ALISON BEARD: Welcome to the HBR IdeaCast from Harvard Business Review. I’m Alison Beard.

You probably know today’s guest from her parody lip syncs of President Donald Trump, which spread like wildfire on social media during the pandemic. Some might have taken offense. I, and millions of others, found them hysterical.

But before all of that, this comedy star was poking fun at something even more pertinent for our listeners: the absurdities of the corporate world. Drawing on her experiences and observations working as a designer and manager at Google, she wrote two humor books: How to Appear Smart in Meetings and How to Be Successful Without Hurting Men’s Feelings.

And thanks to her Trump era fame, she’s now involved in TV, film, and more book projects – including the forthcoming Let’s Catch Up Soon: How I Won Friends, and Influenced People, Against My Will.

Sarah Cooper is an actress, comedian, writer, producer and global TikTok star, and she talked with me earlier this year about how to find humor in the more serious circumstances – from the Oval office to your own, how she’s navigated the ups and downs of her career, and how leaders can make corporations better places to be.

So, you started your work life at Yahoo and then Google, you were a designer on important projects at one of the top companies in the world’s fastest growing industry. Why did you decide to quit?

SARAH COOPER: Well, I quit many times. I mean I really, my childhood dream was to be an actress because I couldn’t sing. Performance was something that I was always drawn to, fascinated by and writing, as well. Digital design, that was kind of a creative outlet for me. But then when I turned 30, I remembered this pact that I made with myself when I was 17, that I would not give up on my dream of being an actress.

And so, I quit my job at Yahoo and tried to do acting, was kind of all over the place. I kind of just tried everything, I tried improv, I tried sketch, anything that I could do, I would, I would try. And, one thing that I hadn’t tried was standup comedy, so I tried that, I really found that I loved writing my own lines and kind of performing as myself.

And, I always like to take big bets on myself, so, at that point I was like, You know what? I’m ready to move to New York. And within a year, I was $20,000 in debt and it wasn’t going very well. And so, that’s when I joined Google and I was there for almost four years and I really liked working at Google, but there was something, again, I think I was just sort of born with this need to perform.

Even when I left Google, they made this like video for me where they were talking about the things that they would miss, and it wasn’t my leadership skills or my design vision or anything, it was just that I was fun to be in meetings with because I tried to enjoy myself and have fun.

And, I think when I wrote 10 Tricks to Appear Smart in Meetings, which was around July, 2014, it was the first time I combined my love of comedy and all of that stuff with what I knew in the corporate world.

And, they always say write what you know, I hate how these cliches just end up being so true, but they are really true. And I knew the corporate world because I was in meetings all the time and I finally wrote that, but in a funny way, and it just kind of clicked in a way that nothing I’d done before that really clicked.

And so, I just got to a point where I was I was managing this team, I was supposed to be a cheerleader and sort of get everyone motivated and yet, I didn’t have the motivation myself. And I was found myself just really wanting to write more and really having more of a passion for writing than what I was doing at Google, which sometimes you can kind of skate under the radar, but if you’re actually managing a team, it’s a lot harder. And I felt like I was sort of living this double life, which didn’t feel comfortable and I wanted to leave, I wanted to see where writing would take me.

I remember telling my manager that I was going to leave and he just said, “you can always come back.” And, I think that was where I realized that it was a bigger risk to stay than it was to leave.

ALISON BEARD: And so, you were known as something of a comedian at work. Did that help or hurt you professionally?

SARAH COOPER: I think it helped a lot, actually, especially, sadly as a woman. If you’re a woman in a male dominated industry, being someone who isn’t ambitious, it means that you are… It’s better, because ambitious women, women who are transparent about wanting to get ahead and wanting to have more power in their work life, a lot of times you are penalized for that.

And, I remember when I was promoted to be a manager, there was someone else who wanted it even more than I did and I asked, I said, “Why was I promoted and this guy wasn’t,” and it was, they said, because you didn’t actually want to be a manager. They promoted me because I wasn’t power seeking, I was enjoying what I was doing and I wasn’t going for anything because I knew that there was other things that I wanted to do with my life. So, I feel like comedy and being able to just be myself in meetings and also not take everything so seriously, in terms of my career at Google, actually helped me get ahead. And, it’s kind of a sad thing, but it’s true.

ALISON BEARD: Right. Well, it seems like you were creating a better, more comfortable team dynamic as a boss who could have fun than maybe someone who would’ve been more ambitious. And, you mentioned that tech is obviously a very white male dominated industry. Comedy is, too.

SARAH COOPER: It’s also, yeah.

ALISON BEARD: Yeah. So, what has it been like as a woman of color in each of those environments? The same? Different?

SARAH COOPER: Yeah. I feel like I’m just a glutton for punishment with both of these industries there is a sense that you kind of have to prove yourself a little bit more. If a white guy with a beer gets on stage, people are already like, “Yeah, this guy’s going to be funny,” they just give that guy the benefit of the doubt. And, it felt the same in tech where there was a certain look of a person in tech that if that person walked in, and it was usually a white guy, then it’s like, “:Oh yeah, we’re going to listen to this person,” more than someone like me who kind of had to prove that what I said mattered and was important and was impactful. So, I think in both, it’s just getting over that hump of how visual we are as a society in terms of how we judge people when we see them, we just have this sort of template in our head of like, oh, this is what this kind of person should look like and it’s hard to get rid of that.

ALISON BEARD: What were some of the key problems that you were trying to point out with the two books you wrote about the workplace?

SARAH COOPER: I think, the first one, pretty similar to what I did with the Trump impressions, is just this jealousy, really, as someone who is a woman of color, I can’t talk myself into things, I can’t talk myself out of things, I’ve never been able to do that. And so, to watch these guys in these meetings just have their little ways of making it look like they knew what they were talking about when you weren’t actually sure they knew what they were talking about, that’s kind of what I was pointing out. I felt like when you’re in a pretty hierarchical corporate world, everyone looks to the leaders to like, that’s how the leader’s behaving, they’re talking about scale, they’re asking if we can take a step back, they’re pacing around the room and you’re like, “Oh, that’s what success looks like, so let me imitate that.”

And so, what ends up happening is we kind of turn into robots in these meetings where we’re just kind of doing our little tricks and we’re not actually being present, and, although there are some people who didn’t realize it was satire, who didn’t realize I was actually making fun of it, I think a lot of people realize the true point of it, which is basically be yourself, be real, don’t talk in buzz words, don’t just lean on you, sort of kind of tricks to-

ALISON BEARD: If you don’t understand something, don’t pretend you do.

SARAH COOPER: Exactly. Say, “I don’t know,” say “I need someone to explain this to me. And, that’s kind of what I was pointing out and I feel like it’s holding up a mirror to all of that in the hopes that people will be like, You know what? I’m saying this, but that’s not actually what I mean or how I feel, so let me actually say what I mean and how I feel.

And then, in the second book, How to Be Successful Without Hurting Men’s Feelings, that was more an observation of how I sort of minimized myself in the workplace, how I tried to be more approachable and not be as direct. How women are just sort of given all of these rules about what to wear, how to sound, how much to smile, how much not to smile, how to do your hair, how much to assert yourself, or not, emails, how many smiley faces do you use, how many exclamation points do you use-

ALISON BEARD: Oh gosh, I use so many exclamation points.

SARAH COOPER: I do, too.

ALISON BEARD: It’s awful. But then I think to myself, I don’t sound nice if I’m not saying it with a cheerful exclamation point!

SARAH COOPER: Exactly. And men, for some reason, they don’t feel the need to do those things, for the most part. And so, I wanted to point that out and give women kind of… Women read it and they’re like, “Oh my God. Yes, this is my life,” and men read it, very surprisingly, much to my surprise, they read it and they’re like, “Oh wow. This is a kind of a window into this experience that I didn’t have before.”

ALISON BEARD: Yeah. So, after the books, you’re still doing standup comedy. How did you think about next steps?

SARAH COOPER: I mean, at the end of 2019, I was, again, thinking I’d go back to Google. I was really-

ALISON BEARD: To be clear, you’re not thinking about going back to Google now, right?

SARAH COOPER: I couldn’t, at this point.

ALISON BEARD: Okay.

SARAH COOPER:

I couldn’t go back to Google. Then again, maybe, maybe I’ll go back to Google. I think when you think you’re going to write a book and you think it’s going to be this huge bestseller and it’s going to change your life and you’re going to have all these opportunities. And my first book, that definitely did not happen, my second book, that also did not happen. I’ve always wanted to do TV and I was really having trouble breaking through and getting meetings with people and even when I did get the meetings, again, I was terrified and it was really hard for me to be myself and so those meetings didn’t go anywhere.

When you turned 42, you’re just like, wait a second. I have to think about retirement soon, I have to think about my future, I don’t know if this is sustainable. And so, I was, I was really thinking maybe going back to Google, at least for a few years, would be good for me. And then, the Trump videos happened. Trump happened, the pandemic happened and those videos happened, which were just a confluence of events that no one could have predicted. And, those things just changed my life.

ALISON BEARD: So, where did that lip syncing idea, the use of TikTok, where did that come from?

SARAH COOPER: It was a pretty long process to get there, actually. I think it was the summer of 2019, I hung out with my nephews, they were 11 and 16 at the time. And I was like, Show your old aunt Sarah TikTok.” Because I like learning about new things and I wanted to know what the hype was all about. And then when the pandemic hit and I couldn’t do open mics anymore, and I was kind of stuck inside my house, I was really browsing it a lot more and I came across a woman who, I don’t remember her name or anything, it was just a really, really short clip, it was Trump, it was a clip of Trump saying, “It may it bigger, it may get smaller, but whatever happens, we’ll be prepared.” And, it was this woman talking about her weight, she had basically taken what he was talking about him and talked about her weight and the fact that she’s wearing tights and she’s prepared, whether she’s going to get bigger or smaller.

But, just seeing his voice come out of a mouth that wasn’t, his just blew my mind. I was like, that’s so crazy, it makes me see it in a whole different way. And, he was doing the daily coronavirus press briefings at that time and so, I was listening to him to say absolutely nothing for several hours and it was very frustrating.

And so, I took a clip that I saw him do where they were what’s your plan to get this done? And, he said something like, “Well, we’re going to form a committee and it’s going to be a good committee and we’re going to make decisions and hopefully they’ll be the right decisions.” That’s literally what he said and I was like, You just said absolutely nothing and I took that clip and I just pretended to be one of those guys in the meetings. And so, that’s really where it came from.

ALISON BEARD: And when did you realize that it was becoming a huge deal and how did you respond?

SARAH COOPER: So, I had actually stopped doing them at that point, because at that point, I think a few other people had started lip syncing Trump, and I was like, well, this isn’t new or different anymore. But, then he did his infamous put light into the bodies and Chlorox into the veins speech, which at that time, TikTok had a 59 second limit on video clips and the clip was literally 59 seconds and it was just perfect.

And I saw the whole thing in my head, I saw me lip syncing it, I saw me grabbing the cleaner from underneath the sink and putting it in my veins, I saw everything. And I was like, “Well, I’ve kind of given up on this, but you know what? I just got to do this one clip because this is too good.”

And so, I recorded it took me like a few hours to do, and that was a Thursday night and by the next day it had almost a million views. And it really just took off, very similar to Tricks, just kind of took off on its own. But, even though that led to Jerry Seinfeld talking about me in the New York Times, really nothing really changed at that point. It was only maybe a month later when I continued to make the clips and got a call from Ellen and got a call from Jimmy Fallon and finally was able to get an agent, which is something I’d been trying to do forever, that’s when I started to realize, Oh, wow, this is actually changing the game for me.

ALISON BEARD: Yeah. So, there was this almost instantaneous fame, although I’m sure it didn’t feel like that for you after you’d been working on comedies for so long. But then you needed to figure out sort of how to harness the attention for good. How did you think about that, in terms of advancing sort of the message you were trying to get across, but then also your craft and your career?

SARAH COOPER: That was one of the things that I loved about doing those videos, which is it really combined everything that I was interested in, in terms of politics and performance and sort of being able to direct these videos and sort of put together these scenes. I was doing everything sort of on my own, but it was also a lot of people had checked out by then because they were so frustrated with everything that was going on and I think people started to check back in. And, the election was so important and it was really important for every single human being out there to vote. And so, it was really eye opening for me in terms of, I always thought that like, oh, if you want to do good in the world, then you have to start a charity, you have to-

ALISON BEARD: Run for office.

SARAH COOPER: Run for office, you have to volunteer on the weekends, you have to do all this stuff. And you can do those things, but as an artist, it’s so beautiful when you can make art that does those things inherently.

ALISON BEARD: Hmm. And then what about for your career? It was this moment where that you needed to seize. You had this big success and you needed to build on it. So, how did you work to make that happen?

SARAH COOPER: I don’t think I did, really. Everything is 2020 is such a blur, in terms of everything happening so fast and me meeting all of my heroes within the span of a few months and going to going from making Tik Toks on my iPhone in my bedroom to being on set with John Hamm and Natasha Lyonne and –

ALISON BEARD: And that was for your TV special?

SARAH COOPER: Yeah, for my Netflix special. I mean, everything just happened so quickly and I think I’m still trying to figure that out. Both of my books were optioned to become TV shows and now I’m learning how long that process is. And so, it’s still one of those things that’s really scary to me because it’s one thing to achieve success like that, it’s another thing to maintain it. And I think maintaining it is a whole different beast that I think, for me, I’m a little wary of because I don’t really want my face to be everywhere. I keep thinking, Oh, I don’t want people to get sick of me, even though it’s not like I’m Tom Cruise, I get recognized here and there, but I still have a long way to go to achieve the success that I really do want to achieve in the entertainment world.

And so, for me, it’s more about just taking it one step at a time. Not like 2020, because 2020 was just here’s this and this and this and this over a very short amount of time. And so, this year for me has really been about what’s important to me, how do I want to spend my time, what am I passionate about? And, 2021 was really more about taking a step back, using my own trick to appear smart in meetings. I took a step back and I considered the 60,000 foot view and I was trying, yeah. And so-

ALISON BEARD: Big picture.

SARAH COOPER: Yeah. Big picture, exactly all of those things.

ALISON BEARD: Widened the lens, yeah.

SARAH COOPER: Wow, you’re good at this.

ALISON BEARD: I do work for HBR.

And so, now you’re working on television pilots, you’re working on films. What are you learning?

SARAH COOPER: Well, the biggest thing that I’m learning is about truth and just how important it is to be connected to who you are. I think for a lot of my life, I spent a lot of time deferring to people who I thought knew better than I did and as a youngest child, growing up in a household where someone else was always making the decisions, I gravitate towards kind of sitting back and letting someone else take charge.

But when you get to a situation where it’s your idea, it’s your vision, you’re in charge, you’re the one who’s making these creative decisions and sometimes they’re big creative decisions, like which characters we’re going to be writing, and sometimes it’s tiny ones like should they say the line this way or this way, but every single one of those decisions is incredibly important and if you don’t have that connection with your own personal vision and your own idea of what you want to make, then it’s a disaster.

So, I think, for me, it’s getting in touch with that and trying to stick with it because, as you can see from my career, I have no trouble moving on, but in the TV world, it can take years for something to get made. And so, you can’t be a person that’s just going to be like, well, I want to do this and then, in a few months, well, I want to do something else. If you really want to get something made, it has to be something that you know you’re going to be passionate about today, tomorrow, five years from now.

ALISON BEARD: So let me ask you one more question. Why do you think it’s so important to laugh at sort of the absurdities and sometimes the atrocities of work life and politics instead of crying or yelling about them?

SARAH COOPER: I mean, I think laughing, crying, and yelling are all equally important, I do. Sometimes I do them all at the same time. But laughter, it can elevate you, it can make you see something in a different way, which, I think giving you a new perspective can give you a new way of solving a problem. You have to get angry, sometimes the best jokes come from being angry about something. I was so depressed after the 2016 election, I never thought I could write a book about women’s issues because I was just so disheartened and demoralized by everything that was happening. And then, I was like, you know what, there’s actually a book that I could write about all of these rules that women have to face and how they completely contradict each other.

And so, I find that the best satire makes you laugh and makes you think, and in making you think gives you a new perspective. Maybe it’s just, you know what? I’m not going to ask to take a step back in this meeting anymore, maybe it’s just making that small decision of just you know what? I’m going to, I’m going to try something different. And, I think laughing is, you can try to tell someone, Hey, you’re wrong, this is the right way to be, this is the right way to think about this, that will get you absolutely nowhere. But, if you make someone laugh at the truth of the situation, it opens a door that I don’t think could be opened otherwise.

ALISON BEARD: So, now are you going to mix it up? What’s the next area of comedy for you?

SARAH COOPER: So, I’ve kind of turned my observational eye onto myself and I’m writing sort of a memoir in essays that’s based on Dale Carnegie’s How To Win Friends and Influence People.

ALISON BEARD: Oh, management classic.

SARAH COOPER: Yes. Management classic that I had never… I’d heard of it, but Audible approached me, it’s pretty cool, actually, they approached me before any of this happened, they approached me in early 2019 to write this book, a modern feminist look at this book. At first I was like, all these principles that he has like smile and give compliments and admit your mistakes and all this stuff. I was like, That’s what women have been doing for centuries, what are you telling me?

But then through actually doing these things, remembering people’s names and thinking about influence, I really learned a lot about myself. And so, that’s what the book is really about is just discovering who I am through Dale Carnegie. So, that’s my next thing is really just observing myself and my family and, really, relationships, that’s really what I’m interested in now.

ALISON BEARD: Awesome. Well, thank you so much. I really appreciate it. It was so nice to talk to you.

SARAH COOPER: Thank you, Alison. This was great.

ALISON BEARD: That was writer actress and comedian Sarah Cooper.

If you liked this show and want to hear more, like my episode 745 conversation with soccer star Megan Rapinoe, you can find us on HBR.org or wherever you get your podcasts.

This episode was produced by Mary Dooe. We get technical help from Rob Eckhardt. Hannah Bates is our audio production assistant. Ian Fox is our audio product manager. Thanks for listenering to the HBR IdeaCast, I’m Alison Beard.