How Sara Blakely Built Spanx and Found Her Next Big Purpose

What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?

In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business.

Timestamps:

00:00 Intro

01:56 Family background and kids

03:47 Childhood struggles and early mindset shift

06:32 Discovering Wayne Dyer and self-growth

09:00 Letting go of law school plans

09:46 Intuition and coping mechanisms

13:25 Selling fax machines and rethinking her path

14:17 The idea for Spanx is born

18:40 Building Spanx and landing Neiman Marcus

22:37 Growing Spanx without advertising

25:30 Selling Spanx and facing an identity shift

31:51 Midlife change and grief

34:44 Creating Sneaks brand

43:54 Psychology behind the second venture

47:32 Perimenopause, health issues, and PMDD

50:19 Modern Elder Academy experience

53:37 Focusing on presence and meaning

55:42 Introverts, extroverts, and integration

58:17 Feminine energy as a superpower

59:42 Wisdom bumpersticker

1:02:26 Chip’s final thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

#SarahBlakely #Spanx #FemaleEntrepreneur #WomenInBusiness #EntrepreneurLife #BusinessSuccess #Motivation #Inspiration #FounderStory #StartupJourney #MindsetMatters #SuccessTips #BusinessAdvice #SelfMadeWoman #EntrepreneurMindset #ChipConley #MidlifeChrysalis

Episode Transcript

(00:00):
What you don't know is your greatest asset because it means
you're not going to do it like everybody else. 80% of my mental
share for 21 years was on Spanx.I just wanted my mental share to
be freed up. But it just became clear to me
that I became more interested inwhat my mind would be thinking
about if I didn't go through my whole life owning this.

(00:22):
The more you experience in life,the more you have to offer
others. Welcome to the Midlife Chrysalis
Podcast with Chip Conley, where we explore how midlife isn't a
crisis, but a chrysalis, a time of profound transformation that
can lead to the most meaningful chapter of your life.

(00:42):
Welcome to the midlife chrysalis.
I'm Chip Conley and I had the most delightful conversation
with my friend Sarah Blakely. She is the first female person
made billionaire in the world. She is delightful in the sense
that she sang Sarah's smile on this episode.

(01:04):
It's her. It is her anthem that gets her
through the hard times. She talked a lot about what it
was like to have an identity, inthis case an entrepreneur who
started Spanx, the women's clothing company.
And when she sold it at age 50, she felt a little lost because
that identity, that midlife identity crisis of letting go of

(01:28):
something and not not knowing what's next.
So it's a very thoughtful and humorous and deep conversation.
I think you're gonna enjoy it. Sarah is a big fan of MEA.
She has both been at the MEA Campus in Baja, as well as
bringing her 11 best girlfriendsfor their annual vacation at the

(01:50):
MEA campus for a private retreatfor 54th birthday earlier this
year. So I hope you enjoy it.
Sarah Blakely, we're catching you after having spent the
weekend with Laser Laser's, youroldest son, is that right?
And four other boys. And it was just you and the five
boys going to Clearwater, FL, where you grew up.

(02:10):
What was that like? I mean, just tell me, when does
the, like, the prefrontal cortexlobe close?
Like, isn't there like, I mean, oh, my God.
I have to be honest. I kept saying underneath my
breath the whole weekend. Dumb and Dumber.
I was like, yeah, dumb and Dumber.
Yeah, OK. Dumb and Dumber.
I mean, they were like, Mom, we want to big dig a giant hole in

(02:32):
the beach. I'm like, OK, so they all, they
all got shovels and they dug forlike half a day.
And that was thrilling. And then, you know, it's just so
cute that they were actually really great boys.
They were super into the wake surfing, the the, the fishing
and being able to bike around the beach.
And as a parent, you know, you're on the precipice of your
child having a lot more independence, which is wonderful

(02:55):
and also scary. And I'm sure every parent feels
this way. You're like, have I done enough
to prepare this person to make good decisions while driving and
with this new found independence?
And I, I think I think so, but it's just scary.
It's like it's like the first version probably of them leaving
the nest. Mama Blakely, you have 6 kids in
my counting and I and I'm counting the two s s Spanx is

(03:20):
what, now 25 years old and Sneaks is maybe two or three
years old. Sneaks.
Is not even a year old yet, Chuck.
I know we're going to talk aboutthat.
So in between you had Laser, youhad the twins, Charlie and
Lincoln, and then you had your daughter Tepper.
Is that correct? I had my first child at 38, I

(03:41):
have four children and I got married for the first time and
only time at 37. So there's in yesterday on
Instagram and let's be clear, you have about a million
followers on Instagram, your coffee cup and everybody knows
you have famous copy cup. My only the only thing I've got
is like an ad. I know that one.

(04:02):
You can't change the cards. You were deal, you were dealt
you just just the way you can play the hand.
So what? What kind of hand were you
dealt, my dear, and how did you play it?
In life I was dealt a really good hand.
I mean, I really was. I feel like I was dealt A wildly

(04:23):
imaginative brain and an inner confidence that really was.
So I'm so grateful for. I grew up on a 2 1/2 mile long
sandbar called Clearwater Beach and I grew up on the South end
of the sandbar. And, you know, I didn't realize
it at the time, but I had probably all kinds of learning

(04:45):
glitches that now would be diagnosed probably with, you
know, ADHD and dyslexia and all the things.
But I just remember school was tough for me as far as reading.
I couldn't really read and retain what I read.
So I obviously had to learn different ways of, of of
retaining information and learning.
But the one thing that I really did at an early age, Chip, was

(05:08):
started working on my mindset. Like I became an absolute
student outside of Clearwater High and outside of school
because we all know it wasn't taught in school on how to
manage my own thoughts and how to manage in particularly my
negative self thoughts. You know, it started for me with

(05:28):
Wayne Dyer. So I feel like I was dealt a
certain hand. You know, I grew up in a
hometown that's like really proud that it's the hometown of
Hulk Hogan. My husband who grew up on Long
Island were like in the womb. They were asking what Ivy League
school their their kids were going to go to.
I mean, I grew up on a beach where I was like, are you going
to go to college? I don't know where you.
And so every time Jesse comes home to visit me, he's like,
sweetie, don't take this the wrong way, but the fact that

(05:50):
you've amounted to anything is even more mind blowing after
seeing where you grew up. Because it was a beach and it
was like. You had a pretty ambitious
father and, and, you know, and, and and an artist's mother that
was yours through the mix of both.
My dad was a trial attorney. You're right, he was a
litigator. He's a very strategic thinker

(06:11):
and my mom was an artist and a stay at home mom who is very shy
and soft spoken and I would say,you know, struggled with self
worth for most of her life. And, and I am a blend of both
for sure. I got, I got both the creativity
and then the ability to kind of think a few steps ahead.

(06:32):
One of your favorite Wayne Dyer quotes is nothing will matter
more than your opinion of yourself.
Do things that make you proud. Be kind, track yourself up that
feels right. How did you get introduced to
Wayne Dyer? So I was a sophomore, I think I
was either a freshman or a sophomore at Clearwater High,
and my dad and mom were separating.

(06:55):
And when my dad was moving out of the house, he came into my
bedroom Chip and he handed me a cassette tape series in a book.
Oh, you told me this in in Baja.Tell me.
Tell everybody else. So he handed me a cassette tape
series with 10 cassette tapes inlike a plastic binder that you
opened. And on the front it said how to

(07:15):
be a no limit person. And he's handed them to me.
And he said, sweetie, I wish I was your age when I discovered
this instead of the age of 40. And then he left.
You know, I always tell people that really dark times always
have a hidden blessing. And that was a really tough time
for me as, as a, you know, a 1516 year old.
But I was willing to listen to those cassette tapes because I

(07:38):
was hurting so much. So my hidden blessing was I was
open and pain and growth. And you know this better than
anyone. Times of transition are ripe for
growth. I think any other 15 year old
that was handed this middle-agedman with no hair and a bushy
mustache saying I'm going to change your life would have
chucked it in the bottom of their closet.

(07:59):
But I was like, I'm in a lot of pain.
I'm going to put this cassette tape in and see what happens.
And I sat on the floor of my bedroom and I started to cry.
And I thought, I have just spent16 years of my life in school
being taught what to think, and no one has ever taught me how to
think. Yes.
And I just wet it, like, wait a minute, what?

(08:22):
Like, I can be in the driver's seat of my thoughts.
I don't have to be in the back seat.
I don't have to be the victim oflike, whatever's coming in.
And maybe I can learn how to harness these thoughts in a way
that propels me forward instead of holding me back.
Anyway, I started hearing this man talk about manifesting what
you want. Law of attraction visualization,
not caring what other people think about you, not fearing

(08:43):
failure. And as a 16 year old in high
school, like that was pretty profound.
And I mean, pretty much the onlything 16 year olds care about is
what other people think about us.
So you're this man come through my, you know, boom box in my
bedroom. I was like, whoa, I feel like I
was being given the secrets to the universe.
You know, it's, I think more of us in as we're growing up need

(09:04):
those kinds of influences. I mean, they, we don't usually
get them from our parents, but you got them, you know, by proxy
from your father, which is, which was beautiful.
And then you want, you went on to college at FSU, Florida State
and and you decided the law school was not going to be for
you. Not once, but twice.
Chip. I'm a terrible test taker, which

(09:24):
for me at the time was really tragic and hard for me to wrap
my head around because I was a champion debater.
I had debated all through high school, all through college.
We were like national champions at Florida State in debate.
I knew I would have been the most epic lawyer, but the
universe was nudging me and letting me know I'm off course
because if the only thing that would have stopped me from
becoming a lawyer was failing nails at.

(09:46):
So you said the universe. So let's talk about that for
just a minute before. I mean, we're going to get into
your career in a moment, but theuniverse is, is, is like sitting
on your shoulder a lot of times and, and whispering in your ear.
And what recommendations do you have for people to be as much of
A conduit as you can be of something to come through you in

(10:09):
terms of little voices and, you know, without making yourself
feel like you're crazy, like, how does the how does the
universe come to you? OK, well, first of all, it's
been, it's been happening to me since I'm a little girl and
everyone has access to this. We have access to a universal
energy, knowledge, all knowingness.
And it's a channel. And I I kind of say it's like

(10:31):
the old fashioned car radios, you know where you would like
turn the dial fuzzy, fuzzy, fuzzy.
And then all the sudden like thesong would come in crystal clear
and you'd be like, yes. So I feel like that's what the
intuition, the inner knowing, these downloads that we get from
the all knowing energy field that only wants the best for us
happens. And the more that you listen to

(10:52):
it and the more that you honor whatever those fleeting little
thoughts or questions that you asked were, I think the stronger
the connection gets. So let's start when I was
little, when I was little, I really don't know why, but I
started creating a mechanism formyself to feel more comfortable
in my humanness. I was like a little bit freaked

(11:15):
out that like, how did we get here?
And I had a lot of existential thoughts from a very early age.
And I've had a few and I'm shared this with you,
existential crisises in my life,which are pretty profound
periods of I guess you would call it like rumination and and
can be depressive thoughts around like, why are we here?
Where did we come from? What is this all about?

(11:37):
I think as a very early age, I started creating good luck
symbols for myself that told me that like this team of angels,
light, whatever you want to callit, the universal energy, God
was looking out for me through asong.
And then my lucky number. I kind of created coping

(11:57):
mechanisms as a little girl. I was like, OK, you know, I'm
scared and I, you know, I feel like I'm kind of on my own here
in a lot of ways. Like if, if I'm on the right
track, if I'm here for a reason,if I'm doing the right thing.
I remember having those thoughts.
Show me the number 27 or play this, play the song Sarah's
Smile. That's my Good luck song from

(12:18):
Daryl Hall and John Oates. And then, like, it just started
like that. And then I started, you know.
Will you sing it for us? You want to sing the opening
lines I. Have the worst voice ever.
But yes, I will. But won't you smile a while for
me? Sarah, Sarah smile.
It's so good. It's like a song that came out
in the 70s and as a little girl I was like, OK, this is people

(12:41):
are trying to communicate with me through this song.
When I hear it on the radio, it means I'm safe, I'm on the right
track. So then I started asking the
universe questions around it. Then I'd be very specific.
I'd say, I'm not sure if I'm supposed to do this or, you
know, should I go to camp? Should I not, if I am supposed
to go to camp, show me the number 27 and like make it quick
like in the next day or two. And then I would start to kind

(13:04):
of frame decision making around this.
And I've been using signs from the universe to make key
decisions throughout my life, mywhole entire life.
Wow, and you are 27 * 2 these days.
You're 54, if I'm not mistaken, in fact, that you had your 54th
birthday party with 11 friends here at our Santa Fe MEA campus.
But I'll. We'll come back.
We'll come back to that. I want.

(13:24):
Let's go back to. OK, so you didn't go to law
school. You start selling fax machines
door to door, which I bet you were pretty persuasive.
I hope you didn't have to carry them with you, did you?
I. Did.
Oh, Jesus. In pantyhose, in high heels, in
Florida in the summer. Oh my God.
So I was the delivery departmenttoo.

(13:46):
So I would, I wouldn't always have them with me walking in the
door. I'd walk in the door and go,
hey, I'm Sarah, you know, do youneed a fax machine?
And they'd usually escort me outof the building or RIP out my
business card and say no. So listening.
But for the few accounts that didn't, I would, I would try one
and I'd go back to the headquarters, get the fax
machine, put it in my trunk and then drive it there and then

(14:09):
carry it in and like crawl on the floor and plug it in and
learn how to set it up. It was so stop.
Remember that part being so stressful?
Wow. OK.
So how you did this for not justlike a month or two, you did it
for an extended period of time. Seven years.
Ship man seven years. And during that time, you

(14:29):
realized that your pantyhose were, you know, in a bundle.
You didn't. It wasn't.
It wasn't comfortable, and so you decided to create your own
little version of what ultimately became Spanx.
You sort of prototyped it. What do you call this?
What do you call the Spanx? Do you call them?
Shapewear or. Shapewear.
So here's the deal. You're cracking me up.

(14:50):
I got interviewed by Coach K from Duke.
This isn't this isn't you. But I love it when men are
interviewing me about spank. Coach K tried to interview me
for a new show we was doing for like 40 minutes without saying
the word panty. And so finally I looked at him
and I'm like, panty, It's OK. You can say he turned bright
red. I was like, this isn't your

(15:12):
wheelhouse, isn't Coach K. And he was like, no, it was
cute. Anyway, I I'll tell you what I
did the sound bite in the media chip for 20, five years now was
Sara Blakely cut the feet out ofher pantyhose and Spanx was
born. But what wasn't in the media was
that I set the intention for this years two years prior.
So I was 25 years old. I was had just been kicked out

(15:35):
of a lot of offices, cold calling fax machines.
It was a particularly bad day. I pulled off the side of the
road and I remember thinking to myself, I'm in the wrong movie.
Like I'm in the wrong movie called the producer, called the
director. But this is not my life.
I I need to, I don't want to be the star of this movie anymore.
So I went home and I wrote, whatthe hell are you good at, Sarah?

(15:57):
Like what? Where?
What are your possibilities like?
And so the only thing in my goodcolumn was sales.
And I asked myself a really important question.
Instead of just identifying thatmy strength was sales, I asked
myself why. And if I hadn't asked myself
why, Chip, I would have gone to get another sales job.
I would have left Danka and goneand sold something else.

(16:19):
But by saying why do I like sales?
And why am I good at this? And why is this a strength I
uncovered? Oh, wait, I really like selling
something or giving something tosomeone that changes their life,
improves their life, or makes them feel good.
Like I had already seen the businesses flourish from me
selling them this fax machine right before that.
It was like snail mail, right? And then all of a sudden I'm

(16:40):
showing them this machine where you put the paper in and dial A
number and whatever you wrote, it could go to China.
Magic, magic. I remember it was so crazy.
It was so crazy I was selling fax machines so early on chip
that my biggest objection was, well who in the hell am I going
to fax? Well, you do need someone on the
other end to fax it to, right? I mean, it's like, you know.

(17:01):
So I set the intention and and then I said why?
I knew that it's because I lovedoffering something to someone
that made them feel better or change their life.
And then I had this epiphany. Well, why don't I create my own
product? Wouldn't that be the most fun
journey instead of selling someone else's product?
I had no idea what it was going to be.
Chip, I wrote down, I want to invent something that will
change millions of people's lives for the better.

(17:23):
And then I said, universe, give me the idea and I will not
squander it, like, show it to me, have it arrive.
And it was two years later that I was getting ready for a party
and I couldn't figure out what to wear under white pants
because all the undergarments showed.
And I called my friends who weremodels.
And I'm like, guys, you're in these ads.
What did you wear under these pants?
Like, I bought the pants and they're hanging in my closet.
And they're like, oh, we're airbrushed.

(17:44):
I was like, OK, that's great. But what is the, what is the
average woman at home supposed to do?
Doesn't have an airbrush, you know?
And that's where Spanx was born.I, I came up with a
revolutionary new type of undergarment.
I took something that it existedforever, 70 years, which was
pantyhose, but I cut the feet out of it.
And the reason I wanted to use that material chip was because
it was so thin. It was like tissue paper.

(18:06):
So it didn't add bulk to what you were wearing.
And it was breathable and it waslike a second skin.
So it created this perfect canvas for all of your clothing,
whereas anything prior to Spanx was thick, hot, flawed, left a
big liner bulge on your thigh where this big leg band was.
And then came this, like this product that had already existed
in one medium. And it took me a long time to

(18:28):
convince the men like, no, I don't even want to see the
pantyhose because they're like, it's always supposed to be seen
on the leg. This is why we're making it.
I'm like, I want to, I want to repurpose it and create an
undergarment with your material.So how did you do that?
I mean, you're, you're not like a product person, you know,
you're selling fax machines and like, who did you go to to like

(18:48):
prototype this? You did it yourself, I know
initially. But like, how did you get to the
point where you know you could create that very thin layer for
the form, the shapewear that youwere doing?
Well, because I was a consumer of it, I had to wear it as my
dress code selling fax machines.So I knew how lightweight it
was. I knew the like slimming and

(19:10):
firming and smoothing effect it had on me.
So I thought if I could just have like an undergarment that
no one sees made out of this material that didn't leave lines
or bulges or anything. I could wear white, I could wear
cream, I could wear silk, I could wear all these fabrics
that hang in my closet. I used the universal lot ship.
I mean, I had, I had five grand from selling fax machines.
I did not have a business class.I'd never taken it.

(19:32):
I didn't have contacts in the industry.
But I had the universe. And I, I started asking the
universe give me guidance. Is this my idea?
I asked for my idea. Is this it give me courage to
keep going. And I just started calling
manufacturers, looking them up on the Internet.
They were all in North Carolina.I wrote my own patent.
I bought a book at Barnes and Noble and wrote a patent.

(19:53):
Oh my God. Well, there's that legal.
There's your legal side of you. So it's just, I just honestly
fumble my way through it like most founders.
You know this. You're learning as.
You and you came up with the name too.
That wasn't that you were driving in your car, if I
recall. I don't know.
And you like the name came to you, Spanx.
The thing that's interesting about your story, Sarah, is that

(20:14):
it was almost immediately successful.
I mean, maybe there was a littlebit of time where you were not
you had some indecision about it, etcetera.
But no, instead, you know, you went out and sold yourself to
Neiman Marcus, going from fax machines to Neiman Marcus and
you were relentless. And then Oprah picked it up
pretty quickly. Talk about the time.
So we're going from, you know, your 2000 to 2012 because by

(20:40):
2012 Forbes called you the the youngest self-made, maybe the
only self-made female billionaire in the world.
Because also the thing that a lot of people need to know and
those of you who are business people out there, just just
think about this, you've self funded this damn thing.
And, and so talk a little bit about that period from 2000 to

(21:04):
2012. Along the way in 2008, you got
married to Jesse. I'm curious about that dozen
years and then Jesse showing up and and why it took so long for
a Jesse to come into your life as well.
I was pretty focused on growing this business.
I was self funded, so Spanx was solely funded by the five grand

(21:27):
that I had from selling fax machines.
Never had any outside investors for the whole journey.
I would say that I was really focused on three things.
I was like, make it, sell it, build awareness.
I didn't know anything else. I didn't know how to read a
spreadsheet. I didn't know anything.
But I was like, I've come acrossa product that I love that I

(21:47):
think it's going to fill a hole in a lot of women's lives and
wardrobes and let me find every avenue I possibly can to sell it
and let me find every way to build awareness.
So I've started calling TV channels and radio stations.
I, I went all across the countrydoing events in all the Neiman
Sachs, Nordstrom, Bloomingdale's, selling it

(22:09):
myself for them because once I got the opportunity to be sold
in their store, that's where I say most entrepreneurs might be
like I've arrived. I landed Neiman's and I was
like, I hit the road for two years and worked every day,
including Sunday's for two years, selling the product in
the store for them. Because I wasn't going to leave
the fate of my idea in the handsof people that were making, you

(22:33):
know, X amount of dollars in thesleepy corner of the hosiery
department of the store. Yep, you went, you decided to
cross fertilize. I, I was listening to you on
Hoda. Hoda was one of my first
interviews for, for this podcastand she's a good friend.
And so I learned from listening to that about the fact that you

(22:53):
went to all the departments because you didn't want to get
pigeonholed just in hosiery. Tell us more about that.
Well, I realized once I was standing in the store where my
customers were and I actually had a chance to sell to them,
that I was in the sleepiest corner of the store.
I was in the hosiery department where no one was going anymore.
Hosiery was kind of phasing out in society.
And I was like, wait, this is not hosiery.

(23:15):
This is an undergarment that's going to allow you to wear that
couture gown or to wear the really great strappy sandals you
want with the white Capri pants.So I went to the stores and I
bought stands from Office Depot and I put them at every cash
register at Neiman Marcus, whichhas the strictest visuals on the
planet. And everybody thought somebody
else approved it before they figured out that nobody approved

(23:37):
it. So I was doing everything I
could to get baby out of the corner.
You know, like nobody puts baby in the corner.
I'm like, I got to get Spanx outof the corner.
So wherever I could put it in the store, I did.
I won over all the salespeople. I did morning rallies every
morning across the United States.
And what I ended up doing was building a sales force not on my
payroll that were all rooting for me.
And also I was, I always say this, you always want to give

(23:59):
them a what's in it for them. So I would really make it clear
to the women who sold couture gowns, what was in it for them.
And then the win the men and thewomen selling the shoes.
And I was like, you're going to sell more shoes, you're going to
sell more gowns, you're going tobe able to sell these clothes if
you tell your customers about Spanx.
And it just took off from there.It was very organic.
You know, I built this global brand and it became a household

(24:22):
name without advertising chip. So Spanx didn't spend any money
on advertising for 16 years. So it was just a lot of me being
willing to tell the story and the why I say people are far
more interested in the problem you're solving than the product
you're selling. And I LED with the problem,
which was men had been making our undergarments for a really

(24:43):
long time and they were a littlebit dysfunctional and not super
comfortable. And so I was really determined
to give women better options. And then also, you know, I, I
was determined to explain why itmattered to me.
And I think that that really made a, a lot of women want to
share it with other women. Because if you think about what

(25:04):
I invented, nobody saw it on topof me having like no budget, I'm
going against Haynes and Sara Lee, these billion dollar
companies. I'm out of my apartment, I have
5 grand. No one sees my product, so it
couldn't become this viral moment of like, hey, what are
you wearing? Well.
Unless they flash it at you. Which they do.
But it took women sharing it, and for the first time ever,
women on the red carpet started saying, hey, I'm wearing

(25:27):
something called Spanx underneath my gown, which had
never happened before. Amazing grit and grace.
There's a this beautiful combination, Sarah, of grit and
grace and tenacity and grace. I love it.
But at almost 50, you and I havesomething.
We have a few things in common, but one of the things we have in
common is that we had this thingthat we loved for you.
You were, I've been running it for 21 years.

(25:49):
I think at that point for me with my boutique hotel
companies, you want to leave. I've been running it for 24
years, had 3500 employees at that .52 hotels at 50, both of
us decided it's time. And so maybe talk a little bit
about that. You decided to sell the majority

(26:10):
share to Blackstone, I believe, if I'm not mistaken, huge
private equity firm and what ledto that?
And then I actually started to get to know you after that
because guess what, you had had an identity since your late 20s
that you'd and for me it was since the age 26.
And I know how hard that is whenyou have lived your life around

(26:35):
this identity and you now don't have the identity anymore,
although you did. You certainly did, but you
didn't have the decision making.You were in a whole different
era. So talk about that process.
Why did you decide to sell and what was it like?
Because that was a bit of a midlife chrysalis for you.
That's how I found you. That's how you found me.

(26:58):
It was ritual, I believe that was interviewing you.
I was in significant amount of grief and pain and really
searching and feeling like I needed guidance.
And then I hear you on a podcast.
So I had no idea what MEA was Modern Elder Academy.
So I Googled it after I listenedto your podcast and I signed up

(27:20):
and I went for seven days. Didn't know anybody, but I loved
that someone was taking midlife and trying to reframe it and
saying, wait a minute, like are we doing enough in society to
prepare people for this massive transition?
And that happens around the age of 50.
I mean, you've listed him at your workshop, but it's like you
become an empty nester a lot of the time.

(27:41):
You have aging parents. You might be re evaluating your
career or your career might be coming to an end.
I mean there is a cataclysmic oflike mush that happened.
And perimenopause. Come on, let's like.
That is so brutal. Yes, So, and for a woman, your
hormones are radically changing.So for me, it was a lot.
And to answer your question about Spanx, I, I had been asked

(28:05):
for the, since I started it, what my exit strategy was.
And I didn't know what an exit strategy meant.
Like I'd never taken a business class.
So all these guys are asking me six months into me starting,
what's your exit strategy? So what's your I was like?
And so one day I just go my exitcharges.
I want to exit a room and look good.
That's it. And that became my tagline

(28:29):
forever. And it just kind of blew it off
and I didn't take anybody seriously that was interested in
buying Spanx. And then I kind of started
going, oh, what is my exit strategy and what does that
really mean? And you know, to your point
about identity, I am the Spanx girl, like Spanx.
And Sarah Blakely, like most people who meet me, they're

(28:49):
like, oh, you're the Spanx girl,right?
So and partly that happened because I had no budget to
advertise. So I was the advertisement like
me telling my story of my why became this very meshed fabric
of the foundation of the companyin culture.
So I, I always tap into intuition and I kept saying to

(29:10):
people, I'll just know. Well, for I would say many
years, this was not quick. This was many years in the
making. I kept getting this, what I call
this little tap. It's like knowing.
And what I like to say is I feellike spirit was tapping me.
OK, and ego is going like this ego was like, not now, whatever.
And spirit was like, OK, OK. And so I could no longer ignore

(29:33):
this tap that kept coming from Spirit, and spirit knew that I
needed to move on in some way and let go in some way, right?
And the reason, the core reason why I sold was not for money.
Spanx was very profitable. Literally from the first month
in business, I was profitable. Just, you know, so wildly

(29:56):
interesting. Now that I learn a lot more
about business, I am like, oh wow.
But it was also because I was bootstrapping it so much.
I just wanted my mental share tobe freed up.
I wanted two things. I wanted to experience having my
mind wander more easily to something else.

(30:17):
And I knew intuitively, and somepeople can do this.
I knew I couldn't I 80% of my mental share for 21 years was on
Spanx and I had to make a decision.
Sarah, you love this so much. It's basically your first child.
Like you birthed it, you grew it.
You've spent every waking ounce of your life souls work on

(30:37):
building this for the consumer and honoring the consumer and
honoring the team that you've built here.
But, you know, it just became clear to me that I wanted, I
became more interested in what my mind would be thinking about
if I didn't go through my whole life owning this.
And that's hard because it's, you know, that means you have to

(31:00):
turn it over to somebody else. That means you have to be
willing to sell it. And when I made that decision
that I wanted to free up my own mental share to see where it
goes, what would I dream of? What would I think about?
Where would I be? Like, I remember specifically
sitting on the road chip and going, if I don't sell Spanx, I
kind of know in five years from now what I'm talking about, what
I'm thinking about, the meetingsI'm in and what I'm discussing.

(31:25):
And if I sell Spanx, I don't know.
And that became more interestingto me.
But man, it put me through the, it was so hard to let go of
something I love this much. I still own a big chunk of it.
So I'm still the chairwoman of the board.
I don't own the majority, which was important to me because for

(31:45):
me to achieve free mental share,I knew I had to give up control,
which was hard. I mean, you know, it was very
hard. It was, it was, I mourned it.
And I told you this at the workshop where I told everyone
there, it's not on society's checklist of grief when you sell
your company for a lot of money,right?
Most people are kind of like, wow, great, congratulations.

(32:08):
And then you get the barrage of like, so what's next?
Or, you know, why did you sell it?
And at that time, I was in such a vulnerable emotional state.
Those questions were very triggering for me.
But I operate in quotes and the three quotes that best describe
my 18 months that I got put intofight or flight mode with my

(32:28):
nervous system after selling wasin order to discover new land,
you must be willing to lose sight of the shore.
And it can be really uncomfortable when you're out at
sea and you do not see land, especially when you just jumped
off of like a really safe, comfortable big boat or
whatever. That's pretty predictable.
You're like, why did I do that? And then the second quote is you

(32:49):
can miss it and still not want it back.
And the third quote is you can make the right decision and
still be sad. And the sadness you had to
honor. And as is true for many
entrepreneurs, when I sold my companies, you want to be even.
It's a Hyatt brand now, JDV. There was just the fear of the
unknown, but there was also the excitement of that, but there's

(33:13):
also sadness. And I realized that in many ways
as an entrepreneur, I had been out running my emotions.
And that may sound familiar to you.
I there I was like, there were emotions that I was out running
and I was like, oh, wow, now I have to deal with that.
I, you know, that little that that work addiction.
I think I've got OK, where what am I going to fill in the space

(33:34):
of that? And the good news is that I, I
took what and you did too, what we call an at MEA, A midlife
atrium, the idea of some space to reimagine and repurpose
yourself. Because quite frankly, in a
world in which longevity is realand we're living longer lives

(33:54):
and we don't really have a, a road map to understand midlife
and beyond. It's not, you know, the
additional longevity is not likean extra bedroom in the backyard
of life. No, it's looking at your midlife
and asking yourself, how do I want to consciously curate the
second-half of my life? And I did that for two years
from 50 to 52. You did it around the same time.

(34:15):
And for me, I ended up getting acall from Brian Chesky saying,
hey, Chip, in fact, you and Brian, I think we're hanging out
together. Not long ago, Brian Chesky
called me and said, like, I'm this, you know, this is 13 years
ago. We have this little tech startup
that we want to be a hospitalitycompany when we grow up.
And will you come in? And ultimately, he called me the
modern elder and he said you're as curious as you're our wise.

(34:36):
And that's what happened in my midlife atrium.
What happened in your midlife atrium is you got to spend some
time with the family. You went on some Rd. trips and
then there was this idea that you'd had that you and you were
the customer that started to sneak into your consciousness.
And the next thing you knew, youwere like excited.

(34:57):
And then you also put it on holdfor a little while.
Talk about the sneak story. One thing that I just want to
honor and say about that transition, when you said, you
know, there's a lot of emotions that you may have been run, not
not even intentionally running from, but that fuel us, right?
There's so much fuel that happens.
And I learned this at your Academy.
You know, the first part of lifeis proving and then you move

(35:22):
into improving and improving is less outward facing and more
inward, which is a huge shift. And I will say the thing that I
felt the biggest shift for me with was I was in major prove
energy and I have been improvingenergy since I was 3.
Like, I have this and I think a lot of it has to do with, yeah,

(35:44):
I mean, everyone's different. I'm curious what yours was.
I mean, I, you know, a lot of times it could be like proving
to a parent, but for me, I was literally proving to patriarchy.
I remember being three years oldand having like on a cellular
level going, wait a minute, thissomething doesn't feel right,
Like this doesn't feel right. Like my mom's role and the women

(36:04):
that I knew this just I, I, I was like, I felt a deep desire
for women to be elevated and to be honored in a different way of
then and for them not to dim their lights, including my own
mother. And I felt also like I deeply
wanted the respect of men. I didn't really want the

(36:26):
attention. I mean, the attention was fine
and felt good, but I was like, Ireally want the respect and I,
and, and so for me to, to be spending so much of my energy in
my life proving. And yes, there's also the whole
component of like, I deeply wantto honor women and give them
better options. And I love using creativity to
come up with products to do that.

(36:46):
So there's that. But when you don't have anything
left to prove technically, like who are you?
And I was just sitting in this midlife moment going, if I don't
have anything else to prove, like am I going to be motivated
to do anything? And like, if I, if I don't have
to prove something, what why do I do anything?

(37:10):
And who am I in that way? And it like, so I was really
trying to excavate like, what doyou want to do just for joy?
Or what do you want to do just for like, and that I'm still
working on that, you know, like it's an interesting thing.
And for me as a woman, I had a lot of momentum around proving,
proving and like living the lifemy mother didn't really get to

(37:33):
live. And my grandmother's and
wanting, you know, deep respect from my dad in a way that was
different than I felt that he felt towards my mom and other
women in his life. There's just a lot there.
But moving that aside, I had this dream and vision to also
invent a comfortable high heel. And I have been saying that for
10 years publicly. And I kept lobbing it out like,

(37:56):
someone please do this. I'm in a lot of pain.
I love wearing heels, but they hurt my feet and after after 10
years, nobody took the bait. I still as a consumer could not
find a high heel that felt comfortable to me.
And so I decided to ask the universe for a sign.
The universe delivered a very clear sign to me and I said OK,
I'll do it. I'm going to try what was.

(38:16):
It Can you tell us what the signwas?
Yeah, there were two signs. It was crazy.
So real quick, I finally woke upone day and I was like, I've
been saying this for a while, Universe, am I supposed to be
the one to try this? Like if I am give me a really
clear sign and I always say thisto the universe and I go and it
can't be a rainbow. Like it has to be really
specific. So like 2 days later I flip on

(38:37):
the Morning News and it was Gayle King interviewing a shoe
designer on hard news, which wasalready weird, right?
Like in the morning it's hard story.
So I was like, oh, I just asked for a sign.
That's weird. She's interviewing the shoe
designer. She picks up the shoes, she
goes, listen, I love your shoes.They are a work of art.
But I got to tell you, by the end of the day, I could be
crippled and as a product personwho spent my whole life trying

(38:58):
to make the consumer, especiallywomen, feel loved and supported
and valued in how they feel and not just how they look.
He looked at her and he goes. I do not want my shoes to be
comfortable. Oh God.
And then he said, in fact, if someone tells me that my shoes
are comfortable, I take it as aninsult.

(39:20):
So I was like, all right, OK, universe, not only do they, are
they not working on it, which I tricked my brain into thinking
I'm like, they don't care. So I'm going to stand down and
raise my hand and know nothing about shoes the way I knew
nothing about undergarments. But I want to like raise my hand
on behalf of women and see if I can give us a better option. 10
years, lots of trial, getting fired from factory after factory

(39:42):
in Italy and Spain. I launched Sneaks, which ended
up being a hybrid of sort of like a sneaker and a stiletto.
And I wanted to start with stiletto chip because it's the
least comfortable, right? Like I like starting with the
worst problem. Like for me, it was like
girdles. I was like, these stink like I
need to make this more comfortable.

(40:03):
So I ended up merging a classic sneaker.
I solved 3 pain points really quick.
I widened the toe box for the woman's toes.
I redistributed the weight high heels since the 1700s without
much change, Chip. 80% of the weight is on the ball of our
foot and 20% is on the heel and I redistribute it.

(40:24):
So when you're standing in the heel, even though you're in a
three inch stiletto, you almost feel like the weight is 5050.
So you don't get all that pressure on the ball of your
foot. And then I gave whole foot
support, whereas in traditional high heels, it's usually kind of
suspended here and here and I filled it in and gave the whole
foot support. It is a mind Bender.
When you put my shoes on, they're called sneaks SN EE X.

(40:46):
But when you stand in them, you're in a three inch stiletto
and you're like, wait, I kind offeel like I'm flat on the ground
in a sneaker like is this reallyreal?
Is this happening? And I wanted to invent the
comfortable, the most comfortable stiletto. 4 years
into the journey chip. I had to pull the plug.
I told the team to make it look exactly like our high heels that
we were used to wearing, but be exponentially more comfortable.

(41:07):
We made it more comfortable, butit wasn't exponential.
So the two girls I'd pulled off onto the team from Spanx that
were broad designers that had dedicated 4 years of their life
to this. I said guys, we didn't get it
over the finish line. It's OK, we tried.
And as I was leaving the factoryin in Italy, I said I don't know
why this has been so hard. I just want my high heel to feel
like my sneaker or in the year of 20, whatever.

(41:29):
We shot a go Kart now to Mars and we're driving it by remote
control from Earth. Like what is happening?
Why is this so hard? And in the moment I said that
chip, I paused and I looked at my friends and they were like
Sarah no, Sarah no. And I went home and I cut my
sneaker in half and my high heelin half and glued them together
and walked around my house for three days.
You. Didn't break an ankle or

(41:50):
anything like that. No, I.
Didn't break an ankle, but I waslike, could I make this work?
This is really weird. But like this could solve a lot
of problems. And so I was willing to pivot my
innovation and my creativity. And the original brief, which
the original brief was, it has to look exactly like a stiletto.
And instead I've got one here onthe floor.
But like, it turned into this. And so, you know, there's a lot

(42:11):
of like there's so much more stability in the heel and women
are rocking them and wearing them in all different ways.
But I'm happy that I've given them for those who want it,
another option. That's all this is.
And it's changed my life becauseI I had to stop wearing heels
until snakes. I just want to call this out
because I, I think a lot of people are not familiar with
this, but when someone has a huge success as their first

(42:35):
thing that they do in the world,it gives them identity.
It gives them a sense of momentum.
In your case, you've stayed humble, thank God.
And my case, I think I did the same.
But you know, Elizabeth Gilbert,you know, famous for E Pray
love, good friend taught at bothof our campuses.
You know, when she had her success with E Pray Love, it was
really hard for her because everybody's thinking about the

(42:57):
follow up. What are you going to follow up
with? I was lucky because my follow up
was not starting a new business.It was going into an existing
small tech business that nobody had heard of and helping it
become very successful. So it was a little easier
because I was able to change my identity, although it did
require a lot of changes in my mindset.
I was no longer CEO. I was reporting to Brian, who

(43:17):
was 21 years younger than me, but I was also his mentor.
But in your case, you. This is a hard one because
there's an element of Sarah knowing.
I got off the ground in 2000 andwas immediately successful and
everybody, you know, and I was doing it and if I wasn't
successful, nobody would know about it.

(43:38):
But now I've got sneaks and everybody's watching me and
there's this element of like, oh, can she do it again?
So there's some pressure, but then at the same time, if you've
moved from proving to improving,maybe they're you're just like
laughing at yourself and the situation.
But talk a little bit about the psychology of what it's been
like to launch sneaks and the the upside and the downside of

(44:03):
doing this as the follow up the sequel.
So I had done enough work on myself.
I don't care at all about the second act or trying.
There's not an ounce of me that's trying to outdo the first
one. I recognize this for being very
different. I appreciate that other people
might be thinking about about that, but I am not.
I'll tell you where I paused andwhere I got really emotionally

(44:26):
worked up was is this going to take over my life?
And that was what I did not havethe answer for.
And I literally paused the launch an entire year.
And the reason that I did it, I had all the shoes.
I made no changes in that year to the shoes.
I had this small mighty team that was really excited about
launch. I'd already done 2 interviews
with Press Chip. They were like launching the

(44:48):
articles on like, that Thursday.And on Tuesday, I woke up in the
morning and I sat straight up inbed.
I clenched the sheets of my bed and I went like, it was almost
like I couldn't even breathe. And I go, it's not the right
time. It's just not the right time.
And I called my team and I was crying and there were tears.
And I said, guys, I'm really sorry, but it is not the right

(45:09):
time. And I need to push this back.
And they go, no problem, Sarah, no problem.
I think they were expecting me to say like in two weeks or a
month. And I said, I'm going to launch
it next year at the same time next year.
And there was like a breath. I'm like, guys, you know?
And what I wasn't clear about inthat moment was, am I doing

(45:30):
sneeze to fill this void of thisvacuum that I created?
Like, am I going to get on the same treadmill?
And am I doing the same thing? And how am I doing the same
playbook because I'm in this anxious space?
Or is this an honor? Is this an offering that I want
to make to women for all the right reasons?
And am I going to have the rightboundaries in my life to protect

(45:51):
it from becoming my life? And my husband kept saying,
Sarah, you're not the girl with the red backpack anymore.
You're like Sarah now at this age.
You have money, you have funds. Like this is going to feel
different. And I, I think I was so scared I
was going to leave my family andgo stand like selling shoes in
department stores for two years.I don't know what I thought, but
maybe just PTSD from how hard I work to get the first man off

(46:13):
the ground, you know? And then it's been nothing but
lovely. Like I put it out in the world.
It's an offering. It's doing phenomenal.
I've got a small little team that are really inspired to make
luxury high heels better and more comfortable and shoes in
general, right? Like I, I'm not going to just do
high heels. I started there because that's
the most uncomfortable, but I'm excited to play in this.

(46:34):
It gives my creativity and arena.
I care deeply about women and how they feel.
So it's checking a lot of boxes.And I, I launched with a product
that's really, you know, people have really strong opinions
about it, which I love. Like it created a lot of
conversation, love and hate, which no chip, you know this
whenever you're doing anything really truly disruptive that

(46:56):
comes with it. To me, that's a good sign.
Like no one was talking about itand half the country did.
Wasn't like, I'm not sure if I like this and what's going on,
then I don't think it would havebeen.
I would have been disappointed. What was the psychological shift
you had to make in that year to give you the breathing room?

(47:17):
Was it was it just realizing that you were in this in no
longer in the proving mode and and your definition of success
was just getting to the startingline and and you didn't have to
repeat the Spanx financial success.
What? What was it?
No, I was already there when I made that decision.
I was like, I don't. This doesn't have to be the next
spank. This can be a small cult

(47:38):
following. Like I was cool with whatever
this is meant to be. I have a lot more like universe,
you take this and make with it what it's supposed to be and
guide the right people to join this team.
Whereas Spanx was like, no matter what, you know, no matter
what, this is like, I'm making this happen.
And so for me, I also was not ina good emotional place.

(48:01):
Like I was still very grieving and I think I was still very
chemically imbalanced from perimenopause.
And I think I had no idea the severe impact perimenopause was
having on me because I just thought my mental state was
mostly a result of selling because it was such a big life

(48:21):
decision. And I couldn't see clearly that
the emotions and the imbalance and the sadness and the ups and
downs and everything that I was experiencing was actually
hormonal and chemical. So I went on a journey that
year. I traveled with my family and I
also spent a lot of time on my health and understanding what
was going on in in me emotionally, but I was in a

(48:43):
really emotionally tough space from perimenopause like I was.
I have I figured out like I had something called PMDDI think
it's called, which just means perimenopause on steroids.
Like a lot of women's estrogen starts to go like this in a
gradual decline, which causes a lot of, you know, symptoms and

(49:06):
can cause sadness, can cause allkinds of things.
I'm in this 10% bucket where my,my estrogen goes like this on a
way out. It's like going straight up and
then plummeting and straight up and plummeting.
So, you know, my, my symptoms were pretty severe and extreme
and I wasn't sleeping. And so then someone said, Sarah,

(49:26):
why don't you try something called progesterone?
And I started taking progesterone at night.
And within two days, I was like,Oh, well, that's weird.
I could sleep and I felt like myold self again.
And I was like, not crying all the time.
I was like, wow, I can't believeI went 18 months without taking
progesterone or recognizing thatthat could be playing a role.
I, I did have to deal with hormone depletion therapy

(49:49):
because of my prostate cancer, which means I, my testosterone
went to 0. So I had all of the physical,
not the psychological, but the physical symptoms of menopause.
So hot flashes, night sweats, brain fog, all of that.
So I have a ton of respect for women and I think all men should
have to go through menopause or perimenopause just because, you

(50:11):
know, guess what women women do so much.
So I have a couple last questions.
First of all, I just love you. I just love you.
I love you. Well, I want everyone listening
to know that I've been to both like you did.
Start another company after you're beautiful stint at a
small company called Airbnb, right?
You ended up creating Modern Elder Academy and I found you

(50:32):
through a podcast, but I went for a week to your location in
Cabo, which is an epic, beautifully done, of course,
with all the chip magic boutiquehotel right on the sand.
And I joined a group of like 30 people I didn't know and we
talked about reframing midlife and I had a wonderful, beautiful
experience there and it was wonderful.
And I still have great friends from that.

(50:54):
And then I liked it so much thatI surprised my core childhood
friends. And every year since I turned
35, so this was our 19th year. So when I started, I every year
on my birthday, I take 10 of my childhood friends away on a
surprise vacation. And they don't know where
they're going. It's a full surprise.
They all they're told is hot, cold or passport.

(51:14):
And that's all they know. And these are working moms, most
of them who never get, you know,they plan everything in their
life. They're exhausted.
And so I was like, when I was 35, I'm like, I have this new
success. What do I want to do with that?
I'm like, I want to spoil the people I love that wouldn't
normally do this for themselves.So it's been a tradition 19
years. And this year I surprised them
and took them to your new location in Santa Fe.

(51:36):
And he had an epic time. And it's had a profound impact
on all the women. But there's probably 3 or 4 out
of the 10 that I would say it has really, really shifted
things in a positive way for them.
Well, and one of them was your sister-in-law and between her
and you, they convinced your brother to come down to Baja and

(51:57):
I got to spend some time with him, with you.
What a what a beautiful man he is.
He's such a beautiful soul. My brother's more introverted.
He, he does not like, like social gatherings make him very
anxious. And he's very also analytical.
He's more, you know, he has an accounting degree and a finance
degree, and he spent five to sixmonths quietly thinking about

(52:19):
whether he would have the courage to go do that.
I didn't know and then he calledme Chip.
Do you want to know The funny thing?
Because I I had offered to send him like he could feel on his
own, but like I was like, I feelthis strongly about it.
I'll pay for it if you want to go.
And he was like, I don't think that's my thing.
I don't think that's my thing. And then I don't know where I
was. I think I was in Hawaii at a

(52:39):
girls retreat recently and he called and he goes to Sarah.
Chip's thing is tomorrow. And I'm like, what thing?
And he's like, you know, the MEAthing.
There's an opening and there's still an opening and it starts
tomorrow. And I was like, and are you
thinking about going? He goes, I am, I go, well, the
offer still stands. And, and then I, I, I was like,

(53:00):
but he decided the night before and he didn't want to tell
anybody he was thinking about itbecause he didn't want pressure.
He loved it. He had the best time.
But it's been very meaningful for him too.
I really recommend everybody go.He's a role model for for men
because, you know, a lot of men have a hard time getting
vulnerable in a personal go through treat workshop.
But often the men need it more, partly because women are so good

(53:22):
about communicating with each other about what's going on in
their life. And for a lot of men, I mean,
part of the reason I started MEAwas because I lost 5 male
friends to suicide ages 42 to 52during the Great Recession,
Three of them entrepreneurs whose businesses had gone under.
But so I want to two last questions.
One is one of the things we say at MEA is that, you know, as we

(53:42):
get older, time becomes the mostvaluable asset in our life. 10
years from now, what would you regret if you didn't learn it or
do it now? Because anticipated regret is is
a form of wisdom. Spend significant time with
friends and family in places that bring me a lot of peace and
happiness. Like I'm in a situation now

(54:03):
where I can spoil the people I love and I can coordinate things
where I can get family members and extended extended family
together that maybe wouldn't have happened if I didn't have
this opportunity. So I'm really going to lean into
that. I want to be in the present
moment. I want, I want to look back 10
years from now and say the last 10 years I was really present.

(54:24):
I don't know if you found this, but as a founder and an
entrepreneur, I had a very hard time being in the present
moment. I really did like I never really
mastered that. There's just 1000 things going
through my mind as an A founder and an entrepreneur at all
times. And things were being sent to us
like daily, you know, it's like being an entrepreneur, you're on
a in a mild state or a major state of fight or flight the

(54:47):
whole time because you're just kind of like bracing yourself
for what's coming. Do you?
And so I really feel like I was,I wasn't in the present moment
as much in the last bit of my journey.
So I want that to happen. Just a quick question, do you
think you'll ever retire? No.
OK, Yeah, yeah, it's a funny thing.

(55:08):
We are, we are of a generation. We're of an age, although I'm 10
years older than you. Where like retirement, like oh,
what is that? All right.
So the last question is this. Well, not in my DNA like no,
it's. Not in your DNA.
It's not in our DNA. If I was like, OK, I'm going to
retire and I'm just going to garden.
I mean, within two days in my garden, I would probably think

(55:29):
of how to create a business around my garden.
It would just happen. I'd be like, oh, more people
need tomatoes. I'm going to set up the stand on
the corner of my street. I'm going to start with
tomatoes. I can make tomato sauce out of
this. This is amazing.
For a lot of us, if we know thatwe're never going to retire, the
question that we need to ask ourselves is how will I curate
my light life differently if I know I never will retire?

(55:53):
Meaning, how are you spending time with family, friends,
etcetera? How do you take that time with
your family? You took that year off?
How did I do my midlife atrium? How do I know that for me,
Sunday is my Sabbath and I I do,I try to just go for long hikes
and I'm an extrovert. I was an extrovert through most

(56:14):
of my younger years, although I was an extreme introvert as a
kid and I've I'm converting backto being an introvert and so I
know I need my space on a Sundayso.
I love that I could talk to you on a whole another podcast about
introvert and extrovert. And like, you know, I thought
maybe it was set like you're born an extrovert or you're born
an introvert, but I really thinkit changes throughout your life.

(56:36):
You're an, you could be an ambivert.
Well, I think so. Some of the, Yeah, we're going
to keep going for a moment on this one then, because you're
interested. So the research is fascinating.
I'm a geek. I love social science research.
To look at this. And around age 45 or 50, people
start to go a little more interior.
We spent our life being exterior.
You go a little interior, and that can mean a lot of things.

(56:56):
That can mean you start getting more curious about spirituality,
spirituality and religion. Again, these are all averages
here, But it also for a lot of people means that they go to a
space where they start to enjoy their own company a little bit
more and they start editing the things in their life that they
don't want to do. And as a result, for a lot of

(57:17):
people, three times as many people around age 50 move from
extrovert to introvert as compared to the opposite moving
from introvert to extrovert. So it is, it is part of the life
stage of midlife. It doesn't necessarily mean we
become hermits, but, and it doesmean for me, I listen, I, I
start a workshop today, I'm here, I'm here in Santa Fe, I
have workshops starting later today.

(57:38):
I got to be an extrovert in a workshop, but I also know that
at the end of the workshop and maybe even in the midst of the
workshop, I'm going to take sometime to myself.
So we, you know, learning how tobe.
As we get older, we become alchemists of our polarities,
masculine, feminine, introvert, extrovert, curious, wise,
gravitas, depth, levity, laughter, you know, secular,

(58:03):
religious. The best people I know who are
85 years old and present, there are people who have learned not
to be compartmentalized, but to be integrated.
They integrate and alchemize those polarities.
So. Well, you know my life's my
largest. If I elevate 10,000 feet up,
what care? What do I care the most about?
I care the most about the masculine and feminine energy

(58:26):
becoming more balanced not only within ourselves but on the
planet. And I think most of the things I
care deeply about will resolve themselves or heal when that
balance happens. And I think the feminine energy
on the planet for about 3000 years has been pretty squashed.
And I think we're all suffering as a result.
And I say energy because we're all made-up of masculine and

(58:46):
feminine energy. I don't even see it as gender as
much as I do a true feminine energy.
And when I started Spanx, I knewthat business was a very
masculine construct. I was like, this was created by
men, it was invented by men. The rules were made by men.
What success looks like was defined by man.
And I'm not a man. I'm a woman.
And so I, you know, I didn't have any voice in how all this

(59:08):
got constructed. What would it look like for me?
Like what? And that's part of why I was
really careful about getting investors.
I was like, I'd rather bootstrapit and kind of honor this divine
feminine and this knowing insideof me along with my masculine.
But I didn't want to squash the feminine to get to where I
wanted to be. And so I was very intentional
about trying to create Spanx with a lot more feminine energy,

(59:32):
which at the time, it's getting better, but at the time,
feminine was really seen as a weakness in my opinion.
It felt like it wasn't taken seriously and I saw it as a
superpower. Well, you are have been a role
model for that for sure. So imagine last question that as
the role model, a woman 20 yearsyounger than you approaches you

(59:52):
and says, you know, I bought in the auction a tea with Sarah or
or actually matcha. You like matcha, don't you?
Matcha with Sarah and getting matcha with you next week and
spending some time with you. Will you come to that meeting
with a bumper sticker? Doesn't, not a physical one, but
just in your mind, a wisdom bumper sticker, a piece of

(01:00:15):
wisdom that you have learned along the way in life or in
business or whatever it is. That really is defines what
you've learned and what's the origin story for that learning?
Where did where did you know if there's a, a, a, a Sarah Blakely
wisdom bumper sticker with your fingerprints on it, what might
it be? And of course, there's there's
many, but and what's the origin story?

(01:00:38):
How did you learn that? I mean, you're leaving me with
just a really light last, last question, Chip.
Well, I mean, 22 bumper stickerscame to mind.
The first one is my life motto that I have for a long time,
which is the more you experiencein life, the more you have to
offer others. And So what that did was by

(01:01:00):
framing life experiences to be in service of others, it made me
have more courage to say yes to a lot more things that scared
me. And then the second thing I
would probably say is, you know,what you don't know can be your
greatest asset if you let it. So not knowing how something's

(01:01:22):
supposed to be done can be your advantage if you can get over
the mindset and the negative self talk of telling you like
you're not the expert or why youor you know, if you.
So it comes with that mindset, courage that you have to develop
like a muscle. But what you don't know is your
greatest asset, because it meansyou're not going to do it like

(01:01:42):
everybody else. That's exactly right.
And my dear, you have not been doing it like anybody else.
Thank you so much for coming to the midlife chrysalis and to
tell your story, but also with the frame of midlife.
You know, I, I just, it's a lifestage that doesn't get a lot of
respect or love. And it's, it's really the
longest life stage that we have in our lives.

(01:02:04):
It may, it might last as long as35 to 75.
So thank you for giving us some wisdom.
Well, thank you, you, you, you and your modern Elder Academy
has been very pivotal and helpful to me during this
transition. So I'm thrilled.
I'm happy to know you, everyone.You should go to NEA.
It's really amazing. And thanks for having me on your

(01:02:25):
podcast. Doesn't Sarah Blakely have
infectious joy? I love hanging out with this
woman, whether it's, in this case, across a screen or in
person, in Baja or in Santa Fe, because she's been at both of
our campuses. My 3 lessons from this from this
episode were #1 you know, she reminds me of Liz, Liz Gilbert.

(01:02:48):
And the reason I say that Elizabeth Gilbert, also an MEA
faculty member and friend, wroteEat Pray, Love.
And then like, wow, when your first thing is a success, you
know, how do you do the second thing?
You have to have a growth mindset, be willing to fail, be
a beginner. Again, not easy.
But Liz, Liz did that and Sarah did that with sneaks.

(01:03:11):
The follow up to Spanx on these sneakers that are, you know, I
wouldn't call them controversial, but they haven't.
There's a lot of people who are when you, when you've had a big
success like she has had with Spanx, there's a lot of people
who just sort of want to cut youdown.
And what is so beautiful about Sarah is she's willing to try
and, and make this new business a success even when there's a

(01:03:34):
lot of naysayer. So I just, she's got a
confidence and a courage and a conviction to everything she
does. Secondly, I really love the fact
and she's told me this in person, but I, I love the fact
she actually talked about it on the episode, the fact that it
was her father and it was actually her father.
When he was leaving home, his parents were getting divorced

(01:03:56):
and her father was really in a place where he was.
He knew that she was going to struggle by the fact that the
that her parents were no longer going to live together.
And he gave her these Wayne Dyer, the the, you know, sort of
self help guru Wayne Dyer cassettes in these little
cassette cases in a bowl. She she said that dark times

(01:04:19):
have a hidden blessing. And I think that's really true.
Again, that's a perfect, you know, frame to think about the
midlife chrysalis. Midlife chrysalis is a time
where not everything on the external is happening in the way
you want it to, but on the inside, your painful life
lessons are the raw material foryour future wisdom.
And for her, that time in her life, which was which was a

(01:04:40):
difficult time. It was in her teen years allowed
her to start getting more versedin this idea of how do you shift
your mindset to a positive mindset.
And she certainly had that her whole life since then.
And then finally, I I loved her reference to intuition being
like a car radio. What are you doing to actually

(01:05:01):
better TuneIn that intuition so you can get the downloads?
You know, Sarah's funny because you, you know, she's a very
successful, she's a billionaire,I think the first self-made
billionaire woman, business woman in the US.
And and yet when you hear her talk about her inspiration, her
intuition and how she comes up with really interesting ideas as

(01:05:25):
a conduit and a catalyst, it's often going back to the
intuition. It's going back to believing
that there's messages being sentto her.
Now, some people, you might hearsomeone say that and say like
that person's crazy. Sarah's not crazy.
It's worked for her. So my question to you is, how
are you tuning in your car radiofor your intuition, Whether it's

(01:05:49):
through meditation or journalingor coming to an MEA workshop,
What is it that's going to allowyou to invest in your intuition?
Thanks for joining us this week.We'll see you next week.
Thanks for listening to The Midlife Chrysalis.
This show is produced by MidlifeMedia.
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(01:06:10):
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