YBY ep 258: Sheri Flanders on pushing the boundaries of art and culture.

This week on Yes But Why, I spoke with Sheri Flanders, a Chicago-based actor, comedian, writer, and visual artist.

Sheri Flanders artist comedian journalistSheri Flanders is an instructor at the Second City Training Center in Chicago, and her performance background ranges from improv, stand up, musical theater, commercials, Shakespeare, corporate training and voice over work. Sheri is half of the interracial married sketch comedy duo, Flanders.

Flanders comedy promo

Sheri is a writer of sketch comedy, musicals, screenplays, satire, film reviews, and artist interview features. As a freelance journalist, her work has been featured in several publications including the Chicago Sun-Times, The Chicago Reader, Rescripted The Chicago Defender and McSweeney’s. In both 2020 and 2021, she was invited to cover the Sundance Film Festival as part of their Press Inclusion Initiative.

In this episode, we discuss all the ways in which Sheri has made art a priority in her life. She started out with a passion for fashion design that gave her an outlet for her creativity while also satisfying the need to build something with her hands. We talk about how difficult it can be to turn your art into a business (and how sometimes that’s not the right move).

Sheri Flanders NV Talent

We talk about the consulting company she started with her husband and the work they do helping small businesses with grant writing, branding and marketing. We talk about how much she loves her community in Chicago.

Sheri tells me about how her start in creative writing was working on a screenplay with her husband, and how that collaborative process led them both to take classes at Second City. Sheri talks about the Chicago improv community and doing bits with her husband. (So fun!) We talk about navigating life transitions and being patient with yourself during the process.


Support Sheri Flanders by reading her recent pieces in The Chicago Reader and the Chicago Sun-Times! You can also watch funny comedy videos she has made with her husband as the comedy duo, Flanders!


Yes But Why Podcast is a proud member of the HC Universal Network family of podcasts. Visit us at HCUniversalNetwork.com to join in on the fun. #YesButWhy #Podcast #HCUniversalNetwork

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This episode of Yes But Why is also sponsored by PodcastCadet.com. Go to PodcastCadet.com and put in offer code YBY20 to get 20% off your first consultation!

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(production notes: recorded zoom meeting with Rodecaster on 3/4/2021…posted on 4/12/2021)






TRANSCRIPT by Otter.ai

HOST  00:00

Hello, Yes But Why listeners, this is your host, Amy Jordan.   Welcome to Yes But Why episode 257 – my chat with artist, Sheri Flanders  But first, let’s talk about our sponsors.  Today’s episode of Yes But Why Podcast is sponsored by audible. Get your FREE audiobook download and your 30 day free trial at audibletrial.com/YESBUTWHY.   So I’ve been on a bit of a John Scalzi binge. His fiction is dark and I like it. First I listened to The Dispatcher read by Zachary Quinto. That was really good. Then I jumped head first into Lock In because my teen crush, Wil Wheaton is reading it. Juicy stuff so far.   Head on over to audibletrial.com/YESBUTWHY right now and download the app. You’ll get a free audiobook and access to hundreds of books and podcasts that are included with your membership. Now’s the time. Get Audible.    Yes But Why Podcast is also sponsored by PodcastCadet.com.   My husband and I run the company, PodcastCadet.com to help people with podcasting. We can help you with some little detail you can’t figure out or we can help you with all of your podcast episodes! Connect with us now at PodcastCadet.com . Use promo code YBY20 and you’ll get 20% off the first service or workshop you buy!   This week, Yes But Why chats with Sheri Flanders, a Chicago-based actor, comedian, writer, and visual artist. Listen in as we talk about her experiences with designing fashion, writing film reviews, and making comedy with her husband!  I now present to you: yes but why episode 258: Sheri Flanders on pushing the boundaries of art and culture.    Enjoy!  I’m Amy Jordan. And this is Yes But Why Podcast. Yeah. What was the first time in your life when you did a creative thing like performing or art? Where you were like, I really love this and I want this to be part of my whole life?


Sheri  02:44

Ooh, that’s a good question. I don’t know that I actually have ever been answered that asks that one. I did a lot of creative things as a youth. So I can’t say what came first. But I would say the biggest ones when I was young, were probably writing cuz I used to like write like lots of silly stories. And also my art taught me how to sew at a young age. So I guess actually, drawing predated sewing. But they were kind of linked. I learned how to draw, I eventually got into like, drawing images from fashion magazines. And my aunt taught me how to sew, which then kind of led me on this longer path to fashion. But yeah, so it was the visual arts initially. But then I also had two other sisters, I am the oldest. And so we would like sing songs together and do little skits together. So there was also kind of a informal performance portion to it as well. So yeah, I just cut out all the all the things creatively, pretty young age, and I just I think it’s always been with me, and it’s always been a thing I was going to do.


HOST  03:49

Did you always know even when you’re a really little that this would be something that you would be, like, super active in or?


Sheri  03:59

Yeah, cuz I mean, I think especially like, I’m from that kind of like working class of like, you know, you’re always thinking of like, what you’re going to do when you grew up, what’s going to be your career, and it’s always something very practical, like, what can you do? What are you good at? And I was somebody who was good at doing artistic things. And so it’s like, Well, clearly, you’re going to be an artist, whether or not one could actually make a living. And that was sort of beside the point. But it was like obviously, I was good with my hands. I was good with drawing creative things. And so like, yeah, I mean, there were certainly never like, I’m going to become a mathematician because I suck at math. All right.


HOST  04:37

Listen, I was like scientists, no magician now.


Sheri  04:41

I did want to become at one point a brain surgeon, but then I was like, I suck at math. So I can’t be this brain surgeon sucks at math. So clearly, I’m not going down that road.


HOST  04:51

Is there a lot of math in brain surgery? I wonder?


Sheri  04:54

I’m just kind of assumed like King Springer told me that they were bad in math. would be like you’re not operating.



Right? Like,



I don’t know, I don’t know how you.


HOST  05:09

I don’t know how you fix brains. So I guess



I don’t know. I was


HOST  05:16

like, a knife and a brain, right? And then I was like, No, I probably has to read books and make decisions about what is right and like, know about what angle the cut at and blah blah blah. Yeah, that’s math was really open for some math deficient brain surgeons for some reason. I don’t know why I’m trying to make that happen.


Sheri  05:39

Don’t make that one. That one go.


HOST  05:46

Oh, man, well, you know, so. So like you did your whole family go like, oh, Sherry’s definitely gonna be an artist like from early on. I mean, like, my family was definitely like, oh, Amy’s a performer. But there were also other performers that were adults in my family. So like, the idea of having it as a job was real in my like life, because there was a person who I knew who did. Is that something that happened in your life? Is that was that your experience?


Sheri  06:15

Yeah, absolutely. Um, well, you know, when I think of like, early influences, I mean, the biggest in my family was my aunt Regina. She’s passed since but, um, she was a singer, and a dancer in a reggae band. And her and her husband was called the reaganomics and they were amazing. She had a beautiful voice, she was gorgeous. And we would go out and see them play at all the various cultural festivals in town. And, you know, when I got to like a certain age as a teenager, my immediate family actually is their Muslim converts. And my extended family is Christian. And so my mom is fairly consistent. And I like conservatives not quite the right word, because it kind of has a different meaning in like African American families than it does in like, the public lexicon. But um, you know, we’re not she was not somebody who was like going to bars. And then I remember one year when I was like a teenager, she like, took me, not my younger sisters to go to a bar to see my heart perform on stage. And I was just, like, far into my heart, and I feel so good went up. And it was amazing. So, you know, like, she was huge, like, I wanted to be like her, no doubt, like she was a huge influence. And so yes, because she was there, there was also this Yes. Well, clearly, Sherry’s also going to be an artist to anybody who wanted to do that couldn’t do that, because there was this path, at least for certain concrete artistic jobs. Wow.


HOST  07:37

That’s great. I mean, it’s only just because, I mean, I definitely have my own experience. And but most people I talked to, either their parents are like, no, or, or, you know, they’re, they’re like, yeah, you should be an artist, but I don’t know what that is or where you find it. So there’s a lot of that.


Sheri  08:01

I mean, like, they didn’t necessarily have guidance on it. They’re sick. And there certainly was the like, you call it like, you got to be an artist, because like, that’s what you’re clearly good at doing. But also, that doesn’t necessarily mean you’re going to be like gainfully employed. And so we’re like, we’re going to pin all hopes on the future on your middle sister. Probably gonna go do something more practical, but like, hollywood dreams, kid, figure it out. Good luck. Man, that’s


HOST  08:29

great. I’m glad that you like reality. I’m glad that you did. Or when you did you actually follow those dreams? Or were you more conservative small? See, I think that’s how you differentiate by the way. It’s like conservative small see, is what you mean more, it’s like, she’s not going to bars, whereas capital see is more like, oh, that kind of, right. Yeah.


Sheri  08:55

He wasn’t like socially conservative, you know, in many ways. Just smile. See, like, Yeah. Like, what was the question?


HOST  09:06

It’s kind of just about, like, where are you? Where did you go with your creative interests? At that point? Were you were you able to jump into doing work in the arts? Or, you know, did you get a regular job? Because you were like, well, that’s great. You guys are supportive, but I need to make rent.


Sheri  09:28

It was Bo. Actually, I think my life has always like existed on two tracks, right. So like, on the one hand, like I did my first fashion show when I was 16. Right? There was a local organization in town, called fashion forward. And, you know, they brought together a bunch of young designers and we sewed our own things. We put them on models, and it was amazing. And so I always had the hands on, you know, fully in but at the same time, recognizing like, I don’t really know where I go with this in Indianapolis. Indiana, which is not the fashion mecca of the world. And so, I when I graduated from high school, you know, my parents are like, we love you, but we can’t afford to pay for you to go to college. Even though I had gotten accepted to the Art Institute of Chicago here, and I wanted to go and I had we had gone on the school visit, and they were like, We just can’t afford that beautiful art school. So I went for a few semesters to a local art school, part of ipy, what used to be called Heron School of Art, and tried to work and I went to the workforce, I did the retail management off the bat in the beginning. In fact, while I was doing that, I also did a little community theater. When I was in high school, I did some mostly costumes, and then slowly started moving on to the stage. And then after graduation, did some community theater. But then after time, I couldn’t really juggle both wanting to work and have a salary and be able to afford my own apartment and do that. So the theater portion kind of fell off, but I always stayed with the fashion portion. And then eventually, probably a decade later, I went back to college in Chicago to pursue fashion design, and got my fashion design degree.


HOST  11:19

Oh, awesome. So are you doing fashion design? Sort of like on your own previous, like, during the 10 years in between?


Sheri  11:28

Yes, yes, definitely, on my own, trying to like, launch my own brand with whatever that means. And the town such as Indianapolis, you know, all of my friends were artists in some rate, so either some people who are other designers, some people who are painters, a lot of musicians at that time, my ex husband was a musician. And so I was hanging with deep with music crew, music, guys, that thing was going on. So yeah, so I was always kind of nurtured by this artistic community, and always kind of artistic.


HOST  11:59

That’s nice that Indianapolis has such a vibrant, artistic community that you could find to this crowd of friends,


Sheri  12:06

I would not call it a vibrant.


HOST  12:09

Six of you. And that was everyone.


Sheri  12:12

I mean, it’s just like anywhere, it’s like, there’s lots of artists, it’s just, it’s not not vibrant. I mean, like, if you go to Indianapolis, you can find pockets of art, it’s just not as much as here in Chicago. And if you are looking for art in that capital A to try to stack it up against what folks might value in a larger city, there will certainly be a certain amount of like, looking down the nose at it in terms of, you know, what kind of art, what tastes are popular or whatever, sometimes, but fellow artists, great artists, just people doing art, just in that like very normal everyday, like I am an artist and I, you know, express myself and as artists, I’m just going to do it for my own enjoyment and maybe try to find my way, in a small town with people don’t always have the resources to get out of the city. Like I got out of Indianapolis, because I had a little tiny 401k it would be my retail management jobs, and I cashed it out. And that was my money to move out. And to be enrolled in college.


HOST  13:18

Wow. Good on you for doing that. 401k.


Sheri  13:22

Right. Everybody invest? Yeah, invest.


HOST  13:27

I don’t have any of those. I never had a job where that was the thing. So I’m glad that you have those. I hear about that. And I sound interested


Sheri  13:34

in much. It was like $700, like, let’s not get


HOST  13:40

if you want to go to another city, you only need a small nest egg to get yourself moving to actually get going. So that’s not too bad. That’s nice.


Sheri  13:52

I mean, but like, but that was like unheard of, for me like people like, but it was terrifying. Like I don’t want it to be like it was so easy. It was terrifying. I was not someone who had ever lived in a big city. Indianapolis is like not a small city, but it feels like a small town. So when I moved to Chicago, I thought I was gonna get killed and shot the way that everybody not from Chicago thinks it was going to happen in this town. I was scared to take the train. Because I was like, there’s no bar between the train and the platform. And I could fall off into that platform or somebody could push me in front of the train, like, you know, I was there were like homeless people on the street. That’s not a thing in Indianapolis, in the same way because it’s a driving town. So you know, poverty is like in pockets. And I wasn’t rich, but there’s like levels of poverty, obviously, until I was like my family I would say is like, lower upper class, right. Yeah. You know? Yep. Yeah. So it’s like, we had to change apartments every year because, you know, we couldn’t afford the rent at the end of the lease sort of thing, you know, so


HOST  14:56

yeah, it’s just a different get more expensive every year. I hate that. You





HOST  15:01

you’re like, I didn’t get richer.


Sheri  15:04

Yeah, my dad was a, you know, a vet, you know, get pstd at PTSD. And so, you know, there were struggles financially and things were not always easy. You know, my parents loved things. They worked hard. And they we may do but, you know, I certainly when I came to Chicago, I did not have the tool. I was very naive, like, existing in a big city was a huge learning curve.



Hmm. Big culture shock, huh?


Sheri  15:29

He Oh, yes. Oh, yes. Now, I still have a day my aunt will call me and be like, I heard there was a shooting in Chicago. Are you okay? And I’m like the city so big and alive. It’s okay. I have people


HOST  15:44

like that too. Or like, literally anything happens. And I’m like, Listen, I appreciate you calling me but this The city is a lot bigger than I think it is.


Sheri  15:53

But we all live on like one block.


HOST  15:58

I mean, don’t get me wrong. I do usually live right next to wherever it is. We heard this thing. And I was like, it’s not near me. Where was it? Oh, really? It was right there. Oh, yeah. That’s near my house. But



yeah, fine.


HOST  16:11

I’m fine. Because I don’t leave my home ever. So


Sheri  16:13

you find. There’s machine gun fire two blocks over actually like a few weeks ago. And like I heard it, I was like, that’s probably fireworks. I was like, that’s not fireworks. And I like went on Facebook, and somebody was like, police said it was a machine gun fire. And I’m like, okay, it’s fine. You know, but then also just like, brush it off and keep going at this point.


HOST  16:30

Yeah. I feel like right now, at this very moment. In the world. It’s a little bit crazier. Like, there are definitely shootings in places where it’s, it is surprising. There are shootings here, where you’re like, Wait, what? Somebody was shooting up a gas station where? So there’s a lot of wackiness, I think happening all over the place. And it’s like, not just sort of contained anymore. And I say contained with air quotes.


Sheri  17:00

But yeah, and I mean, I wouldn’t say that I live in the, you know, I live in Rogers Park, in Chicago. I don’t know if you’re familiar with Chicago. But it’s like the last neighborhood in north of the suburbs. And it’s a very, very on probably one of the most diverse neighborhoods on the north side, which is why I like it, and I like the air, but they’re certainly, you know, folks from other neighborhoods are like, I would never live in matters, that sort of thing. You know, it’s like, Don’t come here. But





HOST  17:37

No, I understand. I mean, people, people always have these weird opinions. I definitely happens. Yeah, in my town, as well, where they’re like, Oh, I don’t go over there. And it’s like, why? Like, it’s fine. Do you want to know where you shouldn’t go? I’ll tell you where not to go. But that’s not here. Oh, man. So we, before we get into the deep culture shock of Chicago, I, you know, I just did. I’m interested in, you know, your fashion design and the way that it manifested for you, like, it’s one thing to want to, you know, draw clothing and, you know, make people you know, put people in clothing, oh, I want them to look good, I want to put this, but the idea of making clothing is so I mean, there’s something so sort of, like natural and organic about this idea of wanting to create in this way, but like, also fabulous, like, you know, the fact that it got done a and b like this fashion show when you’re 16 that, that you really like, glossed over that real fast, but like, tell me so tell me more from from like, you know, artistic perspective, like, what moves you when you’re doing fashion design, like what’s your, what’s the thing that keeps you going with it? What, what makes you, you know, what drives you to continue doing it?


Sheri  19:02

Well, first of all, say, I let it go. I don’t do it anymore. Other than like, once in a while, I’ll make something to myself for fun. I’ve been out of it for a while now. How many years? But, but when I was younger, it was just as great way like this great mode of self expression. Like I mentioned before, like my family was Muslim. And I was definitely the black sheep of the family. I’ve definitely was an avid reader as discovered early on that I was an atheist. I like all this cool, Weird Science Fiction stuff. My parents like science fiction stuff too. So I don’t want to say that we’re so different. We’re actually a lot alike in a lot of ways. But I was definitely like, the next step over where I was more embracing of this level, you know, what would might be considered a more wild life or existence, the you know, more bohemian whatever artist life however you want. to phrase it, and they were more like we’re looking at this life more from a distance through books and through TV, but we’re not necessarily living in that way. But at the same time, I think they also admired it to a certain level, but it was living in that way. But being in a Muslim family, there is also like, well, we can’t be seen as allowing our daughter to be, you know, scandalous. So for me, you know, to be able to wear miniskirts, and you know, cool things like all the other teenagers. Well, the thing that I wanted to do was, had certain and I had certain restrictions on that. So I learned to play with fashion to be able to push those boundaries as much as possible. And quite frankly, often just had a change of clothing in my backpack. Like, maybe a teenager does it, but also I have kind of like this, like, you know, I spoke about being bad at math, but it’s not entirely true. I’m good at like, geometry, I’m good at like, kind of like I have a bit of an egg, all I can say it’s like an engineering brain being able to think abstractly. And I love to put things together with my hands. I love that idea of being able to turn something around in my mind’s eye and see it from all different sides and build it, how does the fabric, you know, work with each other different types of fabric on the scenes, I enjoyed it, I just enjoy it, it’s I like to spend a lot of time alone. And so like when you’re sewing something you can spend like Hours alone. And that’s kind of mental creative world. And then at the end, do you have something great to show for it. It’s just, it’s just fun. And then also, obviously, if you make something and you go out the world, you’re like, I look beautiful, or you style something. It was just this thing that I just enjoyed. And that’s been most of my art. It’s like I just at some point, enjoyed it. And then at certain point, it became a career. And when it became a career, I realized that the the doing it, from a hands on perspective, for my own enjoyment is different than turning into a career. You know, and then, you know, some of the fun fades when that happens.


HOST  22:06

Yeah, yeah, I recently saw, like this commercial, where it’s like a spoof on nine to five, but it’s five to nine about how between the hours of five and nine, you’re working on your own little craft, and how you can turn that into a business. And I was like, I thought we all agreed that was a bad thing to be selling to people. Like, it’s not that it’s bad, inherently, but like, don’t just tell everyone, that’s what you should do. Because it works for some people that does not work for other people, and you can’t just, it’s hard thing about art is that, like, you should just be able to enjoy it without having to worry about selling it or you know, figuring out how to pay your rent while doing it. Like it’s something so human to want to create something and I love this idea of you, you know, pushing boundaries with your fashion and like, you know, decorating your world a little bit more. And I’m sorry, that sort of the real world of it, which probably thinking about fashion design probably is very hard and crazy. You know,


Sheri  23:18

I didn’t have the personality for it. I’m not mean enough. And I can be planning me when I want to. But you know, like, I don’t have that that streak and to really do it in that way.


HOST  23:27

Yeah, you know, I think about that all the time. Like, there’s, there’s competition and there’s competition, like, you know, because, you know, sometimes I’ll say to people, you know, I’m not competitive, and they’ll go, Yeah, you are. And I was like, Yeah, but I’m additive. Like, I want to hurt everyone who does what I do, because I gotta be the only one or like,


Sheri  23:49

I haven’t even competitive that’s like vicious. Yeah,


HOST  23:53

I mean, but to a certain. Like, yeah, that’s kind of how you have to be in some of these. I mean, even acting, you know, like fashion design acting. It’s the same as you have to be cutthroat, you have to keep doing stuff, you have to, you know, move forward and in ways that like, maybe aren’t what you wanted to because it’s an uphill battle. And yeah, there’s so many people trying to vie for like two positions that happen once every 10 years that it’s like, you know, because it’s like, yeah, you can be in a film or you can have a runway show wherever you’d like. But yeah, you know, people aren’t going to give you millions and millions of dollars for your purses or your dresses until you get to a certain point. Like,


Sheri  24:37

and also like as a designer, one thing that I learned too late was that if you actually want to launch your own brand, you have to basically have a rich family member willing to give you like a million dollars. You can work your way up that way. Most of the people at the top are like I knew somebody, you know, it’s really hard to really walk in as a girl. from Indiana, but, but also like, I want to kind of like, add nuance to the whole, like, Is it for fun or is it for a job because also at the time that I was going to school for fashion design, I was going to school for full time. And I was working in retail management full time. So I was doing that belt about like nine to five, five to nine, nine all the time, and barely having time to eat or, like live a life. And so, like, in retail is a horrible, horrible field. And I was happy to leave it behind. And so comparatively, working in fashion was a dream, you know, to go from a job where were you like, you know, have, like, I was a manager, but you know, monitoring other people bathroom breaks or feeling like, Oh my gosh, I’ve been on my, you know, feet for nine hours straight. And I still have to work three more hours in this extra long shift. And I’m wearing high heels. And I can’t sit down. Right. And you know, there were points of doing that were like my hair was falling out. I was getting rashes, you know that type of stuff. But you know, I was super skinny cuz I was losing all this weight from stress. You know, so then like to be able to go to work and do something that is based in art is a blessing. Great. So I don’t want to discount the idea that like working in art fully demeans the art? Because I don’t think that’s true. I think there’s more nuance to it.


HOST  26:34

No, absolutely. Plus, I think it’s individual, the individual, it depends on what’s going on. Like, if you’re a big person out these days, I would say you need to be like, you know, loud, Instagram, like person to get any attention for anything. Like, if you want to be an actor, or if you want to be a fashion designer, somebody’s gonna notice you. So you have to be like, hey, check this out what’s going on? Like, and you have to do that no matter what rooms you’re walking into, is to be like, yeah, you know, everyone has to notice that I’m there. And they have to be happy that I’m there. And


Sheri  27:13

Hey, girl, yeah,


HOST  27:16

yeah. There’s there’s a lot of like, sort of that, that work. That is not real. I mean, I’m sure they go home and like,





HOST  27:26

But at the same time, like, that’s the effort that they have to put in, because that’s what people expect, right?


Sheri  27:33

I’m so glad that I like came up before the internet was so ubiquitous. Like I had an email at like graduation from high school, but like, I didn’t have anybody to email. It wasn’t till years later that I was like, Oh, this


HOST  27:46

is a daily part of my life. Yeah. When I went to college, they had a computer terminal in the like, main hall where they had the cafeteria. And that was the place you went to make your email, and check your email, and everyone in the whole campus, use that one email. I mean, use that one computer.


Sheri  28:10

That’s amazing. And that why Oh, my God. I remember, in high school, we went to I went to a big High School, and it was like very well funded, and it had all the things that was like the second biggest one in the state. And I remember at one point, they were like, Look, we have a computer lab, and we had a computer class. And we would be sitting in front of these computers like trying to figure out how to use Excel or something. And we’d be like, hey, teacher, can you help us with this, we’re kind of stumped. And they’re like, I don’t know how to use this. And so we were basically teaching ourselves It was such a weird time to imagine that there was a time when people didn’t really know the basics on how to navigate a computer.



Oh, 100%


HOST  28:54

we’ve been talking a little bit about this idea of like, the effort that is required to like sort of propel yourself in this art world, right? Certainly, in fact, yeah. In a lot of in a lot of stuff. But that didn’t stop you. You still do different performance and art that is, you know, pretty high stakes. How did you end up after after? How many years? First of all, how many years ago did





HOST  29:23

stop doing fashion design?


Sheri  29:26

Oh, I When did I stop? trying to think of when I was I think Miami was like the last time when I was doing it, like fully in earnest. And then it took a few years to like, kind of get it out of my soul. And I was there and I’m really bad with dates. So you’re gonna have to forgive me. It’s I think, I think I know, no, cuz, okay. I’m old. And, you know, I’m 44. So like, there was like, a decade I didn’t go to college directly. I After high school, I went, Okay, I went to college for like a semester or two, then I dropped out locally. And then I waited. So, you know, worked time to build up that 401k. Right, and then moves to Chicago. And only then that I go to Chicago and went to college and graduated. And that was 2007 when I graduated. And then I met my husband and we were together for a few years. And then we went to Miami. And then after Miami, it’s kind of right when?





HOST  30:42

no, he’s just trying to put them to bed. And he’s like, just trying to jump in attack me in this moment.


Sheri  30:47

Um, yeah, those are my my nieces and nephews.


HOST  30:56

So you were in Miami for a few years. And that’s when it kind of like, moved out of your sort of, like, artistic purview. And were you Was it because you just needed to, like, move forward from it? Or did you find something else?


Sheri  31:15

I think it was a confluence of a few things. When I graduated from college in 2007. I was right about the time that the there was the recession, and the market crashed. And when a market crashes, and there’s a recession, basically things like fashion are the first things to kind of know, right? And so like, I’m like looking for jobs, and I would find a job and then they’d be like, this business is going under, or you know, we can’t hire people on the way that we did. And so I did a lot of that’s when I started transitioning also into freelance, even though so I was still doing design. And I did it in a lot of different capacities working for a retailer, or doing freelance work working for like dance companies doing more work on like, the purchasing end of things. So I did a lot. And then when I, when we were in Miami, I was at my last like, big design role was at working for Perry Ellis. And by that time, I already had my own my backing up, my husband and I started our consulting business that time. And so then that, so then I just started like, fully transitioning out, they already kind of had it in my mind, like, practically I have to transition transition out of this career because it’s just not working in the way that you know, I want it to. But then also, I do think there was an element of I started being you know, my love affair with the design when I was a child, right. And now I’m like an adult. And now I’m like, ready for the next creative movement, big time. Like, I’ve been here in this space for too long. And I’m not doing it in a way that is actually fully feeding my soul. So like, I was also happy to let it go at that time. Yeah, you know, it was like that Marie Kondo moment, like I love you. You’ve served me now I’m letting you go.


HOST  33:02

Yeah, I hear that, you know, to, oh, it’s coming up. I told you I was gonna bring it up. Haha.



18 years he


HOST  33:14

audience you know, I talk about it every time. And I totally teased it to her and I didn’t tell her what it was. Okay. So I appreciate this idea of you becoming a new person, because I really do think that we go through like stages in our lives, where we’re like, different kinds of people, right. So like, the first round is zero to 18. Your your parents kid, you do what they want, they control pretty much what you’re doing. Your life is built around, you know, what you see? And it’s their life choices that form what’s going on with you. Right? Then 18 to 36 that’s your second round. to now be yourself. You are You are sent out in the world. All right, you’re an adult now figure it out. And you there’s trial and error for the next 18 years. Because, you know, there’s so many different kinds of things that you need to learn. Not only like how do I pay rent, what happens here? Where do I how do I you know, move to another place? Or like how do I make adult friends? What’s a job and how do I get health insurance? those basic things, but then there’s also like, probably multiple roommate situations, various ups and downs where like things work out with friends and not and you’re like dealing with being an adult and like, how do I emotionally deal with this stuff and everything, you know, 18 to 36 is like a huge chunk. But the idea so so then at 36 I think you become another person like you’ve lived through that, but like you’re 36 to 54 you it’s a different person because they You went through a lot, and you accomplished another 18 years. And you can, okay, I did it, I sort of graduated my first level of adulthood. And then you’re still there, right? It’s 36. Okay, keep going, No, no, keep going. And you’re like, who What do I do now? Right? Because like 18, to 36, there’s a lot of like, formative stuff that you can do take, go to school, take certain classes, start new things. But once you turn 36, and you’re older than that, people start like looking at you weird when you want to learn new things. And I totally think people should learn new things till the day that they die. But culturally, there’s like a, you know, we don’t really deal with what happens after your mid 30s. You know, it’s like, oh, and then the rest of your life. And I’m like, you know, what, if you roll through an 18 year cycles, you have like, three or two or three more to go. That’s a lot of things. That’s another, that’s a whole journey, right? So this idea that you let go of this fashion thing that you had held on to, not just from childhood, but almost all the way through, you’re sort of second cycle is, number one amazing that you maintained it, right? And that you kept interest in it,



because a lot of people totally change.


HOST  36:23

Like, they’re like, oh, he used to do sports, and now he’s a ballerina. And you’re like what, you know, so people, like fully make huge changes, as opposed to your situation where you’re like, Oh, I used to do fashion. And now I’m going to do like some another art adjacent situation. You know? What are your thoughts? Since I’ve presented my theories? What do you think about this?


Sheri  36:47

I would say like, I think I agree with the general concept, like the overall concept of we go through these phases. Yeah, I would say for me, that they’re definitely not that broad. I think they’re smaller, I would say maybe more like seven years. And I think there’s more of a, what I would call like a taffy pooling experience where there’s not clear delineation, like, like, so like when you talk about like the 18 to 36, figuring it out, like, I was the oldest child. And I was also the third parent in my household. So I was also like, super responsible, like, way more responsible than other kids in this weird way. So like the idea of like, not like, there was culture shock when I moved to Chicago, but there was absolutely not like me, not knowing how to navigate the world. Like, I definitely knew how to get an apartment, I definitely know how to get a job, I know how to pay bills, because like I was having a hand and that stuff for my own family like, like, Uber responsible, if anything too responsible, which kind of contradicts what I said about being an artist, but they still did go hand in hand. And I think at least for me, and I think we’re a lot of people in black families, there’s this also the sense of familial responsibility and obligation. So even as I was doing fashion, for myself, it was not entirely also for myself, it was also for, for the family, because it’s also like, I have to succeed on their behalf also, I have to succeed so that I can take care of my family who is struggling, and who has sacrificed so much for me, right. So like, there was a different and and if I let it go, then also like, maybe then their sacrifice was not worth it. Right. So I think for me that like, even within that time, like I was several different people living several different lives, artistically. You know, because he says, especially with something like fashion, like you go through artistic phases within that, right, so there’s like, there’s a fashion as a job, which is just like, you know, a lot of computer work, actually, it’s very little of the glamorous stuff that you see, which is also part of why I’m like, this isn’t what I thought it was going to be. But, um, you know, but then the outward expression of fashion, you know, it was my own to to be different, as often as I wanted, right? Until even within holding on to that fashion. There were still other things beginning, like I began improv far before I gave up fashion. So like they were so that’s like that Tapi pulling effect, where, you know, and even before I began improv, I was reconnecting with my writing. Right? So, so that it’s like, as one is ending one as beginning and so like, there’s not this clear delineation. But I would say it’s more like a seven year cycle versus an 18 year if I because I’ve been 19 different people from the time that I was like, you know, graduating at 18 leaving my parents house for the first time and being afraid to tell them, I have a boyfriend and he’s white. You know, all the ways Like 36, which was only a few years ago, I mean, even 230 or 225, I was like completely different people at all of those ages, and in varying different areas with a lot of my peers, because I was this kind of more responsible child who had to be responsible and, and I carried like, you know, a burden. But I think a lot of people do. I don’t think that’s unusual. But I definitely it was, even though there was this light hearted, like, yes, I’m, you know, chasing my art and doing these things. I was still like, I have to make this work. Right. Yeah. So yeah, it’s a different, it’s, I guess, it’s just a slightly different perspective. But I do agree with you with like, the idea that there’s these cycles. But I also, I don’t know, and this is also maybe different for black women. Because culturally, we start behind the idea of like, getting to like 36. And being like, life is over. It’s not a thing for us. For us. It’s actually life is beginning. Right, like now I have options and things that I couldn’t do when I was younger, I can do them. I have resources now. I have avenues now. So it’s like a, like, I hear it, like some of my other girlfriends who were, you know, we’re like, my life is over. I’m like, not mine. I’m actually like living right now. Like, this is amazing. Like, I don’t feel that pressure to be like, I have to stop doing new things. I’m like, No, I’m just starting to do things. Because like, you guys got to go to like, you know, the Bahamas when you were in high school. And like, that wasn’t something that I could do until many years later. So like,



wow, you know,


HOST  41:36

I’ve never been to the Bahamas now.


Sheri  41:39

But I’ve not actually been to the Bahamas, but I’ve been to the Cayman Islands a few times.


HOST  41:45

I am, I appreciate that the this idea that like, you know, you feel like, ready and more well prepared, I like that, I’m going to take that that’s gonna, that I’m going to accept that. And, and I appreciate I appreciate that. That’s something that people feel, because I feel like a lot of people who I talked to, are feeling differently, because, well, a lot of the people that I know, I’ve been doing theater, you know, in film for a long time. And you know, when you get to a certain age, people are like, Well, that’s it. You don’t look good anymore. And it’s real. And so


Sheri  42:28

it’s like, that’s totally real, like a gym is ageism is totally a thing. But it’s also like, and I can stage my own production and you can’t stop me. You know what I mean? Like, yeah, I don’t know, that’s just me. I think I’ve always had that kind of level of audacity of like, Oh, well, I do my own thing, like, you know, be a part of a fashion show, just cuz I want it right.


HOST  42:48

I mean, I’ve been producing my own stuff for my whole life, because people were like, not casting me and things. And I was like, Yeah, all right, well, I guess I’ll do this. I’ll guess I’ll make this on my own. So that’s definitely that’s definitely how it is. But no, I what I mean, is I just appreciate this perspective of like, now that you’re 30. So now that you’re over 36, like you have, you know, accrued enough lessons and you like, have enough knowledge now that like, maybe you’re gonna be alright, because you’ve, you’ve been through some stuff and like, now you can you can handle it. And I’m like, Oh, wow. I mean, like, sometimes I feel like, confident in my abilities to deal with insanity. Certainly, the last year or so has been pretty wild. And my, like, not going off the deep end. I was like, Oh, good job.



Good. Yeah.


HOST  43:43

But, but, you know, I like this idea of being like, yeah, this knowledge that I’m going to, that I accrued over this time is going to help me that’s much better way of looking at.


Sheri  43:57

And I think some of it is just like, it’s just coming. I think it’s like, a practical place. It’s just like, like, when I was younger, like, you know, going to college full time and working full time, and then going out on the weekends with my girlfriends and doing homework and doing all my chores alone. You know, like, like, that was so much. And I look back on that time. And I’m like, I could never do that today. But you know, when I was young, I had the interview, and I could just like grind it out, you know, but so, in some ways, getting older to me is like a huge blessing. Because I was talking about this a lot like the physical limitations of like a body that like if I stay up too late, and then the next morning, I’m like, I’m wrecked. You know, when I was younger, like, I remember going out like to bar coming, waking up the next morning and being like, I’m gonna go run 10 miles, right? Like, and then do all my errands and it’s fine. I could not do that now, but it’s also a blessing for me to be able to say, Oh, I listened to my body, and my body says rest and I’m going to And then when I come to my work, I’m doing it from this place of, you know, more relaxation and more groundedness. So like, like, I don’t know, I love getting older. And I think I just remember this old episode of like Oprah where it was like her and a bunch of like, old divas. And she was just like, turning 40 like you, you grow into your power. And then like, as I got to that age, I was like, she’s absolutely right. Like, my God, like, little age is an amazing time for women. Like, don’t, don’t be afraid of that lean into your power, lean into your power. Absolutely.


HOST  45:34

I’m looking forward until, till I get to the Golden Girls level.



I’m like, Oh, my God, I


HOST  45:39

think that’s gonna be a good time. You know,


Sheri  45:42

I’ll have no axe to give.


HOST  45:45

I’m just hoping, you know, because like, my mom kind of has a similar lifestyle to that in that she lives in condos alongside her other, you know, widowed friends. And so it’s like all these old ladies. Older,



not old, much.


HOST  46:04

older ladies, who are all hanging out together and they like go workout and do like water aerobics during the day. And then like, you know,



amazing. It’s,


HOST  46:13

it’s great. I mean, I mean, they’re totally there for each other, like, you know, like all the craziness that’s going on. I’m like, are you and your friends taking care of each other? You know, and she is of course, but it’s like, all this. It sounds like so much fun. You know, I’m like 70 sounds great.


Sheri  46:33

It’s almost like living back in a dorm again. We’re all hanging out together.


HOST  46:40

Yeah, right. Here we go. And and to take a feather out of your cap from earlier. Sherry, let’s get a 401k. So that later so I can move.


Sheri  46:50

Okay, yeah. And then I mean, after I cashed out that 401k I did not have actually, I don’t think I ever got one again, actually. So it was kind of the end of it. But it took me to where I needed to go.


HOST  47:00

I don’t even know if they exist anymore. It’s hard to know in the way that finances work.


Sheri  47:05

They do but get a Roth IRA IRA if you are an artist. Finding it now, no matter how young you are, you will your older self will appreciate it. Okay, good to know.


HOST  47:17

There is good solid Look at you. You said you weren’t good at math. But look at you. You’re giving solid accounting advice.


Sheri  47:24

Sherry Flanders improviser and financial advisors.


HOST  47:33

Add that to your resume, like immediately, like, I’m receiving your advice you’ve just done? Oh my god, I’m


Sheri  47:40

pretty sure the SEC is gonna come for me, they’re gonna be like that. As far as advertising, you’re not licensed?


HOST  47:45

To tell me to try something? I don’t know. I think you can tell me to try anything. If I do something, and then I try to sue you. I think that’s a problem, you know? Yeah. Oh, man. So hey, speaking of business, you mentioned that, you guys, you and your husband started a consulting business, what did you consult on?


Sheri  48:05

we consult on nonprofit and for profit businesses on how they should run, the better. We do a lot of different things. At the beginning, when we first started, I was rolling in my design experience, and my writing experience. So we’ve been doing a lot of branding marketing from my end. He’s somebody who has worked for over 20 years, in nonprofits as like executive directors and development directors, we did a fundraising grant writing that kind of stuff. And so early on, he was like, hey, you’re a good writer, I’m going to show you how to write a grant. Right? Because he was already like, you know, when you like, get married, and then your spouse of like, you’re gonna do all the things that I do now, right? Yes. It’s just a thing. You’re like, I didn’t know that was gonna happen. And so he would be working for various nonprofits, and I would be there helping volunteering. And I’m like, this is great. I love volunteering for good causes. And then one day, he was just like, you’re gonna learn how to write grants. And I started to do that. And it’s like, oh, yes, I’m good at it. And I started learning the ropes. And we talk shop as you do, and getting more and more involved in it. And now I also work in nonprofit consulting, and have my own little mini resume compared to so it’s great.


HOST  49:14

Huh? You mentioned also in year, something that you had said earlier that you around this time also go back into your writing is that the grant writing that got you reignited your love for writing?


Sheri  49:28

No, I’m actually this was prior to the grant writing. So like when we first got together after I graduated, or we got together right before I graduated, and he was working on a film script at the time. And I started helping him with it. And he was like, Oh, you’re a good writer. And I’m like, I know. And, and so he was in but we were both looking at the script. And we’re like, the script is supposed to be funny, but it is not as funny as we would like it to be. And he was like, Oh, you should we should take classes at the second city. And I had I’m in Chicago for a while, but I and I kind of and I knew what the second city like was, but it, you know, other than knowing like it’s a place that comedy happens. And I think I hadn’t seen like one show there. Like, I didn’t have really a frame of reference for it. I didn’t understand like, what it meant in terms of comedy, the comedy world like improv, like I had maybe been to, like I did like comedies, or show like, years ago, I went to go see one, you know, so like, I, I knew generally what improv was, but it was not really on my radar in any way. And so then we went to take these classes, and he took a writing class, and he’s an English major. So he immediately was like, I’m beyond this class, nevermind. But I took improv. And I was like, This is amazing. I’m having the time of my life. This is so fun. So I reconnected with, you know, my previous years of performance, and I was like, I had forgotten how much I love this. And I dragged him into the improv classes. And so then we were kind of off and running. But it was that the getting back into writing a screenplay that was kind of reignited writing for me, in a creative sense.


HOST  51:07

Oh, that’s really nice. I like that it was trying to help your husband. That’s really sweet. It’s like, it’s like you He made you learn how to write grants, but you helped him write a screenplay. Did you finish a screenplay?


Sheri  51:21

The funny thing is, yes, we there’s a box full of drafts in the garage. But we never went back to it. I like I sometimes I’m like, one day when I’m like, at, I’m going to finish and produce the screenplay. But we’ve written other things since then. But yeah, it was interesting. It Yeah. Yeah. It took me something right. Again,


HOST  51:38

you don’t have to finish it at all. Sometimes, writing projects are there just to get you through something like for sure.


Sheri  51:46

But I’m one of those people. It’s like, if you start if we start a movie, like it sucks, like, I have a hard time turning it off. I’m like, I have to watch it. Or if I’m reading a book, and I’m like, book sucks. I still feel like I have to finish.



Oh, no.



It’s just one of those weird things.


Sheri  52:07

Like always in the back of my mind. I have to finish it.


HOST  52:10

Now, I feel like I have to warn you. Don’t watch Bruce Willis movies if you’ve never heard of them, if you see it, and you’re like, wow, I mean, Bruce Willis. Isn’t this movie? It must be good. No, no, there is a handful of terrible Bruce Willis movies. And I’ve watched them all. Because I was like, cut Bruce. He’s great at stuff. And then we held on to both way to turn this off now. And I was like, I swear Bruce is gonna do something great soon. So I just wanted to warn you, so that in case you guys are gonna watch a movie later, you’re not like, you know what, it’d be fun. I’ve never heard of this random, clearly straight to video Bruce Willis movie. Look, it has another random famous person in it. No.


Sheri  53:04

Like those movies, though. That’s just who we are. We we actually now do a lot of theater reviews. And we just got finished covering Sundance. And yeah, most of them were amazing. And you know, and then there was like one or two. Pretend like we didn’t see it.


HOST  53:23

Yeah, I saw that you do a lot of reviews about different kinds of thing. You did a review on like an improv show. And then you know, a film. How did you get into that? Like, how did you so at this point in your journey, you know, as you’ve told me, you know, you’ve reignited your love for writing through the second city. And that’s great. I’m so glad for that. That’s a wonderful


Sheri  53:45

thing. And I teach there What? Great random.


HOST  53:51

No, that’s wonderful. I love that. And you still you still teach there right now, huh? Yeah, I


Sheri  53:57

teach in the eighth re program and in the music improv program. So mostly the the newbies, I love teaching the newbies and being like, Yes, hello. improv is fun. You know, the same way that I kind of came into it. It’s a good time.


HOST  54:10

Oh, yeah, I really, I teach level one and I prefer my level ones. Tell me you’ve never heard improv. I want to talk about it.


Sheri  54:18

Oh, yeah. Cuz you can just like blow their mind. Like, every two seconds. It’s so good. They’re not jaded yet.


HOST  54:24

Well, I also like, I also just really like creating a foundation for people and so that they can, they can enjoy it on long term. You know, yeah, a lot of times people are looking to take improv for like, the short bursts of like, you know, applause and laughter and that’s what they want. And that’s what fills their cup. But I think there’s so much more to it, and it’s not. Yes, it’s great when they laugh. Yes. It’s great when the audience is with you, but like the whole experience of you and your teammates. Unlike what that is just not only as a team building, like, we’re all bonded together, we have this experience together kind of thing. But also, how do you then take these skills and use them in the real world? So I’m always talking about stuff like that. And like how I tried to debunk this idea that you have to in order to be good at improv, you need to be automatically funny. And you need to have these series of skills and I was like, No, I improv is like breathing. Everyone can do it. It’s really just like, how’s it going? Like, some people are breathing great. And you’re like, are you alright? And they’re like, yeah, you know, it’s, and that’s where they are, you know, some people need assistance to do such a thing. But you have to, you know, figure out how to do the path and, and then connect with your scene partners. And just, like, learn them, and like, if you’re gonna work with somebody know them, what are they like, what do they want? What are they? What is their? What do they always offer? Like, pay attention? And then it’ll help you? Because then you’re like, well, Tom loves setting it. You know, the location in a fast food restaurant, like every time.



Yeah, like,


HOST  56:18

let’s just do it for him. Who we ought we walked on stage. And you’re like Mickey D’s man. I love it. And he’s like, yeah, like, That’s his jam. Whatever it is. Yeah,



I don’t get it.


HOST  56:28

Makes it easier. He feels cool. And then he’s Eddie’s and we can chat with you. Yeah, I love Oh, my gosh, I love level one. It’s super fast. Yeah, and it’s really nice. I had I teach eight year olds to and they sometimes blow my mind with little like truth bombs about like, it’s so fun when your imagination goes. And I was like, it is fun. Like, I’m so glad you ladies are having a good time. Yeah, my little eight year old, a bunch of ladies love it.


Sheri  56:58

They’re gonna be so funny and amazing when they grow up. And I’m going to be like, I love it. I would tell my students, I’m like, one day, I’m going to be like, I know you win. And they laugh. But no, it’s true. I’m going to be 80 years old. And I’m going to see when I come TV. But no, I always tell my young students because I remember, like an experience that I had. I used to perform at a theater in Miami called just the funny. And it was a really great few years when we were down there because in Chicago, it’s a really competitive scene, like I got into just for fun, but a lot of people come here like because they’re like, I don’t wanna be on SNL or whatever. And so it’s a different audience. And it’s a lot of times your audience here is like other improvisers, were laughing for different reasons than an actual non improv audience would write. So it’s like, oh, you messed up. I’m like, okay, that’s weird, whatever. But in Miami, it’s like a very sincere like real audience not because it’s only so much improv, and so the audiences are just anyone else. And And so after our shows, we did this had this ritual, where the audience is leaving through the lobby, and we would all come from backstage and kind of like, be like, thanks for the show, or thanks for coming to our show sort of thing, right? And we could get the feeling of like how you did based upon, you know, the crowd’s reaction, if they were like, hey, are great, Oh, my gosh, let me take a selfie with you. Or if they’re, like, not making eye contact with you, right. I remember one particular night, and what’s really taught me so much, which was, we had this audience that was just wide, like, and like, we were on stage. And we felt like we were in the zone, we felt like we were killing it. And the audience was just very much like ball flat, ball flat. And we were just stunned. And we were like, well, bombing bombing, but I feel like we’re doing good. And then afterwards, you know, we’re like, and they’re like, Oh, my God, you guys were so good. We’re so amazing. And I realized, like, audiences Express express their pleasure in different ways, right? It’s not always like, loud laughter. Sometimes audiences are quiet because they’re intensely watching. Because they’re just in it so much. Sometimes they’re holding their breath, because they’re like, this is thrilling. And they’re different types of laughs sometimes, they’re laughing with you. Sometimes they’re laughing at you. Sometimes, you know, so I always tell my students like, not every laugh is the same. And don’t place your worth on the lap. For the audience response, right? Just be in the work, be in the work. Yes, you can play with the audience and, and play off that energy. But be in that, you know, be in the play with your fellow performers. Like that is the most important thing. Just enjoy it.





HOST  59:52

Man, what an interesting choice you made when you were in Chicago, that second city was the place that you ended up


Sheri  1:00:00

Yeah, I was just very


HOST  1:00:02

just so many in like that that’s the location. Tell me about the, the way that their style of you know, like, writing and improv into writing affects your current writing style.


Sheri  1:00:20

Um, I would I think, me like, you know, like I, I, I will say that the good thing about having an artistic life before coming to improv is that I understand my creative process and how I get to my place of creativity, how my writing works, things like that. So I wasn’t coming to it being like, I’m figuring out creativity for the first time. Yes, there were different mechanics. Yes, there was a learning curve, obviously, I was not like, really an improviser, right off the bat or anything. But I was able to bring my like, you know, my own creative vision to it. And so when I learned about writing, it wasn’t that it like dramatically. or excuse me, writing for sketch, it wasn’t that it dramatically changed my style, necessarily. But I learned like, new concepts and applied it to what I was already doing. So like, especially like editing, I mean, just a basic thing. I’m a verbose person, I know that about myself. But, you know, the ability to be able to find more succinct edits, to be more succinct with my words. That was probably the biggest thing that I got from it, you know, to find those punctuation moments. That was probably the biggest influence on my writing. Oh, yeah. And we also want to be able to bring in that love that he went, I want it to, because I think when you come to writing, as a writer, you know, it’s more serious, heavy grounded. And so understanding the power of validity, even in a highly emotional charged moment. You know, that is, that is a thing. Yeah,


HOST  1:01:53

yeah, absolutely. When right now you do a lot of, you know, writing your you improv, and we ever do films and stuff. How did you get that kind of job like, so it makes sense, you know, you’re writing on your own. You’re working on screenplays, you get involved with this theatrical form. improv, that’s fun. There’s a little bit of writing in there, but it’s very specific. And then you also learn grant writing. But now you’re writing for like magazines and articles and stuff, like how do you get into that world? That’s a different kind of thing. Certainly, for writers who might be listening like, Hey, I have written sketches, but how do I possibly write for a magazine?


Sheri  1:02:36

Yeah, well, it was definitely accidental and organic, like a lot of my career choices. Um, I like I said, I already was a person who was very confident my writing skills like, you know, full stop, I was always like the that student in classes where teachers were like, You’re such a great writer, like, even in fashion design school at the boat, they were like, do an extra project. And so something or write a 10 page paper, I’m like, I’m writing a 10 favorite page paper, you know, should have been assigned, but you know, then pick up on it. So I’m going through and propagated am taking classes and city IO doing shows all the things. And there were some local kerfuffles. in journalism, basically, this kind of the same thing kept happening repeatedly, which was, people in theater, people in comedy would do a show and a critic, and there are several very prominent white critics in Chicago, would write a review of it, and they would not really get certain cultural references, they’d make kind of really ignorant remarks. And the entire community would get really mad and try to get through to them, they wouldn’t hear it. They’d be like, we don’t have to listen to you sort of things like it was bad scene. And one particular reviewer reviewed a theater show called a Passover that was at Steppenwolf, and, and he said something super insensitive. And community was like, that’s it. We’re not giving this all like a whole lot of theater for like, we’re not giving to this particular critic. free tickets to see any theater shows anymore. It was national news, but huge thing. And in response to that, in organization, the Chicago theater accountability, missions, AIPAC, I’m not quite sure what that acronym is. put out a call for people who wanted to try their hand at writing, right? And so I was like, Okay, I’m gonna write, I think I can do this. And I tried it. And I wrote a review. And it was good. And someone who had from a paper called very resolved one of my friends who had a site called Chicago and musical theater had reviewed. One of his critics had reviewed my musical earlier, and he was like, I can I see that you can write Would you be interested in writing for me? And I’m like, well, Yes, I would. And then I started writing for him. And then several other publications asked me to also write freelance For them, because I saw that I was doing this. And everybody at that time was like looking for new voices, because there were a lot of stale voices out there. And then kind of one thing led to another. And eventually, I applied for a grant with Sundance, and I joined was part of their press inclusion initiatives. And I was invited to cover Sundance. And that was kind of like my entree into covering film. And it’s been so much fun, because especially in so when we talk about like, those different phases of life, this was also a phase for me who I had come to the point now in my improv experience, where I was like, have been doing this for a while, I’m feeling like, you know, I wouldn’t say, expert, but like, I’m solid, like, I know the basics, I, you know, put up in putting up shows like I know my way around this world. And to the point where maybe I’m starting to get kind of bored and stale of certain things, doing them over and over again. And then I was invited, to have an eye to look at other people’s creativity is even out, even outside of the world of improv and more into theater, and then be inspired by these longer format pieces, and then have that feed of my own creative writing. So it became kind of this wonderful feedback loop where I’m like, Yes, here’s a new way of seeing the world, here’s a new way of engaging with art. And it’s just been wonderful.


HOST  1:06:23

Man, that sounds amazing. I love that your is the cycles that we’ve talked about, or, you know, you’re you’re always doing writing just in with different ways, you know, you’re reinventing the way of writing and finding a new spot where you can be the most helpful. And then also, like, Where am I needed? Your story, by the way makes me think, again, we’re chatting, how funny it is like the world of having the internet and previous, when you were like, yeah, and then one thing led to another, and I was writing for a few magazines. And I was like, I don’t think that’s a thing that happens now. But like, I’m so glad that it worked out for you in this moment. And that the world was such at the time when people were like, Well, let me send an email to this person who’s cool and see if they want to write stuff like that sounds great. I don’t know exactly how that


Sheri  1:07:17

very special Chicago thing. Like, yeah, that was a very, Chicago has always been and that’s been a thing that I think what part of what makes me love it so much is that it’s a very chill town. And people are accessible here in a way that I don’t think that they are necessarily in other cities. Like, if you want to talk to somebody, like you can get through to them pretty easily. You know, it’s just, I don’t know, it’s just like casualness of the Midwest, I think it’s just a thing, where it’s like, I felt like if I went to New York, or if I went to LA, you know, there would be rooms that I would never be able to walk into people that I wouldn’t ever be able to talk to, but you know, even like local celebrities here is like, you can say hey to them, and have a chat with them after a show and they’re gonna be pretty chill. And, you know, and if you’re that kind of person, and I’m not I’m too shy, usually, I’m not gonna but you know, I know plenty of people who are like, yes. And then I had a drink with this person at the bar. And we had a long conversation, you know, like, let’s just, people are just chill. And there was just this organic sense of like, Hey, you know, not saying that everything’s perfect. But we obviously you have our problems if you’ve been reading the news. But um, yeah, I think it’s just why things happen easier and organically in some ways.


HOST  1:08:28

That’s so nice. That sounds like such a small town feel in a big city. That’s really



yeah. I like that, huh?


HOST  1:08:38

So I want to ask you as a means of wrapping up our conversation you have been doing well, by the way,



it’s been great.


HOST  1:08:46

I wanted to ask you what it is that right now is igniting your creative fire, like what? What’s the project or the idea? And, you know, no spoilers for anything made out or whatever. But, you know, what’s the what’s the thing that’s keeping you up at night thinking about, you know, oh, I want to do this, or Oh, I have this project that I’m working on? Or, oh, we’re building this thing. What’s the thing that’s, you know, in you in you right now, so excited? Well,


Sheri  1:09:18

I have a lot of things because I’m, I’m always been the person who’s had like my hand and a lot of different talks. Like I did, one thing that I’m doing is I’ve started a nonprofit theater and moving very slow with it. So don’t expect to see anything, anytime soon. And that’s on purpose. Because a we’re in the middle of a pandemic. And so, guys, please, if you’re listening to this, please don’t run back to the stage because we haven’t all had our vaccine data Take your time. But also, just because this time is so precious, like we’ll never have this kind of time again, where we’re all at home in this way. And the world is on pause and so on. As an artist, you know, like I said, I’ve been looking back to those years of my life where it was like constant hustle working full time going to school full time, you know, you know, the nine to five, five to nine, to be able to pause is just so rich and so beautiful. And so like I’m taking this time with anything that I do artistically. And just like, let me just look at it. And let me just let it, let me simmer in it. And so that’s really where I am. Like, I’m in a beautiful, almost like, I think of what my favorite place in the world is in Paris. And it’s this museum called the Orangery, and it has Monet’s water lilies, the big canvases, and they’re on this park around a wall in this in the circular building, and is gorgeous. And so you look at it, and you have the sensation, you sit there of being in like a boat, on a serene pond, sitting amongst the water lilies. And that’s where I am creatively, creatively right now, you know, and I’m, like, hoping that on the other side of this pandemic, we will have made the world a better place, and we will continue to make it a better place, as well, like looking to see what can bloom Wow.


HOST  1:11:24

It’s very good, this idea of reflecting. And, you know, since we have these moments, so many of us who have packed our schedules, with 1000 different projects, and you know, when you finish one, you quickly grab another one, because you’re like, well, I can’t have any time off. Well, that would be crazy. People would think, wow, what you doing? And, yeah, I mean, it’s, there is something really great about being able to take the time to decide what kind of projects you want to do, even based on what we’ve talked about the different things that you know, the different artistic things that excite you in the moment, like, you know, sometimes it’s writing and sometimes it’s, you know, creating clothing, and sometimes it’s performing on stage or even teaching, you know, or consulting businesses. There’s something artful about that.


Sheri  1:12:18

Didn’t even talk about music. And that’s a whole nother thing with music improv.



Oh, yeah,


Sheri  1:12:22

it’s all connected. Like I, whenever people are like, Oh, I don’t like this kind of art. I’m like, why not? It’s all connected. It’s all beautiful. I just let it it all flows into one each other there are they’re not these delineations that I see. Anyway.


HOST  1:12:36

Yeah, plus, I mean, only if you get to a certain point almost to bring back the idea of like, going professional with some things like, yeah, if you become a professional lighting designer, sure. They’re gonna want you to do the lights. Like, that’s gonna be a thing. They’re gonna want to consistently see you’re hanging out there, right?



But yeah,


HOST  1:12:57

but certain, but if you stay within a certain level, I mean, I’m pretty sure Brad Pitt’s not like Hey, guys, listen, I’d really like to learn how to be a grip. Like, everyone’s like, okay, Brad, he can’t like he That’s impossible. You know what I mean? Like?


Sheri  1:13:12

Did you watch the, you know, like the last dance or Michael Jordan, which was, I have feelings on that documentary. But that’s a conversation for another time. But I haven’t, you know, he’s somebody who was like, I’m the best basketball player and I’m gonna stop and I want to go play baseball. You can do it. Oh, yeah. You know? Yeah. I mean, like, I think people like we put limits on ourselves. We put limits on other people. But there’s absolutely nothing that says that. We can’t do it.


HOST  1:13:40

Absolutely. And what a great analog to sports. That is exactly right. Especially the poor kids who have the fortune slash misfortune of becoming pro early in their lives. It’s like, oh, sweetheart, you’re gonna turn 27 and need to find a new job. Like, yeah, that’s crazy. But yeah, they are, right. So why not have open your mind to the malleability of like, hey, what what are other things that you’re interested in while you are doing this awesome job. And you are spending time doing like really focused on this thing that you worked hard on? I mean, enjoy that enjoy it. But also think like, what are other things that I like to do? I mean, yeah, and I feel like that’s, that’s like it for everybody. And I say this even now to about people who are like, Oh, well, I lost my job. And then between stuff, I don’t know what to do. They don’t have boba. I’m like write down every skill you think you have write down what skills you would need to have the jobs you’ve already had. And then those are skills you have and then see if maybe you can’t turn that into something different, because most jobs are similar in the what they’re looking for. They want you to work hard. They want you to be able to do it on your own without them having to tell you about it. And you have to do it efficiently within a deadline. Great, I’m pretty sure any job you’ve ever had had those rules, right? And you just have to reform what it is that you’re looking to do or open your mind to the fact that like, you know, I imagine if, if when you went to school for fashion design, someone was like, Hey, you know what you’re going to be good at someday grant writing, you’d be like, Okay, great, whatever, you know, but you don’t think of the fact that you even already have the skills at that point, to know how to do it. But it wasn’t until somebody inspired it in your brain and said, like, you know what, you can do it, and you’re like, I can do it. And then, you know, you can move forward. So I really, I really think that that’s a great piece of advice, for sure.


Sheri  1:15:46

Yeah. And I would also say, like, especially and I and this is like my love letter to people who are between jobs, because like that period, like I’ve lost over so much, but that period of like, transitioning out of one career into another was very difficult. But one thing that helped me and I gift this to others who are going through that experience, was was grounding myself in the fact that I was enough without Korea, right? Because I was somebody who was always grounded in like you, you know, you have to be responsible, you have to take care of all these things. And I remember I speaking to a good friend of mine, and I was like, you know, kind of lost without a job. And she was just like, whatever. You’re a housewife. I’m like, I don’t have any kids. And she was like, you’re a homemaker. cracks me up to this day. But what it meant what it triggered in my mind was, I am a fully rounded human being without a career. And I have like so many, you know, we could do a whole nother podcast about my feelings about the economics of in improv and all of those things. I have very strong feelings on that. And I think there’s some bad things about our industry that makes it very exploitative. And so like, I have also feelings about the idea of like art only for art, because sometimes people should get paid. But, but you are enough without a career, and without even artistic practice. And that’s okay. Yeah,


HOST  1:17:12

you are enough. I like that. That seems like a good spot to and and some solid advice to the people that are listening. Thank you, Sherry, so much for being on the podcast. You have been a joy.


Sheri  1:17:26

Thank you. Anyway, you are also a joy in one day after the pandemic, hence, I hope to come to Austin and hang out with you.



Oh, absolutely. I’d


HOST  1:17:34

love to see Chicago as well. I don’t think I’ve been there since.






maybe 97 That’s a long time ago.


Sheri  1:17:45

I’m bored of it. Come on by Yeah,


HOST  1:17:48

absolutely. At this point I as soon as they let me travel, I’m going to be traveling as much as I can


Sheri  1:17:57

find an improv jam. We’ll do it we’ll get on stage



Awesome. Awesome.


HOST  1:18:11

Thanks for listening to yes but why podcast? Check out all our episodes on Yes, but why podcast calm or check out all the content on our network at Universal at HC Universal Network calm

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