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December 17, 2025 23 mins

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.


In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.


Chip shares:

• The three stages of every transition and where most people get stuck

• What really happens inside the messy middle

• Why men and women experience midlife so differently

• How transitional intelligence (TQ) helps you move forward with clarity

If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need.

If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights.


Timestamps:

00:00 Film Festival & Holiday Mood

01:55 Crisis vs Chrysalis and the Hollywood Myth

05:15 The Three Stages of Transition

07:07 Emotions in the Messy Middle

09:33 Finding Your Through Line

11:21 Ritualizing Endings

13:16 How Men Experience Midlife

15:40 How Women Experience Midlife

15:53 Why Women Navigate Midlife Differently

19:27 Identity, Purpose, and Feeling Stuck

21:35 Chip’s Personal Midlife Story

22:42 Why Men Resist This Work


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


#MidlifeChrysalis #MidlifeTransition #MidlifeCrisis #MessyMiddle #PersonalGrowthJourney #LifeTransitions #ChipConley #TransitionalIntelligence #MidlifeWisdom #SelfDiscovery #MidlifeWomen #MidlifeMen #EmotionalWellbeing #LifeReinvention #GrowthMindset

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
When someone feels like they're stuck in the chrysalis, it's as
if they're going to be just liquefying the rest of their
life. And that is why the chrysalis
metaphor is so important, because if you think you're in a
crisis and you think you're never going to get out of it
again, and it might take a little while, Bruce Feiler's
work shows that it takes three to five years sometimes to go
through a transition. Although if you have TQ and you
can navigate your transitions faster, then you can go through

(00:20):
it more quickly and adeptly. But it's the understanding
during that that period of time in the messy middle, what you
really need to know is that you're going to get through it.
The Midlife Chrysalis Welcome toWisdom Wednesdays with Chip
Conley and Derek Gale, your weekly conversation about
thriving in midlife. Together, we explore the
questions, insights, and practices that help you live

(00:42):
this chapter with more purpose, vitality, and joy.
Welcome to another episode of A Wisdom Wednesday at the Midlife
Christmas Podcast. Chip, how are you?
I'm, well, I mean, I'm getting excited about Christmas.
We are right now in the midst ofour MEA Film Festival, film
Fest, which to me is, I'd like the cherry on the top at the end

(01:03):
of each year. This is the second year we're
doing it with 60 film makers, 60films, almost 60 attendees.
And it just it, it's a deep experience of being able to not
just watch films with other, youknow, cinephiles, people who
just love films, but also to spend a week with the film
makers and to go for hikes with them and go take a hot tub with

(01:26):
them and have a meal with them and be in a yoga class with
them. So it's not just having AQ and
a, which is what film festivals tend to do is like you watch a
film. I remember going to Toronto Film
Festival, going back to Canada during the Toronto Film
Festival, which is a great Film Festival, one of the best in the
world. But you know, you'd watch the
film, you know, it was like, Oh my God, that was an amazing
film. You'd hear the 30 minute Q&A

(01:47):
with the director and then you go outside and all of a sudden
that Crucible you were in where everybody was feeling the same
thing. It's gone because you're out on
the streets and Toronto's a hugeplace and like, no, I want to go
to a Cafe now with all this group of people and talk about
this. So most film festivals don't
really have that. They you, you, it's sort of you
watch a film, you hear interesting person, you know,

(02:08):
actor or filmmaker. And for us this week, it's
really about actually getting toknow these folks as humans.
Yeah. So I'm, I'm just really proud of
that. Feeling good about that.
And then had to spend Christmas with the family and.
Yeah. Are you in Baja for that?
I'm in Christmas with my family in the Bay Area, and then I go
to Baja. I will be in the Baja for a

(02:30):
while. So, yeah, good.
OK. Well, let's let's dive into this
episode. And I want to explore the
concept of the chrysalis. Yeah, which is is is such a
breakthrough for a lot of people.
It's, I mean, I have to say the first time I ever came up with
this idea and I love language asI think people know.
I, you know, it's part of the reason I have a daily blog

(02:51):
wisdom. Well, when I realized that
crisis is chrysalis. I mean, first of all, sometimes
people don't don't they don't pronounce chrysalis right.
They say chrysalis is like, where where'd you get back?
Like it's chrysalis. Dumb dumb fuck chrysalis sounds
like crisis. And we learn about the chrysalis
as kids because what we learn about is that metamorphose

(03:13):
journey, the Caterpillar to the butterfly and it's the chrysalis
that's the in between stage. So the chrysalis is both pain
and suffering. It's the liquification factor of
the the Caterpillar moving to the butterfly, but it's also
where the transformation happens.

(03:33):
And so that's the piece we miss there.
There's the crisis, this idea ofa midlife crisis, which in pop
culture is, you know, I've been embodied by Lester Burnham in
American Beauty. That's Kevin Spacey.
Or Don Draper. What's his name?
The actor of Don Draper in Mad Men.
No Ham. His last name is Ham.
Jon Ham. Jon Ham, Exactly.

(03:55):
Or Tony Soprano in midlife crisis.
Or Bill Murray, as Bob Harris inlife is in the Transitions.
We frankly did you notice that all four of those were pop
culture icons and were men. So we tend to think of the
midlife crisis as being a male thing.
But we're going to, I'm going totalk in a few minutes about how
men experience midlife and theircrisis versus women.

(04:17):
But only 10 to 20% of North American humans in midlife say
that they've experienced A midlife crisis.
That's based upon research from Midas MIDUS, which is the most
comprehensive study of life everdone.
I think it's from University of Wisconsin.
So midlife crisis is sort of a Hollywood trope.

(04:38):
It's this thing that OK, as as Kevin Spacey did in American
Beauty, you like you're you've all of a sudden realize the
script you've been living no longer is relevant and you buy a
red sports car and have a potentially an affair with your
daughter's high school best friend.
Not a good idea. So.

(04:58):
And and so what's really going on for people in midlife is
they're going through this low point that we've talked about EU
curve of happiness. And what people mistakenly think
is that they're going to be stuck in that crisis, that
chrysalis forever. And that's why one of the most
important things that we teach at MEA is transitional
intelligence. TQ Great credit to Carry

(05:20):
Cardinali who came up with that and we've trademarked TQ and so
or transitional quotient. There are three stages to any
transition and this comes from indigenous people rites of
passage work. Margaret Mead comes from Joseph
Campbell's work for hero's journey.
The three stages of the hero's journey comes from William
Bridges work wrote a book calledthe transitions or Bruce

(05:43):
Feiler's work life is in the transitions.
My podcast with Bruce Feiler. You can listen to that one
because that's on the midlife Chrysalis podcast.
So we get there's these three stages, the ending of something,
the messy metal and the beginning.
So the ending of something is often when you are ready to let
go of something. And for a lot of people, they

(06:05):
have a really hard time. I'm just saying goodbye.
And that's why the one of the most important coping mechanisms
in that stage is to learn how toritualize it.
And Mea, the first, very first again, the, the very first day
we do this collective ritual, wecall it the great midlife edit
in which you're letting go limiting beliefs or mindsets,

(06:26):
fixed mindsets that aren't serving you anymore.
And that's really important because when you're actually in
the midst, if there's a metamorphosis you're supposed to
go through, you can't be the Caterpillar forever.
You know, the thing that's interesting about the
Caterpillar is in the last two weeks before a Caterpillar spins
its chrysalis is eating more. It's actually bulking up.
And in some ways in our 30s and our early 40s, we are working

(06:49):
more. We're we're sort of bulking up.
Yeah, in the sense of, you know,we're really like revving up
and, and we have no time to ourselves.
And, and then we move into the second stage, which is the the
chrysalis stage, the messy middle.
And that's scary. I mean, there are a lot of
emotions that we feel like when you're in the midlife, you know,

(07:10):
the chrysalis or the messy middle.
You, you, what are the emotions that we feel?
I got confusion. Anger, Anger, Feeling stuck or
bewildered? I mean, stuck is probably the
number one word we hear at MEA. That is so true.
Yeah. Yeah.
So, so. And that's so right on, Derek.
Because when someone feels like they're stuck in the chrysalis,
it's as if they're going to be just liquefying the rest of

(07:32):
their life. And that is why the the
chrysalis for so important, because if you think you're in a
crisis and you think you're never going to get out of it
again and it might take a littlewhile.
Bruce Feiler's work shows that it takes three to five years
sometimes to go through a transition.
Although if you have TQ and you can navigate your transitions
faster, then you can go through it more quickly and adeptly.
But it's the understanding during that period of time in

(07:55):
the messy middle, what you really need to know is that
you're going to get through it and you need social support
because often you are not thinking, you know, properly
during that time. Get fixated on the thing that
you're in transition on, whetherit's a divorce or getting fired
or a cancer diagnosis. And you think your whole life
revolves around that. And your friends are the ones

(08:16):
who are tell you you're lovable no matter what, and you're going
to get through this. The other thing that is helpful
in the in the messy middle is tofind your through line, which
means on the other side of this,how are you going to be wiser?
Our painful life lessons are theraw material for our future
wisdom. And so being able to say, oh,
like Viktor Frankel, you know, was in concentration camp and he
noticed that the the people who actually didn't die, we're not

(08:37):
necessarily the ones who are the, you know, the most
healthiest. Sometimes they're the most
infirmed, but they still have a sense of hope and meaning.
And on the other side of this terrible experience, and they
were going to be a better grandmother or they were going
to write their memoir or whatever it was.
So that through line, it helps you to see like on the other
side of this, you know, if I've just gotten divorced and I
didn't want to get divorced and now I'm actually creating my

(08:59):
match.com profile, I'm like, oh,fuck, like after 30 years of
marriage, I'm now doing this. But to be able to see that, OK,
when I start dating again, I am going to be wearing a new pair
of glasses and understand who isthe right spouse for me because
my last spouse wasn't the right spouse for me.
And that's something you only got through, you know, the

(09:19):
school of Hard Knocks in the third stage of any experience of
transition after mess, after theending, in the messy middle is
the beginning of something new. And that's the that's the the
butterfly. And what's interesting about
butterflies is when they emerge from the chrysalis, they often
land on the ground first becausetheir wings are wet and they've
never flown before. So they don't have any

(09:41):
experience. And that's why the most
important coping mechanism in that new stage that that post
chrysalis stage, that post crisis stage is to be have a
growth mindset. And we talked about that in a
recent episode. But when you have a growth
mindset, it means you're willingto try things and not be self
critical. You know, a growth mindset is

(10:01):
like, OK, I can have a sense of humor.
And it's like, like a baby doesn't have a fixed mindset
when they're, when it's learninghow to walk.
Everybody's staring at the baby and pointing at it.
But if everybody was staring at you as an adult and pointing at
you at doing something you don'tdo, well, you stop doing it.
But you actually, when you have a growth mindset, you're willing
to try things, whether it's surfing or Spanish or whatever

(10:22):
it is, you're willing to try things and be bad at it with the
perspective that you're going toget better at it and that it's
worth trying just for fun. And so the premise of the
midlife crisis is really that somehow you know that you're
going to, if you can survive it.All you have to look forward to
is disease between death. But the reality is that once you

(10:46):
get through the chrysalis, you have this butterfly era ahead
and EU curve of happiness shows this.
It shows that we as we get older, after a low point around
45 to 50, we are actually happier and have greater life
satisfaction. So it's interesting, you know,
you see people and again, we seeevery day here at MEA, people
show up and they say the word stuck and and then you dig in

(11:07):
and how long have they been stuck for?
Some people been stuck for. Potentially decades.
Decades. Yeah, right.
You've talked about transitionalintelligence TQ and you said
that allowed allows you to move through it faster.
What are some of the practices that accelerate that?
Well, I mean, if we look at eachof these three stages, to
ritualize something doesn't necessarily require other

(11:27):
people. You could ritualize something
and write a letter to yourself and, and say, OK, I've just lost
my job. What am I supposed to learn from
that experience? What am I supposed to let go and
to and, and to say, hey, that's the ending of that.
When I was selling my business, selling Juan of Eve, I wrote a

(11:48):
letter to myself, partly becauseI knew that I'd spent 24 years
running this business and I it mattered a lot to me at my
identity was very reliant upon it.
A letter to myself as a ritual to say thank you, Chip.
It was Chip's letter to Chip, but it's saying thank you for
this era of my life. And here's all the things, the
great things I got from it. And here's why it's time to to

(12:11):
say goodbye to that. And that letter, I still have
the letter. I mean, the letter helped me to
say I'm ready to move on. So that is that would be a step
for someone to take. And you know, the messy middle
is, is to find the through line.And it's actually like, OK, on
the other side of this, how am Igoing to be better?
And then the growth mindset is like being willing to like laugh

(12:33):
at ourselves. But you know, men experience
midlife crisis different than women.
And I want to talk about that for a moment because in my book
Learning Love Midlife, I didn't spend a lot of time on this
topic, but I've only learned a lot more about it in the last
two years. So the top five things that men
are challenged by and their lifeare the following.

(12:53):
Number one is loss of virility, like feeling viral.
So it's sort of hormonal in our,in our, in our late 30s, we
start dropping our testosterone by about 1% a year.
We start getting a little bit ofgut, the visceral fat, you know,
gut hangs on. We have less libido, we start to

(13:14):
have a little bit less energy. So that's one of the top things
that men notice and that actually sort of like, make them
feel stuck also because all those things sort of speak to
this idea that I no longer, you know, flourishing and healthy #2
is career and financial disappointment.
By the time you get to around age 50, you can sort of say
like, you know what? I thought I was going to, you

(13:35):
know, be CEO of the company or Iwas going to have $1,000,000 in
the bank. And, and so that's a big one for
men. A third one is growing
irrelevance, just feeling like, oh, as they get older.
And this is particularly tough for men who have never had to
deal with any kind of bias. So if you're a straight white
man in the United States, you know, by the time you get to 50
and early 50s, you're starting to see that maybe there's some

(13:59):
ageism in the world. And as a guy, as a guy, you've
not had to deal with sexism necessarily.
You know, there, some men would say there's exceptions.
We're living in a world in which, yes, there are.
There's sexism for men, for sure.
You're not, you're not having todeal with homophobia.
You're not having to deal with being a person of color.
So they're the first time in your life you're realizing, oh,

(14:19):
my God, I'm part of a demographic that actually people
make fun of, you know, I have less power.
And so that growing irrelevance is a big one for men #4 on the
list is feeling lonely and not knowing what to do about it.
Men. Yeah, yeah, The Big L word in
their, you know, around midlife is like, yes, you know,
especially if you're getting to a place where you're later in
your career, like who are my friends?

(14:41):
Who are my peeps? And then finally, lack of
purpose. So these are the things that a
lot of men start to feel, especially lack of purpose of,
you know, careers winding down or if you empty nester or
whatever it is. And by the way, men have a lot
less things going on in life than women.
Women have many more roles and identities and that's probably
because they're, they're actually better at at

(15:03):
multitasking. For women, the top five are
perimenopause. So it's also hormonal.
So both men and women have a hormonal issue, but they're, you
know, obviously different. Perimenopause and menopause #2
for women is the tyranny of conventional beauty.
So you get to 455055 years old, the things that you, the beauty.
For men it's brown and for womenit's beauty.

(15:25):
It's maybe harder to continue tohave the traditional sense of
beauty. And so that can be really
problematic. Which takes us to #3 on the
women, Celeste, which is you feel invisible, men feel
irrelevant, women feel invisible.
And when I say invisible, it's not.
It's sort of in basic culture, but it's also romantically the,
the, the romantic odds for, for heterosexual women are not very

(15:50):
good. 70% of the people over theage of 50 who are single are
women. And so that's another thing
that's going on #4 on the list is financial challenges.
So women, you know, because theymay not have earned as much,
they may have taken time off from work with to have kids.
If they're sick, they become single at that age.
They have more issues and more financial challenges.
And then finally, endless caregiving women in at that

(16:15):
sandwich generation time are providing, you know, care to
parents and kids more than men are.
I mean, on average again, some again, these are all averages.
So because of that, there's a sense like, Oh my God, where do
I have time for myself? And that's why the whole premise
of self-care really sort of arose out of that.
Do you think women navigate it better because they're just much

(16:37):
better at they they don't have the loneliness and and they're
far. More, I think that's one reason,
I think one reason women, that we sort of see midlife crisis as
a male thing as opposed to a female thing.
I think part of it is Hollywood.I think part of it is that women
have other people to talk to. I mean, you know, let's be
honest. I mean, midlife suicide for men

(16:58):
is about four and 1/2 times morethan for women.
So women partly have more ways to deal with their frustration
or their challenges of midlife with their friends.
I think that's part of it. I think also women for women,
because they have many roles that they're they're that

(17:20):
they're, you know, embodying when something goes away,
whether it's losing a job, losing a job for a man at 50
years old is more traumatic thanfor women, that there's data on
this. And it's partly because when a
woman loses a job at 50, it is not the only thing that defines
her. Whereas for the man, you know,
they're the breadwinner totally in the family.

(17:43):
And so that's part of their role.
And then they had better be bringing home the bread.
And so for for men, that becomesmore problematic.
Whereas for a woman, you know, it, it is hard, maybe harder for
a woman with empty nest than fora man.
If a woman has defined herself as the mother and as being the
person who's like hovering over the kids, and the kids are no

(18:04):
longer at home, but that same mother, that same woman may have
a bunch of other roles that theyhave inhabited that the men have
not. Yeah, it's, it's so true.
I mean identity and, you know, I'll look at myself, right?
Like if you took away my career right now, that would be such a
big piece of my identity. And that would be tough, yeah.

(18:27):
No, it's. It is.
And then as a man being like, Ohmy God, I'm not providing for my
family. Yeah.
It's hard, yeah. And you know, I lost 5 male
friends. It was 42 to 52 suicide and
three of the five of them took their lives primarily because in
the Great Recession, their career or in the cases of the
entrepreneurs, their businesses went down and they didn't know

(18:48):
who they are without the identity.
So if, if we're summarizing all this, I think midlife crisis is
a thing. It's, but it's not as big of a
thing as Hollywood would tell you it is.
And it's not a thing just for men.
It is a thing for women as well in terms of going through the
chrysalis. So the experiment I'd love to
have people think about or that thing that they can do as a

(19:09):
result of this is look at your own life right now and ask
yourself, how many transitions am I going through right now?
So maybe you're going through a career transition, maybe you're
going through a transition spiritually.
That's a transition that a lot of people don't notice because
it's a very invisible. Maybe you're going through a
transition in terms of hormonally.
So what kind of transitions are you going through and at which

(19:31):
stage are you at? Are you at the ending or the
messy metal or the beginning? And based upon that, what could
you do to ritualize it? If it's at the end, look for
social support and the through line of how you're going to get
through this and how it's going to be better on the other side.
And then what's the growth mindset you can have?
Because once you can sort of identify where you are, you can

(19:52):
say like, oh, there's a coping mechanism or a tool that can
help me to get to the edge at the other side of this.
Yeah, and, and you know, just toput a shameless plug in for mea
look if if you're feeling stuck.Yeah.
That's that's what this whole company was founded on, yeah.
Navigating transitions. I was stuck in my life.

(20:12):
Yes. I felt my I had a relationship
that was ending not by my choice.
I had a foster son who's AfricanAmerican who is wrongfully going
to prison, and I had to try to get him out.
My body was breaking down on me in certain ways, and I ended up
having an NDE to an allergic reaction to an antibiotic.
But I didn't also want to run mycompany anymore and I was
running out of cash. So I felt really stuck.

(20:34):
I felt, frankly like a loser. And that's what a lot of people
feel like in their midlife crisis is they feel like a loser
because they have a belief they're going to be stuck in
that chrysalis the rest of theirlife.
Number one is you're not a loser.
A lot of people are going through midlife chrysalis.
Being with a group of people whoare all going through
transitions at the same time is helpful.

(20:54):
Understanding that there are practices and tools that can
help you through it are great, is great.
And knowing that there's a butterfly on the other side of
this can help you to feel like OK.
My job is to learn and to just be patient and to take the
proper steps to get to the otherside of this.
Yeah, and, and I mean, we just know women are more open to to

(21:17):
doing this work. We see it at MEA.
But as a male and midlife, I would encourage men to to
explore this. They need it more.
They need it more. That's the funny part.
They need it more, but they're the most resistant to it because
we've been taught not to talk about our feelings.
Yeah. And that's why, you know, coming
as a couple sometimes is interesting and helpful thing,
sometimes it's not. You know, I mean, we most people

(21:40):
come on their own, but couples can find it to be very helpful
because frankly, it opens the the husband up and it's such
that they are more aware of what's going on and they have a
common language to discuss. Oh, wow.
You know, we're both going through something and and I just
came, I just show you the list of the five things that they're

(22:01):
going through, the five women's going through.
But for the women, they may not even think that their husband is
willing to listen to it. And for the man, they're not
even talking about it so. Any final thoughts on the
midlife chrysalis before we moveon?
No, I just think I hope that theterm midlife chrysalis, which is
the name of our podcast and the name of, you know, a core part

(22:23):
of what MEA is about, becomes part of the popular lexicon.
So we'll get it there. For all of you folks listening,
start talking about the midlife chrysalis.
Midlife and and transitional intelligence.
Transitional Intelligence. TQ very important.
Absolutely. All right, Chip, thank you very
much and for everybody listening.
If you. Like this episode?
Leave us a rating, leave us a review that fuels us to keep

(22:43):
making more of these episodes. And I think that's a wrap.
We'll see you in the next. Episode, yeah, and we've got,
gosh, next episode's this Friday, and then next week is
Christmas. So we'll be back, though.
We'll be back with Wisdom Wednesday, the day before
Christmas. Crazy.
We'll see you all soon. Thanks for listening to Wisdom
Wednesdays on the Midlife Chrysalis.
This show is produced by MidlifeMedia.

(23:05):
If you have a question you'd like us to explore in a future
episode, please send it to podcast@meawisdom.com.
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