December 1, 2025 • 46 mins
What happens when Don Lemon gets truly unfiltered?
In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older.
Don also reflects on the state of media, the “prime” controversy, and how stepping away from traditional news helped him reclaim his voice and his joy. If you’re ready for truth, evolution, and a warm reminder that life after 50 can get better, tune in. Watch now.
Timestamps:
00:00 Chip’s episode opening
00:57 Don on aging and happiness
02:34 Don’s childhood and early years
03:38 Politics, Reagan, and identity
06:52 Dating while closeted
09:52 College years and social life
12:17 First gay bar experiences
16:20 Don’s coming-out story
19:47 Coming out publically in a book
21:41 Midlife chrysalis and confidence
25:10 What gets better with age
28:28 The “prime” controversy explained
34:07 State of media and independence
36:30 Politics, division, and future outlook
37:26 Don on never retiring
38:49 Possible regret 10 years from now
40:24 Don’s wisdom bumper sticker
43:543 Judy Garland and music icons
46:50 Chip’s reflections
Learn more about MEA at https://www.meawisdom.com/
Keywords:
#DonLemon #midlife #agingwell #lifeafter50 #midlifefreedom #midliferenaissance #comingoutstory #lgbtqstories #authenticitymatters #selfacceptance #personaltransformation #midlifewisdom #findingyourvoice #reinventyourlife #unfilteredconversation
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
People wonder why I will put things out there when people
don't agree with me or if I havean argument and they think like,
oh, you didn't get the better side of that argument.
It's like, I don't care. It's what if That's what life is
about. We are all going, Oh my gosh,
this person destroys. This person did that.
We're in that kind of culture. I'm not there anymore.
I don't really care what you call me, and I don't really care
what you think about me. I care what I think about me.
And that experience taught me that.
(00:21):
So, yeah, it was a chrysalis. My entire life is a chrysalis.
Welcome to the Midlife Chrysalispodcast with Chip Conley.
Where we explore how. Midlife isn't a crisis, but a
chrysalis, a time of profound transformation that can lead to
the most meaningful chapter of your life.
(00:42):
Welcome to the midlife chrysalis.
I'm Chip Conley and whoa, today's episode is sizzling.
Sizzling is the way I describe it.
It's going to be a salacious interview with Don Lemon.
We've never met, but boy, does it seem like we've had 20 years
of history together based upon the conversation we you're going
(01:02):
to hear in just a moment. For those who don't know Don
well, you haven't been watching TV.
Very famous CNN journalist, newscaster who's gone, gone
rogue and independent and done very well in the process of
building his own brand. So I think you're going to like
this one. Just know that it it is pretty
(01:24):
unfiltered. And I hope, I hope you enjoy it.
Don Lemon, welcome to the midlife chrysalis.
It's an honor to have you here. Hi Chip Connelly.
Midlife. Midlife Chrysalis instead of
crisis. I like that.
Yeah, well, there's the part of the reason for that is because
EU curve of happiness research shows that after a low point
(01:45):
around 45 to 50, people get halfhappier after 50.
Has it been true for you? I guess, Yeah, yeah, yes, 100%.
I never, I'd never thought aboutit, you know, because I don't, I
don't really have a problem withaging.
I kind of like it. I like getting older.
Now I look at my body and I go, oh, I looked at this morning.
Dude, it looks pretty good. Thank you.
(02:07):
I know. But you know, I was leaning over
the the bathroom counter this morning just waiting because I
have a little steam shower waiting for the steam shower to
heat up. And I looked and I was that oh,
back in the day that would not have been there.
It would have been up here but me, you know, this and all that.
But yeah, I'm good. I actually don't feel, you know,
I'm, I'm a man of a certain age.I'll be in going into my 6th
(02:30):
century. I mean century, my 6th decade.
I'm 600 years old, right? I'm going into it by 6th decade
and I can't believe it. I look at myself and I'm like, I
don't feel it. And I don't think I think I look
younger than my parents. I feel the same way that I felt
when I was in my 30s. And so I really don't have an
issue with aging. I want to be healthy.
(02:51):
I'm not overly. I used to work out a ton and I
found out that I'm in better shape and I'm happier when I
just do everything in moderation.
And so I never really have. But yes, I am I happier.
Yeah, I am. Yeah, yeah.
You grew up with your mom and your grandma is your grandma.
Her name is Mary. Her name is Mary.
We called her Mommy. In Baton Rouge, LA.
(03:14):
Yes, well, it was in Port Allen,which is West Baton Rouge, Yeah.
OK, OK. Tell us about your upbringing,
because as I was reading up on you a little bit, I said like,
Oh my God, this dude and I have a lot in common.
You worked at McDonald's in highschool.
You were high school student body president.
Check. Check for me as well.
(03:34):
You were a Republican in college.
Wow, that I want to hear about that part.
I worked for Republican congressman in Washington DC
after my freshman year. I wasn't a Republican, but I
worked for Republican. You like Crocs, so we have a lot
in common. Tell it.
Tell us a little bit more about your upbringing and how the hell
(03:54):
you became a Republican in college.
I'd love to hear more about that.
Well. I don't know if you remember.
You grew up. Do you remember Alex P Keaton?
No. Which was Michael J Fox was Oh.
Oh, yes, of course. But so were you.
Were you sort of a Michael J Foxout?
I was. Talking with Michael J Fox,
Preppy Blue Jacket with gold buttons and white bucks and
(04:14):
khakis, that kind of thing. And I grew up in the South.
The South is very conservative and I, plus at first I didn't
like the Reagan's and then the longer he was in office, I began
to like him and, and then he didthe whole thing with the HIV and
AIDS and I didn't like him anymore.
However, I wrote him once told him that, you know, I really
liked him and that I was, I had registered as a Republican and
(04:36):
people thought I was nuts and blah, blah, blah, blah, blah.
And I got a letter back from theWhite House and my mom comes in
and she says, what's this? And I said, what do you mean
with this? She goes, this is a letter from
Ronald Reagan. And I said okay, and I opened it
up and whatever I have it somewhere in, in my memorabilia
thing. But I was young, I was naive and
I, you know, I thought it was cool and maybe I maybe I thought
(04:57):
it was kind of a counterculture thing to do back in the day to,
to, to have someone like me. And then once I became more
mature and learn it and I understood what was happening, I
quickly changed. I changed that.
But yes, I was. And I still have a bit of a
conservative streak. Yeah, like most people, you
know, I think most people have aconservative side and they have
(05:17):
a liberal side. And they're not so extreme as as
the media and and the politicians would lead people to
believe. And what part of you is
conservative would you say and socio political whatever?
I think I can be concerned. It's kind of weird.
It's, you know, as a gay man, I can be a bit conservative
sometimes socially, you know, sometimes I have conservative
(05:38):
thoughts and I go, well, I understand that.
I understand why they're saying that and I don't necessarily
disagree with it. And then people go on you crazy,
blah, blah, blah, blah, blah. And so, and I'm more on the
conservative side, except for lately conservatives have become
the party of cancel culture. I don't believe in cancel
culture and I believe in like ifyou if there's an issue that
someone gets in hot water for everyone's like can't talk about
(06:01):
it, whatever. I'm like, no, let's talk about
that. This is an opportunity to have
a, a constructive conversation about it rather than being quiet
about it. Like, you know, I, you know, I,
I would love to interview Marjorie Taylor Green.
She's mad at me. She won't do it.
And then sometimes some, some ofthe conservatives who say crazy
things, I would like to interview them.
(06:21):
Or sometimes some of the things that people get cancelled for, I
would like to interview them to have like a productive
conversation. Because many times through those
experiences, people will gain a point of view, right?
They'll have an epiphany or theywill change their minds through
that process. And if we keep ignoring it and
we keep cancelling people and not allowing them to go through
that process, I think that that is inhibiting.
(06:43):
And it's not, you know, it goes against what what we're supposed
to be about, what the world is about.
And that's evolution. We keep evolving, we keep going.
We it's bad, but it's about progression and not regression.
And so in college you had a girlfriend if I'm not mistaken.
I did. I had several.
I did too. The, the whole, it's in the
yard, the whole thing I did, I went there.
(07:05):
I'm not a I'm not a what do you call it?
What is it a goal? I'm not a gold gay or whatever
you call it. Gold gay What is a gold gay?
It's like a a gold and there's aplatinum or something when you
like some people said I haven't been with a woman or a lesbian
will say I haven't been with a man or never even seen the other
(07:27):
parts or whatever. Yeah.
Wow. OK, You're telling me things I
don't even know, but I So at at what point?
So you knew at a young age that you might be gay, but if I'm not
mistaken, and at some point along your maturity path, you
came out and what? We'll talk about that in a
(07:48):
couple minutes. But what was it like as a
closeted black gay man? Were you dating women?
Were you dating men? But not talking about it?
Where what was what was going on?
I mean, we want the, we want the, the DL on the DL that the
down low talk about from Don Lemon.
Well, I was doing what a lot of people do or did and what a lot
(08:12):
of Republicans do now. I was dating women, like in
public and then privately. I was, you know, secretly doing
things with guys. But, you know, because there was
a back then, there's a lot, there was a lot of shame around
it, especially in the Deep Southin the, you know, in the 70s and
80s. Yeah.
And so I had girlfriends. And the weird thing is this is a
(08:33):
weird, very strange thing. You don't know necessarily when
you're when when biology is going to catch up, right, When
the real thing is going to catchup because because of the
hormones and because I was so young, I had no problem being
intimate right with. And then I remember the first
(08:54):
time when I didn't, I became, you know, someone who was
actually of a certain age. And then I realized, like, I
don't really, I'm not really enjoying this.
And it was, it was a real wake up call for me because it was
someone who was a girlfriend andI was like, Oh my God, I'm gay.
If you're enjoying the conversations we've been having
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(09:15):
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(09:37):
opportunity to flourish. Claim your copy today at
meawisdom.com/midlife Book. That's, I mean, that's when I
really realized it and I remember.
What age were you at that point?Probably sometime around high
school, High school or early college.
I just remember being at home alone and we were messing around
(09:59):
and nothing was happening. And before it didn't matter.
Yeah, it it always happened. And then but I think also too,
maybe it was her. Maybe I wasn't attracted to her,
you know, that's that really sort of crystallized the moment
for me. So you from a young age, you, I
think you like you were a fan ofMax Robinson and you, you would
(10:23):
actually videotape the news so you could actually watch it.
And, and so you know, at a youngage that you're interested in
the media and maybe even specifically being a, a
journalist and newscaster. And that must have been hard to
know a as you were moving into your adulthood, that this is the
career you want to be in and it's really hard to be out.
(10:45):
So how what was going on for youpsychologically during your 20s,
thirties and up to the point when you wrote your Seminole
book Transparent, which came outaround age 45?
Well, that, yeah, that was a long time, you know.
Yeah, it was a long time. That was a long time.
So in college at at LSU, I knew what was up by the time I got to
(11:06):
college and I would hang out with my friends.
I would date girls. I would go to the bars with
them, all of the dude bars and all of the frat guys and we
would go and then right down thestreet.
Were you in a fraternity, Don? No, I was, I was not in a
fraternity, but my friends were in fraternities.
You know, I went to LSU, which was not, which was not an HBCU.
And so it was, you know, majority white college.
(11:28):
And so frat life there was really big and sorority life
really big. You go to this fraternity row
and sorority road, and I was senior class president and I got
all these letters from the fraternities saying come join,
come rush or whatever. And then when I got there,
they're like, oh, you're black. This was LSU in the 80s.
Yeah. And so it was not happening for
me. So I was like, you know what?
(11:49):
I don't want to be a part of this shit where this white
fraternity or black fraternity is bullshit.
And so I didn't, but I would go out.
We would go to this place calledthe Bingle because it was LSU
Tigers and we would hang out of the bingo and then everybody
would get smashed. And then I would ultimately
sneak off and go to the alternative club, which was like
2 blocks away and I would sneak around and run and go into the
alternative club. And that was sort of mixed.
(12:09):
It was just like these sort of unusual punk rockers or you
know, counterculture kind of folks.
And then across the street was the gay bar.
I think it was called Neiman's then and every.
Like Neiman Marcus. Yeah, like the first time I
went, I snuck across and I went to Neiman's and my whole world
was like. Oh, this is so wait, wait, wait.
(12:30):
We got, I can't believe we're having this conversation.
So what my first time coming outwas at age 22, I was working in
New York for Morgan Stanley for the summer.
I was between my first and second year of Business School.
I was living at 86th and Riverside and I, and it was 4th
of July and 1983, so serious agecrisis.
And I walked from 86th to Riverside, all the way down to
(12:52):
Uncle Charlie's, a place in the village.
My gosh, I have an Uncle Charlie's story.
Oh, OK, we're going to go there.I say, who knew?
OK, thank you. This is this is fun.
Charlie's. No, we never.
Well, I wish we had because I would have dated you, dude.
I mean, you're you're hot. So I went into Uncle Charlie's.
First time I'd ever been in a gay bar.
(13:14):
Only had dated women previous tothat.
Was dating a woman during that summer.
And I walked in and it was like the Wizard of Oz.
It was like, you know, when the,the, the house came down and all
of a sudden Technicolor, you know, in Munchkin Land.
And I, I met a guy, you know, a Puerto Rican guy named Victor.
That's that night. And we spent the summer
(13:36):
together. And so that was my experience of
my first gay bar and and then myfirst boyfriend for the summer.
Isn't that amazing? Isn't New York City amazing that
way? Because I had I had a very
similar experience. So I would house sit for my aunt
in early high school, early college, but it wasn't until it
was all around the same time 838485 in there.
(13:59):
So I would go to the names and that was eye opening.
But then when I would go to New York and house sit for my aunt
in the summer, they take these great vacations.
They go to Egypt for like 4 weeks and whatever.
And so I would, I would house sit for their They had this
townhouse in Harlem on Convent St. in Sugar Hill.
And I had that entire like four or five, six story house to
myself. And so I would.
I had one night I sneaked downtown and I went to Uncle
(14:22):
Charlie's, right? And is that your first?
That was your first gay bar in New York.
Those are my first gay bar outside of yeah, outside of Ian
and Nieman's One Night and My Mind being.
You're underage, you're underage.
You're doing that. No Jaws only.
I was not underage. I was 18 years old. 18 was a
drinking age in Louisiana. Oh, but in New York, though?
(14:45):
Oh, I don't know. I don't know.
I never even thought about it. Was I that we're not going to no
one, you know, statue anyways. I got in, I got in.
So, you know, it could 8/19/22 and it could be like I said, 85
or that would make me 2020 sort of on the edge.
That was probably why I didn't go in high school because I was
too young. I think maybe it was just like
around, you know, I was 21 and so I went and I was so nervous.
(15:10):
And this was during the time of,you know, the big buff body,
everybody, the big buff shaped body and you know, big blonde or
whatever. Everyone looked like a like AGI
Joe and I didn't look like AGI Joe.
This is like, I didn't think I was hot.
I was skinny and I look back on pictures and I'm like, damn,
you're a hot. You were a twink and you didn't
know it. So I met this guy and that was
(15:35):
like my first real experience. I met this guy and we went home
and is a white guy, discovered alot of things about myself and I
don't know, I've never seen him again.
But it was also kind of frightening because it was
during the aids, whatever. So we were very careful.
Luckily, you know, I'm alive and, you know, in good health,
(15:56):
and I'm so happy that we have the drugs now to do to take care
of of folks who are positive. But anyways, I digress.
Yeah, that was my experience around then and it was I
couldn't wait to move to New York.
Yeah, me too. I loved, I loved New York.
So you had been 20 years, more than more than 20 years of
living this life. And then what was it that that
(16:19):
led you to writing this memoir, this coming of age coming out,
coming out story in your mid 40s?
And were you going through a bitof a midlife chrysalis, meaning
the idea that you something was shifting in you and instead of
it being a crisis, it was a doorway and maybe to a whole new
life. And are you happy you walked
(16:39):
through that doorway? Well, as you know, like,
especially if you are our age, right, there's a, there's a,
there was a dual life that you had.
So finally, when I left, I, you know, I would hide the gay part
from my friends and I kind of lost touch with my college
friends and then I moved to New York and then I then I reunited
(17:01):
with them and you know, that's awhole nother thing.
But I finally moved to, I realized that I had to in order
to be who I was, who I, who I should be and to achieve or
accomplish the things that I wanted to accomplish that I
would have to leave Louisiana. And especially after my journal
professor told me that I'd nevermake it as a journalist.
And I said, oh, OK, So I left, Ileft LSUI, left Louisiana and I
(17:23):
moved to New York. While I was in New York, I was
out amongst friends and some Co workers, but not to everyone.
I didn't tell my family, I didn't tell the people who are
closest to me. And eventually a college friend
called and said, Hey, Don. And, you know, I was living in
New York. He was in Louisiana, or I think
still in Louisiana. He said, I hear that you might
be gay. And I don't care.
(17:43):
And that's how I reunited with my college friends.
And then I eventually have founda boyfriend that I'd been dating
for a couple years. And we broke up, and I was
heartbroken. And my mom was kind of my best
friend. I would talk to her every day,
even though we didn't live in the same city or state.
And I told her and I said, she said, what's wrong with you?
You just don't sound the same. And I said I'm just not happy.
(18:04):
And she said why? And I said because of my
relationship. And she said with who?
And I said John and she goes what kind of relationship?
And I said he was my lover. And I started crying.
And then so I came out to my momand then she said, well, I
won't. I said don't tell dad, don't
tell anybody. And 20 minutes later I get a
call. I Don it's dad.
I'm like oh fuck. And she told them and she told
(18:30):
my sisters and whatever. And then I was like, OK, I'm
out. It was weird because she was
very much in, in control. And then she kind of fell apart
lately. I mean, later, you know, it's
just like, oh, you know, I wanted grandkids.
And she went through that whole thing.
And then now she'd be like AP flag mom because she is all in.
She's like, talks to my husband.I love you guys.
(18:51):
All kinds of things. You know, she sends presents to
the dogs and. Yeah, so she's all in and she's,
you know, people. People can change and they do
evolve. So that's what happened.
And so by the time I wrote that book, I was out to my family,
but I wasn't out publicly, you know what I mean?
People at work knew for the mostpart.
(19:11):
If you were friends with me, I didn't really talk about it at
work, but people knew. And then someone asked me to
write a book, a publishing company.
And I said, OK. And I said, you know, what is
about? It says we want to know you're,
you know, you're a man in mainstream media and you're a
black man and not not many people get to this level.
And we want to know what it's like.
So I started writing about it. And then I got to the point
(19:32):
about when I left Louisiana and I was like, God, how do I write
this? And I said, I just have to write
it. I said, I cannot.
I have to have the same standardfor me that I have for everybody
else. I have to be honest.
And I'm not going to lie in thisbook.
And so they, the publisher said write it.
The editor said, just write it. We don't have to use it.
And I wrote it. It came time to there's like,
(19:53):
OK, we're going to go to print. Do you want this in there?
And I said, you know what, fuck it, put it in there.
But I thought I was going to lose my livelihood.
I thought people weren't going to want to watch me.
I thought I would get fired. And the exact opposite happened.
I'm sure there that look, there was some people I'm sure who
would you know that had negativereaction to it, but.
It was overwhelmingly positive and it gave me a sense of
(20:14):
autonomy that I didn't have before.
And the freedom, I mean, it was just, I said weight was lifted.
Yeah. So this was.
Nobody who's been to Christ, nobody was.
Nobody's out. Nobody was me.
And then Rachel Maddow was out, I think.
But Rachel wasn't. She wasn't Rachel like she is
now, right? Yeah, yeah, yeah.
(20:36):
She sent me flowers and yeah, I think that was.
Did what changed inside you? How did you evolve this
chrysalis moment where you started?
Maybe you were actually emergingfrom from the chrysalis and the
butterfly is there. Like what?
How did you know it affected your midlife?
(20:56):
Because you were right there in your mid 40s when all this
happened. Like I said, it gave me a sense
of autonomy. But also it was very similar to
when I told my mom, if I told mymom that I was gay and she was
OK with it, then nothing else mattered.
And when I wrote the book and I started reading the book to my,
I would read the galleys to my mom and we would sit and read
(21:16):
and she's like, and I would say,mom, can I tell about your
affair and that I'm the product of an affair?
And she goes, yeah, tell it all.Tell it all.
She goes, I have nothing to be ashamed of.
You have nothing to be ashamed of, ashamed of.
And so once my mom said that that's that was the real reason
where I said printed F it. But still I thought, you know,
I'll just have to go do something else in life.
If if I can't, you know, continue with this career.
(21:39):
It, it gave me a sense of freedom and that I had never
experienced before and the confidence that I had never
experienced before. You know, I used to think then
before then I used to think thatI didn't care what people said
about me. But there are levels to that
because then I really didn't care about what people have to
say. I don't care about other
people's criticism. But it's also from having that
(22:02):
those types of moments ship or having, you know, that moment or
those types of moments in your life.
People wonder why I you know, I will put things out there when
people don't agree with me or ifI have an argument and they
think like, Oh, you didn't get the better side of that
argument. It's like, I don't care.
It's what if that's what life isabout, like you.
And and so we are all, you know,going, Oh my gosh, this person
(22:23):
destroys this person. This person did that.
We're in that kind of culture. This person is a jerk.
And we're I'm not there anymore.I don't really care what you
call me and I don't really care what you think about me.
I care what I think about me. And that that experience taught
me that. So yeah, it was a chrysalis that
I live with my entire life is a chrysalis.
Yeah, so I read a book. Ongoing case now.
(22:43):
Yeah, I wrote a book called Learning to Love Midlife, 12
Reasons, Reasons Why Life Gets better with Age.
And what I'm hearing is one of the reasons life gets better
with age is, you know, have no more FS left to give.
You don't get more. There's an element of like, you
know what? I'm just going to be who I am.
I care about things, I care about people, but I'm going to
be less possessed by being a people pleaser.
(23:06):
And I think women in particular,but I think gay men actually go
through this in as well in termsof we've tried, we've tried to
do what we can to be the best little boy in the world.
We've we've done what we can to actually fit in and you in for
in your case, you have that the,the double fitting in of being
a, a black person as well as being gay.
(23:27):
And there's an element of like, wow, you just, this is who I am.
Yeah. What?
It's not just for you people pleaser.
It's also being an overachiever.A lot of gay men I know are
overachievers. You got us, you know, you got to
be the best at everything. So it could because it's an
armor that you build up. And yeah, I've been a people
pleaser, but not not anymore. Every once in a while I feel it
(23:48):
like creeping and they go why doI care?
Yeah, So what else has gotten better with age for you?
Sex. OK, tell us more.
Dude, you're going there. I love this.
I, you know, so for everybody toknow, Don and I have never met
before. We've just commuted by e-mail
and text. So the fact that Don's going
(24:10):
there on this call with me is very much appreciated because
again, why not? What kind of path are you
carving through midlife? Our free Midlife Pathfinder Quiz
helps you discover which of eight archetypes best describe
your approach to the stage of life and what that means for
your next. It only takes a few minutes, and
(24:32):
your results may surprise you. Find out your archetype now.
It's quick, it's fun, and it might help you see your journey
in a whole new light. Take the Pathfinder quiz at
meawisdom.com/quiz. Well, I mean sex because you
know who you are and you know what you like and you know what
to do and, you know, it's like sex with a novice is not really
(24:56):
that much fun. I mean, you know, it sort of
wears off, right? So yeah, the sex is good and it.
And it's not just about getting to the end.
It's about all of it. It's about the beginning, the
middle and the end. You know, I don't care like
anymore. It's like, Oh my God, if it when
I take my shirt off, is this person going to think I have a
good body or not? I don't fucking care.
(25:17):
I don't care. You know, this is to have a good
time. But I'm also married now, so it
doesn't really matter. I'm off the market.
But so and then also what's gotten better, confidence has
gotten better. I actually think that I get
better looking with age. I think you do.
This black don't crack girl. I mean, you like you look really
good. Thank you.
You know, I looked at you know who Steve Scalise is, right?
(25:39):
Yes. Steve Scalise and I went to the
same college. He was in the same fraternity as
my friend and. From Louisiana Republican
congressman from Louisiana. With the same age, he was born
in October of 65. I was born in in March of 66.
I look at Steve Scalise and I say, you know, I it just gives
me, I'm like, I don't look like that.
(26:01):
And I know, but I think I would look if they're one.
Of I don't think he's going to give you an go, let you
interview him again after sayingthis.
Or whatever I did, they hate, they don't want to interview
with me anyways because you know, you're afraid of the
truth. I feel I don't look like that.
And so I'm like, I don't feel that age.
And I think that's a lot. I think that has a lot to do
with it that I don't have. I don't have secrets Chip.
(26:24):
I don't have any sort of weight on my shoulder.
And I think that that is very helpful.
I'm very open minded. I'm very I allow people to be be
who they are. I accept things for what they
are. And I think that has a lot to do
with remaining remaining youthful even as you are aging.
I love getting older. I don't want to reach a point
where I want to be a mobile. I want to be mobile and I want
(26:47):
to have my wits about me. Other than that, the alternative
is not to be here and I would prefer to be here and living the
best life I can at whatever age I might be.
I would not want to go back to my 20s, no or no, and let if I
knew what I knew now, perhaps I wouldn't want to go back to that
time. So let's talk about something
you said a couple of years ago. But, well, it was during the
(27:09):
2020 election. It was about Nikki Haley being
passed her prime 2020. Was it 2024 or 2024?
Yeah, it was 2024 because, yes, of course.
So that was not long ago actually.
It was in 2023 that it happened.Yeah, 2023.
So if you could take that back, would you take it back?
What let's, let's, let's set this up because what you said
(27:31):
and again, this is the only timeI'm going to ask it.
You can ask me anything. I'm glad you're asking me this
question, but. And and so the question was you,
you said that maybe she was pasther prime and she was, you know,
that and something about, you know, women maybe in their 40s,
we're past, might be past their prime.
(27:52):
And it sort of blew up. You got a lot of shit for it.
And I want you to just sort of maybe unpack that a little bit
because this, this, this podcastis really about aging and about,
you know, not men, women and everybody in between.
So how do you feel about that now?
Well, I wish I, I wish I could have been clearer and people
could have understood and I wishthe company that I work for
would not, would have stood behind me rather than making it
(28:15):
an opportunity or predicate to, you know, to try to marginalized
me in a certain way, right, to, to try to restrict me.
But if you go back and look at that clip and, and it's besides
the headline, if you really go back and look at it, what I said
is I don't believe that. So my point was, is that society
believes that and Nikki Haley should know better considering
the way society treats women. And that was the point of it.
(28:38):
And so she's saying that Joe Biden is too old.
She's being an ageist, but society is also thinks that
she's old at a woman who is 51 years old.
That's what society teaches us. I said, I don't necessarily
necessarily believe that don't shoot the messenger and the
messenger got shot. That's, that's all that I meant.
I don't, I don't think women arepast their prime at any age.
Or you can do what you want. I think for me personally, I'm a
(29:02):
very logical, rational person. So and at someone who is of a
certain age, I am past my prime.It's OK for me to say, to know
that it's OK for us to be able to say that because some people
feel like, Oh my gosh, you know,how can you say that?
And I'm so hurt by it. No, I can't run.
What does? That mean though, darling?
It means for me, what it means is that when I think about it,
(29:24):
when I was in my 20s and 30s, I could run 10 miles and not be
out of breath. That is fact.
When I was in my twenties, 30s and 40s, I was sharper.
Now I have to recall things and so physically and mentally,
there is a time where we are firing on every single cylinder.
And as we get older that goes away.
(29:45):
And that's OK though. And so I was saying that about
me. I'm not saying that you may feel
differently it it could be you at 708090.
And basically that's what Nikki Haley was saying about Joe Biden
is that he was too old, that he was past his prime.
That's what she was saying. And so when someone says that
about her, she gets upset and then she fundraises off of it.
(30:06):
So that's all I'm saying. But it's OK for me.
I'm a different person. If some people maybe that hurts,
but there's we have to be realistic about what happens to
us. Now, I do think that I get
better looking as I get older, but you know, I'm a different
person now. I'm not the same person that I
was in my 20s, thirties or even 40s.
And soon I won't be the same person I am in my 50s.
(30:26):
So it is true that, you know, mental acuity and being able to
be fast and focused does actually decline with age, but
wisdom actually can grow with age.
And this idea of crystallized intelligence, you're able to
connect the dots. I mean, do you think that
people, women do the women are held to a different standard
than men when it comes to 8? Percent at a different standard,
(30:47):
and it's unfair, an unfair standard.
About that. Because because when and again,
my point, men can have kids at any age and it's always that, Oh
my gosh, men age like fine wine and then they don't say the same
thing about women and my. Silver foxes, Yeah, the silver
fox and not a silver vixen like a silver.
(31:08):
And so that's. Right.
That was my point. Like, don't you know that, like
Nikki Haley, why are you doing that?
Why are you pointing out something about somebody else
that people have been saying theway, you know, for centuries
here in the world, that a woman has to be a certain age when
she's in her prime? That's it.
That's all I was saying. So I'm glad you gave me the
opportunity to talk about that. But I it wasn't to any point
(31:29):
where I was saying that's what Ibelieve.
Yeah, and, and there's lots of different forms of prime.
So there's, you know, prime. You know what, especially there
are a lot of amazing female politicians, Nancy Pelosi being
one of them. Who had Nancy Pelosi prime was
certainly in her 70s and early 80s.
Nancy Pelosi may still be in herprime.
(31:51):
Did you see how she handled thatreporter the other day that
asked her? Yeah, yeah, yeah.
Thank you. Thank you for unpacking that.
Nancy Pelosi, she has a bad ass.So let's talk for a minute.
We've talked an awful lot about other things, but the state of
the world, the state of media, the state of you going
independent and building the DonLemon brand, which is blowing up
(32:12):
in all kinds of wonderful ways. If you could prognosticate to
where we are say five years fromnow in 20-30 in terms of media,
in terms of politics, in terms of society, where do you think
we're going to be? Is is are we at the trend line
has been seemingly pretty bad, but do you have some hope?
I do have hope. You mean where are we going to
be just in general in the world or in the whole media landscape?
(32:35):
The. Media landscape but the let's
just let's focus on the US, let's say in the US.
Do you have how what's your what's your feeling five years
from now in terms of the nature of media, but also the nature of
the socio political world and you know how divided we
currently are? Well, I think successful part of
media and the people who are in media will be somewhere between
(32:55):
independent journalism or something that is free of
corporate influence. And you can see that happening
now because there's just too much of it and people are sick
of it and they can tell when people are pulling their punches
and and on and on and on. So I think that's what then.
People are narrow casting now and they want to get information
from people they trust and they like and they don't know
necessarily they trust what they're seeing in the mainstream
(33:17):
media right now. And so that's good for folks who
are like me, the whole socio yousaid socio economic and
political and political. Well, I will tell you about the
world is about evolving. It's about evolution.
It's about recreating and procreating and whatever and
otherwise then we die. So if anybody thinks that we're
going to go backwards and anything is sadly mistaken.
(33:39):
The world will continue to evolve and we will.
The truth will come out and people will start to figure out
like, you know, that they're being bamboozled by this current
administration as they are finding out now.
I do believe right now that thiswhole thing that's happening
with Epstein and, and, and otherthings that the spell is being
broken for the, the sort of cultpower that Donald Trump has over
(34:01):
in the MAGA movement has over people.
So how what do I see in the future?
Like physics, the pendulum swings one way and then it
swings the other. And just as hard as it swings
that way, it's going to swing back the other way until it
eventually corrects itself. So I think by 2028, we're going
to have a Democratic president and a Democratic president is
going to get in there. And it's going to have to fix
the Supreme Court, whether that's expanding the court or
(34:23):
whatever. And so if Republicans get mad at
it, so be it. They're going to have to because
look at what happened. And so I think we're going to,
we'll, we'll be in a state of correction for the next decade
or two. And then, you know, we'll get
back to normal because this is certainly, you know, a sort of
upset the apple cart. This was like a meteor that hit
us. And we've got to, you know,
we've got to pull ourselves together from it.
(34:44):
So I think that's where we'll beat least in the next 1020 years.
Will you ever retire? No.
No, OK. No, especially now.
I mean, why do I have to? Why?
Seriously, why do I have to retire, Right, Boomer?
I mean, I'm in my home studio, my dog is here.
I'm earning a living. I get to hang out with them.
I get to speak to the people I want to speak to.
(35:05):
I if I don't want to do something I don't have to, and I
love what I'm doing, why would Iever retire?
I'm still in my prime ship. You are, you are.
So yeah, it's very interesting our relationship with retirement
these days. You know, when when people were
doing back breaking, mind numbing labor, getting to 60 was
(35:28):
like, oh, thank God, finish line.
I can now go live in Sun City and, you know, play golf and
have martinis at lunch and play bingo at night.
But we have, Yeah, exactly. We have completely shifted this
narrative. And you're a Gen.
Xer, you're an older Gen. Xer.
I'm a younger boomer. And our, our generations don't
(35:49):
want to do that. We, we often want to try
something new around age 60. If I want to ask you 2 last
questions, 10 years from now, what might you regret if you
didn't learn it or do it now? I might well, I might have, I
can say what I might have regretted if I had stayed in
traditional media. I would have regretted staying
(36:11):
in so long because now I have this freedom to do, which is
kind of a weird sort of it's notretirement, but you get the
benefits of being retired because you don't have to go
into an office and you get to set your own path.
So I might have regretted that. There's you know, I always said
I have no regrets and I really don't.
If there is one thing I wish I would have done, I guess that's
the regret, right? I wish that during COVID, I
(36:33):
would have taken the opportunityto travel more and do my show
because I had the opportunity was offered, I could have moved
anywhere in the world or whatever, as long as there was a
good connection, connectivity and I could have done the show
because lots of the shows were done from, you know, my, my home
studio. So I could have been at a home
(36:53):
in Florida or a home in California or a home in Hawaii,
right? And I wish that I would have
taken that opportunity to do that, but I unfortunately I
didn't, but. That's it, we learn our lessons.
And may have. And also, excuse me, maybe kids,
maybe one. Yeah, having kids.
Yeah, I'm lucky enough to have a13 and 10 year old with a
lesbian couple. Nice SO.
(37:16):
Congratulations. Okay, last question.
So let's say someone younger than you, they could be in the
media or they could be a black gay person from Louisiana, or
they could be just a friend of afriend.
They come to you and say, hey, Don, I'd love to have tea with
and coffee with you next week. And I'd love for you to come to
our time together with a bumper sticker, a Wisdom bumper
(37:37):
sticker. Not a not a figure, not a
literal one, but more like a figurative 1A wisdom bumper
sticker. Something that you have learned
maybe the hard way because our painful life lessons are often
the raw material for our future wisdom.
What's the bumper sticker that defines Don Lemon's wisdom and
what's the origin story for it? OK, this is so weird because
(37:59):
when you reconnected Chip, I said to you, what did I say to
you? Well.
We talked a few different times.You know, when I dialed in, what
did I say? Can you see me?
Yeah, you take your shirt. You were taking your shirt off
because you were going to changeyour shirt.
Okay, so are you going to take your shirt off in front of the
camera now? So the shirt that I was wearing
has the. Okay, yeah, I didn't see this
(38:21):
shirt. The shirt that I was wearing has
the exact thing on that you wereasking me about, and that I
will. And it sums up the conversation,
how I feel about everything whenyou talk about prime and all of
that and how I respect people ofevery age.
But I'm realistic about myself and I don't have the same.
I don't believe that everyone has the same standard that I
(38:42):
have. And so people might think that
their prime is whatever age theywant to think.
So I've explained that this is how I feel about aging, this is
my saying, and this is my show logo.
Old people be known. And then it has a Don Lemon logo
there. Old people be.
(39:03):
We know shit. So that's wisdom.
We know. We get our Spidey senses are
sharper. We know and so all of this, if I
could say bullshit that's going on, we see through the bullshit.
I can tell when somebody's bullshitting to me.
I can tell when someone's a goodperson.
I can tell whatever I can see around corners as a man of a
certain age because I'm old and old people be knowing.
(39:24):
That is what I would tell. So enjoy your youth.
Enjoy your youth. You can do all those things.
You can run 10 miles without dying, right?
But however, and some people cando it, I mean, people run
marathons in their 90s, right? You know, enjoy your youth, but
there's something that you can only learn from remaining on
this planet, surviving, and thatis wisdom.
(39:45):
And so that will come one day. And so no matter what happens
when you're young, there's always something to look forward
to and you have wisdom to look forward to.
And so just put yourself in a position where you can get to
that point in your life where you're like me and the devil may
care and you have 0 FS to live because old people be knowing.
Yeah, old people be knowing thatthat that is going to I, I I
(40:07):
want to get one of those shirts one of these days you and I are
going to get. Go to donlemon.com and click on
merch and you 2 can have. OK, there we go.
There you go guys. donlemon.com,The merch is right there.
Someday you and I are going to watch All About Eve together.
I know you love that film. I do.
Every line. Do you know it?
I mean, I don't know every line.No me you do.
(40:27):
Although every single line. Wow, the fact that you know that
movie as well as you do and you love Judy Garland, dude, you're
a gay man. I can tell you I'd.
Be gay. I love Judy Garland.
I think Judy Garland is one of the best singers and performers
ever. And you know the weird thing
people talk about, You know, voices like, well, you know,
Whitney Houston's incredible voice.
(40:49):
Barbra Streisand has an incredible voice.
Aretha Franklin and all that. But it's also in how they did, I
think the most perfect voice that that ever was Whitney
Houston. But Judy Garland, you feel her
life coming through that microphone, right?
And you see it. It's just, I remember when I
discovered Judy Garland beyond the Wizard of Oz, and that was
(41:11):
how hard were you? Oh, I was, God, I think I was
in. I was either late, late high
school, early college. I think it was early college.
You know, Judy Garland live at Carnegie Hall.
And I think I bought ACD player and I went to the CD store and
they had the unedited version ofthat.
I put it in the CD player and I've never taken it out Now, I
(41:32):
mean, and now I, I stream it. But yeah, when you're smiling,
when you're smiling, the whole world smiles with you when
you're laughing. And it starts with that.
When you're laughing, the sun comes shining through.
Yeah. So that was my Judy Garland is
amazing. I think she's fantastic.
I having just heard you, I wouldsay the one regret you may have
(41:55):
if you don't do it in the next 10 years is you're supposed to
be a Broadway performer. There you.
Go. I I can feel it.
I can feel it. I would love to Broadway.
Don Lemon, thank you for joiningus.
Done. Chip Connelly.
We're done. I, I hope that wasn't painful.
That was like. For months we've been and I
(42:16):
look, I, my schedule was crazy and you know, I had to
reschedule a couple of times. I apologize for that, but that's
it. That's after all of that.
All of that. Listen, dude, people are going
to love this. Your love, the unfiltered Don
Lemon, the truth teller and the human, just the beautiful human
specimen that you are. You are a moral beauty.
I said that to Maria Shriver. I will say that to you.
(42:37):
You are a moral beauty. Oh, thank you, Chip Connelly.
I hope to get to meet you in person.
You're out West, right? I'm in Santa Fe right now.
I'm, you know, I'm in Santa Fe, Baja, San Francisco, Austin.
I get, I get around. So yeah, I want to talk to you
about. We'll talk offline.
I want to talk to you about. We're let's talk about Austin
and we'll I'll come, I'll come visit you in New York.
(42:58):
All right, Thank you. OK.
I did not expect that. I did not expect that that
episode to go as personal as it went.
And you know, I will admit a long time ago when I was
watching no, that long ago, maybe 10 years ago, I was
single. I Don was single.
(43:20):
He had come out and I was like, you know what, he could be
boyfriend material. So I do believe and I, you know,
he's, he and I probably were separated at birth because we
have so much in common. So my first lesson is he used
the word evolution 2 times, maybe even 3.
And I think that was interestingbecause this is, you know, not
(43:40):
something I would have expected him to, to, to use because it's
very much of a personal growth kind of word.
Things evolve, people evolve. And so I think one of the
beauties of if you look at Don and from his, you know, humble
upbringing in, you know, Baton Rouge, LA, being a Republican in
college, learning over time thathe had to be closeted.
(44:03):
He's evolved. And one of the things that's
very clear about him today is there's that he even said it,
his confidence, but it's just his sense of who he is.
You know what the the beauty of just showing up and being who
you are and whether people like it or not, you just do that.
And I, I feel very similarly in my own life that I can do that
and hopefully you can too. Second lesson is no more FS left
(44:25):
to give. No more fucks left to give.
It is one of the 12 reasons why life gets better with age in my
book, Learning to love midlife. And I think, you know, that's
where Don is right now. I think it was in many ways, it
was that experience with Elon Musk.
You know, he was going to be doing things with X and it was
the experience of the thing I brought up to him, the Nikki
(44:46):
Haley comment about being in notbeing in her prime, that had him
get to a place where he said, like, I I don't need to deal
with all the politics of, you know, of traditional media.
And he's. Yeah.
I think one of the things that people appreciate about Don and
sometimes some people don't appreciate about him is he just
sort of says it like it is. You know, again, I think that's
(45:07):
something that that is true of us as we get older.
We have unvarnished insight. And that brings me to the third,
third thing. Now, I thought he was going to
take his shirt off and put the other one on.
And that would have been interesting.
And we would have gotten more YouTube use as a result of that.
But no, he he just brought over what he had taken off before we
started recording, which was this T-shirt that says old
people be known. The idea of wisdom.
(45:28):
His wisdom bumper sticker is really about wisdom, is about
the fact that as we get older, ideally we get wiser.
Hopefully the world is better off for that.
Many of you know, my wisdom definition is a metabolized
experience mindfully shared for the common good.
And for the common good is such an important part of that.
Wisdom is a common good. It is meant to be shared and
(45:49):
it's meant to make all of us better.
So I hope that you found a little nugget of wisdom, a micro
dose of wisdom in this episode. We'll see you on Wednesday for
Wisdom Wednesdays, where I have a conversation with Derek Gale,
the CEO of MEA. It's a short run.
So I, I, the beauty of the, the wisdom Wednesdays is they're
short. And so you can listen to them
very quickly. And hopefully we're delivering a
(46:10):
little bit of wisdom to you. Wishing you all the best.
See you on Wednesday. Thanks for listening to The
Midlife Chrysalis. This show is produced by Midlife
Media. If you enjoyed this episode,
help us spread the word by subscribing and leaving a review
on your favorite platform.
People wonder why I will put things out there when people
don't agree with me or if I havean argument and they think like,
oh, you didn't get the better side of that argument.
It's like, I don't care. It's what if That's what life is
about. We are all going, Oh my gosh,
this person destroys. This person did that.
We're in that kind of culture. I'm not there anymore.
I don't really care what you call me, and I don't really care
what you think about me. I care what I think about me.
And that experience taught me that.
(00:21):
So, yeah, it was a chrysalis. My entire life is a chrysalis.
Welcome to the Midlife Chrysalispodcast with Chip Conley.
Where we explore how. Midlife isn't a crisis, but a
chrysalis, a time of profound transformation that can lead to
the most meaningful chapter of your life.
(00:42):
Welcome to the midlife chrysalis.
I'm Chip Conley and whoa, today's episode is sizzling.
Sizzling is the way I describe it.
It's going to be a salacious interview with Don Lemon.
We've never met, but boy, does it seem like we've had 20 years
of history together based upon the conversation we you're going
(01:02):
to hear in just a moment. For those who don't know Don
well, you haven't been watching TV.
Very famous CNN journalist, newscaster who's gone, gone
rogue and independent and done very well in the process of
building his own brand. So I think you're going to like
this one. Just know that it it is pretty
(01:24):
unfiltered. And I hope, I hope you enjoy it.
Don Lemon, welcome to the midlife chrysalis.
It's an honor to have you here. Hi Chip Connelly.
Midlife. Midlife Chrysalis instead of
crisis. I like that.
Yeah, well, there's the part of the reason for that is because
EU curve of happiness research shows that after a low point
(01:45):
around 45 to 50, people get halfhappier after 50.
Has it been true for you? I guess, Yeah, yeah, yes, 100%.
I never, I'd never thought aboutit, you know, because I don't, I
don't really have a problem withaging.
I kind of like it. I like getting older.
Now I look at my body and I go, oh, I looked at this morning.
Dude, it looks pretty good. Thank you.
(02:07):
I know. But you know, I was leaning over
the the bathroom counter this morning just waiting because I
have a little steam shower waiting for the steam shower to
heat up. And I looked and I was that oh,
back in the day that would not have been there.
It would have been up here but me, you know, this and all that.
But yeah, I'm good. I actually don't feel, you know,
I'm, I'm a man of a certain age.I'll be in going into my 6th
(02:30):
century. I mean century, my 6th decade.
I'm 600 years old, right? I'm going into it by 6th decade
and I can't believe it. I look at myself and I'm like, I
don't feel it. And I don't think I think I look
younger than my parents. I feel the same way that I felt
when I was in my 30s. And so I really don't have an
issue with aging. I want to be healthy.
(02:51):
I'm not overly. I used to work out a ton and I
found out that I'm in better shape and I'm happier when I
just do everything in moderation.
And so I never really have. But yes, I am I happier.
Yeah, I am. Yeah, yeah.
You grew up with your mom and your grandma is your grandma.
Her name is Mary. Her name is Mary.
We called her Mommy. In Baton Rouge, LA.
(03:14):
Yes, well, it was in Port Allen,which is West Baton Rouge, Yeah.
OK, OK. Tell us about your upbringing,
because as I was reading up on you a little bit, I said like,
Oh my God, this dude and I have a lot in common.
You worked at McDonald's in highschool.
You were high school student body president.
Check. Check for me as well.
(03:34):
You were a Republican in college.
Wow, that I want to hear about that part.
I worked for Republican congressman in Washington DC
after my freshman year. I wasn't a Republican, but I
worked for Republican. You like Crocs, so we have a lot
in common. Tell it.
Tell us a little bit more about your upbringing and how the hell
(03:54):
you became a Republican in college.
I'd love to hear more about that.
Well. I don't know if you remember.
You grew up. Do you remember Alex P Keaton?
No. Which was Michael J Fox was Oh.
Oh, yes, of course. But so were you.
Were you sort of a Michael J Foxout?
I was. Talking with Michael J Fox,
Preppy Blue Jacket with gold buttons and white bucks and
(04:14):
khakis, that kind of thing. And I grew up in the South.
The South is very conservative and I, plus at first I didn't
like the Reagan's and then the longer he was in office, I began
to like him and, and then he didthe whole thing with the HIV and
AIDS and I didn't like him anymore.
However, I wrote him once told him that, you know, I really
liked him and that I was, I had registered as a Republican and
(04:36):
people thought I was nuts and blah, blah, blah, blah, blah.
And I got a letter back from theWhite House and my mom comes in
and she says, what's this? And I said, what do you mean
with this? She goes, this is a letter from
Ronald Reagan. And I said okay, and I opened it
up and whatever I have it somewhere in, in my memorabilia
thing. But I was young, I was naive and
I, you know, I thought it was cool and maybe I maybe I thought
(04:57):
it was kind of a counterculture thing to do back in the day to,
to, to have someone like me. And then once I became more
mature and learn it and I understood what was happening, I
quickly changed. I changed that.
But yes, I was. And I still have a bit of a
conservative streak. Yeah, like most people, you
know, I think most people have aconservative side and they have
(05:17):
a liberal side. And they're not so extreme as as
the media and and the politicians would lead people to
believe. And what part of you is
conservative would you say and socio political whatever?
I think I can be concerned. It's kind of weird.
It's, you know, as a gay man, I can be a bit conservative
sometimes socially, you know, sometimes I have conservative
(05:38):
thoughts and I go, well, I understand that.
I understand why they're saying that and I don't necessarily
disagree with it. And then people go on you crazy,
blah, blah, blah, blah, blah. And so, and I'm more on the
conservative side, except for lately conservatives have become
the party of cancel culture. I don't believe in cancel
culture and I believe in like ifyou if there's an issue that
someone gets in hot water for everyone's like can't talk about
(06:01):
it, whatever. I'm like, no, let's talk about
that. This is an opportunity to have
a, a constructive conversation about it rather than being quiet
about it. Like, you know, I, you know, I,
I would love to interview Marjorie Taylor Green.
She's mad at me. She won't do it.
And then sometimes some, some ofthe conservatives who say crazy
things, I would like to interview them.
(06:21):
Or sometimes some of the things that people get cancelled for, I
would like to interview them to have like a productive
conversation. Because many times through those
experiences, people will gain a point of view, right?
They'll have an epiphany or theywill change their minds through
that process. And if we keep ignoring it and
we keep cancelling people and not allowing them to go through
that process, I think that that is inhibiting.
(06:43):
And it's not, you know, it goes against what what we're supposed
to be about, what the world is about.
And that's evolution. We keep evolving, we keep going.
We it's bad, but it's about progression and not regression.
And so in college you had a girlfriend if I'm not mistaken.
I did. I had several.
I did too. The, the whole, it's in the
yard, the whole thing I did, I went there.
(07:05):
I'm not a I'm not a what do you call it?
What is it a goal? I'm not a gold gay or whatever
you call it. Gold gay What is a gold gay?
It's like a a gold and there's aplatinum or something when you
like some people said I haven't been with a woman or a lesbian
will say I haven't been with a man or never even seen the other
(07:27):
parts or whatever. Yeah.
Wow. OK, You're telling me things I
don't even know, but I So at at what point?
So you knew at a young age that you might be gay, but if I'm not
mistaken, and at some point along your maturity path, you
came out and what? We'll talk about that in a
(07:48):
couple minutes. But what was it like as a
closeted black gay man? Were you dating women?
Were you dating men? But not talking about it?
Where what was what was going on?
I mean, we want the, we want the, the DL on the DL that the
down low talk about from Don Lemon.
Well, I was doing what a lot of people do or did and what a lot
(08:12):
of Republicans do now. I was dating women, like in
public and then privately. I was, you know, secretly doing
things with guys. But, you know, because there was
a back then, there's a lot, there was a lot of shame around
it, especially in the Deep Southin the, you know, in the 70s and
80s. Yeah.
And so I had girlfriends. And the weird thing is this is a
(08:33):
weird, very strange thing. You don't know necessarily when
you're when when biology is going to catch up, right, When
the real thing is going to catchup because because of the
hormones and because I was so young, I had no problem being
intimate right with. And then I remember the first
(08:54):
time when I didn't, I became, you know, someone who was
actually of a certain age. And then I realized, like, I
don't really, I'm not really enjoying this.
And it was, it was a real wake up call for me because it was
someone who was a girlfriend andI was like, Oh my God, I'm gay.
If you're enjoying the conversations we've been having
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opportunity to flourish. Claim your copy today at
meawisdom.com/midlife Book. That's, I mean, that's when I
really realized it and I remember.
What age were you at that point?Probably sometime around high
school, High school or early college.
I just remember being at home alone and we were messing around
(09:59):
and nothing was happening. And before it didn't matter.
Yeah, it it always happened. And then but I think also too,
maybe it was her. Maybe I wasn't attracted to her,
you know, that's that really sort of crystallized the moment
for me. So you from a young age, you, I
think you like you were a fan ofMax Robinson and you, you would
(10:23):
actually videotape the news so you could actually watch it.
And, and so you know, at a youngage that you're interested in
the media and maybe even specifically being a, a
journalist and newscaster. And that must have been hard to
know a as you were moving into your adulthood, that this is the
career you want to be in and it's really hard to be out.
(10:45):
So how what was going on for youpsychologically during your 20s,
thirties and up to the point when you wrote your Seminole
book Transparent, which came outaround age 45?
Well, that, yeah, that was a long time, you know.
Yeah, it was a long time. That was a long time.
So in college at at LSU, I knew what was up by the time I got to
(11:06):
college and I would hang out with my friends.
I would date girls. I would go to the bars with
them, all of the dude bars and all of the frat guys and we
would go and then right down thestreet.
Were you in a fraternity, Don? No, I was, I was not in a
fraternity, but my friends were in fraternities.
You know, I went to LSU, which was not, which was not an HBCU.
And so it was, you know, majority white college.
(11:28):
And so frat life there was really big and sorority life
really big. You go to this fraternity row
and sorority road, and I was senior class president and I got
all these letters from the fraternities saying come join,
come rush or whatever. And then when I got there,
they're like, oh, you're black. This was LSU in the 80s.
Yeah. And so it was not happening for
me. So I was like, you know what?
(11:49):
I don't want to be a part of this shit where this white
fraternity or black fraternity is bullshit.
And so I didn't, but I would go out.
We would go to this place calledthe Bingle because it was LSU
Tigers and we would hang out of the bingo and then everybody
would get smashed. And then I would ultimately
sneak off and go to the alternative club, which was like
2 blocks away and I would sneak around and run and go into the
alternative club. And that was sort of mixed.
(12:09):
It was just like these sort of unusual punk rockers or you
know, counterculture kind of folks.
And then across the street was the gay bar.
I think it was called Neiman's then and every.
Like Neiman Marcus. Yeah, like the first time I
went, I snuck across and I went to Neiman's and my whole world
was like. Oh, this is so wait, wait, wait.
(12:30):
We got, I can't believe we're having this conversation.
So what my first time coming outwas at age 22, I was working in
New York for Morgan Stanley for the summer.
I was between my first and second year of Business School.
I was living at 86th and Riverside and I, and it was 4th
of July and 1983, so serious agecrisis.
And I walked from 86th to Riverside, all the way down to
(12:52):
Uncle Charlie's, a place in the village.
My gosh, I have an Uncle Charlie's story.
Oh, OK, we're going to go there.I say, who knew?
OK, thank you. This is this is fun.
Charlie's. No, we never.
Well, I wish we had because I would have dated you, dude.
I mean, you're you're hot. So I went into Uncle Charlie's.
First time I'd ever been in a gay bar.
(13:14):
Only had dated women previous tothat.
Was dating a woman during that summer.
And I walked in and it was like the Wizard of Oz.
It was like, you know, when the,the, the house came down and all
of a sudden Technicolor, you know, in Munchkin Land.
And I, I met a guy, you know, a Puerto Rican guy named Victor.
That's that night. And we spent the summer
(13:36):
together. And so that was my experience of
my first gay bar and and then myfirst boyfriend for the summer.
Isn't that amazing? Isn't New York City amazing that
way? Because I had I had a very
similar experience. So I would house sit for my aunt
in early high school, early college, but it wasn't until it
was all around the same time 838485 in there.
(13:59):
So I would go to the names and that was eye opening.
But then when I would go to New York and house sit for my aunt
in the summer, they take these great vacations.
They go to Egypt for like 4 weeks and whatever.
And so I would, I would house sit for their They had this
townhouse in Harlem on Convent St. in Sugar Hill.
And I had that entire like four or five, six story house to
myself. And so I would.
I had one night I sneaked downtown and I went to Uncle
(14:22):
Charlie's, right? And is that your first?
That was your first gay bar in New York.
Those are my first gay bar outside of yeah, outside of Ian
and Nieman's One Night and My Mind being.
You're underage, you're underage.
You're doing that. No Jaws only.
I was not underage. I was 18 years old. 18 was a
drinking age in Louisiana. Oh, but in New York, though?
(14:45):
Oh, I don't know. I don't know.
I never even thought about it. Was I that we're not going to no
one, you know, statue anyways. I got in, I got in.
So, you know, it could 8/19/22 and it could be like I said, 85
or that would make me 2020 sort of on the edge.
That was probably why I didn't go in high school because I was
too young. I think maybe it was just like
around, you know, I was 21 and so I went and I was so nervous.
(15:10):
And this was during the time of,you know, the big buff body,
everybody, the big buff shaped body and you know, big blonde or
whatever. Everyone looked like a like AGI
Joe and I didn't look like AGI Joe.
This is like, I didn't think I was hot.
I was skinny and I look back on pictures and I'm like, damn,
you're a hot. You were a twink and you didn't
know it. So I met this guy and that was
(15:35):
like my first real experience. I met this guy and we went home
and is a white guy, discovered alot of things about myself and I
don't know, I've never seen him again.
But it was also kind of frightening because it was
during the aids, whatever. So we were very careful.
Luckily, you know, I'm alive and, you know, in good health,
(15:56):
and I'm so happy that we have the drugs now to do to take care
of of folks who are positive. But anyways, I digress.
Yeah, that was my experience around then and it was I
couldn't wait to move to New York.
Yeah, me too. I loved, I loved New York.
So you had been 20 years, more than more than 20 years of
living this life. And then what was it that that
(16:19):
led you to writing this memoir, this coming of age coming out,
coming out story in your mid 40s?
And were you going through a bitof a midlife chrysalis, meaning
the idea that you something was shifting in you and instead of
it being a crisis, it was a doorway and maybe to a whole new
life. And are you happy you walked
(16:39):
through that doorway? Well, as you know, like,
especially if you are our age, right, there's a, there's a,
there was a dual life that you had.
So finally, when I left, I, you know, I would hide the gay part
from my friends and I kind of lost touch with my college
friends and then I moved to New York and then I then I reunited
(17:01):
with them and you know, that's awhole nother thing.
But I finally moved to, I realized that I had to in order
to be who I was, who I, who I should be and to achieve or
accomplish the things that I wanted to accomplish that I
would have to leave Louisiana. And especially after my journal
professor told me that I'd nevermake it as a journalist.
And I said, oh, OK, So I left, Ileft LSUI, left Louisiana and I
(17:23):
moved to New York. While I was in New York, I was
out amongst friends and some Co workers, but not to everyone.
I didn't tell my family, I didn't tell the people who are
closest to me. And eventually a college friend
called and said, Hey, Don. And, you know, I was living in
New York. He was in Louisiana, or I think
still in Louisiana. He said, I hear that you might
be gay. And I don't care.
(17:43):
And that's how I reunited with my college friends.
And then I eventually have founda boyfriend that I'd been dating
for a couple years. And we broke up, and I was
heartbroken. And my mom was kind of my best
friend. I would talk to her every day,
even though we didn't live in the same city or state.
And I told her and I said, she said, what's wrong with you?
You just don't sound the same. And I said I'm just not happy.
(18:04):
And she said why? And I said because of my
relationship. And she said with who?
And I said John and she goes what kind of relationship?
And I said he was my lover. And I started crying.
And then so I came out to my momand then she said, well, I
won't. I said don't tell dad, don't
tell anybody. And 20 minutes later I get a
call. I Don it's dad.
I'm like oh fuck. And she told them and she told
(18:30):
my sisters and whatever. And then I was like, OK, I'm
out. It was weird because she was
very much in, in control. And then she kind of fell apart
lately. I mean, later, you know, it's
just like, oh, you know, I wanted grandkids.
And she went through that whole thing.
And then now she'd be like AP flag mom because she is all in.
She's like, talks to my husband.I love you guys.
(18:51):
All kinds of things. You know, she sends presents to
the dogs and. Yeah, so she's all in and she's,
you know, people. People can change and they do
evolve. So that's what happened.
And so by the time I wrote that book, I was out to my family,
but I wasn't out publicly, you know what I mean?
People at work knew for the mostpart.
(19:11):
If you were friends with me, I didn't really talk about it at
work, but people knew. And then someone asked me to
write a book, a publishing company.
And I said, OK. And I said, you know, what is
about? It says we want to know you're,
you know, you're a man in mainstream media and you're a
black man and not not many people get to this level.
And we want to know what it's like.
So I started writing about it. And then I got to the point
(19:32):
about when I left Louisiana and I was like, God, how do I write
this? And I said, I just have to write
it. I said, I cannot.
I have to have the same standardfor me that I have for everybody
else. I have to be honest.
And I'm not going to lie in thisbook.
And so they, the publisher said write it.
The editor said, just write it. We don't have to use it.
And I wrote it. It came time to there's like,
(19:53):
OK, we're going to go to print. Do you want this in there?
And I said, you know what, fuck it, put it in there.
But I thought I was going to lose my livelihood.
I thought people weren't going to want to watch me.
I thought I would get fired. And the exact opposite happened.
I'm sure there that look, there was some people I'm sure who
would you know that had negativereaction to it, but.
It was overwhelmingly positive and it gave me a sense of
(20:14):
autonomy that I didn't have before.
And the freedom, I mean, it was just, I said weight was lifted.
Yeah. So this was.
Nobody who's been to Christ, nobody was.
Nobody's out. Nobody was me.
And then Rachel Maddow was out, I think.
But Rachel wasn't. She wasn't Rachel like she is
now, right? Yeah, yeah, yeah.
(20:36):
She sent me flowers and yeah, I think that was.
Did what changed inside you? How did you evolve this
chrysalis moment where you started?
Maybe you were actually emergingfrom from the chrysalis and the
butterfly is there. Like what?
How did you know it affected your midlife?
(20:56):
Because you were right there in your mid 40s when all this
happened. Like I said, it gave me a sense
of autonomy. But also it was very similar to
when I told my mom, if I told mymom that I was gay and she was
OK with it, then nothing else mattered.
And when I wrote the book and I started reading the book to my,
I would read the galleys to my mom and we would sit and read
(21:16):
and she's like, and I would say,mom, can I tell about your
affair and that I'm the product of an affair?
And she goes, yeah, tell it all.Tell it all.
She goes, I have nothing to be ashamed of.
You have nothing to be ashamed of, ashamed of.
And so once my mom said that that's that was the real reason
where I said printed F it. But still I thought, you know,
I'll just have to go do something else in life.
If if I can't, you know, continue with this career.
(21:39):
It, it gave me a sense of freedom and that I had never
experienced before and the confidence that I had never
experienced before. You know, I used to think then
before then I used to think thatI didn't care what people said
about me. But there are levels to that
because then I really didn't care about what people have to
say. I don't care about other
people's criticism. But it's also from having that
(22:02):
those types of moments ship or having, you know, that moment or
those types of moments in your life.
People wonder why I you know, I will put things out there when
people don't agree with me or ifI have an argument and they
think like, Oh, you didn't get the better side of that
argument. It's like, I don't care.
It's what if that's what life isabout, like you.
And and so we are all, you know,going, Oh my gosh, this person
(22:23):
destroys this person. This person did that.
We're in that kind of culture. This person is a jerk.
And we're I'm not there anymore.I don't really care what you
call me and I don't really care what you think about me.
I care what I think about me. And that that experience taught
me that. So yeah, it was a chrysalis that
I live with my entire life is a chrysalis.
Yeah, so I read a book. Ongoing case now.
(22:43):
Yeah, I wrote a book called Learning to Love Midlife, 12
Reasons, Reasons Why Life Gets better with Age.
And what I'm hearing is one of the reasons life gets better
with age is, you know, have no more FS left to give.
You don't get more. There's an element of like, you
know what? I'm just going to be who I am.
I care about things, I care about people, but I'm going to
be less possessed by being a people pleaser.
(23:06):
And I think women in particular,but I think gay men actually go
through this in as well in termsof we've tried, we've tried to
do what we can to be the best little boy in the world.
We've we've done what we can to actually fit in and you in for
in your case, you have that the,the double fitting in of being
a, a black person as well as being gay.
(23:27):
And there's an element of like, wow, you just, this is who I am.
Yeah. What?
It's not just for you people pleaser.
It's also being an overachiever.A lot of gay men I know are
overachievers. You got us, you know, you got to
be the best at everything. So it could because it's an
armor that you build up. And yeah, I've been a people
pleaser, but not not anymore. Every once in a while I feel it
(23:48):
like creeping and they go why doI care?
Yeah, So what else has gotten better with age for you?
Sex. OK, tell us more.
Dude, you're going there. I love this.
I, you know, so for everybody toknow, Don and I have never met
before. We've just commuted by e-mail
and text. So the fact that Don's going
(24:10):
there on this call with me is very much appreciated because
again, why not? What kind of path are you
carving through midlife? Our free Midlife Pathfinder Quiz
helps you discover which of eight archetypes best describe
your approach to the stage of life and what that means for
your next. It only takes a few minutes, and
(24:32):
your results may surprise you. Find out your archetype now.
It's quick, it's fun, and it might help you see your journey
in a whole new light. Take the Pathfinder quiz at
meawisdom.com/quiz. Well, I mean sex because you
know who you are and you know what you like and you know what
to do and, you know, it's like sex with a novice is not really
(24:56):
that much fun. I mean, you know, it sort of
wears off, right? So yeah, the sex is good and it.
And it's not just about getting to the end.
It's about all of it. It's about the beginning, the
middle and the end. You know, I don't care like
anymore. It's like, Oh my God, if it when
I take my shirt off, is this person going to think I have a
good body or not? I don't fucking care.
(25:17):
I don't care. You know, this is to have a good
time. But I'm also married now, so it
doesn't really matter. I'm off the market.
But so and then also what's gotten better, confidence has
gotten better. I actually think that I get
better looking with age. I think you do.
This black don't crack girl. I mean, you like you look really
good. Thank you.
You know, I looked at you know who Steve Scalise is, right?
(25:39):
Yes. Steve Scalise and I went to the
same college. He was in the same fraternity as
my friend and. From Louisiana Republican
congressman from Louisiana. With the same age, he was born
in October of 65. I was born in in March of 66.
I look at Steve Scalise and I say, you know, I it just gives
me, I'm like, I don't look like that.
(26:01):
And I know, but I think I would look if they're one.
Of I don't think he's going to give you an go, let you
interview him again after sayingthis.
Or whatever I did, they hate, they don't want to interview
with me anyways because you know, you're afraid of the
truth. I feel I don't look like that.
And so I'm like, I don't feel that age.
And I think that's a lot. I think that has a lot to do
with it that I don't have. I don't have secrets Chip.
(26:24):
I don't have any sort of weight on my shoulder.
And I think that that is very helpful.
I'm very open minded. I'm very I allow people to be be
who they are. I accept things for what they
are. And I think that has a lot to do
with remaining remaining youthful even as you are aging.
I love getting older. I don't want to reach a point
where I want to be a mobile. I want to be mobile and I want
(26:47):
to have my wits about me. Other than that, the alternative
is not to be here and I would prefer to be here and living the
best life I can at whatever age I might be.
I would not want to go back to my 20s, no or no, and let if I
knew what I knew now, perhaps I wouldn't want to go back to that
time. So let's talk about something
you said a couple of years ago. But, well, it was during the
(27:09):
2020 election. It was about Nikki Haley being
passed her prime 2020. Was it 2024 or 2024?
Yeah, it was 2024 because, yes, of course.
So that was not long ago actually.
It was in 2023 that it happened.Yeah, 2023.
So if you could take that back, would you take it back?
What let's, let's, let's set this up because what you said
(27:31):
and again, this is the only timeI'm going to ask it.
You can ask me anything. I'm glad you're asking me this
question, but. And and so the question was you,
you said that maybe she was pasther prime and she was, you know,
that and something about, you know, women maybe in their 40s,
we're past, might be past their prime.
(27:52):
And it sort of blew up. You got a lot of shit for it.
And I want you to just sort of maybe unpack that a little bit
because this, this, this podcastis really about aging and about,
you know, not men, women and everybody in between.
So how do you feel about that now?
Well, I wish I, I wish I could have been clearer and people
could have understood and I wishthe company that I work for
would not, would have stood behind me rather than making it
(28:15):
an opportunity or predicate to, you know, to try to marginalized
me in a certain way, right, to, to try to restrict me.
But if you go back and look at that clip and, and it's besides
the headline, if you really go back and look at it, what I said
is I don't believe that. So my point was, is that society
believes that and Nikki Haley should know better considering
the way society treats women. And that was the point of it.
(28:38):
And so she's saying that Joe Biden is too old.
She's being an ageist, but society is also thinks that
she's old at a woman who is 51 years old.
That's what society teaches us. I said, I don't necessarily
necessarily believe that don't shoot the messenger and the
messenger got shot. That's, that's all that I meant.
I don't, I don't think women arepast their prime at any age.
Or you can do what you want. I think for me personally, I'm a
(29:02):
very logical, rational person. So and at someone who is of a
certain age, I am past my prime.It's OK for me to say, to know
that it's OK for us to be able to say that because some people
feel like, Oh my gosh, you know,how can you say that?
And I'm so hurt by it. No, I can't run.
What does? That mean though, darling?
It means for me, what it means is that when I think about it,
(29:24):
when I was in my 20s and 30s, I could run 10 miles and not be
out of breath. That is fact.
When I was in my twenties, 30s and 40s, I was sharper.
Now I have to recall things and so physically and mentally,
there is a time where we are firing on every single cylinder.
And as we get older that goes away.
(29:45):
And that's OK though. And so I was saying that about
me. I'm not saying that you may feel
differently it it could be you at 708090.
And basically that's what Nikki Haley was saying about Joe Biden
is that he was too old, that he was past his prime.
That's what she was saying. And so when someone says that
about her, she gets upset and then she fundraises off of it.
(30:06):
So that's all I'm saying. But it's OK for me.
I'm a different person. If some people maybe that hurts,
but there's we have to be realistic about what happens to
us. Now, I do think that I get
better looking as I get older, but you know, I'm a different
person now. I'm not the same person that I
was in my 20s, thirties or even 40s.
And soon I won't be the same person I am in my 50s.
(30:26):
So it is true that, you know, mental acuity and being able to
be fast and focused does actually decline with age, but
wisdom actually can grow with age.
And this idea of crystallized intelligence, you're able to
connect the dots. I mean, do you think that
people, women do the women are held to a different standard
than men when it comes to 8? Percent at a different standard,
(30:47):
and it's unfair, an unfair standard.
About that. Because because when and again,
my point, men can have kids at any age and it's always that, Oh
my gosh, men age like fine wine and then they don't say the same
thing about women and my. Silver foxes, Yeah, the silver
fox and not a silver vixen like a silver.
(31:08):
And so that's. Right.
That was my point. Like, don't you know that, like
Nikki Haley, why are you doing that?
Why are you pointing out something about somebody else
that people have been saying theway, you know, for centuries
here in the world, that a woman has to be a certain age when
she's in her prime? That's it.
That's all I was saying. So I'm glad you gave me the
opportunity to talk about that. But I it wasn't to any point
(31:29):
where I was saying that's what Ibelieve.
Yeah, and, and there's lots of different forms of prime.
So there's, you know, prime. You know what, especially there
are a lot of amazing female politicians, Nancy Pelosi being
one of them. Who had Nancy Pelosi prime was
certainly in her 70s and early 80s.
Nancy Pelosi may still be in herprime.
(31:51):
Did you see how she handled thatreporter the other day that
asked her? Yeah, yeah, yeah.
Thank you. Thank you for unpacking that.
Nancy Pelosi, she has a bad ass.So let's talk for a minute.
We've talked an awful lot about other things, but the state of
the world, the state of media, the state of you going
independent and building the DonLemon brand, which is blowing up
(32:12):
in all kinds of wonderful ways. If you could prognosticate to
where we are say five years fromnow in 20-30 in terms of media,
in terms of politics, in terms of society, where do you think
we're going to be? Is is are we at the trend line
has been seemingly pretty bad, but do you have some hope?
I do have hope. You mean where are we going to
be just in general in the world or in the whole media landscape?
(32:35):
The. Media landscape but the let's
just let's focus on the US, let's say in the US.
Do you have how what's your what's your feeling five years
from now in terms of the nature of media, but also the nature of
the socio political world and you know how divided we
currently are? Well, I think successful part of
media and the people who are in media will be somewhere between
(32:55):
independent journalism or something that is free of
corporate influence. And you can see that happening
now because there's just too much of it and people are sick
of it and they can tell when people are pulling their punches
and and on and on and on. So I think that's what then.
People are narrow casting now and they want to get information
from people they trust and they like and they don't know
necessarily they trust what they're seeing in the mainstream
(33:17):
media right now. And so that's good for folks who
are like me, the whole socio yousaid socio economic and
political and political. Well, I will tell you about the
world is about evolving. It's about evolution.
It's about recreating and procreating and whatever and
otherwise then we die. So if anybody thinks that we're
going to go backwards and anything is sadly mistaken.
(33:39):
The world will continue to evolve and we will.
The truth will come out and people will start to figure out
like, you know, that they're being bamboozled by this current
administration as they are finding out now.
I do believe right now that thiswhole thing that's happening
with Epstein and, and, and otherthings that the spell is being
broken for the, the sort of cultpower that Donald Trump has over
(34:01):
in the MAGA movement has over people.
So how what do I see in the future?
Like physics, the pendulum swings one way and then it
swings the other. And just as hard as it swings
that way, it's going to swing back the other way until it
eventually corrects itself. So I think by 2028, we're going
to have a Democratic president and a Democratic president is
going to get in there. And it's going to have to fix
the Supreme Court, whether that's expanding the court or
(34:23):
whatever. And so if Republicans get mad at
it, so be it. They're going to have to because
look at what happened. And so I think we're going to,
we'll, we'll be in a state of correction for the next decade
or two. And then, you know, we'll get
back to normal because this is certainly, you know, a sort of
upset the apple cart. This was like a meteor that hit
us. And we've got to, you know,
we've got to pull ourselves together from it.
(34:44):
So I think that's where we'll beat least in the next 1020 years.
Will you ever retire? No.
No, OK. No, especially now.
I mean, why do I have to? Why?
Seriously, why do I have to retire, Right, Boomer?
I mean, I'm in my home studio, my dog is here.
I'm earning a living. I get to hang out with them.
I get to speak to the people I want to speak to.
(35:05):
I if I don't want to do something I don't have to, and I
love what I'm doing, why would Iever retire?
I'm still in my prime ship. You are, you are.
So yeah, it's very interesting our relationship with retirement
these days. You know, when when people were
doing back breaking, mind numbing labor, getting to 60 was
(35:28):
like, oh, thank God, finish line.
I can now go live in Sun City and, you know, play golf and
have martinis at lunch and play bingo at night.
But we have, Yeah, exactly. We have completely shifted this
narrative. And you're a Gen.
Xer, you're an older Gen. Xer.
I'm a younger boomer. And our, our generations don't
(35:49):
want to do that. We, we often want to try
something new around age 60. If I want to ask you 2 last
questions, 10 years from now, what might you regret if you
didn't learn it or do it now? I might well, I might have, I
can say what I might have regretted if I had stayed in
traditional media. I would have regretted staying
(36:11):
in so long because now I have this freedom to do, which is
kind of a weird sort of it's notretirement, but you get the
benefits of being retired because you don't have to go
into an office and you get to set your own path.
So I might have regretted that. There's you know, I always said
I have no regrets and I really don't.
If there is one thing I wish I would have done, I guess that's
the regret, right? I wish that during COVID, I
(36:33):
would have taken the opportunityto travel more and do my show
because I had the opportunity was offered, I could have moved
anywhere in the world or whatever, as long as there was a
good connection, connectivity and I could have done the show
because lots of the shows were done from, you know, my, my home
studio. So I could have been at a home
(36:53):
in Florida or a home in California or a home in Hawaii,
right? And I wish that I would have
taken that opportunity to do that, but I unfortunately I
didn't, but. That's it, we learn our lessons.
And may have. And also, excuse me, maybe kids,
maybe one. Yeah, having kids.
Yeah, I'm lucky enough to have a13 and 10 year old with a
lesbian couple. Nice SO.
(37:16):
Congratulations. Okay, last question.
So let's say someone younger than you, they could be in the
media or they could be a black gay person from Louisiana, or
they could be just a friend of afriend.
They come to you and say, hey, Don, I'd love to have tea with
and coffee with you next week. And I'd love for you to come to
our time together with a bumper sticker, a Wisdom bumper
(37:37):
sticker. Not a not a figure, not a
literal one, but more like a figurative 1A wisdom bumper
sticker. Something that you have learned
maybe the hard way because our painful life lessons are often
the raw material for our future wisdom.
What's the bumper sticker that defines Don Lemon's wisdom and
what's the origin story for it? OK, this is so weird because
(37:59):
when you reconnected Chip, I said to you, what did I say to
you? Well.
We talked a few different times.You know, when I dialed in, what
did I say? Can you see me?
Yeah, you take your shirt. You were taking your shirt off
because you were going to changeyour shirt.
Okay, so are you going to take your shirt off in front of the
camera now? So the shirt that I was wearing
has the. Okay, yeah, I didn't see this
(38:21):
shirt. The shirt that I was wearing has
the exact thing on that you wereasking me about, and that I
will. And it sums up the conversation,
how I feel about everything whenyou talk about prime and all of
that and how I respect people ofevery age.
But I'm realistic about myself and I don't have the same.
I don't believe that everyone has the same standard that I
(38:42):
have. And so people might think that
their prime is whatever age theywant to think.
So I've explained that this is how I feel about aging, this is
my saying, and this is my show logo.
Old people be known. And then it has a Don Lemon logo
there. Old people be.
(39:03):
We know shit. So that's wisdom.
We know. We get our Spidey senses are
sharper. We know and so all of this, if I
could say bullshit that's going on, we see through the bullshit.
I can tell when somebody's bullshitting to me.
I can tell when someone's a goodperson.
I can tell whatever I can see around corners as a man of a
certain age because I'm old and old people be knowing.
(39:24):
That is what I would tell. So enjoy your youth.
Enjoy your youth. You can do all those things.
You can run 10 miles without dying, right?
But however, and some people cando it, I mean, people run
marathons in their 90s, right? You know, enjoy your youth, but
there's something that you can only learn from remaining on
this planet, surviving, and thatis wisdom.
(39:45):
And so that will come one day. And so no matter what happens
when you're young, there's always something to look forward
to and you have wisdom to look forward to.
And so just put yourself in a position where you can get to
that point in your life where you're like me and the devil may
care and you have 0 FS to live because old people be knowing.
Yeah, old people be knowing thatthat that is going to I, I I
(40:07):
want to get one of those shirts one of these days you and I are
going to get. Go to donlemon.com and click on
merch and you 2 can have. OK, there we go.
There you go guys. donlemon.com,The merch is right there.
Someday you and I are going to watch All About Eve together.
I know you love that film. I do.
Every line. Do you know it?
I mean, I don't know every line.No me you do.
(40:27):
Although every single line. Wow, the fact that you know that
movie as well as you do and you love Judy Garland, dude, you're
a gay man. I can tell you I'd.
Be gay. I love Judy Garland.
I think Judy Garland is one of the best singers and performers
ever. And you know the weird thing
people talk about, You know, voices like, well, you know,
Whitney Houston's incredible voice.
(40:49):
Barbra Streisand has an incredible voice.
Aretha Franklin and all that. But it's also in how they did, I
think the most perfect voice that that ever was Whitney
Houston. But Judy Garland, you feel her
life coming through that microphone, right?
And you see it. It's just, I remember when I
discovered Judy Garland beyond the Wizard of Oz, and that was
(41:11):
how hard were you? Oh, I was, God, I think I was
in. I was either late, late high
school, early college. I think it was early college.
You know, Judy Garland live at Carnegie Hall.
And I think I bought ACD player and I went to the CD store and
they had the unedited version ofthat.
I put it in the CD player and I've never taken it out Now, I
(41:32):
mean, and now I, I stream it. But yeah, when you're smiling,
when you're smiling, the whole world smiles with you when
you're laughing. And it starts with that.
When you're laughing, the sun comes shining through.
Yeah. So that was my Judy Garland is
amazing. I think she's fantastic.
I having just heard you, I wouldsay the one regret you may have
(41:55):
if you don't do it in the next 10 years is you're supposed to
be a Broadway performer. There you.
Go. I I can feel it.
I can feel it. I would love to Broadway.
Don Lemon, thank you for joiningus.
Done. Chip Connelly.
We're done. I, I hope that wasn't painful.
That was like. For months we've been and I
(42:16):
look, I, my schedule was crazy and you know, I had to
reschedule a couple of times. I apologize for that, but that's
it. That's after all of that.
All of that. Listen, dude, people are going
to love this. Your love, the unfiltered Don
Lemon, the truth teller and the human, just the beautiful human
specimen that you are. You are a moral beauty.
I said that to Maria Shriver. I will say that to you.
(42:37):
You are a moral beauty. Oh, thank you, Chip Connelly.
I hope to get to meet you in person.
You're out West, right? I'm in Santa Fe right now.
I'm, you know, I'm in Santa Fe, Baja, San Francisco, Austin.
I get, I get around. So yeah, I want to talk to you
about. We'll talk offline.
I want to talk to you about. We're let's talk about Austin
and we'll I'll come, I'll come visit you in New York.
(42:58):
All right, Thank you. OK.
I did not expect that. I did not expect that that
episode to go as personal as it went.
And you know, I will admit a long time ago when I was
watching no, that long ago, maybe 10 years ago, I was
single. I Don was single.
(43:20):
He had come out and I was like, you know what, he could be
boyfriend material. So I do believe and I, you know,
he's, he and I probably were separated at birth because we
have so much in common. So my first lesson is he used
the word evolution 2 times, maybe even 3.
And I think that was interestingbecause this is, you know, not
(43:40):
something I would have expected him to, to, to use because it's
very much of a personal growth kind of word.
Things evolve, people evolve. And so I think one of the
beauties of if you look at Don and from his, you know, humble
upbringing in, you know, Baton Rouge, LA, being a Republican in
college, learning over time thathe had to be closeted.
(44:03):
He's evolved. And one of the things that's
very clear about him today is there's that he even said it,
his confidence, but it's just his sense of who he is.
You know what the the beauty of just showing up and being who
you are and whether people like it or not, you just do that.
And I, I feel very similarly in my own life that I can do that
and hopefully you can too. Second lesson is no more FS left
(44:25):
to give. No more fucks left to give.
It is one of the 12 reasons why life gets better with age in my
book, Learning to love midlife. And I think, you know, that's
where Don is right now. I think it was in many ways, it
was that experience with Elon Musk.
You know, he was going to be doing things with X and it was
the experience of the thing I brought up to him, the Nikki
(44:46):
Haley comment about being in notbeing in her prime, that had him
get to a place where he said, like, I I don't need to deal
with all the politics of, you know, of traditional media.
And he's. Yeah.
I think one of the things that people appreciate about Don and
sometimes some people don't appreciate about him is he just
sort of says it like it is. You know, again, I think that's
(45:07):
something that that is true of us as we get older.
We have unvarnished insight. And that brings me to the third,
third thing. Now, I thought he was going to
take his shirt off and put the other one on.
And that would have been interesting.
And we would have gotten more YouTube use as a result of that.
But no, he he just brought over what he had taken off before we
started recording, which was this T-shirt that says old
people be known. The idea of wisdom.
(45:28):
His wisdom bumper sticker is really about wisdom, is about
the fact that as we get older, ideally we get wiser.
Hopefully the world is better off for that.
Many of you know, my wisdom definition is a metabolized
experience mindfully shared for the common good.
And for the common good is such an important part of that.
Wisdom is a common good. It is meant to be shared and
(45:49):
it's meant to make all of us better.
So I hope that you found a little nugget of wisdom, a micro
dose of wisdom in this episode. We'll see you on Wednesday for
Wisdom Wednesdays, where I have a conversation with Derek Gale,
the CEO of MEA. It's a short run.
So I, I, the beauty of the, the wisdom Wednesdays is they're
short. And so you can listen to them
very quickly. And hopefully we're delivering a
(46:10):
little bit of wisdom to you. Wishing you all the best.
See you on Wednesday. Thanks for listening to The
Midlife Chrysalis. This show is produced by Midlife
Media. If you enjoyed this episode,
help us spread the word by subscribing and leaving a review
on your favorite platform.
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