Chris Duffy—comedian, writer, and host of the TED podcast How to Be a Better Human—joins Debbie to discuss how humor shaped his path from teaching and improv to podcasting and television. Together, they explore why laughing more isn’t about being funny, but about attention, vulnerability, and connection, and how humor helps us stay human.
Chris Duffy—comedian, writer, and host of the TED podcast How to Be a Better Human—joins Debbie to discuss how humor shaped his path from teaching and improv to podcasting and television. Together, they explore why laughing more isn’t about being funny, but about attention, vulnerability, and connection, and how humor helps us stay human.
Chris Duffy:
I’ve always been interested in each career move being something that teaches me. So what’s something that I would learn? How would it push me? And this was a huge shift for me because it’s the first thing that I did where it was in no way edited for laughs.
Curtis Fox:
From the TED Audio Collective, this is Design Matters with Debbie Millman. On Design Matters, Debbie talks with some of the most creative people in the world about what they do, how they got to be, who they are, and what they’re thinking about and working on. On this episode, a conversation with Chris Duffy about his career in comedy and about the importance of humor.
Chris Duffy:
Anyone can be funny and especially anyone can laugh more.
Debbie Millman:
Chris Duffy has spent his career moving fluidly between teaching, standup comedy, writing, and podcasting, all of which are shaped by curiosity, improvisation, and responsibility. Chris is currently the host of the podcast, How to Be a Better Human, where his conversations center on practical wisdom, vulnerability and growth. His new book, Humor Me: How Laughing More Can Make You Present, Connected, and Happy, is about how to laugh more every day and how to find more humor in the world, which is certainly what we can use more of now. Chris Duffy, welcome to Design Matters.
Chris Duffy:
Thank you so much for having me, Debbie. It’s a pleasure to be here.
Debbie Millman:
Chris, I read that one of your earliest memories is when you brought a book of shaggy dog jokes to the hospital to cheer up your great uncle Norman after he had a heart attack. What gave you the sense back then that humor could be a way for him to heal?
Chris Duffy:
Oh, well, that’s true that I did do that. And it’s interesting the framing of what gave me a sense that humor had the power to heal, because I think a big part of it was humor got the power of giving me attention even when he was getting a lot of attention in the hospital room.
Debbie Millman:
Okay. Total reframe.
Chris Duffy:
But I was also like six or seven. And I think that I knew that laughing made people feel good, and I loved that feeling of connecting with people. And the fact that I could tell them these, now in retrospect, objectively not funny jokes, and they would be delighted was it felt like this incredible magic trick that I wanted to do. And so when I knew that he was feeling bad, I thought, “Well, what makes people feel good? Laughing. I can help that. I can help him out with that.”
Debbie Millman:
And did it?
Chris Duffy:
I think he enjoyed that I was there and trying. I think he was probably faking the laugh, but it might’ve distracted him for a moment or two.
Debbie Millman:
You are a fellow native New Yorker and grew up in a tiny fifth floor apartment in Manhattan. Your dad was originally from the Midwest, so how did you all end up in the city?
Chris Duffy:
Yeah, my dad is from Michigan originally, and he’s the first person in his family to go to college. Then, he got a job working at the Port Authority of New York and New Jersey. Especially for what he wanted, it was this really stable job where you were always going to know you were employed, and then you’d get a pension. And so, he moved halfway across the country for that. And he ended up meeting my mom, and she is from Long Island, and so always wanted to stay in New York. And they got married, and then they’ve literally just lived in two apartments. So they lived in one apartment when I was born. And then when my younger brother was born, on the day he was born, they moved into another apartment, and they’ve been there ever since.
Debbie Millman:
Wow. That is dedication and loyalty.
Chris Duffy:
Uh-huh. It’s also funny because they moved at a time when New York was not what it is now. It was kind of a lot grittier and a lot cheaper. And so, they now live in this kind of fancy neighborhood. Not like the Upper West Side was not a nice neighborhood then, but it’s funny because it’s like they live in an apartment where truly the view is of a brick wall, like three feet away. And so, everyone around them has become these ultra wealthy people with giant apartments and they’re just the fixtures that will never move that have their little tiny space.
Debbie Millman:
You’ve written that you also grew up around terrorism as your dad worked in the World Trade Center during the 1993 bombing and just barely missed the last train to make it into the Twin Towers on 9/11. And you wrote this about the experience. “I remember that night in 1993 when dad walked into our apartment, his face jet black with soot, his suit covered in ash.” Chris, how did those early experiences impact your sense of the city and your place in it?
Chris Duffy:
I think a lot of New Yorkers have this experience, and I can only speak to New York because that’s where I grew up, but maybe other places do too, of when something bad happens or really when there’s a blackout or an emergency, all of a sudden the anonymity drops out and people really are all in it together. You have that sense. And so I really had this feeling of, oh, my dad came home and everyone was so concerned and making sure that he was okay, but then was so happy that he was home. And it felt like not millions of anonymous strangers after that. It felt like, hey, when it really comes down to it, we are rooting for each other. And I think I felt that same way after 9/11 as well, this kind of, okay, well, when push comes to shove, people are here for you.
Debbie Millman:
Was this when you first turned two books as a refuge?
Chris Duffy:
I can remember not knowing how to read and thinking I want to read so badly. So I have always thought of books as a refuge and the highest form of media for me. I mean, I’ve always just loved reading and thought that it was incredible. I think I give a lot of credit to my mom who it wasn’t like we could always afford all sorts of luxuries, but her rule was if you ask for a book, we will get the book. And so we would always go to the bookstore and pick something new out and it was just such a treasure and excitement.
Debbie Millman:
You attended Brown University and from what I found in my research, I believe that you double majored in philosophy and economics. I also saw in another interview that you said that you were an English major. So clarify for me.
Chris Duffy:
Oh, it’s incredible that that is your understanding. I was absolutely in so many ways not a philosophy and economics major. I majored in English in creative nonfiction writing, which at the time felt like the most … It felt like underwater basket weaving, like how are you going to have a career in creative nonfiction writing? And then of course, literally everything I’ve done has been creative nonfiction writing. But I took … The reason it’s so funny that it was philosophy and economics in particular is I took one economics class and at Brown, you can take classes pass/fail, and I took it pass/fail, and I just barely passed to the econ class.
And then a philosophy class, I took a week of the class, and at the end of the first week, the professor said, “If you’re happy with your life, if you don’t want to examine everything and have everything become a challenging question about morality and meaning, if you like the way your life is right now, you should walk out of this class and not come back.” And I left the class and was like, “I’m not coming back to that class. That sounds horrible.” So I dropped the class because I was like, “If that’s what philosophy is, no thanks.”
Debbie Millman:
What a cool professor.
Chris Duffy:
I know he’s directed talent.
Debbie Millman:
Did people like en masse leave the room?
Chris Duffy:
No, I think everyone else was like-
Debbie Millman:
You’re the only one?
Chris Duffy:
“How dare you? I will be here. I’m smart enough.” And I was like, “This sounds bad. What he’s offering is real bad. It’s Pandora’s box. I’m not going to open the box.” Everyone else was like, “Oh, I’ll see what’s in the box.”
Debbie Millman:
Now, you also wrote for the college newspaper, Brown’s Daily Herald, which you can still find some of your bylines online. You had it even then. At that point, what did you think you wanted to do professionally?
Chris Duffy:
I thought I wanted to be a journalist. I was really sure that journalism was what I wanted to do. The idea of talking to people and getting to have conversations and be interested in all sorts of different topics, that just was so appealing, and it still is so appealing to me. But I graduated in, at the time, it felt like the historic low of journalism where I was applying to jobs at papers. And in between when I would apply and when I would hear back, the paper would go out of business. That happened more than one time that I had sent my clips and resume in. And then I actually talked to someone who was a really award-winning journalist, had won …
I think he might’ve even have won a Pulitzer, and I was just asking him for advice. And he said, “Honestly, my advice is that you should not do this as a career. My peers are applying for the same entry-level jobs that you’re applying for, and I think that you would be much better served by doing something else and then writing on the side.” And so I took that advice and I said, “I’ve always loved teaching too. And especially if I teach abroad, then I’ll have a hook where maybe I can report from somewhere where there aren’t as many people reporting and that could be a way to do both.” So that was what I ended up doing.
Debbie Millman:
Well, I don’t want to get into your teaching career just yet because I do want to talk about the cryptic ads that you saw pasted up around campus at Brown with headlines like, “Interested in long-form improvisation?” You were intrigued. So what happened next?
Chris Duffy:
I auditioned to be in the improv comedy group on campus, and I was rejected. And then a person I didn’t actually know at the time, who is now one of my closest friends, was starting his own new group. And I didn’t really know a lot about the idea that there was long form and short form, that was a distinction that didn’t mean anything to me, but I really wanted to be in the group of funny people. That was a huge dream of mine always. And so I auditioned and got to be part of this group that became kind of an institution on campus and still exists now.
And so we created this thing called Starla and Sons which the reason it was called Starla and Sons, part of the joke was every single time that we did a show, we would come up with a different explanation of why it was called Starla and Sons. So it was never the same. And yeah, that group of people, it’s incredible that you even found that story out. I’m always in awe of your research when you do it, when I listen to other people’s. And now having it with me, I’m like, “How did you even know that?” But yeah, that shaped so much of my creative life is being in Starla and Sons.
Debbie Millman:
Now, I read that while you were in Starla and Sons, you pretended to be a talking dog, Satan on the moon, and an astronaut whose head is a foot. Not things that just in hearing the description I would necessarily think as funny, but when did you first realize you were funny?
Chris Duffy:
Oh, I think that I knew that I was funny in a way that not just friends would think I was funny when I was in Starla and Sons. I really do think that. And to this day, I think that some of those performances are the biggest … They’re the high point of laughter and really the magic of being in a room. Because the thing is that when you’re in a college group, you can get 300 people in a room because it’s college and people all want to come support their friends and there’s not a lot else to do. And so you have these 300 people packed in a room and you’re doing something that you and they are surprised by. And when there’s that huge explosion of laughter, I felt like nothing’s better than that, but part of the nothing is better than that feeling was going, “Oh, I am funny. I made that happen.”
Debbie Millman:
I took a improv class back in the early ’90s in New York City, and I was struck by the sense that comes over you after a time when you’re all in it together, where it almost feels like you have a mind melt or a hive mind, and it’s magic.
Chris Duffy:
I mean, that is the part that I like the most. And I think especially when you’re in a group where you perform with each other a lot and you practice together, part of the fun is knowing, “Okay, if I say this to Debbie, here’s how Debbie will likely interpret it.” And I can play with you in that way and also play with, “I think you probably aren’t going to get this reference,” and it’ll be fun to see what you do with that. That is such the most magical part of improv for me. It’s possible to have a lot of fun with strangers, but I think when you really know someone well and you know what their moves are and what their comfort is, it’s fun to be able to set them up for a perfect joke, but also to tweak them a little bit on stage in a supportive way.
Debbie Millman:
Now we can talk a little bit about your teaching experience. After you graduated college, you moved to Cambridge, Massachusetts and began teaching fifth graders in an inner city Boston elementary school. Why?
Chris Duffy:
The short answer is my girlfriend at the time, who’s now my wife, had got a job in Boston, and I thought, “Well, if I’m going to teach, I can teach anywhere, so let me apply for every job I could.” And this was the one that I got. But the bigger reason of why I wanted to teach fifth graders and why I wanted to teach at all is I had done some volunteering afterschool programs and just really liked that age group and felt like similar to the improv, there was this nature of play with elementary school students where you could go into a character or a make believe thing and they would go along with you. And fifth grade was nice for me because it was kind of like the end of that. So they were at the most mature where they would still go along with you and playing imagination games or a make believe. And actually halfway through the year, you would feel the switch into these are middle schoolers now.
Debbie Millman:
Interesting. I read that you feel as if everyone has the potential to be funny, everyone has the potential to be creative, but something does happen in that fifth grade year that does move you into perhaps more practical thinking. Were you trying to stave that off and keep them as creative and as engaged in humor as possible?
Chris Duffy:
Definitely. Them and myself. I mean, partly you become what you’re surrounded by and I want to be surrounded by that kind of energy. There are some studies that I’ve read that say that fifth grade for many people is kind of the peak of totally uninhibited creativity. And that’s partly because we become more social creatures. Middle school and high school are so much about where do I fit into the group and how do I manage social dynamics? And a lot of that is really painful and awkward, but some of it is just necessary for living in a society. And before that, kids are less aware of those dynamics. And so they’re so creative because they have no thought of what are other people going to think of this idea? And that’s something that I really want in myself is as much of that as possible. Forget about what other people think. What do I think and what’s the most fun?
Debbie Millman:
You were also teaching adults improv comedy at a local theater on the weekends, and you described the experience in this way. “This was a group of retired folks, graduate students, and semi-successful business people who were paying money to spend their Saturday mornings in an unventilated basement with me. And most of the exercises that we were doing together were to get them to let go of the self-critical part of their brain, to release the idea that there was a right answer to find and to instead be more comfortable with their honest, creative, idiosyncratic thoughts.” Chris, how do you go about doing that?
Chris Duffy:
Okay, this is great. I actually want to do it with you.
Debbie Millman:
Oh my God. Okay.
Chris Duffy:
So my favorite exercise is a really simple one and it’s just categories. So it literally is any category. And it’s important to know that this is building a muscle. So it’s not necessarily how do you come up with the most hilarious thing. But if I say to you right now, name three kinds of cereal, just go as fast as you can. What are three kinds of cereal?
Debbie Millman:
Captain Crunch, Frosted Flakes and Rice Crispies.
Chris Duffy:
Great. So three kinds of cereal. You can kind of think three ahead. Your brain is able to assemble three, but when you push it further, when you go to seven, and the rule being you’re just going to say it as fast as possible. So if we said we’re going to say it on the beat like …
Debbie Millman:
So keep going? Four more or seven?
Chris Duffy:
No, I’m going to have to give you a new category because now you already thought of cereal.
Debbie Millman:
Oh, I was already like Lucky Charms.
Chris Duffy:
Okay. But the only rule is it doesn’t have to make sense. It just has to be as quick as possible.
Debbie Millman:
Seven things.
Chris Duffy:
Seven things. So let’s say seven things you might put in your purse. One, two, three, go.
Debbie Millman:
Tissues, those flosser sticks, lipstick, those mints, my wallet, my phone, and a brush.
Chris Duffy:
Okay, great. Seven. So you were giving your honest … At certain point, by the time you got to brush, you weren’t thinking anymore, you weren’t planning. It was just what is actually in there. And again, the point is not that brush is the funniest answer, but you get past the what do I think I’m supposed to say and you just start saying the real things. And the more you give wild categories, right? Seven things you’d never want to hear someone say to you when you’re at the beach. The first few will be things that you might expect, but the seventh might be like, “You ate my sandwich.” It’s like you stop thinking of the planned ones and you just start-
Debbie Millman:
Right. Actually, I wish I had thought about what was in my bag right now because the seventh thing could have been a banana.
Chris Duffy:
Exactly. Okay. See, that’s great. And I think again, it’s really fun to do exercises like that because it gets people out of the mode that they normally are in, which is what’s accurate and what is acceptable and instead gets you to what’s honest and what’s authentic. So it may very well be that you would say something that’s in your bag that is not in your bag, but is emotionally true. And that is where a lot of comedy and a lot of creativity comes from, in my opinion.
Debbie Millman:
Yeah. I think that comedy is one of the highest forms of art because you are actually able to get people to think and laugh at the same time. And what is better than that? Maybe poetry.
Chris Duffy:
Well, when it’s done … Yeah, poetry, I think … Well, I’ve said this to a few people, which is because it’s one of my favorite jokes of all time, but my friend who’s a comedian, Mike Kaplan, he has a joke where he says, “I say something and you, the audience get to decide. If you laugh, it’s a joke. If you don’t laugh, it’s a poem.” And I love that.
Debbie Millman:
I love that.
Chris Duffy:
Because it’s kind of true.
Debbie Millman:
I love that. Well, it’s interesting because I also read that you’d said something about if people laugh, then it’s funny, if people don’t laugh, you’re bad at it. When you strike out in a baseball, if you’re a great baseball player, you just struck out. But if you strike out on the stage, you’re bad at comedy.
Chris Duffy:
Totally. There’s such a short feedback loop, which is if you write a book, if you paint a painting between doing the work and finding out the reception of the work, there’s a really long time. Whereas when you tell a joke, it’s seconds between the creation of the thing and the reaction to the thing. And so what’s nice about that is you get this immediate yes or no, but you also then have an immediate chance to pivot. If you’ve written a 700-page fantasy novel and then it comes out and everyone goes, “That makes no sense.” It’s pretty hard to be like, “Well, what if the dragons didn’t wear hats and instead were angry?” You can’t just pivot in the moment from your dragons wearing hats novel, but you can pivot in the moment from saying something about an idea and saying, “Okay, that doesn’t resonate. What if I said it in a different way?” But can I say one other thing here?
Debbie Millman:
You can say whatever you want, Chris.
Chris Duffy:
It’s kind of funny. There’s something interesting, and I feel like you will totally get this, which is I started doing improv comedy and I started doing podcasting at a time when both of those were not cool. There was no social desirability to either of those things. And similarly, you were podcasting way before people even understood what a podcast was. And you have been working in design thinking way before that was a world of where design meant something that people were like, “I’ve got to have design on my resume.” Now, you don’t even like the term design thinking because people use it in this way that’s not even how you started thinking about design. I just think that it’s kind of interesting to then be on where we are now where everybody has a podcast.
Debbie Millman:
Yeah, it’s embarrassing to actually say you’re a podcaster.
Chris Duffy:
Which is true, but it’s embarrassing in a different way. It used to be embarrassing because people were like, “That’s something on an iPod? What is it that you do?” I don’t even understand technically how I would access it. And then I think the improv part is also funny because it used to be like, “Oh, this is the nerdiest of comedy nerds.” And that was part of the joy of it. And now it’s like I’m taking this improv class because
Debbie Millman:
Amy Poehler told me to take one.
Chris Duffy:
Yeah. That’s how you become Amy Poehler. It’s like, “No, no, no, this is how you become the guy in the basement teaching the improv class.”
Debbie Millman:
Well, speaking of, you continued performing comedy at night while you were teaching, but I read that you felt that there were maybe 100 people hearing you perform when you were doing this and you were leaving with some great stories about being a babysitter, but nothing that really mattered. And I read that this period in your life became really emotionally difficult and you described it as feeling overwhelmed and burnt out. You were also teaching students facing homelessness, illness, trauma. You also said that during this time you lost your sense of humor and saw laughter as incompatible with responsibility.
Chris Duffy:
Yeah, I think that I had an experience that is not actually all that uncommon for people who really care about making a difference in the world. If you’re driven to have some sort of impact, which is you come out really idealistic. I was like, “I’m going to work in this school and I’m going to change my students’ lives. After they have me, everything will be different.” And then what actually happened is you teach and it’s really hard and maybe you’re not even connecting with the students at all. And some days the classroom is totally chaotic and then you have to grade their paper. It just was so-
Debbie Millman:
And fifth grade, you must have had to deal with their parents.
Chris Duffy:
Oh, that’s the other thing, right? I would be trying so hard and then I would get a phone call and it would be a parent yelling at me. And it’s not even that they were unjustified in yelling at me sometimes, but it just felt like, “Oh, I’m bad. People don’t think that I’m good at this and I’m not actually making a difference.” And so the thing that I think is the relatable experience for many people is the solution to that was to just try harder. And try harder meant be more serious, cut out the things that give me joy or that give relaxation to just give every second to doing this and to just try and drive straight at the wall as hard as I can and as fast as I can.
And it really was not working. It wasn’t working in terms of connecting with the kids. It wasn’t working in terms of me being able to have the energy to teach and to not burn out. And comedy became this release for me when I actually found it again. But there was this period where it felt like, “Well, that’s silly. You’re dealing with real stuff. You shouldn’t have any space for this.”
Debbie Millman:
I read that you came to the realization that you were no longer going to be a teacher. So you made a very conscious decision and decided to rebuild your sense of humor, to deliberately inject more laughter and comedy into your life and to transform the way you saw the world, like #goals, Chris. How did you go about doing that?
Chris Duffy:
Well, I want to push back on a tiny bit of that framing, which is I definitely did think I’d need to consciously make my life have more laughter in it, but it wasn’t from the framework of I’m not going to be a teacher. In fact, I still think I will probably go back to teaching at some point. That’s a goal for me is to find a way to have another chapter of my career where I’m teaching again.
Debbie Millman:
I think you should teach improv. I’d sign up in an instant.
Chris Duffy:
Absolutely. I loved teaching improv, and if you’re going to be in the class, man, I’ll just teach a one-on-one. But yeah, I want to teach again. So I think that’s not it. But I did realize, this is not who I am and not being who I am is impossible to sustain. So I need to find a way to have laughter be a part of my life. And part of it was if I care about education, if I care about people being informed, but I also care about laughter, maybe there’s a way that I can do it that isn’t this exact box. And a lot of the things that I’ve done since I had that revelation have kind of combined those pieces of I want to be teaching people, but I want them to be laughing. I want to entertain with a purpose. Because that is going back to, you said the story of there’s a hundred people in the room, what am I leaving them with?
I have always felt, and I think this partly is just because of my parents who both were public servants, this idea that it’s not enough if your job is just satisfying, that there has to be some sort of reason for it, a greater good. And I think that’s what I was hitting the wall with when comedy did start working as, “Huh, what’s the point? If you can get people to pay attention, what are you getting them to pay attention to?” And I think there should be an answer to that.
Debbie Millman:
Making the choice to take humor seriously and to cultivate it more does seem to have changed everything at that time in your life.
Chris Duffy:
Totally.
Debbie Millman:
Is that when you decided to take your standup more seriously?
Chris Duffy:
I think it was when I decided to take all forms of comedy. I’ve always been kind of agnostic because I like improv, I like standup, I like writing funny stories. I’m always of the opinion that rather than being a purist, a lot of comedians are very purist in their approach. They’re like, “I’m a standup, or I only do improv, or I only perform sketch comedy.” And I’ve always thought, if I can make you laugh in whatever way, that’s great. I mean, and part of this, again, comes back to thinking of my dad working at the Port Authority, which is when I left teaching, I said to the principal I was working with, I said, “I’m doing the math and I think I can pay the bills if I do this for a year, even if I work halftime somewhere else. If I leave and it doesn’t work out, can I come back?” And she said, “No promises, but we hire new teachers every year and we really like you. So if you want to come back, it’ll probably be okay.” So it felt like there was not a huge risk in taking one year to see if it would work. And the response that my dad had to the year is, “I can’t believe you paid your bills.” And that kind of is still how I think of it all.
Debbie Millman:
I was going to ask you that. How were you able to pay your bills doing standup comedy? Open mic nights don’t pay very much.
Chris Duffy:
No, and it was so not that. It was like I got a very small contract to help make some funny videos for an education nonprofit where we interviewed kids and made videos they would use in the classroom. I was getting paid a little bit to do standup. I had started this public radio show, which became the main thing that I did, and that was not a public radio show at the time. It was a live show that we recorded. And again, it was the first wave of podcasts, but we would do it in a small room with 30 seats and film it or record it. And the nice part of coming from having been a teacher in a public school is to get to the same level of pay, it wasn’t like I was making a lot of money as a teacher. So I was like, “Okay, I can get to $30,000 a year if I make this money from comedy and then the rest of it I can do some other random stuff.” So I did all sorts of random non-comedy jobs to pass the time.
Debbie Millman:
How does one go about creating standup comedy?
Chris Duffy:
I think that for me, it goes back to the reason why I think that this is a teachable skill, which is the first part of standup is actually the most interesting part to me. People really focus on the performing part, which is you’re standing in front of a crowd, how do you deliver it in a way that they understand, all that part. But I actually think the most interesting part is how do you notice the thing and come up with the idea, and then how do you process that into a way that is something that other people will think is funny? And so that part I think is really anyone can benefit from, which is you walk through the world and you pay attention to things and you notice what strikes you. It’s seeds, right? It’s not like you find the full-grown harvested plant.
So you’re walking through the world and you go, “That’s a little odd.” Or, “Huh, why is that like that?” Or, “Why are these people acting in this way?” And you think about it. And what I do and what every professional comedian I know does is you write those little ideas down in a notebook, or I have an app on my phone that has tons and tons and tons of ideas like that. And then if you’re first starting in comedy, one of the things that they say to do is to take that idea and then put an emotion on it. So I hate when or I’m afraid when or I love when or it’s so sexy when. If you put one of those types of emotions onto the observation, it instantly becomes charged in a way that is useful for comedy. So that’s often how you can frame a thing.
Debbie Millman:
How did you get comfortable with the idea that you were likely going to fail in the pursuit of being funny at standup comedy?
Chris Duffy:
By failing over and over and over and over again.
Debbie Millman:
And how do you manage that? How do you handle that?
Chris Duffy:
Well, I think there’s a part of me that is stubborn and thought like, “Why did that not go well? It should have gone well.” So there’s part of me that said, “I got to figure out how to make that go well. I can’t let it stop there.” But I think the other part, which it’s funny because you would think that this would be more transferable to other failures in my life, but with comedy, I realized really quick that when you bomb, when you go up there and nobody laughs, people don’t really remember that. It’s actually really rare that two days later people are like, “Do you remember that guy who told those really unfunny jokes? His name was Chris Duffy.” Most of the time they’re like, “It was a bad show.” But it’s totally … People only remember when you are so good and then they’re like, “Wait, what was that guy’s name?” That’s really the thing that they stand out. Otherwise, they just go, “Eh, it’s kind of a bust of a night. Didn’t really like the comedy show.”
Debbie Millman:
What did those first, earliest open mics teach you?
Chris Duffy:
If you’re someone who … Well, I don’t know. I’m thinking about the listeners, but also have you ever done an open mic?
Debbie Millman:
I didn’t do an open mic for comedy. I did an open mic many, many years ago where people were reading essays or poems, things like that, almost like a slam, but not really. And then after I finished reading, someone came up to me and told me I was being derivative of Karen Finley and I should be ashamed of myself and I’ve never done it since.
Chris Duffy:
Oh my God. That’s incredible. That’s really incredible. How dare they?
Debbie Millman:
How dare they?
Chris Duffy:
And also being derivative of another writer is that’s how you become a writer.
Debbie Millman:
And Karen Finley, goals.
Chris Duffy:
Yeah, that’s great. I’m like, if someone came up to me and like, “You’re derivative of John Mulaney.” I’d be like, “Thank you so much. That’s what I was going for. Oh, thanks. That’s what I was trying for.” Yeah. I mean, the reason I ask you that is because most comedy open mics are very, very, very few regular people in the audience. It’s mostly performing for other comedians who are also trying to get better and are not very successful either. Otherwise, why would they be at this open mic? And so the thing that I realized really quick is two parts of that is one, most of those people are not even really listening. They’re just thinking in their head about the thing that they’re going to say when they go up and trying to practice it.
And then the other is that people, the other comedians are less impressed by you having a great joke. I mean, they’ll like that, of course, but they’re actually most impressed by consistency like, “Oh, you’re here every week.” That’s how you make friends with the other comedians at the open mic, “Oh, I seen you around. Oh yeah, you’re putting in the time.” And so when I started to realize that that was what was respected, it made it a lot easier to fail because that wasn’t even the metric that people were judging whether they liked you by or not.
Debbie Millman:
Was your meeting other people at these open mics the way you got into writing for television or was that a separate path?
Chris Duffy:
Yeah, it was a separate path because I’ve always thought however I make people laugh is great. I was going to open mics, I was doing improv too, and improv and standup are very separate world. But then I had this idea where I thought because of I was thinking about what would I want people to leave with? And I was living in Cambridge, so I was quite literally commuting on a bus that would go past Harvard and then go past MIT. And I would think, “There’s people on this bus who are geniuses. There are people riding this bus who are going to change the world and I’ll never find out what they do or why their work is so important.” And that idea stuck with me. And I was thinking like, “I have this platform, even a small platform, and I feel like I don’t have anything to say with it. And then these people have this really important stuff to say and no one listens to them who is not in their field already.”
So I had the idea of what if we combined those worlds and what if comedians tried to guess what scientists did? And then we interviewed them about their work. And so I started this show that I called You’re the Expert and it was kind of immediately a success. From the start, people, friends came and liked it. And then the second time they all told their friends. And so the second time we sold out. And then the third time, there was a waiting list. And so we moved from the 30 seat room to the 100 seat room. And then the next time we moved from the 100 seat room to the 200 seat room. And then after several months of selling out, it just became this thing where there was this energy to it.
And I started to meet more and more successful comedians because they were on the panel. And I was hosting this show that was built for me. It wasn’t like me trying to be as good at standup but not being as good. This was the thing that played exactly to my strengths, which is I was so curious about the scientists and I wanted to hear the funny things that the comedian said. And so my first TV writing job was because Josh Gondelman, who had been on the panel a bunch of times and had a really fun time, he got an email because he was working it Last Week Tonight, and they emailed the staff and said, “Hey, we’re staffing for a new show that is going to be a late night comedy show about science and nature. Do you know anyone who would be good for this?” And he said, “There is literally one person in the country who does this. It’s Chris. You should at least interview him.” And they took a chance on me and that was my first TV job.
Debbie Millman:
And was that Wyatt Cenac’s Problem?
Chris Duffy:
No, this was a show on National Geographic actually that was two seasons of a show on National Geographic.
Debbie Millman:
Explorer.
Chris Duffy:
Explorer, yeah, which I think they have fully scrubbed from the internet. I think you quite literally cannot find it online anymore, but …
Debbie Millman:
I found references to it.
Chris Duffy:
Yeah, I had a really fun time writing on it, even though the show was not a rating success. And the people I worked with were great. So that was what led to Wyatt Cenac’s Problem Areas, which was probably the show that I worked on that people actually saw, but one of the producers there had really liked working with me. And so when that happened, I was able to apply.
Debbie Millman:
Talk about wrong answers only-
Chris Duffy:
Yeah.
Debbie Millman:
… but that is, I think, still ongoing.
Chris Duffy:
Told I’m actually going to do an episode of it tonight.
Debbie Millman:
Oh, wonderful.
Chris Duffy:
Yeah. A show of wrong answers only tonight after this. So you’re the expert, this public radio show for about seven years, and then I stopped, which actually I think is relevant to a lot, at least for why I listen to Design Matters. People might who are listening may find this interesting too, is that because I always like to hear people’s career paths and how they think about their work. So I did the show that was great for seven years. And then I stopped, not because I didn’t like it, but because I felt like I’ve kind of learned what I’m going to learn from this. I know how to interview scientists, I know how to run this panel show and it wasn’t making a lot of money. So it wasn’t like, “Oh, I’m going to lose my income stream.” But it felt like, “Okay, I’ve kind of creatively accomplished what I’m going to accomplish with this.”
So I stopped doing it. And then during the pandemic, the National Academy of Sciences reached out to me and said, “We’re trying to do something during lockdown that would be remote where comedy and science would be combined. Would you be interested in doing that?” And it had been a few years since I’d done the last You’re The Expert. So I thought, “Okay, well, this could be an interesting thing. It had always just been an audio show. Maybe there’s some version that’s like a streaming game show that would be fun.” So we started working together, this experimental program at the National Academy of Sciences called Lab Acts where they just try and do public engagement. And we worked together on this and then it became this multimedia show called Wrong Answers Only, which has a lot of the spirit of you’re the expert, but is instead visual and in front of a live audience.
And at first it was in front of a live audience over Zoom and now it’s in live audiences in person. And it’s three comedians and they interview a scientist about what they do. And it is so fun to do. It’s so fun. It is so funny. And part of the joy is you get these really funny comedians and they have never made jokes about sea urchins, like an hour of sea urchin jokes. And they’re like, “This is new for us too.”
Debbie Millman:
I learned a lot about sea urchins in my research.
Chris Duffy:
See, that’s what I love is then you become like this … And this is partly why I thought I wanted to be a journalist at the very beginning is because you get to become a weird expert in sea urchins for a week. And then everyone in the room is learning about sea urchins. And for me, the biggest joy is actually that the scientists who are interviewing always leaves going like, “I was a rockstar for a night. This was a room full of people totally enraptured by my work.” And that is so fun because I actually think that’s really what they deserve and so rarely get.
Debbie Millman:
In 2020, you created a one-person show titled How to Stay in Love. It was a multimedia show featuring research and interviews with neuroscientists, couples counselors, psychologists, and a year’s worth of interview footage of real couples. What motivated that?
Chris Duffy:
It’s a really interesting question. No one has ever asked me about this, partly because it was a very experimental thing that I didn’t do very many times. I think the honest answer is that I was processing something that was really serious and I was struggling with a lot, which is my wife, Molly, just being in a really dark place and her really being in a place of suffering and pain and depression. And I was trying to figure out how do you make things work when it’s really hard? And I was trying to process that through comedy and art. And I want to be more generous with my … I was about to say I kind of regret doing that show, but I don’t think I regret it as much as I think I was grasping at straws. And that’s part of what I came about.
I was like, “What if I turned this into art?” And I think sometimes you need to have metabolized it more to make it into good art. So I think that maybe if I came back to that now or in a few years, I would have a better answer. But I was genuinely trying to say, “How do you stay in love? How do you keep making this work?” And we are still together and we are not in that dark place anymore. But that’s kind of what it came out of was just being like, “Oh, it’s really hard and I want to help this person who I love and how do you help someone who you are incapable of helping at the moment?”
Debbie Millman:
Do you have an answer to the question of how to stay in love?
Chris Duffy:
I think that the answer is … I’m curious what you think too, because you’re someone who’s in a long-term relationship as well. But I really honestly think that the answer is that you are putting bricks into a wall and that you are not judging each individual brick, but rather thinking like, “Okay, we have built this huge wall so far, this foundation of this house,” and it took a lot of time and to have respect for that, and then to also think some days it’s okay.
Some days you just get another brick on or you don’t even get any bricks on, or someday some of the bricks crumble, but there’s still a lot there. So I think for me, it’s less about it always being perfect and more about thinking that the fact that we have both chosen to do this and to put the effort in really matters. And then I think the other one is to be like, “If we had a magic wand, both of us would make this work.” The struggle is not because you’re trying to make this hard or I’m trying to make this hard. The struggle is that there’s-
Debbie Millman:
It’s hard.
Chris Duffy:
… situations. Yeah.
Debbie Millman:
Things are hard.
Chris Duffy:
And sometimes it’s a tough … We had a tough two or three years, but then now it’s like that feels so far away, even though it’s not. So it’s so hard to realize in the moment that it won’t always feel like this. And that’s true on your individual level as well as on a relationship level. So I think that’s maybe my biggest lesson that I’ve learned.
Debbie Millman:
Well, relationships, intimate relationships were always my Achilles heel, likely because I didn’t come out until I was 50 and prior to that had always been in heterosexual relationships. So yeah, that was a problem. I think you’ll love this answer more than anybody I think that I know. I think the secret of our staying in love is having fallen in love through laughter and that-
Chris Duffy:
I do love that answer.
Debbie Millman:
Roxane finds me funny. I always tell my students, if you laugh at my jokes, I will give you a better grade. But she genuinely finds me funny. And I’d always had, as I was aging and getting older and thinking about relationships, what would be the number one thing that I would want in a relationship? And it was that my partner would find me amusing and Roxane finds me amusing. She really does. We laugh all the time. And even when things are hard, even when the world is falling apart, we still find something to cackle over. And that is, I think, what fuels our love.
Chris Duffy:
That is such a beautiful answer. I really do genuinely love that.
Debbie Millman:
Yeah, I thought you might.
Chris Duffy:
Well, the other thing that I think is interesting too, thinking about those first 50 years of intimate relationships too, is the honesty piece. You have to be really honest with yourself and with your partner. And I think something that I am kind of constantly stunned by in my relationship, even after 20 years, is that when I think this is a thing that I shouldn’t say, or this is an unspeakable type of thing, when I actually do say it, it turns out that it’s okay. And I think that you can just be honest with the other person and that that’s the root of the successful relationship. It never stops being incredible to me because it’s always the huge weight that I’ve assigned to this thing is gone as soon as you say it. Not to say it’s always easy, but …
Debbie Millman:
Yeah. I also think that when you fight, if you can develop a little bit of scar tissue that sort of helps the foundation feel more secure.
Chris Duffy:
Totally. And also, one of the funny things about getting married is that people often give you at the ceremony afterwards, they give you advice and so much of the advice is terrible. One of the worst pieces of advice I think people always give is never go to bed angry. And I’m like, “That’s the opposite of what you should do.” If you’re angry, try going to bed, try having a snack and then bring it to the other person.
Debbie Millman:
Walk it off.
Chris Duffy:
Yeah. It’s almost always that. It’s really not about them. It’s like you’re cranky and hungry. Go sleep it off.
Debbie Millman:
I never thought about that that way. That’s brilliant. That’s brilliant. Chris, I have so many other things I want to talk about. I want to talk to you about your book, but before that, I can’t not talk to you about your podcast. In 2021, a year after how to stay in love, you began to host the original TED podcast, How to Be a Better Human. How did that opportunity come to be?
Chris Duffy:
I had done a standup show in Brooklyn at this little theater called Littlefield, which is a great theater. And someone from TED had seen me do this PowerPoint presentation that was about … I think it was actually about becoming the CEO of LinkedIn, which is a joke that later on-
Debbie Millman:
Okay. We were going to talk. I want to talk about that for a moment just before we get to the book.
Chris Duffy:
Sure. But I did this PowerPoint presentation that was a standup show and a PowerPoint presentation, and they thought it was really funny. And so then they, I guess, had me in their head. And Ted was coming up with the way to make this show, how to be a better human. And they wanted it to be hosted by someone who could take some of the air out of the TED brand because sometimes it can be very impressive and intimidating. And they wanted someone who could be like, “Okay, what would a regular person do?” And because a lot of my comedy is like that, and a lot of my comedy was talking to experts and going, “You’re a physicist, but I have to admit that I don’t know what physics is. And I know I was supposed to learn that in high school.” So they were like, “Why don’t you audition for this?” And I auditioned and did a lengthy round of auditions. And then they picked me and I got to start hosting a show, which has now become a huge pillar of my career.
Debbie Millman:
And it’s a wonderful show. Your move into hosting a podcast shifted you from performing alone to really facilitating dialogue, conversation.
Chris Duffy:
Totally.
Debbie Millman:
What drew you to that format?
Chris Duffy:
Well, I think I’ve always been interested in each career move being something that teaches me, so what’s something that I would learn and how would it push me? And this was a huge shift for me because it was the first thing that I did where it was in no way edited for laughs. 0% of how to be a better human is about how can you make this a comedy show?
Debbie Millman:
Did the TED folks understand that because of your natural inclinations, the show would lean towards funny?
Chris Duffy:
Yeah, I think they were drawn to the idea that I would make it accessible and that I would kind of be allergic to the self-seriousness because you cannot be … If you want to be a successful comedian, if you come out and go like, “I’m so smart and I’m so successful,” people instantly just hate you. You cannot come with that.
Debbie Millman:
You could be in any discipline.
Chris Duffy:
Yeah. And so they were like, “Okay, hopefully you’ll take that tact and be willing to laugh at yourself.” But for me, I had to really learn to trust the editors and the producers that they weren’t going to make me look like little Tony Robbins or something like that, because that’s just not who I am. And I was worried, “Oh, you’re going to make it so that I sound like I’m some sort of motivational speaker and I’m not a motivational speaker.” It messed with my self-definition.
Debbie Millman:
In what way?
Chris Duffy:
Because I thought, well, I’m a comedian first, so everything I do has to be about how many laughs do you get? And this pushed me to be able to say it can be earnest and it can be interesting, and that’s also okay. You can keep people engaged and not have them think you’re a self-serious, pretentious hack without them laughing 100% of the time. And that was new to me, honestly, and I was scared of that idea.
Debbie Millman:
Do you have to ever have to hold back from being funny?
Chris Duffy:
Definitely.
Debbie Millman:
Oh, really?
Chris Duffy:
I mean, what I try and do is I try to not hold back from genuine connection, which often is funny, but certainly there are episodes of the show and there are people where I know I could make this into a bit, but it would kind of cheapen the conversation. So it’s like you can switch onto a character, which is a different kind of comedy, but I could come in and be like, “Well, I have 15 ideas about how we could transform trash into treasure.” People would be like, “Okay, but this person is actually talking about recycling and it is important.” And it’s like they don’t need your pitch of like, “What if we wore a trash belt every day made of new trash?” That’s not a genuine idea. So I try to not do that part, but I try and do the … If I have a genuine reaction, especially if it’s self-deprecating, I try to put that in, but not the other one.
Debbie Millman:
Before we start talking about your new book, I have two anecdotal stories I want you to share with the audience because I was so charmed with them. The first was when you won your first Webby Award. And I understand your dad was so proud. He shared the news in a DM to a celebrity on Instagram. So I’m wondering if you can share that story with our listeners.
Chris Duffy:
Yeah. So we won a Webby for Best Advice & How-To Podcast, which was very exciting. It was first one that I one.
Debbie Millman:
Absolutely. It’s like the Oscars of podcasts.
Chris Duffy:
That’s right. Yeah. And my dad, very sweet earnest man that he is, messaged on, I think Facebook, maybe Instagram, he messaged Drew Barrymore, but through the Drew Barrymore show. And he was like, “Drew,” first of all, he’s on a first name basis. That’s already like, “Okay, Drew, you don’t know her.”
Debbie Millman:
Dad and Drew.
Chris Duffy:
Yeah. Yeah. He was like, “Drew, my son Chris is a comedian. He just won this award. You got to have him on the show. You two would love each other.” Wrote this very earnest thing. And what’s so funny about that is that it’s sweet that he did. It’s very supportive. And I love my dad a lot, but it’s also so funny that he was like, “Hey, you better get your dates … your availability’s ready because the Drew Barrymore was going to call you soon.” And this is now three years ago, I think. And he’s still all the time, “Drew’s going to get back to you at some point. Now that the book’s out, Drew’s going to come call …” As though they filtered his DM into the must respond to at some point where he’s like, “It hasn’t gotten yet, but Drew is going to come a call and she’s going to remember that mark after this message.”
Debbie Millman:
I want this to happen so badly that that is the main reason I decided to ask you about it on this show.
Chris Duffy:
Oh my God.
Debbie Millman:
We’ve got to get Drew call Chris Duffy for Chris’s dad.
Chris Duffy:
I would love to be on the show.
Debbie Millman:
If not anything more.
Chris Duffy:
Drew, I would love to be on the show. And also I would love to have my dad’s delusional belief in his ability to book celebrity guests. I would love for that to be turned into reality. The funny thing is though, my dad, a lot of times we make fun of him because he is very earnest and believes stuff like this can happen. But then occasionally he makes these incredible things happen like that where he’s like an earnest Midwesterner who also lives in New York City, so he crosses paths with celebrities and he so often does not recognize who they are.
So he just treats them the way he treats everyone, which is very friendly. And so one time my dad was at a … He does not go to a fancy gym, but he’s retired, so he goes in the middle of the day and he was working out at a gym and this guy is working out and my dad goes, “Hey, when you’re done, can you spot me?” And so the guy spots him afterwards. And then my dad comes in the next day and the guy’s there again. He goes, “Hey, will you spot me again?” And after the guy is helping my dad lift his whatever he’s lifting on the bench press, someone else comes over and goes, “How do you know Matt Damon?” And my dad goes, “That was Matt Damon?” He had no idea. So every once in a while, my dad is like, “Hey, we go to the gym together. I do know Matt Damon.” I don’t know that Matt Damon knows him, but …
Debbie Millman:
I love your dad. I just need to say, shout out to Chris Duffy’s dad.
Chris Duffy:
Oh yeah, shout out to you.
Debbie Millman:
The very first time I became aware of your work was through your experience on LinkedIn when you were the self-appointed CEO. So tell us that story. For those that might not be aware of this story, this was my gateway drug into the humor of Chris Duffy.
Chris Duffy:
Yeah, I still think this is the funniest thing that’s ever happened to me and that I’ve been involved in and probably will till the day I die. Because I was a comedian and before that I was a fifth grade teacher, I never had use for LinkedIn as a social network. It’s just not how you get a job teaching. It’s not how you get a job as a comedian. So I had always heard about it, but it felt like this unfamiliar world. And I encourage people to, if you have a weird, unfamiliar world, you should dip your toe in and see what happens. And so I was trying to follow my own advice and I went on LinkedIn and tried to make a profile and instantly I was amazed that you could just say your job is anything. It’s incredible to me that you say you work at Nike and they don’t email someone at Nike to say, “Is that true that Chris works here?” So I was curious how high up I could take that.
And so I thought, let’s go to the highest point we can possibly take it. So I made a profile and I said, “My job is CEO of LinkedIn.” And I made that profile on LinkedIn and then I clicked save to see if it would allow me to do it. I actually thought it would just say error, you can’t say you’re the CEO of LinkedIn. But instead, not only did it allow me to, it sent an email to everyone in my contacts list. And so everyone in my contacts list got an email from LinkedIn, not from me that said, “Congratulate Chris on the new job. He is now CEO of LinkedIn.” And that’s the best possible joke that it came from them. And so people of course were dying and thought it was so funny. And then incredibly, it did not get flagged internally for more than a year. And then at my year anniversary, my work anniversary, it sent another email saying, “Congratulate Chris on his one-year anniversary as CEO of LinkedIn.” And that is when I finally got a message from someone into-
Debbie Millman:
How did they get tipped off? How did they find out?
Chris Duffy:
I think it started to go a little bit viral. And so someone must have said like, “Hey, this is really funny. You should look at this.” And then they said, “Oh, that shouldn’t be allowed.” And so I got an email from a woman named Faith who works on LinkedIn’s trust and security team, and she emailed me and said, “Hey, we’re freezing your account because we are concerned about its accuracy.” So I sent her, because I was like, “I’m not ready to let it go so quick.” I sent her a photo of my license front and back and said, “Just to prove it’s accurate, my name is Chris Duffy.” And she said, “Yeah, the problem is not that we didn’t think your name was Chris Duffy. The problem is you’re saying you’re the CEO of LinkedIn.” And so I said, “Faith, you’re taking a pretty disrespectful tone for someone who works for me.” And then five seconds later, she permanently deleted my account. And so that would be-
Debbie Millman:
That’s my favorite part of the story. My favorite part of the story is don’t talk to me that way. So just so you know, there are a whole slew of Chris Duffys on LinkedIn.
Chris Duffy:
Absolutely.
Debbie Millman:
So I think if you change the email you use to sign up, you could go back on.
Chris Duffy:
Yes. Well, here’s breaking news. I have used a separate new email and I have made a new profile and now I am the owner of Linc’dInn, L-I-N-C, apostrophe D-I-N-N. So now I am the owner of Linc’dInn, which is a business networking focus. Yeah. It’s a business networking focused bed and breakfast. And all of my previous jobs are other puns on LinkedIn. So LinkedIn Park, Abraham LinkedIn, those are my previous positions.
Debbie Millman:
Oh my God. Oh, that is so delicious. I did not find those when I was searching for your LinkedIn.
Chris Duffy:
It’s hard to find. LinkedIn has certainly buried my results now. I’m sorry to all the other Chris Duffys because you are almost unsearchable on their network as a result of me.
Debbie Millman:
Okay. Let’s talk about your new book, your brand new book, Humor Me. And I think for anybody listening to the show, you now have ample evidence at how funny this man is and that this is a book you should be reading. It’s a book called Humor Me: How Laughing More Can Make You Present, Connected, and Happy. Chris, why a book and why now?
Chris Duffy:
I have increasingly felt like there is this really weird misconception about what it means to have a sense of humor. The idea is that you are the center of attention, that you’re the one who is at the party and everyone’s circled around you or you’re on a stage, and that is the pinnacle of having a sense of humor. And to me, it’s not that those people aren’t funny, but it’s a very self-centered version of humor. And I think that humor done right is so much more generous and it’s so much more about laughing with people. Like you said, being connected to your partner and knowing that you two are seeing each other so deeply and enjoying each other.
And so it felt like I really wanted to push for my version of humor rather than this performative self-centered one. And I also think that we live in a time where people are not willing to laugh at themselves. They’re not willing to laugh at the absurdity. They feel like they have to be perfect. And I think the beauty of humor for me is to embrace that the less perfect you are, the better, that the more you make mistakes, the more that that is gold and fun and the desirable outcome.
Debbie Millman:
You start the book by stating that this book is not about getting better at comedy. What’s the one line sentence? What is this book about?
Chris Duffy:
This book is about laughing more. How do you have more laughter in your life?
Debbie Millman:
You write that the single biggest misconception about a sense of humor is that you’re either born with one or you’re not. So is it your position that anyone can be funny?
Chris Duffy:
Absolutely. I think anyone can be funny, and especially anyone can laugh more. I think so much of laughter is about noticing things, and noticing is just a practice, an attention practice that anyone can strengthen by doing it more.
Debbie Millman:
You believe that humor isn’t a fixed trait. You described deciding to reconstruct it deliberately. What surprises you most about approaching humor as a practice rather than a personality?
Chris Duffy:
I think the biggest thing that surprises me about the practice is that it changes your day so dramatically that you can have a really hard day and if you find a way to laugh really hard during that, so much of the stress and anxiety and residue is washed away. It’s not that it changes the fact that there were bad, stressful things that happened, but I think we need that kind of cleansing, cathartic relief of laughter and that it’s actually something you can totally make a part of your day rather than having it just be this incredible thing that spontaneously happens once in a while, that if you practice it and especially find what works for you and then do that over and over, it becomes a more common and more frequent part of your day.
Debbie Millman:
You draw a clear distinction between performing comedy and cultivating a sense of humor. When did you realize that these were separate skills and that one could exist without the other?
Chris Duffy:
A lot of times people ask you when you’re a comedian, who’s the funniest person you’ve ever met? And my answer was never a professional comedian. I mean, there’s so many incredible professional comedians. I’m not trying to put them down, but the funniest people I’ve ever met are almost all friends that I know from outside comedy who you’re around them and you just laugh and there’s tears streaming down your face. And it’s not really because they’re saying prepped lines, polished jokes. It’s because they’re so in the moment with you and they bring this spirit and energy and …
Debbie Millman:
So it’s like their approach to life.
Chris Duffy:
Yeah. Also, if you’re with someone who laughs really easily and really hard, that’s so contagious and that’s so fun and they’re not even saying anything funny. They’re just responding. And that is the thing that I want more of in my life and that I want to be more like and that I want people to cultivate is that version.
Debbie Millman:
At the heart of building a sense of humor are three key tools you outline in wonderful detail in humor me, and they are being present or noticing that the world is filled with absurdity, laughing at yourself or noticing the absurdity and weirdness inside yourself. And then third, taking social risks, being willing to be laughed at. And you call these the three pillars of good humor. And I’m wondering if you can share a little bit about each of the pillars.
Chris Duffy:
Sure. And these are ones that I think you can practice each and every one of these, and that’s why I think they’re the pillars of building a sense of humor. So the first one is attention. And I think it’s probably the one that we understand intuitively the most, which is that you don’t laugh at things. You are not struck by things as being delightful if you’re not paying attention. If you’re on your phone and you’re walking on the street, you will certainly not notice the dog wearing a costume that just will … You won’t even notice that there was a dog, but if you notice the dog wearing a costume, that’s something that is a potential thing that could make you laugh, that could make you have a memory. So that first piece is just being attentive to the world around you. And I also think the more that we are willing to pay attention to things, the more that we start to see other versions of that.
If I tell you the dog with a costume story, when you go out on the street, you’re so much more attuned now to pay attention to, is there a dog and is the dog wearing something funny? So when you start paying attention to things, you see more of those things. And then the second one is laughing at yourself. There was a study that I came across in doing the research for the book that I’ve thought about hundreds of times since, which is there was a psychological study and they were looking at people applying for jobs. And so they had research associates pretend to be job applicants, and then they had regular people rate them as, are you funny or not are you funny? “Are you capable and do we like you? Would we hire you?” People universally preferred of the people who were competent, the person who was good at the job was totally capable, but also had just spilled a cup of coffee on their shirt before they came in for the interview.
So the person who was a little bit of a mess, but still knew their stuff, everyone said, “I like that person more. I think we should hire them more. They’re better.” And that I think about all the time because it’s not saying you should pour coffee on your shirt if you are going in for a job interview, but because-
Debbie Millman:
I think you should post that on LinkedIn.
Chris Duffy:
Yeah, on LinkedIn. The number one reason why I dump a cup of boiling hot coffee on my chest every time I have a job interview. Honestly, I probably should post that on LinkedIn. The reason why I think that’s so striking to me is because we have this idea that we should be perfect and that if we are flawless, people will like us more. And instead, the reality is people like us so much more if we acknowledge our flaws and laugh at them and are willing to laugh at ourselves. That makes us more relatable. That also makes us seem more competent and more confident. So that’s the big part of the second pillar for me is don’t be the person who is flawless, instead be the person who spilled coffee on themselves and then is willing to laugh about it.
Debbie Millman:
Why is it so scary to laugh at ourselves?
Chris Duffy:
Because we think that other people want us to be perfect, but that’s not what you want from another person.
Debbie Millman:
No.
Chris Duffy:
I mean, so much of therapy is, for me at least, is my therapist saying, “Well, what advice would you give to another person in your situation?” Because it’s so much easier to see another person, you wouldn’t judge them the way you’re judging yourself. You would never be as harsh with a friend.
Debbie Millman:
Yeah. You wouldn’t speak to other people the way you speak to yourself.
Chris Duffy:
Totally. And part of that is we think if I told you right now, someone can walk in and they seem perfect in every way. They’re beautiful, they’re rich, they have a great relationship, they have never made a mistake. That is a person who you wouldn’t be like, “I’m definitely going to be friends with them.” At best, you’re intimidated by them. And at worst, you’re like, “Who does this person think they are? I hate them.” But we think that that’s what other people need from us because we don’t see ourselves accurately. So I think that’s why we think it’s so scary to laugh at ourselves is because we think we’re supposed to hold ourselves to the standard that no one else even wants.
Debbie Millman:
The third pillar is taking social risks, being willing to be laughed at. You suggest in this pillar to pay attention to doorknobs.
Chris Duffy:
Yeah. This is this idea from Adam Mastroianni who writes this incredible newsletter called Experimental History. And he is a psychologist and he has this idea for … He studied in his dissertation what makes conversations end and do people want them to end when they end or not? And one of the ideas that he came up with is that in a great conversation, we have doorknobs, conversational doorknobs, which is someone offers a knob and the other person turns the knob and it takes us into a new unexpected room or a new area of the conversation. And that any good conversation, you will both be accepting and turning the doorknobs and offering the doorknobs. The classic example is if everyone is just willing to accept, then we’re in a situation where there’s 10 people and we go, “Hey, who wants to get dinner tonight?” And everyone goes, “Great, I’m up for anything.” And everyone goes, “Okay, well, what should we order? Anything’s good with me.” That’s actually-
Debbie Millman:
Sounds like an episode of Pluribus.
Chris Duffy:
Exactly. And it’s harder when you do that. It’s like, “Well, should we get Thai?” Everyone goes, “Whatever.” It’s actually easier if someone says, “I’m really in the mood for soup.” You can say yes or no, but when someone puts something out there, it’s actually much easier in the group to do that. So that’s offering the doorknobs to say, “What’s the best soup you’ve ever had?” And then to accept the doorknob is to say, “Ooh, I had this great soup that was a chicken lemon soup,” that kind of thing. And that’s the bare minimum version of it. But thinking about conversations as you want to give and to receive and to not just be doing one or the other.
Debbie Millman:
Have you noticed that your own attention has changed since you began all of this research? The book is so beautifully complex with studies and experiments and you position it all in really beautiful prose. It’s extremely easy to read, but it’s all really backed by research.
Chris Duffy:
Oh, thank you. I really appreciate that. That was important to me.
Debbie Millman:
Has your own attention changed since you began all of the research? What do you notice? What do you name? What do you let pass?
Chris Duffy:
Well, I’ll give you the honest answer. I feel like I know the answer that is the right answer, but I’m going to give you the honest answer, which is that I started writing this book, and then while I was three-fourths of the way through writing it, my first child was born, and then about five months before the book came out, my second child was born. So there’s been this dramatic transformation in my life in terms of my ability to pay attention, to have energy, to get a full night’s sleep. And it’s also been a really challenging period in my life. And then that’s my internal … So it’s great. I love having the kids, but it’s also having time for yourself, having energy, having the ability to go and seek out things and pay attention. They’re at a much bigger premium than they used to be for me.
And then the other part is the outside world has become so much more devastating. Not that it was ever all peaches and cream outside, but it’s definitely become overwhelming in a new way for me. So I think that my attention has, I feel a lot more draws on it, pulls on it. And I also feel there’s been a real irony about trying to promote a book and talk about a book about having a sense of humor and laughing every day because I feel like it has actually gotten harder and harder than it was before when I started writing.
Debbie Millman:
Wow, that posits the argument that we need it more than ever.
Chris Duffy:
Yeah. A lot of the practices in the book that I described doing are things that I had let lapse, and that when I started to reread the book and get ready, I started to do it again, and they actually made a bigger difference this time now to find a way to laugh at the end of every day with my wife, to pay attention to the things that are funny in the world and not just the dark and depressing things. Those have made a really significant difference in my life now in a way that I think before they were kind of like, “Oh yeah, those are things that I do.” And now I realize how much I need them and how they actually do make a giant difference.
Debbie Millman:
You don’t shy away from the fact that humor can also be weaponized.
Chris Duffy:
Totally.
Debbie Millman:
What responsibility do you think people who are good at humor have once they understand its social impact more clearly?
Chris Duffy:
I think you have a huge responsibility. I think if you think of the classic image of a bully, the image you probably are thinking of is a group of kids all pointing and laughing at one kid. They’re laughing because bullies are actually funny. That’s something that they’re able to do. I’m not saying it’s good humor, but they’re able to get people to laugh. And so I think that is a real power that we have to be thoughtful of how we use. If you talked to me five years ago, I would’ve said, the thing is professional comedy, there’s not like fascist comedians, that’s not even a thing. I would’ve said that’s impossible. And I think we now know that-
Debbie Millman:
It is possible.
Chris Duffy:
Very possible.
Debbie Millman:
In fact running the country.
Chris Duffy:
Very possible and very successful. So I think increasingly, I think of this as it’s a really important tool that makes people want to be around you, that makes people feel connected to you, and that makes people pay attention to what you’re saying, and you have to make sure that you are using that in the right way. And also when you’re laughing at people to think like, “Am I being connected and am I thinking about what is the joke here?”
Debbie Millman:
Yeah, it’s so interesting, especially during the pandemic when I was watching a lot more TV and was running out of things that I was interested in watching. So rewatching a lot of the things that I thought I loved back in the ’70s and ’80s and ’90s, I realized how much of that humor was indeed weaponized, how a lot of humor was about making fun of other people or other races or other classes. And I had to stop watching some of the things that I’ve actually thought that I really had loved.
Chris Duffy:
I’ve had that experience a lot too. Something that comedians talk about, and I read about this in the book, but comedians talk about this as punching up or punching down. So is the joke punching at someone more powerful or is the joke punching at someone less powerful? And so you can make someone laugh by beating up on a person who is less powerful than you, but that’s probably not a very good use of your comedy. And if you’re punching up and you’re punching at the more powerful, that’s probably a better use of your comedy.
And it’s nuanced because where the power dynamics lie changes depending on what you’re talking about and who you are and what the context of the situation is. But I’ll tell you something that is not in the book because I learned about it after the book, but I’ve been thinking about a lot recently in terms of the power of humor in a positive way is I learned a story about Václav Havel who won the Nobel Peace Prize for becoming the leader of Czechoslovakia after communism. And he, before he was a politician, was a playwright. And he wrote this play when you weren’t allowed to say many things in communism.
There were rules about what you could say about the party. And he wrote this play that on its face was a straightforward play. But then when it was performed in a room, people laughed and they all laughed at the parts that were the jokes about how the party wanted people to be perceived, but actually weren’t. So the thing that was important about that for him is he realized that if everyone else is laughing in the room at this, I’m not the only one who sees it that way, that even though we’re not allowed to talk about these things, that actually we all perceive the same ridiculousness and ironic situation in society and that that made him think like, “Oh, I’m not the only one who sees these flaws in society, that that actually was a spark for him.” And I’ve been thinking about that a lot as the power of comedies to say, “Hey, we actually are on the same page that this is not normal, that this is ridiculous.”
Debbie Millman:
Why do people laugh when they’re embarrassed?
Chris Duffy:
Well, from just a pure evolutionary standpoint, most of why we laugh is not at something that is in any way funny. It’s mostly like a social lubricant. So if you record a conversation and then play it back and listen to the laughs, most of them just come at a pause.
Debbie Millman:
I know somebody that does that. She laughs in every pause. It drives me insane.
Chris Duffy:
Yeah. And some people do it a ton, but a lot of it is just to keep us feeling good and things moving along. So I think we laugh at that. But then the other reason why we laugh at things is because there’s some sort of a violation. And often awkwardness, it crosses a boundary. And so we laugh because it’s not such a big boundary, but it’s an acceptable … There’s a theory about laughter called the benign violation theory. So it’s that you laugh because something crosses a line, but it’s not crossing the line so far that it’s dangerous.
Debbie Millman:
You state humor as a tool for social change involves thinking a lot about drawing lines. In what way?
Chris Duffy:
Well, I think we laugh because something crosses the line, but we also laugh because someone is acknowledging a truth that we haven’t thought about consciously before. And so I think a really important way that humor can be a tool for social change is to just help us to imagine the way things could be, right? To say, here’s a great joke. The comedian Kenny DeForest had this joke. He’s passed away, unfortunately, but he has this great joke, and I’m paraphrasing it, but just never the best way to tell a joke.
But basically he has a joke about billionaires where he goes, “I don’t understand why you need the amount of money that Elon Musk has because here’s the thing, you have enough money to end hunger in the world. And if you ended hunger and you ended homelessness and then you wanted a giant yacht, but you don’t have the money for it anymore, we’ll build you a yacht. We’ll do whatever you want. If you want to go to space, we’ll all chip into the GoFundMe and we’ll send you to space. If you do that, everyone will give you whatever it is that you need for the rest of your life.” And I think about that joke so often because it imagines this other world and actually points out some really fundamental truths, which is anything that money can get you, everyone in the world loving you could also get you.
Debbie Millman:
Do you think that there’s a form of humor that is ethically neutral or is humor always doing something?
Chris Duffy:
Well, man, I want to say both. I think humor is always doing something, but I also think I love silliness. I love just a pure silliness. And I think that silliness is pretty close to ethically neutral. If you’re laughing at Mr. Bean, I don’t think that Mr. Bean getting his head stuck into turkey is necessarily taking a real stand on freedom of feature democracy, but …
Debbie Millman:
Well, there is some slapstick that does veer into the violence.
Chris Duffy:
That’s what I’m saying is even as I say it, I’m like, “Maybe that’s not true. I’m not a very mature person. I think a fart is very funny.” Fart might be morally neutral, but then I’m like, “Then you’re judging people’s justice systems.” I don’t know. Everything is political to a certain degree, but certainly things are more or less explicitly political.
Debbie Millman:
One of my favorite parts of the book was your understanding of humor in relation to grief and heartbreak and discomfort. And you write about humor helping people metabolize discomfort rather than avoid it. That to me was one of the most profound learnings in your book. And I’m wondering if you can share an example of how people can best do that.
Chris Duffy:
I think that one of the biggest ways that humor can help with grief, and in particular in that metabolizing, is in the way that it forms a group identity. The reason I say that is if you are someone who has gone through something and you really get it in the same way that I get it, we can laugh about it in a way that someone who hasn’t can’t possibly make a joke about. Let me just take an example from my own life. My dad worked in the Twin Towers, and so someone makes a 9/11 joke to me who did not have a family member who was at risk. It’s a very different version of a nine eleven joke. But if someone else is like, “That was a terrible day. I was really scared that I was going to lose my parent or I did lose my parent,” we can laugh about it and it makes us both realize we’re in the same club.
And so much of the experience of grief and depression or illness is feeling like, “Oh, I’m alone. No one else gets this. No one else could possibly understand this.” And so when you have that clear moment of, oh, they get it, we are on the same page and we know because we’re laughing about it in a way that only people who get it can laugh, you neutralize one of those biggest pieces, which is the isolation. And the other part is a thing that comedians often talk about is comedy equals tragedy plus time. Something horrible happens and then you have enough time and perspective, you can laugh about it. And I think that’s because you can see it from other angles. You can see that it’s not just this one bright two-dimensional thing. It’s also a three-dimensional shape and you can see it from slightly other sides of it.
Debbie Millman:
Yeah, that’s, I think, why people now respond to certain jokes after tragedies with the too soon because of that enough time has not passed.
Chris Duffy:
Totally. Yeah. And I think in your own personal life, too soon is a real thing. It’s much more possible to talk about the worst parts of my life years later than it is weeks later.
Debbie Millman:
Yeah, same. The idea that joy ultimately declares itself most intensely through our heartbreaks came up over and over again in your interviews and in your research for this book. What did that indicate to you?
Chris Duffy:
Well, I think it really indicates … I mean, I’m actually kind of curious to ask you what that indicates to you. I want to hear your take, but I’ll give you my loose version, which is that humor takes a building of tension and it builds to the maximum point of tension, and then it pops the balloon and it releases the tension. And so in these heightened moments where things are as bad as they could be, it’s actually where you can have the biggest laugh because it can let go of that tension. If things are just kind of good and neutral, it’s hard to have a really big laugh. If you’re walking outside and it’s pouring rain, that is objectively funnier than if it’s 70 and sunny. That’s worse, but it’s also like there’s more emotion in it and we can laugh about things that are higher emotion. So I think that’s one reason why, but that’s maybe the clinical comedy writer assessment. What do you think?
Debbie Millman:
Well, I’m only thinking about things that I sort of learned through reading your book, and I’m trying to think if they’re separate from what I might’ve thought of before, but I think that if joy comes after grief, there is a reckoning that’s occurred, a redemption that might’ve been learned or something in its place that has occurred to fill that hole. I remember at times when I’ve been at my most depressed asking the universe for something good to happen, like, “Please, I really need this one. Please let something good happen to me.”
And then when it does happen, there’s a certain gratitude or maybe a sense of being heard, being recognized as you talk a lot about that seeing aspect of understanding between people, that mutuality that occurs that makes things even funnier. You quoted a line from the writer, Nora McInerny, who states that grief is so uncomfortable, especially if it’s someone else’s grief. And I also thought a lot about that in relation to joy, that sometimes seeing somebody else’s grief can not only make you feel uncomfortable because you’re worried that it might happen to you, but on the flip side of that, it could also make you feel very grateful that it hasn’t happened to you. Do you have any advice for getting more comfortable around grief, whether it is ours or someone else’s?
Chris Duffy:
Ooh, my advice is that you don’t have to solve it.
Debbie Millman:
Yes.
Chris Duffy:
And I think that’s not actually the way to get the biggest laugh, of course, but I think you’re allowed to feel bad and it’s okay. And what people want is to be heard, that to be seen and to be given space is what matters. And so the more that you just let a person tell you how they feel and say, “Okay, I think that’s the biggest thing that you can do.” And so often the reason we feel uncomfortable is because it’s like, “Well, how can I fix this? How can I make you not feel pain? How can I make you not feel sadness?” And the answer is you can’t.
And so then we’re uncomfortable because we can’t do the job we’ve assigned ourselves. Listening to you frame this question made me think too is there’s a very common phrase, “What doesn’t kill us makes us stronger?” And I’ve always thought that’s objectively wrong. If you break your leg, that leg is not stronger than it was before. That’s a weaker leg. You’re much more likely to injure the broken leg than you … And in so many ways, what doesn’t kill us does not make us stronger. It leaves us permanently damaged.
Debbie Millman:
Altered. Yeah.
Chris Duffy:
Yeah. But what it does do is it makes us understand what it’s like to be damaged in that way.
Debbie Millman:
Absolutely.
Chris Duffy:
And that’s a lot of what we need when we’re in grief, is someone who’s going to say, “I understand the damage. You’re not better, you’re different, but I also get that difference. It lets you see that difference.”
Debbie Millman:
Yeah, I think that’s some of the power in the whole Me Too movement, just acknowledging that, hey …
Chris Duffy:
Totally.
Debbie Millman:
I’m in that camp as well.
Chris Duffy:
Yeah. And I think so much of the space societally that we’ve responded to the Me Too movement with was about what’s the quick fix that we can get rid of this? Instead of how could we actually hear, it was like, great, how can I get you to stop talking as fast as possible? I think that that’s kind of like what policy can we enact that will be … This is not the Me Too movement, obviously, but with Black Lives Matter, one thing that I think of as an incredible ironic moment is that on social media, there was this big thing.
And then Gushers, the candy, Gushers posted, “We hear you and we are listening and we’re teaming up with Fruit by the Foot.” And it was like, “Gushers, we actually don’t need you and Fruit by the Foot to solve systemic racism. We don’t need your voice. We would love if you heard us, but no one was saying if only Gushers and Fruit by the Foot could team up, we could solve the history of racism in America.” That is incredible to me. Also, the fact that they posted more soon and then they never posted again about it is-
Debbie Millman:
Well, they must have gotten excoriated.
Chris Duffy:
Oh, but I loved that it was like they had something planned and we didn’t let them … If we’d let them post one more time, they had it solved.
Debbie Millman:
Oh my God. When you finished writing your book, Chris, did your view of humor change at all?
Chris Duffy:
Definitely. I think my view of humor has become more nuanced because I think I started this with saying everyone needs to have a better sense of humor and it’s only good. And then the more that I thought about it, some of the things that we’ve touched on of it can be a force that can be used to exclude people and it can be something that creates damage and harm. So I think I have a little bit of a nuanced look at it, but I think that the thing that I stay true in is the idea that the more that we can look at the world around us and pay really close attention and the more that we can connect with other people and laugh, that that is something that would I think really benefit the world and I genuinely believe we need more of.
Debbie Millman:
My last question, if you had to distill the deepest thing writing your book taught you, not only about comedy or humor, but about being human, what would it be?
Chris Duffy:
The things that we pay attention to and document are what we will remember and what will shape us.
Debbie Millman:
Chris Duffy, thank you so much for making so much work that matters, and thank you so much for joining me today on Design Matters.
Chris Duffy:
Thank you so much for having me. I cannot express to you how much I am in awe of you and the show, and it’s a huge honor to be here.
Debbie Millman:
Thank you. Chris’s wonderful new book is titled Humor Me: How Laughing More Can Make You Present, Connected, and Happy. To learn more about Chris, you can go to his wonderful website, chrisduffycomedy.com, and you could read more of his comedic musings on his newsletter, Bright Spots. And of course, you can listen, you must listen to his podcast, How to Be a Better Human. This is the 21st year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.
Curtis Fox:
Design Matters is produced for the TED Audio Collective by Curtis Fox Productions. The interviews are usually recorded at the Masters in Branding Program at the School of Visual Arts in New York City, the first and longest running branding program in the world. The editor-in-chief of Design Matters Media is Emily Weiland.