25 Famous Women on Switching Careers

Photo-Illustration: by The Cut; Photos: Getty Images

Doing the Most is a special series about ambition — how we define it, harness it, and conquer it.

It’s never convenient to switch careers — why risk your livelihood for a new direction that might not pan out? But the truth is, many successful people don’t start off in the field where they wind up. And more often than not, people’s previous experiences are often what lead them to excel in the career they were meant to be in. Below, 25 famous women including Alexandria Ocasio-Cortez, Cardi B, Victoria Beckham, and more break down their nonlinear career trajectories and why they took the U-turns that brought them to where they are today.

“When started stripping, I just wanted to make $20,000. If I make $20,000, I thought, I’ll open a fucking business, and I won’t have to strip anymore. Strippers talk a certain way. The stripper attitude is, I’m not ashamed of being a stripper because a lot of these bitches don’t have shit. A lot of these bitches don’t have a place to stay, don’t have no car, can’t afford this, can’t afford that. That mentality stuck with me. I felt like, You’re judging me, but I’m making more money than you. I felt like nobody could shame me for being a stripper. I had a manager, and every time we would be in the car driving to bookings and shit, I always used to remix songs and he’d be like, ‘Yo, you’re really quick and witty. You be having these bars.’ And I was like, ‘Yeah, yeah, yeah.’ He was like, ‘I produced some songs before for Lil’ Kim. Why don’t you try doing music?’ And I was like, ‘Bro, I don’t want to waste my time. I just want to make fucking money.’ And he’s like, ‘But this might make you money.’ He kept telling me, ‘You need to think bigger.’ And that’s exactly what we did. We went to the studio, I did a song called ‘Stripper Hoe,’ and after a while, my goals started changing. Not only did I want to make money, but I wanted to be on the radio. In the strip club, I didn’t want people to just clap for me. I wanted them to sing my shit.” — Interview, February 2021

“When I was in my 20s, I was working in nuclear energy policy and management and budget for the White House, thinking, ‘There’s got to be something more fun than this.’ And then I saw an ad for a specialty-food store for sale in the New York Times, and it was in a place I’d never been before: West Hampton. So my husband, Jeffrey, said, ‘Let’s go look at it.’ To say that I knew nothing about what I was getting myself into was an understatement. I’d never run a business before, never even had employees working for me. But when I saw the store, I thought, ‘This is what I want to do.’ So I made the woman a low offer, thinking we’d have time to negotiate. But the next day she called me and said, ‘I accept your offer.’ That’s when I said to myself, ‘Oh, shoot. Now I have to run a specialty-food store.’” — Time, February 2016

On directing: “Immediately it clicked for me in a way that acting truthfully never had, and it all made sense. I realized that this education I had in front of the camera, this is what it was for, to do this.” — Teen Vogue, February 2022

“I was a film publicist, so I represented a lot of filmmakers and I was always around them. I [started thinking], ‘They’re just regular people, like me, with ideas. I’ve got ideas.’ That’s literally how it started. It was definitely a career change; I didn’t make my first little short until I was 32. It was kind of intimidating coming into it so late — all these whippersnappers fresh out of film school, I couldn’t do any of that. But I did start to recognize that being so close to really great filmmakers and watching them direct on set and the experiences that I did have, although different from film school, were still super valuable. I learned just from being around.” — Interview, October 2012

On working as a waitress before being a representative: “So many of the people that I worked with had parents that passed away, or they were born in circumstances that led to these outcomes. Whereas in society we’re taught you’re there because that is what you deserve. You didn’t work hard enough. You didn’t educate yourself enough. You had messed up in some way.” — Intelligencer excerpt of The Unprecedented AOC, February 2022

On starting her diplomatic career at age 40: “I really waited a long time [to get married] — three days after I graduated. And I did want to be a journalist. I had been one of the editors of my school newspaper. My husband was a journalist. I did what you’re supposed to, worked on a small newspaper while he was in the Army. And then, this is classic. We went to Chicago, where he worked for the Chicago Sun-Times. We were having dinner with his managing editor, who said, ‘So what are you gonna do, honey?’ I said, ‘I’m going to work as a journalist.’ And he said: ‘I don’t think so. You can’t work on your husband’s paper because of [Newspaper] Guild regulations. And you would not want to work on a competing paper.’ Instead of saying what I might say today, I just kind of saluted and did something else. I worked for a while at Encyclopedia Britannica, then I had my twin daughters, then I went to graduate school and did a lot of volunteer work. In 1977, I started working as chief legislative assistant to Sen. Ed Muskie. Then, in ‘78, I went to the Carter White House. That was the first time I really had a full-time job.’” — The Wall Street Journal, May 2012

On being an example of why we should normalize adult actresses venturing into mainstream TV: “It feels necessary. I just think it should have always been a thing. Why not? Let’s just see actors as actors. Porn is actually shot very professionally, with big cameras and marks. So there are a lot of things professionally and technically that are very similar. All of the technical things I already knew before going on the set, but the subject matter is very different.” — The Cut, February 2022

“There’s no question that changing careers is the good result of a bad quality I have, which is a short attention span. But originally I went into movies not because I was burnt out on journalism but from economic desperation. When my marriage broke up, I had two kids and I figured I’d better get my act together because nobody else was going to help. That’s a realization a woman comes to very late in life: It’s just me. So I started doing scripts because everyone was doing it. It saved me from having to live in the country or some fate worse than death.” — Rolling Stone, July 1993

“When I started The Mindy Project after The Office, networks were like, ‘Okay, we finally feel like she’s ready to do it.’ That’s 150 episodes of TV that I had either acted in, written for, or produced! I think you’re less set up for failure when you have put in all that time, but I wonder if I could have done it sooner. Where am I in my career? I’m shifting from performer-writer to writer-performer, maybe, where my focus is more on the writing side.” — The Hollywood Reporter, October 2021

On leaving the film industry to start Goop: “I really liked acting … But at a certain point, it started to feel frustrating in a way not to have true agency, like to be beholden to other people to give you a job, or to create something, to put something into the world.” — People, February 2019

“I was sitting in a sky-rise office, doing legal work that wasn’t fulfilling to me, and I couldn’t help but ask — what’s it all for?…If there’s some part of you that’s questioning your career, it’s important to listen to that. Our hearts sometimes know ourselves better than our minds do. For me, that meant pursuing a life of public service — a path I’ve been able to maintain since that major swerve. But even since I made that change, I’ve shifted roles and jobs as my life demanded it. There are times when you can work 60 or 70 hour weeks for less pay, and there are times when you may need to make more money or be home more consistently for your family. Knowing that at the outset — that any career change will probably be followed by more changes, in varying degrees — can help you keep things in perspective if and when you start to re-evaluate things once again.” — Goodreads

“I was pre-med. I did not go to medical school. My mother would be very excited that people think I did. I was taking a year off before medical school, but I was afraid to leave science. So I got a job doing chemistry, and it was the first time that I’d lived alone. I already watched a lot of TV … when there’s no one else to talk to, then that’s all you do … And I was like, you know what? I could do this. And if there’s a time to do it, do it now. And so that’s when I decided that I wanted to get into television. [Through] my research, i.e. more TV watching… I knew I wanted to get into sitcoms, so I went to an acting class at the Raleigh Little Theatre. It was like out of a bad movie… then I drove cross-country with a friend to try to make that Hollywood thing happen … [Comedy Central] had a stand-up competition … And I did it, and I got into the semifinals and then to the finals, and then I won. I won a car. I won a year’s supply of Taco Bell… I used them all.” —NPR, April 2019

On starting her clothing line: “I was very aware that people would have preconceptions because I was a Spice Girl and I was married to a footballer. So I knew what people were thinking, but I really didn’t focus on that. I was very focused on what I wanted to do … I liked the fact that I didn’t know a lot. Because knowing what I know now about the fashion industry, would I have had the guts to do what I did then? Probably not. I think I was quite innocent and naïve. There was a lot that I didn’t know. I think that was good because I probably would have been terrified. When people say, ‘Were you not nervous? The fashion industry is really scary.’ And I was a pop star, saying, ‘Hey, I designed a dress.’” — WWD, June 2018

“I [worked] at a law firm and then in finance, at jobs that I hated that paid enough to pay off my loans and to help my parents with their mortgage. I was seriously depressed and miserable because I was not giving back to the world. The money wasn’t making me happy, and I felt more and more beholden to it, more and more scared. And so I quit, and ran for Congress. I lost that race, but I put so much personal savings into my race. I hadn’t had a paycheck in eight months. I was broke. But I wasn’t going back. No longer will I work in a job that I hate for a paycheck.” — The Atlantic, July 2018

“I started modeling my last semester in college when I was studying abroad in Madrid . Then I started acting — a lot of costume dramas and foreign productions. For one movie I shot in Cuba, the director wanted me to be a bit rounder. So I gained 20 pounds. After that, I wanted to continue to model — and to lose the weight. But I had never really tried to lose weight, so I had to think about how. I’d always been passionate about cooking, so I just took the fat out of everything I cooked, and tried to limit the carbs. My first cookbook came out of that process. Then the Food Network called and I eventually got a development deal with them. From there, I did some documentaries on food — and then I got the call from Top Chef.” — Into the Gloss, March 2018

“I considered pursuing a career in beauty, but I went into finance instead, knowing it would give me complete financial independence. Then, after a few years, I applied to business school and planned to step into the beauty industry. But it turned out I couldn’t get a job. I was at Harvard Business School and every brand I spoke to was like, ‘Yeah, get in line. We have all the top business schools applying and everyone else has beauty experience.’ … About six months before graduation my co-founder, Hayley Barna, and I came up with the idea for Birchbox. Initially our intent was, ‘We’re going to graduate from business school, so let’s write a business plan.’ That was the goal: write a plan. And when we saw this amazing opportunity waiting in beauty we just couldn’t settle. We couldn’t sleep.” — Coco’s Tea Party, March 2017

“I remember when my second-grade teacher, Mrs. Lee, told me that I could be a teacher when I grew up. I was so excited I couldn’t wait — so I lined up my dolls and taught them how to read. When I was done with school, I became a special needs teacher and then eventually went on to teach at law school. And that’s where I thought I was always gonna be. But there was so much at stake in the 2012 election. I’d spent my whole career studying why working families were going broke, and it was getting worse. I kept thinking about what kind of country I wanted my grandchildren to grow up in. What if the Republicans and big bank CEOs undid the new financial regulations and crippled the consumer agency we’d just built? If I didn’t do everything I could to stop them, I wouldn’t be able to live with myself.” — Shondaland, July 2019

“There’s definitely something artistic about modeling. It just wasn’t artistically satisfying for me because I like to say what’s on my mind. And in that business … Even in acting, you show up to play a character, but if the director will allow it, there’s a creativity you’re part of. That doesn’t exist in modeling. You might have a passion for clothes, but you stand there while they put what they want on you, like it or not. Here’s the other thing: I missed discipline. I was a ballerina, and ballet is something you have to work hard at. I couldn’t figure out what I had to work hard at to be good at modeling — other than losing five pounds.” — Oprah, November 2005

“[For] a lot of my early years, I didn’t think that writer was something you could do as a job. I always thought I was going to do something else and write on the side. It wasn’t until I started working in publishing and I realized that really wasn’t the job for me that a mentor said, ‘You keep saying that writing is going to be on the side. Why don’t you try and switch it?’ I looked at my savings and I went, ‘Okay, I need to try this.’ I went to grad school and then I said, ‘I have this amount of time that I can afford to try and finish drafts of a novel and if I can’t, then I’ll have to figure out something else to do.’” — Shondaland, April 2018

“I was at a crossroads in 2010, bored out of my mind in my cubicle, making a living writing stories [at People magazine] that didn’t matter at all. I wondered if that’s all there was, and found refuge by waking up an hour earlier every morning and showing up at my desk to write to myself. Taking that time and turning inward for stories that mattered changed the trajectory of my life, and led to the writing of my first memoir, Redefining Realness.” — Quartz, February 2018

“I started as a high-fashion model. I was very naturally thin and then my body began to change. From there, I had a choice to either quit fashion, lose a lot of weight or to come up with something different. My mom helped me to strategize over pizza, ironically, to change my career to be more commercial. So then I did Victoria’s Secret, Sports Illustrated and Cover Girl, different brands that were reaching a broader audience. That was the first step of being a bit more open. From there, I created [America’s Next Top Model to give] 10 to 15 people per cycle the chance to experience the modeling world and potentially have a modeling career while millions of people watched. My mission was not to create a show of ‘Oh, look how hard modeling is.’ I really used the modeling platform as a vessel to expand the definition of beauty.” — Adweek, February 2019

On going from working at the U.S. Department of the Treasury to Google:  “There are so many times I’ve seen people not make that jump because they’re afraid they’ll — and I’m doing this in air quotes, you can’t see me— ‘move backward.’ So let’s say you’re a lawyer and you’ve decided you don’t want to be a lawyer, you’d really rather be in marketing, and you’re 35… but you’re at a certain level and you’ve never done marketing so no one’s going to hire you at that level, so you’re gonna need to take a step back, meaning go down a couple levels. If you can financially afford it, and you’re gonna work the next, I don’t know, 30 years, who cares about ‘going down?’…I came in [to Google] as what we call the business unit general manager. The first team I ran at Google had four people. The Treasury had tens of thousands.” — When to Jump podcast, November 2017

On going from acting to founding The Honest Co.: “I think when you start off and you’re known in one career, for people’s perception to be changed, they sort of need to see it to believe it…There aren’t a lot of women who have multi-hyphen job descriptions, or have done many different things in their careers and have been successful in them … It’s more of a quiet satisfaction. It’s more, ‘I always knew I had it in me, and you didn’t believe in me, and now, hopefully, you see something or your perspective is different, and you’re judging things differently. And hopefully, you’re opening your eyes up to what is possible.’” — Cosmopolitan, August 2017

“I am a pediatrician through and through. My life, as I envisioned it, was to take care of children and teenagers in my practice and simply retire and then teach medicine. But I think this is one of those moments in history when we’re all going to look back and think ‘Okay, what did we do after the 2016 election? What did we do when we saw divisiveness in our country, when we saw attacks on women’s reproductive health care, when we saw attacks on our health in general? Were we on the correct side of history?’” — ABC News, October 2018

“I spent my career in corporate America and I traveled a lot for my work. I think the last job I had before I started [Salt & Straw], I was traveling from Seattle to New York almost weekly. I wanted to do something that was community based and where I could get to know my customers and employees and my neighbors and be home walking my dogs. I wanted to open this one shop to accomplish that … My boyfriend at the time — who I’m still with, we now have three kids — I remember sitting up in bed at like 3 in the morning when we were getting ready to open the shop, and waking him up and saying, ‘What if this all falls through and it fails? What are we going to do?’ I think about that a lot, even today. He didn’t say, ‘It’s going to be okay,’ because that wouldn’t be okay, that would be a bummer. But he said, ‘You’ll do something else, you’re really talented and you’ll find something else.’ I liked that answer because I think when you’re an entrepreneur, you have to believe in yourself blindly and be willing to go and leap off a cliff and not know where you’re going to land.” — Shondaland, July 2018

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