The Light Watkins Show

186: Unafraid to Look Foolish, Comedian Sarah Cooper Shares Lessons From Going Viral, Divorce, Switching Careers, and Hobnobbing with Jerry Seinfeld

December 20, 2023 Light Watkins
186: Unafraid to Look Foolish, Comedian Sarah Cooper Shares Lessons From Going Viral, Divorce, Switching Careers, and Hobnobbing with Jerry Seinfeld
The Light Watkins Show
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The Light Watkins Show
186: Unafraid to Look Foolish, Comedian Sarah Cooper Shares Lessons From Going Viral, Divorce, Switching Careers, and Hobnobbing with Jerry Seinfeld
Dec 20, 2023
Light Watkins
Entertainment is one of those industries and careers where you might only get your “big break” much later in life. But could it be worth it to leave a stable, high-paying job to venture into the arts for the very first time?

Today's guest, Sarah Cooper, would answer with a resounding “Yes!” Sarah began working in tech design and at the ripe age of 32, she made a career switch that changed her life forever. Thanks to the folly of Donald Trump who inspired her videos that went viral on TikTok, Sarah became a comedian and later, an author.

In today's conversation, Sarah explains how her habit of journaling when she was young helped her as a stand-up comedian and author as well as what inspired her to write her latest book, Foolish. We discuss how she found the courage to leave a steady income for the uncertainty of entertainment, how her tech background influences the work she does today, what it's like to become a celebrity overnight, and how her spirituality fits into the picture.

We also explore how to navigate relationships after finding fame, the perils of trying to dismantle societal norms, what our guest learned from her memoir writing process, and how she views success today compared to before all the glitz and glamour. 

Send us a text message. We'd love to hear from you!

Show Notes Transcript Chapter Markers
Entertainment is one of those industries and careers where you might only get your “big break” much later in life. But could it be worth it to leave a stable, high-paying job to venture into the arts for the very first time?

Today's guest, Sarah Cooper, would answer with a resounding “Yes!” Sarah began working in tech design and at the ripe age of 32, she made a career switch that changed her life forever. Thanks to the folly of Donald Trump who inspired her videos that went viral on TikTok, Sarah became a comedian and later, an author.

In today's conversation, Sarah explains how her habit of journaling when she was young helped her as a stand-up comedian and author as well as what inspired her to write her latest book, Foolish. We discuss how she found the courage to leave a steady income for the uncertainty of entertainment, how her tech background influences the work she does today, what it's like to become a celebrity overnight, and how her spirituality fits into the picture.

We also explore how to navigate relationships after finding fame, the perils of trying to dismantle societal norms, what our guest learned from her memoir writing process, and how she views success today compared to before all the glitz and glamour. 

Send us a text message. We'd love to hear from you!

SC: When I left Google, I told my boss that I was going to be writing. I decided I was going to go write and he said – well, the first thing, he was like, ‘Do you have a book deal?’ And I was like, ‘No.’ And that was what gave me the idea to have a book deal. I was like, ‘Well, maybe I should try to get a book deal?’ But then the other thing he said was, ‘You know, you can always come back.’ And that’s kind of when I was like, ‘Wait, it’s a bigger risk to stay than it is to go?’ Because going, I can always come back. Staying and being comfortable - I just knew that I just didn’t see myself for the rest of my life designing websites and designing interfaces. I just didn’t see – I knew with writing; I could see myself doing this when I’m 80. I could see myself doing this on my deathbed, I could see myself writing in a journal as my last thing that I do. So, for me, I just had to follow that.”




[0:00:51.1] LW: Hello friend, and welcome back to the Light Watkins Show. I’m Light Watkins, and I interview ordinary folks just like you and me who have taken extraordinary leaps of faith in the direction of their path, their purpose, or what they’ve identified with as their mission in life, and in doing so, they’ve been able to positively impact and inspire the lives of many other people who’ve either heard about their story or who’ve witnessed them in action, or people who directly benefited from their work.


And today, I am back in conversation with one of my favorite humans, Sarah Cooper. So, Sarah and I originally met when she turned up to one of my meditation trainings in New York City back in the day. We’re talking years ago. At the time, Sarah was working in tech, I believe she was working at Google and then two years after we met, she published a humorous piece on Medium called, 10 Tips for Appearing Smart in Meetings, which ended up going viral and then later on, it became her first book.


And then, Sarah took a leap of faith into becoming a full-time comedian and writer, which means she left tech and a really good-paying salary, and back when Trump was running for president, she began openly voicing her opinions about him on Twitter, so much so that he blocked her. However, her comedy career wasn’t taking off as fast as she had hoped, and early 2020, she was performing standup for a crowd of two or three people at pizza parlors in New York and New Jersey and she was obviously thinking, “I’m at my 40s. So, if things don’t pick up soon, I’m going to have to go back to corporate America.”


And then, one day, Sarah was visiting with her nephews and she decided to do a Trump impersonation and post it on TikTok. It was crickets, but then the next one she did on TikTok ended up getting a million views and she continued to do more and each one went viral and Sarah became a TikTok star. She was profiled in the New York Times and other major media outlets and after Trump’s news briefings, the media could not wait for Sarah’s TikTok impersonation.


And eventually, the floodgates opened and she got a ton of opportunities such as her Netflix show, Everything’s Fine. Sarah was also featured in a film that was written and directed by Jerry Seinfeld and then most recently, she published her first memoir titled, Foolish, which includes tales from her life about assimilation, determination, and humiliation. Having known Sarah for years but not really knowing her back story, it was interesting to have her back on the podcast after reading about her upbringing and seeing how she found her purpose and all of the leaps of faith that she’s taken – multiple marriages and divorces, lots of ups and downs.


And just you know, that beautiful mess that is life and that a lot of people would feel the need to hide. Sarah is very much an open book and she’s now using her story to inspire other creators and dreamers not to be afraid of looking foolish while pursuing their inner calling, which is something that was reaffirmed by Jerry Seinfeld during that project that she participated in of his. I think you’re going to like this interview and appreciate Sarah’s story and come away with more permission to take leaps of faith in your world, which is the overall purpose of this podcast. 


So, without further ado, shall we get to my conversation with Ms. Sarah Cooper?




[0:04:50.8] LW: I was going to ask you, are you high as hell right now? Because every chapter of your book, it starts with, “I was high as hell, I was doing X, Y, and Z.” So I don't know, you do?


[0:05:02.4] SC: Yeah, I have stopped getting high because – 


[0:05:05.4] LW: Oh really?


[0:05:06.2] SC: I have. Actually, it was two weeks ago.


[0:05:10.0] LW: That’s awesome, that’s big.


[0:05:11.7] SC: Thank you. Yeah, it’s a big deal but sadly, while I was writing a book – well, actually, not while I was writing the book but a lot of the events that took place during – and it’s funny because I had such a big year in 2020 and I joked that at the pace I was going with my career that I would be in rehab by the end of the year because that’s the trajectory of like, most people in entertainment or a lot of people.


So, I didn’t end up in rehab but I did end up like really – I mean, I started taking edibles when I was 42. I mean, it was really late in life, especially for a Jamaican, and just really loved it like I really – I tapped into a different part of my mind that I had never tapped into before and I got kind of like really, it – I started to get to a point where I enjoy being high more than I enjoy being not high and then I realized, that wasn’t such a great situation. 


And also, a lot of people who read the book are like, “I can’t understand what you’re saying.” So, I’m like, maybe being high a lot wasn’t the best time to write a book but hey, like I say, if you are also high when you read it, it will be better. You’ll be able to understand it.


[0:06:30.1] LW: This is not the same thing but I started drinking coffee when I was around 40, like, in my early 40s was when I started drinking coffee.


[0:06:36.4] SC: Yeah, that’s not the same thing at all.


[0:06:38.1] LW: Yeah, it doesn’t have the same impact but it’s something that I think a lot of people don’t want to be doodling if that makes any sense.


[0:06:45.3] SC: Coffee?


[0:06:46.9] LW: Yeah, it’s like, a lot of people complain, “You know, I have too many coffees, and…” But I never really drank it because I felt like I needed it, I just drank it because I liked the taste of nut milk flavor coffee. So, it’s not even coffee that I like. I get like the almond milk or the oat milk.


[0:07:06.1] SC: Yeah, please call it that, I don’t know why that nut milk doesn’t sound good. I really don’t like you mentioned like it but say oat milk, say almond milk, that’s fine but also, I think people love coffee. People love drinking coffee, people are obsessed with coffee. Gen Z is obsessed with coffee. So, I think you’re on to something there.


[0:07:27.3] LW: But I’m in a different category because I don’t need the coffee, that’s something –


[0:07:30.9] SC: I don’t need it either, I have an espresso, I have it at 11:30 at night sometimes. It doesn’t have any effect on me, I just like that it tastes good.


[0:07:36.8] LW: Same with me, I could drink coffee any time of day and it’s totally fine but you started with gummies, right? You started with edibles?


[0:07:44.8] SC: Yeah.


[0:07:45.9] LW: What made you in your 40s start saying, “You know what? Pass me one of those gummies.” What were you experiencing at the time? You're a long-time meditator at this point, that’s how you and I first met is back in, I don't know what year that was, probably like 2013 or ‘14 or something.


[0:08:02.2] SC: Yeah, it was around then. 10 years ago at most. Yeah, as you know, I do stand-up comedy, and my goal, my holy grail of standup comedy is being yourself on stage, being as relaxed on stage as you are in everyday situations and I have struggled with this my whole life. One day, I’ll get there, I’ve gotten there like bits and pieces here and there but never like, consistent. I think that that was my initial thing with it. 


It was like, “Will this help me be that relaxed on stage?” And it does not. It’s terrible for stage, it’s terrible for performance, I get very anxious, it’s a bad situation but I did really find that I looked at things differently, I noticed things differently. You know, I like to write in the book, like I saw, sort of like these metaphors. One of my favorite stories from the book was my sister, Rachel, she’s on the spectrum, and it’s always been something that was kind of a distance between us, and we’re very close in age but we look at things completely differently.


And I don’t know, I was hanging out with my mom and my sister and we were looking out the window and there was this like, mama goose with these baby geese behind her and one of the baby geese like, still behind and my sister Rachel was very concerned about this goose that was falling behind and then, the mama goose went back to help the baby goose that have fallen behind and my mom said, “See Rachel? That mama goose would never leave her, would never leave her,” 


And because, I think it normally, if I wasn’t high, I’d be like, “Oh, that was a nice thing to say.” Because I was high, I was like, It was this huge metaphor of just, “Oh my gosh, my mom is telling my sister that it doesn’t matter, like she’s never going to be left behind.” My mom was telling me that I was never going to be left behind. It was like, this whole emotional moment that I had because I was high and so like, I had a lot of moments like that, that I sort of got addicted to. 


Like I got addicted to seeing what was behind or what was underneath what everyone was saying even if a lot of times, it wasn’t right. I just kind of got sort of indicted to that.


[0:10:20.8] LW: I think also – maybe it’s also – I mean, that’s not something you started doing when you started using those substances. I mean, it sounds like you’ve been someone who enjoys, I don't know what, is there a word for people who enjoy just observing life and just thinking about it?


[0:10:35.5] SC: Yeah. Yeah, some people call it like being stuck in your head, you know?


[0:10:42.4] LW: I’m sure there’s like a fancy Latin term for this that maybe people listening just can leave in the comments somewhere but I can identify. I felt that way before. My medium was more art than journaling but you put some of your journal entries in your book and I love the way you journal because it’s more – it’s storytelling. It’s not like stream of consciousness all over the place. 


It’s very like, let’s set the scene, let’s talk about what’s happening inside, let’s talk about what I’m seeing on the outside, so that one day when I reflect back on this, I’m going to be able to have context to what I was talking about and –


[0:11:22.1] SC: Yeah.


[0:11:23.1] LW: And the books that I read from authors who are avid journalers, they kind of follow the same pattern. They’re very detailed and it makes someone like me who doesn’t journal on a regular basis, always wonder like, “How do they remember these little details?” But you kind of trained yourself to do that over time, which is pretty spectacular.


[0:11:44.4] SC: And there’s a self-importance there as well, you know? When I look at my journals that I was writing when I was 13, I felt like I knew for some reason that this would be important. I don't know why but I was just like, “No, I need to write this down.” A lot of people are just like, “Well, what am I going to write, what am I going to say, who cares?” And I never had that. I was always like, “No, this needs to be written down, this is – needs to be recorded.” So, I noticed that with my writing was well and maybe that’s how I live my life as everything is sort of has this importance to it, every day, every moment.


[0:12:16.5] LW: Well, there’s just sort of Anne Frank nature to it as well where you’re really talking about larger society, like, you’re making observations about things outside of yourself that maybe other 13-year-olds aren’t really concerning themselves with?


[0:12:29.3] SC: Yeah, I was so deep. I auditioned for Mortified. Mortified is this show where people read their journals from when they were little and so, people get up and read their journals and I auditioned for it and I was rejected because I was too self-aware. They said my journals were too self-aware like I was too aware that there was an audience and also, the other thing I noticed too is that I noticed with my sister, which is that she talks to herself out loud and I would get annoyed with it. 


But then I realized, “Oh, I talk to myself too.” But there’s a voice inside my head. I don’t move my lips, I don’t make a sound out loud but I have a voice that I can hear very clearly and it’s my voice and it’s in my head and I realized very recently not everyone has this. Like, if you – if I tell you to say the word pineapple without moving your lips or saying anything, do you hear it in your head? Yeah, not everybody does and I think there is a difference there. Like, I have this voice, maybe part of that, I needed to get down. I needed to write it down because it was telling me stuff.


[0:13:40.5] LW: That’s interesting. I’ve never considered that other people don’t have – I’ve always had that voice as well but I just thought everybody had it.


[0:13:46.9] SC: I thought so too. I thought so too but I asked my sister Rachel, I was like, “What does it feel like at night when you go to sleep, is it just black, is it just dark and quiet?” And she said “Yes.” And I was like, “That sounds very peaceful.”


[0:14:01.8] LW: Which one of your sisters would steal your journal for like a couple of days?


[0:14:04.6] SC: Charmaine. My older sister, Charmaine who is a nurse. She stole my journal.


[0:14:11.4] LW: Why would she do that again?


[0:14:13.1] SC: Charmaine was born with Treacher-Collins syndrome. So, she looked very different, she – it’s a cranial facial difference, it’s a birth defect, and you can imagine how hard middle school and high school must have been for her, and to me, perhaps, she was sort of living vicariously through having – like, what was it like to just being a normal kid going through school.


[0:14:37.8] LW: Interesting.


[0:14:38.6] SC: I mean, at the time, I was like, “God damn it, why she can’t leave my stuff alone?” But I would steal her clothes so, I think sisters are just – you have three brothers, like, you guys must have stolen each other’s stuff, gotten through each other’s stuff.




[0:15:03.9] LW: Let’s fill the audience in because they’re probably like, “What book, what are we talking about?”


[0:15:07.8] SC: Oh, they don’t care.


[0:15:10.7] LW: We’re making reference to the book, Foolish, written by Sarah Cooper, who has been on my podcast before, she was on episode number 37 originally, and the whole schtick with my podcast is I like to tell the backstory and the motivations and understand how people became who they are, to create whatever platform they’ve created and I’m not going to do that again with you because we’ve already documented that on this podcast. 


But I do want to, for those people who haven’t listened to the first episode, just I want to do a snapshot version of your backstory leading up to today. So, if you wouldn’t mind, Sarah, just kind of taking us through whatever you consider to be the highlights of your backstory.


[0:15:56.5] SC: Well, I was born a small Black-ish child in Jamaica and my family moved here in 1980. When I was three, moved to Rockland, Maryland. The youngest of four, older brother, George, Charmaine, and Rachel, and always loved performing. I felt it was my duty and my family to make everybody laugh and to make everybody feel good and so that was sort of my role in my family and it was my role in school. 


I was kind of a clown and really wanted to do some kind of performance, wanted to sing, and then turns out, I couldn’t sing and I wanted to act and my parents were very pragmatic and they’re like, “You got to do business.” So, I got an economics degree, I hated that. So then, I went into design, digital design at Georgia Tech, and then I was working in an ad agency that I worked in tech for a while. 


I found standup comedy around age 32 and stared writing my own material and really merged comedy in the corporate world with an article called 10 Tricks to Appear Smart in Meetings. That went viral and that’s what I consider sort of the start of my career in terms of comedy. And wrote A Hundred Tricks to Appear Smart in Meetings, which is – I don't know when this is coming out but people love that as a white elephant gift at work.


And then I wrote, How to Be Successful Without Hurting Men’s Feelings, and then I was about to go back to tech when in 2020, I was inspired to start lip-syncing the president and that kind of changed my life and I really, really, really like, was able to do a Netflix special. I was able to turn my books into pilots and as any good story, like, all of these amazing things are happening for me and then, at the same time, I was going through a divorce from my husband, who I had met at Google when I was working there.


So, the past three years from like 2020 to 2023 have just been really a huge adjustment of, “Okay, now, I’m – you know, I have an agent now, I have this career that I’m trying to build.” You know, I love storytelling, I’ve always wanted to write a TV show, write a movie, I still want to do all of those things and in 2023, I got this book deal to write a memoir and so, I wrote this memoir called Foolish: Tales of Assimilation, Determination and Humiliation. And yeah, I will be rewriting it because I wrote it high.


[0:18:31.3] LW: Well, okay, so that’s interesting. You’re not serious about that? You’re not going to rewrite it?


[0:18:36.8] SC: I am. It’s going to be a trilogy, it’s going to be Foolish, Foolisher, and then Foolishest. I truly believe in the structure of the book. I truly believe in the structure, I believe in what I was trying to say but I think a lot of it is my standup comedy, and a lot of it, I don't know if it really translated to the pages well. I’m really not doing a good job of selling my book. It’s a great book, it’s the best book ever, go buy it. That’s what I should say. 


[0:19:02.1] LW: What was the intention behind “Assimilation, humiliation, determination?” 


[0:19:06.6] SC: The basis was really like family, the first one is “Assimilation.” So, when we moved here, my parents very interested in success and as Jamaicans coming here, we moved up, every time we moved, different house, bigger house, wider neighborhood, it’s all about the sort of proximity to whiteness, and this proximity to success and what is successful and looking at success as what has worked before.


So, the idea that I would be like, “I want to be an actress” was insane to them, it was like, “What? No-no-no.” And so to please them, I sort of did this, I worked in tech. I did the thing that like, “Oh, everybody wants to do that, you’re making money.” You got a six-figure salary, all of that, get married, try to have kids, buy a house, that was the assimilation. So, I was doing all of those things based on what my parents and what capitalism tells you to do. 


So, that was the best part and I think that was sort of like the baby part of me, the subconscious part of me, like just following sort of rules, and then determination is about who am I really? It’s really ridiculous but I did spend a while talking about my favorite colors, and although that chapter is pretty boring, I will say that these questions, I didn’t ask myself. I didn’t ask myself, “What do I like? Who am I? What music do I like?” 


But my ex-husband, he chose all our art, he chose everything. Like, I was just put together based on everything that was popular in society. I wasn’t me. I didn’t take the time to figure out me and who I really was and what I really liked. I was just thinking about this room in my apartment, which I love and it took me years to figure out what to do with this room and I was like, “Put a desk in it and make it an office” because I love work and I love what I do, and I want to be doing it as much as possible.


So like, it took me years to just figure that out and so, asking myself those questions, determining who I really am, that’s that second part. And then the last part, humiliation is about taking these chances that I took in my life, trying to sing, trying to act, trying to do standup comedy and how humiliating and terrifying and how foolish you feel when you really put yourself out there as many times and as many different crazy ways that I have.


[0:21:28.9] LW: And it’s very transparent, vignettes from different aspects of your life that I think a lot of people can relate to. At least, I could relate to a lot of the stories in your book. I’m curious though, when you were writing, who was the audience that you had in mind?


[0:21:44.8] SC: Everybody, obviously, I thought the world is going to be like, “Oh my God, this is a revelation.” But mainly, women. Mainly women who have sort of put aside their own desires and thoughts and feelings to live this fantasy that’s not even their own fantasy. It’s a societal dream that they’ve bought into. My hope and my dream was to sort of say, “Hey, this is how I stop being a robot and you can stop being a robot too,” That’s kind of what I was going for.


And that, the first part, assimilation is like sort of a rejection of being a white and the second part is a lot of sex and I – not a lot of sex but I do discuss sex, I’m not great at discussing sex but thinking about sex not as like, “Oh, you were made to have babies.” But like, no, actually, sex can be something that you just enjoy. It’s not just for the man, it can be something for you as well. 


And then, that third part of just like, no, you don’t actually have to work in tech or have a – go be a lawyer, you can create your own career and do what you love. I was hoping that people who feel sort of stuck or people who feel like they are just following a script could see how I sort of broken that script or created my own different script.


[0:23:00.1] LW: Was it therapeutic for you? Because some of the things you put in the book are so transparent. I know for myself when I’m doing my writing and I think to myself, I don't know if I want my parents reading – 


[0:23:13.0] SC: Yeah.


[0:23:13.4] LW: How did you sort of navigate all of that as an author? Because you described your first time having sex and you slept with multiple people in your office and all these kinds of things.


[0:23:22.7] SC: I only slept with like two people in my office. I love the question, “Was it therapeutic for you?” Because I get so defensive. When people ask that, it’s like, “Did you at least get something out of this? Because nobody else did.” No, it was therapeutic, and actually, when you ask me “Who did you write this for at first?” My first thought was, “I wrote it for myself.” And so, yeah, it was therapeutic and there were a lot of things where it’s like, “I love this story,” There’s so many stories that I just love so much and I was just excited to tell them.


[0:23:58.7] LW: I think that’s perfect. I think that’s why we should write, and the more specific we are, usually the more universal our storytelling becomes, and the more kind of guarded we are and again, this is from my own experience, trying to make everything fit, trying not to offend anyone, trying to please my parent and anyone else who read it, it just comes off as flat, there’s no impact with it. And it’s not that you have to try to be impactful, just be honest, just tell your truth, and then other people are like, “Oh my God, yes. I experience that too.” You know?


[0:24:31.1] SC: Yeah.


[0:24:31.7] LW: I try to make a relationship work with someone and all they want to do is hook up with me and we’ve all had that experience.


[0:24:37.0] SC: Haven’t we?


[0:24:39.3] LW: We’ve all been there.


[0:24:40.7] SC: Relatable AF.


[0:24:42.1] LW: Yeah, but some of the themes that really I thought, were very inspiring was just all the stories about how you bet on yourself and I put in that category, you leaving your relationships, which is a very difficult thing to do. In spite of the fact that you guys are arguing all the time and you know, there’s all these obvious issues.


So, talk about you, having sort of a dream job at these major tech companies, Yahoo, and Google, and then deciding, “Yeah, this is great but there are other things that I want to do.” And then, having to go back. A year later, you’re broke and having to go back and get another job and then quitting that one and just, I guess, talk a little bit about that process, and now, who I’d like for you to talk to are the people out there who are like you. 


Young women perhaps, even young men who, on paper, they looked successful, they look great, their whole family’s probably bragging about them at church but they don’t feel like this is where they’re supposed to be and they’re journaling and they’re writing jokes or telling stories or doing something.


What was it that gave you the courage to say, “You know what? I’m going to do this, I’m going to do it.” Because we all have that conversation that want to do it but very few of us say, “I’m going to do it” and then actually do it.


[0:25:59.0] SC: Yeah, I mean, I have to give it up to my family as much as they put a lot of pressure on me to not make mistakes and do the right thing. I will say that they’ve always said, “Anytime you need, you can come home.” And they’ve always said that. “You always have a room here, you always have a home here.” And so having that, honestly, I think helped me take a lot of risk.


As much as they were like, “You’re going to leave Google?” You know? Or like, “You're going to leave Yahoo?” As much as they were like that, they were also like, pretty open to giving me that net to fall into, if I was to fall.


[0:26:31.6] LW: And you had to take them up on it a couple of times in your 40s.


[0:26:34.0] SC: I realized, and I didn’t put this in the book but I realized I had taken him up on it three times in my life and it was always after a breakup. I always had to move back in with my parents after breaking up with the guy at 21 and 30 and at 42. So, I’ve done it in every decade, knock on wood, I never have to take them up on it again but I might, who knows? And when I left Google, I told my boss that I was going to be writing. 


I decided I was going to go write and well, the first thing, he was like, “Do you have a book deal?” And I was like, “No.” And that was what gave me the idea to have a book deal. I was like, “Well, maybe I should try to get a book deal?” But then, the other thing he said was, “You know, you can always come back.” And that’s kind of when I was like, “Wait, it’s a bigger risk to stay than it is to go?” Because like going, I can always come back. Staying and being comfortable – I just knew that I just didn’t see myself for the rest of my life designing websites and designing interfaces. 


I just didn’t see but I knew with writing, I could see myself doing this when I’m 80. I could see myself doing this on my deathbed, I could see myself writing in a journal as my last thing that I do. So, for me, I just had to follow that and when you, out there, listening, think about what is the thing that you could see yourself doing until you’re 80, what is that thing? And sometimes, it’s a bigger risk to get addicted to that comfort than it is to just take a chance.


[0:28:01.2] LW: You mentioned designing interfaces and you took a bet on yourself to become a comedian and I’m a big believer that all of the experiences that we have in life, no matter how random will end up coming into play at some point and we do start to find our purpose.


[0:28:15.2] SC: Yes.


[0:28:16.0] LW: And as a self-aware person, I’m curious to know, what elements of interface design translated into comedy?


[0:28:24.6] SC: Empathy. Mainly empathy and thinking about who is looking at this, who is viewing it, who is using it and what do they want. What do they want to hear, what do they want to see, what’s the next thing that they think? I love comedy where it feels like they know exactly what I’m thinking. They say something, they know what my response is going to be, they respond to that response before I’ve even said it, and so that sort of empathy definitely plays into comedy, to writing. 


You’ve written two books, you know that. You're really good at like thinking about what people – I remember when you used to do the daily, you did a daily sort of inspirational quote, right?


[0:29:02.1] LW: The daily dose of inspiration. Yeah, I’m still doing it.


[0:29:03.8] SC: Do you? Oh, you’re still doing it, okay. Oh my God, you’re still doing it. Oh my God, that was incredible. For me, like every morning, waking up to that I think that – I felt like sometimes you were inside my head. It was such a good feeling to know that I wasn’t alone and also, I hate the internet sometimes, and then things like that make me love the internet because it’s one step ahead of me, sometimes in a good way. 


So, I think empathy definitely played into that but in a lot of ways, it was bad because there’s such a dependence on data and doing what works. I see some comedians who have worked in tech before, creating spreadsheets, and their jokes and like, writing down the numbers of laughs and the – you know, thinking about things in a very like, methodical way and I hate that shit so much. 


I hate it so much. There’s so much more benefit to feeling, to be on stage and feeling than there is to thinking, “Okay, this worked before, let me say it like this, let me pause for the same amount of seconds” like, “Oh, gross.” So, that stuff, I kind of had to throw away that perfectionism, that methodical tracking of things, I had to throw that stuff away.




[0:30:33.3] LW: When you were anonymous Sarah Cooper, going to the pizza store to do open mic night.


[0:30:40.2] SC: The pizza store?


[0:30:42.5] LW: Yeah, pizza restaurant, those kinds of gigs. What were some of the highlights that stand out to you now as someone who has had exposure to Hollywood and all of that? Like, what can you reflect back on now and go, “You know what? Those were – that was a really cool moment when that happened.”


[0:30:58.3] SC: Well, I just remember performing for two people at a comedy club at like midnight in Astoria and you know, two more people.


[0:31:08.8] LW: Were you paying to be there?


[0:31:09.7] SC: I mean, if you looked at the fact that I wasn’t being paid and it costs so much money to get there, yeah, definitely, I was paying to be there. And two other people would show up and I’d be like, “Oh, my audience just doubled” you know? And then, I was talking to four people and it was great, and then in 2020, when I did – all I wanted was a late-night set. 


That’s all I wanted in life was to get on late night and in 2020, I finally got to, a guest host Jimmy Kimmel but it was during a pandemic, and so there was no audience, it was for two people. Who is doing it for two people in a room? So, the fact that that experience of performing for two people when I had no success was the you know, very much prepared me for performing for two people when I was at sort of at the height of my success in that year.


That was pretty cool but it’s like those moments of humility, like Mark Normand is one of my favorite comedians and he had just done The Tonight Show, and then a week later, I was watching him perform in a bar, in a basement, while a group of women were having a birthday party and barely paying attention to him, and a week earlier, he was on The Tonight Show. 


And so, it’s just this weird, you could be up here one second, literally one day, and then the next day, you are back down, and then you could be up again, and it’s just like, it’s kind of a mirror of life and it’s a really – it’s a test of yourself to be able to stay as even and as dedicated as you can no matter what response you're getting.


[0:32:35.4] LW: You first took the leap I believe in what, 2013 or something like that?


[0:32:39.4] SC: ‘14, yeah.


[0:32:40.7] LW: 2014 and six years later, you have this randomly viral big talk video but in between 2014 and 2020, if you have to say how many times you thought about quitting and going back to sort of a conventional life, what would you say? 


[0:32:59.3] SC: You know, I got married in 2015. We tried to have kids, if that had worked out I would have been a mom. I would have, I think I would have probably given up at that point. I was just like kind of trucking along and my ex-husband was really great about being the breadwinner and making the money and that was really helpful. So, I thought about it a lot during that first year and a little bit less during the second year and then you get to a point where you’re like you’re freelancing. 


So, I’m kind of – I still have my toe in a little bit so that I can stay sharp and maybe go back at any time. So, I feel like I thought about it so much during that first like 18 months and then a little bit less. And then around 2019, when it really felt like nothing was working and I really questioned whether or not – mostly I was missing a community because when you are working for yourself, by yourself, and you’re a writer, it’s such a lonely experience, actually. That’s the thing that I really missed about Google. 


It wasn’t the work, it was the people, it was the place to go, it was that sort of support system of people to talk to and relate to. And in 2019, when I was thinking about going back, it wasn’t so much that I needed the money. It was more like I’m 41, 42, you know, who do I talk to? Where are my friends? Who am I relating to on a daily basis? And so when I when I was thinking about going back then it was really about that. 


Where is my 401(k), you know? Like, who’s going to be there when I’m 60 and – what does retirement look like? When you’re 40, you start thinking about those things. Your parents start getting older so that’s really what it was about is that. 


[0:34:35.6] LW: You know Matt Rife, right? The comedian, Matt Rife. 


[0:34:37.7] SC: Yeah. 


[0:34:38.1] LW: His story, he said before I think a couple of years ago, he was making like USD 30,000 as a comedian and just not really getting traction at all, and then he goes to this comedy festival but he pays to attend, they weren’t going to let him perform, and it’s just all these things and he just posted this video of some crowd work that he had done you know, several weeks before because that’s just what he would do. 


Like on occasion, he would post videos to TikTok and then it goes viral, and then before you know it, he’s like one of the biggest comedians in the world. 


[0:35:13.1] SC: Yeah, I mean he’s – 


[0:35:14.3] LW: I mean, he’s taken like 25 million a year or something like that. 


[0:35:16.6] SC: He’s so big. Well, my sister, Charmaine, she’s not into comedy and offline, she, the other day was like, “Have you heard of Matt Rife?” and I’m like, “Okay if he’s reached Charmaine, he’s huge.” 


[0:35:25.8] LW: But you had that moment, you had that moment. So, tell us a little bit about what that’s like because you’re learning how to do TikTok, your nephew is trying to show you and all this and – 


[0:35:35.8] SC: Yeah. 


[0:35:36.4] LW: And at the same time, this Trump thing is happening with the pandemic and you post, and what happens from the perspective of just a regular person relatively anonymous to you having your own Netflix show months later. What was that like? 


[0:35:52.1] SC: It was such a whirlwind – the first video going viral and getting a million, I’ve gone viral before and I just – I thought it was the same thing. I was like, “Oh, this is Ten Tricks who appears in our meetings, it will go viral, maybe I’ll get something out of it but it’s not going to change my life.” And then, when I kept making the videos and they kept going viral and my ex-husband, Jeff, would help me track how many view each things we’re getting, he set up this whole system to see who was retweeting me and it was very exciting. 


Every time I made a video, it was just this moment of just like, “Ooh, this is exciting, I am sharing this and see how well it does, see what people say.” And I love seeing how people were responding to it and then certain things started to happen. I was walking around the neighborhood and somebody drove by and yelled out, “Look, it’s Trump” and I was like, “Oh, that’s weird” and then a few weeks later, I got recognized by this little girl while walking my dog and that’s when I was like, “Oh, I’m being recognized on the street by strangers.” 


So, that was a little bit different. I’ve been trying to get an agent and finally, I had meetings with every agent. It felt they all wanted to talk to talk to me. I’ve been wanting to audition, finally, I had all these auditions. It just built up and built up until I’m talking to Natasha Lyonne in my root off and I’m like, “Let’s do a Netflix special” and they’re like – and I’m like, “Okay.” I think I was sort of just looking back and especially now knowing how hard the business is, I don’t know why but everything was just popping. 


It was just popping, things were just happening. So, it was like things were just like handed to me. It was wild, I became a white dude, I became Trump basically because – you know what I mean? I all of a sudden became more just like, “Here, have everything” and I was like, “Oh, this is amazing.” But I think I did take it for granted a bit because I’m just like, “I don’t know how things work.” So, I just thought, “Oh, this is how things work. You just go viral, everything is great.” 


[0:37:55.8] LW: How were you looking at it spiritually? Were you thinking, “Oh, I’ve manifested this and I thought about it, and visions boards and the law of attraction.” Was any of that coming into your internal dialogue of, “This is meant to be” or did you just think it was just luck? 


[0:38:12.5] SC: The only thing because – and I write about it in the book is that I’ve been lip-syncing since I was little because I wanted to sing. So I was singing in church and my mom was like, “Mouth the words.” She told me to mouth the words because I had such an awful voice, I guess. So, lip-synching was something that I did because I couldn’t sing and then sort of the making fun of the businessman, the businessman who’s full of shit. 


Like a hundred tricks that appear in our meetings, that’s all that is. And so looking back, the nodding, yes, and Steve Jobs talks about this, how you connect the dots looking back and I kind of did that, you know? I was just like, “Oh, why have I not been making fun of him this whole time?” And actually, I was just pissed because A Hundred Tricks came out two weeks before he was elected. I’m not saying that A Hundred Tricks would have been like huge had he not been elected, but almost. My press got ruined because of him. So, I did feel a little bit calm getting him back for that a little bit, but I wasn’t feeling very spiritual. 


I was feeling kind of – try to – Jeff and I were having even more problems at that point, so I was sort of managing that and also trying to like, “Oh yeah, no big deal.” I’m like talking to Jon Hamm, no big deal. I was trying to just be cool. I was trying to be as cool as possible. And so I would say that maybe I was as disconnected from myself as I ever been, because all of these huge things were happening to me and I was just trying to be cool about it when really, I think about it now and it’s like, “Wow, I can’t believe that all of that happened.” 


[0:39:43.7] LW: Yeah, I love that part of the book and I think this could also be very helpful for people. You talk about how you were basically Jeff’s wingman during your relationship together and then you started getting all this attention, and then he started questioning “have you changed?” but you were just trying to navigate all of this, and being in the spotlight, and then having to kind of rise up to meet that demand. 


So, what sort of reflections do you have now that could help someone else, another woman who is in that position who is being the good wife and a good, whatever, homemaker and with her hobbies, but then those hobbies start to get traction in a big way and so now, she’s got to really step up and feel supporting the way that she felt supported. What was that like navigating all of that? 


[0:40:36.9] SC: It was tough. It was tough being like, “Yeah, no big deal” like to him, I had to sort of minimize. I had to minimize and I would love to talk to more of the men and be like, “Hey, be supportive.” Whether it’s a man or a woman or whatever. But a lot of times your dream starts to come true and your partner or your friends they don’t like the new you maybe, or they want you to not change and I get that, and I feel that too.


I mean, I feel that so much that’s like a deep feeling of, “I don’t want to leave anybody behind. I don’t want to change, I don’t want to move on like I love my friends, I love my family.” You are not leaving them but you are changing, and change I think is really good. Change is a sign that you’re human. So I feel like in any relationship, for me being able to be excited for that change and not be threatened by it and be with someone who is going to be excited for you. 


I think as much as I love Jeff and as much as I loved a lot of my friends at the time, there were people that it was hard for them to be excited for me, and whether they knew it or not, it was hard for me to be as excited as I wanted to be in a lot of ways. And so there’s fair weather friends who are only there when things are good, but there is also friends who only like you when you need help or things aren’t going great. 


And so, you need a friend who’s going to be there when things are great and when things are not so great. Both of those times are important times to have people in your corner. 


[0:42:12.2] LW: How did your friendships evolve during that period for you, that 2020-2021 period where you were getting all that attention? Did your friendship circle get smaller? Did you have those people coming into your life who really had and really been there before? 


[0:42:26.8] SC: I started to make friends with like more artists and it’s such a different world, the corporate world versus entertainment. The people you meet and also like how you show up. I feel like in the corporate world, I could fake a lot of things and in entertainment, you just – you can’t. You got to be genuine, you got to be a real person and – 


[0:42:50.2] LW: What do you mean by that? You could fake versus being real. 


[0:42:52.4] SC: So, you could go to a meeting and nod or you can go to a meeting and pretend like you’re paying attention. You could say, “Sorry, I forgot your name. Who cares?” It’s just so easy to phone it in, in the corporate world, and I was phoning it in, in so many of my relationships. And when I started to meet more people who weren’t phoning it in, who were living their truth and their lives the way that they wanted to and they were dedicated to what they were doing and they had their purpose figured out, it was a shock to my system. 


I’m just like, “Oh, I don’t actually have that figured out about myself.” And in the process of figuring it out, there were people – I actually had a friend group that I found that was very, very supportive of me through my divorce, through all of that. And then I started to meet more people who were kind of living their lives in alignment and living like true authentic lives, and kind of gravitate towards them because that’s where I want to be. 


That’s kind of what I want to live. So it’s not like you’re leaving people behind but you need different people to feed different parts of you. I had to kind of realize that and also I’m just like really – I feel weird talking about it because I feel bad about it. I do, there are friends that I think I probably didn’t show up for as much as I should have and because I was so obsessed with a lot of the things that were going on with me. 


And also I think there’s a full movement online right now to be like, “Oh, boundaries” and oh, if people trigger or if people don’t do what you like, just like cut them out of your life. And there’s a lot of movement towards, “Oh, embracing your introversion” and all that stuff, and I’m not about that anymore at all. If you trigger me, that’s my thing and I want to figure out why you triggered me. You’re going to help me because you’ve triggered me, like that’s going to help me figure out something about myself, and thank you. 


Thank you for triggering me. I don’t believe anymore in cutting people out and leaving people behind and any of that. It’s just that people are there for different seasons and different reasons and see? I’m a poet now, but yeah. I’ve had so much learning to do when it comes to relationships, I really have. 


[0:45:00.5] LW: I’ve got a theory about this and I’ve talked about this before on different episodes of this podcast, but my theory is that there is no such thing as a toxic person or a toxic dynamic, provided that you honor each dynamic’s expiration time. So, kind of like milk, like you don’t drink milk after the expiration date. 


[0:45:22.7] SC: Yeah. 


[0:45:23.4] LW: Your dynamic with a friend or a relative might be great for an hour or two but then if you try to spend three hours with them, it starts getting toxic, and they start triggering you, and you start triggering them. And the mistake we make is thinking, “Oh, that person is a toxic person” but really, all that means is you’ve exceeded the expiration time. So, everybody is great for a certain amount of time. 


Like for instance, my mom, she’s great for a few hours. But if I spend more than that around her, she’s going to start giving me unsolicited advice. She’s going to start telling me how to drive, she’s going to start saying things, trying to tell me the correct way to wash the dishes, and it just gets under my skin. And I start to get into the story of, “Oh, she’s this or that kind of person. She’s controlling” da-da-da. 


No, I’ve just spent too much time with her. I just have to be aware of that and then when I feel that that expiration time has been reached, take a little break. Take a little space, let me step out, you know? Or just not plan to spend as much time around those particular people. Some people you can spend all day with and it’s great. Some people, you can spend only 30 minutes around and it’s great and then if you exceed that, then it’s going to be a problem. 


[0:46:36.2] SC: I disagree. 


[0:46:37.3] LW: You disagree? 


[0:46:39.1] SC: Yeah. 


[0:46:39.8] LW: Oh, tell me. Tell me more. We’ve exceeded our time together, so. 


[0:46:44.7] SC: Yes, you know what? Time’s up. 


[0:46:46.5] LW: We have the time pass. 


[0:46:46.5] SC: But like – 


[0:46:50.5] LW: No, tell me. Challenge me on it because I need to – 


[0:46:52.8] SC: Yeah. What is your mom triggering any to you? What is she doing to you? What does it feel like? Why is she doing that? What is it saying? It’s an opportunity to learn, you know? There are certain things about my mom, like you asked before about like, “Are your parents going to read the book?” No, they’re not. My mom isn’t going to read the book. She’d stand it, that’s fine. 


But that was a huge – I think I’m just like, “Oh, she doesn’t really want to know everything.” I always thought my mom was my best friend. I realized now, no, she’s my mom. She wants me to be happy. If I had a bad set, I tell her I had a great set because that’s what she wants, that’s as much as she can sort of take, you know what I mean? But I talked to my dad yesterday, I’ve lived here in this apartment almost three years. 


But since my divorce, he hasn’t been visited. He hasn’t come to visit and so I again, I’m like, “Dad, I want you to come next year” and he’s like, “Oh, I don’t know” and I felt it in my heart. I was like, “Ouch, he’s really not going to come visit me and he’s really not going to come” but I just had to be like, “What is that, why is that rejection hurt so much?” Like, what is it saying about me? 


Because I feel that too when I get on stage and I don’t get a laugh, so I can make that connection and I can learn about it and figure out how to get through it instead of avoiding it, because avoiding it is actually not helping me. 


[0:48:09.6] LW: Yeah, I think what we all want ultimately is to be ourselves, right? 


[0:48:14.5] SC: We do. 


[0:48:15.3] LW: And they want to be themselves, we want to be ourselves, nobody wants to be psychoanalyzed. No one wants to be told that they’re not doing what they should be doing, etcetera, etcetera. And I guess the way I cope with that because I kind of – I have similar stories that I could point out in my relatives but none of my family has read any of my books. 


[0:48:36.8] SC: Oh my God, solidarity. 


[0:48:38.8] LW: But I realized that’s just that, that’s just how it is. At least for me, that’s how it was then, so I can allow myself to get – 


[0:48:38.8] SC: But it doesn’t trigger you? Does it trigger you?


[0:48:50.1] LW: No, it doesn’t trigger me. It doesn’t trigger me, it’s just – 


[0:48:52.8] SC: But I feel like that’s healthy, that’s healthy when something doesn’t trigger you. 


[0:48:56.1] LW: It helps me to adjust my expectations. 


[0:48:58.4] SC: Right. 


[0:48:58.9] LW: Around it, so that when I am around them, I can extend the expiration time a little bit more because I’m not expecting them to show up in a way that I show up, right? 


[0:49:08.5] SC: Exactly. 


[0:49:09.4] LW: And honestly – and actually my mom taught me this because she used to volunteer to help out this woman who just nobody really wants to be around because she was so annoying. But my mom said something really profound one day. She said, “I’d rather be the person who’s choosing to be around the annoying person than be the annoying person that nobody wants to be around.” 


[0:49:30.8] SC: Yeah, of course, and I think about that with my ex-husband sometimes, like he was a very confrontational person. He liked the confrontation and I hated the confrontation, and so he would create a confrontation and my immediate response was, “I’m sorry, my fault. I’m sorry, it’s okay. I’m sorry, I’m sorry.” 


[0:49:45.9] LW: Were you being facetious or were you genuinely saying, “I’m sorry, it’s my fault?” 


[0:49:50.5] SC: Okay, so I wasn’t being facetious but I was trying to cut off communication. I didn’t realize that just apologizing immediately actually does create a wall. I was creating a wall and trying to just move. I thought I was doing a good thing by trying to move past the confrontation but what I was doing was trying to ignore the confrontation, get rid of it as quickly as possible, and so that was my thing. 


Like sometimes, I’ll just apologize to get out of something. Sometimes I’ll just start asking you questions that you don’t have to ask me a question and I have to notice these things about myself when I am trying to not engage, and not really connect, and not really feel where you are, and not really maybe avoid a feeling in myself, I‘ll do these things that I think are really good but they are actually creating a wall.  


[0:50:33.5] LW: Let me just – reflecting back on your story, I’ll look back and I’ll say, “Well, you know, yes, they’re not coming by your place, yes, they’re not reading your book but they did let you stay at their house. 


[0:50:44.7] SC: Exactly, yeah. 


[0:50:45.8] LW: And you know that you, probably, if you really put your attention on it, you could think of a million things that they have done that has been what they felt they could do to show up, and that’s the beauty of humans because we’re all diverse in that way. We all do what we feel we can do to show up. 


[0:51:03.4] SC: I know, and that was another huge realization because a lot of times you blame someone or you crucify someone for something they actually don’t have control over. They’re just doing the best that they can with what they have. I realize in my marriage, I didn’t look under the hood with Jeff, I really didn’t. There are a lot of red flags and red flags are a funny joke but they’re also real like that I ignored because I just wanted to get married. 


I just want – I was 35, it was too late. I had to do it, I had to do the thing, and so that was my bad. It was my bad, I said, “I love you. I’ll be with you forever” but the thing is did I really know myself? Did I really take the time to figure out what I actually wanted and who I was? No, but I was doing the best I could with what I had at the time and what I thought I needed. 




[0:52:01.1] LW: That’s what I love about writing books, having to organize your thoughts and put it all out there and to see, “Okay, where does this fit? How does this connect to what I experienced earlier?” Because like I said, you and I had that conversation back on episode 37, but then reading your book, I heard stories that I did a fair amount of research the first time, but there were things you really didn’t talk about that I thought, “How did this not come up on our first conversation together?” 


[0:52:27.6] SC: Oh, really? Like what? 


[0:52:28.7] LW: I mean, there’s so many things, so many like little things because I like the little things, I like the mortar in between the bricks moment. But just little things, like you consider yourself to be a consensus builder back when you were at Google and how that could have informed your path, or I didn’t know you worked at Yahoo and then you quit that and then got to Google and then you quit that. Like I thought you only had one job that you quit and – 


[0:52:52.8] SC: Yeah. 


[0:52:54.3] LW: But that’s what we do when we tell our stories having not written them down, we form composites, because it’s just easier. I don’t have to get into all these little details but when you write it down, you’re actually encouraged to get into the details at least to kind of find the through line and the narrative. So, what was that process of writing all of your memoir, what did you discover about yourself or your story or your journey through that? I’m imagining it was like a six-month-plus-long process. 


[0:53:25.2] SC: Oh yeah, it was over a year and a lot of the things I had written before are like some of the things I’ve written when I was 30. Yes, so many connections that I made that I never made before, like the Ficus that I threw in the dumpster in San Francisco and it took me several times reading that to realize how close Ficus and fetus are. I mean, those are two very close words and it’s just so funny that someone discovered it and someone gave me a hard time about doing it. 


But it was a plant and don’t ever throw a plant in the dumpster in San Francisco because you will be crucified for that. And I have to say, the biggest thing that I – when I read it was like, “Wow, I was obsessed with powerful men.” I wrote about men a lot, I wrote about powerful men a lot and my obsession with powerful men and that was the big thing. It was like, “Oh my God, I never thought I had daddy issues but I do.” 


I was obsessed with my dad and making him laugh, I was obsessed with Trump and I was trying to figure out how to get at him. I was obsessed with finding a man who could make me feel like I was powerful, just obsessed with so many men and then getting to the end and being like, “Oh, I need to find that power inside of myself.” 


I’ve always been looking externally how many views, how many likes, how many shares, all of this stuff to tell me how great I am or how much power I have or how much success I have, when actually, that shouldn’t be the thing that makes you think you’re powerful or makes you think you can do whatever you want to do. So, that was a big realization for me and I felt kind of ashamed of it. I was just like, “Why am I talking about men so much?” But in our society and for women, as a child, I would practice writing my name with somebody else’s name. 


My name wasn’t good enough and little girls everywhere are conditioned to believe that the thing you need to do is get married and get a husband. We all think we’ve gotten so far ahead of that story but we really haven’t. Most women still believe that that’s the thing that you need to do and need to get. I will say that I’m not looking for a relationship now and I feel very empowered about being someone who isn’t really searching for that anymore. 


But it’s only because I did it. It’s only because I actually did it and so now, I can move past it. If I had never been married, I’d still be looking to get married probably. 


[0:55:45.9] LW: What is the illusion that you think a lot of say, women, women have who are not married, who are fantasizing about that? Like in your experience, having been married twice. 


[0:55:56.7] SC: Thank you for reminding everybody. 


[0:56:00.8] LW: And now enjoying living on your own, you say multiple times through, in the book. 


[0:56:04.8] SC: Yeah, I really do. Well, for me, and for I think what I see is it’s just competition. I see a lot of competition between women of just like the Instagram picture, checking the box, get married, have a baby, get a house - it’s just so many women are just like, “Let me do it all and let me do it all and get married, buy the house, try to have a baby, try to have another baby.” It’s just this thing that they feel like they need to check those boxes. 


And I feel like some women really want that and some men really, really want that but some of us don’t and it’s so hard to tell the difference. It really is because society supports one of those things really well and it doesn’t support the other thing very well. So you go for the thing that everybody is telling you to do and telling you that’s going to make you happy and it’s going to – you’re going to get to have a party. 


You’re going to have to have all your friends know that you’re married now. I also felt when I was married like, “Oh, that’s settled. I don’t have to worry about that anymore. I can focus on this now.” It was a checkbox, it literally was the checks, and I think for a lot of people that’s what it is. 


[0:57:09.2] LW: Looking at that framework talk about your new-found connections and success in Hollywood and all of that, what is that like on the other side of those sort of virility that you experienced now that we’re in 2023, and your best friends with Jerry Seinfeld and all of that?


[0:57:25.4] SC: Yes, right. 


[0:57:26.1] LW: Well – 


[0:57:26.1] SC: I don’t know, no, not an author. Success came to me, I just remember this one saying I was on set with Jerry Seinfeld. It was like my last day, he looks at me, he’s just like, “You kind of became a success overnight” and I was just like, “Yeah” and he’s just like, “Not an easy thing to do or not an easy thing to be” or something like that. He just was like – or he said, “It’s not a walk in the park, you know?” or something like that. 


And I just kind of laughed at it and I didn’t really think about it but then now, I don’t want to be a person that is successful through shortcuts. So, I’ve gotten to a place now where I look at it like, “Wow, that was really great that that happened but if I really want long-term success, it’s going to be work, it’s going to take years and I got to be in it for the long haul.” I think when you do get viral success like that, you can start to get seduced into thinking it’s that easy and nothing is that easy. 


And so, right now for me, it’s about, “How do I build relationships with someone who I respected and admire as much as Jerry Seinfeld?” So that I can have a mentor so that I can get to the next level, so that I can have a long-lasting career, or else I’m going to have to move back in with my parents.


[0:58:44.6] LW: Seeing as how TikTok was so good to you, I’m curious, what’s your social media platform of choice these days?


[0:58:50.3] SC: Twitter got ruined so like, I’m not on Twitter anymore, even though I have so many –


[0:58:53.1] LW: You’re not on Twitter?


[0:58:55.0] SC: I am but it’s just like, it’s just a hellscape right now. It’s just a hellhole, it’s awful, I hate it.


[0:59:01.8] LW: But hasn’t it always kind of have that bit of a toxic vibe?


[0:59:06.4] SC: It’s gotten worse, and worse and worse over time but yeah, you’re right. It has also – it has always been a bit toxic.


[0:59:11.4] LW: I feel like it’s perfect for you though. Just those spiffy one-liners, deep in my head right now, self-awareness.


[0:59:19.0] SC: Yeah, that’s why I’ve been trying Threads.


[0:59:20.1] LW: I’ve gotten to the point of writing where – what did you say that one time? I got into the point in writing where I’m questioning if – I forget what it was, it was so amazing though.


[0:59:31.2] SC: I’ve gotten to the point in writing where I’m questioning, what?


[0:59:35.1] LW: I’m questioning what writing even is or something like that. It was long ago.


[0:59:38.5] SC: Sounds like some – 


[0:59:40.2] LW: It was very Sarah “Cooperism.”


[0:59:40.8] SC: Yeah, I love those short things and I’m trying Threads now because of that and it’s kind of fun. Yeah, Instagram, Threads, TikTok.


[0:59:50.6] LW: So, no videos, you’re not really doing videos right now?


[0:59:53.3] SC: Well, I’m doing standup comedy and I’ll be like sharing clips of that.


[0:59:58.1] LW: That’s the thing with comedians, right? You got to try to do the crowd work, you got to share it.


[1:00:03.6] SC: Yeah, and it’s actually really great because that muscle of being in front of an audience and thinking on your feet, that’s – like I said, that’s the holy grail for me is being on that stage and being myself and so, I don’t want to give up on that.


[1:00:19.2] LW: Are you doing the Andrew Schultz and bringing a whole film crew every time you go to perform and how to get up and making the reels and being very intentional about it?


[1:00:27.4] SC: No, I’m working on material and if crowd work happens, it happens and if it doesn’t, it doesn’t.


[1:00:32.2] LW: But are you recording it?


[1:00:34.1] SC: A lot of the clubs just record automatically so I don’t have to do anything other than show up and then get the clip, you know? And then I have to caption it, which is annoying.


[1:00:43.9] LW: Are you able to get on pretty much any club you turn up to now, nowadays?


[1:00:50.2] SC: No, no. I actually – because I spend so much time doing other things this year like you know, I did the play, I wrote this book, like I am rusty as hell with standup right now. So, I’ve just started performing again and I’m just trucking along.


[1:01:06.6] LW: What are your go-to venues in New York?


[1:01:08.6] SC: New York Comedy Club, Eastville, West Side Comedy Club.


[1:01:13.1] LW: And do you have a routine where every Friday, people can potentially see you at one of those venues?


[1:01:19.5] SC: Yeah. I mean, if you check the schedules of those, you’ll see when I’ll be performing but it’s like, kind of a weekly thing of just – when you go up, they set the schedule. It’s kind of like working at any place, they tell you when to show up each week, yeah.


[1:01:32.2] LW: Are you going to be performing tonight?


[1:01:34.7] SC: Not tonight. So, I’ll be performing tomorrow night at West Side Comedy Club.


[1:01:38.0] LW: Beautiful. Back to where it all started. I love it.


[1:01:42.1] SC: Kind of, pretty much, yeah. It’s all full circle with me.


[1:01:47.5] LW: Last question. How are you thinking about success these days?


[1:01:51.1] SC: Yeah, it’s just about consistent work, consistently putting stuff out and consistent income, consistent work, that’s success to me. I’m hoping that I can do this for the rest of my life and that just means that I just got to be consistent about it.


[1:02:05.8] LW: Beautiful. Well, Foolish is the book.


[1:02:09.3] SC: It is.


[1:02:09.4] LW: Sarah Cooper is the guest. The Light Show is the podcast.


[1:02:14.8] SC: Light, thank you so much for letting me be on your podcast again, a second-time guest, it’s very special, and I hope you are going to be in New York sometime.


[1:02:24.9] LW: Yeah. Thank you for accepting the invitation and I will definitely let you know when I’m in the city again. I want to see you perform, I’ve never seen you perform live.


[1:02:31.6] SC: Yeah, you should come.


[1:02:32.8] LW: But that will be a box that I would like to check one day.




[1:02:36.5] SC: Thank you for tuning in to my interview with author and comedian, Sarah Cooper. You can follow Sarah on the socials, @sarahcooper and her book Foolish is available everywhere books are sold and of course, I’ll put links in the show notes to everything we talked about, you can find that at, and if you enjoyed our conversation and you found it inspiring, and you’re thinking to yourself, “Wow, I’d love to hear Light interview someone like Oprah” Or “Barack Obama.” 


Here’s how you can make that interview happen: Go to my podcast page on Apple Podcast. So, if you’re listening to this on Apple Podcast, just look at your device, click on the name of the show, The Light Watkins Show, scroll down past those first seven or eight episodes, you’ll see a space with five blank stars, click the star on the right and you’ve left a five-star rating, which means, you voted for this podcast having a highly engaged audience. 


And when I reach out to potential guests, the first thing they do is they go to my podcast page, they look at the ratings, they look at the reviews and they see, “Is this an engaged audience?” and if so, they are more likely to say yes to my invitation than if not. So, thank you very much in advance for your rating and if you want to go the extra mile, of course, you can leave a review, and if you want to see these podcast episodes and put a personality to the story, you can always watch it on my YouTube channel, just go to YouTube and search Light Watkins Podcast and you’ll see the entire playlist.


Please also, make sure you subscribe there as well, and if you didn’t already know, I post the raw, unedited version of every episode in my Happiness Insiders Online community. So, if you want to hear all the mistakes and the false starts and the conversation in the beginning and the end of the episodes, you can listen to that by joining, and you’ll also get access to my mindful triathlon, 30-day challenge, and a bunch of other challenges and masterclasses for becoming the best version of you, okay?


I look forward to hopefully seeing you back here next week with another story about someone just like me, just like you, taking a leap of faith in the direction of their purpose, and until then, keep trusting your intuition, keep following your heart, keep taking those leaps of faith on your end, and if no one’s told you recently that they believe in you, I believe in you, so you got me in your corner. All right, thank you so much, sending you lots of love, and have a great day.



From Tech to Comedy
Late Start With Animals and Coffee
Journaling, Observations, and Self-Awareness
Journey to Self-Discovery and Success
Taking Risks and Following Your Passion
Navigating Change and Support in Relationships
Evolution of Friendships and Authenticity
Navigating Relationships and Self-Reflection
Sarah Cooper's Comedy and Social Media Journey
Podcast Episodes and Online Community Benefits