Looking for some careers advice? From Oprah Winfrey quitting her eponymous talk show to Reese Witherspoon setting up her own production company, these are the career-defining moments that changed the lives of some of the most remarkable women in the spotlight forever.
There’s an unwritten rule that most successful people in the spotlight have overcome some form of adversity in their lives. It’s a narrative that we’ve especially come to expect of well-known women, and one that they are continually asked to share the higher they ascend to fame: the rejections, the setbacks, the struggles and the hours of blood, sweat and tears that it took to chase down their dreams. After all, who doesn’t love a Cinderella story?
The “making it” stories that are harder to come by, however, are those that tell of how some of the most influential women in our society found their groove on their own terms. It is only by hearing tales of diligent list-making, encouraging conversations, and quitting day jobs in a quantum leap of faith that we really begin to understand how the remarkable women of our world altered the course of their lives by daring to be different.
Below, 12 remarkable women from Oprah Winfrey and Constance Wu, to Michelle Obama and Reese Witherspoon, reflect on the pivotal forks in the road that changed their lives forever.
Careers advice: when J. K. Rowling triumphed as a single parent
“I couldn’t have written this book if I hadn’t had a few years where I’ d been really as poor as it’s possible to go in the UK without being homeless,” Rowing told The Daily Show in 2012. “We were on welfare, what we call welfare, I would call benefits, for a couple years.”
Nowadays, Rowling is president of Gingerbread, a campaigning organisation which supports single parents and their children. “I would say to any single parent currently feeling the weight of stereotype or stigmatisation that I am prouder of my years as a single mother than of any other part of my life,” she wrote in an essay for the charity in 2010.
Careers advice: when Constance Wu decided to put herself first
Last year, Constance Wu triumphed in her second lead film role as the dancer Destiny in heist movie Hustlers. But according to the actress – one of the most famous Asian-Americans in Hollywood who hit the big time in Crazy Rich Asians – it was reorienting her perspective on money as a measure of success that paved the way for immense creative freedom in her career.
“About a couple of years before I got Fresh Off The Boat, I was really broke,” she told Vulture. “I was in tens of thousands of dollars in debt: credit card. Car. Personal. Student loans. I paid for my college all myself. I didn’t have a boyfriend. I was really alone and lonely. I was new in the city, and I didn’t have a community of friends in L.A. [Tears up.] I was like, Are you okay if your life stays like this, where you’re waiting tables, struggling to make ends meet? Are you still okay doing this when you’re 45? I decided that I was.
“That’s when my work improved because it wasn’t results-oriented. It wasn’t like, I heard that this director likes crazy characters, so I’m going to try to make it crazy. I was like, What do you, Constance Wu, envision for the character? What is the special thing you can bring even if it keeps you from getting the part? This is your chance to do it. Let’s do it. That way when you don’t get the part, they have taken nothing away from you because you got to do what you wanted to do. That’s when I started booking work.”
Careers advice: when Lupita Nyong’o decided to take control
In 2013, Lupita Nyong’o’s breakout role as Patsey, a slave on a cotton plantation in 12 Years a Slave, firmly cemented her status as a rising star in Hollywood. Still fresh out of Yale’s School of Drama, Nyong’o found herself saddled with a huge weight of expectation; something she initially struggled to come to terms with, until she learnt that she alone has the power to define the course of her career.
“Different people would say, ‘This is your moment, this is your moment,’” she told AnOther. “That was kind of perplexing. What does that mean? What does that mean in actual practice? I had to really sit with myself and figure out what I wanted my life to look like. There was the expectation that, when your career explodes, the world is at your feet, you can have anything you want — that’s the Cinderella version of it. Then there are the real questions — What do I have an appetite for now? What does success look like to me? Now that I’ve achieved all this, what does failure look like? I really needed to define those three things, not on the world’s terms but for myself.
“For me, success equals longevity, success equals the luxury of choice. Even when I was in school, they were always preparing us for whatever came our way. We were not honing our skills at choosing what we wanted to act in, we were honing our skills at making a meal out of whatever little got thrown at us. So, if you were playing cop number three you could still find the joy, the life, humanity in that, because it is expected that it is a long road to roles of substance in the industry. They’re not really training you for instant success and choice. That’s what the accolades that came with 12 Years gave me — they afforded me a choice.”
Careers advice: when Reese Witherspoon decided to challenge the patriarchy
“I was in this position where I was making studios a lot of money, and I had for years and years, and they didn’t take me seriously as a filmmaker,” she told The Hollywood Reporter. “Somehow, they didn’t think that 25 years of experience could add up to some inherent knowledge of what movies work and how to keep them on budget. And you think about the kind of guys who come out of Sundance and get gigantic jobs off of one, like, ‘Oh, I see the potential.’
“I don’t want to just admire problems,” she continued. “And I certainly don’t want to leave this business the same way that I found it. That message - that you shouldn’t dream a little, girls, that you got enough of your pie already - is not OK. When people try to tell you to stay in your lane, don’t listen. Do not listen.”
Careers advice: when Opray Winfrey quit her talk show
In 2011, after 25 years and 4,561 episodes, media mogul Oprah Winfrey wrapped her hugely successful daytime talk series The Oprah Winfrey Show. The queen of daytime TV wanted to pursue new opportunities, but was faced with criticism and doubt from naysayers who declared that she had made a fatal career move.
“The most afraid I’ve ever been is after leaving the Oprah show and the struggle with [my network] OWN,” she told People. That’s as close as I’ve come to feeling defeated. Even in the middle of that defeat, I knew that it would pass. I would say ‘I’m going to admit this is bad right here. But this isn’t your whole life’. I didn’t know how long it would last. But in 2012, I took a beating. Everybody was saying, ‘You should have kept your day job, Oprah. It’s over’. People were essentially saying, ‘You are cancelled. What a mistake’.”
With the support of her partner, Stedman Graham, and former Paramount and Fox CEO Barry Diller, the TV icon grew resilient to the negative press and took confidence in the new phase of her career.
“What I learned is that I’m the only one out here internalising every move, like it’s defining who I am… Now we’ve turned it around, and I couldn’t be prouder of Greenleaf, Queen Sugar and the fact Tyler [Perry] created the foundation for our scripted programming, saying ‘I’m going to help you out’. For me it’s the great reward.”
Careers advice: when Alexandria Ocasio-Cortez experienced sexual harassment
Before millennial Democratic firebrand Alexandria Ocasio-Cortez became the youngest woman to serve in the United States Congress, she had taken up bartending and waitressing jobs to make ends meet. It was during this time, as she worked to supplement her mother’s income, that she resolved to change her family’s fortunes.
“What really shaped her politically, though, was coming home,” David Remnick wrote in a profile in The New Yorker. “The crucible was the aftermath - moving back to the Bronx.” With her father gone, her mother had taken jobs cleaning houses and driving a school bus. The family went into debt and the house was on the verge of foreclosure. The experience, she said, was humiliating and paralysing. Ocasio-Cortez put her career ambitions on hold. Her long days as a waitress and bartender, dealing with sexual harassment (“people touch you, they tell you things”) - the experience was hard, but it was formative. The family eventually sold the house, and Ocasio-Cortez’s mother, in order to save money, moved to Florida, where she now works as a secretary.
Careers advice: when Michelle Obama sat down with schoolgirls
Two months after her husband became the first African-American president of the United States, former First Lady Michelle Obama visited the UK for her first official trip overseas. Whilst in London, she met with a group of schoolgirls from the Elizabeth Garrett Anderson School in Islington, north London. Despite feeling “overwhelmed by the pace, unworthy of the glamour, anxious about our children, and uncertain of my purpose,” she realised that her newfound position would provide powerful representation for other marginalised girls growing up with the weight of racism.
“You had only to look around at the faces in the room to know that despite their strengths, these girls would need to work hard to be seen,” she wrote in her memoir Becoming. “There were girls in hijab, girls for whom English was a second language, girls whose skin made up every shade of brown,” she says. “I knew they’d have to push back against the stereotypes that would get put on them, all the ways they’d be defined before they’d have a chance to define themselves.
“Here, finally, speaking to those girls, I felt something completely different and pure - an alignment of my old self with this new role,” she continued. “Their faces were hopeful, and now so was I. For me, it was a strange, quiet revelation: They were me, as I’d once been. And I was them, as they could be.
“The energy I felt thrumming in that school had nothing to do with obstacles. It was the power of 900 girls striving.”
Careers advice: when Emily Blunt refused to be pigeonholed
“One of the producers on set kept saying, ‘This is going to be big,’ but I had no idea it would hit in the way that it did,” she told Buzzfeed. “And that men would be dragged along by their wives, unwillingly, and then love it and go see it again and tell their friends. It was a movie that everybody loved and everybody saw, and so when that happens, your life - if you’ve previously been unknown - is going to change. And my life turned on a dime. I remember I used to go to this bakery in L.A. every day, and one day I went in and everything had changed because the movie came out.
“I got offered every bitch on the planet. I really was trying to turn down every acerbic British person that I got offered after that movie came out. I just had to be careful. What I tried to do, really, was stand by the choices that I had made beforehand. I wanted to do different work, I want to do character work, I don’t want to be an ingenue, I don’t just want to do one thing.”
Careers advice: when Laverne Cox saw other trans women star in a major TV show
In 2014, transgender actor Laverne Cox, best known for playing hairdresser Sophia Burset in the Netflix prison drama Orange is the New Black, appeared on the cover of Time magazine under the headline, The Transgender Tipping Point: America’s next civil rights frontier. The cover was heralded as a historic moment for trans visibility, but although Cox counts it as a career-defining moment, in an interview with Variety, she reflected upon a stint in reality TV that became a springboard for her career.
“One of my big breaks has been on reality TV,” she explained. “I did a show called I Want to Work for Diddy 10 years ago on VH1. I was sort of competing to be P. Diddy’s personal assistant. And that led me to having my own show called Transform Me, which was a makeover show with two other trans women, traveling around the country, making over women who were not trans using what we had learned to transform ourselves. It was a flawed show. But it was great for me at the time. I was interested in having trans people in middle America’s living rooms every week, because I thought that would help change some stuff.”
As well as looking back on her formative career moments, Cox also credited the groundbreaking TV series Pose, about ballroom culture scene in 80s New York, for inspiring a “tipping-point moment” in the course of her career.
“What I think is going on now that’s really exciting for me, though, is I feel like Pose has changed the game,” she continued. “I sat and watched the first episode and I just cried, because I knew this talent existed. It felt revolutionary. I said to myself, ‘This proves that we can do the job, that we can lead shows, that we can write, that we can direct. We can tell our own stories, and it can be brilliant. This is going to change the game’.”
Careers advice: when Tina Fey learned to say yes
Tina Fey may be one of the most successful comedians in Hollywood, but when she first arrived on the set of Saturday Night Live as a writer in 1997, she was struggling with impostor syndrome. That was until she discovered a folder of motivational quotes that she had taken during an improvisational acting school in Chicago.
“As soon as I saw it, I knew what it was,” she wrote in an essay for Oprah.com. “There were quotes written all over the front of it. Some of them were: ‘Greet everything with yes’ and ‘make statements instead of putting the burden on others with questions’…
“The things I learned in that class became part of the way I live my life. A couple of times I’ve been called on to do things - jobs or whatever - where I’ve felt, maybe I’m not quite ready. Maybe it’s a little early for this to happen to me. But the rules are so ingrained. ‘Say yes, and you’ll figure it out afterward’ has helped me to be more adventurous. It has definitely helped me be less afraid.”
Christobel Hastings is Stylist's Entertainment Editor whose specialist interests include pop culture, LGBTQ+ identity and lore.