IMO with Michelle Obama and Craig Robinson - Get a Hobby, Be Happy with Jessica Williams

Episode Date: June 10, 2026

On this episode of IMO, actress, host, and podcast veteran Jessica Williams joins the show! She discusses what it was like to have Jon Stewart as a mentor during her early tenure at The Daily Show, how she has had to approach her acting career as a tall Black woman in Hollywood, and the surprising crafting projects she’s picked up in her down time. Plus, Jessica shares her favorite stories from behind the scenes of Shrinking.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I'm doing a rom-com right now that I think you'll be really excited about. It's like me and a shorter, a guy who's shorter than me. I love that. And I'm really excited. And I was like trying to tell him, I was like, look at Tom and Zendaya. And he's like, no, I'm not going to Google that. But I know for me, it's my info is Tom and Zendaya. And I love looking at, but I just want, I love looking at them walking around in London with their little dog.

And he's a little short king and she's a tall queen and it just looks so right. It just looks so right. And it's like, why, Hollywood? Why? We can do this. We can do this. This episode of IMO is brought to you by Progressive Insurance. Howdy.

Craig Robinson. This is very comfortable. It looks like a pajama top. Well, that's what it's supposed to. It's fashion, as I say. Really? There's the look. It's the pajama.

No wonder kids are wearing pajamas to school. Who's giggling about pajamas? It's like. Crystal, it looks like a pajama top. And it's supposed to look like. What's so funny? I'm just making an observation. It's just you not knowing things about the world and fashion. It's not a pajama's top because I like my pajamas.

It's not a pajama's top. It just looks like it mimics a pajama. It mimics sort of the comfortable boholy. But if it actually looks like a pajama top, why couldn't you wear a pajama top? There's, you could. And some people do actually wear the pajama top as fashion. This just happens to be a blouse that is fashioned after a pajama. Okay. And there's also, now, I don't know whether this had bottoms, but a look would be this exact same bottom, matching the bottoms. Right.

Have you seen people walking around the airport like that? It's probably not their pajamas. I have learned something because I thought they were pajamas. It could be a very high and expensive pantsuit. Yeah. Yeah. Because you wouldn't want to wear it to bed after you wore it around the airport. I just like this look because it's.

is my look. Well, it's working for you. Let's get Jessica out here. She's my friend. I just met her. She's going to be nicer to you than I am. Her mom likes me. Oh, my God.

Her mom likes me, though. Yeah, you don't know. She better be nice to me. I'm going to tell her mom. That's true. She'll get it. Oh, my goodness. Let's do our official introduction.

So we have today, Jessica Williams, a two-time Emmy and Critics Choice nominated comedian, writer, and performer, who currently stars as Gabby in Apple TV's hit comedy series Shrinking, which I happen to have seen. In 2016, she co-launched a podcast, Two Dope Queens, which became an HBO series. in 2018 with a four-hour-long special. And if I don't, if I remember correctly, you were on that. Yes. You were on that. Okay.

Yeah. Yeah. Just finished the introduction. So anyway, I did a podcast in 2016. Come on out, Jessica. Yeah. Wait, where do I go? Where do I go?

Welcome, fellow tall persons. And then I was on the daily show. I was the youngest ever correspondent. That show for now. Yeah, no. It just takes him so long to read. Hey, you? Wait, so you said, I'm excited.

Remember we joked about this carpet on carpet? Yes, carpet on carpet, big chairs. Get it in there. But once you get set, it's comfortable. Oh, it's set. You're not super comfortable. You're not going anywhere. I feel like I can just.

Welcome. Thank you. Wait, you said you've actually seen, you've seen our show. Do you not watch a lot of TV? No, I don't. He doesn't. It's hard for me to watch TV because I have. four children who are grown, two are 16 and 14.

So, and I'm coaching their teams and I'm, you know, I'm, I'm, I'm lifeing. Understood. So I got, if I'm watching your show, you know it must be good. Absolutely. Understood. Because you try not to be on the couch. No, because I would be sound asleep. Totally.

I get it. Watch all the stuff. She's like, you don't watch enough popular culture stuff. Yeah. I'm like, I'll be watching the inside of my eyelids. I know, that's right. That's like the most dad, old man thing. It's watching the inside of my island.

Because he is. He's a dad old man. I know. I know. I know. He's very on brand for you. I know. He's in the quarter zip.

I know. With his fashion stuff. Here's my take on what I just watched with you too. Okay. I was watching. I was like, wow. What an intro. Both of y'all look dope.

Everything's working. You know, for the both, obviously. So you, you know, I mean, he, of course, he harped on the fact that your mother told you to say, Hein and King. Yes, right. My mom said, obviously, I didn't tell her until the last minute.

She was at my house just now. She was like, where are you going? I said, oh, I'm about to do IMO. And she went, she, like, walked across the living room to give me a hug and all this stuff. And then she was like, well, obviously, please tell Michelle, I love her example.

She said, I love her success. And I wish her all, I'm sending her all to love. And then don't forget Craig. She said, please don't forget Craig. Tell him, I love him and all this stuff. And, you know, she said it's going to be easy. They're Midwest people. My mom, my family's from Ohio.

So they're like, there is a difference. We were just in Ohio. We were in Yellow Springs, Ohio, near Springfield. And just, you know, salt to the earth kind of thing. Friendly. Yeah. Hey, how you doing? It's just great.

Hey, how you doing is very nice. That doesn't happen. That doesn't happen as much as you think it would. Yeah, especially in L.A. Totally. Hey, how you doing? Yeah. All right.

First loaded question. obviously you're a pro at this. We're just starting out here. How are we doing? Great. This is like lovely. There's like some lovely people here. You guys can't see there's a timer.

We've got this gorgeous color. It's in between a pink and an orange and there's a little brown. It's coral. It is coral. And there's coral. I mean, I love it. This is really nice. And you guys have a great banter.

Yeah. It's been built up over the years. Over many, many years. Yeah. And everybody I talk to this on this. podcast loves doing it, which is a good sign. I wouldn't say that if it wasn't true. I would be like, I was just not saying anything.

You said a very good example. One of my first podcast. No way, was it? I wasn't, you know, when we weren't into the podcast thing. Podcasting wasn't a thing when we were in the White House. I mean, we sort of kept to trend when it came to communications, you know, but I don't remember ever going on a podcast when I was first lady. Oh, we were totally honored.

Like, that was insane. It was really cool. So doing you guys, and you guys came to my office, which was so cool. Yeah. You know, and incredibly impressed by the two of you. What made you want to do a podcast? Oh, got these people in this room. They were like, you know what would be great for higher ground audio?

It's like if you did a podcast. And then I was like, I don't know. And they were like, what if Craig did it with you? And then I was like, oh, all right. So it's really a combination of them and him. Well, I have a craft room now in my house where I just do like crafting. And so I am. Yeah. And sewing and yeah, it's like how I stay sane.

But I have you guys say it and I just listen to you guys while I'm like sewing and crafting. Because you have to. Like I was, you probably know, I got into my knitting phase. I didn't know that. Well, during COVID. Yeah, cool. So it's one of these things that's like, okay, we're going to be trapped in the house. I mean, you know, we had the former president who believed in science, so we knew what was coming, you know.

We would always be like, what do we have to do? They were like, stop washing the vegetables. That doesn't, you know. That's right. So, you know, he would talk to Fauci and really find out. Crazy to, like, listen to people who spent their whole lives studying something. Exactly. Exactly. So we were, you know, we understood what we needed to do.

We knew that we would need to hunker down. So I just started ordering crafts and stuff. like that, like paint brushes. And I saw, like, knitting needles. Okay, let's get, yeah, I used to crochet when I was little. So I got knitting needles and started learning the stitches. And before you know it, I made, then I made everything. Really? I mean, I made scarves. And then I made pillows. I made it an assignment. Then I was like, everybody's getting knitted gifts for Christmas. So I made pillows. And then I made a sweater. Then I started making hats. and I've made mittens before.

Yeah. So there's a long way of saying, you can't do anything when you're crafting except listen. That's right. You know? That's right. You got to lock in. Yeah.

Well, that's what I like about it. I'm always chasing flow state. No matter what that looks like, I want something. I'm trying to use my phone a lot less to. It's making me mad. I just look at me. I'm mad. What am I looking at?

What do? And then it's like, what am I communicating on Instagram? I'm like, it's like, look at what you don't have. Like, I don't want to do that. So I found that I'm happiest when I'm crafting, especially when I'm not working. So what are you making when you're crafting? I've been sewing. I've been sewing like a mad woman.

I think I have a, I left it in the car. I had a, I made a heart-shaped purse that I, like, sewed. I used a quilting cotton, but it's like a ditsy fabric. So kind of like grandma, like you would get it out like a countryside in. It's puffy. I patted it because I wanted to put my laptop in it. And it's a big red heart. I quilted it.

And then it has ruffles on it. Oh, wow. Another thing I made a pair of shorts. They're like two different legs. Well, the other thing is because I'm tall. That's the best thing. Like, yeah. Because we're tall.

I think sizes are just a suggestion. But they do better now. Totally. Totally. Very inclusive. I can actually buy things off of offline. Me too. Yeah.

And then, but there's also like a really good like, there's like a unisex runoff because of like drag culture and stuff that I've benefited from. And like pushing the limits of sexuality and gender, I can find bigger shoes. Like shoes now will go to like 11. 11. Yeah, I'm now, I'm 10.5. 11. 11.

Yeah. 11. 11. 11. And it's, it's been a struggle. But now it's like really cool. Yeah. They're doing better.

I know. But shorts with separate legs. Yeah. They're just two different fabrics. Oh. But I mean, but I can do whatever I want. He's very style. He's style ignorant.

No, she was like, when you have a hand. No, hang on a second. Can I? What do you mean? No, you were saying that and then you were cut off before you could finish telling me about the way. It went a different direction. Shots right. I was interested in understanding what two different legs were.

Okay. Well, I also made a quilt top. Okay. That's not fashion. That's just more of a home good. I mean, there's nothing more satisfied. then like, I did this and I can put it on and carry it out into the world. And you know you have a million gifts.

Now you have a million gift ideas. And it matters more than like, to me than like this really, really nice purse. It's also very sustainable. It's like making stuff out of things you have. Did you, were you crafty as a kid? Or did you? No, I was more performing arts. I was doing like I went to, I grew up here in L.A.

It's called the South Bay. So it's more like the beach cities like Torrance, Redolph. that area, Harbor City. And I knew I wanted to do performing arts when I was a kid. And here, it's a lot easier to do performing arts. I went to public school. So I did, I would do drama festivals, Shakespeare festivals, school musicals. And then we had a high school improv team when I was in high school and I tried out for my high school improv team. And I got on there. And that sort of started my my comedy tracked and like my love for for comedy. Were you always this person that we see before you?

I don't know. You're quick. You're confident. You're confident. You're on top of it. No. No, I don't think so. I mean, a lot comes with being black, being a girl, being tall.

And I was always tall. And you know, you know, I was just talking about that. I love talking about being tall of people that are tall. I don't like talking about being tall of people that aren't tall. They don't get it. I feel very safe here. You are very safe. Very safe.

We know. Very safe. We know. Would you consider yourself shy? Were you ever shy? Yeah. Yeah. Really?

Totally. I'm like on right now because I'm working. But when I'm home, like, imagine I get in my car. I'm like, thank you, Craig in the show. Thank you.

And I just go like that. And I power down. I just go. And then my driver, Juan's going to be like, are you okay? And I go, take me out. I'm done. I'm just done.

I'm off. How old were? you when you realized you wanted to be an actor. Ooh, really young. I got a really nice sweet spot of TV. It was before Nickelodeon and Disney became 24-hour networks. There was like a time where, as a millennial,

I'm 36, so we got to see like all that. There was like sketch comedy, Keenan and Kel. There was a lot of really funny stuff that was made for kids. But then at about 8, 8.30, they would start showing like happy days, escape to Rich Mountain, Lassie. So you still got like older

stuff. Like it wasn't, they they would have something called Vault Disney. So it wasn't like you just watch stuff for kids. You watched everything. I remember Fresh Prince really meant a lot to me as a kid. Men in black, like Will Smith really meant a lot to me. Just talking about Queen Latifah really meant a lot to me. Whoopi Goldberg.

Just like these women, these like black women who could play in rom-coms and can really, they can do it all. And then I got Saturday Night Live and Matt TV, which my grandma lived in the valley. And when she'd watched me, she would let me stay up late. and she would drink a Colt 45 and she's from Ohio. She lived really hard. And I would get her diabetes medication

but also I would go get her her beer. It's like, here we go. Totally. I got my girl stacked up. As I'm a girl! Like a friggin' seven-year-old is insane. But I really like, I just thought she was like the most beautiful person ever,

this like lady who watched TV all day. But I just, she just had the best since she would watch South Park. She would watch a little swim. She was just really bawdy. She would watch it. Carol Burnett. Like she just, we watched the nanny. Oh, of course.

I got all that stuff from her. We got so teared up with her. I mean, Carol Burnett meant so much to our family and our sense of humor. And she is as lovely in person. I love to me her. Oh, my God. I thought that was such a blessing to be able to like watching. Yeah, it was amazing.

I really love that show. But again, I got to see all these things, but I didn't know that that was, I was getting an education in. all sorts of TV and culture with her. Yeah. It was really nice. Did you grow up, did you have brothers and sisters? Yeah. I have an older sister and I have a younger brother, but we're all really different.

My brother's more, he played football, come from a football family. And then my older sister likes business. She likes like local politics and stuff like that. So my sister, I think she works for the teachers unions right now. So she reps, she reps teachers in the university system. Yeah. So we all were in different. lanes. She would run for student body and all that stuff. And I got to do drama club, Shakespeare

Club. Did you guys go to school together? We did. We went to school together. My brother went to a football school. But there's something really nice about not overlapping. We all had just different interests. And so I got to be like the middle child. What's your your birth order? How many siblings do you have? Because I think birth order is the new, I think it's the new astrology. I agree. I see it. And our kids, we see it. He has four. I have two. I'm a million. Sasha, and it's very much their personalities and the choices they make because the younger child, you're trying to define yourself against the older. So there was a lot of things, oh, I'm not doing that, or I'm doing that because you're not doing that. And you know, you're a younger kid,

so how much of it was your choice and how much of it were you battling against somebody else? It's like your first friend, like your sibling is like, I feel very lucky to have mine. Like, mine's make me laugh all the time. I'm like, I just, sometimes somebody's like, especially with my brother, I'm like, ha ha, ha, you're my best friend is what I'm thinking. And then I'll see him and my sister. And I'll go, look at the both of them. So beautiful, so handsome. I'm so happy to know you.

I feel like that's like my 30s is being like, look at this family. I like all of us. That's nice. Like, I feel very, very blessed to have that. Did your sister try and protect you when she was younger? But she was annoyed because me and my brother were like, we're not listening to you, like what? And then my sister. is more, she's like the person that I would imagine is the closest to Beyonce who doesn't

try to be Beyonce. Oh, yeah. Just really gorgeous and glamorous and works really hard and just all the really, really lovely things that she would love in a beautiful black woman. And then I feel more like, I'm just, you know, my braids are grown out. My braids are grown out. My underwear is starting to get too tight. It's kind of, I got to order some new underwear, but I don't feel like it.

I don't feel like it. Just kind of barely hanging on, you know? It's like, oh, I got to go do this podcast. Should I shave my legs? Probably not. I'm like lucky to, like a bunch of people put this together and rolled me over here. It's like a car. Totally.

Your face is beat. Yeah. Do you do your own makeup? Never. No, I do like makeup a lot, actually. And I love it. But I have this, I have two women that I love that does my makeup. And the one who does this makeup is, I'm very lucky.

She's very. silly, very goofy. She's like very silly. You ever have that surprise where you're like, oh my gosh, this person is so silly. Just what you need. To have somebody in your face, you have to like them and feel their energy. Totally. It feels like I'm hanging out with my friend. And the person who does my hair too, I feel, they're like two goofs. They become, when you are in the public eye, your team becomes your family because you're with them more than you're with, you know, your own family sometimes. Do you like getting your hair and makeup done? You know, I like the people in the same way. I enjoy that more. But I'm like you, when I'm down, I'm down. I mean,

you know, I structure my life around hair and makeup. It's like, let's get it all in. You know, it's like having an update. Stack them up. Stack them up. Because I don't want to have to do this. And don't touch me. That's right. Don't touch me. That's right. I feel like it's having a good diet. You get it. You get it. I have no idea what you all they're talking about. It's true, though, so much of what we do, especially because, oh my God, people are so mean. So mean online, people are so mean. They are. I spend most of my day.

That's why you can't look. No, I can't. But most of my life, I feel like, is leaving my house and trying not to get my feelings hurt. Really? Yes, like at the store. Or people just be like, oh my God, you're so much prettier than I thought. Like just even things like that.

Like that. Yeah. And I'm just here at Albertsons. Yeah. You get that. Totally. It's like, oh, you're really pretty in person. Oh, my God.

What picture were they looking at it? I'd be looking at. See, you needed an older brother. See, he would have calloused you for all of that. Totally. He would have pung to luck. I mean, I don't know. But still, like, Phil. That didn't work?

No, I'm so sensitive. And it's, there's, I, as I get older, I'm like, that's just how I am. This episode is brought to you by Progressive Insurance, a company committed to helping people move forward and live fully. Mish, what is one of the best? biggest swings or leaps of faith you've taken professionally or otherwise. For me, you remember it was when I left investment banking to go into assistant coaching. That was a big swing for me. I remember calling you and you helping me to be okay with that decision. Yeah, yeah. I mean, I've had a lot of big swings. I mean, you know, me leaving my job at the law firm where I was making a ton of money.

in corporate law and deciding to go and work in government and public service where it cut my salary in half. And I remember how guilty I felt for going to mom and dad and even expressing an interest to do something that I cared about rather than something that would make the absolute most money. I mean, at the time I was making my salary was more than both mom and dad's salary combined. How do you think your age at the time shaped that decision? Do big decisions feel more or less daunting at different stages of life. Oh, my God, that felt like the biggest decision that I would make. I mean, I had invested so much in getting my law degree and then to walk away from it,

it was scary. But we've talked about it. Once you make that first scary leap, you know, that first hard decision and you realize that you land pretty solidly on the other side of that leap. You get comfortable with taking those risks and understanding. So yes, age definitely makes the difference because now, you know, I'm more confident in my ability that when I take a big swing, that I'm pretty, I have the tools to land wherever I need to land. You know, it feels easier to make big decisions when you're young because if they don't work out,

you don't have a lot of people to, you don't have a lot to lose. It's harder when you're older because now the stakes are higher. That's true. And more people are relying on these decisions to be the right one. All of our listeners have faced big decisions and their fair share of uncertainty. I remember the first time I ever bought a house, one of the biggest leaps you ever take. I was really intimidated by the whole process. But when the time came, all I could do was trust my gut and have faith.

that it was the right decision. Progressive understands the hurdles first-time homebuyers are facing, including housing affordability challenges and a lack of straightforward education that could make the home buying process feel less intimidating. Progressive's Open the House initiative is committed to breaking down these barriers and making first times a little easier. Since In 2020, Progressive has committed more than $16 million towards making the dream of home ownership more achievable. This includes a $3.5 million investment this year towards the Up Payment, Progressive's down payment assistant program aimed at first-time homebuyers. Learn more about the Up Payment Program and Progressive's commitment to first-time homebuyers at Progressive.com slash open the house where homebuyers can discover more about housing challenges and access resources and

support to empower them in their housing journey. Did you feel pretty? I mean, this is another tall girl thing. No. It's like when you're a tall girl, you know, it's like you don't start feeling pretty until you're an adult and you can, you really realize that it's like, oh, I really like this height. Totally. And a lot of, go ahead. And part of the problem is, you know, part of the problem is is you don't meet tall guys until later because it takes us so long to catch up. Yeah. Hight-wise.

I mean, the big part of it, the overarching is media standards and our diet. Our media diet, actually, is so counter to physically what we look like. Right. It's the opposite, actually. And if nobody's talking to you about it, I feel like now we have that conversation

about what are we looking at on TV, who's desirable on TV, who is considered petite, or feminine, which is what's valued in a heteronormative society. Like our media diet is what is the overarching thing. You know, when they do the doll test and, you know, those studies. But, you know, that's the big thing. And so I think if you're a person of color, you are, we are downloading that our entire

lives and taking away whatever it is, especially since it's nothing you ever really say out loud. Yep. But for me, it's like. You know better. You know better than to say it. It's not like we were taught that. I mean, I know my parents and my brother.

brother, they thought I was beautiful. Totally. You know, so it wasn't, you know, so it's when you're at school. Why are you doing that? I don't know, but I'm doing, but I'm doing it. I'm doing it, but I only did it. You know, this is like, his sense of humor is sort of like, what are you doing? But he's closest to me.

So I'm in-prone, I had to yes and him, you know, so I guess, but like, great job. I don't know. I'm a term, I'm a term, but totally, like, I, so no, I did it because I'm very, I'm a a feeler. I'm very sensitive. Like, there's no, you know. And then, you know, when you're on TV and you do events, they, like, pay people to make sure you look good. Yeah. So it's like a lot. It's like, you know, who you are when you're at home, brawless, you know, watching Real Housewives of Rhode Island.

Can you imagine they did Rhode Island? No. They did. Did you see it? Yes. I just watched it last night. I used my time. It's crazy. I know you don't know what it is. No. I don't want to get into it. No, go ahead. What did you think? I'm enjoying it thoroughly. He's supposed to be watching one. So we're going to pick one.

Go ahead. I said, why don't I watch Rhode Island? Because it's the new one. Everybody's here. And you know what she said? Don't watch that. No, don't watch that. It's not going to be any good.

Now she's watching it. I told them. I missed it. Well, I watched them all. Yeah, me too. That's not a measure, you know. What's your recommendation for him, though? I think Potomac.

Yeah, I think Potomac. Potomac. Potomac is the one where like, I actually am laughing with them because they are very funny. Yeah, yeah. I think Potomac start two seasons ago. Yeah. Yeah, I guess you don't have to start from the beginning. You don't have to. No, I want them to see that whole evolution. So I have to watch it from the beginning. No, no, no, no. We have a limited time. We know we have a limited runway. So we're saying start from like two seasons ago. And no, it's a lot of seasons. A lot. Yeah. It's more than like eight episodes. You can do it. Do it for the team. Yeah, definitely. You know, you're for.

You're professional now. You're professional. I mean, this is the other thing. You can't be in podcasting and not know pop culture. You can't. Like you can't. Here we go. You know, I might have to replace him.

No, I'm just kidding. Here we go. That's funny. You guys. Are you free, Jessica? Yeah. With you? Yeah, I live right over here.

Definitely. What about 90 day? Do you watch 90 Day, fiancé? You know that. I watch glimpses of 90 day, but I, that I have a hard time. There's a lot of that. I can't recommend it in good. Conscious. Either you do watch it or you know or you don't. I can't. TLC's tough. I've watched it. Yeah. But I it's like I can watch anything. I'd have trouble watching that. That's how bad it is. It's not good for your soul. TLC is you have Bravo and you're like, okay, Andy's, Andy's behind the strings and you're like, there's a standard. TLC, you're like, this is, this is, what am I watching? What do you think of Rhode Island so far? I love it. It's got everything. There's a lot of drama that's happened.

So much drama. The camera started rolling. They're all so messy. Totally. I also wasn't expecting the accents. Like, I realized I didn't know anything about Rhode Island. I was just thinking that the other day. I didn't know what to expect from Rhode Island.

There's a really strong like, he's over here. You're like, I didn't know this is what I'm going to get, but I want it. See, that's why I was going to watch. We used to live in Rhode Island. Really? Oh, yeah, I forgot. Don't watch. Still don't.

It's not the one. I won't. Well, we don't know. It's still too new. Okay. It's still too new. Yeah. Yeah.

Potomac, I'm going to jump right in two seasons. Then you got to get it in. It's fun. I'll get it. Well, now I'm wondering, tell me about your parents, you know. They raged you. Yeah. Creative, interesting people.

What would they like? My mom liked football players and bouncing, who become bouncers. And that's why I'm tall. I'm just trying to tell you why I'm tall as my mom has a type. And especially as I get older, I'm like, that's really cute. Like, my mom's always. Like, my mom was like, how's W. Camel Bell? Have you spoken to him in a while? And I'm like, oh, brother. Like, she loves like a tall, a tall black man. And so, yeah, I think she met my stepdad.

We have a really blended family. She met my stepdad at the Ohio State University. And my real dad, I think she met at the Ohio State University, because they're Ohio people. Then she moved to L.A., lived in, like, Highland Park for a while. There was, like, some clubs, like the golden tail that like black people used to go to and like deaf comedy jam, my dad, my stepdad is like bodyguard and bouncer on the circuit, police officer, all those things. And then they reconnected here.

And then they got married. And I, they came, my dad came with my two siblings. My older sister and my younger brother. And they raised us together in the South Bay, which is about 20 miles south of here, which is a really nice place to grow up. You're like, in L.A., but you're not, so you can have a really, really nice normal life.

And I don't know, they were always very encouraging because my dad did a lot of entertainment. And they're always really encouraging of the arts. And so they all kind of let us be ourselves. They were tough on me. Like I went to like a gifted and talented program, tested into that, went to a magnet school, had to transfer schools to go to a predominantly like kind of white and Korean and Japanese program. And then was your neighborhood diverse? Yeah, my neighborhood was, but I had to go a little farther more to like Pallas Verde, San Pedro area to go to school because I read a lot.

And then I went to high school and they had a really great performing arts program, super underfunded, L-A-U-S-D, but a really great performing arts program. So I did a lot of that, did improv and then did Uprice Citizens Brigade when I got in college. And then I went to Kelsey Long Beach. You went to Cal State. I went to Cal State Long Beach. And then I did up for Citizens Brigade and something called Comedy Sports. And then I got the Daily Show

while I was doing that. How old were you? 22. I was 22 and I got that. I know. Now that I'm 36 and I'm like, wow. Baby bowler. Yeah.

Totally. You said baby baller? Mm-hmm. Mm-hmm. Yeah. Yeah, I was a baby baller. Yeah, I was a baby baller. It was one of those things where they didn't know how I got hired.

Like, I was auditioning for Allison Jones for this Will Ferrell movie. And she was like, you might be too young, they're casting the Daily Show. Can you come back in and do these two sides? And it was like a stand-up where you have a green screen background. And then there was a thing at the desk where you're like talking to John and you're at the desk. And I was like, sure.

And then I did that and they sent the tape in. And then maybe two days later, I was at the Panda Express on my campus. There was like a Panda Express there in between classes. And they were like, John Stewart saw your tape. He wants to fly you out to audition with him in New York. What do you do when you get the? that call. I screamed. I think I had an undercut, like Rihanna's undercut. I think I had

green hair. I remember my best friend and I screamed and my mom took me to T.J. Max and we got like a Jones New York suit and I just remember flying out. It was so cold because it was in Hell's Kitchen. The wind whips around. I felt like I was in like a Broadway musical where I'm on

the streets of New York and I'm scared and I'm 20. I'm going to make it in showbiz. And I'm going to And I just remember auditioning with him, him just being so nice, and just being like, you know, I'll talk to you soon. And he auditioned me by being like, hey, I'm John Stewart. Like, it's so nice to meet you. I already saw your tape.

You're so funny. All you have to do is, like, be present with me. And that really released me. And I do really well with mentors like that who are very nice because I'm so sensitive. I don't do well with mean mentors. which I think that can work for people. Another reason why sports were hard for me because I need somebody to really be nice to me.

He's a mean coach. Yeah, I mean, it works. We're not all a monolith. You know, some people need to be tough. Some people need their asses whoop, too. Like, some people need it, you know? But he was very sweet. It's like I could tell, some people you can tell her girl dads.

Like, there's something about working with a girl dad who's a good girl dad where you're like, that's good. They made you better. Like, you've learned a lot having girls. I like the way you deal with women in your life. So anyway, I got that job pretty quickly. I say that a lot because it was the kind of audition where he wasn't making it seem like I had to prove myself. And at 22, black girl, I needed that, especially coming up in comedy because there's like, especially at that time, a lot of mean white guys in comedy actually.

And who are like, you're not funny. You have to prove yourself to be funny, like all that stuff. and I had had a lot of that up into that point. So was that your, how did you know what to do on the Daily Show? I mean, it's like- It's a machine. Like, it's been, it had been going for a really long time. And as a correspondent, your day is watching the news all day.

You're looking for stories. People are pitching stories. And then there's like a field producer segment. And those are like, they're kind of broie, at least when I was there. It's like the guys that you go to Utah with and you interview somebody who's going to say, like, we should eat babies and you're like, tell me more. And you have those packages and then you have the stuff that you do with John. And then a lot of those people went to Ivy Leagues.

And it's like two kind of separate things. And then you kind of ping pong back and forth. But there's like a schedule. But when you're 22, you know, it was like grad, I didn't finish college, but it felt like grad school. You learn to kill your darlings just because it's funny. It doesn't mean it's going to make it. You learn how to work for one person. You know, you're, I were editing these field pieces.

And it depends on how John's feeling that day. But it's like watching his reaction. But that's important to work for someone. It's important to be like, oh, he didn't like this as much. And just because you think it should be some way at the end of the day, that's your boss. And you're going to do it that way. And then also, we had been in a room full of people. And I would be sort of like, oh, like, I have something to say about Coney 2012.

And he'd be like, yes, Jessica. Like, what do you think? You know, in this whole room full of people. So he was a really good boss for me for that. And I learned a lot. about who I was. And it's also a really nice way to move to New York. It's like on somebody else's dime with a job.

Where'd you live? I lived in Hell's Kitchen first. And then Wyatt Snack was like Mr. Brooklyn. And he was like, I'm going to show you something about Brooklyn. Like, this is place. Yeah. So then I lived in Williamsburg, Clinton Hill, Prospect Heights all over. How long were you there?

About 10 years. And then I COVID happened. So you grew up? My parents. Yeah, totally. My 20s. I spent my 20s there. And it was great.

Like I, this is, L.A. is like my heart and my soul, but New York really affected me profoundly. What was the hardest part about working on the daily show? I think doing field pieces. Like, I think traveling and you're going to a rally. It's very scary, you know, doing that is, it takes guts. Interviewing someone, you know, in the middle of Florida, you know, is really scary. And you know, you're going to, you know, you're going to have to do bits and get it out. You know, you don't know if they're going to freak out or something.

And I remember having quite a bit of anxiety. And sometimes I would text the other correspondence, like, here I go. You know, I hope I get what I need. But, yeah, especially now. It's like what they're doing, like Jordan and Desi and Ronnie. And, you know, it's like, and Josh, it's like really cool that they're doing that. But for me, it gave me a lot of anxiety, especially coming up more introverted. Yeah, yeah.

Just have to, you know, that's life we chose. That's the job. Wow. Were you glad to be doing it? Did you feel like you were. in your sweet spot. Absolutely. It was really nice to have you guys in the White House.

Yeah, it was nice. It was like, it's harder now, I think, because it was just so much. Yeah. There's so much. And it's really, really, really, really like a trigger point now. But yes, it was great. It was funny. The Daily Show is something where you wouldn't know, you don't know who's watching it.

And you would get really cool people that watch the show, which is really nice. But, yeah, I learned so much. But it's hard because with that and podcasting, I was like, I always knew I was an actor. So I had to do like a hard pivot and be like, oh, well, I started this as an actor. I just so happened to do improv and really like comedy. Yeah. That's got to take a lot of courage because you got this regular job and you're doing well.

And then, but you know you were destined for something else. So how and when did you decide, okay, this is enough. I got to follow my passion. Totally. I mean, it was really hard. People were like, oh, like, we want you. you to run the Daily Show. They're like, oh, we want you to host the daily show.

And I'm thinking, I don't want to. No, thanks. I love them. I love it. It's a hard job. You do it every night. I want to imagine people are like, for me, it's like, when I told people I was doing this, they were like, tell Michelle we wanted to be president.

I was like, she doesn't want to be freaking president. Like, what are you talking about? Let that woman rest. They don't know what the job is. I know, but you do. You don't know what they do. You do. You do.

If you wanted to, you would do it. That's right. That's right. What are you talking about. You know? And so it was, I remember one day, it was this whole to do. It was also just like, you host. And I was like, I don't want to do that. You know how much work that is? You don't want to see your family? I'm looking at the news like this all day. Then I have to put on a suit. I don't want to wear a suit. But you do look better in a suit when you're hosting it. You have to wear a suit. You know, I don't want to do that.

Oh, my God. Oh, my God. No. No, girl. I want to listen to salon. I want to sew a tote bag. Okay. I want to sew a tote bag. Okay. That's right. That's who I am. You don't bet it. And you have to know that I know better than you because I watch people do the job. And I know what it takes to do the job. I know better than you. You know, so it's like, tell Michelle. And it's like, don't you want her to run for president?

No, I don't. No. Why? She did it. We're good. Let her freaking do her whatever, you know. But let her knit and deal with chal asses. But yeah.

So, you know, it is hard to leave something that was like my womb. But I never thought, like, since John, John went back, and since I've gotten to do shrinking, that I get to go back. And so I've done a couple of bits going back home. It's like getting a taste. Being able to dabble, and it is very different. They're the best over there. They're like, whenever you want to do something, let us know.

It's like, great. But I never thought I'd be able to work with John again in that capacity, and I feel very lucky. This episode is brought to you by Progressive Insurance, a company committed to helping people move forward and live fully. So buying your first home can feel like this huge exciting milestone. And it is, but it can also feel confusing and deeply overwhelming. That's one of the reasons I appreciate all the work Progressive is doing to help first-time homebuyers. The Up Payment Program is part of Progressive's Open the House initiative, a multi-year commitment to giving people the tools and knowledge they need to make home ownership a reality. And this year, Progressive is expanding their

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Always. In acting. Okay. No offense to all of Hollywood. They're so small. I know. They're such small people. Totally. And I always miss. I don't see anyone. Because I'm looking for, that's X, and I'm looking up. They're down. And I miss them.

They walk right past my waist. They're like, you didn't know. That was Tom Cruise. I would know. I thought Tom Cruise was my height. Totally. You know? Totally. I'm doing a rom-com right now that I think you'll be really excited about.

It's like me and a shorter, a guy who's shorter than me. I love that. And I'm really excited. And I was like trying to tell him, I was like, look at Tom and Zendaya. And he's like, no, I'm not going to Google that. But I know for me, it's my info is Tom and Zendaya. And I love looking at, but I just want, I love looking at them walking around in London with their little dog. And he's a little short king and she's a tall queen.

And it just looks so right. It just looks so right. And it's like, why, Hollywood? Why? It looks good. We can do this. We can do this. So I'm trying to take it. I'm trying to take it back. Because it's ridiculous. There's a weird, like, doll, baby doll Barbie and Ken thing. That's like, if you're tall, you can't be with somebody short. But it looks really good. You'd be under the arm of the gun. Totally. And sometimes I still watch that. I still watch women who are underneath somebody's arm. And I'm like, I don't even know what that feels like. No, Zendaya takes Tom as she just grabs him. He's right on her middle. And he's grabbing it. They're both grabbing each other like,

I love paparazzi photos. Thank you guys so much if you're watching. It really means a lot to me in the tall woman community. But I really hope to take back the rom-com and be like, I think that sounds amazing. It's actually really lovely. On the tall woman side, you know, the fact that women's athletics has really developed and we were seeing all types of bodies

and images. And it's, I feel so good about the next generation of girls. coming up. I don't know about you, but when I meet a tall young girl, I stop. I know me too. And I'm like, girl, you are, this is exciting. Me too. You know, and I see you and stand tall, you know, do not worry about this. You will grow into it. It will be fabulous. But we didn't have those wrong. You know, there was. When I see tall young girls, I stopped too. And I tell them, they didn't make them like that when I was younger. Yeah. Especially like, when I was, When you think, I'm sorry, when you think about you two, you all aren't that tall.

You're tall, but you're not like, I'm still, I'm 5'10. Yeah. I'm 5.11. I'm 6, but then when you add the shoes and you have the hair and the thing, you know, it feels. And also presence. Like, I'm not going to, I think my presence feels tall. So how is it getting cast when you're, you know, when everybody is 5, 6 and it's hard? Yeah.

Yeah, it's really hard. People, I think, there's a lot in this business about people hiring the same people over and over. Like, sometimes I look at movie trailers and I'm like, I just saw all these people in a different movie. And now it's like, and now we're bringing you them in a different movie. And you're like, you know, we have to work to make it look different. You know, and then there's something about being like not mixed also, which means you work less considerably. You know, every show, there's like a lovely mixed young lady. on the show and that benefits everyone because she can have a white parent and a black parent.

And it's, again, our media diet. It's like, what are we saying? And then being tall on top of that, it's like really, really hard to get cast. You just have to, you can't rest. You have to prove yourself all the time. But I feel lucky to be on Trinking because we shoot that like five or six months out of the year. And she's by my house. And it's just another opportunity for me to just show what I know I can do. I do think if you keep chipping away at something, if you just keep doing it, you keep showing up, then finally things will open for you. Oh, thank you so much. You really are. I mean, that's one of my favorite shows. I mean, I've had the opportunity to meet Harrison and, oh, yeah, my God, he's so sweet. One of the sweetest people in the world trying to get him on

the show, but I'll corner him into that. I'm going to try to guilt him. It's like the former first lady really want you on the show. He's like, okay, well, what? Like, I don't know. I don't even know how you would begin to do that. I feel lucky that we get him to act. Yeah, totally. We were just with, I was just with him the last two days and, like, he's just a maniac. He's our, especially on set, he's like our

son. I mean, it's Jason's show, but Harrison is like the sun and we're the solar system around him. We're like, ready. We're like, is he here? All right, let's do it, you know? Or he'll be like, some days he'll be like, I'm already acting. I'm already acting. I'm already acting, and then the crew rest would be like, you know. But it just depends on how he's feeling.

But he's like, you know, he's earned it. Yeah. He, sometimes I'll just look at him and they've wiggled him into doing press, you know, and I'll be like, he was at the cast party for like Indiana Jones. He's at the cast party for what lies beneath. Like, he was, like, he's at the cast party for witness. You know, this is how long he's been. That's right.

Acting, you know, he doesn't have to do any of it, really. And so I feel very lucky. But you feel like your relationship. holding your own. I mean, you're toe to toe with... Thank you. I have no, you know, I have no choice. Why am I going to let, let Harrison Ford do gobble me up on screen? No. Yeah, right. No, I'm competitive. Yeah, I don't do sports, but I like to think I'm athletic and I'm very competitive. And one thing I'm going to do is make the scene mine. I always my... Have you seen Annie Hall?

Have you seen Annie Hall? There's this lobster scene in Annie Hall that's totally, you can tell like an improvised spontaneous moment and they're giggling and you're just like, wow, like Diane is giggling and you're like, this is everything I want in my career is like an improvised moment. I want every time I do something on camera for it to feel like it's happening for the first time. And, you know, I want to, if Harrison has an idea, I want to yes and and be like, I want to make my screen partner look good. that's a big part of being a supporting character too is like, I'm going to put my oxygen mask on and then I'm going to help you. How do we make this happen?

And how do we make this scene look alive? So for Gabby especially, the character I play with such a heart-led person, I'm always trying to be like, okay, now what feels, how can we have a lobster moment? What feels spontaneous? I wanted to feel like you look at it and you're like, oh, only Jessica could do that. That's kind of my goal, I think. But yes, casting is hard. There's no, there's no, like, you really have to get people to try and think of you, but I can't force it.

So in the meantime, when I'm off and not working, I like to sew, I have hobbies, and I have a full life. That's kind of the goal. Like, I act, but I want a really full life. Yeah. Yeah. Yeah. Well, you, and that affects your work. I mean, you start seeing these actors who just, they become other people.

and it changes the way they show up. It's really easy because when you're an actor, you're on set, people can get you anything you want. You're like a baby, basically. Everybody knows where you are. They're like, do you need something? I can get it for you, and you become this weird baby person.

And it breeds a lot of mental illness. It does. And I get it. Like, I really want my union to have more health services specifically for actors because you have, you know, it's so mean, Our business is so mean. The casting doesn't make sense sometimes.

You're fighting for these parts. It's very small. And, you know, there's the white guy on set. There's number one on the call sheet. You don't know if he's doing method. You don't know what his thing is. Is he going to make it easy for you? Is he going to make it hard?

You might still have to kiss them. Like, you know, you don't. It's its own thing. And it is like a really, really kind of baby job. Like, there's so many important jobs. But acting is like, it is the most baby. like, look at me. I'm feeling emotions.

Like, it's so embarrassing, actually. It's a really embarrassing job. So when I see guys talking about the craft, like, it's like, shut up. Shut your ass. You cry, baby. You just got paid to cry on camera. It's cool.

It's a craft. But you're not a surgeon. It's like you're not saving lives. You're not saving lives. You didn't fix the ozone layer. It's elected. Our job is elective. Jessica, everybody.

can't do it. Like, if somebody like me, I fascinated at consuming acting. Really? You like, you like the good acting. I like to watch. I like to watch. And sometimes, even if it's not good, I don't mind sort of watching people attempt to do things. It's like a sport. Me too. It's like, I appreciate the fact that you've had to work. Me too. All of this and get up there and then mess it up. Me too. I like a medium experience. Like, I think online, people, like, this movie didn't blow my balls off. And you're like, you want your blows, your balls blown off every time you watch something.

You can just have a perfectly medium time. That's right. And it's good. Like, bring back a medium time. I think it's kind of destroying art. Or medium less, like that's okay. Like, it's fine. I think it makes studios take less of a chance on art.

Because everybody needs to have their life changed every time. No, we have to try and fail. It is a goofy job where if you do it right, you get an insane amount of money for a tiny amount of work. And I'm calling that out because a lot of actors walk around like they're, you know, changing the world. And it's like, I guess, but this is art that we get. It's a privilege.

Yeah. So, yeah. But I do love good acting. My partner knows, like, if I see good acting, he'll just turn to me like, do you want to rewind that? And I go, yeah, they're cooking. Like, I'll rewind things when I see it. So that means your partner knows good acting.

I think so. I think he does just from. like us being together. It's like, like, I want to see it. Like, I want to see cooking. And I think there's nothing. But that's what I like about reality shows, like Real Housewives. You want to watch steaks. Okay, Craig. Listen, you want to talk to him. These women are acting. That's right. They're like, you look at me weird. Like, it's like, that is my point to my sister that it is not reality TV. No, it's not reality. It's acting. Nobody's saying nobody's arguing. I'm not saying this is so real. And that's why.

And it's like, oh my God. It's just, it's entertaining. It's funny. I think it's like when Andy Warhol came out with pop culture and people were like, what is this? This is a can of soup. I think it's that. I think really amazing things happen in reality TV. And I think it's really important.

And it shows us something about ourselves as a society. And it should be watched. It should be studied. It should be analyzed. Because you were breaking down characters, behaviors, things you've seen before. I mean, I think it's. also, look, I tease him because what you said about acting, I say all the time about sports. You know, I mean, it's, you know, societally, we have decided what type of entertainment is relevant or good or worthwhile, right?

And it's like reality TV is, it's sociology, it's empathy, it's analyzing behavior. I mean, it's like the, it's like the emies of like, great. Girl, let's break down that conversation. Totally. Totally. Which is very female. Totally. You know.

Totally. But what gets, what do we spend money on? What gets the awards? Somebody throwing a ball. It's like, okay, you're good at throwing. You can jump high, but that's what you, that's all you do. Totally. You've been trained, yeah.

This is what you've done. So you should be good at it. And you're tall. Totally. You won the genetic lottery. Or genetics, right? You fit the bill. You're a gymnast because you're 4-11.

And I tried. I tried. That's another thing tall people can't do. A backflip. Couldn't do it. Too much going around. It's too much going around the mountain when it comes. Yeah, you got the gravity.

Because you do the first part of the backflip, you're like, that was a lot. But you got to bring the legs, go their long legs. All of them. Yeah. Yeah. No. So I do think it's very gendered. I make this argument only because so many people make the opposite argument when it's something they don't understand.

Totally. You know, that's the only reason I make the argument. It's mainly to men to say, wait, wait, wait, wait a minute, right? Yeah. You know, what you like is only, you know, credible because men have decided it is. Right. That's right. That's why. I agree. You know, it's not because it is objectively, it's a skill for sure. It's a really cool skill, too. Totally. You know, whatever the sport is. Anybody who becomes a master at something they do, it's fascinating to watch. I know, I like it too. I feel like that's why I like talking to people about anything, really.

Especially when you travel and you're like, oh, you're a master shoe shiner. Like, tell me more, genuinely. What kind of, you know, what's it like when somebody has smelly feet? You're shoe shining. What's that about? How do you deal with it? How do you cope?

Do you have a regular? What do you guys talk about? Do you shine your own shoes or are you over it? What's the best kind of shoe to shine? You know? Like, really? Like, I really care about that. We can go in.

I think people That's why people are endlessly fascinating And it's what you choose to find interesting That matters And I do think reality TV It's like you should you could My dream and I've said this quite a bit Is toward the end of my life

When I'm a professor somewhere They're like an honorary professor teacher Reality Studies class And like what does it say? Yeah What do the Kardashians say? What does it reflect back to us as a culture? What does it mean?

You know, that that What do you think it means these days? Well, there's so much reality TV. It's hard to choose just one thing. It's a valid medium and it's doing really, really well. But it does show us like Love Island showed us a lot. Did you ever watch this last two seasons of Love Island? Yes.

You are my friend. You are my friend. The girls introduced me. I didn't really know about it. I would pass over it. And then one day, it was this one summer. Was it COVID? I don't know what, no, it wasn't COVID because it wasn't.

wasn't on, but the girls were into it, and it was the thing, it came on every day. And I was like, oh, I was, I was, I was, I was, like, yeah, of course. How could watching these kids and these bathing suits become a thing? And then they were like, just sit down and watch with us, mom. And I couldn't stop. Absolutely. I couldn't stop. I mean, and there was a discussion, deep discussion after every episode. Totally. We'd have to stop. I mean, especially this last season, there was a lot of, like, race politics that came into play. There were fandoms that came into play. there was like somebody like, you know, as beautiful as O'Landria, you're like, am I taking crazy pills here?

Am I taking crazy? This is like one of the most stunning women I've ever seen. But when you're in this sort of fishbowl of like people whose beauty standards are one way, you're just like, oh, this is really, really weird. And then that's why I love it's like when she got out of the house, it's like she's going to fashion. It's like what she deserves. But it did spawn a lot of conversation over fandoms and race and the United States. States. And then the season before that, there was some weird, like, Dominican American stuff.

Like, it was like, it really highlighted. It's like a weird fishbowl and it brought up some racial politics like of like heteronormative romance in a way that I think is really interesting. And it is the easy, it is lazy to me for people to count that out because it's reality TV. There's so much there. That's right. But that's why I think it's like really important. 90 day fiance is its own thing that's saying a lot. a lot of crazy stuff about immigration. And, you know, a lot of times I'm rooting for the women trying to get in this country that I know in their home country make a dollar an hour.

And they're like talking to this old guy and they're like a hot young thing trying to get into the United States. I'm like, yeah, yeah, get away of life. Shoot your shot. Get away a life. You know, it's like, I don't know. There's just so much. We've got our viewer question.

Yeah. Okay, we have a question. Yes. Let me help. Okay, let me help you. Yeah, this is from Benedetta. And Benedetta does not want us to know where she's from. At 37, as a black woman, I am finding myself at a bit of a crossroads.

I've recently graduated from a leadership program. And while I've been fortunate to land interviews and receive great feedback, I'm struggling to close the opportunities. It's incredibly frustrating, especially as I find myself applying for roles I know I can excel in. There's a lingering uncertainty that I can't quite shake. what more can I do to make the leap into a role that truly aligns with my aspirations? I know that career journeys aren't linear, but I'm reaching out because I'd love to hear your thoughts on staying motivated during this process. How do you keep pushing through the uncertainty

without settling when the pressure to take anything that comes your way is so real? Your advice would mean the world to me, and that is from Benedetta, who is 37. It's really hard because what I could of use and what I could use when I was an actor is like sometimes people just aren't going to hire you because you're black. And like you feel like you're taking crazy pills. You're like, oh, I can't get this job. Oh, I can't. And you do all these things and you see other people get in. Maybe you're more qualified. And like, it's like you're not crazy actually. Like you're sometimes you're just not going to get it. Yeah. Because you're black. We are the history of our country makes it so that we are, it's actually harder for us to get jobs. And that's very real and like sit with that. I think for a second and that's okay. But then also, it's like okay to be disappointed, I feel like. There's that, too. It's like feeling like, you know, feeling like you're disappointed in the system comes with being the human experience, I feel like. But also keep, you got to keep going.

And make sure you fill your life with things that you enjoy that remind you of who you are, Like whether it's, you know, for me crafting, making sure you laugh with your friends, doing things that fill your tank is really important. Even when you get the job I know you're going to get, it's like make sure you fill your tank because work isn't the only thing. It's like you have a whole full life and you are a person outside of this job and make sure you hold on to that because it'll make the stress of not working in the field that you want to like work in a little easier, I think. And what do you guys think? You know, it's the, how do you stay focused? I think sometimes you need to be ready to take an alternative path because it depends on what your circumstances are.

I mean, I wouldn't tell somebody, just hold on to your dream regardless of anything because you might not be able to do it. And flexibility and adaptability is part of life, you know. I mean, I don't want to discourage anybody from pursuing their dreams, but you got to eat, you know. A good part of happiness and feelings sustained is like I'm taking care of my family, paying my bills. And sometimes, you know, look, this whole notion of having the career that makes you

happy and fulfills you, I think is a relatively new goal. Our parents took jobs and they worked and they did what they had to do to pay the bills. I don't think my father, who was a stationary fireman at the water filtration plant all his life, who was an artist? He was a gifted painter and sculptor. He couldn't do it because he had us. And so he made the call that I'm going to work for the city, make a good salary, send my kids to college. Most of people in life are doing things that don't bring them passion. It's like so they find it in other things. And I think I would say keep an open mind to what is really possible to and be ready to pivot.

you know, and try not to be too disappointed with the pivot. Because that, it's how you feel about the pivot sometimes that can determine it all. If you feel like I gave up everything and I can't be happy now or I failed because I didn't do this thing in the way that I thought it was done. You know, that's all in our heads and our hearts, you know. I mean, you know, it is not a statement of anything other than maybe you just, just didn't, it didn't work out. At that time. At that time.

And sometimes things don't work out. But don't let that block your happiness or define you. You know, keep going if you can, but be realistic if you can. You know, maybe. Yeah, you're also always surprised. Steve Jobs says that I'm really bad at quoting people, but I understand the essence of it. That's what I remember. Steve Jobs says that really cool thing about connecting the dots.

And like, you want to do one thing, but then you wind up doing something. else and then you wind up doing something else. But at the end, it all kind of came together, especially for him and making, you know, this Apple product. And it's like, you would be surprised, the root that you take to get to where you want. I found that's been true in my life and my career, which is the only thing I can really speak to. And then the other thing that you reminded me of is thinking of your thoughts as trains. Like I had a really good therapist wants to tell me, like, your thoughts are coming and going. You're on a subway platform. The trains are passing. and you can choose to get on the train or you can choose not to.

So when you're seeing this train that's like I'm a failure because I don't have the job I want right now, you can choose to get on the train or you can acknowledge it and see it and have it pass. But that reminded me of that just because you think that you're a failure today because you don't have this job today doesn't mean that that's actually what's true. That's right. Well, for Benedetta, from someone who has pivoted quite a bit in their career, I would say do not. be afraid to begin at the beginning. And that's where I think a lot of people get hung up on because they want to pivot into an equal or higher position. To your point about you're not going to always find something because you got to eat, you got to live, you got to raise your family.

You really have to think about starting from scratch. And that might mean, hey, I want to I want to be a basketball coach and you take a salary cut and you do something else on the side while you're creating this new opportunity for yourself. I agree with Mish where this is a new thing where people are actually actively trying to find the thing that they love to do because it feels like people are just absolutely so unhappy in their current situation. But I don't think it's, I think people have been thinking about this for a long time. They just haven't had the wherewithal to do it. And having done it a couple of times myself, you just have to get past the fear of starting from the beginning. And then the other thing that I would say is the Benedetta's 37, you said. So she's young enough where if you can keep your lifestyle at a manageable,

place. I think the reason that I could make that first jump from corporate America investment banking to coaching was I never took my lifestyle up to the big time bond trader level because I was always afraid that it wouldn't last. If you can manage to do that, it makes it easy to pivot. It makes it easier. Easier. Easier to pivot. Yeah, I mean, I think that this is separate from her, but like there is something where I say to much, much younger, much young. I'm talking like, they're like 18, 19, not to you, Benadette. You know you, my girl. But where I go, you ain't going to like a job all the time. Yes. You ain't going to like it. Yes. Someday, you're not supposed to. Sometimes you're going to work people you don't like. You can't just quit. You got to, you got to have a job. You

have paid a bills. Like, you're just not going to like it. So, that's a good. That's That's right. No, that's absolutely right. So? Yeah. That's not how it works. But you've got to admit, when you're doing something you like, it's easier on the days where you hate that. But you got to work for it. But, I mean, even this job, I love my job.

Some days, I'm not a morning person. I got to get up. It's just what we do. You just got to. There's always something you're not going to like. And so this idea that you have to like it all the time, I'm like, nah. Well, I'm living below your means, living within your means. I'm telling young people that all the time.

I mean, that's a key to freedom, you know. Totally. Well, Jessica. This has been cool. I had a blast. I had a blast. You guys were lovely. I wasn't worried.

I wasn't worried. Yeah. I know you guys. Oh, my God. I know you guys. It's like, it's like, I'm powering down, powering down. Jessica's off. I'm going to unpin my hair.

I'm going to do it in the car. My driver knows that's what's happening. Sometimes like in the car. my wig off sometimes. It's like goodbye. Totally. When I get in the black car? It's like, they know. But like, I had a blast. This is great. I'll do it again anytime. But thank you for having me. It's been in, I wasn't worried. Thanks for being here. You have, it's so much fun watching you. And you are killing it. Thank you. And just keep it up,

girl, represent us tall chicks out in the world. Keep opening up the opportunities for tall black women to do whatever we want. You were representing well. Thank you. And give your mom our love, even though, you know. Especially Craig. Yeah, whatever. Give her a hug for me. I will.

She'll love it. She's going to watch this and she's going to love it. She's going to be happy that I did that. Thank you. You did that thing. Thank you. Thank you, sweetie. Thanks again to our friends at Progressive Insurance for sponsoring this episode.

For more information, visit progressive.com slash open the house.