Shtick To Solo

SOLO 73 Jen O'Donnell | Shtick


Happy April Fools’ Day. This episode gives you a glimpse into Peter McGraw’s other life as a business school professor and humor researcher. He invites two comedians, Jen O’Donnell and Shane Mauss, to discuss how to apply lessons from his recent book Shtick to Business to help make your life of single people even more remarkable. 

Listen to Episode #73 here


Shtick To Solo

This episode gives you a glimpse into my other life as a business school professor and human researcher. I invite two comedians to discuss my book, Shtick to Business with the intent of making your life as a solo more remarkable. It’s a fun conversation that coincides with April Fool’s Day in the relaunch of the book. I hope you enjoyed the episode. 

Our first guest is Jen O’Donnell. Jen works in development for unscripted television and is a stand-up comedian who runs a show in LA called The Ladies Room. She also calls me every so often, which I greatly appreciate. Welcome, Jen. 

I’m excited to be here. Thanks for having me on. 

This is your first time. 

It is.  

it doesn’t feel like that.  

I’ve been a guest of yours on other things, so it feels like home. 

We are joined by a returning guest, people are like, “Not him again,” Shane Mauss. Shane is a stand-up comedian, adventure, and science enthusiast. He visits universities around the world and interviews researchers for a science podcast, Here We Are a close friend of mine. Shane is a frequent contributor to SOLO and a special contributor to my second book, which we are here to talk about. Welcome back, Shane. 

Am I the most common guest? Have I made the most appearances? 

I’m afraid so. 

You’re stuck with me. We talk on the phone all the time. 

We do. 

I’m a Chatty Cathy. 

The reason why Shane and my life are intertwined A, and B, Shane says yes. C, I already lost A, B, and C. He does the homework, so we’re in good shape. Maybe last minute, but he does the homework. It’s April 1st, 2021 and I am relaunching my book a year after unsuccessfully launching during a pandemic.  

Remember when I tried to warn you. 

I do love a good, “I told you so.”  

Even if it’s in my direction and it is an, “I told you so.” 

In all fairness, you did send an email to your network that said, “Am I launching a book at the worst possible time?” You were looking for an answer. 

Here’s the thing we don’t know whether it was the worst possible time or if it’s the worst possible book. We’re going to find out with this relaunch. 

I have a friend reading it now that they didn’t tell me they’re buying it or anything else. They wrote me one day and they’re like, “I’ve been reading this book, and I’m getting so much out of it more than I was expecting to.” Where you screwed up as you had me, a comic, attached to it and people have so little respect for comedy that it’s like, “Business lessons from the world of comedy.” There are a million wonderful gems in your book. 

There are and a lot of them are from you, Shane. I appreciate it. There’s tons of takeaway and there are a lot of laughs in there. The one that’s sticking out to me is, at one point, you said that you always carry a notebook and that’s what comics do. It’s like a hammer and a nail. If you have a hammer, everything looks like a nail and you’re like, “That’s also why I don’t carry a gun.” 

We’re going to have some fun. A lot of the episodes are fun, but this one will be especially so because we’re going to take lessons from Shtick to Business and we’re going to apply them to single living. 

That’s what we’re doing. I’m ready. I’m excited. 

I’m tentatively calling this Shtick to Being Solo. They’re making faces.  

He loves the word shtick more than I do. As a title, absolutely perfect but as a word to hear often, “Ugh.” 

A good stick is a good shtick, if you will. I also like Think Funny. I like that a lot.  

I probably would have been the second choice for the book, which is, To Think Funny. I’m working on a project with Jen to turn the book into an online course.  

I was trying to plug that real low-key. 

That’s coming.  

Shane, maybe you can get in on that one. 

I’d be happy to. I love online courses. That’s how I educate myself. It’s mostly through online courses. 

Can I ask you what you’re up to or what you’re doing? 

No. We don’t have time for this.  

One course. 

Send it in the back channel. 

Robert Sapolsky has the best one I’ve ever seen and it’s free on YouTube. 

People cried and clapped at the end of that one, which no one has ever done at the end of one of my classes. Not simultaneously.  

Not yet.  

Here’s what we’re going to do. I asked each of us to take three lessons, apply them to the world of being single, being solo and we’re going to try to make this book fit into a SOLO show awkwardly 

We should probably be clear on what this book does. I shouldn’t do it because it’s mine and it sounds like me plugging it. 

Why don’t I do it?  

That would be great.  

SOLO 73 Jen O'Donnell | Shtick
Shtick To Business: What The Masters Of Comedy Can Teach You About Breaking Rules, Being Fearless, And Building A Serious Career

That’s the lesson in the book that you have someone else bringing you on stage. Let’s implement our teachings and learnings. The book is taking all of these things from the world of comedy. It’s not a book about how to be funny, although there are laughs in it and you might even pick up a thing or two. It’s specifically from the journey that so many comedians, improvisers, sketch writers, stand-up comedians have to go on. From open mics to writing, to cooperating with a team of writers and things like things that can be applied to things like advertising in business to think tanks and innovating new ideas, that’s the shtick. 

I always say, “Serious business lessons from the masters of comedy.” I have two masters of comedy on the line. What is your first lesson? 

The Reverse It, the setup, twist, and punch lesson in the book, which is such a clear and maybe even overused comic device. I hesitate to say that it’s used so often and I’d say quite successfully to spin things and help take on the alien anthropology look at life. Businesses can do this as well. There were fantastic examples in the book. Please help me out, Pete. What was one of the great Reverse It was? 

One of my favorites is the dumb phone. 

The idea that as every other phone is getting fancier and fancier, one company was able to stand out by saying, “Some people still want a damn flip phone and don’t want to mess with all the gizmos,” and made a killing. Comedians do that with jokes quite a bit and I’ve done that in relationships, though inadvertently. Typically, I had been a serial monogamous person. I was in for about 2.5 year long relationships nearly back to back. What I learned in that is I’m not good at marriage material, which is good, because I don’t want to be married, but I’m also not good at living with as material.  

There’s a section in the book called Bugs to Features, which sticks out a lot to me. A lot of comics use this. We get on stage, we point out our flaws, we make fun of our flaws and that helps us come off as authentic, vulnerable, it’s brave and funny at the same time. In relationships, everything that makes me bad at the long-term thing like it’s hard to pin me down. I’m always traveling, always spacey, and innovating. I always have, and you can ask Pete, every time I talk to him, I have some new project I’m working on and launching and also big ideas.  

Some of them pan out and there’s a lot of failures as well and that’s hard in a long-term relationship, but in a shorter situation, it’s exciting. It means you get to travel around with me. You get to go behind the scene at clubs and have them. The first time that you’re a lady and the guy you’re with is the headliner, they come in, bring you free drinks, food and cater to your every need and all. That’s an interesting life experience that’s novel. When you live with that guy, you’re traveling around, and now you’re at another crappy Chuckle Hut. 

More free chicken nuggets. 

Listening to the exact same joke over and over again. Two out of the four long-term relationships were comedians. To me, I was like, “Writing partner.” What happens is it starts like that and over time, every woman I’ve ever been with eventually is like, “You are obsessed with work. You don’t stop and it’s too much. I don’t want to hear your joke ideas. I’m done with your joke ideas.” 

That’s why Shane calls me a lot. 

I’m bipolar too, so I have that bit of mania that a normal person would do well to be a little skittish of because there are lots of big pitches all of the time. That will wear old over the course of a few years but when you’re new to me, and you get to be on the ground floor of all my new, I always have new exciting projects I’m launching and you don’t have to stick around to see all the failures, terrific.  

I love the Reverse It and that’s why I started the book with it. Essentially, the idea is you produce an opposing perspective. Everybody’s going one way you go the other way is a great way to make comedy to create punchlines, premises for movies like Trading Places, and so on. It is also a good way to think differently about the world. If I hear you correctly, Shane, while there’s a lot of people who are like, “I suck at dating, but I’m good at relationships,” you’re the opposite of that. 

I always beat myself up so much because I can testify that I fall in love quicker than any human being on Earth. When I meet a girl, first off, if we become intimate, it’s over. I’m making plans on how we can move in together. My evolutionary psychologist from Martie Haselton is always like, “You’re the lesbian that shows up with the U-Haul on the first date. That’s you.” I wondered why I failed so much at that and now I know. I need the shorter. I’m done for a year.  

You look at those as successes. Dating, to me for a long time, especially a blind date or a Tinder date, was like, “Cool. A show.” This guy has to listen to everything I say for the next two hours and I get dinner.  

When I was dating and starting comedy, it was workshopping stuff. The problem was, when it’s Tinder, and when it’s things like that you are definitely seeing people. There’s overlap. It’s like, I went on a date with this guy. We’ll go out again. I did go out with that one guy two weeks ago and I would forget that I had told them certain bits if you will. I have a tendency to exaggerate a lot so my nightmare is always, they are not only, “Am I telling the same story, but the joke is a little better than last time. 

Turn the volume up. 

I’m a road head. My career shifted some while, especially with COVID but for years, I was on the road, going from club to club. Five shows, usually two shows Friday, two shows Saturday, and sometimes three shows Saturday. You’re traveling, you’re tired and you’ve told these jokes 100 times. Sometimes you go, “Did I use this one on this show?” That’s what your relationship is. 

The real ones, friends, and relationships it’s like when somebody tells you there’s spinach in your teeth. The real friends are like, “You already told me the story.” I’m like, “Thank you so much for stopping me there.” That’s a real friend. 

I wonder if having multiple sex partners uses this?  

Have you made that move? 

Did I use the flick already? 

I want to clarify one thing before we get to Jen’s. I can’t wait to know what Jen’s is. You talked about Bugs into Features and I’m a big believer in this idea. We see our weaknesses all the time and we lament our weaknesses. What comics do is they turn their weaknesses into strengths and this is useful for singles. I’m a lot like you two, which is I’m good at dating. If you’re good at dating, why don’t you lean in and enjoy dating more? There are so many people who are like, “I hate dating. I hate the apps. I hate this experience.” If you say, “No. This is a little show. We’re going to be going to. We’re going to have a good time.” I’m not workshopping ideas, but I do enjoy conversation, so it’s an opportunity for potentially good conversation. 

I like that Jen, as a comic too, that idea of using it as a show is so funny because one, it’s a captive audience. They have to be. They can’t walk out. 

They’re not going anywhere. 

I know I’m doing something right if a couple of people walk out each show like one table. You want one table to leave. You don’t want a bunch of people to leave and you don’t want everyone enjoying. If they don’t know you, you don’t want everyone to like it because you’re doing something basic.  

Something’s not right then either. 

You have a captive audience and they have to give it their best laughs too. 

 Also, to tell me how brilliant I am. They have a goal in this exchange and so do I, which is to workshop my material. 

There’s this to make out with you. 

I will also say mainly wins for me. This was to say, the beginning of my stand up career to where I would be doing Bringer shows and I would casually be like, “Come to my show. Great. Here’s where it is,” or they’d follow me on social media so they would show up to a show. I have butts on chairs and they don’t know each other. They don’t know that they’re both there to see me. It was a good 3 to 4-year system.  

I’m wondering how many times I’ve gotten caught up in this grift. 

It was grift for sure.  

I want to point out one thing in the book, Maria Bamford does this. I don’t know if you know this, but she’ll land in a city and she’ll put out something on Twitter and she says, “Buy you coffee. I want to run through my set with you.” She meets with a stranger in a strange land, buys them a cup of coffee, and works through her stuff right there to warm things up and to check it all out.  

She did that on Twitter and I responded, I was like, “Yes, please. I’ll workshop your jokes with you,” but she wanted a normal person. 

She does like the normies. She told me that it’s such a flood of excitement to know that people want to be there and how cool it is that somebody wants to connect like that intimately and that you can give that opportunity to somebody. That’s why I went on so many dates. 

At this rate, this will be the longest episode ever. Let’s get to number one of Jen’s. What do you have for us, Jen? 

I did have Shock to the System was my first one. 

I was like, “What is that one?” 

You’re like, “Is that in the book?” Luckily, I have bookmarks, so I pulled it. I was ready. I said, “Did I interpret this wrong? You would like me to call this Incredibly Credible. I’d like to figure out exactly what you mean by that as I tell you more. 

The idea in that lesson overall is the value of being authentic, truthful, and being able to express weakness. In the world of business, you always want to put your best foot forward. Show them everything’s great, we’re the best to highlight the positives and sweep the negatives under the rug, and so on. Comics do the opposite of that. 

What I honed in on was an example in the book, it’s Domino’s as a pizza company that basically comes out, and instead of trying to convince people that they should order the pizza, they straight up admit, “This pizza sucks. We’re going to fix it.” It reminded me of a breakup and in that breakup having those honest conversations. I have two good friends that are married and they call these No Bullshit Dinners. No bullshit is saying the truth. In a breakup, I remember looking at each other and being like, “Neither of us are better because we’re together. The idea that we could improve wasn’t possible.  

Like a Domino’s pizza, this can’t be the same product in this relationship. This was a while back, so I probably didn’t have the emotional skills yet and he didn’t have the emotional skills yet to work this out as adults so the result was rocky. Looking back, I thought, the best shock to the system in what this ended up being was I eventually had to change my entire life. The relationship had to end but I looked around my apartment and I was like, “I can’t live here anymore.” I looked around at my office and I was like, “I’m going to still do this work but I need four new walls to look at because of those associations.” For me, in order to break free of that and to stop that pattern, I had to not totally change it but to reverse course. 

Tear it all down. That’s what Domino’s did. 

Domino’s is one of them but Pizza Hut is another. The personal pan is good for the show. 

We are accepting sponsors. The feedback that Domino’s had was she needs the crust to taste like cardboard. Not only did they admit that it was that pizza sucked, they basically started fresh and changed everything as a result of that, which I thought was good. It’s now incredibly successful, popular, useful, and not cardboard taste. 

Shane, you had mentioned comics looking at these principles in business and whether it’s working with a team of people or being on stage in front of people. I also think that there’s a lot of value in how comics have to organize the infrastructure of their life. There’s a lot of similarities because comics are entrepreneurs and we are our own business. I ended up taking a lot of those lessons, “These jokes that I’ve been working on for a year, I hate and I don’t like, so what do I do?” The answer at one point was to throw everything in the garbage. I still don’t know if those ingredients of that crust come back. It’s possible but in that moment, we have to have a completely new product. We, meaning me and the business of Jennifer O’Donnell. 

What underlies this is this notion of authenticity pointing out your flaws so they’re on display with Shane. He’s already mentioned his challenges as a long-term relationship person, being bipolar, and so on. Essentially, the idea is that there is something endearing when someone owns their shit so to speak. It’s like, “This person is honest. I can trust them. There’s something refreshing about it in a world where everybody has their guard up and so carefully curating and manicuring their brand and their identity.” One of the things I will take listening to you for the SOLO reader is to stop trying to shoehorn your life into some other person’s wants and desires and the world’s wants and desires. 

Into the wrong packaging.  

First off, I do this, I read the YouTube comments. Most people are like, “Don’t do that.” The ones where they’re like, “This guy’s gay or whatever.” That’s hilarious that this twelve-year-old boy got a kick out of saying that. Those don’t faze me at all. It’s like, “This guy sucks.” I don’t care but when someone is like, “He used like so many times in that,” I go, “I sure did.” That sucks to feel that and I think, “I’m going to take down the number of times I say like in conversations by 10%.”  

It’s going to require a little more effort. I’m going to need to think about it every time I’m going to use the word like. I’m going to say, “He said,” instead, or something like that. It takes a little extra effort, especially now that I’m trying to do it. The other thing is, sometimes people meet me and listen to my podcast so much that they know everything about me and they’re like, “Is that weird that I know everything about you and you don’t know anything about me?” I’m like, “It’s so great because I don’t need to explain who I am.” 

You’re already at the 400 level. This is great. We’re talking graduate work now. That’s excellent. Thank you for doing your homework. 

We’re ready to talk about convergent evolution. I don’t need to talk about all the other basic 101 evolutions. Here’s what I’ve been thinking about lately. You’re on board. 

That’s a good segue into mine. Mine’s a big one. It’s s Chapter 3, Create a Chasm. I like this one a lot because it’s something comics do all the time. You have to do it in order to be successful. It’s not sufficient, but it’s necessary. Moreover, good businesses do it. Shane already demonstrated it a little bit earlier when he talked about walking a table. In the best shows, there are some people in there who are not exactly thrilled. Certainly, people outside of the show are clearly not happy but as long as the audience and the people you care about as a comic are laughing, you can live a good life as a comic.  

The problem is when you try to make everyone laugh and when you try to be something for everyone. I use this example in a world that wants hot tea or iced tea. If you serve them warm tea, in order to make everyone happy, you make no one happy. You can see this in the world of business. One of my favorite examples in the book is Barry’s Bootcamp. It’s this hit-based fitness class. It’s basically working out in a dance club. The music’s crazy loud. You’re bathed in this red light, which makes you look fabulous because the red light washes out all of the blemishes. Men take their shirts off in the class and women are barely wearing anything, to begin with, and it’s frankly, not a scene for everyone. 

It’s way too loud for me. I went to the front desk, asked for earplugs and they gave them to me. If I’d asked them to turn the volume down, they would, they would have told me to take a hike. Barry’s is successful because it’s not popular to me but it’s popular to Jake Gyllenhaal, who goes to Barry’s classes and to all the LA, New York, and London types who like to be seen. Applying that to the world of being single, being a solo person, it’s a perfect example because if you choose to walk this path, if you choose to celebrate being single, you’re going to disappoint other people. You might disappoint your aunt who’s dying for you to couple up. You’re going to disappoint some friends who want you to be in lockstep with them in terms of their engagement, having kids, and vacations with the families.  

Getting divorced eventually. 

If you follow the path that is right for you, you’re going to make some people happy and you’re going to make other people happy but if you try to make everyone happy, you’re not going to make yourself happy. My example of this is my friend Julie, who’s a previous guest and guest cohost. Whenever there’s some event happening, and she has some new friends who are going to meet me, right before they walk in, she says, “My friend Pete’s going to be here. He’s not for everyone.” I love that she does that because it’s true. I may say something or do something during the evening that might be off putting to some of these people but it also allows me to not have to tamp down and hide the person that I am.  

Everybody should come with that caveat. Nobody is for everyone. This trio in particular, maybe more so than others. 

Those people stop reading. 

There is one reader, that’s why it’s called SOLO. 

That’s insightful. The social pressure of being single is exactly that. There’s so much social pressure and exploring the aunt, why she wants you to be with somebody and exploring the friend, why they want you to be with somebody. As much time you dedicate to that it’s important for you to explore, I’m talking to myself now, why you want to be or why you want to not be. 

I want to jump in because I had this conversation where a woman that I’ve dated her friends and family liked me but they don’t like me for her, if that makes sense. I’m described by some of them as a commitment-phobe. That’s such an interesting bias that exists because I could describe them. I could be like, “Why are they commitment addicts? Why are they addicted to commitment?” To me, the issue is it’s important to ask why where the default is commitment and to deviate from it is seen as a negative. Wouldn’t it be wonderful if it was like toppings on ice cream where some people like M&Ms and some people like sprinkles? It’s not like, “You’re a sprinkles-phobe not having sprinkles.” That’s a stupid example but the idea is either of these things is good, as long as it matches what you want in that way. 

There are people in relationships that build on a relationship and grow stronger over time and there’s a whole lot of people that are like, “I’m stuck now. This is how life goes.”  

That’s interesting. That’s the first time that’s popped through my mind. If you are single, often, you have to better yourself often. If you are in a relationship, you probably end up in a stagnant place for much longer. I talk to my girlfriends all the time and the ones who are single, it’s always this conversation of working on yourself. I’m like, “Are people in relationships doing that?” Probably not. That’s a huge appeal to single life and to not being partnered. It’s because you’re constantly taking online education courses, for example. 

Or making them. The way I think about Create a Chasm, especially if you embrace your solo living, you’re going to disappoint some people. If you simply say, “I’m happy being single, and I never want to get married or unhappy being single, and if it happens, that happens,” people are going to find that distressing, and other people are going to find that exciting. 

I went to see The Book of Mormon in Schenectady, New York and it was in this massive theater and there were a bunch of blue hairs with season passes that didn’t know what The Book of Mormon was. An exceptionally controversial, the most controversial musical there has ever been. 

If people haven’t seen it, I study comedy, I’m pretty impossible to offend. Shane is a great friend, so that’s an example of how hard I am to offend. I sat there and I was like, “I can’t believe they did that.” 

Me too. As a comedian who spent the first few years, as a shock value-ish that was a lot of my hook. I watched it and watched a bunch of people that didn’t know what they were walking into. The reason I bring it up is because sometimes that table leaving adds to the comedy that people are like, “Not everyone in this room is going to like that one.” There’s something about being a solo person, too, that has that same vibe, where it’s like, “This person isn’t vanilla. This person isn’t for everybody.” 

I’ve been developing swagger around it. I used to make excuses and be on the defensive. I won’t go on the offensive. I won’t throw stuff back at people but I’m not going to apologize for it. 

This exactly gives people tools to go on the offensive and conversations because I do think that there is so much infrastructure in society for partnerships. It isn’t just sprinkles. It’s the parfait cup and I do love a parfait TCBY. 

Especially on a first date. 

Dessert, if it’s going well. If we want to do another 10 or 15 we’ll go for a parfait. It’s important to have those conversations because there is going to be so much pushback. The world is built and designed for two. It makes people uncomfortable when other people are alone because it’s a scary thought that people aren’t thinking enough about. It doesn’t have to be. I’ll be on the offensive for you and I’m engaged. 

You know what you’re getting yourself into. 

Not really.  

If you read this blog enough. 

I thought you meant marriage. That’s why I said, “Not really.” 

Let’s keep this moving. Shane, you’re up next. Number two. 

This transitions nicely into the idea of cooperating. There’s a section of the book about forming teams and writers’ groups when I first started comedy. I should get back to it because I dropped many of the habits that I used to have that were so fruitful for me. I used to get together with comics all the time and put together writing meetings and stuff. In being solo as it’s not necessarily the norm, there’s so much pressure to partner up, have married friends, and have your couple friends and all of that. The notion of even having a solo podcast like, “I want to collect a bunch of people that don’t like collecting.” I know that’s not quite the point.  

Pete and I talk about this quite a bit, the idea of friend love. I have so many friends that I love that I have such great relationships with that I talked to all the time. Being someone that spends a lot of time on the road, I also call a lot because I drive a lot in the before times. I’m getting old and still consistently lose friends to relationships. It changes things quite a bit. I have so many female friends and some of them I’m super attracted to as well but this is one of the great things that COVID has done. We’re in different cities. We’re not going to have sex. There’s a global pandemic. It might be two years before I can hug a person or whatever.  

Every time I was in a relationship, all my female friends, I was never able to hang out with them as much. There’s always jealousy and stuff that came attached to it. I cherished my friends so much more and to think about how much of that you lose, when you decide, “I’m going to spend all my time with this one person.” It’s such a network. You can hope that kids are going to care for you or whatever when you’re older but it is true that it’s got to be scary for Pete to think about me checking in on him when he’s sitting in a nursing home but it’s not kids are some sure fire investment to do that. 

I have a good friend of mine from grad school. Within the first couple of years of meeting, he was like, “Jen, is it cool if you’re the person who decides to pull the plug on me someday?” I was like, “Done. Hell yes, Ned. I will do that for you.”  

I’ll pull plugs. Pete’s a great plug puller.  

You’re going to go out in first-class with me. 

I could see him being rational about that. 

Shane, we’re going to Switzerland when you’re ready. I’ll fly you in business class. I got lots of miles.  

Pete is ten years older than me and going to live longer without a doubt. 

When TV is ready, I will pitch Pete McGraw’s death flight show. It’ll be a beautiful story. The world isn’t ready but they will be. 

First of all, it’s interesting you say this. I’m going to work backward from these things. I do have a designated plug puller and her name is Janet. We already haven’t worked out. I’m going to finance it when I’m ready to go. We’re going to go to Switzerland, first-class. She can stay as long as she wants afterward. She brings my ashes back. It’s all set up. She’ll outlive me. 

My fiancé and I have decided that we’re going to The Notebook. I don’t want to give away any spoilers here. It looks like Pete’s never seen The Notebook. That’s our plan.  

What is the movie where they drive off the cliff and hold hands? 

Thelma and Louise. That’s my other favorite movie. 

I want to back up to the lessons cooperate to innovate. In it, we talked about lone genius, whether it be in comedy or business. When you look at the lone genius, what you often find is the guy behind the guy, the guy behind the gal, the gal behind the gal, or the gal behind the guy behind the gal, etc. I like the example of Chappelle’s Show. Neal Brennan co-created Chappelle’s Show. He was a writer on every single one of the sketches, including some of the best comedy sketches in the world, even though it was called Chappelle show. Regardless of how amazing Dave Chappelle’s talents were, he needed Neal Brennan to do that. 

He needs him back. He’s put out well over an hour of “comedy” and I haven’t heard a single joke. 

I keep watching and I’m like, “He’s saying some interesting things but there’s nothing that I’m not laughing at.” 

Neal is an incredible joke writer. Where am I going with this? I say this time and time again solos need a team. You find this in a variety of areas of comedy. For example, improv. You need someone else to set you up. One of my favorite sayings is from Del Close, one of the fathers of improv. He says, “We are all supporting actors.” The friend love, as Shane was talking about, we’re all supporting actors. If I’m trying to make Shane a better person and Shane’s trying to make me a better person and you’re trying to make Shane a better person and vice versa all the way through, we all have a chance to become better people. At certain moments, we can especially shine like on an improv stage.  

What’s cool about this, you two as stand-up comedians, can appreciate this, is even the most lone wolf stand-up. The road warrior, the person who’s out on the road, they live alone, they travel alone, and they may even keep to themselves a lot of the time. Even that person has helped. They have other comics who help them punch up jokes and give them feedback. They have an audience that helps them make their material funnier. Every previous audience makes the experience of the subsequent audience better. They give feedback in that way. I’m a big believer in the idea of having a team.  

Even that American idea that you can build up yourself, it’s a myth. We need each other. Unfortunately, we’ve learned that the hard way.  

I also love that there’s not the same expectations for monogamy. There’s not a lot of jealousy going on with friend love. I felt a little like, “Why does Janet get to pull the plug? I want to pull your plug.”  

At first, I thought that you said, “Jen.” I was like, “I got two now?” I was nervous. Shane, you can have it. 

I did a series on Making Remarkable Friends. I defined what makes a friend and what makes a friend a good friend. One of those things is antijealousy or what we call compersion. The idea is that a good friend celebrates your successes and commiserate with your failures. They’re not trying to outdo you. They don’t get jealous when they see you succeed. That is not normal in a lot of relationships, especially when it comes to sexual jealousy. In the poly-community, the idea is if one of your partners has great sex with another partner, you celebrate that, “My partner felt great pleasure,” rather than seeing it as some risk to the relationship. In the same way that when Shane or Jen succeeds, I want to celebrate that because I want to see my friends flourish.  

Do you know what I want to do? I want to take a female friend to a sex club with me. It’s like, “Jen, let’s you and I go in here. Let’s pretend to be a couple. Let’s find a hot couple and then pretend we’re swapping. We both get to bang hot people.”  

I’ll do it if I can pull your plug someday, then I know we’re friends. 

I like the opposite sex. Friend love is also special, everything about it.  

This came up in the Solo room at Valentine’s Day that Pete had in the Clubhouse. Culturally people know about Galentine’s Day, which is girlfriends. It’s the day after or the day before Valentine’s Day. My friends and I would do that. We would meet for dinner. We do a FaceTime. To me, it is a tragedy that doesn’t exist for men. In the Clubhouse, we came up with Palintine’s Day. Maybe there’s something else. I keep saying the word infrastructure, I don’t know why. I’m running for the Solo office. There needs to be infrastructure for male friendship and for things like that to enhance your solo life. 

Also, straight male-female friendship is such an eye-opening thing. I have female friends that are dating. 

It’s a cheat code for dating. 

These female friends dream of having their gay friend or whatever that they workshop like, “I can get inside of a guy’s head.” It’s like, “No, I’m better. When you’re dating somebody, I can tell you what they’re thinking and when you’re overthinking it.” You can help make sure, like, “I shaved my beard before putting my face on a dating profile.”  

There are trade-outs. It’s comedic translation services.  

Let’s turn to your next one, Jen. I want to recap. We did reverse it. We did incredibly credible and create a chasm. These are all big lessons. Cooperate to innovate is also a big lesson. Is your next one of the big lessons or one of the smaller lessons from the book? 

This is maybe a smaller one. It stuck out to me, liminal spaces. A liminal space is a transition period. As a comedian, you live there. That’s maybe even in the book. Comedians are these interlopers. You could be an interloper of culture. You can also be an interloper of eras, generations. You can see things for what they are in the present, even if they might not make sense. We are all living in a liminal space. The pandemic is this like, “2022?” Remember when people used to have party invites on Facebook and you could click two question marks? You knew it’d be fun. Nobody can tell you when this is over or how it’s over or when. It is clear that we need comedy in that liminal space. People think liminal spaces are limited, they will end. I’m engaged, that counts as a liminal space. 

That’s a perfect example of liminality.  

I’m existing between being single and being married. We live together. We have decided to be together. It’s still different. There are still things that have to be put on paper to be married. We exist in a liminal space. If we are honest with ourselves or at least this is how I see it, as a comedian, life is a liminal space. Maybe it’s a bunch of liminal space within a large liminal space. We’re all always in this transition. We’re all always in something with a question mark ending. For me, comedy is what is helping me survive. I don’t know if you guys have felt this. I haven’t seen this anywhere yet. My sense of humor has evolved by digressing and regressing so much. If you send me a joke about barf or farting, it sustains me.  

I don’t know why I’ve been holding back. 

The de-evolution of my sense of humor is directly related to the liminal space that I’m in but it’s also the seeds of where my sense of humor came from. It was where it began. Thinking about being single as a liminal space is limited thinking. You can think of having your relationship with yourself that’s forever. By forever, I mean this tiny bit of existence that we all get on this tiny rock. 

Pete is not going to want to hear this as much. What I love so much about COVID is it’s such liminal. I have friends that tell me all the time, “Shane, you love COVID. You’re going to miss it.” I’m not going to miss being cooped up. I’m going to miss the global head fuck and the constant shifting and the shaking up of the psychology and people being like, “Life is unstable.”  

It’s always unstable. We’re always on the brink.  

It’s that you’ve been in a recliner on the knife’s edge. I love that people are becoming aware of that. I love that comparison to the single life. What you’re saying is that it’s highlighting the liminal space. 

It’s highlighting it but it always existed. 

That’s what I love about pandemics, it turns out. To me, it’s like a mushroom trip. When you say that, it makes me reframe all of my breakups and everything else. Here’s the thing I always felt guilty about and the last thing I get worried about, I’ve had 2 out of the 4 relationships where the breakup finally happens. I’m the worst at breaking up by the way. Jen, you sound fantastic at it. I’m jealous of that trait. I’m the worst. 

It’s only because I fear for my life. That’s called being a woman.  

After a breakup, I’ll go in my car and go off to a gig or whatever. It’s the most exciting thing. I always feel guilty for being happy. I love the transition. 

It’s like we’re on a fresh road all of a sudden. I broke up with somebody I dated for 4 or 5 years. I remember the morning I woke up, I was shocked because I felt good. It was like, “All of these problems I’ve had for so long, I don’t have to think about it anymore.” It’s like quitting a job, which I also love to do. Shane, you’ve said the alien anthropologist thing before. That was in the book. I do comedy. My day job is to develop reality TV in its simplest form. It’s me finding who is interesting in real life who should be on television. I have a friend who describes this as the outsider artists of anthropology. I am not an anthropologist and I have no degree in such a thing. My job is to say, “What current is this and who can I pluck from it because this is a thing that exists? How do we hone in on that?” 

Pete’s death show might happen.  

Peter McGraw’s Death Flight. 

You could avoid all sorts of International Laws if you do this in a plane in the right places.  

Can you kill someone in a plane? 

This could honestly be something you pitch to Elan Musk. Why stick to Earth? Let’s take it to space. 

Pete’s bad at crime.  

I want to put a bow on this one or we’re never going to finish this show. I like the liminality idea because it does highlight. Jerry Seinfeld says, “You people, the comedians, are humanoids.” They’re not quite aliens. They’re not quite humans. They know enough but they don’t see things in the same way because they don’t exactly fit in. When you’re in one of these transitions, it allows you to recognize things in a way that you don’t. What I hear you talking about is there are these moments of transition, especially when a relationship ends, where you feel not just insight but also delight and freedom.  

The way I described this is there are two categories of singles. There’s the traditional single, the person who’s waiting out, biding their time until Mr. or Mrs. Right comes along, then their life can get started. There are what I would call solos, the people who are happy with their single life. Some of them want to remain single their entire life. They’re single at heart so to speak. Others are open to it. If I meet Mr. Right or if I meet Miss. Right, by all means, I’ll make the change that exists there. What I like about the solos is they don’t treat being single as a liminal space even if they may treat the world and our lives as liminal because they are indeed temporary and constantly transitioning in that sense. 

There’s a lot of power in calling it not a liminal space. It’s your existence. Everything’s temporary. I don’t want to bring up the death show idea again.  

This show is not feeling temporary. Let’s keep it moving. I’m going to do a brief one. One of my best compliments that I received from the book was from an early reader. My friend, Rachel, sent me a text. She was reading a draft of the book. She said, “I’ve read 200 business books in my life.” She’s a hardcore entrepreneur and an avid reader. She says, “I’ve never once read a book that talks about writing.” I dedicated an entire chapter in Shtick to Business and the title of the chapter is Write it or Regret it. In it, I talked about how comics carry around the notebook. They see that notebook is more important than a microphone in terms of their success. In it, they capture ideas. They don’t let them slip away. I’m sure you two have stories about this. They clarify ideas. They work on this. For some of them, their writing is to communicate ideas, to write a script. I constantly push people to journal for at least the first two reasons.  

There are many ideas and many things that happen in our life that slip away. If you have a regular journaling practice, it’s a useful way to capture what’s happening in your life to be able to revisit it. I started journaling as a result of writing this chapter. I’ll admit that I’m a bit of a hypocrite. It’s fun to look back at my journals and realize how anxious I am about things that don’t ever deserve any anxiety in hindsight for example. I can learn from that. Thinking and speaking are fast but writing is slow. Writing slows you down. Also, it requires precision. We don’t write likes in our writing. We focus. Writing demands precision of thought. I like to encourage anyone, my single and solo readers. It’s a place as you’re puzzling over things putting pen to paper. I do believe that a physical notepad is superior to your note section of your phone. 

Leuchtturm has a table of contents. 

Is this a planner? 

No. It’s a notebook. Every page has page numbers. In the beginning, a blank table of contents so you can put the number of your pages.  

In my journals, I do this, I save three pages so I can make a table of contents. At the end of my journal, I can go back and then write what each page was about. That way, I can open up the table of contents and be like, “I’m still worried about this dumb thing. Let’s see what I say.” 

I might have a new sponsor. 

I don’t want to oversell this. I started using this and it changed my life. It’s a beautiful notebook.  

That was my second one, write it or regret it in a particular journal. 

If you’re single, you could end up writing Eat Pray Love and then be set for life. 

There was a counter to that book called Eat Play Fuck. That didn’t make as much money. 

I’d still read it. 

Let’s do the final round more as a lightning round.  

That’s perfect because my last one builds and puts a little bow on all of the stuff that we have already discussed, which is success by 1,000 cuts. The example that I use in the book is that when I started in comedy, my writing is a little different now but my process is I write a ton of jokes. I write 100 jokes. I pick ten of them to try out on stage. One out of ten of those works and then 1 out of 10 of those that worked makes it into TV or the full-time headlining set or whatever. It’s about 1 out of 1,000. If anyone has their calculator out, I might be missing a zero or adding one there but that’s the gist of it. 

In the book, Shane calls it the 1 billion joke rule. 

I used to be good at math and now I can’t do adding zeros to things. In all of my relationships, I never wanted to get married. I never wanted to have kids. I was always honest with that from the get-go. I always loved the idea of spending my life with somebody. I’m still not opposed to it but it didn’t work over and over again. What I found out was that I love one-year-long relationships. I’m great for a year, which is a little bit too much time. It’s hard to find a female to agree to the old one-year expiration date. 

What happens? Do you start comparing holidays? It’s like, “This Christmas gift was not as good. This Groundhog’s Day is Groundhog’s Day.”  

The first year is everything’s exciting and fun.  

This is not feeling like a lightning round. 

Let’s start with New Year to piss Pete off.  

I’m sorry, readers, for packing so much incredible content more than usual into this extended special bonus episode. That’s where I learned to the bugs to features things and everything that I’ve already discussed. I learned in the hell of those multiple tours of war that I did. 

I want to make sure I understand this. The success by 1,000 cuts is it talks about the process. I like to say that Vaudeville was the first lean startup, the idea that you would go out on stage and you would try out a joke. If it bombed, you would throw it out. If it got a laugh, you would tweak it and try to make it better. In that process, you have little downside risk. If a joke doesn’t work, no big deal. You move on to the next one. A single joke could be a career-maker. In that way, it has unlimited upside but little downside. 

Success in a 1,000 cuts in the context of this conversation should be about dating a bunch and having these risk-free things. For me, it’s a success by four deep cuts that I learned a lot from. It’s somewhere in between there because it’s not marriage and it’s not like divorce and trying another. It’s something else. I do like being in a relationship but not for that long. From that, figuring out like, “What’s it like to be friends with some more females instead?” Date and travel around and not get attached to anyone and have a couple one night stands and stuff like that. A lot more trial and error than the old days like your grandparents getting together in high school and staying together for the rest of their lives.  

No offense to Jen. In many ways, marriage is exactly the opposite to writing a joke. The idea is that the potential downside of a failed marriage tends to be pretty big in that way. That’s why you should take your time and it’s why you should have an engagement and why you should do all those things. 

Marriage is like jumping into a pit of 1,000 blades. 

Four big blades.  

We’re happy to get a food processor as a sponsor.  

It’s a Magic Bullet, maybe a KitchenAid. The trial and error or even the conversation about grandparents and how they dated, especially women, they had many fewer options to be able to do that. That’s exactly when Pete told me that I was talking too much and too loud. Why not lean into the opportunity we have, especially as women, to reinvent what your personhood in your life looks like? That didn’t necessarily exist before. It didn’t exist for my grandmothers. Why not lean into it? 

There’s a lot of room for living in a different style. Jen, I had you on here because I’m not anti-marriage. I’ve met your partner. It’s great. This is about people finding the right fit for their stage in life, for what their lifestyle is like, for what their goals and wants and desires are. 

Being a comedian and where my perspective of working in the entertainment industry met and applying it to a relationship is this idea that if there’s a deal on the table and it’s not good, I’m not going to take it. If somebody is going to be my partner and I’m entering a partnership, I can say yes or no. Take it if it’s good. If it isn’t, set up your solo life and set up your single life to be as good as possible. 

Well said. That’s great. What is your last and what is proving to be somewhere between a normal round and a lightning round? 

I can do a lightning round for you. I picked out rituals. I love a ritual. I was raised Catholic. That must come from that, somehow. They love a ritual in the Catholic Church. My rituals evolve and change but they’re important in my creative process. They’re important in my processing of emotions. When I was single, what I would do every Sunday morning is I would go to a coffee shop. I would bring a book and read the paper or hangout for hours with myself. That was my Sunday morning. It’s interesting that I say that was Sunday and I do associate rituals with the church.  

You swapped one out with a more comfortable chair. 

A more comfortable chair, better coffee, and better drinks. A sip of wine, how long is that going to last?  

You’re not getting the good stuff. 

They evolve. I read the obituaries on the couch with my partner every Sunday morning. 

Do you do that? 

I find it interesting. That is one of my rituals. It has to do with the liminal space we exist in. I tend to do the same things over and over again. I love to wear the same shirt and jumper. I’ve loved working from home because I could wear the same outfit until I wear it out I would 

It’s in tatters and it falls off your body. 

I only listen to one Taylor Swift or one Jenny Lewis album constantly, on repeat. I have to have it in my AirPods because it would annoy anybody to hear the amount. I relisten to things and rewatch things. What I’m trying to say is doing that takes me to a specific place where I know I can break something down and where I know I can think about it. Rituals are a way to spur my mind frame or my mindset into something that I’m familiar with to do some kind of self-work. 

This is part of a larger lesson in the work hard or hardly work chapter. In that chapter, I tried to point out that we get mixed messages. You get a message about the value of boredom and you get the message about the value of grinding it out and working hard. The way I interpret this is some of us need a little more boredom and some of us need to work a little harder. The solution to that is to grind and then release. Do your work and then let yourself be social, enjoy yourself, go off, and so on.  

I’m also a big believer in rituals. I believe that habits are the cheat code to success in life where you remove the need for willpower, you remove the decision making. We’re good at automatically reacting to a situation. In your case, you had this ritual around Sunday mornings. If you didn’t do it, you felt off. You created a habit there. You take a habit and you add something special to it. You ritualize it and then it feels special. That’s a nice way to go about whether it be exercise, socializing, work, and so on. Have that specialness with regard to our habits. 

I love to make things special for no reason. It’s one of my gifts. A good way to figure out what rituals already work for you is to lean into the weird shit that you already do. Otherwise, it is trying to create a habit, which is hard. 

Shane, do you have any rituals? 

As you guys were talking, I was like, “I don’t have a single ritual.” I’ve read a fantastic book, The Power of HabitThey make a nice case for having that little Pavlovian reward that you give yourself. I was sitting here thinking, “I might need a ritual.” I associate it so much with church stuff. I was raised Catholic. I’m averse to anything churchy but it doesn’t need to be. I need rituals. 

Mine is a simple one. I start the day with a cappuccino. I’d either make it for myself or I go to a coffee shop and have one made to my exacting standards. It’s delicious. It’s brief. It signals that I’m about to begin creative work. It’s something to look forward to and kick it off. It feels a little weird if I don’t have it. 

I have a new ritual where I go up on the roof and I look for birds in my binoculars at sunset. I’ll probably get some phone calls from some neighbors soon. I will look up at the roof and people see me up there with my binoculars every day at sunset, looking in their windows for birds. 

I’m going to wrap it with the final one, which is also the final chapter in the book, which is called take a bigger stage. Comics are especially good at seeking out bigger stages. They’re good at seeking out bigger stages in terms of going from open mics, clubs, theaters, and arenas so to speak. Also, a bigger stage is in terms of making a move to New York or Los Angeles to cash in on their abilities. Also, comics are early adopters. They were early to Twitter. We’ve talked about Clubhouse. They’re on Clubhouse. They’re good at experimenting and seeking out platforms that can increase their reach that’s there. I apply this lesson in the book to more everyday people, not in terms of business but in terms of professional development, career development, and so on. Sometimes if you want to take your career to the next level, you might need to move to a new city or to move to a job in a different company.  

I talked about a place, an actual physical location, a platform, that may be in the case of a company, organization, or a brand. The last one is perspective, to take a bigger perspective. In the book, I talked about how I trained myself from being what we call prevention-focused, which is trying to avoid bad outcomes to being promotion-focused and that is to approach good outcomes. What I want to say to my solos is you can apply these same principles to your life in particular because solos have optionality. They have mobility because they do not necessarily have to make decisions based upon someone else’s wants, desires, needs, career, and so on.  

They can move to a new city. They can move to a new country. They can give up their apartment and become digital nomads. They can give up a career that they wouldn’t have otherwise been able to give up because they need to be a breadwinner or co-provider. They can also give up old perspectives. This belief is that there is only one acceptable path in life, which is to couple up, buy the house, the white picket fence, the family, and so on. I’m not saying that solos have to take a bigger stage. What I want to do is point out to them that they, in many ways, have more opportunities to do that because they have more flexibility, mobility, autonomy in which to do that. 

We should probably end there. This might be the last time I ever refer to Shtick to Business on this show ever again. My plan is to lean into the Solo stuff. It has been personally rewarding. I can’t tell you the number of people who reach out to me and tell me how much they appreciate this work. There’s more and more to build with regard to this project. It’s going to be my last foray into Shtick-related stuff unless something changes. 

It’s valuable work. It’s valuable for a lot of people and that you are early to adopt this social movement.  

We’ll see how it goes. Thank you both for the support, Shane, for contributing to the book, and for you, Jen, the future work, that one last project we’re going to do, which will do someday.  

It’s going to be soon. 



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About Jen O’Donnell

SOLO 73 Jen O'Donnell | ShtickJen O’Donnell works in development for unscripted television and is a stand-up comedian who runs a show in LA called The Ladies Room.




About Shane Mauss

SOLO 73 Jen O'Donnell | ShtickShane Mauss is a stand-up comedian, adventurer, and science enthusiast. He visits universities around the world and interviews researchers for his science podcast, Here We Are. A close friend of Peter’s, Shane is a frequent contributor to Solo and a special contributor to Shtick To Business.



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