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Whether you're at the top or striving to get there, you may have noticed that there's one thing many people do not talk about, the mess and the difficulty behind success. I'm Maryam Banakaram, host of a podcast called the Messy Parts, where I interview people about the mess, the twists, the turns and the pivots that have shaped their extraordinary careers. I'm excited to bring you this hark list with insightful moments and advice featuring Negeen Fersad, a comedian, Katie Storino, a beauty entrepreneur and amazing, amazing restaurateur named Vicky Freeman, and so many more. Before Nagin Frassad became a comedian, she was that perfect student whose parents were proud of her and wanted her to have a prestigious and safe career. You can imagine that deciding to be a comedian was not what her parents had in the cards, but her father told her that he was going to support her in her work in comedy. I was a perfect student. You know, I, I was, I got perfect grades. I did everything right. So in my mind, it was just really a side thing that I was doing, like theater and whatever. And the first time I got on stage, I was in a musical called Once Upon a Mattress. And I was not kitchen wench number one or kitchen wench number two, but I was kitchen wench number three. Some might say the soul of the kitchen wench is. I don't know who would say that, but some would. And I got on stage, did a thing, it was like a silly physical comedy or whatever, and I got huge laughs. And I was like, this is an interesting feeling, you know what I mean? Because it's just like, oh, everybody's laughing and I can say anything right now. And they would listen. And that was a really interesting realization. And it just sort of like built from there that you make people laugh and then they listen to you. And when did you start leaning into sort of the more social justice pieces of the comedy? You know, I was always interested in that stuff, right. Because I was always interested in politics. I was always interested in how government works. I always thought, what's great about being American is that you're building towards something better all the time. And once I left my job working for the city to go full time into comedy, you know, one of my first jobs was as a writer on this Comedy Central, like, web. No, mtv. Mtv Web series. Wow. I don't remember my first job, but I think it was mtv. That's right, it was mtv. It was sort of like a little, little mini late night type show. We were writing a lot of monologue jokes, a lot of sketches and stuff like that. And I remember just being like, okay, I need to write, like, three jokes about Justin Bieber's abs by one o', clock, you know, and, like, that pressure of, like, writing stuff that doesn't matter, you know what I mean? That it was a job where I was, like, under the gun, but to write stuff that was so silly, so dumb, you know what I mean? Like, and after a while of, of living like that, I was like, oh, I do need to do things that are more important. At least do something from my own tiny, tiny, tiny corner of the world that might, like, change hearts and minds, you know? We still didn't talk about your parents. And. Yeah, when you told them that, oh, you know, forget stability, I'm going into the land of comedy. Yeah, I could tell they were disappointed because I literally eavesdrop on their phone calls. And I was in the other room one day when I was visiting for Christmas or something, and my mom was on the phone with a friend of hers, and she was like, we are disappointed. You know what I mean? Like, she literally said it. And the way they would always say to their friends, like, if we went to a party or something, this is our daughter. She's a comedian, but she has masters from Colombia. They always talked about the degrees, right, as a way of, like, saving face that our daughter went into this ridiculous field where we don't know if she's ever going to earn money. And then always said to me, oh, but you could always fall back on policy or whatever. You could go back and work for the government. And I like, it's been five years, it's been six years, it's been seven. I was like, who would even hire me for a government job anymore? Like, I'm so obviously a comedian, you know? And so they were, you know, disappointed for a long time. And then one day, I mean, this was like maybe five or six years in, I mean, I was still living on beans, like, making very little money. And I asked my, my parents if they would help me pay for a plane ticket to go home for Christmas. And I was like, I'm really sorry. It's going to get better, I promise, you know? And he was just like, no, don't be sorry. You're like a scientist. And I was like, what? He's like, well, you know, scientists, they have to work for years before they, they have a discovery. And sometimes they don't even see their discovery in their own lifetime, but they're Working towards it. And that's what you're doing, you're building a career as an artist and it's like being a scientist. And I was like, oh, okay, thanks. I didn't realize you saw it that way. I do hope I see some of the fruits of my labor before I die just for, just to. Let's just get that out there. But it was interesting because, you know, I come from parents who didn't get to have the choices I had, right? They had to just make utilitarian choices. And my dad wanted to be an artist. And when he was in Iran, he won a scholarship to go to an art school in Italy. And his dad was like, no, we don't. That's not real. And so you have to figure out something else. So he chose surgery, which was a different form of art, A different form of art, working with your hands, craft based or whatever. So it kind of made sense. And my mom wanted to be an opera singer and she studied opera. But again, it was like that was an inappropriate career path for a wife. So I think in many ways I've sort of fulfilling the things that my parents had secretly always wanted for themselves. As a successful actress whose credits include Mean Girls, SNL and Elphaba on Broadway, Ana Gasteyer knows a thing or two about following your dreams, despite what others have to say. Gastire has a powerful conversation with me about how you make your aspirations, your identity. So because we are both women who've juggled. What is that like? Like, what advice would you have for young women who are coming up? I mean, not, not, not the kind of advice that says don't do this because guess what? If you love what you do, you're going to go do it. What little tips should we give them? I mean, I think your first thing you said is the right is not, not do it because what's gonna feed you? And if you're not gonna have time enough in your day to have, you're gonna be busy no matter what you do. So you may as well have it be something that you love, right? So that when you do come home for your 15 minutes with your children, they say you're a lot nicer when you're doing musical theater. I definitely, I'm nicer when I come home if I have a job I like. That's exactly right. Find something about it, you know, it doesn't have to be whatever those years ago I did that Myers Briggs or whatever, you know, to try to determine what kind of jobs. And again, what does that mean, do you like having a community? Do you like working remotely? Do you. Do you get your energy from other people? Do you get your energy, you know, from ideating by yourself? Like, those are good things to know about yourself. I think out of the gate. You know, one thing I've noticed, because I was just on a panel, and a woman came up to me and said she wanted to be more of a writer. Not theater writer, you know, film writer. She just wanted to write more, and she wanted to know how to transition into a writing job. And I was like, why don't you just start a substack? I mean, I just think there's so many more opportunities for this generation. Like, in our era, you had to get into sitcom, you had to get into shows. Right now, people get famous from doing tiktoks or substacks. Don't you have to tell yourself, though? I mean, we both have daughters, right? We both have daughters with ambitions. And I. I. Probably the thing I carpet her the most is like, who are you waiting for to tell you that you're allowed to do this? You have to go do it. You just. There's no. And does she. I think every. I think she's getting there. I think I had to. There was a day at which I had to say to someone at a party, and these are all, like, the tricks, right? I mean, acting is the funniest thing, because most of the time you're not doing it. It's what you want to do. So when someone at a party says, what do you do for a living? So quick for you to be like, I'm a temp, you know, or whatever the thing is. But actually, just stating the truth, I'm. I'm an actress, you know, I. I want to work as an actress. I'm developing a show for myself right now. When I learned that trick, when people were like, what are you working on right now? Cause that's all anyone ever asks a performer. And you're like, well, I'm writing this, and I have this idea, and I have this. You actually have all of that agency. And when you can kind of state it to somebody, you know, I love. You know, I love running. I train for marathons. Probably my happy thing that I do, or whatever the thing is, you know? So it's about believing yourself and also being willing to say it out loud with confidence. Right? Yeah. You have to be the first advocate, the very first one, not waiting for someone outside you to tell you what you're good at or what you are allowed to do. It's really like the thing your aspiration is your identity. It's the thing that you want to be that gets you out of bed every morning. Yeah. But I'm willing to embarrass myself, like, okay, I'm gonna do a podcast. And if it doesn't work out like it does, I mean, it doesn't mean I'm not terrified or that I have no fear. Right. But I'm willing to go for it and put myself out there. I mean, I was not a cool kid, and I seem to not have been too worried about that. That's a great one. Self doubt weighs on all of us when we're trying to pursue success. Katie Storino, founder of the beauty brand megababe, has a simple secret to how she breaks the through. Now Toast takes off, and where do you come into the picture? Because all of a sudden, then Toast moves to the side and you become this. Yes, we were on a photo shoot for Nars beauty brand. Yeah. For Toast. We were doing, like, shots of, like, blush on her fur, like, super cute. And the editors who are working on it, I pitched myself because, you know, PR mindset. And I just. I was like, you know what? They should do a story on me. Okay. I. I love this. I think it's the fear of rejection, maybe that people think, what's the worst that's going to happen? They're going to say, no, I don't know. I'll ask anyone. Any, like, anything. I don't know. That's why I'm a very good wingman or wing girl or whatever. Right? Because you know what? I have no. No qualms. You want to meet somebody, I'm your person. Let's go. But people get scared of us when they're. When we're their wing people because we don't care. We're like, what's up? You think that guy's cute? I know I'm not good at it for myself, but for you, I don't really know you can do anything. Like, I'm like, who do we know who could make that mov. That I'm the same way. Okay. Yeah. So then I said, you should do a story on me because there's just no coverage of, like, curvy girls in fashion right now. I think the year was 2014. And they're like, okay, let's do a story on you. It was for Man Repeller. And I think the. The thing that happened there is my brain broke open when I saw the comments from women saying, what they mean. No, they were the opposite. They were like, I've never seen my body on a fashion blog again. It's 2014, so it's like, oh, so here's your next sign. Yes. They're just like, I, I, I, I love, like, opening up this page and being able to see myself. Like, wow, these shopping tips are so great. So I feel like that was a big sign for me. Okay, so you. The opportunity shows up. Yeah. In the sense that you see the comments and they're positive. I'm like, this is why love representation matters, Right? Yes. And so. Okay, so you pivot to thinking. So I was like, I really was deeply uncomfortable with being in front of the camera. You know, I'm in pr and behind the scenes, I'm doing dog stuff. I can put everything on toast. And now it's time for me to get in front of the camera. And that was so hard. But you pitched yourself. I know, but I'm just pointing it out. I know it. But, like, I mean, that first photo shoot, I was near tears, just, like, so embarrassed for. And yet you pitched yourself. I'm just pointing it out. I put myself there, but I was so nervous. And so it happens. There's amazing comments. And what happens to you? I had breakfast with the editor at Glamour, Sophia Chobbit, at the time, and she said, I don't think you're going to be a publicist in a year. I think you're going to be doing this full time. And. And I was like, okay. Like, let's see. I remember her saying that to me, and then that. And then as soon as I put it up online, the 12 style, because I had fluctuated, maybe a size 12, 14, 12 ish already exist or. Nope. So I started the 12 ish style. It was a blog. Yeah. My other friend was like, just start an Instagram, start a blog. Just do it. So I just did it and it took off because we needed someone in the space who was there to, like, help the big girls get dressed. So representation matters. You dream big and you just go for it. Yes. In the face of fear. Oh, yes. Yeah, I am scared. But, like, you just go, but so what? How do you have the ability to put that fear aside? I think I don't. I think fear is, is less strong than regret. And I don't want to regret anything. I don't want to leave an opportunity on the table because I got nervous. So even though you get anxious, you get nervous, you get fearful. You have a way. Yeah. And. But what is the Way, like, do you meditate? Do you go for a jog? Like, do you have a trick? Is there like a CBT trick? No, I just go. I just do it. You just go, Just do it, yeah. Before Vicki Freeman was the successful force behind restaurants we love in New York City, from Rosies to Vicks to Chouquette, she was the young woman who looked up at the sky when she needed an opportunity. And I mean that literally. She told me this incredible story of one day looking to the universe for the big break. And guess what? It showed up. So what happened really was in 1992, I want to say I was working in a restaurant called the Rose Cafe, which was the first restaurant I really worked in that was a great restaurant with a great chef and a pastry chef and all this kind of stuff. I mean, I always loved working in restaurants, but I really loved working in this one. So I was working in this restaurant. The restaurant closed pretty quickly without a whole lot of notice. I broke up with my 10 year boyfriend, and I was just sitting there going, I have nothing. I sat in my kitchen of my soho apartment that I shared with my brother. And I just remember sitting in the kitchen and looking to this guy and saying, okay, I'm open. Like, what is it? I still. Here I am. This is kind of like your Oprah moment. It was. I hate to say it because it wasn't even that I was particularly spiritual then, or it was all God. It was just something. It was coming back into reality. And on top of it, the guy I was seeing before I left was sleeping with my best friend. Okay, good drama, good drama. But I just sat there and said, okay, I'm not any further ahead. Right? Like, I still don't know what I want to do. How old were you? 31. So stressful. Very stressful. Because. So I come from a family of achievers. And I think that was also part of the problem because nobody in my family, as much as they're all food obsessed, all loved restaurants. You did not go in the restaurant business. Okay? We're in Soho. In the apartment you're sharing with your brother, you're looking up at the sky and you're saying, I'm open. And what happens? I am not kidding you. Later that day, I got a call from a friend. He owned a building on Broome street, and he said, as one does. As one does. And he's like, I have this coffee bar in this building that was owned by Suzanne Vega, which I don't know if anyone knows anymore. Of course she went to partner Tom's doctor. Oh, okay. So she owned this coffee bar in a half underground space on Broome street in Soho, on this nondescript block. And he was like, do you wanna do a coffee bar with me? And I said, yes, because why not? Why not? Nothing else coming in. I had to assume this meant something. That this call from the very next day, out of the blue, when I still had no plan, and now I was stressing. I'm seeing many of our listeners looking up at the sky, saying, I'm open. What's coming not very long into it, he said, you know what? How about we do a restaurant? We're never really gonna make any money. Not that he particularly needed the money from either of those things. And really, again, I'm not sure what made me say yes. Cause I really wasn't ready, which we'll get into. But I said, yeah, let's open a restaurant. I had worked in restaurants for all of my adult life at that time, and that's really how all of this started. And then we opened a restaurant called Vicks. And. And that was, to this day, one of the craziest experiences I've ever had. Because it was, like I said, halfway underground. It just hit something right away. I mean, there was limos down the block. It was just the craziest experience I've ever had. And it was filled to the brim with movie stars, models. I mean, I was getting calls like Julie Roberts and Meg Ryan. Want to come in? Da da da da, da da da da. But here's the thing. I really wasn't ready. And I didn't have the business background. I didn't have the back of the house financial background. I knew how to make a great restaurant. It was a great restaurant. And what was your partner doing, the one who'd made the phone call to you? Oh, he had nothing to do with it. He was just the backer. I mean, he lived in the building. I saw him. And he really didn't want to have anything to do with that. So you had to do all of it. Front of the house, back of the house. The business side. I see. So I thought, this restaurant business thing is easy, and I'm so cool, and look who's calling me. I mean, I wasn't 100% there, but there was a part of me that was, like, believed it, you know? And I think I got pretty heady about the whole thing, because every day it was unbelievable. It really was like. It was just a crazy experience. Irina Novalecky was an ambitious Young woman who made her own way into the world of finance. And then after she accomplished that, she had an epiphany. She didn't want to become her bosses. She told me about this breakthrough and how that led her to leave that world and actually take on not her first, but her second CEO role at Hootsuite. And so from there you go to Apollo, like pinnacle of the business. What made you make that transition? So at the time, the thing to do was to go to private equity. And there were three of the top private equity firms to go to. And Apollo was one of them. And for me, Apollo had this really unique differentiators. They were known as kind of the more hard working of the shops, but they had this culture of if you work hard, you get promoted. And it wasn't a drinking, let's go out culture. And coming in as the only female, I couldn't compete in a let's go drinks kind of environment. That wasn't going to be where my skill set was going to be maximized. And they just, I think you could maybe have figured it out, but I don't think so unless it's water. I am a lightweight and it just doesn't work for me. But they just worked hard and I thought, okay, that's an equalizer. I can work hard. You're like, I know, working hard. Yeah, I can do that. And I can sponge up what I need to. And so I got there and they're very good at what they do. They're the smartest at what they do. I learned a ton. And I also learned I'm not as smart as what it takes to do that or it wasn't my passion. And I somehow got, I don't know, really. I think you probably are smart. Like maybe it wasn't your passion, it wasn't my passion. And maybe the passion thing is really important because I was passionate about being successful in what I was doing, right? So I wanted to do good work because the money was important to me. Getting the learning was important to me. The career trajectory that Apollo and the aftermath offered to me was important, but the work itself wasn't really exciting to me. And I remember looking at some of my peers and they loved it, loved it. And I remember sitting there being like, I can't win at this because I don't love it as much. It's so interesting because I tried a summer at investment banking. I worked at Nomura and I was in the investment banking group. And I remember walking the bank that summer and asking people if they didn't pay you this much money. Would you do this job? This is what you did. And honestly, people thought I was crazy. I mean, they just looked at me like, who is this crazy woman? And why is she asking me this question? Literally, the only person who said that to me, I love the yield curve. And I thought, finally, here's somebody who's in the right job. And it's interesting because both of us sort of had financial instability. So you would have thought that the money would have been enough, or. I mean, clearly it was something that was a necessity. I mean, it was in the beginning, just to be clear. Well, but even still, you would have been like, okay, that's the only thing. Like me. It seems like you also sort of were interested in something that sort of satisfied you on a different level. It was both an internal push and an external push at the time. There's the saying I grew up with that, if you don't want to be the general in an army, why do you want to stay in the soldier squad? And I looked around and I had no desire to be a leader in the private equity firm. And I didn't want the next promotion. It wasn't a career track I was interested in. And in that environment, if you're not moving up, you're kind of moving out. Deborah Martin Chase is a masterclass in reinvention. On her 28th birthday, having survived a car almost running her over, she goes home and breaks down crying. Overwhelmed and miserable in her life as a lawyer in Houston. She doesn't just stay there. She decides to change course and starts again at the bottom and digs into her true passion, film and tv. Her it is beyond inspiring. I was a poli sci major, loved politics. It was a really great experience. And coming out of that, I got an offer to work for the Dinkins administration. And in that moment, I was like, you know what? If I'm gonna go for it, let me go for the dream, which was always been to make film and television. Like, at what age did you know that you wanted to make film and television forever? I mean, I didn't even know it was a dream. You know, it was so far away. Cause I didn't know anybody, you know, you see it, you can be it kind of thing. I, you know. But yes, I always loved film and television. But by that point, like, you thought the dream was at least somehow within reach. Yeah, well, again, I had the law school degree in my pocket, plus some experience to boot. And I was divorced and I didn't have A mortgage for the first time. This was my moment. If I knew if I didn't try it now, I would lose that window. I want to talk about that for a second because there's a lot of people we know who sort of hit a hitch, find themselves married or in a job they don't like, but it's hard to pivot. But you somehow believed yourself enough to think you deserve something different. I was so miserable practicing law. And again, I don't mean to bash Houston, but it just. At that point, it just didn't work for you. None of it. None of it worked. I spent my 28th birthday on my couch in my den, crying the whole day. Cause I thought my life was over. Wait, where was your husband at the time? This was when you were divorced? No, we were, you know. Yeah, he's like, what are you doing? Crying? He's at work. Like, you know, I took a. You know. And the year that I had taken off in between, again, I was freelance writing, which is hard to do, you know, from Houston. But I realized that I had a contribution to make to the world. And that until I figured out what that was and got on with it, I was not going to be happy. So you basically decide you're gonna go for it. Do you move to la? No, that year I'm still working in Avon, but researching. So I'd met some people in the Dukakis campaign in the film business on a high level. So I talked to them. I talked to anybody they would refer me to. I went to seminars, I read books. So I could really understand how the movie business worked. And I discovered that the people who actually come up with the ideas for movies are either studio executives on the inside or producers on the outside. And I realized that's what I wanted to do. So that's when you figured out your purpose, at least figured out what the path would be. Once you figure out what the goal is, then you can make a plan and then you can move forward. The hardest part, and I've been there a couple times in my life, is when you don't really know what you want to do. And sorting through that and figuring out what you want, what you think your purpose is in life, and zeroing in on that, those are some of the hardest periods and hardest things to do. How can you stay resilient in a career that is upended every day? Well, that's what happened to Cindy Levy, CEO of the Meteor, because guess what? She was in the media business, which has had a lot of twists and Turns today, she advocates for women through the meteor, and she grapples with politics in a world that is quite messy. She shared with me her powerful advice for cultivating resilience. The thing that you're now focused on is under attack, and you're pretty resilient. We've definitely observed this here, but not everybody is resilient. So how do you remain hopeful? What do you worry about for other people? Because it's kind of a difficult time for people who are in that lane. It's incredibly difficult. And I mean, I think, first of all, like, you know, I would never sugarcoat it. I mean, it's really when you take a step back and look at where we are. You know, I talked about my mom. I grew up with this understanding that, like, science was sort of a truth, like, it was sort of her religion. And to see now what's happening at the nih, to see what's happening to just our basic concepts of, you know, respecting, you know, accuracy, respecting health information, respecting science, kind of tossed by the wayside. It's incredibly unmooring. Like, it's not just an obstacle. It's something that, you know, makes you feel like you've taken a step. You know, when you. You're on a staircase and you said the step that you thought was there is not there. It is that kind of feeling. And so I think that's real, and I feel it. But if somebody's depressed or feeling anxious or, you know, want to, you know, wants to curl up like a ball, like, what's the lesson that we can pass on to them? First of all, that is rational, you know, And I would never say to people, like, don't be depressed. Get over your depression. Get out there and do something. Cause we know that doesn't work. We know that doesn't work. But it's also like a totally. You know, I think it's a totally normal human impulse to be depressed. I think, first of all, focusing on the world that you inhabit personally, like your community, your workplace, what are you doing, you know, within your family? If you have people in your family that feel differently, like, what are you doing within the world where you are a protagonist to, you know, to change things, I think that's where you can also start to feel like real successes. I think about this because, you know, it can seem insurmountable, right? And I think that if you focus on a hyperlocal level, and by the way, you don't have to try to make enormous changes. You can start by making small changes, even Just getting to know your neighbors. I think part of what's happening is that there's just a lack of understanding and empathy. And there's a lot of things that are broken. It's not like one side is right and one side is wrong. But rediscovering our humanity, like, starts close by. Yeah. And that's where you also, like, you realize, oh, there are probably are things that I agree with these people on in some fashion. And I'm not doing that thing of, like, you know, it's on Democrats to reach across the aisle. Cause it's like, on everybody to try to work together. But I think, like, you know, just trying to have personal conversations rather than thinking of everything on this, like, great big political stage is important. And also just like, you know, try to remind yourself that there are a lot of people that feel like you do. And I'm sure for anyone listening to this, like, there is a group in your community. There's a group in your workplace. There's a group at your, you know, at your school. There are people, you know who are working on something that matters. And you can, like, find them and be with them. Because it's not. It's not like the entire world has decided that, you know, it hates these values that have, you know, pick anything. You can join the garden club. Just getting that sense of agency back, I think can help. If you're ambitious about your career, you may want to work in jobs that are perfectly aligned with your vision. Judith Kerr, president and publisher of Harper One group says the perfect job may not come, so you should embrace the opportunity that's been given to you. So I went to high school, and then instead of going to university or college, I did a cadetship at Grace Brothers, a big department store chain in Australia. And I decided after two and a half years of that course, it was heading in a direction that was not that I did not want. And I also was looking for a car, and I didn't have any money to get a car, so I got a job as a traveling salesperson selling cologne to pharmacies. It wasn't door to door. How did you know at that young age that that wasn't enough for you? Well, I never actually thought of things in those terms. I don't think of things as kind of like a race to the top. I feel like it's a sort of a journey that zigs and zags. And at the time, I wasn't that happy in that job. And I wanted a car. And I saw an ad that was advertising for a trainee traveling salesperson. And I thought, well, that solves two things. I get another job and I get a car. And then, of course, I was quite good at selling things. You were clearly selling from seven. Yes, I was. So the perfumes that I was then promoted into was Christian Dior cosmetics and perfume. And I was sent to Paris to sort of have a look around for a little bit. So I had a skill set that was sort of publicity and promotions and things like that. And then I had come to the end of my satisfaction with that job. I had met someone who worked in publishing. And then, as luck has it, I saw an ad in the paper for a publicity and promotions manager, American publishing company with an English branch that was setting up an Australian office. And they were looking for somebody who had publicity and promotions experience. And so that was my bridge. I was a third person employed. So it wasn't like they had all these people with years of experience in publishing. And I happened to satisfy their need to have somebody who could go out and promote the company. And then, you know, one thing led to another and that's how I got my start in publishing. You and I know lots of young people looking for a job and what is a pretty difficult job market currently? Yeah. When you think back to that part of your story, is there a tip or a lesson that you would take from that that we could give to somebody sort of who's starting out? Don't expect everything to be everything for you. So if you're really desperate to have a particular kind of job, really, that would be wonderful. But if that's not available to you, then take another job and then work your way towards that job or to that goal, or you'll find satisfaction elsewhere. But if you're always waiting for everything to solve all of your problems all at once, and this is for everything, then it's going to take you a really long time. So don't wait for perfect. No, definitely not. And then you can have lots of fun too, which is really nice. Taking risks is a big part of a successful career. Sarah Personat, CEO of Puck News, explained to me how her ability to be a systems thinker really created a career planning tool for her that gave her new opportunities and the confidence to pursue every single twist and turn. You didn't say at the moment. Let me think about it. They offer you the job in the moment, which is rare, and you actually accept the job in the moment for $23,000. I say, I graduated from business school with the lowest paying Job in advertising. So I understand that probably my dad would have said the same thing. What made you trust yourself enough? I don't know the answer to that question. Someone else recently asked me. They were like, when you take these, like, jobs, do you ever consider the things that you don't know how to do and as a result not go for them? And I was like, never. And I don't mean that in a place of ego. I actually have, like, a very low ego, and I work at that because I think it makes you a better leader. But I believe in the capacity to learn also. Very early days said, be the master of your own education. So there's nothing that you can't learn and there's nothing that you can't change. If the job didn't work out, I could go and get another job. Okay. There's two things in that. One is it's not so much the first job out of college or even out of business school. I mean, of course there's gonna be things you don't know. But you believed in your gut instinct because you reacted in that moment. Right. You didn't even wait to go see what else your other opt options were. Yeah, no, Well, I had other options. Right. But you didn't say, I'm gonna go weigh them. You just said, yes. Yes. Because in my head, I calculated very quickly what this would mean versus what those other jobs would mean. Do you know what, like, systems thinking is? You're definitely systems thinker. Yes, I. I like. It's the ability to see, like, the interconnectedness between all things, actions, people, moves. And I can do that very quickly. Now, I cannot do math in my head, so that's a challenge, but I can do. But it's like a chess game. You can sort of see the moves. Yes, exactly. Right. I can process things very fast. So in that moment, it didn't feel like a risk. It felt like this is absolutely the right thing to do. I think there's two things in that story. Right? You trusted your instinct. Yes. You're a systems thinker, but you trusted your instinct to say yes in that moment. And then you call your dad and he says, that's a terrible decision. And you don't waver. Right. It's kind of an interesting thing. Clearly, you had utmost respect for your dad. So then standing up in that moment must have also been complicated. I do think you have these moments in your life where you see, whether it's your parents or other role models no longer having the same insight as you might have in the environment or the ecosystem that you are in. I think in my career. And that was like one of many, many times that my dad told me I was making the worst career decision. Yes, three. Three. Not that we're counting, yes, but three. And for me, instinctually, what I saw around what was happening with consumers, the passion that I felt for this particular time and role of what was happening in the advertising industry, because that was really interesting too. Like media and creative were, were decoupling. That was fascinating. Like I thought what I was going to learn, the experience I was going to have and the dynamic shifts that were happening with were something interesting to be a part of. And I wanted to lean into that. Even though financially the reward might not be as good or that maybe it would look better to have an investment bank on my resume. Like I am very much a long term planner. But I wasn't planning for what that would be. I was planning for what this experience was going to give me in the moment. And that felt right to me. And yeah, I definitely had like the strength and courage to stay with it and stick with it. And probably within the first six weeks of being there, I knew I wanted to run an agency someday. Advancing in your career might be as much about the people you surround yourself with as the choices that you make. Vanessa Barboni Halleck had a surprising experience of finding camaraderie in the cut, cutthroat world of finance, which she found herself in after college. You called parts of that experience you being overtly confident but internally overwhelmed. Yeah. What does that mean? It was exhausting. I mean, the job itself, I had no, I think like sort of emotional preparation for, in terms of just like the amount of resilience it required and new information and pressure to perform and like, downside if things went wrong. So it was definitely like an internal pressure cooker and, you know, not a great thing. But like growing up with my dad as an academic, like, you know, dinner table was a debate, but instead of being a debate that was like curiosity oriented, it was like a debate about like being right. And I think that, you know, I was terrified to not know the answer and I was terrified to be wrong. And so that like outward confidence was very much like, I know I've got this. And I somehow thought that like, you know, not knowing was like a weakness. You know, as an entrepreneur now I have a completely different perspective on that. But at the time I really felt like, you know, I had to be, you know, better, faster, stronger, always know the answer. And that's Exhausting too. So it's funny, I had a summer job in investment banking. I was a kid who had financial insecurity after my father's passing and for sure I had student loans. So it was appealing to have that summer job. They hadn't gotten the note about them wooing us to want to come back. So we literally slept under our desk for that summer job. I did not find a real sense of camaraderie in that job. Now I didn't do trading, I didn't invest in banking, but it was definitely a dog eat dog kind of mentality. And there wasn't tons of deals. So where there was, there was lots of crazy energy. Did you find a community at all and at work a bit? Yeah. And I think that had a lot to do with the culture. They were really selective about who they brought into the classes, but they didn't structure it in a way that like, it was like two to one interns to job opportunities. Right. So you didn't. It wasn't this like death fight to get the offer. So it didn't feel like there was a sort of like one upsmanship. And so we really, we really bonded as like a class. And you know, again, I had a great first boss and I'm still very much in touch with, you know, a bunch of the people that I started with, which was really cool. And plenty of other examples where like I felt like I was literally in outer space. But like as an incoming class we kind of had each other's back. It was nice in those moments where you felt like you were from outer space. How did you navigate that? I think by editing myself, unfortunately. What does that mean? There were just, you know, there are aspects of my like interests and personality that I just, I didn't see how they fit in. And so I think with the exception of a couple of people, including like a very close girlfriend of mine that I was lucky to work with, you know, for many years, I sort of just like didn't show up as my full self to the point that, you know, by the time I was sort of at the tail end of that finance career, I almost was like, where, you know, where is the rest of me? Do you think that you sort of self edited thinking that that was the answer to success or. Totally. No one ever told me like, oh, you know, don't say that, you know, or don't be that aspect of yourself. It was very much like self imposed. But you know, I didn't see like a lot of the folks like having the same Interest as me. But, you know, I kind of think back and I'm like, was everyone just self editing? I don't know. I mean, it's an interesting thing. I also am not necessarily of the camp that like, you know, you bring it all to the office, but I think to your point of like kind of the survival instinct and also like moving around, you become a chameleon a little bit, which doesn't mean that you're performing in a way that isn't you. But it definitely was that, like, oh, I'm just gonna leave these things over here. And I definitely felt the need to constantly prove myself. AI is going to transform many jobs and industries in the coming years. Fede Garcia, a former chief creative officer at bcw, an advertising agency, talked about the many ways creative professionals can stay relevant despite the threat of AI. I think it's quite interesting because when I grew up in advertising, you started doing the menial jobs, right? And that's how you learn the craft. You go wrote a piece of copy a thousand times and you brought it to your creative director and he would give you feedback and feedback and feedback and feedback until you get it right. There is a part of that that I feel is going to disappear quite quickly. And not because kids are not worth it anymore. It's just because of the economy that we live in. If you have a junior copywriter, he goes, he writes something, he brings it back, he goes, right, he brings it back. And you can go for a week now, you can have that with AI within seconds. And you don't have to teach AI, you don't have to treat well AI. They don't have excuses. They are not, they never get tired, they never get angry. So it's getting quite hard in that sense. Because learning the craft, it was at least how I, how I learned it. This was by doing. And now you have a machine doing it for you. And I used to learn by being in the office watching other people do it. And now I don't know. People don't always go in the office and don't go to the office. So it's changing radically. So if I would give advice to anyone, develop good taste. And I don't know how you do it. Talk to people, read a lot, see everything, be voracious about the kind of content you consume. But the fastest thing or the best thing you can do is build amazing taste and a unique taste. I think AI makes a lot of things faster. I think you cannot replace the human element, not yet. There's still maybe never Maybe never. Hopefully never. Hopefully never. But yeah, AI will come up with 100 ideas in a second. But there's gonna be somebody yet saying this is the one. And that, in the end, is, to me, is just gut feeling, experience, taste. I say it's like having a good intern. You still have to check it. You still have to do the thinking yourself and figure out the context. Yeah. And the thing is coming incredibly fast. Thank you so much for listening. I'm Mariam Banakaram. If you've enjoyed enjoyed this Hark list, you can subscribe to the messy parts on the Hark Apple.
Host: Maryam Banikarim
Date: December 22, 2025
Theme: A tapestry of candid, messy, and inspiring stories from high-achieving women (and a few men too) who zigzagged, stumbled, and persevered to carve out extraordinary careers despite uncertainty, self-doubt, and the pressure to conform.
In this "best of" Hark episode, Maryam Banikarim curates standout moments from a year’s worth of revealing interviews. With stories from comedian Negin Farsad, SNL alum Ana Gasteyer, beauty founder Katie Sturino, restaurateur Vicki Freeman, and high-profile leaders across industries, the through-line is clear: successful people embrace uncertainty, rewrite the rules, and yes, get real about the messy parts. A recurring message emerges: career paths are never linear, self-doubt is normal, and the best way forward is to own your story—and keep moving.
Negin Farsad, Comedian
Ana Gasteyer, Actress/Singer
Katie Sturino, Founder, Megababe
Vicki Freeman, Restaurateur
Irina Novoselsky, CEO of Hootsuite (ex-Financier)
Deborah Martin Chase, Producer
Cindi Leive, CEO, The Meteor
Judith Curr, Publisher, Harper One Group
Sarah Personette, CEO, Puck News
Vanessa Barboni Hallik, Entrepreneur (ex-Finance)
Fede Garcia, Advertising Creative
This “best of” curation affirms the real story of success: it’s nonlinear, often messy, and powered by courage, openness, a willingness to act despite fear, and a stubborn commitment to your truest dreams. Whether you’re starting out or leading, there’s something in every story here to inspire you to rewrite the rules—and talk honestly about all the messy parts along the way.
For more real, unfiltered career wisdom, subscribe to The Messy Parts with Maryam Banikarim.