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August 14, 2026 22 mins

What if the key to building a successful life isn’t having everything figured out—but simply doing the job that’s right in front of you?

On this episode of The Karol Markowicz Show, Karol sits down with Matthew Hennessey, editor of Free Expression at The Wall Street Journal, for a wide-ranging conversation about career, marriage, ambition, failure, and finding your path in life.

Hennessey shares his unconventional journey from chasing an acting career in Hollywood to becoming a journalist and eventually landing at The Wall Street Journal. He explains why meeting his wife became a pivotal moment in both his personal life and career, and why young people may have it backwards when they believe they need to establish themselves professionally before getting married.

Karol and Matthew also discuss the value of taking risks, learning to do difficult things, supporting children as they pursue uncertain dreams, and why success often comes one small step at a time.

Hennessey also explains what The Wall Street Journal represents beyond finance and Wall Street, shares his concerns about the possibility of a major economic downturn, and offers a surprisingly optimistic perspective on artificial intelligence and the economy.

Finally, he leaves listeners with a simple piece of advice that has guided his career and life: Do the job that’s in front of you, and the future will take care of itself.

Follow Clay & Buck on YouTube: https://www.youtube.com/c/clayandbuck

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Speaker 1 (00:05):
Hi, and welcome back to the Carol mark Wood Show
on iHeartRadio.

Speaker 2 (00:09):
My guest today is Matthew Hennessy.

Speaker 1 (00:11):
Matthew is the editor of Free Expression, a daily newsletter
on life, politics, and culture published by the opinion pages
of the Wall Street Journal.

Speaker 2 (00:19):
Him Matthew, So nice to have you on.

Speaker 3 (00:21):
Hi, Carol, Thank you for having me. I'm such a
big fan.

Speaker 1 (00:24):
I'm such a big fan, and I you know, I
love the work you're doing it Free Expression. I feel
like it really aligns with this show in that it's
about culture, it's about living better. It's just about all.

Speaker 2 (00:35):
The kind of things that you know make life worth living.

Speaker 1 (00:39):
And are not explored in pages of other opinion sections.
So I really love the work you're doing. I like
the piece that I wrote for you about how six
seven is not that bad, although I have to say
directly after that was published, I think six to seven
die to death.

Speaker 3 (00:56):
Yeah, but I think you had something to do with it.
I think the last line and the last your sort
of suggestion, and the piece was that if parents are
getting tired of this, they should just start saying it
and it will go away real fast. And that's exactly
what happened. That's a good job.

Speaker 1 (01:13):
As soon as the Wall Street Journal published a piece
on it, it was over, which makes.

Speaker 3 (01:16):
Cats out of the bag. By the time it gets
to this desk, it's no longer cool. That's like by definition,
How did you get into this?

Speaker 1 (01:24):
How did you get into this thing of ours being
in media and running pre expression?

Speaker 3 (01:30):
Well, I am. I am your classic late bloomer. I
didn't even start trying to get into journalism in any
kind of a way until I was over thirty, over
fifty now, so I've had a good twenty years at it.
This point, my story was kind of meandering. I spent

(01:50):
my twenties trying to break into the arts. I was
an actor and a musician.

Speaker 1 (01:57):
And.

Speaker 3 (01:59):
It went pret well for a while, and then when
it got difficult, I gave up the way you sort
of do when you're young and easily frustrated. And things
sort of changed for me. When I was in my
late twenties, I met a nice girl and we decided

(02:20):
to get married, and that sort of helped me turn
things around. I went back to college. I started to
get a little political around that time. It was this
was nine to eleven. Happened. I sort of started seeing
the world in a slightly clearer way than I had

(02:40):
been as a younger man. And I discovered that I
was actually pretty good at something that I didn't even
realize I was good at, which was, you know, slinging
words around. And so I slowly sort of groped my
way towards this career. I worked at some think tanks
for a while while doing some editing and some writing,

(03:02):
and writing on my own and sort of submitting pieces
to the newspapers that we both love, like the New
York Post occasionally the Daily News. I would try my
hand at the Walls ever got anywhere close to it,
but you know, time and patience will take a snail
to Jerusalem as the set.

Speaker 2 (03:21):
So where was your first kind of big break?

Speaker 3 (03:26):
Oh? Maybe I haven't even had my big break yet.

Speaker 2 (03:29):
Who knows writing in the Wall Street Journal. I feel
like it's kind of up there.

Speaker 3 (03:35):
Well, that was That was probably my biggest break, was
getting the job here. I never I never wrote for
the Journal. Before I got here, I was working for
a magazine called City Journal, which everyone sort of knows now,
but maybe you know, fifteen years ago, the profile was
a little lower. I can you know when I got
that job. Every break that I've gotten has been a

(03:55):
big break, you know. That's that's sort of the nature
of things. You never get everything all at once. You
you sort of climb slowly if you're doing it right,
and every step of the way feels like it's a
big break. So when I got the job at City Journal,
I thought my ship had come in. Every job is
a good job, as they say, So I guess my

(04:16):
big break was getting this job here for sure in
twenty seventeen, so almost ten years ago.

Speaker 1 (04:22):
So what were those acting in music years, like, like,
what were you doing? What were you trying out for?
What was kind of what was the thing you were
aiming at?

Speaker 3 (04:31):
Well, I wanted to be a movie star. I did
live in California from the East coast, but for a
solid three or four years I lived in Los Angeles
and I was running around buying gas and cigarettes with
a credit card and taking auditions. And I can't lie

(04:54):
and say it was a disaster, Like I did fairly
well considering certainly considering the amount of work that I
put in, which was not very much. I was just
sort of going on youth and energy and I had
long hair. I was trying to sell a particular look
in the nineteen nineties. But like I said, when things
got hard, I really just sort of crumpled. You know,

(05:18):
I was twenty two, twenty three years old, and it
would have required a sort of a level of commitment
and maturity that I just didn't have at that time.
If it was going to be easy, I was happy
to do it. I was happy to keep trying my
hand at this, at this crazy dream. But you know,
like every crazy dream, it's going to get hard eventually,

(05:39):
And when it got hard, I really I just gave
up and I left. And sometimes, you know, for years
after that, I sort of kicked myself because I you know,
you grow up a little and you realize that you
can do hard things, you do actually have to do them.
They're not just going to all come to you, or
the rewards won't all just come to you. So sometimes
I have occasionally had the thought like, well, I should

(06:01):
have stuck with it a little longer. But my life
is very, very good and very fulfilling, and most of
it wouldn't have happened if I had stuck with it. So,
you know, you can't really play that game to any
kind of profitablelion.

Speaker 2 (06:12):
So it's hard. It's hard to say. Were your parents
supportive of it?

Speaker 1 (06:15):
Like I feel like, you know, I feel like i'd
be a supportive parent to somebody who was like going
to go live their dream and you know, go to
Hollywood and be an actor.

Speaker 2 (06:25):
But I'm not sure I would be.

Speaker 1 (06:26):
I'm you know, I'm born in the Soviet Union, where
we're taught like there's three professions you can do, you know, doctor, lawyer,
computer programmist, you know, like.

Speaker 3 (06:37):
My parents were. My parents were very supportive. Actually they
were realistic about it, and their realism proved prescient, Like
they were absolutely right. It was difficult, and when you
when you pursue that kind of thing, nobody really sugarcoats it. Ever.
In fact, you hear unlike when you're becoming a computer

(07:00):
programmer or a doctor or lawyer, they say, it's hard now,
but you're gonna you're gonna you're going to be glad
that you did all this hard work because the payoff
comes later. People are very clear with you when you're
trying to become an actor, like this is probably going
to be a miserable failure, and you you should get
ready for that. Of course, the nature of the thing

(07:21):
is that people, you know, charge blindly ahead without considering
the costs, and then they flame out, which is exactly
what happened to me. So my parents are very supportive.

Speaker 2 (07:29):
To answer your question, would you be if your kids
wanted to do that?

Speaker 3 (07:36):
You're asking the.

Speaker 2 (07:38):
Hard question to be easy, and then, you know, maybe.

Speaker 3 (07:41):
The fact is I don't have a choice. You have
to support your children. There's just there's no there's no choice.
You got to be realistic. I got to tell them
what what I do know having tried it and having failed.
I can't. I can't hold that from them. I have to.
I have to share that everybody's life is ultimately their
own life to to lead as they say see fits.

(08:03):
So my parents granted me that freedom, and I'm glad
they did. I would I would do the same for
my kids. I just hope they don't see this this
interview until they're old enough to understand the risks.

Speaker 2 (08:16):
What would you have done if Plan B, if being
a writer hadn't worked out?

Speaker 1 (08:20):
Because that's also, you know, a dream job, and it's
something that only a few people get to do. And
you know, when I told my parents I wanted to
be a writer when I was a kid. They were
basically like, no, you know, just pick something else.

Speaker 3 (08:33):
Yeah, I didn't have a plan b at all. I didn't.
Like I mentioned earlier, I didn't go to college. I
went to college out of high school, but I didn't
last I dropped out after one semester. I really had
no idea, you know that. That really is the sort
of the theme of my early life, Like, I had

(08:53):
no idea what I was doing. And if I hadn't
met my wife, who was a journalist at the time
that I met her. She was a sports reporter for
the New York Post, covering the Yankees at the height
of their success in the late nineties. She covered she
Giants in the Super Bowl, the Knicks. If I hadn't

(09:16):
met her, I don't think this thought would have even
occurred to me that it was something that I could do.
Her father was also a journalist. He wrote for many
years of the Daily News in New York and sort
of like meeting these people and seeing that there's a
life here that's possible, it was a big deal for me.
It was a big deal for me, and I got

(09:36):
a lot of encouragement from my father in law. I
got a lot of encouragement from my wife and her
whole family to pursue it. And you know, a lot
of times when you're sort of I was thirty, so
I wasn't so young, but I was still figuring it out.
You need to meet people, or you need to understand
that not every dream is totally out of reach. You know,

(10:00):
if you meet someone who's done it, yeah, suddenly becomes
tangible and you think I could do that too, And
you got to be a little bit you know, I was,
you know, I had tried to become an actor. So
I am a little bit like a sort of a
romantic night, you know, like I'll go charging into battle
if the cause is just so I just kept charging
at this and I think we got lucky. So far,

(10:22):
so good. As we say, love, what.

Speaker 2 (10:25):
Are you most proud of in your life?

Speaker 3 (10:27):
Okay, that's a difficult question. You know. The first thought
I have is that when I was in high school,
the let's just call them the popular kids where I
was from. For some reason, in my high school, we
called those people the proud crowd.

Speaker 2 (10:45):
So I kind of think close to proud boys.

Speaker 3 (10:48):
But okay, oh yeah, but nobody had had that thought
this was this was years and years ago. No that,
you know, the sort of the preppies with the popped
collars the eighties, you know, we called them the proud crowd.
So it has a sort of a pejorative association for me. So,
you know, I'm not so sure that it's good to

(11:09):
be walking around feeling proud of or too proud of
yourself all the time for things. You know, I suppose
if you press me, I would say I'm proud of
having having sort of turned turned the ship around when
I did, because if I hadn't, you know, in my

(11:31):
late twenties, if I hadn't met my wife and sort
of went back to college and started putting the pieces
together slowly, I would not have arrived in this beautiful
office where I'm sitting now. I wouldn't. I wouldn't have
had this life, in this career. I could have kept drifting,
you know, after the acting thing blew up, I was
sort of drifting. So I am sort of proud of
myself for realizing that something needed to be done and

(11:53):
taking the opportunity that was there to turn my life around.

Speaker 1 (11:56):
We're going to take a quick break and be right
back on the Carol Markowitz Show. It's interesting because the
whole conversation right now about getting married and having kids
and just even being in relationships, it's sort of seen
as something you're supposed to do after you figured out

(12:16):
everything career wise. And I have people on the show
all the time who say things like, you know, meeting
my spouse changed everything for me. Meeting my spouse was
the pivotal moment in my career. And yet it's seen
by the younger set. Maybe free expression can write some
pieces on this, but you know, it's seen by the
younger set is something you're supposed to have done already

(12:37):
in order to get married, and that's just not how
it goes.

Speaker 3 (12:41):
Yeah, I don't think that's how it goes at all.
That's certainly not how it went for me. I am
absolutely one of those people that it was the pivotal
moment of my life. It was the pivotal moment of
my career. As I've just said, it totally changed my
outlook and made me think that certain things were possible.
I took a big, a big roll of the dice

(13:03):
on me, you know, like on paper, I was not
a highly qualified I wasn't husband material let's just put
it that way. And so meeting her and taking the
leap was what's the best thing that ever happened to me.
And I highly encourage it. If anybody's on the fence,
go for it.

Speaker 2 (13:21):
Yeah, definitely.

Speaker 1 (13:22):
Have you seen the Nate Bergazzi clip the Comedian where
you know, he's super successful comedian, one of the highest
grossing comedians in America probably, I think he was number
one last year. But he said that when he met
his wife, he was a host in a restaurant and
his big dream was to be a server.

Speaker 2 (13:38):
And she was like, you keep dreaming that dream.

Speaker 1 (13:40):
And she was, you know, she took a giant chance
on this guy who you know, could have not turned
out to be anything, but ultimately owes a lot.

Speaker 2 (13:50):
Of it to her.

Speaker 3 (13:51):
Yeah, there's a lot of luck involved, too, Carol. I mean,
I hate I hate talking to people about, you know, relationships,
like meeting people. How did you meet your wife? You know,
it really was an incredible stroke of like like someone
was looking out for me, you know, and looking out
for both of us because we're a good match, you know,
like we're a perfect match. And what can I say,

(14:14):
lightning Lightning struck this guy. So I'm very lucky to
have been hit that way by a lightning bolt.

Speaker 2 (14:20):
That's awesome. I love to hear it described like that.
It is luck.

Speaker 1 (14:23):
Of course it's luck. I mean, you know, so are
so many things in life. Give us a five year
out prediction, and it could be about anything at all.

Speaker 3 (14:33):
Oh gosh, well, I suppose that I like to be optimistic,
and I like to I do believe that we are
like undefeatable as a nation. I think that we have
all the fundamentals and all the best things, all the

(14:55):
advantages that we've always had, we still have them. I
am worried that in the next five years that we
will have some kind of really really catastrophic economic they've
set back. I worry that that some seeds are being planted,

(15:17):
have been planted in the last few years, that are
going to bear really really bitter fruit eventually. The nature
of these things is that you know, you can't you know,
you can't predict them, other than to say that you know,
we will see a downturn. And we've gotten pretty good
at at at minimizing you know, the effects or the

(15:39):
duration of these kinds of recessions. But it's been a
long time since we had a really really bad depression.
And it's a little bit like you know, being sick,
getting sick from the common cold. Like you said, you
start saying to yourself every once in a while, jeez,
it's been about you know, it's been a long time
since I got really sick. And the many you have

(16:00):
that thought, it's like you're going to go down hard
in a week or two after that. And so lately
I've been having that thought. I mean, I hope it
doesn't happen, but history suggests that it will, and so yeah,
that's what I'm Unfortunately, that's what when I think five years,
I think we're going to get hit pretty hard here
at some point.

Speaker 1 (16:18):
Is that based on like our spending or you know, deficit,
or is it like an AI fear.

Speaker 3 (16:25):
Well, AI AI may actually be the savior here. I'm
no expert on it, but it it is a positive
development for our for the economy, for the for our economy,
for the for our national economy, and for the global economy.
I worry about trade, I worry about spending, I worry

(16:47):
about war. These are the kinds of things that could
that could really set us back. Having said that, I'm
an editor. I'm not an economist, and I don't I
don't pretend to be one.

Speaker 2 (16:57):
Wall Street Journal. You know the name, Yeah, that's right.

Speaker 3 (17:01):
There in the name. That's correct. Although I want to
point something out this. You didn't ask this, but something
that's on my mind. For some reason. I woke up
this morning in a fit about this. The newspaper is
called the Wall Street Journal, okay, And the people who
work here are journalists. We don't work on Wall Street.
We don't work for Wall Street, or we don't work

(17:23):
for banks. And that's true. But at this point, one
hundred and thirty five years into our publication's history, especially
on the editorial page, we stand for a particular philosophy
of free markets and free people. We believe in American
style capitalism, we believe in the freedom of the individual.

(17:46):
All of the things that you know used to be
a sort of a standard issue, standard regular Republican sort
of values, Republican with a capital are And so much
of the criticism that I get when we write things
is like, oh, it's so surprising that some that the
Wall Street Journal would would would care about you know, uh,

(18:09):
Ozzy Osbourne died and would write something about that. It's
so weird that the writers at the Wall Street Journal.
We did a big feature this weekend on the fourth
of July, asking people to tell us about the states
where they were from.

Speaker 2 (18:21):
Oh I saw that was great, that was really good.

Speaker 3 (18:23):
Thank you.

Speaker 2 (18:24):
Yeah.

Speaker 3 (18:24):
And a lot of people talked about the sort of
the the good hardworking people back home and in their
states and how they were raised in sort of a
blue collar environment, hardworking, faithful people, salt of the earth
kind of thing. And I see so many comments like, oh,
this is so crazy coming from the Wall Street Journal,
Like why would that be crazy? Why would why? You know,

(18:46):
the people who work here are not the former presidents
of JP Morgan. They don't work here, right. We write
for those people. We're trying to influence them. We want
them to read us, but we're not doing their didding,
you know, we don't. We don't work for them anyway.

Speaker 2 (19:04):
I like that.

Speaker 1 (19:04):
I like that explanation because I you know, it's interesting
because for a long time, when I was far younger,
I didn't read the Wall Street Journal because I read
the later editorial pages. James Toronto was, you know, my
daily read, the best of the web. I loved all
of that, but I didn't read the actual paper because
to me, I thought it was going to be all finance,

(19:25):
and I just didn't care about finance, and you know,
it wasn't up my alley. And then getting older, it's
the only newspaper. I shouldn't say this because I write
for the Post, but it's the only newspaper we subscribed
to in our house. So it is the you know,
it's I don't know if it always was, or maybe
maybe people are responding to that idea that it's not

(19:47):
a newspaper about everything, that's only a newspaper about finance.
I think a lot of people might just have that
in their heads from you know, their first time encountering
the newspaper.

Speaker 3 (19:59):
Yeah, stand that, and I may have at one time
when I was running around Hollywood with my credit card
and my cigarettes, I might have thought the same thing.

Speaker 1 (20:09):
But buying stuff on credit cards, as you're like, that
was a bad time for me.

Speaker 3 (20:14):
Yeah, it was bad actually, So God bless my parents
for supporting me through that because I needed some help
from time to time.

Speaker 2 (20:21):
So yeah, anyway, CONTRACT love this conversation.

Speaker 1 (20:25):
I actually love that explanation about what the Wall Street
Journal is isn't.

Speaker 2 (20:30):
I think that's super interesting.

Speaker 1 (20:32):
We're going to take a quick break and be right
back on the Carol Marcowitch Show. Leave us here with
your best tip for my listeners on how they can
improve their lives.

Speaker 3 (20:44):
Okay, the best advice I ever heard was this, do
the job that's in front of you, and the future
will take care of itself. This is something that I
think I've read this in a profile of Chris Christie.
This is something that his mother said to him once
and I have repeat I repeat it over and over

(21:05):
again to young people who are just starting out in
their career, to my own children, to myself. I say
it to myself frequently because we do have a tendency
to look ahead and to be very impatient about the future.
We want, we want to achieve everything that we're aiming
towards very if not very soon, then maybe even now.

(21:28):
And what life has taught me is that everything is
within your reach, but you just have to do the
job that's in front of you, and that if you
you know, there are other ways of putting this, don't
put the cart before the horse, and you know, all
that kind of stuff. If you do the job that's
in front of you. Inevitably, the future will take care
of itself. Maybe not on your preferred timetable, but on

(21:51):
a timetable you will get there. I have seen so
many people. I did it to myself. I've just told
you the whole story. I checked myself out of the
game in Hollywood. If I would have stayed, maybe, you know,
I like to think that I would have got there.
I entered this profession at pretty much close to the
bottom rung as a thirty something year old, and here

(22:12):
we are. You know, yeah, we made it. Look at us,
you know. So do the job that's in front of you.
Future will take care of yourself. That is one thing
you can do right now to improve your life.

Speaker 2 (22:23):
I love it.

Speaker 1 (22:23):
Do the job that's in front of you. He is
Matthew Hennessy. Check him out of Free Expression at the
Wall Street Journal. Thank you so much, Matthew for comming on.

Speaker 3 (22:30):
Thank you, Carol,

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