thatthat I've used is is the
wandering and wandering phase,um, which is which is basically
what the drift is.
And it's let's be honest, thisis kind of a first-world
problem, right?
We're we're blessed to have thisproblem and and food and shelter
taken care of, and we have somemeans, and and so in a sense,
(10:49):
what a blessing, right?
But also it's still real andit's still kind of overwhelming
and paralyzing.
And so I think it's importantthat we look at finding things
that are that feel like they arealigned with who we are, how we
like to work, what we feel likewe have to offer, and things
(11:13):
that feel purposeful to us.
And people get obsessed aboutfinding their purpose.
But Chip Connolly, who foundedModern Elder Academy, had a
great phrase that I loved.
He's like, Let's work on doingthings that are purposeful, and
then purpose will follow fromthat, right?
Love that.
Um, and so I didn't feel a lotof purpose from sound investment
(11:36):
principles when I was incollege, but 20 years later I
felt a lot because I'd investedmyself in it, right?
And and I felt there was a rightway and a wrong way to go about
it.
And so, but that came over time.
So I think when we get to thisphase, there's so much emphasis
on finding our purpose that wedon't know maybe what our
purpose is, right?
(11:56):
And parenting might have been apurpose for us, probably was,
and career, and when those goaway, it's well, I gotta find my
purpose before I can get going.
And actually, I think it's theopposite.
I think we get going on somesmart, relatively low friction,
low-risk directions and and trystuff and have some fun with it
and just take all thisperfectionism pressure off of
(12:18):
it.
Does that make sense?
It it makes perfect sense.
SPEAKER_01 (12:21):
And I I think too, like people who are listening,
like, oh, I don't even know howto get started on you.
No, my purpose was my kids.
I can't imagine another type ofpurpose, right?
But you but through assistanceand help and somebody kind of
showing you multiple ways thatthat could happen.
(12:42):
Well, let's take a look at it.
So, could you give us anexample?
Let's put this into likepractical terms for folks of
someone who went through yourprogram and discovered a new
purpose, and maybe maybe whatwas one of their biggest
breakthroughs in doing that?
SPEAKER_03 (12:57):
Yeah, I think I've got that's interesting.
One of my clients is uh CIO,former CIO for a big
manufacturing company in theupper Midwest.
And he was early retired, as Icall it.
It's the it's the proverbialoffer you can't refuse, right?
And this is the way that bigcorporations do these things,
right?
(13:17):
You know, you may not get thispackage again.
And it was one of those.
And so he wasn't mentally readyfor that.
He was early 60s and he reallyfelt like he'd been there since
he was out of college, right?
So this was his identity.
And he was, you know, there wassome he was embittered a bit
when we started workingtogether.
(13:38):
And I get that there's agrieving that goes to it when
it's not on your terms.
Um, but we worked through thatover some time.
Well, one of the things thathe's done is taking up distance
running, and he didn't startuntil he was 60 years old.
Now he's like 65.
And he is now preparing to runthe Chicago Marathon.
(13:59):
I think it's his ninth or tenthmarathon that he will have run.
And he didn't start until he was60 years old.
There are other younger runnerscoming to him asking for help,
asking how he's doing it.
He's got this Yoda stoicism whenhe goes about this running that
is appealing.
And so we're working with him onpotentially being this running
(14:23):
coach, is something you can doonline, right?
You can do it.
Absolutely.
A lot of ways to do it.
And it's gratifying and it'spotentially lucrative to him.
So that's one path that we'reworking on.
But there's also the path ofwhat he did in his career, and
people are coming to him askinghim for help with consulting.
And this is really thisdistinction David Brooks, the
(14:45):
writer, has made it it's it'scareer adjacent and non-career
adjacent for your encore career,which means doing stuff, a
different variation of what Idid before, but more on my
terms.
Okay.
Or something completelydifferent.
What I find is that highachievers, people who are career
(15:07):
invested, our logical brainsays, I've got all of this
experience, I should probablyjust do something that's related
to what I've done, right?
I get it.
On the other hand, our heart alot of times isn't still in it.
And we're burned out on it.
But in my case, writing was oneof my fortes in the investment
(15:27):
business, right?
I I was good at kind of JohnBogle plain talk investing
stuff.
And I knew I could teach that toother advisors who probably
weren't, it didn't comenaturally to them.
That could probably be alucrative encore career.
And I started down that path,and then I was so sick of
writing about the top, just waslike, I don't want to do it.
(15:50):
So I think, and I have a dentistin the program, same thing.
He was very successful, reallyan entrepreneur disguised as a
dentist, and uh and he has wantsto keep going with something.
When he started thinking aboutconsulting with younger dentists
that are behind the line ortimeline where he was.
But then I've found that hekeeps talking about it.
(16:11):
It sounds like work when hetalks about it.
And I'm like, well, we got tofigure this out because what I
do know at this point in life isif our heart isn't in it, we
will not see it through.
We might get intrigued by it, wemight start down that path, and
then we'll get stuck if it's inconflict with our values.
And so I think it's reallyimportant to get clear on the
(16:34):
why before we get into the whatand the how.
SPEAKER_01 (16:38):
Oh, absolutely.
Yeah, touching a little bit intoSimon Civic's work there.
Yeah.
I I love that you bring it up.
Like, that was me.
Like when I left my previouscareer, known nationally in
independent schools and techleaders, and was the chair of
the board of our professionalassociation right before I
pivoted.
And I I left like people werelike, you're gonna crush it as a
(17:02):
leadership coach for people whoare tech folks.
And I was like, I tried it, andI was like, my heart, my heart
wasn't in it.
Do I believe in leadership?
Absolutely, 100%.
I'm not saying I don't, but Iknew I wanted to have a bigger
impact, right?
And so it's tied to purpose, andthat's where I ended up with
this, and maybe a couple otherthings that I'm working on, but
(17:23):
it's also oh when you leave anentire community and identity
behind, it does rock your worlda little bit.
It does.
SPEAKER_03 (17:31):
It does.
It's your because it's yourcomfort zone, right?
And you know the people and youknow the players, the landscape.
It's it's literally comfortableto you.
Yeah.
And when we push outside ofthat, it triggers a lot of fear
and imposter syndrome and thingslike that.
One of my current clients is avery high-ranking military
(17:52):
member who's just retired, beenin the Pentagon and commanding
forces overseas.
And it's the same kind of thing.
It's it's it's even at thatlevel where you'd think that
person could write their ownticket, and really they can, but
it's still a completely civilianlife, is something he hasn't
experienced in 30 years.
Sure.
It looks like it does.
(18:14):
It comes for it comes foreverybody, but I also think
that's where a lot of the reallyfertile ground is.
Think about reinvention anddoing stuff that you know maybe
it it's tied into stuff we lovedwhen we were a kid.
But it's it's a more grown-upvariation of that, right?
So our program is really westart with the Hawaii, we try to
(18:38):
surface a lot of things.
We're really focused on helpingpeople get in touch with the
wisdom that they've acquired.
I call it their wisdomfingerprint.
We all have our unique kind ofamalgamation of experience and
perspective and natural giftsand talents that creates our
sort of unique wisdom brand, ifyou want to call it that, right?
(19:01):
Nobody has the same amalgamationas anybody else.
And there are other people thatreally can benefit from that.
And this is an age where, youknow, the the cerebral energy,
the fluid intelligence, if y'allhave ever gotten into that, that
high synapse firing stuff thatwe had in our 20s and 30s is
declining at this age.
(19:22):
It's that it's that cerebralenergy that we had when we were
younger.
But what we have in droves nowis this wisdom, this
crystallized intelligence,perspective, and judgment, and
you know, the was wisdom of theelders.
So it's really what we're aboutis trying to help people surface
what they've got to work with,where their passions are, where
(19:43):
their capabilities are, thepeople that they think that they
would like to work with.
And then we get more into thewhat, and then we get into the
how.
And uh and let's take this in alogical progression as opposed
to just trying stuff and gettingstuck, right?
Yeah.
Pretty much what my recipe waswhen I sold my company.
SPEAKER_01 (20:03):
Yeah, oh, absolutely.
Yeah, the who before the how isso important.
Yes, right, yeah, yeah.
And the why fits into there inadvance of that, but if you
don't know who you want to be orwhat you want things to look
like for yourself, then it makesit really difficult to kind of
even take that next step.
SPEAKER_03 (20:20):
It does because our values, you know, are we we
spend a lot of time onnon-negotiables because we
didn't have that luxury when wewere young.
We didn't get to decide who wewere going to work with all the
time and how and where and when,and and parenting too.
And so now we do.
(20:41):
We have two things that we wouldhave really dearly loved to have
had more of when we wereyounger, which is agency and
autonomy.
And that's the ability to decidewhat we want to do and the
capability to make it happen.
And so we need to find thingsthat are going to align with our
values and are non-negotiablesbecause we won't put up with the
(21:03):
crap, excuse my French, like wedid back when we were younger
because we don't have to.
And so I think that's what'simportant is to get clarity
about that ahead of time so wedon't spin our wheels and stuff
that ultimately is just notgoing to be the right direction
for us.
unknown (21:19):
Yeah.
SPEAKER_01 (21:19):
What what's kind of like the very first question you
have people answer when theycome to you?
SPEAKER_03 (21:59):
Well, do they have a sense of clarity about where
they think they're going?
If they do, then we spend sometime on that, and I helps me
understand what their thinkingis.
Most of the time it's it'scloudy.
And so I think what we try to dois to help realize that that's
not atypical.
(22:19):
People one of the things I findat this age, and I I had it
happen with me, is we're an agewhere we feel like we're
supposed to have it all figuredout, right?
SPEAKER_01 (22:27):
I mean, oh yeah, 100%.
SPEAKER_03 (22:29):
If we're empty nesters, presumably we launch
some children somewhere in theworld.
And we're we are either at thetop of our careers or we exited
at the top of our careers,however, we define that.
And so there's this sense that,you know, I should have this
figured out, right?
(22:51):
I tell my kids I do.
And so when we get stuck and wecan't figure out where to go
next, there's this kind of senselike, oh my gosh, it's me.
And insecurities surface.
And what I find is that peopletend to go internal.
Uh we we we get in our heads, wewant to get it figured out.
We don't want to worry peoplethat we're stuck that we care
(23:14):
about, and it's a littleembarrassing to us.
And so we just start reading andwe start consuming and we we get
all locked up in our head.
And and that is a sure recipefor analysis paralysis.
And and so I think the firstthing I try to reassure people
is it's not you, it's this phaseof life.
(23:36):
And genealogically, we're reallythe first generation that's
grappling with this, right?
True.
True.
Grandparents, even 30, 40 yearsago, and really even our
parents, and that wouldn't havething, they weren't thinking
about a thriving third act,right?
No, they were thinking aboutmartinis and viceroy cigarettes
(23:57):
like my grandparents were.
Um yeah, cocktail hour.
Not coincidentally, they didn'tlive that long.
Um, and so now we do.
We expect to have years and andand really decades left.
If you if you hit 60, you have a50-50 shot of seeing 90.
And you have a life expectancyof about 85, and it's just gonna
(24:20):
get longer as technologyimproves, right?
SPEAKER_01 (24:24):
Oh, absolutely.
Yeah.
Some of the people forecastingit out like our kids, my kids'
ages could live to be like 110or 120.
SPEAKER_03 (24:31):
Right.
And so that's that's completelydifferent perspective than
anybody had 30 or 40 years ago.
And even if they wanted to dostuff that was productive, they
were very limited what theycould do because this thing
we're doing here didn't exist,right?
There was no way to create yourown thing online or whatever.
You had to work for a bigcompany, and when the big
(24:53):
company was done with you, maybeyou could open up a wine shop or
something, right?
SPEAKER_01 (24:57):
But yeah, there wasn't a whole lot to it, and
now there's so many differentavenues people can go down, so
many different ways they canbecome an entrepreneur if they
want to.
I would imagine I'll say most, agood portion of the people
listening probably have ideaslike, oh, I thought about this
or I thought about that.
But then the cloudiness that youtalked about, like I call it
(25:19):
that's just fear, right?
It's just fear getting in theway of not allowing you to
explore that.
Yeah.
So what do you what do you sayto people who are like, oh,
yeah, I'm a little cloudy, orI'm afraid of taking that next
step?
I would imagine even ahigh-ranking military person is
afraid at some degree of goinginto something new that's in
civilian life because he hasn'tdone it before.
SPEAKER_03 (25:41):
Yeah, yes.
And and and and we all are.
And I think that is somethingthat we need to recognize is
human nature.
And our ego is there to, and itsrole is to protect us
reputationally, and and itdoesn't like it when we get out
there and start trying toreinvent ourselves or do
(26:01):
something different.
So it will start chirping at us,telling us, well, it's fine to
study and learn, but we're notgonna actually do anything.
That's ridiculous.
That's not who we are, right?
I don't know anything aboutthat.
No, no, no, let's stay herewhere everything's known, right?
But then you contrast that withthe the deathbed question that
is we see it all the time, whatare you what are your regrets?
(26:23):
And it's always not having thecourage to do the thing you
wanted to do.
Whatever that thing is.
And I think that's very real.
And and so that's where I thinkwe try to people bring process
and structure to this experienceis realizing there's a way to go
through this where we come outthe other side with a sense of
(26:46):
not only motivation andenthusiasm and optimism, but
also this clear vision of who weare and where we're going.
And that to me is the the thesecret ingredient of all this.
When we are younger, we we don'thave any problem getting a
vision of our future selves,right?
(27:07):
We can see ourselves as parents,we can see ourselves in career
levels that we aspire to.
Maybe we see ourselves in aneighborhood we want to live in
for the schools that our kidscould go to, or any of those
things, right?
They're all tangible.
And we see ourselves in thatlife and it pulls us forward.
And then we get to this phase oflife, and the culture is
(27:29):
completely geared around windingit down.
SPEAKER_01 (27:33):
Oh, absolutely.
You even get showcasedretirement at this stage, 15 or
20 years of this stage, so spoton.
It's not modeled.
SPEAKER_03 (27:43):
That's what they tell us to do, is now you're
just now you're just chilling.
And so now it's aboutexperiences, right?
And then the positiveexperiences are cruises and
antiquing and running throughamber waves of grain with the
sunlight glinting off of silverhair, right?
And and the downside imaging isI've fallen and I can't get up,
(28:04):
and stepless entry tubs, and allof these ridiculous things we
see when we've got the flu onWednesday at two o'clock and
we're watching TV, right?
And these are the models we'regiven of aging in this country,
and they're completely divorcedfrom reality and what things can
be.
And so the first thing is wehave to get clear on this future
(28:26):
vision.
It can't just be I'm playinggolf three days a week.
It's fun, nothing wrong with it.
It's part of what we want atthis phase is that freedom to do
what we want to do when we wantto do it, but there has to be an
overarching drive, purpose,ambition that's pulling us
forward that we can see thatfuture self uh down the road
(28:48):
that's compelling to us and it'spulling us into that future.
SPEAKER_01 (28:51):
Yeah.
I uh personally, I want to belike Mary Lee.
You're probably wondering who'sMary Lee?
Mary Lee was a 74-year-old womanin our group of people who hiked
Kilimanjaro.
Oh, wow.
She absolutely crushed it.
And I'm like, that's what I'mlike.
She's an example.
I want to be Mary Lee.
And then I saw a woman who waslike 80, I think 80 or 84,
(29:13):
somewhere in that range, walkingthe Camino in Spain.
It's like anything is possible.
Why do we want to shut it downbecause society says you you go
go, slow go, no go?
SPEAKER_03 (29:26):
And that's that's what we all bought into.
And this is this is if I'msanctimonious about anything,
it's rejecting this wholeretirement mentality that we've
had as a culture for over ahundred years or about a hundred
years, which came out of theSocial Security Act.
And and that that came out in1935, and and and it was a
(29:47):
safety net that's helpedmillions of people.
So that in and of itself was wasa good thing.
But they put an earnings test init that forced older workers
out.
And back then life expectancywas only 60 anyway.
So and and the economy, yeah,and the economy was very heavily
into manufacturing andagriculture, and it was
(30:08):
physically demanding, and peoplesmoked and drank, and they
weren't in great shape.
And so, yes, if you got to 60 or65, you probably weren't worn
out.
You probably couldn't keepworking, or if you were, you
were clinging.
And so that was designed to getolder, tired workers out of the
economy, bring in young,unemployed workers in the middle
of the Great Depression, and itestablished this mentality in
(30:31):
our culture.
That when I'm 65, I'm done withwork.
Now it's my time.
But nobody ever defined what mytime was.
And as people began livinglonger, they began, we began
seeing this sort of inertia andthis decline set in.
And I'm not a scientist orphysician.
(30:53):
I can't speak with authority,but there's a lot of data that
shows that the dementia epidemicwe're seeing, at least in part,
is from this extended atrophyingthat people are experiencing
that people just didn't livelong enough to experience 50
years ago.
SPEAKER_01 (31:09):
Yeah, yeah, yeah.
You you need to use it or youlose it.
Now, there's some things thathappen too with dementia that
are beyond that.
Right.
SPEAKER_03 (31:16):
There's there's other aspects to it.
SPEAKER_01 (31:18):
It's not just that, but it's like how do you stay
fulfilled?
Right.
And and I'm not saying we work acareer and that's always
fulfilling every single minuteof every day, but it does tie
into your identity as who youare, whether you're primary
caregiver, whether you workoutside the home, whatever it
looks like.
Yep.
Your identity does get wrappedup to that.
(31:38):
And we talked about that at thebeginning of the show.
Yep.
And it's it's a process ofunwinding your identity to even
begin to talk about what comesnext.
Yes.
In this next phase.
Right.
And so that's like step one isunwrapping your identity from
who you were before.
Yeah.
So that you can proceed.
So how do you how do you helppeople in that process?
(31:59):
I know how I do it when I workwith folks, but what's your
approach?
SPEAKER_03 (32:03):
Yeah, the term you're spot on, the term is
enmeshment.
I think that really nails it.
It's when our identity and ourwork get wrapped up together,
right?
Or it could be our identity andour our parenting, right?
But it's when external thingsbecome part of how we identify
ourselves.
Then it goes away, and thenwe're disoriented.
Um, what we try to do is to takepeople at the very beginning
(32:25):
through some assessments thatwe've done, some are outside uh
of what we've done, but likeClifton Strengths assessment,
I'm a big fan of.
And it gets back to your core ofwho you are, right?
What's that unique blend of ofyour talents and your experience
and your interests that comestogether to make you who you
(32:49):
are?
And we think we know and we do,and and we think when we get to
this age, it's like, I know me,I know my tendencies, but but
then you step back and you youget an appreciation for what you
really have to offer.
And one of the things that I seeconsistently is that people
undervalue this wisdom that theyhave and these capabilities and
(33:11):
what they know.
You know, and uh and I've seensome of the most profound
coaching programs launched bypeople who've been cancer
survivors or who've raised aspecial needs child and have
learned so much the hard way.
And there are people that arejust going into that experience
(33:32):
that are desperate for someoneto help them through it and who
can who's relatable and not justsome expert from on high.
Um, and and so sometimes thosecan make the best encore
careers, and they're completelynot adjacent to what people did
in their first careers, right?
(33:52):
And so I think that's part ofwhat we try to do is is help
people get back to what makesyou you beyond your career.
And then what do you have tooffer that the world really
needs?
And and you get to decide that,and we can find ways to test it
(34:14):
and see if the demand is there,but but it comes down to
redefining work, and work for somany of us in corporate America
and professional life is verygrindy with high burnout work,
right?
And and so when people get tothis age, a lot of times they
don't want to hear the wordwork, it's the four-letter work,
(34:35):
and so we really have toredefine that for this next
phase into more of your life'swork, and and and I love to
point to people that are highprofile, like the Rolling
Stones, right?
And Willie Nelson, and I wasjust watching a show the other
night, and there was a cameo byMel Brooks, who's 99, and he's
(34:57):
working on a rooting of theproducers, right?
And that's not grindy have towork for these people, right?
It's work they love to do.
And yes, they're rich andfamous, I get that.
But if rich and famous was allthere was, we we wouldn't have
the 27 club, right?
We wouldn't have all thesetragic stories of people who
(35:17):
died young.
So it's because they feel liketheir work is their their
purpose and not just the have-towork.
So that's the kind of work wewant to help our clients figure
out and find in what we do atEncore Career Line.
SPEAKER_01 (35:32):
I love that.
You it's interesting that youbrought up the Rolling Stones.
They're they're the number onebrought up example of what's
possible.
I don't know why, maybe it'sjust our generation and they
were bigger.
SPEAKER_03 (35:45):
It seems so unlikely Keith Richards would still be
kicking at this phase, right?
SPEAKER_01 (35:49):
Exactly.
Exactly.
But this is like the third timesomebody's brought it up as an
example.
I'm like, well, there'ssomething there to it.
SPEAKER_03 (35:55):
Yeah.
SPEAKER_01 (35:56):
You talk a little bit about the the wisdom
approach, right?
We have this amount of wisdomnow, or wisdom brand, I think is
what you called it.
Yeah, but oftentimes people say,well, I'll just volunteer or
I'll mentor.
Why is entrepreneurial ship sopowerful instead?
SPEAKER_03 (36:12):
Yeah.
This is a really fundamentalquestion that comes up a lot of
times, and it's well intended.
And I think what you find isthat people that were uh it
really invested in their careersor in their work with their kids
or whatever, when that goesaway, presumably we're in a
better financial situation thanwe were when you were younger.
(36:34):
We have more capacity, and wethink, well, I I can give more
now.
There's this, it's calledgenerativity, is the term.
It was by Eric Erickson, thepsychologist, and it's this
compulsion we feel to give backas we get older.
It's wired in us.
And so I think that that's wherewe have to really look towards
(36:55):
what is that going, what's goingto scratch that itch for us,
right?
How are we going to find ways togive back um that are still in
line with our values and ourpriorities and what's driving us
at this point in life, and notend up spinning our wheels doing
things that seem like they'd beinteresting, but that we don't
(37:17):
feel really passionate about?
Does that I may have gotten offtopic.
So that answered.
SPEAKER_01 (37:23):
Yeah, you're right there.
Yeah, right on, spot on withthat.
It's it's this has been afascinating conversation.
I think one that's beenhopefully super powerful for
people who uh will listen tothis episode because it is such
a good example of what'spossible once the kids leave
home.
(37:44):
And before I let you go, I I'mjust curious, what's one thing
you've learned about yourself indeveloping and creating Encore
Career Lab and your journey?
SPEAKER_03 (37:59):
It really lights me up seeing what people have to
offer and seeing them discoverthat.
And and it's there's a variationof that from wealth management,
but it's not exactly the same.
And the people that come intothe program have so much
potential and and they don'tappreciate it, they don't see it
(38:20):
a lot of times.
They're humble people and theyunderestimate themselves.
So it's really energizing to meto see them start to get excited
about that because thedownstream effects, the
butterfly effect, you just younever know.
SPEAKER_01 (38:34):
Yeah, the ripples and ripples are out there, and
who knows if you inspiresomebody else.
SPEAKER_03 (38:40):
Just one person, who knows?
Who knows?
That might be the one personthat changes the world, right?
SPEAKER_01 (38:45):
I believe that 100%.
Impact one or impact onemillion, there's no difference.
Impact is impact.
And when the kids leave home, Ithink we can still impact the
lives of others, just not ourkids.
SPEAKER_03 (38:57):
Yeah, absolutely.
SPEAKER_01 (38:59):
Jack, thank you so much for being here today.
The conversation was fantastic,and I look forward to seeing how
Encore Career Lab continues togrow and shine a light on what's
possible for folks.
SPEAKER_03 (39:10):
Thanks, Jay.
I appreciate the invitation.
It's been great being on, and Ilove what you're doing, so keep
up the good work.
SPEAKER_00 (39:16):
Thank you for listening to this Empty Nest
Life.
Remember, this chapter isn't anending, it's an invitation to
redefine, rediscover, andreignite your life.
If today's episode sparkssomething in you, don't forget
to take that first step andvisit thisemptynestlife.com and
click work with me to get theconversation started.
Until next time, keep your heartopen, your mind curious, and
your spirit shining.
(39:39):
This Empty Nest Life is aproduction of Impact One Media
LLC.
All rights reserved.
We have two things that we would have really dearly
loved to have had more of whenwe were younger, which is agency
and autonomy.
And that's the ability to decidewhat we want to do and the
capability to make it happen.
And so we need to find thingsthat are going to align with our
values and are non-negotiables.
(00:20):
I think that's what's importantis to get clarity about that
ahead of time so we don't spinour wheels and stuff that
ultimately is just not going tobe the right direction for us.
SPEAKER_00 (00:28):
Welcome to this Empty Nest Life, the podcast
dedicated to helping you embracethis transformative season with
purpose, passion, and joy.
In each episode, we explorestories, strategies, and
insights to help turn your emptynest into an exciting new
chapter.
Whether you're redefining youridentity, pursuing new passions,
or finding peace in the pause,you're in the right place.
Here's your host, the Empty Nestcoach, Jay Ramsden.
SPEAKER_01 (00:50):
Hey there, my emptiness friends.
There are so many possibilitiesin our emptiness life to
consider (00:56):
downsizing, moving, second careers, maybe even
retirement.
But here's something I learnedthat just might pique your
interest if you've ever thought,hey, I have an idea for a
business.
Right now, there's a surge inAmericans aged 55 to 64 leading
the way in entrepreneurship,making up nearly a quarter of
all new startups.
Today I'm joined in studio byJack Calhoun, founder of Encore
(01:21):
Career Lab.
And after selling his successfulwealth management firm, Jack
faced his own what now moment.
And from that experience, hecreated a powerful framework to
help others craft themeaningful, impactful, and
fulfilling second acts.
And we're going to get into itright now.
Jack, welcome to this emptinesslife.
SPEAKER_03 (01:39):
Jay, thank you so much.
I appreciate your uh yourinvitation and I love the the
work that you're doing here.
So it's it's a privilege to behere with you.
SPEAKER_01 (01:46):
Well, thank you.
I'm excited.
Like the idea of Encore career.
Like, I love a the phrase encorecareer.
It's just like perfect andforgetful thinking, like, oh
yeah, I could have a secondthing here.
But you you sold a business thatwas thriving, and then you ended
up asking yourself, what now?
So take us through that.
Like, how did you end up fromthere to Encore Career Lab?
(02:09):
Well, impulsively.
All good decisions areimpulsive, I've heard I heard.
SPEAKER_03 (02:16):
The classic ADD creative type.
And uh, I uh backed into theinvestment industry.
My dad was was in it.
He had a small firm.
He had been a stock broker andhe didn't like the commission
pressure, so he went independentand just took some of his
clients with him and around thelate 80s, early 90s.
(02:37):
And I was off in the liberalarts land.
I was a journalism major and itwas in sports marketing, but I
was getting the itch to dosomething on my own.
I also realized I was far tooADD to ever work for anybody
else.
So uh so I went to work withdad, who was just like me,
except even more so.
(02:57):
And so we were a dangerouscombination.
Lots of ideas, not always a lotof execution, but um, but we
found some people who were greatfor executing and implementing,
and uh and we grew and we didwell, and I learned the business
along the way.
And one of the things thatprobably contributed to some
(03:17):
imposter syndrome on my part wasbeing a creative in a very
analytical industry.
Um and in hindsight, I realizedthat was a real advantage for me
because there are dime a dozenanalytical types in the
industry, but not many peoplethat can communicate.
And um, it's one of those thingsyou appreciate in the rearview
mirror, right?
SPEAKER_01 (03:37):
Exactly.
I see some parallels herebecause I was the same way.
I was a tech, I was a chiefinformation officer in schools,
again, but creative.
Not like I learned the techstuff because I needed to be
able to talk, I needed to findpeople who could do the tech
stuff so I didn't have to worryabout it.
But you're right, there issomething there in terms of how
do we make this work?
And I I think I should probablyreintroduce this episode as
(03:59):
welcome to this ADD life becauseI sit in that same circle as
you.
SPEAKER_03 (04:02):
Yeah, well, there's a big market for that too.
So maybe you and I can join upon one of those.
SPEAKER_01 (04:06):
But there you go.
Um tell me, yeah, tell me aboutthe Encore career and what is
that exactly?
What does it look like?
SPEAKER_03 (04:14):
Yeah, so I had I ended up buying the company from
dad, and then I ended up sellingthe company, and there was a lot
of MA and consolidation andwealth management about 10 years
ago, and and I didn't really seeit coming.
It was that the the offersstarted coming to us, and that's
when I was like, oh, hmm.
Well, I'm almost 50, or maybe Iwas 50, and I thought, well,
(04:38):
I've done this for 25 years orwhatever, and and it's been fun,
and we've done good work.
I didn't wake up every day whenI was eight wanting to be a
registered investment advisor.
SPEAKER_01 (04:50):
It was not on a dream chart of eight years old.
SPEAKER_03 (04:52):
I wasn't on my dream chart, and uh so I felt like I
had done that and I was readyfor a new challenge.
And I thought, well, I'll takesome chips off the table and
I'll reinvent myself.
And I'm a creative guy and andthis will be fun.
And it was really naive.
I was really naive becausehaving been in wealth
management, I I knew a lot aboutretirement planning and all of
(05:16):
those things that go into asound retirement.
What I realize now is theindustry is really missing a big
holistic view of thisexperience, right?
It's spot on it.
Very, very obsessed with solvingfor X, right?
You have Y amount of money, youhave you know X amount of years,
(05:38):
you have Z amount of assets.
Does this formula work?
And if it does, go forth andparty down.
And if it doesn't, keep working.
And and that's the view.
And so I thought that's what Iwas supposed to do.
I've got money or whatever youwant to call it, and and now I
can go do something fun and andreinvent myself.
What what I mis uh understood ordidn't value properly is how
(06:03):
much of our identity getswrapped up in our work.
And I think with empty nesting,it's very much your work for a
lot of us is parenting, too.
And and when that goes away,there is this sort of
existential crisis for a lot ofpeople, uh, particularly if if
(06:24):
you were really invested in inwhat you did.
And if that became, and this islike I say, we did one of my
clients is a recently retiredOBGYN.
And he he he didn't say I helppeople have babies, he said I'm
an OBGYN.
And say I help people withinvesting, I said I'm an
(06:46):
investment advisor, right?
I am what I do.
And if someone's a full-timeparent, you might say I'm a
full-time mom or dad orstay-at-home mom or dad, and and
that's what you and so then thatgoes away, and then there's just
this sort of vacuum, I think.
And and I know you've touched onthis repeatedly in your episodes
(07:09):
and with your guests, but it'sreal.
And and I think for my case,people who were very invested in
their careers, it it is thissense that who am I without this
thing idea, right?
And and I didn't see it coming,I guess, because I didn't think
I wasn't this super type A guyworking 80 hours a week,
(07:31):
sacrificing everything for thesake of the company or whatever.
I had a pretty balanced life,and and really I considered
parenting and being a goodfather and husband to be my top
value and priority, and work wasa big part of that because of
the other family stuff.
And and so I thought I waspretty balanced, and when it
went away, I thought I'll justreapply this to a different
(07:54):
area, and and it was reallyhard.
And one of the things that Irealized is when you can do
anything, how do you define whatanything is, right?
Oh, yeah, I love that.
Yeah, and it's this called theparadox of choice, right?
It's like we have too many.
And I was my wife, Nancy told meto go get some toothpaste at the
(08:15):
grocery store a few weeks ago,in addition to other things.
And so I'm on the toothpastedial, and there's like 50
varieties of the same threebrands of toothpaste.
I'm like, I just want thetoothpaste, man, you know, and
and it was overwhelming.
I just stared at this wall oftoothpaste for three minutes
until finally I just grabbedsomething and kept going.
(08:36):
And and that's kind of ametaphor for what we face when
we leave our career behind.
It's it's it's well, we've gotto actually start defining
things.
And in some cases, I thinkclosing some doors so that we
don't have this overwhelm.
And we start to get a sense ofconfidence that here are some
(08:57):
directions that that resonatewith me and that potentially
resonate with people that wouldwant to work with me.
And and let me pursue thosebecause I feel good about those.
And so the the purpose of theprogram, Encore Career Lab, is
really to help people gain thatsense of confidence that they're
headed off in the rightdirection.
SPEAKER_01 (09:16):
Yeah, I love that.
And and you touched on like thethe idea of choice and that the
way you framed it.
Like I call that the Baskin andRobin syndrome.
There's 31 flavors, like, wheredo I like what do I do?
Where do I go?
And I think that best describeshow empty nesters look at this
next stage.
It's like, oh, there I there areso many choices, I choose to do
(09:36):
nothing, or I just choose towait to be involved in my kids'
life, wait for the engagementand the wedding and the
grandkids, rather than saying,oh, how do I seize an
opportunity here in my secondlife?
In wealth management, you'relooking at retirement, and I'm
looking at, hey, how do youmaximize your life between the
time the kids launch andretirement?
(09:59):
Right.
But I I think you talk a littlebit about, ooh, when we get to
this point, we hit this thing, Ithink you call it the drift.
Right.
That leads us to into, I'm justjust floating.
SPEAKER_03 (10:12):
Yeah.
SPEAKER_01 (10:13):
So what what does that look like?
And how do people, when theycome to you for the encore
career, when they come to you,like how do you help them
through the drift to get themlike headed in a direction where
they actually have a rudder?
SPEAKER_03 (10:24):
Yeah, that's a great analogy.
And and I think the phrase thatthat I've used is is the
wandering and wandering phase,um, which is which is basically
what the drift is.
And it's let's be honest, thisis kind of a first-world
problem, right?
We're we're blessed to have thisproblem and and food and shelter
taken care of, and we have somemeans, and and so in a sense,
(10:49):
what a blessing, right?
But also it's still real andit's still kind of overwhelming
and paralyzing.
And so I think it's importantthat we look at finding things
that are that feel like they arealigned with who we are, how we
like to work, what we feel likewe have to offer, and things
(11:13):
that feel purposeful to us.
And people get obsessed aboutfinding their purpose.
But Chip Connolly, who foundedModern Elder Academy, had a
great phrase that I loved.
He's like, Let's work on doingthings that are purposeful, and
then purpose will follow fromthat, right?
Love that.
Um, and so I didn't feel a lotof purpose from sound investment
(11:36):
principles when I was incollege, but 20 years later I
felt a lot because I'd investedmyself in it, right?
And and I felt there was a rightway and a wrong way to go about
it.
And so, but that came over time.
So I think when we get to thisphase, there's so much emphasis
on finding our purpose that wedon't know maybe what our
purpose is, right?
(11:56):
And parenting might have been apurpose for us, probably was,
and career, and when those goaway, it's well, I gotta find my
purpose before I can get going.
And actually, I think it's theopposite.
I think we get going on somesmart, relatively low friction,
low-risk directions and and trystuff and have some fun with it
and just take all thisperfectionism pressure off of
(12:18):
it.
Does that make sense?
It it makes perfect sense.
SPEAKER_01 (12:21):
And I I think too, like people who are listening,
like, oh, I don't even know howto get started on you.
No, my purpose was my kids.
I can't imagine another type ofpurpose, right?
But you but through assistanceand help and somebody kind of
showing you multiple ways thatthat could happen.
(12:42):
Well, let's take a look at it.
So, could you give us anexample?
Let's put this into likepractical terms for folks of
someone who went through yourprogram and discovered a new
purpose, and maybe maybe whatwas one of their biggest
breakthroughs in doing that?
SPEAKER_03 (12:57):
Yeah, I think I've got that's interesting.
One of my clients is uh CIO,former CIO for a big
manufacturing company in theupper Midwest.
And he was early retired, as Icall it.
It's the it's the proverbialoffer you can't refuse, right?
And this is the way that bigcorporations do these things,
right?
(13:17):
You know, you may not get thispackage again.
And it was one of those.
And so he wasn't mentally readyfor that.
He was early 60s and he reallyfelt like he'd been there since
he was out of college, right?
So this was his identity.
And he was, you know, there wassome he was embittered a bit
when we started workingtogether.
(13:38):
And I get that there's agrieving that goes to it when
it's not on your terms.
Um, but we worked through thatover some time.
Well, one of the things thathe's done is taking up distance
running, and he didn't startuntil he was 60 years old.
Now he's like 65.
And he is now preparing to runthe Chicago Marathon.
(13:59):
I think it's his ninth or tenthmarathon that he will have run.
And he didn't start until he was60 years old.
There are other younger runnerscoming to him asking for help,
asking how he's doing it.
He's got this Yoda stoicism whenhe goes about this running that
is appealing.
And so we're working with him onpotentially being this running
(14:23):
coach, is something you can doonline, right?
You can do it.
Absolutely.
A lot of ways to do it.
And it's gratifying and it'spotentially lucrative to him.
So that's one path that we'reworking on.
But there's also the path ofwhat he did in his career, and
people are coming to him askinghim for help with consulting.
And this is really thisdistinction David Brooks, the
(14:45):
writer, has made it it's it'scareer adjacent and non-career
adjacent for your encore career,which means doing stuff, a
different variation of what Idid before, but more on my
terms.
Okay.
Or something completelydifferent.
What I find is that highachievers, people who are career
(15:07):
invested, our logical brainsays, I've got all of this
experience, I should probablyjust do something that's related
to what I've done, right?
I get it.
On the other hand, our heart alot of times isn't still in it.
And we're burned out on it.
But in my case, writing was oneof my fortes in the investment
(15:27):
business, right?
I I was good at kind of JohnBogle plain talk investing
stuff.
And I knew I could teach that toother advisors who probably
weren't, it didn't comenaturally to them.
That could probably be alucrative encore career.
And I started down that path,and then I was so sick of
writing about the top, just waslike, I don't want to do it.
(15:50):
So I think, and I have a dentistin the program, same thing.
He was very successful, reallyan entrepreneur disguised as a
dentist, and uh and he has wantsto keep going with something.
When he started thinking aboutconsulting with younger dentists
that are behind the line ortimeline where he was.
But then I've found that hekeeps talking about it.
(16:11):
It sounds like work when hetalks about it.
And I'm like, well, we got tofigure this out because what I
do know at this point in life isif our heart isn't in it, we
will not see it through.
We might get intrigued by it, wemight start down that path, and
then we'll get stuck if it's inconflict with our values.
And so I think it's reallyimportant to get clear on the
(16:34):
why before we get into the whatand the how.
SPEAKER_01 (16:38):
Oh, absolutely.
Yeah, touching a little bit intoSimon Civic's work there.
Yeah.
I I love that you bring it up.
Like, that was me.
Like when I left my previouscareer, known nationally in
independent schools and techleaders, and was the chair of
the board of our professionalassociation right before I
pivoted.
And I I left like people werelike, you're gonna crush it as a
(17:02):
leadership coach for people whoare tech folks.
And I was like, I tried it, andI was like, my heart, my heart
wasn't in it.
Do I believe in leadership?
Absolutely, 100%.
I'm not saying I don't, but Iknew I wanted to have a bigger
impact, right?
And so it's tied to purpose, andthat's where I ended up with
this, and maybe a couple otherthings that I'm working on, but
(17:23):
it's also oh when you leave anentire community and identity
behind, it does rock your worlda little bit.
It does.
SPEAKER_03 (17:31):
It does.
It's your because it's yourcomfort zone, right?
And you know the people and youknow the players, the landscape.
It's it's literally comfortableto you.
Yeah.
And when we push outside ofthat, it triggers a lot of fear
and imposter syndrome and thingslike that.
One of my current clients is avery high-ranking military
(17:52):
member who's just retired, beenin the Pentagon and commanding
forces overseas.
And it's the same kind of thing.
It's it's it's even at thatlevel where you'd think that
person could write their ownticket, and really they can, but
it's still a completely civilianlife, is something he hasn't
experienced in 30 years.
Sure.
It looks like it does.
(18:14):
It comes for it comes foreverybody, but I also think
that's where a lot of the reallyfertile ground is.
Think about reinvention anddoing stuff that you know maybe
it it's tied into stuff we lovedwhen we were a kid.
But it's it's a more grown-upvariation of that, right?
So our program is really westart with the Hawaii, we try to
(18:38):
surface a lot of things.
We're really focused on helpingpeople get in touch with the
wisdom that they've acquired.
I call it their wisdomfingerprint.
We all have our unique kind ofamalgamation of experience and
perspective and natural giftsand talents that creates our
sort of unique wisdom brand, ifyou want to call it that, right?
(19:01):
Nobody has the same amalgamationas anybody else.
And there are other people thatreally can benefit from that.
And this is an age where, youknow, the the cerebral energy,
the fluid intelligence, if y'allhave ever gotten into that, that
high synapse firing stuff thatwe had in our 20s and 30s is
declining at this age.
(19:22):
It's that it's that cerebralenergy that we had when we were
younger.
But what we have in droves nowis this wisdom, this
crystallized intelligence,perspective, and judgment, and
you know, the was wisdom of theelders.
So it's really what we're aboutis trying to help people surface
what they've got to work with,where their passions are, where
(19:43):
their capabilities are, thepeople that they think that they
would like to work with.
And then we get more into thewhat, and then we get into the
how.
And uh and let's take this in alogical progression as opposed
to just trying stuff and gettingstuck, right?
Yeah.
Pretty much what my recipe waswhen I sold my company.
SPEAKER_01 (20:03):
Yeah, oh, absolutely.
Yeah, the who before the how isso important.
Yes, right, yeah, yeah.
And the why fits into there inadvance of that, but if you
don't know who you want to be orwhat you want things to look
like for yourself, then it makesit really difficult to kind of
even take that next step.
SPEAKER_03 (20:20):
It does because our values, you know, are we we
spend a lot of time onnon-negotiables because we
didn't have that luxury when wewere young.
We didn't get to decide who wewere going to work with all the
time and how and where and when,and and parenting too.
And so now we do.
(20:41):
We have two things that we wouldhave really dearly loved to have
had more of when we wereyounger, which is agency and
autonomy.
And that's the ability to decidewhat we want to do and the
capability to make it happen.
And so we need to find thingsthat are going to align with our
values and are non-negotiablesbecause we won't put up with the
(21:03):
crap, excuse my French, like wedid back when we were younger
because we don't have to.
And so I think that's what'simportant is to get clarity
about that ahead of time so wedon't spin our wheels and stuff
that ultimately is just notgoing to be the right direction
for us.
unknown (21:19):
Yeah.
SPEAKER_01 (21:19):
What what's kind of like the very first question you
have people answer when theycome to you?
SPEAKER_03 (21:59):
Well, do they have a sense of clarity about where
they think they're going?
If they do, then we spend sometime on that, and I helps me
understand what their thinkingis.
Most of the time it's it'scloudy.
And so I think what we try to dois to help realize that that's
not atypical.
(22:19):
People one of the things I findat this age, and I I had it
happen with me, is we're an agewhere we feel like we're
supposed to have it all figuredout, right?
SPEAKER_01 (22:27):
I mean, oh yeah, 100%.
SPEAKER_03 (22:29):
If we're empty nesters, presumably we launch
some children somewhere in theworld.
And we're we are either at thetop of our careers or we exited
at the top of our careers,however, we define that.
And so there's this sense that,you know, I should have this
figured out, right?
(22:51):
I tell my kids I do.
And so when we get stuck and wecan't figure out where to go
next, there's this kind of senselike, oh my gosh, it's me.
And insecurities surface.
And what I find is that peopletend to go internal.
Uh we we we get in our heads, wewant to get it figured out.
We don't want to worry peoplethat we're stuck that we care
(23:14):
about, and it's a littleembarrassing to us.
And so we just start reading andwe start consuming and we we get
all locked up in our head.
And and that is a sure recipefor analysis paralysis.
And and so I think the firstthing I try to reassure people
is it's not you, it's this phaseof life.
(23:36):
And genealogically, we're reallythe first generation that's
grappling with this, right?
True.
True.
Grandparents, even 30, 40 yearsago, and really even our
parents, and that wouldn't havething, they weren't thinking
about a thriving third act,right?
No, they were thinking aboutmartinis and viceroy cigarettes
(23:57):
like my grandparents were.
Um yeah, cocktail hour.
Not coincidentally, they didn'tlive that long.
Um, and so now we do.
We expect to have years and andand really decades left.
If you if you hit 60, you have a50-50 shot of seeing 90.
And you have a life expectancyof about 85, and it's just gonna
(24:20):
get longer as technologyimproves, right?
SPEAKER_01 (24:24):
Oh, absolutely.
Yeah.
Some of the people forecastingit out like our kids, my kids'
ages could live to be like 110or 120.
SPEAKER_03 (24:31):
Right.
And so that's that's completelydifferent perspective than
anybody had 30 or 40 years ago.
And even if they wanted to dostuff that was productive, they
were very limited what theycould do because this thing
we're doing here didn't exist,right?
There was no way to create yourown thing online or whatever.
You had to work for a bigcompany, and when the big
(24:53):
company was done with you, maybeyou could open up a wine shop or
something, right?
SPEAKER_01 (24:57):
But yeah, there wasn't a whole lot to it, and
now there's so many differentavenues people can go down, so
many different ways they canbecome an entrepreneur if they
want to.
I would imagine I'll say most, agood portion of the people
listening probably have ideaslike, oh, I thought about this
or I thought about that.
But then the cloudiness that youtalked about, like I call it
(25:19):
that's just fear, right?
It's just fear getting in theway of not allowing you to
explore that.
Yeah.
So what do you what do you sayto people who are like, oh,
yeah, I'm a little cloudy, orI'm afraid of taking that next
step?
I would imagine even ahigh-ranking military person is
afraid at some degree of goinginto something new that's in
civilian life because he hasn'tdone it before.
SPEAKER_03 (25:41):
Yeah, yes.
And and and and we all are.
And I think that is somethingthat we need to recognize is
human nature.
And our ego is there to, and itsrole is to protect us
reputationally, and and itdoesn't like it when we get out
there and start trying toreinvent ourselves or do
(26:01):
something different.
So it will start chirping at us,telling us, well, it's fine to
study and learn, but we're notgonna actually do anything.
That's ridiculous.
That's not who we are, right?
I don't know anything aboutthat.
No, no, no, let's stay herewhere everything's known, right?
But then you contrast that withthe the deathbed question that
is we see it all the time, whatare you what are your regrets?
(26:23):
And it's always not having thecourage to do the thing you
wanted to do.
Whatever that thing is.
And I think that's very real.
And and so that's where I thinkwe try to people bring process
and structure to this experienceis realizing there's a way to go
through this where we come outthe other side with a sense of
(26:46):
not only motivation andenthusiasm and optimism, but
also this clear vision of who weare and where we're going.
And that to me is the the thesecret ingredient of all this.
When we are younger, we we don'thave any problem getting a
vision of our future selves,right?
(27:07):
We can see ourselves as parents,we can see ourselves in career
levels that we aspire to.
Maybe we see ourselves in aneighborhood we want to live in
for the schools that our kidscould go to, or any of those
things, right?
They're all tangible.
And we see ourselves in thatlife and it pulls us forward.
And then we get to this phase oflife, and the culture is
(27:29):
completely geared around windingit down.
SPEAKER_01 (27:33):
Oh, absolutely.
You even get showcasedretirement at this stage, 15 or
20 years of this stage, so spoton.
It's not modeled.
SPEAKER_03 (27:43):
That's what they tell us to do, is now you're
just now you're just chilling.
And so now it's aboutexperiences, right?
And then the positiveexperiences are cruises and
antiquing and running throughamber waves of grain with the
sunlight glinting off of silverhair, right?
And and the downside imaging isI've fallen and I can't get up,
(28:04):
and stepless entry tubs, and allof these ridiculous things we
see when we've got the flu onWednesday at two o'clock and
we're watching TV, right?
And these are the models we'regiven of aging in this country,
and they're completely divorcedfrom reality and what things can
be.
And so the first thing is wehave to get clear on this future
(28:26):
vision.
It can't just be I'm playinggolf three days a week.
It's fun, nothing wrong with it.
It's part of what we want atthis phase is that freedom to do
what we want to do when we wantto do it, but there has to be an
overarching drive, purpose,ambition that's pulling us
forward that we can see thatfuture self uh down the road
(28:48):
that's compelling to us and it'spulling us into that future.
SPEAKER_01 (28:51):
Yeah.
I uh personally, I want to belike Mary Lee.
You're probably wondering who'sMary Lee?
Mary Lee was a 74-year-old womanin our group of people who hiked
Kilimanjaro.
Oh, wow.
She absolutely crushed it.
And I'm like, that's what I'mlike.
She's an example.
I want to be Mary Lee.
And then I saw a woman who waslike 80, I think 80 or 84,
(29:13):
somewhere in that range, walkingthe Camino in Spain.
It's like anything is possible.
Why do we want to shut it downbecause society says you you go
go, slow go, no go?
SPEAKER_03 (29:26):
And that's that's what we all bought into.
And this is this is if I'msanctimonious about anything,
it's rejecting this wholeretirement mentality that we've
had as a culture for over ahundred years or about a hundred
years, which came out of theSocial Security Act.
And and that that came out in1935, and and and it was a
(29:47):
safety net that's helpedmillions of people.
So that in and of itself was wasa good thing.
But they put an earnings test init that forced older workers
out.
And back then life expectancywas only 60 anyway.
So and and the economy, yeah,and the economy was very heavily
into manufacturing andagriculture, and it was
(30:08):
physically demanding, and peoplesmoked and drank, and they
weren't in great shape.
And so, yes, if you got to 60 or65, you probably weren't worn
out.
You probably couldn't keepworking, or if you were, you
were clinging.
And so that was designed to getolder, tired workers out of the
economy, bring in young,unemployed workers in the middle
of the Great Depression, and itestablished this mentality in
(30:31):
our culture.
That when I'm 65, I'm done withwork.
Now it's my time.
But nobody ever defined what mytime was.
And as people began livinglonger, they began, we began
seeing this sort of inertia andthis decline set in.
And I'm not a scientist orphysician.
(30:53):
I can't speak with authority,but there's a lot of data that
shows that the dementia epidemicwe're seeing, at least in part,
is from this extended atrophyingthat people are experiencing
that people just didn't livelong enough to experience 50
years ago.
SPEAKER_01 (31:09):
Yeah, yeah, yeah.
You you need to use it or youlose it.
Now, there's some things thathappen too with dementia that
are beyond that.
Right.
SPEAKER_03 (31:16):
There's there's other aspects to it.
SPEAKER_01 (31:18):
It's not just that, but it's like how do you stay
fulfilled?
Right.
And and I'm not saying we work acareer and that's always
fulfilling every single minuteof every day, but it does tie
into your identity as who youare, whether you're primary
caregiver, whether you workoutside the home, whatever it
looks like.
Yep.
Your identity does get wrappedup to that.
(31:38):
And we talked about that at thebeginning of the show.
Yep.
And it's it's a process ofunwinding your identity to even
begin to talk about what comesnext.
Yes.
In this next phase.
Right.
And so that's like step one isunwrapping your identity from
who you were before.
Yeah.
So that you can proceed.
So how do you how do you helppeople in that process?
(31:59):
I know how I do it when I workwith folks, but what's your
approach?
SPEAKER_03 (32:03):
Yeah, the term you're spot on, the term is
enmeshment.
I think that really nails it.
It's when our identity and ourwork get wrapped up together,
right?
Or it could be our identity andour our parenting, right?
But it's when external thingsbecome part of how we identify
ourselves.
Then it goes away, and thenwe're disoriented.
Um, what we try to do is to takepeople at the very beginning
(32:25):
through some assessments thatwe've done, some are outside uh
of what we've done, but likeClifton Strengths assessment,
I'm a big fan of.
And it gets back to your core ofwho you are, right?
What's that unique blend of ofyour talents and your experience
and your interests that comestogether to make you who you
(32:49):
are?
And we think we know and we do,and and we think when we get to
this age, it's like, I know me,I know my tendencies, but but
then you step back and you youget an appreciation for what you
really have to offer.
And one of the things that I seeconsistently is that people
undervalue this wisdom that theyhave and these capabilities and
(33:11):
what they know.
You know, and uh and I've seensome of the most profound
coaching programs launched bypeople who've been cancer
survivors or who've raised aspecial needs child and have
learned so much the hard way.
And there are people that arejust going into that experience
(33:32):
that are desperate for someoneto help them through it and who
can who's relatable and not justsome expert from on high.
Um, and and so sometimes thosecan make the best encore
careers, and they're completelynot adjacent to what people did
in their first careers, right?
(33:52):
And so I think that's part ofwhat we try to do is is help
people get back to what makesyou you beyond your career.
And then what do you have tooffer that the world really
needs?
And and you get to decide that,and we can find ways to test it
(34:14):
and see if the demand is there,but but it comes down to
redefining work, and work for somany of us in corporate America
and professional life is verygrindy with high burnout work,
right?
And and so when people get tothis age, a lot of times they
don't want to hear the wordwork, it's the four-letter work,
(34:35):
and so we really have toredefine that for this next
phase into more of your life'swork, and and and I love to
point to people that are highprofile, like the Rolling
Stones, right?
And Willie Nelson, and I wasjust watching a show the other
night, and there was a cameo byMel Brooks, who's 99, and he's
(34:57):
working on a rooting of theproducers, right?
And that's not grindy have towork for these people, right?
It's work they love to do.
And yes, they're rich andfamous, I get that.
But if rich and famous was allthere was, we we wouldn't have
the 27 club, right?
We wouldn't have all thesetragic stories of people who
(35:17):
died young.
So it's because they feel liketheir work is their their
purpose and not just the have-towork.
So that's the kind of work wewant to help our clients figure
out and find in what we do atEncore Career Line.
SPEAKER_01 (35:32):
I love that.
You it's interesting that youbrought up the Rolling Stones.
They're they're the number onebrought up example of what's
possible.
I don't know why, maybe it'sjust our generation and they
were bigger.
SPEAKER_03 (35:45):
It seems so unlikely Keith Richards would still be
kicking at this phase, right?
SPEAKER_01 (35:49):
Exactly.
Exactly.
But this is like the third timesomebody's brought it up as an
example.
I'm like, well, there'ssomething there to it.
SPEAKER_03 (35:55):
Yeah.
SPEAKER_01 (35:56):
You talk a little bit about the the wisdom
approach, right?
We have this amount of wisdomnow, or wisdom brand, I think is
what you called it.
Yeah, but oftentimes people say,well, I'll just volunteer or
I'll mentor.
Why is entrepreneurial ship sopowerful instead?
SPEAKER_03 (36:12):
Yeah.
This is a really fundamentalquestion that comes up a lot of
times, and it's well intended.
And I think what you find isthat people that were uh it
really invested in their careersor in their work with their kids
or whatever, when that goesaway, presumably we're in a
better financial situation thanwe were when you were younger.
(36:34):
We have more capacity, and wethink, well, I I can give more
now.
There's this, it's calledgenerativity, is the term.
It was by Eric Erickson, thepsychologist, and it's this
compulsion we feel to give backas we get older.
It's wired in us.
And so I think that that's wherewe have to really look towards
(36:55):
what is that going, what's goingto scratch that itch for us,
right?
How are we going to find ways togive back um that are still in
line with our values and ourpriorities and what's driving us
at this point in life, and notend up spinning our wheels doing
things that seem like they'd beinteresting, but that we don't
(37:17):
feel really passionate about?
Does that I may have gotten offtopic.
So that answered.
SPEAKER_01 (37:23):
Yeah, you're right there.
Yeah, right on, spot on withthat.
It's it's this has been afascinating conversation.
I think one that's beenhopefully super powerful for
people who uh will listen tothis episode because it is such
a good example of what'spossible once the kids leave
home.
(37:44):
And before I let you go, I I'mjust curious, what's one thing
you've learned about yourself indeveloping and creating Encore
Career Lab and your journey?
SPEAKER_03 (37:59):
It really lights me up seeing what people have to
offer and seeing them discoverthat.
And and it's there's a variationof that from wealth management,
but it's not exactly the same.
And the people that come intothe program have so much
potential and and they don'tappreciate it, they don't see it
(38:20):
a lot of times.
They're humble people and theyunderestimate themselves.
So it's really energizing to meto see them start to get excited
about that because thedownstream effects, the
butterfly effect, you just younever know.
SPEAKER_01 (38:34):
Yeah, the ripples and ripples are out there, and
who knows if you inspiresomebody else.
SPEAKER_03 (38:40):
Just one person, who knows?
Who knows?
That might be the one personthat changes the world, right?
SPEAKER_01 (38:45):
I believe that 100%.
Impact one or impact onemillion, there's no difference.
Impact is impact.
And when the kids leave home, Ithink we can still impact the
lives of others, just not ourkids.
SPEAKER_03 (38:57):
Yeah, absolutely.
SPEAKER_01 (38:59):
Jack, thank you so much for being here today.
The conversation was fantastic,and I look forward to seeing how
Encore Career Lab continues togrow and shine a light on what's
possible for folks.
SPEAKER_03 (39:10):
Thanks, Jay.
I appreciate the invitation.
It's been great being on, and Ilove what you're doing, so keep
up the good work.
SPEAKER_00 (39:16):
Thank you for listening to this Empty Nest
Life.
Remember, this chapter isn't anending, it's an invitation to
redefine, rediscover, andreignite your life.
If today's episode sparkssomething in you, don't forget
to take that first step andvisit thisemptynestlife.com and
click work with me to get theconversation started.
Until next time, keep your heartopen, your mind curious, and
your spirit shining.
(39:39):
This Empty Nest Life is aproduction of Impact One Media
LLC.
All rights reserved.
Popular Podcasts
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.
The Brothers Ortiz
The Brothers Ortiz is the story of two brothers–both successful, but in very different ways. Gabe Ortiz becomes a third-highest ranking officer in all of Texas while his younger brother Larry climbs the ranks in Puro Tango Blast, a notorious Texas Prison gang. Gabe doesn’t know all the details of his brother’s nefarious dealings, and he’s made a point not to ask, to protect their relationship. But when Larry is murdered during a home invasion in a rented beach house, Gabe has no choice but to look into what happened that night. To solve Larry’s murder, Gabe, and the whole Ortiz family, must ask each other tough questions.