Anne Libera on How to Find Yourself Again Through Humor | EP 698

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Have a great day. Coming up next on Passion Struck.

A joke is a setup and a punchline, but when you equate comedy with jokes, you often equate comedy with some of the darker parts of comedy and the riskier parts of comedy.

And instead, the really central comedy that I love and that I think anybody can do is comedy of recognition.

If I share things about who I am and the way I approach the world, you are going to naturally be interested in them. And that's a central aspect of being funny.

So a lot of what I teach to talk about my students, I'm like, don't try to be funny. Which of course means trying to be funny means you're not going to be funny because there is no try.

There's only two.

Welcome to Passion Struck. I'm your host, John Miles.
This is the show where we explore the art of human flourishing and what it truly means to live like it matters.

Each week, I sit down with change makers, creators, scientists, and everyday heroes to decode the human experience and uncover the tools that help us lead with meaning, heal what hurts, and pursue the fullest expression of who we're capable of becoming.

Whether you're designing your future, developing as a leader, leader, or seeking deeper alignment in your life, this show is your invitation to grow with purpose and act with intention.

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Hi friends, welcome back to Passion Stock. I'm your host, John Miles.
This is episode 698, and we're continuing our December series, The Season of Becoming.

I've been saying this a lot lately, but it's true. People think December is the end of something.
For most of us, it's actually the moment before things start to shift.

It's the space where you feel yourself changing a little, even if you're not sure what comes next. On Tuesday, Susan Grau helped us look at becoming through the lens of grief and intuition.

Today, we're coming at it from a completely different angle. Creativity, humor, and the ability to let go of control.
And there's no better guide for that journey than today's guest.

Anne Libra, Director of Comedy Studies at the Second City, longtime collaborator and friend of Stephen Colbert, teacher to Amy Poehler, Jordan Peale, and Stephen Yoon, and author of the new book Funnier, A New Theory for the Practice of Comedy.

You may not think of comedy as a path to intentional living. but Anne reveals it's one of the most human.

Comedy helps us notice what we normally overlook, connect through the small truths we're afraid to say out loud, and move through difficulty with a little more grace.

At its heart, humor is a reminder that we're not alone and that who we are matters. That for me is why this conversation isn't about being funnier, it's actually about being freer.

Because improv is not about jokes, it's about identity. It teaches us to stop over-engineering our lives.
to listen deeply instead of performing.

It reveals what's true rather than trying to impress and helps us discover who we are as we emerge.

In today's episode, Anne and I explore why natural talent is a myth and comedy is actually learnable, how discovery unlocks authenticity, what Seinfeld teaches us about recognition and shared humanity, and how micro edits, those small adjustments we make throughout our days, can transform your voice, your confidence, and your identity.

Before we begin, if Passion Struck has impacted your life, please share this episode with someone who needs it, a friend, a co-worker, a family member.

And if you haven't already, I'd be incredibly grateful if you left a five-star rating and review on Apple's Podcast or Spotify.

It truly helps this movement grow and for new listeners to discover the show. Finally, December is also a perfect time to pour into the kids in your life.

If you want to help them grow up believing in their worth, then visit UMatter Luma to discover information about my upcoming children's book.

Now, let's step into the second chapter of the season of becoming with the brilliant Anne Liberoff.

Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating an intentional life. Now, let that journey begin.

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i am so excited to welcome ann libera to Passion Struck. Welcome, Anne.
How are you? I'm great. Thanks for having me on.
I'm really excited to be here. I'm going to open up with this question, Anne.

You say you're not natural funny, and I kind of feel the same way about myself. How did you end up devoting your career to comedy? I really backed into it in many ways.
And I

started really in improvisation. So it was as a performer, I was a director, and I got really interested in the Spolon-based improvisation that's taught at the Second City.

And that was the thing that opened me up

to ways in which I could be funny that were outside of jokes. Because I was never a person who told jokes.
I enjoyed comedy, but I didn't understand

the game of it. I wasn't a natural.
But what improvisation did for me was allowed me to find what was funny about me.

and find what

was funny about discovering things in my brain and that really made a shift for me and then the other thing that happened was that i started to realize that comedy wasn't that hard that i had bought into the idea that people are naturally funny or they're not and that there wasn't a way to get better at it and what i learned pretty quickly was that i could get better at it I was listening to a podcast that you did probably a year ago, and you were talking about a student in your course who had seen what line is it anyway, had wanted to join your course because he wanted to do that somewhere in his career.

But at first he was struggling because he was so anxious about getting everything right that he wasn't turning in his homework assignments, et cetera. I hope I got the backstory correct.
Yes.

Yeah, go.

But that's how I feel about bringing comedy, whether it was work, what I do now.

or other areas is I'm so afraid of how it will land that I don't take that leap to even use it.

What would you tell someone like me or that person who was in your class how to approach things differently?

Well, there's two things I think that are really important and one is connecting comedy to jokes as opposed to all the other ways that comedy can manifest itself.

Jokes are the riskiest form of comedy. They are hard to do, although they are simple in the sense that they're basically math equations.

A joke is a a setup and a punchline. But when you equate comedy with jokes, you often equate comedy with some of the darker parts of comedy and the riskier parts of comedy.

And instead, the really central comedy that I love and that I think anybody can do is comedy of recognition.

If I share things about who I am, and the way I approach the world, you are going to naturally be interested in them.

And that's a central aspect of being funny so a lot of what i teach to talk about my students i'm like don't try to be funny which of course means trying to be funny means you're not going to be funny because there is no try there's only two

but also be yourself

and be funny in the way that you are funny instead of trying to make yourself into something else.

And I think at a really simple level, that was the sort of aha thing for me as an improviser, discovering that when people laughed at the work i did they didn't laugh at the jokes i made they laughed at the things that i shared about myself that were true and also maybe a little uncomfortable and a little vulnerable that was the most powerful comedy that i could do Yes, well, I got my start in this area doing improv just like you.

And I did it a lot later in life, but I started with short form and then went to long form. And I realized that, especially when I was doing long form,

I guess when I first went into it, I was trying to think about what I was going to say even before I had the opportunity. And I found sometimes when you overthink things, it doesn't come out natural.

And so I learned you just have to really listen, which is the most important thing to what the other person is saying. So you don't miss the cues that they're giving you.

to then jump in and add on as you're saying a personal antidote that that often becomes funnier than you think it's going to be once it comes out.

Well, and there's such a great, one of my favorite improv concepts for comedy is this idea of discovery.

That if I am in my head thinking about, oh, what's this funny thing I'm going to do next? What's this interesting thing I'm going to say?

That I'm missing not only that moment of listening, as you described. but finding out something that I didn't know was going to be there before.

And as a performer, but also as an audience, it's that moment when something happens and we discover something together is a moment of true surprise as opposed to a joke moment of a reveal.

And for me, it is that

embrace of discovery, which

extends way beyond comedy. learning how to truly discover something with a collaborator as opposed to going in thinking what's going to happen,

is the essence of really good comedy, but it is also the essence of getting to something that is new,

is exciting, and that is going to connect with your audience because they're discovering it with you.

I love that. And your new book is titled Funnier.
Subtitle is A New Theory for the Practice of Comedy. And right on the front of it is an endorsement from Stephen Colbert.

And it turns out you've known Stephen for decades. How did the two of you meet? We met at Northwestern University in college.
He was in my acting class

and we worked on a scene together. I have a vivid memory of walking home from rehearsal together and he was always funny, but he was even more a talker.

Right. And he told, I remember walking through Evanston and having him tell me this really astonishing, complicated story about the way he looked at the world that was both funny and true and real.

And within a very short period of time, we were very dear friends.

We were roommates in college living in this big old house in Evanston that Stephen nicknamed Dis, which is the level of hell where the heretics burn in Dante.

And we have since then worked together as I've directed him. We've been in shows together and we are still very dear friends who communicate fairly regularly.

Yeah, I'm just going to follow up on that with something I've always wondered.

It's one thing for you to write for yourself for punchlines you're going to deliver, but how difficult is it to write for someone else? How well do you have to know in order to do that?

Well, this is an interesting thing because one of the things I talk about in the book is that we want to think about comedy in sort of five different components, one of which is jokes, one of which is physical comedy, which is also sound and cadence, right?

All the different ways that comedy exists in our bodies. It is story and narrative.
It is character and it is point of view.

And so when you're writing something for someone else, you are thinking both about their character, which is the way they present in whatever the thing you're making is.

So the writers I know who write for Stephen, who wrote for him on the Colbert Rapport, were writing for the character that Stephen Colbert played as Stephen Colbert.

But many of those same writers are writing for him on the late show, and they're no longer writing for that character, but both the character on the Colbert Rapport and the character on the late show have a similar point of view.

And this is something that I think about Stephen and have noticed in our work together is that Stephen's really interested in the way we use language

to talk about the things that we believe to be true.

And I was thinking at one point in college, my sister was a math major, and he called her and said, I really, I have a question for you. I have a question for you.

If I cut a loaf of bread in half, do I have two bread?

And he was like, Stephen, I think that's a semantics question, not a math question.

But that's his, he is fascinated by how we use language and what we mean when we say certain things and how we twist our meaning.

And so if you're writing for Stephen, you want to keep that idea of his point of view in mind. You're looking for the ideas around how people say what they're saying.

So you're writing not just for the character and you're not just writing jokes, you're writing for that point of view.

Well, thank you for sharing that.

One thing I really liked when I was reading the book is that you have these different anecdotes that you bring out, like the 25 people rule, the Letterman temperature note.

And talking about what you just were going into with Stephen Cober,

you note that we laugh when we're physically closer to people. And even, which sounds counterintuitive to me, a colder room helps.

How do you design not only what we were just talking about, but also for the social physics of laughter, things like room size, audience density, running order, things like that. Well, okay.

So I'm going to actually get into the meat of my theory because the theory really is effective both for creating comedy, but also for revising comedy, which includes things like that, those physics.

Okay.

I believe that when we create comedy, we are looking at three primary variables. And the first thing is recognition.

Recognition, sometimes you can get a laugh in recognition alone. If somebody does something that you've seen them do before, one of the reasons our favorite comedians are our favorites is because

they do things that we recognize and see. We love when a comedian uses a catchphrase because we recognize it.
We love characters because often they remind us of people that we have seen before.

There's way more than that. We can get into this more.
But the second element then is pain.

There isn't comedy without a little bit of discomfort, a little bit of pain. And that speaks to what you're talking about in terms of being a little bit cold.

A lot of comedy theaters keep their temperature at just a little bit under

what would normally be a comfortable seat place to sit in because they know that just a little bit of discomfort connected with maybe a simple recognition joke is going to make the audience laugh harder.

But you're always, as a comedian, then playing with: okay, how uncomfortable is my audience?

So, if my audience is coming in with a lot of discomfort, maybe because something terrible happened to the news, maybe because they actually even just had, it's been snowing out, so they're coming into a room in a slightly uncomfortable place.

I'm going to do comedy or I'm going to revise my comedy in that moment to make it

more recognizable and simpler and easy for them by giving them a little bit of safety and distance. So I'm always sort of playing with these three elements of recognition, of pain, and distance.

And that's true whether I'm doing something highly satiric or whether I'm even doing a really simple one-liner in a comedy club as a stand-up.

playing with how comfortable is my audience.

So if I have an audience that is very nervous, because Second City is coming to their town and all they know of Second City is that it's left-wing and scary,

my cast, and I direct a cast that actually tours all over the country, are going to make sure we give them some things at the beginning of the show that are really recognizable to them, that are really easy for them to connect with us with, and they're going to start to trust us.

And let me,

yeah, go ahead. Yeah, well, I was going to just ask a follow-up to this, maybe to make it even more real for the audience.

Is there a concrete moment when you, or maybe there's a scene that people might recognize where the people in it deliberately turned each dial recognition, pain, and distance to make a joke or a scene work better?

Well, okay, so I'm going to use an example that I use in my book, which is I was working with Jordan Clepper, who now does the daily show,

and he was a student, and then we worked on a show together. And we had a premise that was very painful.

And

he was smart in going, okay, this is a painful premise, but I can see where all the elements are.

And the premise was he was a very successful doctor who had just been and had cured cancer, was a really good guy, and he'd just been nominated to be the vice presidential candidate for the United States.

And it was a press conference, and they were asking him questions. And suddenly, in the middle of it, he says that he really doesn't like Anne Frank.

In fact, he hates her. And very dark, right? Why would you hate someone, a Holocaust victim? And so what we did is we played with that premise to make it safer.
So we kept that pain.

And that pain is useful, right? Because people that we know say scary things.

Right. We all have had that experience where someone we really says something that we're like, uh

Also, we all have issues with teenage girls and find them occasionally annoying. So, there's a lot of interesting pain in that.

But then we made him not hate her for the reasons that Hitler hated her, but he hated her for the reasons that you hate 13-year-old girls. So, we made it safer, right? We made it simpler.

So, we've got that recognition and pain in element, but then we also

made the scene about the press corps who couldn't believe he was saying this and were desperately trying.

So the audience was not, in that moment, was not identifying with the character who said this thing. They were identifying with press corps who was just trying to make it okay for him.

Trying to make it that so that he was not someone who said this thing. And so again, we're playing with,

and in multiple different ways. The whole thing would not have worked if it hadn't been for Jordan Clepper's persona,

which is actually in life really affable. And there's something about him that makes you almost immediately go, okay, he's okay.

Yes. Which allows him to say things that are darker.
It's also true. That sketch is not a sketch that I would bring to an audience in an area where there had been, say, violence against Jews.

You have to be

aware of how the world that we're in

creates conditions that make things funnier or less funny.

I'm going to say, as somebody who's worked at the Second City now for a very long time, that in the 90s, when, as a rule, our audiences felt pretty safe.

They felt like the world was pretty warm and helpful. And while yes, there were things going on, they felt pretty comfortable in seeing us do what we would refer to as edgy comedy.
darker comedy.

Now, our audiences are in a world that is very chaotic,

and they have a much stronger reaction to what we'd refer to as edgy comedy. We spend a lot more time in our shows now, really

spending time on just like comedy that's about people and

relationships, and they are very uncomfortable with political comedy or comedy that addresses some of the things that are happening in the world that are much darker.

And so, we're always really aware of how those things shift over time and then geographically and all those other places too.

I hope you've been enjoying my conversation with Anne Libra. Before we continue, I want to pause on something Anne shared, that identity doesn't change through force.
It changes through discovery.

When we stop trying to perform our lives, we finally begin to live them.

If you want to dive deeper into the science and practice of becoming, things like identity evolution, microgains, behavioral courage, and emotional resilience, Then join me on my Substack community at theignitedlife.net.

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You're listening to Passion Struck on the Passion Struck Network. Now, back to my conversation with Anne Libera.

Yeah, so I want to ask a follow-on to this because I think it's important. I think everyone today would, if you we're living in a time of decisiveness, would agree with you.
Yeah.

But you argue truth and comedy

to what you were just saying before isn't about facts. It's about recognition or truthfulness.

So, how do you coach students and maybe a public speaker to find

recognition for an audience that might not share their facts, but only their feelings?

So, I think one of the simplest ways that you can share recognition is to share things that are true for you in really simple little ways i worked with the second city and the university of chicago on a program called the second science project where we used insights from behavioral science to help people actually practice being better communicators

And one of the exercises that we created is really applied comedy, where we had had people talk about something pretty boring, grocery shopping.

And we had them talk for about a minute, what do people do when they go grocery shopping?

And then we say, okay, we've talked for about a minute about what people do. Now talk about what you do.
How do you approach grocery shopping? And I don't know about you. I'm a foodie.

I go to like seven different stores.

Like I want to get my fruits from one store and actually my vegetables from another store. So I have this very specific way way I go grocery shopping that tells you a lot about me and the way I am.

And what we discovered over and over again, that choosing to share this sort of little bit of semi-vulnerable truth.

So it doesn't showcase you in a terrible light, but it doesn't show, you don't have to do the sort of put down jokes that stand-up comedians do.

You just have to share something that's really true and maybe a little weird about you.

And your audience will find it funny because they feel like they're recognizing something in your brain that they didn't really know was there.

And so the more of that little tiny detail, when we just throw in something that is just recognizable in a way that humans are recognizable, but maybe not what we assume is recognizable.

Oh, everybody knows about airplanes. Maybe that's actually a good example: is there's the classic old Jerry Seinfeld routine where he did talked about going through the airport.

Very recognizable to everybody, but what's recognizable about the way he tells it is his obsession with the little minutiae of the airport.

Why is this exactly like this? And that's the comedy of it. But it's also, again, to speak to things that we can do in our real lives.

sharing just a little bit

of

semi-vulnerable detail about who you are and what matters to you, and your little bits of flaw, not your, you know, deepest, darkest fears. Your, you're like,

does anybody else have the thing where it feels like the minute they put their glasses on, it's immediately covered in schmutz?

Do I touch my glasses? What is happening? That is a constant thing for me. It is true, but it's something that I'm not going to normally share, and that

audiences and friends and real people will recognize as being just a little bit vulnerable.

And they will make that connection through that pain of vulnerability with the understanding that it's really recognizable and true. And it's safe.
I am telling you something about myself.

I am sharing something with you. There's no danger that you're going to turn that against me.
And I'm being a little bit vulnerable.

Since you just brought up Seinfeld, I want to stick there because in the book, you you share one of Seinfeld's best episodes, I think.

And it was the one that I think all of us can relate to when you're trying to go to a restaurant and there's a huge weight. Yes.
And that weight can be agonizing.

And they turned a whole episode into this. What worked so well about that scene that so many people could relate to?

Well, okay, so there's some really interesting ways they play with time in that episode. And also surprise, you don't see people on TV wait for tables.

Right?

So there's a really simple pain of incongruity there, right?

And I think one of the things that Seinfeld did across the board really brilliantly is show things that people knew from their lives, but had never seen in their entertainment.

Right? The things that they're, and one of those is waiting for a table. Nobody in TV waits for tables, but get sat immediately.
And then

genuinely in that episode, making it the length that you actually wait for a table, which is the length of a television episode. So they're playing with time in a really interesting way.

And then they're also playing with, this is the fun of that episode too, is the way in which people waste time.

people

try to make time work for them. So there's all these little tiny recognitions recognitions and pain points that we've all experienced, but we've never seen it really specifically

shown out in the world. And so there's that great moment, which I think is one of my favorite laughs of all time, where an audience goes,

you too?

And that's the laugh. The laugh is then just going, oh, I do that.

I didn't know. I thought that was just me in my own little brain.

Right? And then, of of course, because the Seinfeld characters are willing to do the most uncomfortable things, and they are the worst version of ourselves.

They are bad instincts that we keep ourselves from doing, but then we get to see them play that out, which is both really appealing and because it's what we thought we wanted to do.

But, and that gives us distance, though, right? We would never really do that, but because they're bad people and they do it, we get to enjoy seeing that play out. I loved it.

What phenomenal writing that series had from start to end. Well, and again, so specific.

I think one of the, this is a really minor, and this is absolutely a comedy professor thing, which is if you watch most sitcoms,

the location is generic.

There's no real food in their fridge. Their couch looks like any one of a thousand couches.
What Seinfeld did was he made, they made that space very specific.

They had Snapple in their fridge, which then of course became product placement, but whatever. But this idea of almost because we, as we're human animals, we're fascinated by other people.

And so to have real things happen in that show, real, and then real elements, that couch is the couch that he bought for this reason and ended up in this way.

And maybe it smells weird, just like your couch.

And I think that all of those, and again, those are really simple little details that allow a level of humor and comedy into real life that you can do in your everyday life.

Yeah, I'm going to stick to Sonic one more time.

So I've heard Jerry talk about this. I've heard Steve Martin talk about this, that prior to them.

going on tour or maybe even going on a late night show,

they go into comedy clubs on the regular and just practice jokes to understand

what you talk about in the book, recognition.

And I'm going to tie this now to one of the things that a lot of researchers used to do was in the lab research, but I think great researchers do field research.

And in the book, you talk about the cruise ship story as a way. to bring out how do you figure out recognition versus not enough recognition.

What did that experience teach you about how to understand what an audience wants versus what they don't?

Well, so you have to take into account not just what's happening in the room, but what's happening in the world.

And this is something that I talk to my students about in general, about the industries, the way people watch their comedy, where they are and why they're there.

And so one of the things that when, so Second City had a contract with Norwegian Cruise Lines and we were on six or seven different ships for about 15 years. But this specific ship was in Europe.

And even more than that, this specific ship was an audience that were not primarily English speakers as their first language. They understood English, but English was not their first language.

They were primarily German and Spanish speakers. So we had originally gone out doing a show that was all silent scenes.
thinking that that would be great.

However, a lot of our silent scenes that we were working with were also sexual scenes. Oh my.

And what we forgot was one of the main things about cruises is that people go on cruises to not have a bad time.

So you go on a cruise, there's a lot of food, but it's not very highly spiced.

It's not specific, but it's going to be good enough.

And people lots of times, this is why big families go on cruises together, because you know that while maybe no one in that group is going to have a peak experience, everyone's going to be okay.

They're going to find something.

But what that meant was,

and big one on cruises, because people go to not have a bad time, they are very

picky when something happens that might offend them, might make them uncomfortable.

So going in, we're like, okay, so we can't use a lot of the sort of discomfort comedy that we might use in our theaters. We can't do

something that is potentially offensive.

And I always love that thing because there's a lot of people who be like, it wasn't offensive to me, but it might be offensive to someone else, and therefore I feel negative about it.

So, we're really having to jump through both of those hoops.

But what we realized was that the most powerful thing that we could do was to do jokes about being on cruise ship. And even more than that, we didn't have to tell jokes.

We literally just had to show the cast on stage, wearing life vests, doing what people had done two days before.

and the audience is yes huge applause i was there i know the thing the cabins are really small yes

and it's i think

that idea that we have seen something and we don't one of the things that i think we for we forget is how much of what we see yeah other people see

And we somehow think that we're traveling alone in our giant pet org.

And so that moment of

you saw the thing I saw.

You experienced the thing I experienced is both a huge surprise, which is a kind of pain, right? Surprise is a kind of pain. I did not expect you to experience this thing.

At the same time, as it's so close to me that it makes me just so excited that someone else, it's a moment of connection. It's a moment of recognition.
So I've got that surprise and recognition.

And then I've got, I'm in a safe place because I know that you're taking care of me.

And

again, it's such a little thing and would seem so obvious. And yet it is one of the strongest laughs we get.
And in comedy, you can get that laugh just by saying the name of a town.

And we always talk about in business conferences, we have what we call the Bob from Accounting effect. Yes.

Which is if we do, if we're doing a show for or a keynote for a business, we mention someone who is probably at a slightly lower level but everybody in the business knows them and we just say their name the audience gets an immediate burst of laughter

because

they didn't know we knew

is the surprise but they know and that idea

and

That laugh builds because somehow we sometimes think, again, we're all in our own little heads. When someone else sees the same things we do in the same way, that's that tremendous,

that's this tremendous burst of good brain chemicals

of connection.

And that connection is the place where that initial laughter resides. And it's some of the, I want to say it's some of the safest laughter.

If you are somebody who doesn't think of yourself as comedic or think of yourself as a joke teller, you're much better off sharing just a little something true that everybody else shares than telling a joke that you've memorized.

Man, I love that. So I want to move on to something that you call thick versus thin comedy.
Yes. And especially why both matter.

So the background on this is in the book, you reframe jokes as thin versus maybe you can go into that rather than high versus low.

Yeah, okay. Yeah, go ahead.
Yeah, no, so maybe you can explain it through that lens. Okay.

I think it's one, I'm going to talk about high versus low, first of all, just for one brief second, because I think that traditionally what we think of as low comedy, which is comedy of the body,

has been frowned on. And if you look at the comedy that is seen as valuable, frequently it's not comedy of the body.

It is comedy of mind and of the words and all of that, which truly is how I was taught. It's certainly what I thought.
But the fact of the matter is we all have bodies.

We all have experienced all the things that bodies do. It is simple.
So it is thin,

right?

So thin comedy is not just comedy of the body. It's not just comedy about farting, say, although multiple farting can be funnier.

It's this idea that you'll get that initial laugh on thin comedy, but then to hear it again, it may not make you laugh again.

Thick comedy is when we're not just doing the fart joke, but we're also doing the fart joke about maybe a character and who is the person who is farting. I can't believe this is my life.

Sometimes I have to have long conversations with students about, now, who is farting?

Why should they fart more? But we are bringing in, when we start to bring in multiple elements, and it can be as simple as a character and so all of a sudden we're commenting on people who

i'm going to keep talking about farting people who are allowed to fart

and people who aren't

we're talking about the ways in which and then all of a sudden we can add like a political point of view who are the people who are allowed to have feelings

who are the people who are not allowed to be human and fart

What is our belief structure? So all of a sudden that joke that's still at that very low level, and also fart is a funny word.

And I just want to add that because there is just sometimes there are words that are funnier.

They use actually, interestingly, a lot of the words that we think of as funnier, and you think of George Carlin's seven words you can't say on television, they often also use Lud Taboo words, use T sounds and F sounds and K sounds.

So, if you want to be funnier, you use those sounds. But you add these various levels.

So, you can have something that's a very thick joke that has point of view, that has, that's talking about a character that is building off of something that's true in the world.

It may not actually get a hard laugh because there's so much there to chew on, but you may find it funnier the more you watch and listen to it and

or read it. right

but there are certain things that you could count on an audience immediately laughing at and that's that thin joke that is something that everybody responds to and i think that's another piece for those of us who just want to use comedy and humor in our everyday lives is recognizing that we can use something that's maybe a little bit thicker and is not going that's going to cause people to have a little bit more of a reaction to, but it's not maybe going to get that initial laugh from everybody.

Yeah. And maybe for the listeners, is there there a thin gag that you keep in your pocket or maybe we should consider keeping in our pocket to reset a room before we deliver heavy material?

I think one of the thinnest gags and easiest ones, particularly in a space where you're with a group of people, is to simply call out something that just happened.

Right. So would that be like a thick callback or would that be a thin? That's actually just thin.
You're just, you're saying you're like a thin callback is just repeating something that just happened.

But a group that's in a room where something, well, John just left.

And it can be as simple as that,

right? Oh, we're all in the same place. Now we're going to move forward.
So it's not a joke necessarily. Does that make sense? It is truly just restating something that

we all saw or experienced.

In fact, one of the things that's really powerful that comedians do all the time is

just recognize a moment of discomfort. Something happened that made the group uncomfortable.
And we simply say, well, that was uncomfortable.

Right.

And that gets a laugh and it releases the tension that people were feeling. And it also creates coherence among the group because I am recognizing a thing that we all saw or heard.

and letting and everybody goes oh yes okay everybody saw that and feels the same way i do and so we come back together and it can be as simple as that we certainly at second city we can be a little bit tougher because it's our house and if somebody does something that's a little silly we'll call it out because we have a little bit of control over making sure that they feel good about that if we're in a business meeting we're not going to do that

so something i talk a lot about on this show is micro choices Something in the book you talk about is micro edits.

And I'm going to go back to high school here because I had this English teacher who constantly was up our butts about grammar. You got to get your grammar right.
If you don't get your grammar right,

people aren't going to understand what you're saying.

And you say that often a flat joke is just a grammar or like a logic problem. Yes.

What is the best way to test that and to rewrite it?

So the very first couple of things, and when you're talking about, okay, I just wrote a joke. I wrote something in a joke structure.
I'm not even sure if it's funny, but I've got it.

The very first thing in a joke is that the last is that the reveal should come as late as possible.

So if I'm looking at a joke that one of my students has written, I'm going to say, does the reveal happen at the very end of the joke?

That's the first and simplest thing. The second thing I'm going to say is, did you use too many words? How many words can you cut from that joke and still have it work?

I'm going to look at whether the words you're using are

clear or if there's another better word, something that's going to be more specific, that's going to be closer to the idea that you had.

And again, a lot of times a joke is a setup that I'm going to define jokes. A joke, what a joke does is it sets up an expectation and it does something that reverses that expectation.

So we can think of a joke as a math problem, which always is very hard for my comedy majors who did not do well in math. And then I'm like, well, this is what this is.
It is, it's logic.

So you're saying, okay, if there's two halves, the setup makes you expect

that we're talking about a man. I'm making up an imaginary joke that I don't even know if it exists.

But the setup said that you're talking about a man and you find out in the in the payoff that you're not talking about a man, you're talking about a dog.

Then you want to make sure that whatever is in the setup is equally true about men and dogs. Right.
So that where it works, but there's a balance there. Let's use an actual joke.

There's the worst thing when you have, you're like, I know no, I know so many jokes. Okay, here.
This is a Phyllis Diller joke. By the way, Phyllis Diller, when she died, left her,

she had an entire office full of filing cabinets, full of wine liners,

some kind of over a million jokes that she left to the Smithsonian.

And you can go and see all of Phyllis Diller's jokes at the Smithsonian.

But light travels faster than sound, which is why some people seem bright until they speak.

So the setup is true.

Right?

Science says light travels faster than sound.

The punchline, the reveal, is

using the word light in a different way.

Right? So we say, now we say, because some people seem bright. So bright is a different meaning until they speak.
It's math.

It's a kind of grammar math, but it is about making sure that these, that all the elements basically balance each other and work together.

And so you're tricking someone, but you're tricking them with something that is smart and that at the end pays off in some way.

So I want to zoom out here for a second.

What's a moment from Wait, Don't Tell Me or your WGN theater critic date that still teaches you something about timing or audience expectation?

Oh, interesting. So they're actually two very different experiences.

And I think one of the things that was so interesting about writing for Wait, Wait, Don't Tell Me, which I did only for a fairly brief period of time, I should say, well, Peter was on paternity leave,

is

how

how an audience that is coming to that show

is different from a regular audience that is looking for just laughter the npr audience and specifically the weight audience is looking for things that are

that they

recognize and allows them to feel smart So you're always coming the news for what are the things that people are going to be just a little bit interested in, as well as the straight-up jokes off of politics?

And that's its own weird element of trying to build those two things together, if that makes sense.

I think one of the things for myself as somebody who has worked as a theater critic too, and that was a very different

on GN was a very different situation where I was on with Roy Leonard, who was actually my father-in-law, who was a well-known theater critic who really liked shows like Phantom of the Opera and other sort of really traditional theater things.

And my job as his co-critic was to play off of that, to understand that I was playing for an audience that really would go see Les Miz seven times if given the opportunity.

But that my job was to play Devil's Advocate.

and make them feel like they've learned something about the theater scene in Chicago or the sort of edges of the theater scene in Chicago, and that they may or may not be coming to those shows, but that I was giving them my point of view, which was a different point of view than they knew that was interesting to them.

And I think, again, point of view, recognizing that your audience is interested in how your brain works.

And we don't actually get that opportunity very often to feel, oh, I get this other person's brain, where they are genuinely this idea of,

so social scientists will tell you that we're very bad at perspective taking

right we're very bad at actually knowing what other people are what other people are thinking we think we're good at it but we're bad at it one of the things i think that comedy does uh and the tools of humor and comedy is that they do what they allow you to do something that i like to think of as perspective giving that

if i am and it's not always comedic but i'm using the tools of comedy i'm using the tools of recognition of pain of psychological distance to make you see the world

in a way that I see it. To allow you to have that feeling of, oh,

I'm connected to that person. I feel like I know them.

And if there's one thing that working in comedy for all this time has really taught me and teaching comedy has really taught me is that I can choose

to share those those little moments of recognition, those moments of pain, and make it safe for my audience. And they will feel like they've connected with my brain to brain.

And that is, I think, the thing that we're all looking for, both in our comedy and in our lives.

Well, I'm going to do a follow-up on that because you touched on durable brain and point of view in that.

last component we just talked through. You have taught some really famous people, Amy Poehler, Jordan Peale, Stephen Yoon, just to name drop.

What's a shared early tell that someone is discovering a durable point of view and not just a hot bit?

If you analyzed like what those

stars get right, so there's well, and I will say this: that like Amy in my class was funny and on it from moment one. I can only say that I would watch her and go, Oh, you're so good.

But I think the thing that I see as people grow as comedians is you start to see them discover

what is funny about them, meaning not just what they think, but the way in which other people respond to what they think. And that can take a little bit of time, that takes time.

One of the things that I think is true about Steven Yoon, which is interesting in particular, he's very funny, by the way, and he doesn't get an opportunity to do that very often.

But it's part of of what also makes him a really astonishing actor is that he's able to, you're able to see him think in character.

You see what his character is thinking, and that is the thing that people really respond to. So it's, but I would say over and over again, the really successful comedians that I've worked with tend to

find that moment where they are willing to show to the audience the thing that is most fun for them and then find those moments when the audience is in agreement.

So it is, I don't want to say it's trial and error because I think there's an aspect of

vulnerability

there. And you think of somebody like Tim Robinson, who in many ways seems not vulnerable at all, except his characters are intensely anxious.

My son, who's 28 and still can't drive a car, loves the, loves the sketch where Robinson's character is just behind the wheel in the parking lot so afraid of driving that

that willingness to open up your chest a little bit and go here's this very scared beating heart and then feel that moment when the audience is like oh yeah me too

and then to continue to build on that in ways that are unique to you is the key. It is, again, I'm going to come back to pain.

I do think that the best comedians find ways of sharing

the pain

in a way that allows other people to say, oh, I've got that pain too.

Yeah. I was interviewing Bo Eastman, who you might not know who he is.
He used to be a professional football player, but now is one of the biggest. public speakers in the world.

He talks in front of tens of thousands of people. And we were talking about Tom Brady.
And he said, no one wants to

Tom tell his story of how he won seven Super Bowls. They want to hear about his time at Michigan when he almost quit football altogether and really dive into that story of how did he turn it around.

And I think that's what you're saying. We laugh when other people share.
Also, we laugh when other people share their pain because it is such a relief,

right?

Oh, you see this too?

Oh, you had this too?

Oh, and that

connection

that discovery

through shared pain is i think what the best comedians and sometimes that sometimes it can be for evil right i'm not saying that some sometimes it can be oh you and i both think that those people are weird right

but that connection through shared pain is the place that a really great comic point of view gets born.

And if a listener wants to be funnier by Friday,

I'm going to give you a way to make this practical. Say we have a listener who's giving a keynote next week or they've got an important presentation that they have to make at their company.

Is there an exercise that you could give to make something that they have to share both safer and funnier for that audience?

I would look through what I'm presenting. for what are the places where I can personalize.

So I can, again, recognition. What are the places that I have a personal, specific reaction to or little piece of, again, little pain, right?

Where I have made a mistake,

where I have a personal little tiny pain point, a pet peeve.

And find a place to just share that, not as, aren't we all like this? But as, let me, I'm going to open up the little window to my brain and give you, I'm going to, I'm an expert.

I know all this stuff. But let me also tell you that I have this little thing that gets me.
I have this little thing that is hard for me.

And find those little places where, and it doesn't, I should even say, it can simply be,

let me, let me, I'm going to give you a little bit of window into something that happened to me today.

And it's not necessarily a lesson. It's that I'm going to show you that I'm human too.
And the more specific and the more weird that it feels like to you,

but isn't about them. It's about you sharing something that's just a little bit weird about you.
That moment will break open a connection.

I think that's really important because connection is the number one thing that you have to do, whether it's improv, you're trying to sell something to the board of directors or whatever it is.

If they're not connecting with your message and leaning into it, you're never going to get them to move forward with it based on my experience. And I want to say this.

Don't be afraid to share something that you think you're the only one who notices it.

I think sometimes our biggest mistake is assuming that there's stuff that everybody knows and stuff that only I know.

But if you can share a little tiny thing that only you know that you think other people might know, that's going to be the place where they're really going to connect. Awesome.

Well, one last question for you: improv versus stand-up. If you only had one you could teach for the rest of your career, which one would you pick and why? Improv.
I love jokes.

For somebody who's worked in comedy, I'm a very left, I'm a math brain person, and jokes are logic. So I'm really good at fixing jokes, and that's one of my superpowers.
But

improvisation for me is connection and discovery

and ensemble and that idea that I'm going to make something with you that's different from something I'm going to make by myself.

One of my favorite lines from Sheldon Patinkin, who is one of my mentors at Second City.

And somebody had said, is it true that an ensemble is only as good as its weakest member? And he said,

An ensemble is only as good as its ability to support its weakest member, and that weakest member can be any one of us at any time.

And so for me, that as an ethos

is what keeps me coming back to comedy and improv.

Love it.

And listener who's out there wants to learn more about you and your work, what you teach, everything else, where's the best place for them to go?

I would go to secondcity.com and you can email me from there.

Awesome.

I'm going to just plug Carrie's show as well because I love that Second City podcast that he does. Kelly Stroke? Getting to Yes And.
Yes. Yes.
That is my husband. Oh,

I didn't put two and two together. Oh, yeah.

Yes.

In fact, he talks about me all the time. Anybody who listened to me.
Now I know. I love that show.
He does a great job interviewing people. Yes.
So, yes. Getting to Yes And Kelly Leonard.

Awesome.

How, how could I be so

I do all this research and I miss this one. You just go back.
You'll hear all about me.

Well, Anne, thank you so much for joining us. It was an honor to have you.
Thanks so much, John. That's a wrap on today's conversation with Ann Libera.

I hope it left you feeling a little lighter and a little more open to the idea that becoming doesn't always require force. Sometimes it's just noticing that matters most.

Here are a few reminders to carry with you. First, you don't have to be naturally funny.
Humor is a skill and a way of seeing.

Second, the smallest honest detail about who you are can create the deepest connection. And third, when you stop performing and start revealing, you give others permission to do the same.

If this episode resonated with you, please take 30 seconds to leave a five-star review on Apple Podcasts or Spotify.

And if you want to go deeper, then join me at theignitedlife.net, my sub stack for weekly insights. or workbooks for every single episode and reflections.

You can subscribe to Passion Struck on our YouTube channels at John John R. Miles and Passion Struck Clips for full episodes and bonus content.

And visit startmattering.com to explore our store where you'll find meaningful gifts that remind you and the people you love that you matter.

Next week, we continue our series, The Season of Becoming, and we shift from improvisation to high-stakes leadership.

My guest is Brent Gleason, former Navy SEAL and best-selling author of the new book, All In.

We explore what it truly takes to commit, transform, and lead with absolute clarity when everything is on the line.

If I had to pick one thing, and I think a lot of veterans would resonate with this, is

your experiences in the military, especially if you've had any experience downrange, is about perspective and really looking at the world and your life and the impact you want to have through a completely different lens.

And you have a greater degree of discipline then because of that to eliminate things from your life.

that really are either adding no value or are blockages and threats to living a meaningful, purpose-driven life that'll have a positive impact on others.

Until then, remember, becoming isn't scripted, it's discovered. I'm John Miles.
You've been passion struck. Now go start the revolution.

At Arizona State University, we're bringing world-class education from our globally acclaimed faculty to you. Earn your degree from the nation's most innovative university online.

That's a degree better. Learn more at asuonline.asu.edu.

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