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

What if becoming who you want to be has less to do with control and more to do with letting go? In this insightful episode of Passion Struck, John R. Miles sits down with Anne Libera, longtime Second City director, educator, and author of Funnier: A New Theory for the Practice of Comedy. Together, they explore how improvisation offers a powerful model for personal growth, creativity, and identity transformation. Anne’s work blends comedy, psychology, and human behavior. Drawing from decades at The Second City working with performers such as Stephen Colbert, Amy Poehler, Tim Meadows, and Jordan Peele, she reveals that improv is not ultimately about being funny. It is about presence, awareness, emotional flexibility, and learning to respond to life as it actually is, rather than how you wish it would be. This episode continues our December series, The Season of Becoming. It explores who we are in the moments in between when one version of our life is fading, and another has not yet taken shape. Get the full episode show notes here: https://passionstruck.com/life-lessons-from-improv/Listen, Watch, and Go DeeperAll episode links are gathered here, including my books You Matter, Luma, and Passion Struck, The Ignited Life Substack, YouTube channels, and the Start Mattering apparel store:https://linktr.ee/John_R_MilesDownload the Companion WorkbookThe Becoming Workbook: How to Let Go of Old Scripts and Step Into the Next Version of YourselfIncludes reflection prompts, identity exercises, and tools for loosening rigid thinking and building creative flexibility.https://www.theignitedlife.net/p/improv-skills-for-personal-growthIn this episode, you will learn:Why improvisation is not about comedy. It is about attention, awareness, and responding to realityHow humor helps us navigate discomfort, uncertainty, and identity changeWhy trying to control the scene often makes life harderHow to practice Yes, and in real relationshipsWhy reinvention requires play, curiosity, and emotional riskThe psychology behind why we cling to scripts that no longer fitHow to use comedic tools to expand your sense of identity and possibilityWhy becoming is not reinvention. It is responsivenessHow to build creative confidence even if you do not consider yourself funnySupport the MovementEveryone deserves to feel seen, valued, and like they matter. Show it. Wear it. Live it.https://StartMattering.comDisclaimerThe Passion Struck podcast is for educational and entertainment purposes only. The views and opinions expressed by guests are their own and do not necessarily reflect those of Passion Struck or its affiliates. This podcast is not a substitute for professional advice, diagnosis, or treatment from a licensed physician, therapist, or other qualified professional. Connect with John Pre-Order The Mattering Effect: https://matteringeffect.com/Book John to Speak: https://johnrmiles.com/speaking/Keynotes, books, podcast, and resources: https://linktr.ee/John_R_MilesChildren’s Book — You Matter, Luma: https://youmatterluma.com/Substack:

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Hello, I'm Chris Richards, general manager at Safran Volkswagen Richmond. I'm here to announce an exciting new program that I want you to listen to. Here's my friend Happy. Hi, I'm Happy Harry Turner, special finance manager at SafranCredit.com. If you're in an open Chapter 13 bankruptcy, recently filed a Chapter 7, or you've been turned down because of credit challenges, don't give up. For nearly 30 years, I've helped people get reliable transportation when others said no. Visit SafranCredit.com. Remember, I'm not happy unless you are.

• 0:30John R. Miles?

  Coming up next on Passion Struck.

• 0:32Speaker 02

  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 do.

• 1:16John R. Miles?

  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 changemakers, 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, or seeking deeper alignment in your life, this show is your invitation to grow with purpose and act with intention. Because the secret to a life of deep purpose, connection, and impact is choosing to live like you matter.

• 2:05John R. Miles?

  Hi friends, welcome back to Passion Struck. 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,

• 2:48John R. Miles?

  Anne Libra, Director of Comedy Studies at The Second City, longtime collaborator and friend of Stephen Colbert, teacher to Amy Poehler, Jordan Peele, and Steven Yeun, 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.

• 3:29John R. Miles?

  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.

• 4:11John R. Miles?

  Before we begin, if Passion Struck has impacted your life, please share this episode with someone who needs it: a friend, a coworker, 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 You Matter 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 Libra. Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating an intentional life.

• 4:56John R. Miles?

  Now let that journey begin.

• 5:03John R. Miles?

  I am so excited to welcome Anne Libra to Passion Struck. Welcome, Anne. How are you?

• 5:09Speaker 02

  I'm great. Thanks for having me, Anne. I'm really excited to be here.

• 5:13John R. Miles?

  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?

• 5:25Speaker 02

  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

• 6:09Speaker 02

  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.

• 6:34John R. Miles?

  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, etc. I hope I got the backstory correct.

• 7:00Speaker 02

  Yes, yeah, go.

• 7:02John R. Miles?

  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?

• 7:23Speaker 02

  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 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,

• 8:09Speaker 02

  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 do. But also be yourself.

• 8:31Speaker 02

  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. And that was the most powerful comedy that I could do.

• 9:01John R. Miles?

  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, you, 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 anecdote. That often becomes funnier than you think it's going to be once it comes out.

• 9:47Speaker 02

  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,

• 10:32Speaker 02

  which, you know, is extensive, 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.

• 11:01John R. Miles?

  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?

• 11:16Speaker 02

  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,"

• 12:01Speaker 02

  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.

• 12:16John R. Miles?

  Yeah, I'm just gonna follow up on that with something I've always wondered. It's one thing for you to write for yourself, for punchlines you're gonna deliver. But how difficult is it to write for someone else? How well do you have to know in order to do that?

• 12:31Speaker 02

  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.

• 13:12Speaker 02

  So the writers I know who write for Stephen, who wrote for him on The Colbert Report, 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 Report 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 always think, at one point in college, my sister was a math major.

• 13:55Speaker 02

  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 she 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. And 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.

• 14:39John R. Miles?

  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 Colbert, 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?

• 15:18Speaker 02

  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.

• 15:39Speaker 02

  And the first thing is recognition. In 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.

• 16:23Speaker 02

  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 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.

• 17:07Speaker 02

  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 easier 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. I'm 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.

• 17:51Speaker 02

  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 that's it. Yeah, go ahead.

• 18:12John R. Miles?

  Yeah, well, I was gonna 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?

• 18:33Speaker 02

  Well, okay, so I'm going to use an example that I use in my book, which is I was working with Jordan Klepper, 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.

• 18:50Speaker 02

  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?

• 19:34Speaker 02

  Because people that we know say scary things, right? We all have had that experience where someone, we really say something that we're like, huh? 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 element. But then we also made the scene about the press corps, who couldn't believe he was saying this and were desperately trying.

• 20:16Speaker 02

  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 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 Klepper'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.

• 20:51John R. Miles?

  Yes.

• 20:52Speaker 02

  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, you're 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,

• 21:33Speaker 02

  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 in all those other places, too.

• 22:19John R. Miles?

  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, micro gains, behavioral courage, and emotional resilience, then join me on my Substack community at theignitedlife.net. Now, a quick break from our sponsors. Thank you for supporting those who support the show.

• 22:58John R. Miles?

  You're listening to Passion Struck on the Passion Struck Network. Now, back to my conversation with Anne Libra. Yeah, so I want to ask a follow on to this because I think it's important. I think everyone today would, if you said we're living in a time of decisiveness, would agree with you.

• 23:17Speaker 02

  Yeah.

• 23:17John R. Miles?

  But you argue truth in 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?

• 23:40Speaker 02

  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 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?

• 24:23Speaker 02

  And then we say, okay, we 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 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 that stand-up comedians do.

• 25:06Speaker 02

  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, then you 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.

• 25:45Speaker 02

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

• 25:57Speaker 02

  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 deepest, darkest fears. 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

• 26:38Speaker 02

  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'm 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.

• 27:08John R. Miles?

  Since you just brought up Seinfeld, I want to stick there because in the book, 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 wait.

• 27:25Speaker 02

  Yes.

• 27:26John R. Miles?

  And that wait 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?

• 27:34Speaker 02

  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.

• 28:05Speaker 02

  Right, the things that there and one of those is waiting for a table. Nobody in TV waits for tables, but gets that 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 and pain points that we've all experienced,

• 28:46Speaker 02

  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 and my own little brain." Right? And then, 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

• 29:31Speaker 02

  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.

• 29:41John R. Miles?

  I loved it. What phenomenal writing that series had from start to end.

• 29:47Speaker 02

  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.

• 30:00Speaker 02

  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, and 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.

• 30:42Speaker 02

  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.

• 30:54John R. Miles?

  Yeah, I'm, I'm gonna stick to Snapple 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

• 31:34John R. Miles?

  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?

• 31:47Speaker 02

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

• 32:31Speaker 02

  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.

• 32:41John R. Miles?

  Oh, my.

• 32:43Speaker 02

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

• 32:54Speaker 02

  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.

• 33:15Speaker 02

  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 this sort of discomfort comedy that we might use in our theaters. We can't do they something that is potentially offensive. And I always love that thing because there's a lot of people who'll 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

• 33:59Speaker 02

  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 like, 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.

• 34:34John R. Miles?

  Yeah.

• 34:35Speaker 02

  Other people see. And we somehow think that we're traveling alone in our giant head orb. 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

• 35:17Speaker 02

  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.

• 35:37Speaker 00

  Yes.

• 35:38Speaker 02

  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.

• 36:22Speaker 00

  Good comedy, yeah.

• 36:23Speaker 02

  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 everybody else shares than telling a joke that you've memorized.

• 36:49John R. Miles?

  Man, I love that. So I want to move on to something that you call thick versus thin comedy.

• 36:56Speaker 02

  Yes.

• 36:56John R. Miles?

  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.

• 37:07Speaker 02

  Yeah, okay. Yeah, good.

• 37:09John R. Miles?

  Yeah, no. So maybe you can explain it through that lens.

• 37:12Speaker 02

  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. If you look at the comedy, they're 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

• 37:54Speaker 02

  about farting, say, although multiple farting can be funnier.

• 38:00Speaker 02

  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? And 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,

• 38:44Speaker 02

  people who are allowed to fart, and people who aren't. We're talking about the ways in which when then all of a sudden, we can add like a political point of view. Who are the people who are allowed to have phalanges?

• 39:01Speaker 02

  Who are the people who are not allowed to be human? And fart?

• 39:07Speaker 02

  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, Luttabu words use T-sounds and F-sounds and K-sounds.

• 39:36Speaker 02

  So if you want it to be funnier, you use those T-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 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.

• 40:19Speaker 02

  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.

• 40:41John R. Miles?

  Yeah, and maybe for the listeners, is 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?

• 40:53Speaker 02

  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.

• 41:03Speaker 02

  Right?

• 41:04John R. Miles?

  So would that be like a thick callback? Or would that be a thin?

• 41:07Speaker 02

  That's actually just thin. You're just, you're saying, you're like, like a thin callback is just repeating something that just happened. But a group that's in a room or something, well, John just left.

• 41:19Speaker 02

  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, we all saw or experienced. And 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.

• 42:00Speaker 02

  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.

• 42:32John R. Miles?

  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 gotta get your grammar right. If you don't get your grammar right, your, 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.

• 43:02Speaker 02

  Yes.

• 43:03John R. Miles?

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

• 43:08Speaker 02

  So the very first couple of things, and we were 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?

• 43:35Speaker 02

  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,

• 44:17Speaker 02

  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, but I don't even know if it exists. But the setup set 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're like, I know, I know so many jokes. Okay, here.

• 45:03Speaker 02

  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 Phyllis Diller's jokes at the Smithsonian. But light travels faster than sound, which is why some people seem bright until they speak.

• 45:31Speaker 02

  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.

• 45:48Speaker 02

  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.

• 46:15John R. Miles?

  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 Day that still teaches you something about timing or audience expectation?

• 46:28Speaker 02

  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 Wait 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

• 47:11Speaker 02

  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

• 47:54Speaker 02

  for an audience that really would go see Les Mis seven times, if given the opportunity.

• 47:58Speaker 00

  Yeah.

• 47:59Speaker 02

  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.

• 48:44Speaker 02

  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 and the tools of humor and comedy is that they do, 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.

• 49:28Speaker 02

  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 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.

• 50:01John R. Miles?

  I'm going to do a follow up on that because you touched on durable brain and point of view and that last component we just talked through. You have taught some really famous people, Amy Poehler, Jordan Peele, Steven Yeun, 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?

• 50:29Speaker 02

  So there's, well, and I will say this, that like Amy in my class was funny and on it from moment one. Say that I would watch her and go, oh, you're so good.

• 50:41Speaker 02

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

• 50:51Speaker 02

  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, that takes time. One of the things that I think is true about Stephen Yun, 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 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

• 51:35Speaker 02

  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.

• 52:20Speaker 02

  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.

• 52:52Speaker 02

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

• 52:56John R. Miles?

  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 hear Tom tell his story of how we 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 to do turn it around. And I think that's what you're saying.

• 53:26Speaker 02

  We laugh when other people share. Also, we laugh when other people share their pain because it is such a relief.

• 53:35Speaker 02

  Right? Oh, you see this too? Oh, you had this too? Oh, and that 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 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.

• 54:10John R. Miles?

  And if a listener wants to be funnier by Friday,

• 54:14John R. Miles?

  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 gotten an important presentation that they have to make their company. Is there an exercise that that you could give to make something that they have to share both safer and funnier for that audience?

• 54:32Speaker 02

  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.

• 54:58Speaker 02

  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 gonna open up the little window to my brain and give you, I'm gonna, 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, I'm gonna 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.

• 55:41Speaker 02

  And the more specific and the more weird that it feels like to you,

• 55:48Speaker 02

  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.

• 56:01John R. Miles?

  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.

• 56:20Speaker 02

  And I want to say this. Don't be afraid to share something that you think you're the only one notices, 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.

• 56:43John R. Miles?

  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?

• 56:53Speaker 02

  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.

• 57:07Speaker 02

  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.

• 57:51John R. Miles?

  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?

• 58:01Speaker 02

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

• 58:06John R. Miles?

  Awesome. I'm going to just plug Carrie's show as well because I love that Second City podcast that he does.

• 58:15Speaker 02

  Kelly's show, Getting to Yes And.

• 58:17John R. Miles?

  Yes.

• 58:18Speaker 02

  Yes, that is my husband.

• 58:19John R. Miles?

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

• 58:22Speaker 02

  Oh, yeah. Yes. In fact, he talks about me all the time.

• 58:26John R. Miles?

  Now I know. I love that show. He does a great job interviewing people.

• 58:31Speaker 02

  Yes. So, yes, Getting to Yes And, Kelly Leonard.

• 58:35John R. Miles?

  Awesome. How could I be so? I do all this research and I missed this one.

• 58:41Speaker 02

  You can go back, you'll hear all about me.

• 58:44John R. Miles?

  Well, Anne, thank you so much for joining us. It was an honor to have you.

• 58:49Speaker 02

  Thanks so much, John.

• 58:50John R. Miles?

  That's a wrap on today's conversation with Anne 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 Substack for weekly insights,

• 59:35John R. Miles?

  our workbooks for every single episode, and reflections. You can subscribe to Passion Struck on our YouTube channels at 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 bestselling 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.

• 1:00:15Speaker 03

  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.

• 1:00:46John R. Miles?

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