1140: Bringing More Laughter, Fun, and Connection to the Workplace with Chris Duffy

Pete Mockaitis
Chris, welcome!

Chris Duffy
Thank you so much for having me.

Pete Mockaitis
Well, I’m excited to talk about humor, and not just for the fun of it, but how it can actually enhance our experience of career and job and be an asset in that zone. But could you kick us off with a fun story about some of your most memorable moments in your career as a comedian?

Chris Duffy
Probably the most memorable moment I’ve ever had in my career as a comedian is I was a fifth-grade teacher before I did comedy. And so I never had use for LinkedIn because, listen, like you don’t get a job as a fifth-grade teacher through LinkedIn, like business networking, and you don’t get a job as a comedian through LinkedIn networking.

So I never had a LinkedIn profile, but I’d always heard about it, and I was curious about the world. So one day I went on and said, like, “Okay, I’m just going to make a profile.” And the first thing I realized is you could just say you work wherever. If you say you work for Nike, they don’t, like, email a Nike hiring manager, which struck me as completely bizarre.

And so I wanted to see how high up I could go. So I made my job on LinkedIn, the CEO of LinkedIn. And I thought, like, when I click save, it’ll say, “Error. You can’t do that.” But instead, not only did it let me do that, it sent an automated email to everyone in my contacts list that said, “Congratulate Chris on his new job. He is now CEO of LinkedIn,” which is, to me, that’s the funniest joke that I’ve ever been involved in. And I didn’t even make it. It was just LinkedIn’s like automatic emailing thing.

And then, I was the CEO of LinkedIn on LinkedIn for a full year. And at a year, it sent another email to everyone in my contacts list saying, “Congratulate Chris on his one year work anniversary as CEO of LinkedIn.” And that started going a little viral.

And so I got a message from someone on LinkedIn’s Trust and Security team. My account was frozen. And you can’t make this up. The person on the Trust and Security team, her name was Faith. And Faith said, “Your account has been locked due to concerns about its inaccuracy.”

I didn’t want to let the joke go because I love the joke so much so I sent her a photo of my license, front and back, and said, “There’s proof that my name is actually Chris Duffy.” And Faith said, “The problem is not that we don’t believe your name is Chris Duffy. The problem is you are claiming to be the CEO of LinkedIn.”

And I said, “Faith, you are taking a pretty disrespectful tone for someone who works for me.” And five seconds later, she permanently deleted my account. And so that was the end of my time on LinkedIn. But a very memorable moment in my comedy career.

Pete Mockaitis
That’s fun. Okay. So one takeaway I’m gleaning right away is, “Go ahead and lie about how senior you are on LinkedIn, and the odds are pretty good, you can skate by for a good while with that.”

Chris Duffy
You know, if there’s one message I have for people, it’s, “Commit some light fraud.” No, that’s not my message. You know, I think the heart of what I like about that is that no one was going to hire me anyway from LinkedIn. So I think the thing that I encourage people to do is to think a little outside of the box, to not be afraid to play around and to have fun and to do something that is silly, even in a place where it’s serious.

And LinkedIn is a great example of a place where people tend to take themselves so seriously. So I think the more that you can be human and playful and fun, the more that things stand out. You definitely can’t and shouldn’t do what I did because, actually, one of my lasting contributions to society after me, they did make it so you can’t do that anymore.

Pete Mockaitis
Okay. Well, congratulations. Your ripple…

Chris Duffy
Thank you so much. We all want to have an impact, you know? We want to affect the generations after us.

Pete Mockaitis
…it reverberates. That’s beautiful. All right. And so it’s funny, I’m thinking I actually do follow a couple satire accounts on LinkedIn, and it’s really funny in terms of the difference, like the contrast when there is sort of a vibe, a tone, a subculture, a script. You know what I’m saying?

Like, there’s a little bit of a feel for how a LinkedIn post is “supposed to go,” like one-sentence hook grabbing you like, “I had to fire someone today.” Like, “Huh? What? Why? I had to know the rest, you know.”

Chris Duffy
Yeah, “Here’s what my wedding taught me about peer-to-peer marketing,” you know, something like that. It’s like, “What? What? What are you talking about?” You know, I think it’s true, in a lot of our lives, professional, personal, social, there are these like scripts that we’re supposed to follow or we think we’re supposed to follow, I think is a better way to put it, right?

Where it’s like, someone says, “Hey, how are you?” “I’m doing pretty well. Yeah.” “Oh, crazy weather,” right? Like, you just kind of, like, that’s what small talk is supposed to go like. And I think the thing about when we get into autopilot like that is that things just blur into the background. They’re not memorable and we don’t make real connections and we’re not actually our full human selves.

And, to me, the beauty of humor is that it lets us laugh about and acknowledge these, like, ruts that we get into that we don’t even realize are just like our habits. And the thing that I love about laughing with other people is, like, when you connect with them, you are actually genuinely connected. But also then people like you more, they feel attracted to you. And I don’t mean romantically attracted, like they want to spend time with you.

And there’s a lot of great studies that we can talk about that show that from a professional standpoint, if you are acknowledging things in a funny, humorous way where you’re willing to laugh at yourself, people respect you more even if what you’re acknowledging is your shortcoming.

They did a psychological study where they looked at people in job interviews. And people who acknowledged their shortcomings, like the things they didn’t know but made a joke about it, were much more likely to get hired than people who didn’t acknowledge it at all, or than who acknowledged it in a serious way. Because we like those people, we trust them, and we want people to admit that they’re not perfect, because we’re not perfect either.

Pete Mockaitis
Yeah, that’s really interesting. And I’m just speculating as to the why behind that. And it feels as though, if someone is capable of acknowledging their shortcomings in a fun, lighthearted way, it kind of gives a subtle implicit permission that, “It’s okay to talk about those kinds of things with me and maybe it’s okay to talk about a broad range of things with me.” And so there’s just a little bit more of a vibe of comfort and safety. I’m totally reading a lot into this, but this is how I’d speculate are the underlying kind of facets that make it go that way.

Chris Duffy
I think that’s totally plausible. And I think another piece is that if you’re willing to laugh about the things that you don’t know or that you’re not good at, it probably means that those are places where you would be able to improve as well because you’re open to feedback on them. You’re open to growth.

Whereas, the things that you get defensive about that are like no-go conversation topics, it’s really hard to then grow in those because you’re locked in to like your idea that, “I already know everything there is to know about this.” And none of us do.

You know, I’ll give you another study that I love psychologists at a number of universities looked at, they did a study where people evaluated job candidates. And so they didn’t know that the people they were evaluating were actually research assistants reading from a script.

But when they were evaluating these candidates, of course, everyone rated the people who were qualified more highly than people who were unqualified. No surprise there. But between the people who were qualified, there were two people who were exactly identical, except one of them spilled a whole cup of coffee on their shirt before they came in for the interview. And they said like, “Oh, my God, I’m so sorry, I spilled coffee all over myself.”

And that person, the coffee spiller, was consistently rated higher, was rated more confident, and was the one that people thought they should hire for the job. And, for me, the big lesson that I take away is not, like, if you’re applying for a job, dump a scalding hot cup of coffee on yourself. That’s not the lesson.

The lesson is that we have this idea that we’re supposed to be perfect, that people want us to be flawless and perfect and have no mistakes and just impressive. And, in fact, when you’re like that, people can’t latch onto you. They can’t relate to you at all.

People much prefer someone who is a little bit of a mess, but is still good at their job and good at the things they need to be good at. And so, to me, I think lowering the bar in that way makes you so much more desirable as a job candidate, but also just as a person to work with.

I mean, think about it, Pete, like I’ll give you an example. In your real life, I think there’s an intuitive example, is if you, Pete, walk into a room and you meet someone and he goes, “Hey, by the way, Pete, nice to meet you. I have a six pack. I make a million dollars a year. I give to charity every single day, and I work at a soup kitchen. And, by the way, both of my kids went to Harvard, and I think I’m probably going to be nominated for a Nobel Prize.”

Like, you don’t like that person. You know what I mean? At best, you’re intimidated, and more likely you’re like, “I hate this guy. I never want to see this guy ever again.” That’s certainly how I would feel. Whereas, if you meet someone who’s like, “Hey, can you do me a favor? I think that my pants might have just ripped, right?”

Like, you have a lot more to talk about, a lot more to relate with that guy, even though it’s a little weird because they’re not perfect and you’re not immediately intimidated and are jealous and have all these other feelings about them.

Pete Mockaitis
Yes. And what’s coming to mind right now is, internet personality. Her name is Elyse Myers and I just got her book.

Chris Duffy 
Oh, I love her.

Pete Mockaitis
She’s so delightful. It’s so funny, everyone loves her. That’s kind of where I’m going with that. I think her moniker is like the internet’s best friend or everyone’s best friend on the internet, something like that. And she’s repeatedly sharing her shortcomings, and her foibles, struggles with mental health and more, but she’s clearly very smart and very funny and very insightful and very personable. And when you bring those two things together, yeah, she’s the internet’s best friend.

Chris Duffy
Well, you know, I think the fact that you said very smart is actually, I think, really a huge and important piece here. I, for years now, have hosted a comedy show with the National Academy of Sciences, where we interview scientists about their work.

And, you know, I’ve interviewed Nobel laureates, I’ve interviewed MacArthur geniuses, all these really incredible people. And the number one thing that I’ve noticed is that people who are willing to say, “I don’t know,” or to be funny or to laugh at their own research, those are the people who are actually super intelligent, right?

Like, the people who don’t have a sense of humor and aren’t willing to admit that they don’t know some things or get defensive and blocked off, those are rarely the real geniuses. Because when you actually are exceptional at something, you have a level of confidence and comfort with admitting the limits of your own knowledge and also with trying to explain it simply and not just relying on jargon.

And so I think there’s a real piece there of, like, smart people, you can signal your comfort and your intelligence by laughing and by the things that you’re willing to laugh at and be open about.

Pete Mockaitis
Yes, I like that a lot. So can you give us maybe a story, an example, of someone in a professional context who upgraded some of their humor skills and found that genuinely helpful or transformative for their career?

Chris Duffy
One that immediately comes to mind is I talked to a former Navy SEAL, Joe Choi. And Joe was in very extreme life-or-death situations often. Even just the training for Navy SEALs can be really, really dangerous.

And when Joe was promoted so that now he was leading a team, he realized really quickly that the way to actually have people respect him, the way to have the men trust him, and know that in these life-or-death situations that he was someone they could rely on wasn’t to be super serious all the time.

The way he put it to me is that the best leaders that he had encountered as a SEAL, the best leaders took the work really seriously, but they did not take themselves so seriously. And so he found that he was able to motivate his team and to get them to be much more connected to him by being willing to laugh at himself.

And he told me probably the most dramatic laugh-at-yourself story I’ve ever heard, which is he was doing a training exercise where you were supposed to grab onto a ladder hanging out of a helicopter while you were in rough ocean waters.

And Joe managed to grab onto the ladder, he was going to demonstrate what to do. And he managed to grab onto the ladder, but he grabbed onto the wrong side. So instead of being able to climb up, he was actually getting dragged under the water. And he was struggling to breathe. He was about to pass out when he finally was able to pull himself up and flip over the ladder and climb up into the helicopter.

And when he got up, he was kind of gasping for breath and struggling. And it had really been a dire situation. And he says that all the guys who he’s supposedly leading are looking at him after this, like, scary and also, you know, not really like great example of how you’re supposed to do it. And one of the guys just said, “Wow, that was some real frog man shit.” And then they all looked at Joe and they saw if he would laugh, and Joe laughed really hard.

And he said that that became this moment for his group where they came back to it and it was like a bonding thing, but it was also a moment where they trusted that he was confident enough and honest enough about what had happened, that he was willing to laugh and acknowledge that he hadn’t done it right. And he said that that was something that really came back again and again in the group trusting him.

Pete Mockaitis
That’s really nice. Well, can you share with us, I think we like humor, humor is fun, the points you’re bringing up makes sense. They check out. So what are some things that we do with that knowledge? Do you have any sort of key pro tips or questions or ways you recommend we go forward and do more good humoring?

Chris Duffy
I will say that, I think, the biggest thing that people get wrong about humor is, I think, people often think that having a great sense of humor means you are the one on stage with the microphone or in the circle at the party or at the water cooler where everyone is around listening to your story, and you’re the one that’s getting all the attention.

And I would actually say that not that that’s not good humor, but the people with the best sense of humor aren’t always the ones performing it. They’re not always the ones getting the attention. Often, the people with the best sense of humor are the ones who are laughing the most. So they’re generously giving their attention to other people.

They are noticing things that are odd and unusual and delightful throughout their day. They’re laughing about it, even if they’re not sharing it with other people. And I think that when you broaden your definition of good humor and what good humoring looks like to include that kind of humor, you avoid a lot of the pitfalls.

Because one of the big things that people always say is like, “Well, how do I make a joke that doesn’t offend people? Or, what if I cross a line?” And the answer that I would say to them is the safest way that you can bring more humor into your life is to not be the one making the joke, to find people who make you laugh and to laugh with them. People love that, right?

I mean, like, the number one way to make someone like you is not to talk more, it’s to listen more. So I think if you can bring humor into your life in those other ways, that will really make you magnetic to other people because you’re having fun.

And so something I would ask you is, like, “Who are the people that already make you laugh? How can you spend more time with them? What are the ways that you are naturally laughing already?” So maybe one thing, one exercise that I really encourage, which is really simple, but I think can be transformative is just keep track of everything for a week that makes you laugh, or a month, however long, but write it down.

Write it down on a piece of paper or in a notes app on your phone. And what you’ll find is that just the act of paying attention makes more and more things surface, right? Anytime we direct our attention towards something, we find more and more.

And so having more of that humor and that laughter in your life is going to make you the kind of person who laughs more and has more fun. And that has all these benefits, both professionally and personally.

Pete Mockaitis
And I think that’s a theme that’s come up elsewhere in terms of like gratitude. If you are identifying things that you feel grateful for, or that turned out better than you thought they might in the course of the day, you are more inclined to notice more such things and feel more gratitude.

Chris Duffy
Totally.

Pete Mockaitis
So, in like fashion here, by taking note and attending to that which is funny, you’re having more of those good humor vibes going on.

Chris Duffy
I think this is kind of true of anything, right? Like, I talked to a guy recently who is a roofer. And he was just kind of telling me about, like, the good, what a good roof is versus a bad roof, and, you know, the kinds of roof that he likes working on and all that.

And then I was walking around afterwards, and I noticed all these roofs, right, these things that have been totally invisible to me. All of a sudden, I was like, “That’s like a nice roof. Oh, that roof needs some repairs.” And I have no ability to actually, like, repair a roof or know about it, but just having talked to someone who had a real passion for it and knew a lot about it, all of a sudden, this piece of the world that was invisible became really visible to me.

And I think the same is true kind of for anything, right? Like, if you’re always looking for professional chances to connect, you’ll find more chances to connect. And I think what I love about humor is that it offers us the ability to take ourselves less seriously, to make other people want to be around us, and to have a better time all at once.

Because it’s, like, without trying to think like, “I should have social connections.” If you focus on laughing, people want to be around you. You’re a magnetic person. And so just by noticing more of this stuff, you get those side benefits.

Pete Mockaitis
Okay. So, to do the noticing, I’m just going to pay attention. I’m going to write it down. Are there any key prompts or internal questions you recommend that can generate more of this good stuff?

Chris Duffy
So, for me, for more than a decade, I’ve been a professional comedian, both like writing late-night comedy shows and telling jokes and as a standup, and doing all sorts of other stuff. And what I found is that, actually, the most interesting part of comedy is not the performing.

It’s actually the generating the ideas and the noticing the material because that’s the part that I think anyone can do regardless of whether you perform or not professionally, right? Like everyone can have more laughter in their life.

And so the first thing that I would say is the seed of something funny is something that is a little unusual or off or different than expected. The gap between how things are supposed to be or how we think things are going to go and how they actually are is where comedy lives.

So one of the things that I would do is focus really small. The artist, Sister Corita Kent had a practice that she did where she would, literally, carry around a rectangular frame made of cardboard, and she would just, for her art, would hold up that frame and just look at what was inside the frame, everything else, narrow her field of vision, and that’s where she would find the art.

And I think you can, literally, do that for comedy. Just look at a corner of your house and just spend five minutes noticing all of the small things in that, what are the things that are a little off or a little weird or a little different. And you’re not going to find something laugh-out-loud funny right away, but you might find something small and odd that then you can think about and is the seed of it.

Or, a more relatable way, I think, is, Pete, when you go to someone’s house for the first time, and you go in their bathroom, you notice all sorts of stuff about their bathroom, right? You notice, like, “Where is the toilet paper? Is it hanging over? Is it hanging under? What kind of soap do they have? Do they have a hand towel? Do they have paper towels? Is there a pile of books next to their toilet? Do the books kind of seem weirdly wet? Is there a candle? Is there a little spray?” All this stuff in their bathroom.

But if you go to their house a few times, that fades into the background really quickly. It just becomes a bathroom. So the more that you can switch into that new bathroom mindset where you’re actually noticing the things in your life, the more that you can see the things that are odd and unusual and delightful. And that can really make you laugh.

So can we do an experiment like in real time rather than having this be a…?

Pete Mockaitis
Well, yeah, I was just about to go there in terms of looking at a corner for five minutes, how might that turn into some chuckles.

Chris Duffy
So, okay, so right now you’re in a hotel room, right?

Pete Mockaitis
I am in a hotel. I’ve had some flight cancellation action.

Chris Duffy
Great. So a hotel is kind of one of the most kind of stereotypically antiseptic places, right? Like, all the character has been taken out of it. And sometimes that can be hard to find something funny, but sometimes that in itself is the funniness, right? Like, that they’ve tried so hard to make no design choices, that it is bland in a way that is exceptionally bland.

So I would look around and be like, “Is there any art on the walls?” Hotel art is often funny to me, because it’s like, “What is the choice? Why is that the art?” What strikes your interest right away? Or what do you notice right away?

Pete Mockaitis
Well, what’s interesting is there’s these vases on top of inside-floating shelves that are tapered and they’re like pierced. It’s almost like it was a dagger that punched through this hanging shelf.

Chris Duffy
That is already incredible. I mean, that’s already really funny. Like, to think like the person who was like, “I know what they need. They need shelves that have been stabbed by a dagger. That will be our brand.” Like, that. And that’s a good example of, like, you could spend a week in a hotel room and never notice that, I think, but then you see it and you think about it.

Pete Mockaitis
Yes. And I like what you did there because, in a way, because what you said is like, “The seed is something that’s a little off, unusual, unexpected.” And that was that, but you didn’t bring me into the chuckle zone until you went that extra step associated with imagining the people who were discussing this, and deciding, “Ah, yes, this is what’s necessary.”

Chris Duffy
“This is our masterpiece.”

Pete Mockaitis
And that’s just funny because, but, really, who had this conversation? How did this come about? It’s genuinely silly.

Chris Duffy
Well, it’s also one of those things where, like, I think about this a lot where, like, when I’m in my own house and trying to find things that make me laugh. One thing that I always think is so funny is, like, on my washing machine, it says like, “Bright Whites. TM,” trademark.

And I’m, like, I love the person who was there who was like, “Listen, LG is going to own the phrase bright whites. That is our phrase. That’s really important.” And I’m like, “I think that that is not actually a trademark. Like, you might technically have that trademark, but Bright Whites is not memorable for anyone else. That’s just the white setting on my washing machine. I don’t think that you needed to trademark that.”

And, like, thinking about the person whose job that is, like this was probably like a series of interviews. There’s this, like, in an interview, they’re like, “I have a vision for naming the white cycle, something that we can own that will be like part of LG’s brand.”

And then they had a bunch of meetings and they filed paperwork and there was a lawyer involved. That kind of stuff, thinking about like the world behind the things that you’re seeing that are odd is often where I find things the most funny.

Pete Mockaitis
That is good, yes. And so, once again, it’s sort of like you’re noticing the thing and then you’re going deeper into it. I’m sort of imagining the lawyer there bumping into Bright Whites on like a GE washing machine, and said, “What?”

They just become utterly furious. And he, like, calls up their lawyer and starts cussing them out and screaming. It’s like, “If you think you can pull this stunt, you got another thing coming. I’m going to see you in court.” And they duke it out.

Chris Duffy
“You think you could screw me like this? Oh, you can’t. I will not allow this. No one messes with me.”

Pete Mockaitis 
Yeah, “Bright Whites. The trial of the century.”

Chris Duffy
It’s true. And that often is called the trial of the century. A lot of people don’t know that, but that was the real trial of the century. Something that is a trick that we often do to make something funny in comedy, in professional comedy, but I think you can apply this to your own life, too, is to take an observation and then layer on top an emotion.

So if you’re writing a joke, like one of the ways you can write a joke is, “I find it so scary that…” blank. “I find it so exciting that…” blank. “I am so happy that this thing happened.” Like, putting an emotion tells the audience how to feel about it. And often that, like, “I’m happy that this thing happened…” is what makes the audience laugh, because then you’ve set up like, “Here’s what I expect.” And then you can turn it in another direction.

And I think anytime we’re communicating, letting the people we’re communicating with know how we feel about something, and then the specific detail that we feel that about, that really lets them latch onto something really clearly.

So, like, “I am so confused by the vases in my hotel room,” or, “I absolutely love the way the vases in my hotel room were pierced by a dagger.” That is a sentence that people can latch onto emotionally.

Pete Mockaitis
Well, now, I’m sort of combining these things. I’m thinking about, if you have an emotion associated with a thing that is unusual, it feels like we’re in comedic territory, per your previous notion. So I’ll throw this out here. When I have all of my laundry done, folded and placed in the dresser, I feel a sense of power.

Chris Duffy
That’s great! Yeah!

Pete Mockaitis
Like, I am unstoppable. So I feel like that’s a little bit unusual to feel a really strong emotional association with these somewhat ordinary occurrences in life. So it feels like we’re in fertile comedic territory here, Chris, but nothing hilarious is coming to mind.

Chris Duffy
Oh, I think that is hilarious. I completely disagree. I think that you feeling like, “I am powerful and I am the master of my domain because I folded my laundry,” is so funny and so relatable and wonderful. And I actually think this hits at a thing that is, you know, talking about how to be awesome at your job.

You just naturally did this piece, which is you took that noticing and then you put it onto yourself. So now we’re laughing at ourselves and the fact that you’re like, “The most powerful I ever feel, the most in control I ever feel is when I finish folding a towel. That towel is perfect,” right? Like, there’s something hilarious about that, and also very relatable, but it’s also that you’re laughing at yourself.

And this, again, like from a professional standpoint, being willing to laugh at yourself, being willing to like give people that in, that lets people connect with you. It lets people not feel intimidated by you, but also be impressed by you because it is really impressive to have this kind of self-knowledge. And so I think you just naturally did it in a really beautiful way. And I think that’s genuinely very, very funny.

Pete Mockaitis
Okay. Interesting. So that’s funny for you.

Chris Duffy
This is an important thing. Like, it’s funny for me, but often the things that are funniest for other people are actually quite obvious to us. They don’t seem funny because it’s like, “Well, that’s just me being genuine and honest.”

But our authentic, genuine, honest feelings are often very funny to other people because there’s this gap between how we actually feel and how we’re supposed to feel, right? You’re not supposed to feel powerful and in control when you finish folding the laundry, but you actually do.

So for you, it’s kind of like, “But, yeah, that’s how I feel.” And for me, it’s really funny because I haven’t ever thought about it that way.

Pete Mockaitis
You know, you’re illuminating a decade plus mystery for me. And that is the TV show, The Big Bang Theory. I’m not really a fan. I don’t find that amusing. And so we got Sheldon who expresses his ideas in a very, you know, scientific-y, multi-syllables, big words, whatever kind of a way. And then the laugh track always hits.

And I’m just like, “The dude is just expressing his mind. This is not actually a joke at all.” And the funny thing is, in some ways, I, at times, can speak like him. I have a friend who’s like, “Oh, my friend is like Sheldon from The Big Bang Theory.” So, for me, it’s not funny because it’s not unusual because I am also talking weird in a way that’s sort of like Sheldon.

And maybe there’s a level of self-insight, self-awareness to be had from that. And that’s really intriguing in terms of, “They think it’s funny, I don’t, because I think that’s just how some people talk and that’s normal-ish, but apparently that’s very…”

Chris Duffy 
What is funny about Sheldon? He is a normal, attractive, intelligent man. He’s a totally socially normal, intelligent, attractive man. I think he is the peak of masculinity and I don’t see anything funny about him. Like, that is a really funny perspective to have, right?

Pete Mockaitis 
Yes, that is what… well, I wouldn’t call him masculine, etc. But, yeah, that’s intriguing that other people will find, and that’s just a good heads up. It’s like, “Hey, don’t get angry if folks are laughing at that. It’s not hostile. They’re just appreciating something that’s kind of special or unique or different about you, relative to perhaps the human norm.”

Chris Duffy
Yeah. Well, I want to unpack that, if it’s okay. I want to unpack that a little bit.

Pete Mockaitis
Sure.

Chris Duffy
On the one hand, sure, most times, I think, people laughing is not something to be offended by. It’s actually like a point of connection. But that doesn’t mean that people can laugh and be really mean in bullying you. So I think it’s possible to, like, you should be offended sometimes. So I think it really depends.

I think one of the things that is challenging about humor in terms of, like, the context that we’re in is there’s no such thing as a universal joke. There’s no such thing that’s always funny. Humor is always subjective. It’s always context-dependent.

So you strike me, I mean, we just met, but you strike me as like a confident, socially-adapted and successful person.

Pete Mockaitis
Handsome.

Chris Duffy
Handsome, charming, wealthy, powerful. You know, I could go on and on.

Pete Mockaitis
That checks out. It checks out.

Chris Duffy
But as a result, like, if we laugh about how you’re like Sheldon in some ways, I don’t think that’s hitting at some sort of like deep insecurity. And so, as a result, it is funny and it’s not bullying. But if that wasn’t the case, and you actually did feel like maybe you were getting, you had like a deep insecurity about how you fit in and that people were always laughing at you, and then we laughed about how you’re like Sheldon, that could actually be a really cruel, mean thing that wasn’t.

So I always go back to, like, “Is the laughter forming connection or is it pushing the person away? Are you trying to exclude them or include them?” And the kind that is really successful in our social lives, in our friendships, in our relationships, in our work is the kind that brings people in and makes people connect to us, not that pushes people away. And that’s always context-dependent. You can’t just have a universal role.

And speaking of that, like laughing at yourself is great in a professional setting, but there are these, like, lines. If you’re the leader of a company, people want to be able to connect to you. But also, you know, I’ve learned about the concept of selective vulnerability, which is like, if you’re a leader and you go into a meeting and you say, “Hey, everyone, the economics are really bad and we’re going to have to lay a bunch of people off, and I’m really terrified and I have no idea how this is going to go.”

Like, that might be really authentic and honest and vulnerable, but it’s not the right thing to say. People are going to be terrified and scared after that. Instead, you might want to be selectively vulnerable. So say like, “Hey, I’m aware that we are going into a really hard time and I just want to say, we acknowledge that and we’re going to figure out the way through together.”

So you’re still kind of acknowledging. You’re not denying the reality, but you’re not saying like, “I’m terrified and I have no idea what to do next,” because that’s not a helpful form of vulnerability. And even if that would get like a laugh in my context, it’s not worth the laugh.

Pete Mockaitis
And do you have any thoughts about humor in terms of boosting resilience, ability to bounce back from mistakes, failures, these kinds of things?

Chris Duffy
Totally. I think this goes back to, like, my core message, which is that we think we’re supposed to be perfect. And in fact, you’re not supposed to be perfect. The most resilient people understand that, like, a mistake is part of the process. For me, in my work, right, like if I go up on stage and I tell a joke and it bombs, no one laughs at all, if I say, “Huh, that means I’m a terrible comedian,” then I’ll never tell jokes again.

Instead, what I need to say is, like, “Oh, that was information.” And because the goal isn’t to have one perfect night of comedy, the goal is to, over time, get better and better, then I say, like, “Next time I tell that joke, I will try clarifying it, or I’ll phrase it in a different way.”

And I think that’s kind of true for all jobs, right? It’s, like, if you view it as an iterative repetitive thing where you can laugh about your mistakes and not feel like it’s indicative that you are some huge disaster or failure, then you get better and better because the point is to have the hundredth time be better than the first, not for the first to be perfect.

And laughter, I think, really helps us with that process because it takes away the judgment and shame and it makes it so that it’s, like, fun to share how badly something went and it’s fun to laugh at it rather than to think, “This is like a thing I need to sweep under the rug and not let anyone see.”

Pete Mockaitis
Well, Chris, tell me, any key do’s or don’ts, top things you want to make sure to mention before we hear about some of your favorite things?

Chris Duffy
Well, you know, the number one things I want people to do are keep track of things that are making you laugh naturally, pay attention to the world around you. And I would say that, you know, the number one other thing that you should do once you’ve done those is try taking a small social risk and sharing something that makes you laugh with someone else.

Don’t just have the same regular conversation you have every day, “Pretty hot outside, huh?” or, “Whoa, crazy weather.” Instead, try telling them like, “The other day, on the way to work, I saw a squirrel try and jump from one tree to another and it fell. Have you ever seen that? A squirrel missed the tree?”

Like, even if the other person doesn’t laugh, you’re going to have a different conversation than you would have had otherwise. And I think that is both the seed of connection, but also the seed of so much laughter and joy and comedy.

Pete Mockaitis
Beautiful. Thank you. What’s funny with that squirrel, you’re right, that that opens all sorts of avenues of conversation in terms of…

Chris Duffy
What does it make you think? There’s something boiling around in your head right now.

Pete Mockaitis
Well, yeah, I was like, “Well, was the squirrel okay? What happened afterwards? If you plummeted a long distance, you know, was it grass? Was it concrete? Like, did it get up and keep moving? Or was he done for?”

Chris Duffy
Oh, wow. Okay. You know, Pete, that is just indicative of what a kind, caring human being you are. And I will tell you, this is a true thing that happened to me. The squirrel I saw fell a small distance onto grass. It got right back up. But then it looked at me like, “You saw that. Oh, you weren’t supposed to see that.” And then it ran away.

So we just shared a really beautiful interspecies moment of, “Don’t tell anyone about this.” And here I am telling all of the listeners of How to be Awesome at Your Job, and that squirrel is furious somewhere, who is also, by the way, a listener. I could tell. He seemed like he’s listening to this podcast.

Pete Mockaitis
Yeah. Well, now that makes me laugh because I’m imagining a squirrel with headphones that are, you know, pushing in the squirrel cheeks, you know, even more to make them even more fat and squirrel-like.

Chris Duffy
Yeah, and he’s wearing some of your merch, right, like he has like a T-shirt with your face on it, and he says, like, “That’s nuts.”

Pete Mockaitis
Wow. All right, man. This is your life. Like, all day, your brain gets to play here.

Chris Duffy
As excruciating as that joke was and a terrible dad joke, that is my life. That is for sure.

Pete Mockaitis
All right. Well, now could you share with us a favorite quote, something you find inspiring?

Chris Duffy
I’ve been thinking about George Orwell talking about humor, and he said, “Every joke is a tiny revolution.”

Pete Mockaitis
And a favorite book?

Chris Duffy
One of the best books that I read is Octavia Butler’s Parable of the Sower. I think that’s a really relevant book to our world today and also just a beautifully written book.

Pete Mockaitis
And a favorite tool, something you use to be awesome at your job?

Chris Duffy
Oh, I want to say a microphone. That’s probably the only tool that I use regularly. And anyone who’s seen me try and do home repair will tell you this is the only tool that I’m safe to be around. So a microphone.

Pete Mockaitis
Well, you sound good, so I’ll ask what are you working with there?

Chris Duffy
Okay, this is a, hold on, I got to look at it. It is an RE320, an Electro-Voice RE320, baby. Oh, yeah, that smooth radio sound. Hello.

Pete Mockaitis
There you go. And a favorite habit?

Chris Duffy
I’ve been trying to do the 7 Minute a day Workout app. And when I do that, I feel a lot better and it only takes seven minutes. So that’s a good habit.

Pete Mockaitis
And is there a key nugget you share that really seems to connect and resonate with folks, they quote it back to you often?

Chris Duffy 
When people yell something back at me, it is often, “Sir, you need to move or out of the way.” Probably the key nugget, I think, from all of the work that I’ve done on humor is to be willing to laugh at yourself and to connect with other people through laughing more and taking yourself less seriously. I think even in hard times, finding something to laugh about.

And it could be as simple as watching a clip of outtakes from The Office, or going on Reddit’s contagious laughter Subreddit, or it can be an inside joke that you’ve laughed about with friends. But I think that idea that when you’re having a hard day, going back to something that reliably makes you laugh can transform part of the day, that’s something that I think is the biggest thing, and also kind of an obvious and intuitive one, but that we forget to do so often.

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Chris Duffy
ChrisDuffyComedy.com. That’s the place.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Chris Duffy
At your job, find the person who makes you laugh and spend more time with them this week. And then share something with them that made you laugh. I think that connection, connecting on something that’s lighthearted and fun is going to make that person want to be around you more.

And it’s also going to make them feel really honored that like you’re the person that laughs at them the most in a positive way. And I think that those connections pay dividends in ways that we can never expect professionally.

Pete Mockaitis
All right. Chris, thank you.

Chris Duffy
Thank you.