How to Make Your Writing More Funny (Taylor Tomlinson Interview)

Taylor Tomlinson is on the show, who's one of the world's top comedians with multiple [music] Netflix specials and also a book called Actually, Never Mind. Now, I love having stand-up comedians on the show because there's such a purity to their creative process. No matter what kind of writing you do, you can learn from stand-up comedians. Because what are they doing? Like any kind of writing, they're going out of the world, they're looking for ideas, they're writing down the good stuff, but the difference is they immediately have to go and perform. They're getting instant feedback. They go to the club and if the joke works, they say, "Wow, okay. I'm going to go refine that. I'm going to go improve it, make it better." And if it flops, they're like, "Uh-oh, there's nothing there." They go, "Whoop." They put it right under the covers, they never talk about [music] it again. But the thing that they know is that

quantity leads to quality. So, here's my conversation with Taylor Tomlinson.

Where I'll start is the process for you of writing jokes. Because I feel like comedy's this thing where you're watching people do stand-up and there's this art of having it feel loose enough that it feels natural, but also tight enough that it's got a good joke, the word choice is right. >> Yeah. I mean, my personal process, I'm not somebody who can just go on stage with like a vague thought and find it. Like there are people who do that, who like write on stage. I need like a notebook and some free time and the a day free of like expectations of me to sit down and write out subjects I want to talk about that I think I could talk about for a couple of years cuz that's how long it takes to get an hour together that's worth recording.

And then I just kind of work off of whatever subjects I find most interesting at that time. A lot of times it's subjects that I'm not sure how I feel. Like I've written a lot of jokes about having kids because I'm not sure how I feel about that right now and I go back and forth on whether or not I want them. So, that feels like a very rich area for jokes. Um it's like some of the oldest advice about joke writing. I think it's from like Judy Carter Comedy Bible books, too, of like just write down things that you have strong feelings about. Like write down everything that makes you angry, everything that you think is stupid, everything that you think is unfair, and whatever you have really strong emotions around is usually pretty fertile ground for lots of material, is what I found.

>> Tell me about going broad versus personal and kind of the the ebb and flow between those. You know, like I feel like you started off broad, then you go personal, broad, personal. >> Yeah, that's a great question. Yeah, I think with my specials the first one was broader, the second one was more specific, the third one was broader again, the fourth one was more specific, and then this one I'm working on now again is I like to swing back and forth. Um, so thank you for noticing that. But I think I always start specific, and then I sort of try to find what specific things about me or about my life or about my feelings where do where do I see those overlapping with like my friends, my family? Because like going on stage and talking about something that nobody else relates to, sometimes that'll work, but a lot of times it doesn't. So I kind of work backwards, I think, actually. I will talk about something that I'm feeling or

I'm going through, and a lot of times if people laugh, I know that they're also going through it. If it doesn't work, I know that it's just me, and that sucks. And then we take that to therapy. >> [laughter] >> But I I'm working on bits sometimes. If we've got like 10 minutes left, and I feel like we've gotten through a lot of stuff, I'm like, "You know what? Let's try some tags." I think that if you find something that's specific about you, more often times than not, it is more universal than you think, but figuring out how to present it on stage as a premise, I do think it is important to find a way to present it in such a way that is not like, "This is just my observation. This is just my experience." If there's a way that you can go without you know, overgeneralizing, which sounds completely contradictory, but >> Well, so tell me more about the specific, like where a moment happens, some observation, and you're like, I

just saw this. There's this thing that's bothering me that I just think is hilarious in what in some way or another. And it's like you're saying, "I'm going to write it down so I have some ideas of what I'm going to say." And then how does that become an actual joke of like, "Now I'm seeing it at the Comedy Cellar or the Stand or something like that?" >> Okay, so a joke I have right now in my act is uh that I was on a plane and I texted my buddy Dustin and I said, "There's a really loud baby on my plane." And he was like, "Oh, no." He's a dad. He's like, "Is he screaming and crying?" And I went, "No, it's laughing." And he goes, "That's not" I go, "That's the same It's just as loud. And actually nobody's trying to stop the laughing.

So, it's kind of worse in a way." And that was something that I wrote down like in a a phone note that I then worked on in a notebook and then took it on stage. And that was a joke that I was like, "I have no idea if this is going to work." Because it's not super likable to be like on the laughter of a child on a plane. Um but it practically it does work because I think it does surprise people and I do think some people go, "Oh my god, that's kind of true, actually." As opposed to like maybe, "Oh my god, I feel that exact way." Which is a different type of laughter. But the one that I feel that joke gets is more so like, "I never thought of it like that." Or like, "That's That is pretty crazy that you think that's just as bad or that bothers you just as much.

>> Why is likable important? >> Some people have like that persona where they are unlikable, but I still think people with unlikable personas, I think they're still likable on some level. Like some people can get away with that sort of like character on stage of like I'm a piece of I can't get away with it personally. So anytime I have a joke that's kind of like on the edge, and I do have a lot of them. I have plenty of jokes where I'm like admitting something about myself that is not super attractive, but for me at least, I do have to kind of work worry about likability I a bit I think cuz I think if you go too far and people start hating you and you're not fun to hate. Some people are like fun to hate. Some people are serving as sort of like avatars for everybody else's bad thoughts and negative impulses and like I don't really have that uh vibe.

I have a really just like round face kind of like nice Midwestern daughter vibe even though I'm from California. I think you got to know how you're perceived by people. I think that's a really important part of comedy is like figuring out what people see when you walk on stage so that you know which jokes are going to work best for you. I mean, ultimately you can do whatever jokes you want and whatever you can get working, but like I know people who will and I've done this too where I've thought of a joke and I tell a friend like you should try this because I can't do it. Like I can't pull that off, but I think you could. And I've had friends do that to me as well.

>> How much of the beginning of a comedy set do you feel like you're almost setting the setting or setting the rules for what's going on? I'll give you an analogy. So like if you watch a movie, the first 30 minutes is setting up the scene. Hey, these are the characters who are important. This is going to be kind of the vibe and the tenor of the movie. Uh these are some things that I'm setting up now, so I'm going to get a payoff later on. When you're doing comedy, how do you think about the sequencing of your your specials and what the job of like the first 10 minutes of a special is?

>> Mhm, that's a great question. I think the first 5 minutes are really important. I think the first like 60 seconds are really important. I think what generally ends up in a special, the beginning has probably been edited down in my case because people clap longer than is fun to watch when you start a special. So, while maybe in the room at a live show, it feels great to go "Thank you so much. Oh my god. So good to be here in this specific city." And then make like some local references and local jokes. That's not going to work in a special. So, it's different obviously if you're filming it. If you're not filming it, if I can talk about the city I'm in and like put us all in the room and make us all feel like, "Hey, like I know I'm doing a show that I do on tour and most of it is going to be the same as the show I do tomorrow in Raleigh, [clears throat] North Carolina, but tonight I'm here. I'm only going to say

this to you." And it's the same reason I like crowd work and I like to talk to the audience a little bit pretty quickly like in the first 15 minutes because I want people to leave my live shows feeling like they saw something that only they're going to see. Even if it's again, the bulk of it is what's going to end up in a special. I think having like a moment up top of recognition of like, "I see you guys. I know where we are. I know where I am.

I'm not on autopilot." goes a really long way. >> So many of the funniest bits I've seen from you are the crowd work bits. Where like something happens and then it just kind of unfolds. How much of that is like a child of what you've written versus just like, "I'm live. I'm switched on and I know how to steer the conversation towards something funny. >> Well, it really depends. I mean, I personally I like to do crowd work at my live shows, but I do it in a very structured way, which is I usually sprinkle it throughout the show every like 15 to 20 minutes.

I ask the audience a specific question that is related to the hour. So, it's generally something that I do want to know. Like, I think that's kind of the key to crowd work. Like, if you don't want to do it and you don't like it, you shouldn't be doing it. But, if you do like it, like there are so many different ways to do crowd work and engage with the crowd. And And I have a lot of people who come to my shows who are a lot like me who don't want to talk to me at all. And I would never speak to a live entertainer in front of that many people. That's insane. I can't believe anybody ever talks to me or like >> Sounds horrible.

>> No, to like yell out your secrets in front of 3,000 people, it's insane. So, anytime it like starts to go sideways or weird, like I I try to be pretty friendly and open. And like, if it goes weird, I'll deflect or like I'll make it about me. Or like, I never want anyone to feel bad or like they regret talking to me. And I also don't want to encourage people to heckle or like scream out or like disrupt the show. So, the way I do it is I go, "I know there's some people in here who probably want to talk. And I do enjoy it and I want to talk to people. How can I do that in a way that feels like safe and like the show's not going to get away from all of us, but like we could still have a genuine moment." And if like nothing funny happens, like for every crowd work moment I've posted, there's been 20 that were just like, "Oh, cool.

Okay. And you got married for how long?" "All right, great." And then you just move on. Like, the way I like to do it is I like to ask a question, find someone who wants to interact with me. Sometimes it goes somewhere, sometimes it doesn't. It's why I'm so meticulous about writing out my set and like having clear transitions so that I can get back into the hour really seamlessly and so I don't get lost cuz I don't really know how people write individual jokes and then just like order them.

>> What about Mitch Hedberg? >> Yeah, I can't do that. Oh my god. I I really don't know how anyone does that without like a set list or anything. I need to have like topics that flow together so that I can remember all of it and so that people hopefully feel like I know what I'm doing. I think that's another to your point about like sort of setting the table of a show. I think making people feel comfortable immediately is really important and is something that I had to learn really early because I started when I was so young and when you go on stage in high school, everybody's nervous cuz you're a child and they should be nervous. You shouldn't be up there. So, I had to like really early on be like you got to move the mic stand confidently. Like you need to put yourself You can't go up in like sweatpants. Like you need to look like someone who knows what they're doing and is a professional. I think just like

making everyone feel at ease and like you're not going to on anybody for participating, you're not going to let the show go off the rails and you're not going to make anybody nervous by like melting down or being bad at your job.

>> What is the thing that you love about stand-up? Is it nailing the joke? Is it hearing laughs? Like there's so much validation that comes from that. What is it? Like what is the thing that you're like, yes, I live for this. I'm married to the game. >> I think what I love most about it is I love that you can write something at 4:00 and at 8:00 you find out if it's good or not. Like I like the immediate gratification of it. I also really liked writing the book and being like in a blanket for months and months going, we'll find out if this sucks in 2 years. Like I liked that, too. Very different. But I really like how quickly you can work writing jokes if you're willing to get on stage a lot.

And I I just love that moment of like you wrote something down, you think it's funny, you don't know if it's going to work, but you know it's funny to you and you know it's something that's true to you and getting a big pop off of that. Think of how good it feels when you say something to a friend and you're like, "Can I just say one thing?" And they go, "Yeah, go ahead." And you go, "I think that that person kind of sucks." And they go, "I think that person kind of sucks." You go, "Oh my god, I know." That's how it feels when the whole audience laughs at something a thought you had that isn't like maybe the nicest, kindest, most refined thought you've ever had. You know what I mean?

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What have you taken from the memoirs of comedians like Tina Fey, different memoirs that you've read to look at, I don't know, how comedians have lived their lives? >> I feel like Tina Fey's memoir and Mindy Kaling's books like are very, very joke-dense. Like they're super bit-heavy. And I remember when I read Amy Poehler's, it's also got tons of jokes in it, but it was a little more earnest, which I remember at the time really resonated with me. And I love all of these books equally, but I think Amy Poehler's came out a few years after those two. I think it's in her introduction, she talks about how hard it was to write that book and how she like fitted in between filming and travel and kids and all this different stuff. And I remember thinking like okay, even when I ever write a book, it's going to be really, really hard.

And I need to just know that. When I was pitching this book and we were talking to publishers and I was working with my editor, I remember kind of at every stage of the process people kept saying to me like, you know, writing a book, it's a lot of work. It's really hard. It's It's a lot of work. And I don't blame them cuz I'm a comedian. So, of course, I'm sure they were like, is this a Is the clown really going to write the book? Cuz does the clown know She has to do the homework?

So, I was like, hey, I want you guys to know, I don't expect this to be super fun all the time. I know it's going to be tough. I still really want to do it. It's like a childhood dream of mine. Nobody has to be worried. And I also think because I read her book I was so prepared for it to be so painful that I was pleasantly surprised, which is how I try to approach everything in life is just like expect the absolute worst and then be pleasantly surprised when it's not quite as bad. Cuz of course there were moments that were like so difficult about writing it, but I think overall I really enjoyed the process. The The hardest part was honestly just being done with it and having to sit and wait for it to come out and like knowing I couldn't make any more changes to it. It has to be done at some point, right? And that's how stand-up is too. I mean, stand-up specials I feel that way every single time. Like I'm like, "This is

what I have right now." And if I keep tinkering with it, at a certain point you'll start messing with it and doubting yourself and making it worse. And so you have to like hopefully hit that sweet spot where you've got it like totally super tight and honed. But it you're not like bored and it's not stale.

>> In what ways can you be funny in a book that you can't be funny in stand-up? And in what ways can you be funny in stand-up that you can't be funny in a book? >> Well, you can't really do any act-outs in a book. I mean, the audiobook a little I guess, but you're not you're not going to coast by on a funny face in a book. There are things in my act that are purely physical. Not very often, but every once in a while you're like, "Well, this is just like a silly movement." Um this isn't really that great a line. Uh but with the book, like yeah, you really just you can be a lot wordier in a book. Like with stand-up I'm always trying to get the most ideas into the least amount of words. And so with the book, to go from this sort of like, "Okay, you need to get this sentence as short as possible."

to "No, expand on that and actually tell us every feeling you have about that subject." It definitely took me a minute because I was great at the editing part of the book. The editing part I was like "Cut half of that." And my editor was like, "No, no, no, that's a whole chapter." And I'm like, I I'm just saying I don't think we need it. Like I'm very good at editing because of stand-up, because I'm always trying to cut it down and get things shorter.

>> And then with being funny in a book, what do you think that you're able to do that stand-up doesn't give you? >> You're allowed to take your time a bit more. With stand-up, it's like you need to be getting a laugh every 20 seconds. And with a book, you can be like witty for a little while, and then earnest for a little while, and then funny for a little while. But like stand-up, you need to be funny the whole time. There's no like, "Oh, that was kind of clever." Like no, you have to be funny. People have to be laughing. They can't just be like, "Mhm."

"Mhm." And with a book, you can sort of like you don't need people to be physically doubled over laughing at every point. Like I I don't usually laugh out loud at books that I think are very funny because it's just not that type of experience. Someone's having a private experience with it as opposed to like watching a special with their friends or like going to a live show with their family or like their date. So I just think it's like a totally different audience that you are writing for. You're writing for somebody who's alone in bed or in their car or, you know, on the train or whatever as opposed to like here's something that you're probably consuming like in a group in a theater or a club or something.

>> Um I saw that stack of books that you had, that just insane stack of Bird by Bird and Good Writing by Anne Lamott. What did you take from those books? And what are the best ones? What are the best books of writing advice? >> I mean, Bird by Bird is the best one. I mean, it's the one that I've gone back to the most because the part of that book where she talks about how perfectionism makes you think that if you're perfect, you're never going to have to die, but you are going to die.

and everybody else who like wasn't as obsessed with perfection as you is going to die, too, but they had more fun than you. I swear to God, I think about that every single day of my life. And that's just like good life advice. It goes beyond writing. So, I think that's like hands-down the best one. And it's the one that I read in high school. I mean, it's the one that you know, you go online, if you look up books about writing, that's the first book that comes up, right? Like, every single time. I think the thing that's helped me the most by having all of those books, cuz I have not read all of them, is just reading about other writers talking about how hard it is for them to write, and how hard it is to publish their work and be perceived and have other people like consume what they've written, because I mean, I don't know how anyone puts anything out without having someone else as an example admitting, like, "Yeah,

no, I feel scared and bad every single time." Like, I'm never like, "And that's great. And that's perfect." Like, the fact that every single writer across the board seems to say like, "Yeah, no, I always think it's garbage, and I just put it out anyway, and I I hope for the best, and I'm always getting better, and you know, you just kind of live with that fear." It's like how people talk about having kids where they're like, "Yeah, no, you're terrified all the time, and you just live with it." And you're like, "Oh, okay.

Well, if it never goes away, then maybe I'm not a total fraud, or like, you know what I mean?" So, I don't know. That's the thing that's been most helpful for me.

>> What did you need to learn about how to be a better comedy like a better comedian through the course of your career? Like, what do you think that you didn't understand early in your career? >> When I first started doing stand-up, I was really self-deprecating on stage to like an unhealthy degree. And at a certain point, probably around 21, 22, I was headlining on the road a little bit more and kind of starting to get into like doing 5 hours a weekend territory by myself.

And I had girls coming up to me after shows repeating back to me negative things I said about myself, whether it was my appearance or my relationship status or whatever, whatever, my personality. And they would say something like, "Well, if you're annoying or ugly or whatever, then what am I?" Like there were women who were kind of like seeing themselves in me that were going, "Oh, we would be friends or we have a lot in common for the first 25 minutes of my set, and then I go on a long rant about how I'm trash, and then that feels bad to the people in the audience." So, I think I actually an important thing I learned that really changed the way I write about myself, especially, is like on yourself on stage, I mean, it's a delicate balance to strike, right? Because people are paying to watch you, and people like your stuff because they relate to you. And so, if you on yourself too much, you're

kind of like, in a roundabout way, insulting your audience as well. That's not how you keep an audience. [laughter] Like nobody wants to go watch somebody who is just talking about how insecure they are as well. So, and I think it's kind of funny to be over to swing between overconfident and self-loathing on stage, and then you sort of like even out somewhere in the middle, which is I think what I do now is if I do a really self-deprecating joke about myself now, I then try to balance it by going, "And by the way, I know that I'm not entirely XYZ. I also have this going for me or here are the ways I'm better at You know what I mean? Like I'm trying to write jokes right now about being an older sister cuz I have three younger siblings and I'm trying to strike that balance of like I'm the older sister so I take care of and I'm always right and also I'm really annoying and overbearing and that sucks.

And so I think you just have to like it's it's similar to knowing how you're perceived on stage and how people are receiving you and relating to you. There's a responsibility in how you talk about yourself and how that's then like metabolized by your audience. So I think that was a big like that was a big moment for me and something that changed the way I approach joke writing.

>> One thing that really stuck out was obviously you've had a lot of jokes about difficult things that have happened in your life. But then there's a level where you do that and all of a sudden it's like, okay, why is this girl doing therapy on stage? >> Right. Right. Right. Right. >> And so how do you you write jokes that's like not therapy? Why are you just spewing your dirty laundry here? Versus on the other side like, wow, this this Taylor's really being real and open about some of the things that she's gone through and kudos to her for finding the humor and like I lost my mom too when I was a kid or something like that and now we relate and connect.

>> I think audiences can tell when you are not over something. I think that sometimes I've brought things on stage and I go, I'm totally healed. I'm good. And the audience's reaction tells me something different. I go, oh, I guess I'm not. I guess I'm not okay. And sometimes they know before I do. I'll think that I'm totally fine. I mean some of those jokes I did in my second special about losing my mom young I had been doing for years and they worked sometimes and then other times they didn't work. Not much about a few of those lines changed over the years, but they started working better once I was in a better place with it. And once I had gone to a lot of therapy, and I had worked on it. So, I think people can sense when you are in a healthy place with something as opposed to when you're just going up there and kind of like melting down. You know what I mean? Like people know when you're in control of the ship and when

you're not. >> Can you walk me through how a joke that you love has changed? May- maybe it's a word, maybe it's the setup, maybe it's a sentence. >> I mean, the jokes about losing my mom in Look at You >> And that was your second special. >> my second special. There's a whole section that started as probably like I don't know, 60 seconds of jokes about losing a parent young that then grew and grew and grew. And part of what helped that whole chunk to work, which ended up being like a 6-minute chunk what helped that work is towards the beginning after the first few initial jokes I sat down and I was like, here's what's going to happen, everybody. We're going to talk about this for a minute.

And just so you know, I'm fine. Like look how successful I am, which is not something I could have done in my first special. I couldn't have done that when I was a younger comic because I wasn't successful yet. But once I was successful, nobody's worried about me. And now they can see the humor in the jokes I've written because it's not being ruined by them saying that I'm sad. >> it kind of works. >> Well, yeah, I think it's really funny to be overly confident and say the thing [laughter] that you're not supposed to say, which is like, "Hey, I made it, so it's okay. Like maybe it's fine." And it was like also a real it's like the root of a real feeling I had, which is like "Yes, you lost a parent really young, but who are you to complain? You're still privileged in so many ways." You know what I mean? So, it is coming from more somber feeling inside of me, but I do think it's funny when people are

like, "I'm doing pretty good in this area. Yeah, over here that sucks, but again, just just swing between like self-pity and just like insane confidence, I think is very funny. And it completely helped and made the whole bit like one of my strongest chunks of material ever because I was just addressing the tension in the room that then allowed everybody to loosen up and laugh for the rest of the 5 minutes. >> Mhm. How do you just carve out the space

to actually write and do the work? I was talking to a friend who went to Hasan Minhaj's studio. I'm hearing this second-hand, so I'm not sure that all the details are right, but he basically said, "What I do, I go in there, no phone in my office, no Wi-Fi. My whole team knows that when I go there, I print money. Like that that that room is where the money is made. It's not the other stuff. Like that room is where it begins." And my sense, the takeaway that I got was he's just has to be in that room and cultivate the space, the time to be there and do good work.

>> Yeah, I mean, that was another way that the book was totally different than stand-up because when I need time and space to work on stand-up, I need to go to like a coffee shop or a cafe or like somewhere in public that I can like people watch and I have sort of like Yeah, like I can't write jokes silently at my desk in my apartment. Like that's never worked for me. I need to be like out. I need to be in a place that I can walk around and, you know, listen to my sets and try to tag things I've already written.

And then hopefully try them out on stage that night or that week. But with the book, it was like go to my office, like shut the door, turn off my Wi-Fi. That's how I felt about the book. I was like, everyone needs to leave me alone because I have to focus on this. But, I was surprised cuz it was such a different process than stand-up. I kind of went into it going, "Well, I know how I'm going to write this because I've been writing jokes, and it's pretty much the same." But, even like the window of the day that I was the most productive >> Time shifted earlier, yeah?

>> Yes, exactly. Like the book I was like, "Oh, I have to wake up at 9:00 cuz I work best between like 9:30 and 4:30." >> Like a normal human being. >> Yes, and it's like if I'm writing stand-up, it's like I'll have the slowest morning imaginable, and I'll start writing at like 3:00, and then I can write until the evening, and it was like, I don't know what it was, but when I was working on the book, I really couldn't work on it unless I was editing. Once I was in the editing phase, I could work into the evening, but when I was just on that like first draft, and like I trying to generate, I was like fried by like 4:30.

It was so weird, and I had to get started earlier. >> With comedy, there's kind of this just generally there's this myth of the tortured artist of like the artist is going to live this crazy life and do these crazy crazy things. Oh, yeah, like let's rip shots, go have a bender cuz like that's where the good stories will come. In what ways do you think that's true, and in what ways are you like you're talking about professionalism earlier, you're like, "No, you got to be a professional. This is business."

>> I mean, look, I've never been someone who can get super drunk and party. Like, I'm not super fun, but I'm jealous of the people who are. Like, I'm jealous of the people who take those risks and do crazy cuz they have awesome stories as a result of it, and those stories turn into like 20 minutes of a stand-up special. And so, I'm very jealous in that respect. But, I think that that same behavior that can get you some of those amazing stories that nobody else has can make it really difficult to do the job which is really hard on your body traveling that much and staying up late and like not always eating the best. You're eating like club food when you're younger and coming up and like trying to make money and trying to save as much money as possible. So like yeah, you're going to eat chicken tenders at the club for free. Like I don't know how anybody gets through those early years headlining when they're like binge

drinking all weekend. I I personally couldn't do it. So you know, it's a trade-off, right? And some people are great at both. Some people can drink all weekend have crazy stories spend like Monday and Tuesday recovering and then do it all again. I'm not one of them, but some people can. >> How much do you think of clips as you do your specials, write your jokes? >> Well, now I think of them a lot. My first special when it came out I think I got on TikTok like right after it came out. I wasn't even posting clips like a social media person I had was like we got to post clips and I was like okay, if you say so.

So I mean when I was young, it was like you wanted a late night set. You just wanted like a YouTube video that you could point to and go I'm a real comedian. The clips thing I feel like really started I don't know what 2018 2019 maybe. 2020 obviously it like really blew up because it was all we had. And so I think the people who were resistant to like clipping up stand-up before COVID afterward realized hey, this is kind of just how the internet is now and this is how we sell tickets. And like I'll do I'll do shows in clubs when I'm working stuff out where I go I'm just going to see what happens tonight. Like I'm going to do more crowd work on this one. This I I'm feeling that way. And then the next night I may not want to and I may just want to work on material. So I just go off of how I feel about it because if I force it I never get anything, you know, like you can't really go like I'm going to get a bunch of

crowd work clips tonight. It's like it either happens or it doesn't. The thing is now you kind of have to film everything though in case something happens which is exhausting and annoying. And I do miss like back in the day when you like didn't have to think about it all but I'm also so grateful be a stand up in a time where you have the internet and you can grow your audience and find an audience that's so specific to you. I am thinking about it but I'm I'm prioritizing the hour always.

>> You were talking earlier about writing at coffee shops, restaurants, whatever it is so that you can people watch. Tell me about that. Like how you go from looking at people to then getting something into your joke. >> Well, I mean I feel like this is so common with like comedians, writers of kind of every kind but like I'm trying to eavesdrop on people. Like on planes like I know do you really just have your headphones in and nothing's playing cuz you're trying to get closer to people in like a thrift store? Yeah. So you're just trying to like >> content all around us.

>> content all around. So I mean I'll I'll follow people around a bookstore with airpods in cuz I'm like they don't someone they don't look at them. They're not going to know. If I'm just home alone staring off into space I don't I just don't think of jokes that way. I can think of other things that way. I can think of ideas for stories or whatever. I can't come up with jokes super easily if I'm just like alone. I can go over a set that I already have alone. I can remember my jokes if I've had like a couple weeks off where I didn't do the hour and I need to get back into it.

That I can like sit down at my desk and listen to it and write it down and maybe tag some stuff here and there, but as far as like oh, I want to like sit down and write jokes, I need to be like out and about. >> And you do the reviews of your sets how? So, you film everything and then you kind of walk around, you'll be home and you'll just be listening to yourself? >> Yeah, I just do voice memos on my phone. So, I do I don't film every show, but I record every single one audio. So, I usually listen to it on planes or like walking around mostly. It's It's easier to listen to your set when you're walking around as opposed to like sitting on a plane just like going, "Wow, I really thought that joke hit harder, but I guess not." It never sounds exactly how you think the show went, right? Like they which is why it's important to listen to your sets because sometimes something went better than you thought

and sometimes things went not as well as you thought. >> And what are the things you're listening for? >> Laughs, groans, gasps, silence. I mean, just the full range of reaction, I guess. So, that the right kind of laugh. You don't want people who are just clap dirt. When people are clapping cuz they agree with something you said as opposed to laughing because it was funny. Like that's something comedians talk about a lot. Or like getting woos instead of laughs. Like it's okay if people are cheering while they're laughing, but if they're like just cheering, you kind of sometimes have to go, "Okay, I don't know about that necessarily.

That might just be a good point you made and it's not quite funny yet, so." >> Like a lot of different kinds of laughs is what you're saying and certain laughs are like, "That's what I'm going for." And others you're like, "No." >> Yeah, and it's like how you structure your set, especially when I'm getting to a place where I'm going to uh film it and put it out as an hour. I am thinking about clips, I guess, but I'm mostly thinking about it as a cohesive hour. You know, you you don't want to have like a lull in the middle.

You want every joke to be strong, but not every joke is going to murder as hard as every other joke. Like there are some jokes that you think are really strong, but it might get like a slower laugh where it takes people a minute to like really wrap their head around what you're saying. And that's not going to be the same as that sort of like machine gun laughter you get on bit that's just like bam bam bam bam bam, you know what I mean? Like if you're going to be up there for an hour hour 20, it does need to kind of like ebb and flow, otherwise it's going to get repetitive. And I think it's easy even if all the jokes are really strong for people to sort of check out cuz I've been there. I've watched an hour of someone doing jokes, and at a certain point you kind of just like get distracted because it's all one note, you know?

>> I mean, that's what a good album has. >> Yes, exactly. >> a good album has these different vibes, but there's a coherence to it.

>> Yes. >> How did you go about developing your voice as a writer as you were working on the book? >> I think in writing the book, I learned that there are ways to say what you want to say without sharing absolutely everything. And I think stand-up has really helped me get there because I think when I was younger, I would write a joke about anything, anyone. I kept nothing for myself. Everything was material to me. And luckily, I've sort of outgrown that and realized that relationships are more important than getting a clip.

But I felt that way with the book, too, where I was like when I first went into it, I kind of went, "Oh my gosh, do I have enough to say? Do I have enough to write about that's interesting?" And throughout the writing process, I was like, "Oh yeah, there's plenty of ways to say everything that you want to communicate and say all the things that are important to you and reveal all the things that are personal to you and say a lot about who you are and where you come from and and why you are the way you are without giving everyone every single detail because especially as a comic like you're doing podcasts all the time you're doing you know stand-up every night like I have spent a lot of my adult life oversharing and I've learned how bad it feels when you say something you can't take back and so I'm glad that I did not write this book before I reached that point in my life because it's a lesson I have to

kind of keep learning over and over but I feel good about where I got with this final draft. >> Well, this is interesting cuz I think it's really important creatively to be sincere to be authentic to be vulnerable. So let's put those three words out there. Let's assume that they're important. >> Yeah. >> What you're saying is that does not mean that you need to share absolutely everything and that you can get those three virtues without just disclosing all of these things and I wonder if a lot of people see it as a stew when actually you can kind of split up the dishes.

>> Yeah, I mean it's similar to crowdwork clubs, right? Like you can do crowdwork in a city and not post it. Like you can have a real moment with a crowd and it doesn't have to go online. It doesn't have to be monetized and your soul is the same way. Like you don't have to cut yourself up into slices and figure out all the different display cases for them. Like it is important to keep some things just for yourself whether it's just that the memory is too painful or too private or even like too positive. Like there are good things that I didn't put in the book because I was like I don't want a bunch of strangers to know that about me. I don't need anyone with 20 bucks to have access to that part of me.

>> I'm going to read a few sentences from these pages when you're talking about writing. I want to hear you comment on them. So, the first is, "When I first started doing stand-up, it felt like I had an endless supply of premises because I hadn't tried and failed enough to know a bad idea from a good one." >> I think that when you're first starting out, it really feels like, "Oh my god, the world is my oyster. I can write a joke about anything."

And then, as you spend more time in the comedy world, you realize like just how many ideas have already been explored and that you do have to work a little harder to be original. And it's why it's so important to start from a very personal place cuz if you're starting from a place of "This happened to me." or "I said this." or "This was said to me." it's not going to be as like derivative. But, you have to know like what's already been done so that you can differentiate and have your own perspective on things and put your own spin on things and come up with new ideas. And that's only gotten harder and harder as the internet has become stronger and stronger. I've learned that many times over the years. But, yeah, when I was a teenager, I Anyone who starts stand-up at any age, the first 20 minutes you write is just going to be a bunch of stuff that has probably already been done a lot better. But, you

have to write that stuff first. You have to like get all of that out. >> Yeah, I think it was Ed Sheeran who He said that writing is kind of like a faucet where you turn it on and there's a bunch of dirty water that needs to come out. And the muck just needs to go. But, the answer isn't, "Oh my goodness, the water's dirty. Let's turn off the tap." The answer's "Turn on the tap, keep the water flowing, and then there's clean water that's been backed up that comes out after." But, there's a lot of muck that comes out at the beginning.

>> Yeah, absolutely. I completely agree with that. >> In the beginning, I spent a lot of time watching and reading about comedy, whereas nowadays I try not to consume too much so that I don't fall victim to comparison or absorption. There will be a season where you need to educate yourself and then the time will come when you need to step back. >> Yeah, no, I think when you're first starting out it's important to watch a lot of comedy and learn from the greats and learn what to do and what not to do and hopefully save yourself some time learning some lessons. But then yeah, at a certain point I mean you keep your eyes on your own paper. Like you have a general idea of what people are doing, you watch what your friends are doing and you know, if there's a comic you really like that you've always liked, yeah, of course like check out their stuff. But for the most part like it also just becomes work, you know, to be watching

stand up and surrounded by stand up. So I try not to watch much stand up because I don't want to get discouraged and go, "Oh my god, everybody's so much better than I am." Like I'm I'm more prone to that than like absorbing other people's ideas. But I think I'm very prone to Oh my god, everybody's like so much better than I am. It's like really a lot better than me and what am I doing? And I And then you're just on stage like doubting yourself for an hour and that's not good doing anybody any good.

>> The other thing I think we both came to the same conclusion here, which is I've done I don't know like 120, 140 of these interviews. I've done so many and I wish I had anything more insightful to say about the writing process than you just need to freaking write. Like you say, "I've read virtually every how to write book on the market and they all say the same thing. You just have to write." If you feel like you have nothing to say, then you have to go live. And it's like you just need to do the thing. It's like running.

>> Yep. >> You could read a bunch of books about running technique, heart rate, you know, get a whoop band, check your HRV, but if you're not actually putting in the steps, just nothing's going to happen. >> Yeah, 1,000% and it it's Yeah, and stand-up's really like that, too, and unfortunately, like stand-up is, you know, even further than that, right? Where it's like you can't get better at stand-up just writing. You have to just write and just perform. So, uh whenever anybody's like, "Oh, I've written hours of jokes." I'm like, "Well, you don't know if they're jokes if you haven't tried them. You've written a lot, that's great, but you don't know if it's a joke yet until someone laughs at it."

>> You were talking earlier about not consuming other stand-up, but for you, how much of finding jokes is a collaborative thing? Like, do you hang out with a lot of other comedians? >> Oh, yeah, that's a good point. I mean, I have like my closest friends that usually open for me on the road and like we'll bounce ideas off of each other a lot. Like, my best friends, Sophie Buddle and Dustin Nickerson, are on the road with me most often, I would say.

And Sophie also was the head monologue writer on a show I did and she's just like brilliant. She's incredible, like such an incredible joke writer. She and Dustin have, you know, helped with so many of my jokes. I mean, that's kind of like the best part of getting to a place in your career where you can travel with your friends is like now you guys don't have to make coffee dates with your notebooks to be like, "Okay, what do you think of this?

Is this anything? Do you have any ideas for this?" Like, cuz that is I will still do that if we haven't seen each other in a while, but it's so much easier when you're on the road for a weekend to hang out all day, walk around the city, get breakfast, go to the green room, spend hours backstage just going like, "Here's something else I wrote down in the middle of the night. Do you think this is anything?" Okay, now tell me what you have or like, "Oh, I watched your set last night." Like, that's really fun to watch a friend's set consistently because you don't have to worry about absorbing it, because, you know, you're not going to watch your friends set over and over and over and like forget you saw that and go, "Oh, I had an idea." That's not going to happen. You get to just enjoy your best friend performing.

And then also, you get into a rhythm with each other where you can like sort of tag each other's jokes more easily and you can write in each other's voices and I think those are the times that you end up saying like, "I thought of a joke for you. It's not going to work for me, but it would work for you." is when you're that close with somebody and you're working with them that consistently. >> You keep using the word tag. Why is that such a core part of the way you think about comedy?

>> Oh, I guess cuz like I will go up on stage with like the first punchline or two, like sort of like the anchor. And once I have one, then I can riff a little bit. Like then I feel like I can feeling safe enough to drift into the deep end of the pool as long as you can like hold onto the side. Is how I feel when I have sort of like the scaffolding of a new bit. And then when you try those wild lines after, like the ones that work, those are tags.

Like it's you tagging your own joke. And then the ideas your friends give you of like, "Oh, and then you could say this." Like they're just like the lines at the end of a joke that then become the entire bit.

>> Are there movies, shows, stand-ups, that stand-up specials that you've seen where you're like, "I've taken major inspiration from them." And if so, what did you take away from them? >> Like when I was a kid, we were really religious and sheltered. So, the comedians that we were listening to were clean comedians. So, like Brian Regan and Kathleen Madigan, like they were on repeat for me as a teenager. And those were two people that at the time were doing what I wanted to do, which was touring theaters as a stand-up comedian without like a hit sitcom, which is really hard to do back then. Now it's much easier because of the internet, but back then there wasn't a lot of people who could do that. So they were like huge inspirations for me in that way. I know everybody says Fleabag, but I think Fleabag is such a perfect example of a show that is dealing with grief and trauma and self-sabotage and

self-loathing and also is incredibly funny at the same time, and knowing that all of that can exist and that if you can pull it off, that's often the art that stays with people, I think. At least it does for me more so than like "Oh, that was silly for an hour." It will stay with me longer if it made me cry and then laugh and then cry again. >> Tell me if I'm putting words in your mouth, but hearing you talk about Fleabag, I almost get the sense of that show does something that you didn't quite realize was possible.

>> Yeah, I think that's true. I think that was true for a lot of people when they watched it. I feel like that show is really unlike anything else and I think I've seen other shows like try to do what it did and nobody can quite figure it out. That like breaking the fourth wall I have not seen that done successfully since Fleabag, have you? As opposed to like there were a a lot of sitcoms doing that like mockumentary style. I feel like we figured out how to do that and that's been done successfully over and over, but the breaking the fourth wall thing I don't feel like anybody's quite cracked it in the same way. And it's so deceptive, right? Cuz it seems like the easiest thing in the world to just turn to the camera and be like, "So here's what's going on." And it's actually so hard to pull off.

>> Last question. I know that The Getaway Car by Ann Patchett, you've talked about a lot. What is it that you took from her? >> Well, I wrote I wrote about this through my Substack recently cuz I just got on Substack, but it goes back to what we were talking about about writers talking about how hard it is for them to write and how inspiring that is as somebody who is considerably less talented and experienced. She talks about how writing down her ideas on the page feels like pinning a butterfly. Like she's like talks about her ideas being a butterfly and she has to kill her friend in order to get it down on the page in the same way you have to like kill a butterfly to pin it down.

And it's like it's so sad. It's such sad imagery, but it's like so it's truly how it feels when you have like all these ideas swirling around your head and you're like, "Oh my god, when I write this down it's going to be incredible." And then you get it down on the page and you're like, "Oh, it just looks terrible now. Why can't I get it to look like there's a line where she says, "I am always" I'd have to look, but she talks about how she's always disappointed the in her talent and how she like can't write the way she wants to write and how she knows like it should be written and she's like, "I'm always just like mourning my lack of talent." And you're like, "That's Anne Patchett. Who feels like that?" And you're like, "If she feels like that, what hope do the rest of us have?" And then you go, "Okay, well, if someone like that feels that way, too, then maybe it's okay to feel that way and

maybe it's okay to doubt myself and push ahead. Like it's so helpful to read writers who are willing to admit things like that because it makes you feel less crazy and it it stops you from abandoning projects because I think those feelings of self-doubt and those feelings of like I can't get what's in my head on the page in a way that I think I should be able to. If you're alone with that feeling, you might think that you don't have anything worth saying or you're a garbage writer. So, when somebody who is objectively fantastic voices a similar feeling, you go, "Okay, well, maybe I should keep going then."