July 23, 2025 • 59 mins
What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?
In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.
What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond.
Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son Relationship
Learn more about MEA at https://www.meawisdom.com/
#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
When your values are clear, yourdecisions are easy.
As I evolve as a human, I want deeper relationships.
I want relationships that challenge me intellectually,
challenge my thoughts, get me reading more.
I am definitely someone who's always like seeking more
knowledge, information with us through podcasts.
(00:20):
I'm pretty lucky to get to do like an artistic thing in my
life. 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.
(00:41):
Hello, it's Chip Conley here at the Midlife Chrysalis and I'm
honored to have interviewed hereat our Santa Fe campus.
Scott Eastwood, the well known actor who's acted in 40
different movies, the son of Clint Eastwood and somebody
who's become a friend of mine because he's building a home
just down the beach from the MEAcampus in Baja.
(01:03):
I'm going to do a little bit longer intro for this one
because I really, you know, one of the things that Scott and I
have bonded on is about our relationship with our fathers.
Now, I will say that in the course of this interview, I, I,
there were some limitations on what kinds of conversations I
could have with him about his dad who had recently turned 95
years old. But what I can say is that I
(01:25):
want to tell you a little bit ofmy, about my story of my father
and why Scott and I tend to really have a kinship because we
both had, you know, sort of hardcore fathers.
My father's still living. He will turn 88 at the end of
September. But my upbringing with my father
was, was was at times really challenging for me.
(01:48):
I was the oldest son, the only son of three kids.
Both of my parents are first born.
And so I'm a first born of two, first two first born.
I was Stephen Townsend Conley Junior, a chip off the old
block. So I was meant to be, as my dad
said to me at a young age, you're supposed to be a better
version of me, which was not hard because there were times
(02:10):
when I saw my dad, you know, being a little bit aggressive.
He had a bit of an Irish temper.Sometimes he drank a little too
much. And so the idea of being a
better version of dad felt good,except for I'm not my dad.
And so to actually be in a situation where I could feel at
a relatively young age that I was more of an introvert.
(02:31):
My dad's an extreme extrovert. I became an extrovert over time,
but I was a very extreme introvert as a kid.
My dad was my baseball coach. He was the, he was, I was a *
pitcher because of course, dad wanted to make sure that I was,
you know, achieving beyond anybody else.
My dad was an Eagle Scout and hewas our Boy Scout leader.
(02:53):
I became an Eagle Scout and my dad was always perching above
me. You know, my dad was, you know,
there's some kids, some adults like, who just think about their
parents being absent. My my parents were exactly the
opposite. My parents were all involved in
my life in every way and I felt like at a very narrow path.
I went to the same high school as my father.
(03:15):
I played water polo and swam like my father did.
I was student body president of the high school as my dad was a
in student government himself. I went to Stanford.
Guess where my parents went to school?
Stanford. I got a girlfriend, I got a
girlfriend, I had a girlfriend. And my first year of college for
about a year and a half, Lynn, who I just loved deeply loved
(03:37):
her. My parents loved her.
My parents met at Stanford. So guess what the imprint of
what Chip was supposed to do was, was upon me in the sense
that I was going to get married to Lynn.
But something didn't feel quite right to me.
And there was always this littlelingering flavor of of an
emotion I had frankly for my best friend in in high school
(04:02):
who actually joined me and played water polo with me first
year at at Stanford. And he went on to play in the
Olympics. Long story short is I had this
experience of at age 22, having to come out to my father as a
gay man. My father was a Marine captain
in the reserves at one time. He was a very extreme
(04:25):
conservative Republican. So the idea that his only son,
the son who is named after him, the son who he had, you know,
done, you know, the Pinewood Derby building, building race
cars with the, the son who was supposed to actually be a better
version of him was so different than him, was really traumatic
(04:48):
for my dad. And he actually hid it.
He asked me to hide it from my mom for a couple of years.
So it was just a little secret my dad and I had, and my dad
wanted me to go to therapy and Iwent to therapy and I had a
therapist who wanted to do reparative therapy with me.
And that's a whole other story. I'm not going to get into that
right now. But as I moved into my 20s and
(05:09):
my father started to realize that, you know, I'm, I was not
moldable. I was no longer going to be
dad's version of Chip. I was going to be Chip's version
of chip. But as I said to my dad, when he
said, listen, my biggest fear isyou're going to get AIDS because
I came out in 1983, which was, you know, the, the summer, in
fact, the summer of 83, it was 1Newsweek for the first time put
(05:32):
AIDS on its cover. And he was really worried that I
was going to lose my ambition. That has not happened.
And my dad said to me, I think you're going to become a, you
know, a flower, a flower, a florist or a hairdresser.
And he didn't like that idea. And I said, Dad, I, I'm still
ambitious. And by the way, I joined a
different both of my when I was at Stanford, I joined a
fraternity just like my dad, butI didn't join his fraternity boy
(05:55):
was IA rebel. Long story short is by the time
I was in my mid 20s, it was clear that my my father was
still struggling with this. At this point my mom knew about
it and I think they worried about my future.
You know it. Will I find love in my life?
Will I'll never have kids, they'll never have the Conley
(06:17):
name will not continue on because their only son will not
have, you know, children. As it turns out, everything
changed. 26 at 25 still. But on my 26th birthday I
finished a business plan to start this hotel company, Joie
de Vive. And my first hotel was the
Phoenix, a rock'n'roll hotel that I was going to create in
(06:39):
the 10 year line of San Francisco.
That became a very big success. My dad, actually, to his credit,
even though he thought it was a crazy idea, helped me to raise
some money. He put $50,000 of his own money
in it. My parents are not wealthy, but
he also helped me raise some money from other people.
So my dad was there for me and he saw in my leadership and
(07:00):
being the CEO of this company that ultimately grew to 3500
employees that the son that he wanted, this masculine, macho,
John Wayne like character was not who I was, but that Even so
I was a great leader. And that I had a creativity that
was unleashed when I came out. The creativity to be able to
(07:22):
have a design eye, to be empathetic and to not actually
feel nervous about actually showing some of my maybe more
emotional or feminine side. And my dad is still here.
He, he is still a deep part of my life at and at the end of
this talk. Today, after you hear Scott, I'm
going to do an outro talking about a very pivotal time in my
(07:44):
life, later in my life in midlife when my dad was there
for me. I hope you'll enjoy this
episode. You'll see that Scott is the
legacy holder of his father's legacy.
The fact that Scott has performed in 40 films, mostly
westerns and war movies, sort oflike his father.
(08:06):
Interestingly enough, the one time in my life I was lucky
enough to go to the Academy Awards was 1991, the year that
Unforgiven, Clint Eastwood's film, was won Best Picture.
Having parents who are ever present having to live up to
parents expectations. If any of that relates to you, I
think you'll enjoy this episode with Scott and me.
(08:28):
Scott. Chip.
How are you? I'm good.
So Scott, you're you've you've actually, I said yesterday to
you because we were traveling from Baja up here to Santa Fe
and I thought like 30 plus films.
But it's, I did some research. It's like over 40 films and
(08:49):
you're only 39 years old. And you started when you're
about 20, about 19 or 20 years old.
So that's like 2 films a year. Yeah, that's incredibly
prolific. Well, I don't know about all
that, but that's it. Was busy.
Yeah, busy might be the better. What?
Which of the films are you most proud of?
Which of the ones that you enjoyed the most?
(09:10):
Every experience is like a summer camp.
Some are really fun and light and you meet great people and
some are difficult and not such great people and some are sort
of in between. Some can be like the the hardest
films ironically end up being sometimes maybe the better
(09:34):
product at the end of the day, but the experiences are the most
important for me. And what's it been like working
with your dad? So your father is Glenn
Eastwood? The first and only time I've
ever gone to the Academy Awards was when he won for Best Picture
and Best Director for Unforgivenin 1991. 92. 92, yeah, the film
(09:55):
was in 91. I think that the award is in 92.
He's been in 60 films or more maybe.
What was? What's it been like to work with
him? Like any father, son
relationship and then working with your, your father can be,
can be great and can also be difficult.
He was very old school in the way that he, he still is, you
(10:19):
know, in the way he is disciplined, in the way he makes
films. And I think he always held me to
like the highest standard, right.
So, but yeah, it's, it's when I look at it like from a 30,000
foot level, I feel incredibly blessed to have been able to
even just be exposed to film around him and and learn, just
(10:40):
learn about movie making and be inspired by it.
So getting to go and work with him on, on film sets was, was
always a, a great, a great thingfor me as a, as a younger man.
So I I grew up as Stephen Townsend Conley Junior, a chip
off the old block. My dad wanted me to be a better
version of him. And, you know, my life at times
(11:04):
has been the process of learninghow to both stake out my own
path but also learn from my dad.How's that been for you?
I mean, you're in you're in the film business.
You do a lot of things. You're an investor in a variety
of businesses as well. How has that been staking out
your own path, you know, relative to your dad?
And has that been easy, hard? How are you wiser about that
(11:28):
today at 39 then you were at 29?Yeah, You know, look, I mean it,
it's I'm an optimist. I look at the, I try to look at
the glass half full always. And I'm like the experiences
that I've had gave me a lot of knowledge at an early age that,
you know, people probably going into the film industry or
(11:51):
wanting to be in the film industry didn't have at the same
time people were like, well, you're just Clint Eastwood son,
you know. And that's, I think people love
to just sort of discount people.It's like a, it's a, it's, I
don't know if it's like a human condition or, you know, people
wanting to like put other peopledown.
They call it schaudenfreude or something like that.
In German it's a yeah, it is a thing.
(12:11):
And so, you know, you get that and it's like the good with the
bad, right? So, you know, trying to overcome
that and then go out and be my own man and, you know, be in my
own movies and, and make my own movies, produce my own movies,
act in my own movies and all those learning experiences that
come along with it. But at the end of the day, I, I
(12:32):
sort of like, you know, I'm, I've always been pretty good at
drowning out the noise. I don't know if that's just like
an like an ignorance thing. And I'm just like, ignorance is
blessed. Whatever.
I've always been pretty good at being like, well, that's, you
know, fuck them. You got to just keep going.
Yeah, yeah. And so it's that that for me has
(12:52):
always been like my North Star. So just keep your head down and
work and don't complain. You're so you're so lucky to
just be on a path where you, you, you do what you want and
you do you do what you like. You know, you, you, you get up
every day. And some parts of the business
are great, but a lot of the parts of the business are really
interesting when you get a make a product that people gravitate
(13:18):
to. And I've always thought that's
like, I'm, I'm pretty lucky to get to do like an artistic thing
in my life. And breaking out of the
stereotyping, it's easy as a as an actor to get stereotyped.
It's like, oh, you, you do war movies or you do westerns or you
(13:38):
do whatever. But it feels like some of the
films that you're work you've been working on lately and some
of the films you've done historically romantic comedies
and you're opening up new doors and becoming a beginner in in
some new genres. What are you most excited about
these days in terms of the filmsthat you've been working on?
So I have a bunch of films that haven't been released that all
(14:03):
have been very, very different experiences.
Big action movies, sort of survival, a survival movie.
I just did another, call it romantic comedy type of film.
It was a Colleen Hoover film. Like for me, it's it's always
great to, you know, I don't wantto get bored.
(14:26):
And so when I if I'm like, if I just did something like that,
then I'm like, well, I just kindof did that.
I just did that material. So let's look for something
else. And so it's not like it if
there's no grand design. It's more just what is available
and, and what sort of, you know,what you're reading and what
you're gravitating to. I have a film that that Luke
(14:48):
Wilson and I are are putting together right now and we're
hopefully be shooting in September down in Mexico.
And just so everybody knows, Scott lives down the beach or is
building a home with our same contractor down the beach from
where we live and the MEA campusin Pescadero.
Oh, I'm telling everybody that. Oh, no, you're going to have all
(15:10):
of your, your groupies showing up in Pescadero.
Yeah. Oh, no.
OK. They'll probably be attending
some of your MBA. They'll come to the MBA.
Yeah, so. That was an MBA plug.
Yes, sure. This film is going to be shot in
Mexico. Yeah.
And. And you're excited about it?
Yeah, I'm excited about it. It's a, it's a film that reminds
(15:31):
me of, you know, films of like the late 90s or early 2000s, you
know, movies like Major League or, I don't know, Bull Durham
or, you know, just movies that, you know, were, were.
Baseball movies. Baseball movies.
It's a guy. Movies.
Yeah, maybe. Yeah, maybe not so politically
correct. Yeah.
(15:52):
So let's dive into that for a minute.
So because a lot of the films you've done and a lot of the
films your father's done have had a very strong masculine
element to it. But actually what's been
interesting about some of your films as well as your dad's
films is often it's sort of looking at the hero mythology
and saying, is that true? Right.
(16:14):
I mean, Unforgiven was sort of, you know, with your dad, it was
like that and Flags of Our Fathers, which was a, a film you
did with your dad 20 years ago. It is about like the mythology
of Iwo Jima and the the flag that was being hoisted and the
story behind it. And so there's where's your mind
in terms of the idea of masculinity in the modern
(16:35):
culture, especially with men. You have so much evidence that
younger men are struggling relative to younger women as
they go into adulthood, in university settings, in
earnings, etcetera. Yeah, You know, I, I, well, I
mean, we touched you. You asked a couple different
questions. So I'll start with the first
(16:56):
one. And I think, yeah, my father's
films have always examined, at least in the later years, they
examined, you know, the complexities of the character or
the human behind a, you know, a very, like, machismo man, right.
Like we're a lot of different Shades of Grey in this life.
(17:18):
And a lot of times that machismo, it has another side of
it too, Like as you're dealing with regret and, and you know,
all the things that humans deal with and that's, I mean, you
know, unforgiving sort of was like the the culmination of of
that, right? It's like this mythology behind
all that was a life of like, Hey, this is what I this is what
(17:41):
I fucked up on and dealing with that.
And I always find that to be themost interesting when it comes
to like complex characters because nobody is one thing.
And when you kind of like, now put it through the lens of like,
what is what is it to be a man? I think it's it's very complex.
(18:02):
I think that that's it's like just anything.
It's like there's no one way. It's like both things can be
true. How would you say you are
evolving as a man, say, comparedto your early 20s?
Like what is what? How would you say that you're
wiser as a human but also as a man today?
I mean, like in your 20s, you don't know anything.
(18:23):
You're, you're running, you're running and gunning and you're,
you're, you're being, you're, you've probably been affected by
culture and whatever you've, youknow how you're, you're, how
you're raised and then you're trying to figure that out.
I think if we're also for young men, I think we're dealing with
like a lot of like testosterone,a lot of fight or flight, sort
(18:45):
of, you know, responses to life scenarios.
And as you kind of age and get alittle wiser and you, you
realize there is like, there's different, different ways to
handle these situations. I think it it gives you like a
certain power as well to know that you can you, you don't you,
(19:09):
you, you can handle life situations with, you know, with
complexity. You know, it is interesting.
As we get older, we are less emotionally reactive, although
there are examples out there whodon't fit this profile.
But on average, our emotional intelligence grows.
Sure, as you're you're 39, you're turning 40 later this
(19:29):
year. In March.
Yeah, March. Early next year.
So you're sort of at that dawning of midlife.
How? Do you see midlife?
Like what is what is your perspective on?
We this the this is called the midlife chrysalis, apparently
because we're trying to remake the myth of the midlife crisis.
(19:50):
Yeah, the idea that maybe we're supposed to learn some things
and it's not about a crisis that, you know, your world falls
apart. Sure, maybe it does fall apart
in certain ways, but actually? On the other side of that
breakdown is a breakthrough. So how do you see midlife,
especially in the in as an actor?
I like that you're aging me right to my death at 80, so I
(20:14):
like that you're living. You calculated that my midlife
is 40. No no, no midlife.
Midlife is midlife lasts. Midlife lasts like 4 decades, 4
decades. So it's probably from 35 to 75.
That's my opinion. Sure.
Yeah, sure. Yeah, I think, I mean, you said
it sort of, well there. I mean, one door closes, another
(20:36):
opens. But yeah, sort of trying to.
I mean, I find myself this year specifically for a lot of
reasons, kind of taking a step back in the film industry and
taking a step back and, and liketrying to figure out what is my
(20:56):
next decade or two look like? What, what, what does that look
like? So I find myself like asking
myself those questions sort of on a daily.
And I think if you're not, you could find yourself sleepwalking
through your, you know, 40s and 50s and wake up and be like,
(21:17):
well, I'm not doing what I want to do.
Or, you know, I'm doing what some what someone else told me
I'm supposed to do. So I'm, yeah, I'm trying to, I'm
trying to sort of like take a 30,000 foot level of like where
I've been and and where I want to go.
Yeah. And this is, you know, one of
the classic questions of midlifeis, you know, am I living my own
(21:38):
life or am I living someone else's success script that I,
that I have been reading, to usea, a little bit of acting
metaphor. And, you know, if you were to
dream about something else you could do, like, let's get crazy
for a moment. Let's say you were not in the
film business. Let's say you were doing
(21:58):
something completely different and you went to an MEA workshop.
And at the end of the MEA workshop, you said like, OK, I'm
supposed to be a pastry chef or OK, I'm supposed to be a
firefighter or OK, I'm supposed to be what, what might be
something that you might find fascinating, maybe even from
childhood that you could resurrect.
(22:20):
Like for me, you, you we've beentalking about the, the, the Film
Festival, the MEA Film Festival.And you can, you've seen how
passionate I am about it. And, and I think back to when I
was younger, I wrote a screenplay in my early 20s.
I loved going to movies. I used to do, I used to be a, a
pretend movie critic in when I was 12 years old.
(22:40):
And. And So what might that be for
you? If I got to bring it back to my
12 year old self, I had this andI'm not sure where it came from
because it it my mom was confused about it, but I had
this desire to design houses where I would draw floor plans
(23:02):
as a 12 year old kid who's drawing like floor plans, like
kitchen floor plans and layouts for houses.
I spent a lot of time in Hawaii growing up being in like in real
nature and in warm weather. It still has like a I saw like a
calling for it so. That's that humidity thing.
(23:22):
We were talking about humidity earlier today and, and Maddie,
your partner and I was like, youknow, humidity can sometimes be
a pain and you're like, no, I love humidity, but that's, you
know, Hawaii has some humidity. Hawaii, yeah, You know, tropical
islands anywhere in the South Pacific.
I think if I'm like, if I if I'mlooking at this next thing and
(23:42):
what would be like fill my soul,it's something in the tropics,
something adventure, maybe taking people on tours or doing
something adventure and showing people under the stars at night
on Academy. I mean, I just that this is kind
of what I sort of see. I don't know what that is
(24:03):
exactly, but. Yeah.
Your father's 95 years old. If you were to live till that
age or longer, how would you seeyour life evolving in your 40s
and 50s and 60s and beyond? I mean, he he moved from acting
into directing and producing. You've done some producing.
(24:26):
I don't know that you've done any directing yet.
Is that something you'd like to do?
And what you know, you, you've said both to me personally as
well as in the press, like filmsare a director's medium because
they really control things, which can be hard because
sometimes a film comes out and you're like, Oh my God, there
was so much good stuff that never made it, you know, into
(24:50):
the final cut. Is directing something that you
would see yourself potentially doing as you get older?
Because in some ways director, you could see a director having
wisdom that you build over time.Before I, as my dad would say,
before I hang up my spurs, I, I'll definitely give it a shot
directing. It's, it really is film is a
(25:10):
director's medium. You know, the director is really
making all the, all the decisions.
They're, you know, it's a collaboration, but they're
hiring the departments, right? They're the CEO.
So they're hiring the departments and then directing
those departments accordingly. Set direction, locations, saying
no, I want something more grand.I want something with bigger
(25:31):
vistas. I want feel something that feels
older, you know, make it this, make it that the wardrobe, all
the departments, all those decisions from the pre
production of a film all the wayto its completion and it's post
production. It's all director driven.
And I like that because it's it's it's a it's the whole
(25:53):
process. Every decision is a creative
decision you're making for better or worse.
But I don't think I would want to just sort of stay in in the
current position where I'm just an actor for hire and not I'd,
I'd rather fail on my own terms.You know, I'd rather go out
(26:15):
there and take some swings than just, you know, because you
sometimes you get on a film in your go, OK, I would not be
doing it like this. You've been around enough.
You could go. I've seen it done this way and
I've seen it done this way. And I know that way is not going
to work or not going to look good and then you're on.
But I don't really, I don't really have a lot to say here
that the trains already left thestation.
(26:37):
So you're kind of, you're kind of going, you start to start to
chip away at you a little bit and go, I got to, I got to, I'm
going to give this a shot on my own.
How soon? Soon.
So you got to find the well, theproblem.
The problem is, is you got to find the right material.
And I don't like to write. I like the collaboration of
reading something and giving notes and having an idea and
(26:59):
having other people write it. But this right here is, is
really tough. Like, you know, my hat goes off
to the riders that do it well because it's, it's a, it's a
hard thing to lock yourself in aroom and be isolated and, and
put pen to paper. So I want to explore this idea
of time and as we get older, time becomes more valuable.
(27:22):
Maybe we we talked about regret earlier.
Maybe we might actually think about the things that we wish we
had done. One of the questions we like to
ask at MEA is 10 years from now,what will you regret if you
don't learn it or do it now for you?
Because anticipated regret. The thing I like OK at 49, I
(27:43):
will regret that I didn't do or learn this in my 40s.
What comes up for you when you think that?
Because for me, I'll I'll just as when I moved to Baha where we
both you'll be living soon enough part time.
I had a a mindset at age 56. I was too old to learn to surf
(28:04):
and I was too old to learn Spanish.
But when I put it in this framework of 10 years from now,
what will I regret if I don't learn it or do it now, knowing
that I might still live part time in in Mexico at 66 near a
surf break, a couple surf breaksand also, you know, a place
where everybody's speaking Spanish.
(28:25):
It gave me the catalyst to say Igot to learn Spanish.
I got to learn to surf. Now I'm not very good at it
either, but it actually got me off off my Duff.
So what might you regret if you don't learn it or do it now, or
at least sometime in the next 10years?
I feel like I've, I've accomplished a lot of, you know,
(28:47):
the, the sort of action sports things physically, a lot of
physical things that I've wantedto do and became, you know,
learned how to spearfish and jiujitsu and Muay Thai and surfing.
And even though I am still a beginner at certain things,
which I love being a beginner, like I, I started foiling last
(29:09):
year and, and that became, you know, sort of not a beginner at
that. And then I started trying to do
like a wing foiling, which is sailing and foiling at the same
time. I feel like a lot of like
physical stuff I've done. I think what I want more now is
more intellectual stimulation, so.
That's why you're hanging out with me.
(29:29):
Yeah, Yeah. You know what I mean?
I mean, it really is. I mean, as I evolve as a human,
I want deeper relationships. I want more.
I want relationships to challenge me intellectually,
challenge my thoughts, get me reading more, get me interested.
I'm I'm definitely someone who'salways like seeking more
(29:50):
knowledge, information, whether that's through podcasts or books
on tape. I also think this is going to,
this is broad, but if I don't follow my gut on, on, you know,
in 10 years from now, I think I'm going to be, I think I'm
going to be upset with myself sothat that's, you know, hey, I
got to give this directing thinga shot or hey, I got to do this
or I've got a, you know, you're going to follow my gut.
(30:11):
When you don't follow your gut, that's when you really get upset
with yourself. And that's a lesson you learn
from your dad, isn't? Isn't that one of his key
lessons he's taught you? Follow your gut.
Any time I've said yes to a job and I've kind of known it's not
the right thing, it's not the right deal, I've done it for
money or I've done it for other reasons or as my agents or
(30:32):
whatever saying, oh, you got to do it, you got to do this, it's
great. You know, it's good for your
career. Whatever is that other voice
that if you listen to that othervoice and you don't listen to
your gut, it usually, it usuallysteers you wrong and then you're
upset. The only person you can be upset
with is yourself. So I think just listening to my
(30:53):
gut, yeah, that's the biggest thing.
So longevity's become a a hot topic everybody.
'S a lot of experts out there. A lot of experts out there, a
lot of people trying different things.
And one of the things I've neverdone is something you did when
you had a a broken ankle and youwere filming The Outpost, a film
(31:18):
that was very highly regarded about Afghanistan, the war in
Afghanistan in a particular battle that happened there.
So you ended up in a hyperbaric chamber to actually speed the
healing, the healing of this ankle.
But tell us a little bit about that movie because it's actually
one of I think, you know, one ofmy favorite movies of yours and
(31:40):
one of the highest rated movies of yours.
What what happened? How'd you break your ankle, if
you want to talk about that? And what was that movie like?
And and how, how do you think about your own longevity?
So, yeah, I, I actually, this was, I think it was in 2018 or
19, I was set to start filming the Outpost in, in Bulgaria,
(32:05):
which we were dubbing for Afghanistan.
And I, I, it was about six weeksout from shooting and I broke my
ankle and I called the director and the producer give them this
news. But I told them the doctor says
it was a little bit of a white lie.
(32:26):
The doctor says that I'll be ready in three to four weeks.
Fine, it's good, good to go. Which I knew really wasn't the
case because anyone who knows whoever broke in a bone, it's
like 6 weeks off of it and then you have to sort of do the
rehab. But I was very determined to do
it and they they sort of stuck with me, which I was surprised.
(32:49):
I said, well, that someone else will to go didn't make that
movie. So I did everything you could
possibly do. I was in the hyperbaric chamber
every day or every other day. I started doing physical therapy
before the doctors told me to doit.
I'm under the like belief that you want to keep it.
You know, you got to keep it isolated, but for for a while,
(33:10):
but then you need to keep it. You need to start moving it.
And I ultimately started that movie in a cast because I got
there and I wasn't really ready to be running.
Yeah. Because it's a very physical.
Movie, It's a very physical movie.
Yeah. So I started in a cast and you
know, this, this wasn't really Rods.
(33:30):
Rod Laurie, who was our director, wasn't his dream
because I know he had some some wonders that were that that he
had designed for the film. What's a wonder?
A wonder is when you when you shoot a a scene in one shot, so
the camera might move around andand go back and forth to
different actors, but you're notsort of like adolescents.
(33:52):
Sort of like adolescents, which I which I you believe I.
Think, I think, I think it's bullshit.
I think they did like 4 wonders and they stitched him together.
But that's that's where I'll die.
I guess I'll die on that hill. But yeah, so they had to sort of
design some shots for the first week or two around me.
And then I was, but I was doing so much physical therapy and I
(34:15):
was so determined to like get going that by, you know, we
three, I was pretty much running.
But yeah, it was a, it was a tough, it was a, it was a tough
moment. It was, it was a, it was a
moment that really like, you know, you put your, you know,
your mortality a little bit because, you know, I hadn't
really broken a bone since I was, you know, 1520 years prior
(34:37):
to that. When you're anyone who knows
who, who's ever been injured, it's it's man, it's a mental
like it's some is it takes you, especially someone like me
who's, who's so physical and like part of my daily routine or
part of just my life is like allthese physical hobbies.
So when you're, when you're, youknow, mandated to not be able to
(34:58):
move, I mean, it's, it's rough. It's mentally, I think that, you
know, it always gets you thinking about, OK, like, life's
pretty fragile. Yeah, yeah.
Do you have a favorite longevityhack?
I mean. I mean, I mean.
From a Wellness perspective. Yeah, what do you?
What do you really you? Know, and I'm not an expert by
the way, 'cause I actually I sort of despise all these health
(35:22):
experts because most of them areschlepping something and that
really bums me out 'cause you know, I want people to learn
about health and Wellness without having to be sold
something. And I think there's so much you
can do without taking anything, just the basics, the the
fundamentals, right? Working out, stretching, sleep,
(35:44):
mental, spiritual. Health.
Nutrition. Nutrition, there's so much that
social, yes, community, there's so much in just the the
foundation that you don't need to buy a product and you don't
need a guru to tell you about. But the foundation for me, you
asked the question is the foundation for me is some sort
(36:06):
of yoga daily, whether that's 1520 minutes in the morning or
prior to a workout. Stay hydrated, eat Whole Foods
and try to get to bed early. Try to stay off any devices.
Try to get your circadian rhythmin a good clock where when the
sun sort of goes down, you're sort of going down.
(36:27):
Yeah. So that's sleep and then some
sort of spiritual component if you can and like a communal
component because I think communities and you sort of look
at the what they they talk aboutthe blue.
Zones right, Right. These are sort of the
fundamentals they all had. They all take into those
(36:48):
categories. Or eaten Whole Foods.
They're do it, they're active, they have a communal, they have
a spiritual aspect. And that I just try to sort of
like look at, you know, holistically.
You are wiser today than you were 5 or 10 years ago.
Sometimes what we consider common sense is through the
school of Hard Knocks. Since this podcast is called the
(37:09):
Midlife Chrysalis, I'm early so.Don't count me out.
Yeah, let's say. Anytime in adulthood, from age
18 on, what's a challenge you went through that may have
kicked your butt for a while andyou learn something from it?
You got wiser. If our painful life lessons are
(37:29):
the raw material for our future wisdom, what's an experience you
had that kicked your ass? But you're happy it happened at
the end of the day, because if you're not happy, but you're,
you're happy with the way you metabolized it, sure, and and
learned from it. I think in my early 20s, I was,
(37:50):
you know, I was so focused on, on trying to create a business,
be successful, which I, you know, I, there were things I
started and, and failed at. I tried to launch a whiskey
company. I tried to do a couple variety
of different businesses as I was, you know, working as a
bartender and I was and a valet car Parker and as a young man
(38:15):
you, you know, I, I felt so trying to, you know, trying to
do something but not understanding.
And if it didn't work and tryingto control it and you can't, you
can't control life like you can't.
There's some of some of you haveto let go.
You can work hard. You can put your head down.
It may work out, it may not. Usually hard work sort of
(38:38):
Trump's everything. You will get successful if you
work hard at anything. It's a it's a strange dichotomy.
Sometimes you just have to push harder and sometimes you have to
let go. And that's why the Serenity
Prayer is so powerful. You know, grant me the serenity
to accept the things I cannot change.
To change the things I can. That change the things I can and
(39:01):
the wisdom to know the difference.
So it's really it's the serenityprayer, but it's also the wisdom
prayer. It's really about, like,
understanding wisdom is really about understanding what are the
things you can control. Yeah.
Or influence, and what are the things you have to let go.
Yeah. And you know, that is, to me,
like the ultimate learning when to surrender.
(39:22):
Yeah, is. It's hard.
It's hard. And it's still hard.
It's still a thing. You got to go.
Yeah. Wait, wait, bro.
Yeah, you don't know, but you know, like am I supposed to let
this go? Am I supposed to just push
harder? You know, this is where friends
are helpful, family members are helpful to like be the objective
1 giving you some some indication.
So how would you like people to use?
(39:44):
What words would you like peopleto use to describe you?
Like what adjectives today in terms of who you are on a good
day? I guess one of the mantras I try
to live by, I don't know if I want it's hard like having
wanting my friends to describe me in a certain way because I
guess that feels slightly narcissistic or no.
(40:05):
This isn't meant to be narcissistic because they will.
First of all, let's just say they will be describing you in a
certain way. And one day.
They always do. I mean, people talk about it,
you know, you know, companies have a, a, a brand and we have a
reputation. So the and and, you know,
especially if you're a high profile person out in the
public, people will say, oh, he is and they'll describe you as
(40:29):
one, 2-3 different adjectives. I guess reminds me of, I think
it was a poem that I I, my mom read me as AI was a young man
and sort of it's sort of like life isn't about the material
things. It's not about what clothes you
(40:51):
have or who your friends are or aren't, but it's about how you
affect people on this planet, onyour in your time here and
either a positive or a negative way.
And that really could never occurred alone.
And that has stuck with me. So I hope that I have affected
(41:14):
more people positively and they,you know, given them, inspired
them or, you know, been kind to them or been graceful in my time
here before we're dust and bones.
And that's kind of I guess if like I was said to still it
down, that's what. And and if you have one lesson
you've learned from your mom andone from your dad, what might
(41:37):
those be? That was definitely from my mom
because she was OK. She was, and she is still.
She's still living. Yeah, she.
Is yeah, she was real soulful inthat way.
And I love that because it's just it's so easy to get caught
up in, you know, and what you think is important and none of
that stuff. I remember when my buddy died,
(41:59):
he he passed away and we went, he was very successful guy.
And we went to like box up his stuff at his house and help out
and, and do the stuff and like sort of clean up and like, you
have to do all these things. And you realize like none of
this shit matters. Like the jeans and the things
and stuff. It's like, yeah, you know, you
(42:20):
need, you need a certain amount of that.
It's nice to have a sweater on acold day.
It's like none of the, none of this stuff that I, you know, at
one point in time I was like, oh, that's so cool to, you know,
have or whatever. And then you realize it doesn't
matter, you know, because you'renot guaranteed tomorrow.
And so, yeah, I just, I don't know.
That was that those were lessons.
I don't know necessarily if it was my mom or my dad or our
(42:42):
combination of both. My dad was, you know, I, I
always, always got to give it tomy dad for, for giving me like
hard work and discipline, work ethic and at times very tough
lessons because he was, he was so old school.
Like you're on your own, figure it out, you know, like you're,
you got to go make it as a man in this world.
(43:02):
Like I'm not here to help you. You got to go.
You got bills to pay, you got stuff, you know, and that I
think that's an is like is an important part of being a young
man and trying to like figure itout and, you know, scratch and
claw and learn the value for a dollar.
Have you had any mentors in the the film industry that you can
(43:25):
look to and just say like, yeah,I, you know what I admire, even
if you don't know the person? Sure, I admire them because fill
in the. Yeah, yeah.
I mean, I mean, I've had different mentors through the
years, you know, older friends, you know, sort of like 10 to 20
year my seniors through my life that have always been a good,
like, you know, a good person too give a call to and say, Hey,
(43:48):
I'm going through this or I'm trying to make this decision.
And I think that's really important, right?
Like having a mentor and eventually being or sorry,
having a mentor and eventually becoming a mentor because you
want to pay that forward, right?And so I've done some of that.
I've, I've taken a lot of meetings with young, younger
people who want to be actors or whatever, want to, you know,
(44:09):
advice about the film industry. And I'm always like, my doors
always open for that. OK, so let's say, let's say
someone 1015 years younger than you comes to you, Scott, and
says, Scott, can we have coffee next week?
I know how much you like coffee,Scott.
So what if we have coffee next week?
And I want you to come to the meeting with one Wisdom bumper
(44:32):
sticker, something you've learned, Scott, at 39, that has
had a profound impact on you. What's the bumper sticker, the
wisdom bumper sticker that has your fingerprints all over it?
And what's the origin story thatled to that wisdom?
Because again, our painful life lessons are often the raw
(44:53):
material for our future wisdom. So what might be?
And it's a hard question, no? No, I, I, I actually, I know the
bumper sticker because I think about it often when I'm making
decisions. When your values are clear, your
decisions are easy. And I think that wraps up if you
(45:14):
know, you kind of go back to that when you're, you know,
because decisions are tough. Decisions are some of the
toughest things you're going to do in life because you wrestle
over them. Once you sort of made a
decision, then you, you start onthat path.
But I think, yeah, the the clearer you can, you can really
know what your values are, then the the clearer easier it is to
(45:34):
go, Nope, that's not in my valueset.
And I'm not going to sacrifice my principles because of money
or because of a thing that someone else is telling me to
do. And did you learn a lesson from
the past based upon that? Oh man, probably, probably 1000.
But I actually randomly I heard it from an agent.
(45:58):
I heard it from an agent. And I always thought it was, it
was quite profound coming from an agent where sometimes they're
not as profound to be. But yeah, I thought it was
really, I thought it was really profound.
And, and it's just the, the older I get, the, the, the
easier it is to just put that inperspective and, and that that
(46:19):
be the North Star. Off the top of your head, what
might be some of those values today?
Integrity, honesty. You know, when you say you're
going to be somewhere or do something, you got to follow
through with that. When you make an agreement with
someone, it doesn't need to be done by a lawyer.
It needs to be look, so it lookssomeone in the eye and shake
(46:42):
their hands and you say you're going to do something.
I mean, that's how it used to be.
You know, there's a great book called The Code of the West.
And if anyone, there's someone, everyone should buy this book
because it's just, it's the simple principles that make us
inherently good to each other asa community.
You know, you know, a lot of these principles you, you, you
(47:04):
find in, you know, religious texts, but a lot of them are
just, you know, very regardless of what religion you are or not,
they are principles that are just guiding principles.
And yeah, that, that's somethingmy dad was very, you know, he's
very vocal about like you, you know, you know, you, you say
(47:25):
you're going to do something, you know, you do it.
You follow through with your commitments.
You, if you set out to do something, you know, whether it
be the plumber or a Carpenter orwhatever, you go out and be the
best version of that. You don't mail it in.
You, you do the, you do it once,do it right, You know, do it
with some pride. Have some pride of your owner
ownership, whatever you're creating, those are sort of
(47:48):
them. And there's some more, I'm sure.
No, I, I, I feel your passion onthis so.
Also, it's it's a thing for me. It's like I think that is one of
my passions. I see in like pop culture where
I don't see that. I don't see a voices saying be
someone of integrity. You don't, you know, like we, we
live in this like litigious society and a society where it
(48:11):
becomes about culture and money and Instagrams.
Yeah, yeah, you got to have thisto be successful and happy.
And it's like, I don't see people pushing that narrative.
Like, yeah, like, you know what?Do something of value that that
makes you feel happy and, and bean integrity person with
integrity. Because I think that I don't
(48:33):
know. But in my opinion that that
narrative and that those values,we'll, we'll find you in a place
where you're a lot more. And you'll be passing those
values on to your kids, your mentees, your, you know, the
people who follow you. So thank you very much, Scott.
It is an honor for us to have this conversation.
(48:55):
Yeah. And that's how I.
Want to be here? See the ranch.
Yeah, yeah. Scott got to stay at both of my
both of my houses, the house in Baja before we came up here and
then the house here. And I really appreciate that our
friend, our friendship is just continuing to grow well.
Thank you. Yeah, I wanted to actually give
some context at the end of this episode to my relationship with
(49:21):
my dad again, because when I talk with Scott and there are a
couple things that came up with Scott after we finished the the
episode cut cutting, then recording it that I wish I could
have included. Number one is that, you know,
how much Scott loves his father,how dedicated he is to his dad
(49:42):
at this age in his life. And just to see his dad as a
role model for aging in his mid 90s.
But his dad's pretty much like, OK, there's one way to do
things. His dad's an extreme introvert.
So at times, Scott has had to find his own path, like I had, I
did in terms of like Scott's, you know, a bit of an extrovert.
And additionally, one of the things that came up in my
(50:05):
conversation after the recordingwas that Scott had a near death
experience, not quite like mine.Yeah, just I'll tell you about
about it for a second. And then.
And then I have a story for you that includes my dad.
When Scott was in a a war movie,I can't remember which one it
was, but he was in a helicopter on a hill and the helicopter was
(50:27):
coming down and landing on a hill.
It was a tough landing. By the way, both Clint and Scott
know how to fly helicopters. And when it came down and, and
then Scott was supposed to get out of the helicopter, the
helicopter lurched such that while the while the the
(50:48):
helicopter whirls were happeningit they almost cut his head off.
It was within, you know, just a couple feet of actually missing
his head. And this is as the helicopter
sort of lurched down the hill. So he didn't, he didn't go
unconscious, but he could not, he could not be filming anything
(51:09):
anymore that day because he was so shaken by it.
So I want to just tell you a story that I haven't told on
this podcast yet. And people have said to me,
Chip, we love the podcast. We love what you're doing.
We want more of your stories. So I'm going to just give you
one of my personal stories that's a near death experience
that includes my dad. I'll just say that I've spent my
(51:31):
life running. I have, you know, in 6th grade
in as an elementary school student, there was one point
where lunch was over and I was doing laps around running around
the the playground and I couldn't stop.
I literally couldn't stop. And it was just a mental thing.
And so finally Missus Epperson, my 6th grade teacher, came out,
(51:54):
pulled me by the ear and said you're supposed to be in the
classroom. But I've had a thing about
outrunning fears and and maybe not feeling good enough.
Being an admiration and achievement addict, partly
because of my fear of disappointing my dad, I became a
success, a big success in the the hotel industry.
(52:15):
But in my late 40s, everything started to fall apart.
And this was my midlife chrysalis.
I've talked a little bit about this on the podcast before, and
I was trying to outrun my emotions again.
I had a life that was a bit overstuffed in plot and I just
needed to figure out how to unstuff my my full life, which
(52:36):
didn't feel like a very happy life.
I had a friend named Chip, not me.
This is not me talking about myself.
His name is Chip Hankins. He was my insurance broker, he
was one of my closest friends. He's somebody I I really look to
for spiritual advice and guidance.
By his mid 40s my friendship hadmarried 5 different people as
(52:59):
the officiant in the wedding andso he's loved.
A very well loved guy. He was married, had two kids,
lived part time in New Zealand where his wife was from, and
part time in the San Francisco Bay Area.
So on April 30th, 2008, I was inSaint Louis about to give a
speech to 1000 people and 5 minutes before I was going on
(53:20):
stage, I got a call from Chip's boss, the president of the
insurance brokerage, telling me that Chip had taken his own
life, which is so hard to hear. Hard to hear, you know?
I ultimately had. I lost 5 male friends to
suicide, ages 42 to 52 between 2008 and 2010.
So Long story short is I took note, I had to go up on stage,
(53:43):
give my speech and then afterwards I really, I just
like, wow, I, this was such a surprise.
Chip was, I would never would have guessed that Chip was in
that kind of trauma and he, he had a lot going on in his life.
A month later, this happened in New Zealand.
A month later, we had the memorial service for Chip and to
have everybody get up, go up on stage and give their Chip
stories. While I was going through a
really hard time during that time, I'd had some suicide
(54:05):
ideation myself. You know, I wanted to escape.
I had a a long term relationshipthat was that was probably
ending not by my choice. I had a foster son who was an
adult who was going to prison wrongfully.
I didn't want to be CEO of the company I'd started, you know,
more than 20 years earlier. And we were running out of cash
(54:25):
during the Great Recession. So here everybody was coming up
and giving their chip stories atthe memorial.
And I was like, oh God, you know, it's like being at your
own funeral. And then a month later I broke
my ankle playing baseball at Gavin Newsom's bachelor party
for his 2nd wedding. I got a cut on my leg, didn't
realize I had fertilizer from the baseball field on my leg.
(54:48):
And I ended up going septic on my leg for the course over the
course of the next two or three weeks, Finally got to a strong
antibiotic that seemed like it was working.
And then of course, I should have stayed home.
But being the runner, I got to go do this.
I got to go do that. I ended up on the road giving a
speech in Saint Louis no less, where I'd heard about Chip just
(55:09):
a few months earlier. I'm in Saint Louis now giving a
speech and while giving a speechon crutches on an antibiotic,
when I sat down to to sign booksI went unconscious.
They put me on the ground and the paramedic showed up a few a
few minutes later and I went flatline.
I died. So I had a near death
(55:29):
experience. I literally went to the other
side 9 times over 90 minutes. People ask all the time, what
did you see on the other side? I was like, I saw birds.
Birds were talking to me and it's a longer story, but I'll
keep it brief right now and justsay I could.
I'm like, I'm sitting here rightnow in the recording studio
listening to birds outside. When I hear birds when in, in
(55:51):
the, when I was in this flat line experience, I could
understand what they were sayingto each other and to me and they
were telling me to slow down andsee the beauty and awe.
So ultimately I lived, of course.
And on the other side of that, it allowed me to change
everything. Relationship ended, got my my
foster son, adult foster son Damien, out of prison and sold
(56:13):
the company. But it was my father who showed
up in the hospital when they hadno idea what was wrong with me.
They didn't realize it was an allergic reaction to, to my
antibiotic, but they thought, you know, it might be something
more serious. He showed up and he was there
for me and I loved him and he loved me.
(56:33):
And he just told me how many. He told me so many times how
much he loved me. My father, at age 47, I was at
47. He was at that point in 69.
He was just telling me how much he loved me because he didn't
know if I was going to continue to live.
I tried to convince my dad, OK, yeah, I'm here in Saint Louis.
I'm supposed to go to Toronto for a for a speech in Toronto
(56:55):
and then I'm supposed to go to Houston.
And my dad said, well, you're not going to Toronto because
you're going to be in the the hospital.
So we have to cancel that. But I hear how much you want to
be in Houston. You want to speak to these 100
entrepreneurs about what it means to be an entrepreneur
because this is actually what you want to do next.
He realized he heard me talking previous to me, my flat line
(57:16):
experience, about the fact that I didn't really want to be
running my company anymore. And then I have this flat line
experience and he is there to see, as he said to me on the
flight back from Houston, after I addressed these entrepreneurs
and did a little workshop for them for four hours, he was in
the back of the room watching meto make sure I didn't die on
stage. He said, Chip, I came here
(57:38):
wanting to make sure you didn't die.
I have seen now how you want to live.
We need to figure out how to getyou out of this straitjacket of
this company that you started, this Frankenstein that at this
point you have outgrown so that you can do the thing you're
supposed to do, which is to write books, be a speaker and
(58:01):
explore, you know, what's next for yourself after age 50.
So for the next two years, my father, who I had that very
difficult relationship with whenI was younger and in my early
20s when he sort of disavowed mefor who I was.
My father was there for me in mytime of need.
And quite frankly, in many ways,my father was the one who helped
(58:24):
me to have the courage to actually let go of this identity
of the CEO and founder of the second largest boutique hotel
company in the US, an achievement that in many ways
defined who I thought I was. And of course, I went into my
50s and had the time of my life and loved my 50s, had time to
(58:45):
figure out what was next and then Airbnb and then MEA.
So I just want to finish by saying I wish this was playing
on Father's Day because I just want to say thanks to dad.
Just as Scott has had a challenging relationship but a
loving relationship with his dad, I've had the same.
But over time I have found that he's become one of my best
(59:07):
friends. Hope you enjoyed this episode
and look forward to seeing you next week.
Thanks for listening to The Midlife Chrysalis.
This show is produced by MidlifeMedia.
If you enjoyed this episode, help us spread the word by
subscribing and leaving a reviewon your favorite platform.
When your values are clear, yourdecisions are easy.
As I evolve as a human, I want deeper relationships.
I want relationships that challenge me intellectually,
challenge my thoughts, get me reading more.
I am definitely someone who's always like seeking more
knowledge, information with us through podcasts.
(00:20):
I'm pretty lucky to get to do like an artistic thing in my
life. 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.
(00:41):
Hello, it's Chip Conley here at the Midlife Chrysalis and I'm
honored to have interviewed hereat our Santa Fe campus.
Scott Eastwood, the well known actor who's acted in 40
different movies, the son of Clint Eastwood and somebody
who's become a friend of mine because he's building a home
just down the beach from the MEAcampus in Baja.
(01:03):
I'm going to do a little bit longer intro for this one
because I really, you know, one of the things that Scott and I
have bonded on is about our relationship with our fathers.
Now, I will say that in the course of this interview, I, I,
there were some limitations on what kinds of conversations I
could have with him about his dad who had recently turned 95
years old. But what I can say is that I
(01:25):
want to tell you a little bit ofmy, about my story of my father
and why Scott and I tend to really have a kinship because we
both had, you know, sort of hardcore fathers.
My father's still living. He will turn 88 at the end of
September. But my upbringing with my father
was, was was at times really challenging for me.
(01:48):
I was the oldest son, the only son of three kids.
Both of my parents are first born.
And so I'm a first born of two, first two first born.
I was Stephen Townsend Conley Junior, a chip off the old
block. So I was meant to be, as my dad
said to me at a young age, you're supposed to be a better
version of me, which was not hard because there were times
(02:10):
when I saw my dad, you know, being a little bit aggressive.
He had a bit of an Irish temper.Sometimes he drank a little too
much. And so the idea of being a
better version of dad felt good,except for I'm not my dad.
And so to actually be in a situation where I could feel at
a relatively young age that I was more of an introvert.
(02:31):
My dad's an extreme extrovert. I became an extrovert over time,
but I was a very extreme introvert as a kid.
My dad was my baseball coach. He was the, he was, I was a *
pitcher because of course, dad wanted to make sure that I was,
you know, achieving beyond anybody else.
My dad was an Eagle Scout and hewas our Boy Scout leader.
(02:53):
I became an Eagle Scout and my dad was always perching above
me. You know, my dad was, you know,
there's some kids, some adults like, who just think about their
parents being absent. My my parents were exactly the
opposite. My parents were all involved in
my life in every way and I felt like at a very narrow path.
I went to the same high school as my father.
(03:15):
I played water polo and swam like my father did.
I was student body president of the high school as my dad was a
in student government himself. I went to Stanford.
Guess where my parents went to school?
Stanford. I got a girlfriend, I got a
girlfriend, I had a girlfriend. And my first year of college for
about a year and a half, Lynn, who I just loved deeply loved
(03:37):
her. My parents loved her.
My parents met at Stanford. So guess what the imprint of
what Chip was supposed to do was, was upon me in the sense
that I was going to get married to Lynn.
But something didn't feel quite right to me.
And there was always this littlelingering flavor of of an
emotion I had frankly for my best friend in in high school
(04:02):
who actually joined me and played water polo with me first
year at at Stanford. And he went on to play in the
Olympics. Long story short is I had this
experience of at age 22, having to come out to my father as a
gay man. My father was a Marine captain
in the reserves at one time. He was a very extreme
(04:25):
conservative Republican. So the idea that his only son,
the son who is named after him, the son who he had, you know,
done, you know, the Pinewood Derby building, building race
cars with the, the son who was supposed to actually be a better
version of him was so different than him, was really traumatic
(04:48):
for my dad. And he actually hid it.
He asked me to hide it from my mom for a couple of years.
So it was just a little secret my dad and I had, and my dad
wanted me to go to therapy and Iwent to therapy and I had a
therapist who wanted to do reparative therapy with me.
And that's a whole other story. I'm not going to get into that
right now. But as I moved into my 20s and
(05:09):
my father started to realize that, you know, I'm, I was not
moldable. I was no longer going to be
dad's version of Chip. I was going to be Chip's version
of chip. But as I said to my dad, when he
said, listen, my biggest fear isyou're going to get AIDS because
I came out in 1983, which was, you know, the, the summer, in
fact, the summer of 83, it was 1Newsweek for the first time put
(05:32):
AIDS on its cover. And he was really worried that I
was going to lose my ambition. That has not happened.
And my dad said to me, I think you're going to become a, you
know, a flower, a flower, a florist or a hairdresser.
And he didn't like that idea. And I said, Dad, I, I'm still
ambitious. And by the way, I joined a
different both of my when I was at Stanford, I joined a
fraternity just like my dad, butI didn't join his fraternity boy
(05:55):
was IA rebel. Long story short is by the time
I was in my mid 20s, it was clear that my my father was
still struggling with this. At this point my mom knew about
it and I think they worried about my future.
You know it. Will I find love in my life?
Will I'll never have kids, they'll never have the Conley
(06:17):
name will not continue on because their only son will not
have, you know, children. As it turns out, everything
changed. 26 at 25 still. But on my 26th birthday I
finished a business plan to start this hotel company, Joie
de Vive. And my first hotel was the
Phoenix, a rock'n'roll hotel that I was going to create in
(06:39):
the 10 year line of San Francisco.
That became a very big success. My dad, actually, to his credit,
even though he thought it was a crazy idea, helped me to raise
some money. He put $50,000 of his own money
in it. My parents are not wealthy, but
he also helped me raise some money from other people.
So my dad was there for me and he saw in my leadership and
(07:00):
being the CEO of this company that ultimately grew to 3500
employees that the son that he wanted, this masculine, macho,
John Wayne like character was not who I was, but that Even so
I was a great leader. And that I had a creativity that
was unleashed when I came out. The creativity to be able to
(07:22):
have a design eye, to be empathetic and to not actually
feel nervous about actually showing some of my maybe more
emotional or feminine side. And my dad is still here.
He, he is still a deep part of my life at and at the end of
this talk. Today, after you hear Scott, I'm
going to do an outro talking about a very pivotal time in my
(07:44):
life, later in my life in midlife when my dad was there
for me. I hope you'll enjoy this
episode. You'll see that Scott is the
legacy holder of his father's legacy.
The fact that Scott has performed in 40 films, mostly
westerns and war movies, sort oflike his father.
(08:06):
Interestingly enough, the one time in my life I was lucky
enough to go to the Academy Awards was 1991, the year that
Unforgiven, Clint Eastwood's film, was won Best Picture.
Having parents who are ever present having to live up to
parents expectations. If any of that relates to you, I
think you'll enjoy this episode with Scott and me.
(08:28):
Scott. Chip.
How are you? I'm good.
So Scott, you're you've you've actually, I said yesterday to
you because we were traveling from Baja up here to Santa Fe
and I thought like 30 plus films.
But it's, I did some research. It's like over 40 films and
(08:49):
you're only 39 years old. And you started when you're
about 20, about 19 or 20 years old.
So that's like 2 films a year. Yeah, that's incredibly
prolific. Well, I don't know about all
that, but that's it. Was busy.
Yeah, busy might be the better. What?
Which of the films are you most proud of?
Which of the ones that you enjoyed the most?
(09:10):
Every experience is like a summer camp.
Some are really fun and light and you meet great people and
some are difficult and not such great people and some are sort
of in between. Some can be like the the hardest
films ironically end up being sometimes maybe the better
(09:34):
product at the end of the day, but the experiences are the most
important for me. And what's it been like working
with your dad? So your father is Glenn
Eastwood? The first and only time I've
ever gone to the Academy Awards was when he won for Best Picture
and Best Director for Unforgivenin 1991. 92. 92, yeah, the film
(09:55):
was in 91. I think that the award is in 92.
He's been in 60 films or more maybe.
What was? What's it been like to work with
him? Like any father, son
relationship and then working with your, your father can be,
can be great and can also be difficult.
He was very old school in the way that he, he still is, you
(10:19):
know, in the way he is disciplined, in the way he makes
films. And I think he always held me to
like the highest standard, right.
So, but yeah, it's, it's when I look at it like from a 30,000
foot level, I feel incredibly blessed to have been able to
even just be exposed to film around him and and learn, just
(10:40):
learn about movie making and be inspired by it.
So getting to go and work with him on, on film sets was, was
always a, a great, a great thingfor me as a, as a younger man.
So I I grew up as Stephen Townsend Conley Junior, a chip
off the old block. My dad wanted me to be a better
version of him. And, you know, my life at times
(11:04):
has been the process of learninghow to both stake out my own
path but also learn from my dad.How's that been for you?
I mean, you're in you're in the film business.
You do a lot of things. You're an investor in a variety
of businesses as well. How has that been staking out
your own path, you know, relative to your dad?
And has that been easy, hard? How are you wiser about that
(11:28):
today at 39 then you were at 29?Yeah, You know, look, I mean it,
it's I'm an optimist. I look at the, I try to look at
the glass half full always. And I'm like the experiences
that I've had gave me a lot of knowledge at an early age that,
you know, people probably going into the film industry or
(11:51):
wanting to be in the film industry didn't have at the same
time people were like, well, you're just Clint Eastwood son,
you know. And that's, I think people love
to just sort of discount people.It's like a, it's a, it's, I
don't know if it's like a human condition or, you know, people
wanting to like put other peopledown.
They call it schaudenfreude or something like that.
In German it's a yeah, it is a thing.
(12:11):
And so, you know, you get that and it's like the good with the
bad, right? So, you know, trying to overcome
that and then go out and be my own man and, you know, be in my
own movies and, and make my own movies, produce my own movies,
act in my own movies and all those learning experiences that
come along with it. But at the end of the day, I, I
(12:32):
sort of like, you know, I'm, I've always been pretty good at
drowning out the noise. I don't know if that's just like
an like an ignorance thing. And I'm just like, ignorance is
blessed. Whatever.
I've always been pretty good at being like, well, that's, you
know, fuck them. You got to just keep going.
Yeah, yeah. And so it's that that for me has
(12:52):
always been like my North Star. So just keep your head down and
work and don't complain. You're so you're so lucky to
just be on a path where you, you, you do what you want and
you do you do what you like. You know, you, you, you get up
every day. And some parts of the business
are great, but a lot of the parts of the business are really
interesting when you get a make a product that people gravitate
(13:18):
to. And I've always thought that's
like, I'm, I'm pretty lucky to get to do like an artistic thing
in my life. And breaking out of the
stereotyping, it's easy as a as an actor to get stereotyped.
It's like, oh, you, you do war movies or you do westerns or you
(13:38):
do whatever. But it feels like some of the
films that you're work you've been working on lately and some
of the films you've done historically romantic comedies
and you're opening up new doors and becoming a beginner in in
some new genres. What are you most excited about
these days in terms of the filmsthat you've been working on?
So I have a bunch of films that haven't been released that all
(14:03):
have been very, very different experiences.
Big action movies, sort of survival, a survival movie.
I just did another, call it romantic comedy type of film.
It was a Colleen Hoover film. Like for me, it's it's always
great to, you know, I don't wantto get bored.
(14:26):
And so when I if I'm like, if I just did something like that,
then I'm like, well, I just kindof did that.
I just did that material. So let's look for something
else. And so it's not like it if
there's no grand design. It's more just what is available
and, and what sort of, you know,what you're reading and what
you're gravitating to. I have a film that that Luke
(14:48):
Wilson and I are are putting together right now and we're
hopefully be shooting in September down in Mexico.
And just so everybody knows, Scott lives down the beach or is
building a home with our same contractor down the beach from
where we live and the MEA campusin Pescadero.
Oh, I'm telling everybody that. Oh, no, you're going to have all
(15:10):
of your, your groupies showing up in Pescadero.
Yeah. Oh, no.
OK. They'll probably be attending
some of your MBA. They'll come to the MBA.
Yeah, so. That was an MBA plug.
Yes, sure. This film is going to be shot in
Mexico. Yeah.
And. And you're excited about it?
Yeah, I'm excited about it. It's a, it's a film that reminds
(15:31):
me of, you know, films of like the late 90s or early 2000s, you
know, movies like Major League or, I don't know, Bull Durham
or, you know, just movies that, you know, were, were.
Baseball movies. Baseball movies.
It's a guy. Movies.
Yeah, maybe. Yeah, maybe not so politically
correct. Yeah.
(15:52):
So let's dive into that for a minute.
So because a lot of the films you've done and a lot of the
films your father's done have had a very strong masculine
element to it. But actually what's been
interesting about some of your films as well as your dad's
films is often it's sort of looking at the hero mythology
and saying, is that true? Right.
(16:14):
I mean, Unforgiven was sort of, you know, with your dad, it was
like that and Flags of Our Fathers, which was a, a film you
did with your dad 20 years ago. It is about like the mythology
of Iwo Jima and the the flag that was being hoisted and the
story behind it. And so there's where's your mind
in terms of the idea of masculinity in the modern
(16:35):
culture, especially with men. You have so much evidence that
younger men are struggling relative to younger women as
they go into adulthood, in university settings, in
earnings, etcetera. Yeah, You know, I, I, well, I
mean, we touched you. You asked a couple different
questions. So I'll start with the first
(16:56):
one. And I think, yeah, my father's
films have always examined, at least in the later years, they
examined, you know, the complexities of the character or
the human behind a, you know, a very, like, machismo man, right.
Like we're a lot of different Shades of Grey in this life.
(17:18):
And a lot of times that machismo, it has another side of
it too, Like as you're dealing with regret and, and you know,
all the things that humans deal with and that's, I mean, you
know, unforgiving sort of was like the the culmination of of
that, right? It's like this mythology behind
all that was a life of like, Hey, this is what I this is what
(17:41):
I fucked up on and dealing with that.
And I always find that to be themost interesting when it comes
to like complex characters because nobody is one thing.
And when you kind of like, now put it through the lens of like,
what is what is it to be a man? I think it's it's very complex.
(18:02):
I think that that's it's like just anything.
It's like there's no one way. It's like both things can be
true. How would you say you are
evolving as a man, say, comparedto your early 20s?
Like what is what? How would you say that you're
wiser as a human but also as a man today?
I mean, like in your 20s, you don't know anything.
(18:23):
You're, you're running, you're running and gunning and you're,
you're, you're being, you're, you've probably been affected by
culture and whatever you've, youknow how you're, you're, how
you're raised and then you're trying to figure that out.
I think if we're also for young men, I think we're dealing with
like a lot of like testosterone,a lot of fight or flight, sort
(18:45):
of, you know, responses to life scenarios.
And as you kind of age and get alittle wiser and you, you
realize there is like, there's different, different ways to
handle these situations. I think it it gives you like a
certain power as well to know that you can you, you don't you,
(19:09):
you, you can handle life situations with, you know, with
complexity. You know, it is interesting.
As we get older, we are less emotionally reactive, although
there are examples out there whodon't fit this profile.
But on average, our emotional intelligence grows.
Sure, as you're you're 39, you're turning 40 later this
(19:29):
year. In March.
Yeah, March. Early next year.
So you're sort of at that dawning of midlife.
How? Do you see midlife?
Like what is what is your perspective on?
We this the this is called the midlife chrysalis, apparently
because we're trying to remake the myth of the midlife crisis.
(19:50):
Yeah, the idea that maybe we're supposed to learn some things
and it's not about a crisis that, you know, your world falls
apart. Sure, maybe it does fall apart
in certain ways, but actually? On the other side of that
breakdown is a breakthrough. So how do you see midlife,
especially in the in as an actor?
I like that you're aging me right to my death at 80, so I
(20:14):
like that you're living. You calculated that my midlife
is 40. No no, no midlife.
Midlife is midlife lasts. Midlife lasts like 4 decades, 4
decades. So it's probably from 35 to 75.
That's my opinion. Sure.
Yeah, sure. Yeah, I think, I mean, you said
it sort of, well there. I mean, one door closes, another
(20:36):
opens. But yeah, sort of trying to.
I mean, I find myself this year specifically for a lot of
reasons, kind of taking a step back in the film industry and
taking a step back and, and liketrying to figure out what is my
(20:56):
next decade or two look like? What, what, what does that look
like? So I find myself like asking
myself those questions sort of on a daily.
And I think if you're not, you could find yourself sleepwalking
through your, you know, 40s and 50s and wake up and be like,
(21:17):
well, I'm not doing what I want to do.
Or, you know, I'm doing what some what someone else told me
I'm supposed to do. So I'm, yeah, I'm trying to, I'm
trying to sort of like take a 30,000 foot level of like where
I've been and and where I want to go.
Yeah. And this is, you know, one of
the classic questions of midlifeis, you know, am I living my own
(21:38):
life or am I living someone else's success script that I,
that I have been reading, to usea, a little bit of acting
metaphor. And, you know, if you were to
dream about something else you could do, like, let's get crazy
for a moment. Let's say you were not in the
film business. Let's say you were doing
(21:58):
something completely different and you went to an MEA workshop.
And at the end of the MEA workshop, you said like, OK, I'm
supposed to be a pastry chef or OK, I'm supposed to be a
firefighter or OK, I'm supposed to be what, what might be
something that you might find fascinating, maybe even from
childhood that you could resurrect.
(22:20):
Like for me, you, you we've beentalking about the, the, the Film
Festival, the MEA Film Festival.And you can, you've seen how
passionate I am about it. And, and I think back to when I
was younger, I wrote a screenplay in my early 20s.
I loved going to movies. I used to do, I used to be a, a
pretend movie critic in when I was 12 years old.
(22:40):
And. And So what might that be for
you? If I got to bring it back to my
12 year old self, I had this andI'm not sure where it came from
because it it my mom was confused about it, but I had
this desire to design houses where I would draw floor plans
(23:02):
as a 12 year old kid who's drawing like floor plans, like
kitchen floor plans and layouts for houses.
I spent a lot of time in Hawaii growing up being in like in real
nature and in warm weather. It still has like a I saw like a
calling for it so. That's that humidity thing.
(23:22):
We were talking about humidity earlier today and, and Maddie,
your partner and I was like, youknow, humidity can sometimes be
a pain and you're like, no, I love humidity, but that's, you
know, Hawaii has some humidity. Hawaii, yeah, You know, tropical
islands anywhere in the South Pacific.
I think if I'm like, if I if I'mlooking at this next thing and
(23:42):
what would be like fill my soul,it's something in the tropics,
something adventure, maybe taking people on tours or doing
something adventure and showing people under the stars at night
on Academy. I mean, I just that this is kind
of what I sort of see. I don't know what that is
(24:03):
exactly, but. Yeah.
Your father's 95 years old. If you were to live till that
age or longer, how would you seeyour life evolving in your 40s
and 50s and 60s and beyond? I mean, he he moved from acting
into directing and producing. You've done some producing.
(24:26):
I don't know that you've done any directing yet.
Is that something you'd like to do?
And what you know, you, you've said both to me personally as
well as in the press, like filmsare a director's medium because
they really control things, which can be hard because
sometimes a film comes out and you're like, Oh my God, there
was so much good stuff that never made it, you know, into
(24:50):
the final cut. Is directing something that you
would see yourself potentially doing as you get older?
Because in some ways director, you could see a director having
wisdom that you build over time.Before I, as my dad would say,
before I hang up my spurs, I, I'll definitely give it a shot
directing. It's, it really is film is a
(25:10):
director's medium. You know, the director is really
making all the, all the decisions.
They're, you know, it's a collaboration, but they're
hiring the departments, right? They're the CEO.
So they're hiring the departments and then directing
those departments accordingly. Set direction, locations, saying
no, I want something more grand.I want something with bigger
(25:31):
vistas. I want feel something that feels
older, you know, make it this, make it that the wardrobe, all
the departments, all those decisions from the pre
production of a film all the wayto its completion and it's post
production. It's all director driven.
And I like that because it's it's it's a it's the whole
(25:53):
process. Every decision is a creative
decision you're making for better or worse.
But I don't think I would want to just sort of stay in in the
current position where I'm just an actor for hire and not I'd,
I'd rather fail on my own terms.You know, I'd rather go out
(26:15):
there and take some swings than just, you know, because you
sometimes you get on a film in your go, OK, I would not be
doing it like this. You've been around enough.
You could go. I've seen it done this way and
I've seen it done this way. And I know that way is not going
to work or not going to look good and then you're on.
But I don't really, I don't really have a lot to say here
that the trains already left thestation.
(26:37):
So you're kind of, you're kind of going, you start to start to
chip away at you a little bit and go, I got to, I got to, I'm
going to give this a shot on my own.
How soon? Soon.
So you got to find the well, theproblem.
The problem is, is you got to find the right material.
And I don't like to write. I like the collaboration of
reading something and giving notes and having an idea and
(26:59):
having other people write it. But this right here is, is
really tough. Like, you know, my hat goes off
to the riders that do it well because it's, it's a, it's a
hard thing to lock yourself in aroom and be isolated and, and
put pen to paper. So I want to explore this idea
of time and as we get older, time becomes more valuable.
(27:22):
Maybe we we talked about regret earlier.
Maybe we might actually think about the things that we wish we
had done. One of the questions we like to
ask at MEA is 10 years from now,what will you regret if you
don't learn it or do it now for you?
Because anticipated regret. The thing I like OK at 49, I
(27:43):
will regret that I didn't do or learn this in my 40s.
What comes up for you when you think that?
Because for me, I'll I'll just as when I moved to Baha where we
both you'll be living soon enough part time.
I had a a mindset at age 56. I was too old to learn to surf
(28:04):
and I was too old to learn Spanish.
But when I put it in this framework of 10 years from now,
what will I regret if I don't learn it or do it now, knowing
that I might still live part time in in Mexico at 66 near a
surf break, a couple surf breaksand also, you know, a place
where everybody's speaking Spanish.
(28:25):
It gave me the catalyst to say Igot to learn Spanish.
I got to learn to surf. Now I'm not very good at it
either, but it actually got me off off my Duff.
So what might you regret if you don't learn it or do it now, or
at least sometime in the next 10years?
I feel like I've, I've accomplished a lot of, you know,
(28:47):
the, the sort of action sports things physically, a lot of
physical things that I've wantedto do and became, you know,
learned how to spearfish and jiujitsu and Muay Thai and surfing.
And even though I am still a beginner at certain things,
which I love being a beginner, like I, I started foiling last
(29:09):
year and, and that became, you know, sort of not a beginner at
that. And then I started trying to do
like a wing foiling, which is sailing and foiling at the same
time. I feel like a lot of like
physical stuff I've done. I think what I want more now is
more intellectual stimulation, so.
That's why you're hanging out with me.
(29:29):
Yeah, Yeah. You know what I mean?
I mean, it really is. I mean, as I evolve as a human,
I want deeper relationships. I want more.
I want relationships to challenge me intellectually,
challenge my thoughts, get me reading more, get me interested.
I'm I'm definitely someone who'salways like seeking more
(29:50):
knowledge, information, whether that's through podcasts or books
on tape. I also think this is going to,
this is broad, but if I don't follow my gut on, on, you know,
in 10 years from now, I think I'm going to be, I think I'm
going to be upset with myself sothat that's, you know, hey, I
got to give this directing thinga shot or hey, I got to do this
or I've got a, you know, you're going to follow my gut.
(30:11):
When you don't follow your gut, that's when you really get upset
with yourself. And that's a lesson you learn
from your dad, isn't? Isn't that one of his key
lessons he's taught you? Follow your gut.
Any time I've said yes to a job and I've kind of known it's not
the right thing, it's not the right deal, I've done it for
money or I've done it for other reasons or as my agents or
(30:32):
whatever saying, oh, you got to do it, you got to do this, it's
great. You know, it's good for your
career. Whatever is that other voice
that if you listen to that othervoice and you don't listen to
your gut, it usually, it usuallysteers you wrong and then you're
upset. The only person you can be upset
with is yourself. So I think just listening to my
(30:53):
gut, yeah, that's the biggest thing.
So longevity's become a a hot topic everybody.
'S a lot of experts out there. A lot of experts out there, a
lot of people trying different things.
And one of the things I've neverdone is something you did when
you had a a broken ankle and youwere filming The Outpost, a film
(31:18):
that was very highly regarded about Afghanistan, the war in
Afghanistan in a particular battle that happened there.
So you ended up in a hyperbaric chamber to actually speed the
healing, the healing of this ankle.
But tell us a little bit about that movie because it's actually
one of I think, you know, one ofmy favorite movies of yours and
(31:40):
one of the highest rated movies of yours.
What what happened? How'd you break your ankle, if
you want to talk about that? And what was that movie like?
And and how, how do you think about your own longevity?
So, yeah, I, I actually, this was, I think it was in 2018 or
19, I was set to start filming the Outpost in, in Bulgaria,
(32:05):
which we were dubbing for Afghanistan.
And I, I, it was about six weeksout from shooting and I broke my
ankle and I called the director and the producer give them this
news. But I told them the doctor says
it was a little bit of a white lie.
(32:26):
The doctor says that I'll be ready in three to four weeks.
Fine, it's good, good to go. Which I knew really wasn't the
case because anyone who knows whoever broke in a bone, it's
like 6 weeks off of it and then you have to sort of do the
rehab. But I was very determined to do
it and they they sort of stuck with me, which I was surprised.
(32:49):
I said, well, that someone else will to go didn't make that
movie. So I did everything you could
possibly do. I was in the hyperbaric chamber
every day or every other day. I started doing physical therapy
before the doctors told me to doit.
I'm under the like belief that you want to keep it.
You know, you got to keep it isolated, but for for a while,
(33:10):
but then you need to keep it. You need to start moving it.
And I ultimately started that movie in a cast because I got
there and I wasn't really ready to be running.
Yeah. Because it's a very physical.
Movie, It's a very physical movie.
Yeah. So I started in a cast and you
know, this, this wasn't really Rods.
(33:30):
Rod Laurie, who was our director, wasn't his dream
because I know he had some some wonders that were that that he
had designed for the film. What's a wonder?
A wonder is when you when you shoot a a scene in one shot, so
the camera might move around andand go back and forth to
different actors, but you're notsort of like adolescents.
(33:52):
Sort of like adolescents, which I which I you believe I.
Think, I think, I think it's bullshit.
I think they did like 4 wonders and they stitched him together.
But that's that's where I'll die.
I guess I'll die on that hill. But yeah, so they had to sort of
design some shots for the first week or two around me.
And then I was, but I was doing so much physical therapy and I
(34:15):
was so determined to like get going that by, you know, we
three, I was pretty much running.
But yeah, it was a, it was a tough, it was a, it was a tough
moment. It was, it was a, it was a
moment that really like, you know, you put your, you know,
your mortality a little bit because, you know, I hadn't
really broken a bone since I was, you know, 1520 years prior
(34:37):
to that. When you're anyone who knows
who, who's ever been injured, it's it's man, it's a mental
like it's some is it takes you, especially someone like me
who's, who's so physical and like part of my daily routine or
part of just my life is like allthese physical hobbies.
So when you're, when you're, youknow, mandated to not be able to
(34:58):
move, I mean, it's, it's rough. It's mentally, I think that, you
know, it always gets you thinking about, OK, like, life's
pretty fragile. Yeah, yeah.
Do you have a favorite longevityhack?
I mean. I mean, I mean.
From a Wellness perspective. Yeah, what do you?
What do you really you? Know, and I'm not an expert by
the way, 'cause I actually I sort of despise all these health
(35:22):
experts because most of them areschlepping something and that
really bums me out 'cause you know, I want people to learn
about health and Wellness without having to be sold
something. And I think there's so much you
can do without taking anything, just the basics, the the
fundamentals, right? Working out, stretching, sleep,
(35:44):
mental, spiritual. Health.
Nutrition. Nutrition, there's so much that
social, yes, community, there's so much in just the the
foundation that you don't need to buy a product and you don't
need a guru to tell you about. But the foundation for me, you
asked the question is the foundation for me is some sort
(36:06):
of yoga daily, whether that's 1520 minutes in the morning or
prior to a workout. Stay hydrated, eat Whole Foods
and try to get to bed early. Try to stay off any devices.
Try to get your circadian rhythmin a good clock where when the
sun sort of goes down, you're sort of going down.
(36:27):
Yeah. So that's sleep and then some
sort of spiritual component if you can and like a communal
component because I think communities and you sort of look
at the what they they talk aboutthe blue.
Zones right, Right. These are sort of the
fundamentals they all had. They all take into those
(36:48):
categories. Or eaten Whole Foods.
They're do it, they're active, they have a communal, they have
a spiritual aspect. And that I just try to sort of
like look at, you know, holistically.
You are wiser today than you were 5 or 10 years ago.
Sometimes what we consider common sense is through the
school of Hard Knocks. Since this podcast is called the
(37:09):
Midlife Chrysalis, I'm early so.Don't count me out.
Yeah, let's say. Anytime in adulthood, from age
18 on, what's a challenge you went through that may have
kicked your butt for a while andyou learn something from it?
You got wiser. If our painful life lessons are
(37:29):
the raw material for our future wisdom, what's an experience you
had that kicked your ass? But you're happy it happened at
the end of the day, because if you're not happy, but you're,
you're happy with the way you metabolized it, sure, and and
learned from it. I think in my early 20s, I was,
(37:50):
you know, I was so focused on, on trying to create a business,
be successful, which I, you know, I, there were things I
started and, and failed at. I tried to launch a whiskey
company. I tried to do a couple variety
of different businesses as I was, you know, working as a
bartender and I was and a valet car Parker and as a young man
(38:15):
you, you know, I, I felt so trying to, you know, trying to
do something but not understanding.
And if it didn't work and tryingto control it and you can't, you
can't control life like you can't.
There's some of some of you haveto let go.
You can work hard. You can put your head down.
It may work out, it may not. Usually hard work sort of
(38:38):
Trump's everything. You will get successful if you
work hard at anything. It's a it's a strange dichotomy.
Sometimes you just have to push harder and sometimes you have to
let go. And that's why the Serenity
Prayer is so powerful. You know, grant me the serenity
to accept the things I cannot change.
To change the things I can. That change the things I can and
(39:01):
the wisdom to know the difference.
So it's really it's the serenityprayer, but it's also the wisdom
prayer. It's really about, like,
understanding wisdom is really about understanding what are the
things you can control. Yeah.
Or influence, and what are the things you have to let go.
Yeah. And you know, that is, to me,
like the ultimate learning when to surrender.
(39:22):
Yeah, is. It's hard.
It's hard. And it's still hard.
It's still a thing. You got to go.
Yeah. Wait, wait, bro.
Yeah, you don't know, but you know, like am I supposed to let
this go? Am I supposed to just push
harder? You know, this is where friends
are helpful, family members are helpful to like be the objective
1 giving you some some indication.
So how would you like people to use?
(39:44):
What words would you like peopleto use to describe you?
Like what adjectives today in terms of who you are on a good
day? I guess one of the mantras I try
to live by, I don't know if I want it's hard like having
wanting my friends to describe me in a certain way because I
guess that feels slightly narcissistic or no.
(40:05):
This isn't meant to be narcissistic because they will.
First of all, let's just say they will be describing you in a
certain way. And one day.
They always do. I mean, people talk about it,
you know, you know, companies have a, a, a brand and we have a
reputation. So the and and, you know,
especially if you're a high profile person out in the
public, people will say, oh, he is and they'll describe you as
(40:29):
one, 2-3 different adjectives. I guess reminds me of, I think
it was a poem that I I, my mom read me as AI was a young man
and sort of it's sort of like life isn't about the material
things. It's not about what clothes you
(40:51):
have or who your friends are or aren't, but it's about how you
affect people on this planet, onyour in your time here and
either a positive or a negative way.
And that really could never occurred alone.
And that has stuck with me. So I hope that I have affected
(41:14):
more people positively and they,you know, given them, inspired
them or, you know, been kind to them or been graceful in my time
here before we're dust and bones.
And that's kind of I guess if like I was said to still it
down, that's what. And and if you have one lesson
you've learned from your mom andone from your dad, what might
(41:37):
those be? That was definitely from my mom
because she was OK. She was, and she is still.
She's still living. Yeah, she.
Is yeah, she was real soulful inthat way.
And I love that because it's just it's so easy to get caught
up in, you know, and what you think is important and none of
that stuff. I remember when my buddy died,
(41:59):
he he passed away and we went, he was very successful guy.
And we went to like box up his stuff at his house and help out
and, and do the stuff and like sort of clean up and like, you
have to do all these things. And you realize like none of
this shit matters. Like the jeans and the things
and stuff. It's like, yeah, you know, you
(42:20):
need, you need a certain amount of that.
It's nice to have a sweater on acold day.
It's like none of the, none of this stuff that I, you know, at
one point in time I was like, oh, that's so cool to, you know,
have or whatever. And then you realize it doesn't
matter, you know, because you'renot guaranteed tomorrow.
And so, yeah, I just, I don't know.
That was that those were lessons.
I don't know necessarily if it was my mom or my dad or our
(42:42):
combination of both. My dad was, you know, I, I
always, always got to give it tomy dad for, for giving me like
hard work and discipline, work ethic and at times very tough
lessons because he was, he was so old school.
Like you're on your own, figure it out, you know, like you're,
you got to go make it as a man in this world.
(43:02):
Like I'm not here to help you. You got to go.
You got bills to pay, you got stuff, you know, and that I
think that's an is like is an important part of being a young
man and trying to like figure itout and, you know, scratch and
claw and learn the value for a dollar.
Have you had any mentors in the the film industry that you can
(43:25):
look to and just say like, yeah,I, you know what I admire, even
if you don't know the person? Sure, I admire them because fill
in the. Yeah, yeah.
I mean, I mean, I've had different mentors through the
years, you know, older friends, you know, sort of like 10 to 20
year my seniors through my life that have always been a good,
like, you know, a good person too give a call to and say, Hey,
(43:48):
I'm going through this or I'm trying to make this decision.
And I think that's really important, right?
Like having a mentor and eventually being or sorry,
having a mentor and eventually becoming a mentor because you
want to pay that forward, right?And so I've done some of that.
I've, I've taken a lot of meetings with young, younger
people who want to be actors or whatever, want to, you know,
(44:09):
advice about the film industry. And I'm always like, my doors
always open for that. OK, so let's say, let's say
someone 1015 years younger than you comes to you, Scott, and
says, Scott, can we have coffee next week?
I know how much you like coffee,Scott.
So what if we have coffee next week?
And I want you to come to the meeting with one Wisdom bumper
(44:32):
sticker, something you've learned, Scott, at 39, that has
had a profound impact on you. What's the bumper sticker, the
wisdom bumper sticker that has your fingerprints all over it?
And what's the origin story thatled to that wisdom?
Because again, our painful life lessons are often the raw
(44:53):
material for our future wisdom. So what might be?
And it's a hard question, no? No, I, I, I actually, I know the
bumper sticker because I think about it often when I'm making
decisions. When your values are clear, your
decisions are easy. And I think that wraps up if you
(45:14):
know, you kind of go back to that when you're, you know,
because decisions are tough. Decisions are some of the
toughest things you're going to do in life because you wrestle
over them. Once you sort of made a
decision, then you, you start onthat path.
But I think, yeah, the the clearer you can, you can really
know what your values are, then the the clearer easier it is to
(45:34):
go, Nope, that's not in my valueset.
And I'm not going to sacrifice my principles because of money
or because of a thing that someone else is telling me to
do. And did you learn a lesson from
the past based upon that? Oh man, probably, probably 1000.
But I actually randomly I heard it from an agent.
(45:58):
I heard it from an agent. And I always thought it was, it
was quite profound coming from an agent where sometimes they're
not as profound to be. But yeah, I thought it was
really, I thought it was really profound.
And, and it's just the, the older I get, the, the, the
easier it is to just put that inperspective and, and that that
(46:19):
be the North Star. Off the top of your head, what
might be some of those values today?
Integrity, honesty. You know, when you say you're
going to be somewhere or do something, you got to follow
through with that. When you make an agreement with
someone, it doesn't need to be done by a lawyer.
It needs to be look, so it lookssomeone in the eye and shake
(46:42):
their hands and you say you're going to do something.
I mean, that's how it used to be.
You know, there's a great book called The Code of the West.
And if anyone, there's someone, everyone should buy this book
because it's just, it's the simple principles that make us
inherently good to each other asa community.
You know, you know, a lot of these principles you, you, you
(47:04):
find in, you know, religious texts, but a lot of them are
just, you know, very regardless of what religion you are or not,
they are principles that are just guiding principles.
And yeah, that, that's somethingmy dad was very, you know, he's
very vocal about like you, you know, you know, you, you say
(47:25):
you're going to do something, you know, you do it.
You follow through with your commitments.
You, if you set out to do something, you know, whether it
be the plumber or a Carpenter orwhatever, you go out and be the
best version of that. You don't mail it in.
You, you do the, you do it once,do it right, You know, do it
with some pride. Have some pride of your owner
ownership, whatever you're creating, those are sort of
(47:48):
them. And there's some more, I'm sure.
No, I, I, I feel your passion onthis so.
Also, it's it's a thing for me. It's like I think that is one of
my passions. I see in like pop culture where
I don't see that. I don't see a voices saying be
someone of integrity. You don't, you know, like we, we
live in this like litigious society and a society where it
(48:11):
becomes about culture and money and Instagrams.
Yeah, yeah, you got to have thisto be successful and happy.
And it's like, I don't see people pushing that narrative.
Like, yeah, like, you know what?Do something of value that that
makes you feel happy and, and bean integrity person with
integrity. Because I think that I don't
(48:33):
know. But in my opinion that that
narrative and that those values,we'll, we'll find you in a place
where you're a lot more. And you'll be passing those
values on to your kids, your mentees, your, you know, the
people who follow you. So thank you very much, Scott.
It is an honor for us to have this conversation.
(48:55):
Yeah. And that's how I.
Want to be here? See the ranch.
Yeah, yeah. Scott got to stay at both of my
both of my houses, the house in Baja before we came up here and
then the house here. And I really appreciate that our
friend, our friendship is just continuing to grow well.
Thank you. Yeah, I wanted to actually give
some context at the end of this episode to my relationship with
(49:21):
my dad again, because when I talk with Scott and there are a
couple things that came up with Scott after we finished the the
episode cut cutting, then recording it that I wish I could
have included. Number one is that, you know,
how much Scott loves his father,how dedicated he is to his dad
(49:42):
at this age in his life. And just to see his dad as a
role model for aging in his mid 90s.
But his dad's pretty much like, OK, there's one way to do
things. His dad's an extreme introvert.
So at times, Scott has had to find his own path, like I had, I
did in terms of like Scott's, you know, a bit of an extrovert.
And additionally, one of the things that came up in my
(50:05):
conversation after the recordingwas that Scott had a near death
experience, not quite like mine.Yeah, just I'll tell you about
about it for a second. And then.
And then I have a story for you that includes my dad.
When Scott was in a a war movie,I can't remember which one it
was, but he was in a helicopter on a hill and the helicopter was
(50:27):
coming down and landing on a hill.
It was a tough landing. By the way, both Clint and Scott
know how to fly helicopters. And when it came down and, and
then Scott was supposed to get out of the helicopter, the
helicopter lurched such that while the while the the
(50:48):
helicopter whirls were happeningit they almost cut his head off.
It was within, you know, just a couple feet of actually missing
his head. And this is as the helicopter
sort of lurched down the hill. So he didn't, he didn't go
unconscious, but he could not, he could not be filming anything
(51:09):
anymore that day because he was so shaken by it.
So I want to just tell you a story that I haven't told on
this podcast yet. And people have said to me,
Chip, we love the podcast. We love what you're doing.
We want more of your stories. So I'm going to just give you
one of my personal stories that's a near death experience
that includes my dad. I'll just say that I've spent my
(51:31):
life running. I have, you know, in 6th grade
in as an elementary school student, there was one point
where lunch was over and I was doing laps around running around
the the playground and I couldn't stop.
I literally couldn't stop. And it was just a mental thing.
And so finally Missus Epperson, my 6th grade teacher, came out,
(51:54):
pulled me by the ear and said you're supposed to be in the
classroom. But I've had a thing about
outrunning fears and and maybe not feeling good enough.
Being an admiration and achievement addict, partly
because of my fear of disappointing my dad, I became a
success, a big success in the the hotel industry.
(52:15):
But in my late 40s, everything started to fall apart.
And this was my midlife chrysalis.
I've talked a little bit about this on the podcast before, and
I was trying to outrun my emotions again.
I had a life that was a bit overstuffed in plot and I just
needed to figure out how to unstuff my my full life, which
(52:36):
didn't feel like a very happy life.
I had a friend named Chip, not me.
This is not me talking about myself.
His name is Chip Hankins. He was my insurance broker, he
was one of my closest friends. He's somebody I I really look to
for spiritual advice and guidance.
By his mid 40s my friendship hadmarried 5 different people as
(52:59):
the officiant in the wedding andso he's loved.
A very well loved guy. He was married, had two kids,
lived part time in New Zealand where his wife was from, and
part time in the San Francisco Bay Area.
So on April 30th, 2008, I was inSaint Louis about to give a
speech to 1000 people and 5 minutes before I was going on
(53:20):
stage, I got a call from Chip's boss, the president of the
insurance brokerage, telling me that Chip had taken his own
life, which is so hard to hear. Hard to hear, you know?
I ultimately had. I lost 5 male friends to
suicide, ages 42 to 52 between 2008 and 2010.
So Long story short is I took note, I had to go up on stage,
(53:43):
give my speech and then afterwards I really, I just
like, wow, I, this was such a surprise.
Chip was, I would never would have guessed that Chip was in
that kind of trauma and he, he had a lot going on in his life.
A month later, this happened in New Zealand.
A month later, we had the memorial service for Chip and to
have everybody get up, go up on stage and give their Chip
stories. While I was going through a
really hard time during that time, I'd had some suicide
(54:05):
ideation myself. You know, I wanted to escape.
I had a a long term relationshipthat was that was probably
ending not by my choice. I had a foster son who was an
adult who was going to prison wrongfully.
I didn't want to be CEO of the company I'd started, you know,
more than 20 years earlier. And we were running out of cash
(54:25):
during the Great Recession. So here everybody was coming up
and giving their chip stories atthe memorial.
And I was like, oh God, you know, it's like being at your
own funeral. And then a month later I broke
my ankle playing baseball at Gavin Newsom's bachelor party
for his 2nd wedding. I got a cut on my leg, didn't
realize I had fertilizer from the baseball field on my leg.
(54:48):
And I ended up going septic on my leg for the course over the
course of the next two or three weeks, Finally got to a strong
antibiotic that seemed like it was working.
And then of course, I should have stayed home.
But being the runner, I got to go do this.
I got to go do that. I ended up on the road giving a
speech in Saint Louis no less, where I'd heard about Chip just
(55:09):
a few months earlier. I'm in Saint Louis now giving a
speech and while giving a speechon crutches on an antibiotic,
when I sat down to to sign booksI went unconscious.
They put me on the ground and the paramedic showed up a few a
few minutes later and I went flatline.
I died. So I had a near death
(55:29):
experience. I literally went to the other
side 9 times over 90 minutes. People ask all the time, what
did you see on the other side? I was like, I saw birds.
Birds were talking to me and it's a longer story, but I'll
keep it brief right now and justsay I could.
I'm like, I'm sitting here rightnow in the recording studio
listening to birds outside. When I hear birds when in, in
(55:51):
the, when I was in this flat line experience, I could
understand what they were sayingto each other and to me and they
were telling me to slow down andsee the beauty and awe.
So ultimately I lived, of course.
And on the other side of that, it allowed me to change
everything. Relationship ended, got my my
foster son, adult foster son Damien, out of prison and sold
(56:13):
the company. But it was my father who showed
up in the hospital when they hadno idea what was wrong with me.
They didn't realize it was an allergic reaction to, to my
antibiotic, but they thought, you know, it might be something
more serious. He showed up and he was there
for me and I loved him and he loved me.
(56:33):
And he just told me how many. He told me so many times how
much he loved me. My father, at age 47, I was at
47. He was at that point in 69.
He was just telling me how much he loved me because he didn't
know if I was going to continue to live.
I tried to convince my dad, OK, yeah, I'm here in Saint Louis.
I'm supposed to go to Toronto for a for a speech in Toronto
(56:55):
and then I'm supposed to go to Houston.
And my dad said, well, you're not going to Toronto because
you're going to be in the the hospital.
So we have to cancel that. But I hear how much you want to
be in Houston. You want to speak to these 100
entrepreneurs about what it means to be an entrepreneur
because this is actually what you want to do next.
He realized he heard me talking previous to me, my flat line
(57:16):
experience, about the fact that I didn't really want to be
running my company anymore. And then I have this flat line
experience and he is there to see, as he said to me on the
flight back from Houston, after I addressed these entrepreneurs
and did a little workshop for them for four hours, he was in
the back of the room watching meto make sure I didn't die on
stage. He said, Chip, I came here
(57:38):
wanting to make sure you didn't die.
I have seen now how you want to live.
We need to figure out how to getyou out of this straitjacket of
this company that you started, this Frankenstein that at this
point you have outgrown so that you can do the thing you're
supposed to do, which is to write books, be a speaker and
(58:01):
explore, you know, what's next for yourself after age 50.
So for the next two years, my father, who I had that very
difficult relationship with whenI was younger and in my early
20s when he sort of disavowed mefor who I was.
My father was there for me in mytime of need.
And quite frankly, in many ways,my father was the one who helped
(58:24):
me to have the courage to actually let go of this identity
of the CEO and founder of the second largest boutique hotel
company in the US, an achievement that in many ways
defined who I thought I was. And of course, I went into my
50s and had the time of my life and loved my 50s, had time to
(58:45):
figure out what was next and then Airbnb and then MEA.
So I just want to finish by saying I wish this was playing
on Father's Day because I just want to say thanks to dad.
Just as Scott has had a challenging relationship but a
loving relationship with his dad, I've had the same.
But over time I have found that he's become one of my best
(59:07):
friends. Hope you enjoyed this episode
and look forward to seeing you next week.
Thanks for listening to The Midlife Chrysalis.
This show is produced by MidlifeMedia.
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