25 Famous Women on Their Career Milestones

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Career milestones come in many different forms. Below, 25 famous women, including Lady Gaga, Alexandria Ocasio-Cortez, and Chimamanda Ngozi Adichie, share how certain jobs and opportunities unmistakably altered their lives and careers.

1. Sandra Oh
On her Killing Eve leading role: “One thing I will share with you — when I got the script for Killing Eve, I remember I was walking around in Brooklyn and I was on my phone with my agent, Nancy. I was quickly scrolling down the script, and I can’t really tell you what I was looking for. So I’m like, ‘So Nancy, I don’t understand, what’s the part?’ And Nancy goes “Sweetheart, it’s Eve, it’s Eve.” In that moment, I did not assume the offer was for Eve. I think about that moment a lot. Of just going, How deep have I internalized this? [So] many years of being seen [a certain way]: It deeply, deeply, deeply affects us. It’s like, ‘How does racism define your work?’ Oh my goodness, I didn’t even assume when being offered something that I would be one of the central storytellers. Why? And this is me talking, right? After being told to see things a certain way for decades, you realize, Oh my God! They brainwashed me! I was brainwashed! So that was a revelation to me.”
Vulture, April 2018

2. Chimamanda Ngozi Adichie
“I was completely unknown. I wrote short stories, got many rejections, and then finally got an acceptance. I wrote a large and terrible novel that I sent out and that was rejected multiple times. And then I wrote Purple Hibiscus and a nice agent said she would ‘take a chance on me.’” —The Guardian, August 2016

3. Beanie Feldstein
On acting in her first solo lead: “I was so used to and so in love with the process of being alongside someone else, the dynamic and the learning experience and the process [of making Lady Bird with Saoirse Ronan and Booksmart with Kaitlyn Dever]. They were my favorite things. I got to go on a journey with them, and this script kind of looked at me and it was like, Well, what if she’s alone? What about those girls who don’t get those best friends at 15? There’s so many girls like that out there too, and they deserve to have their stories reflected back to them.” —IndieWire, May 2020

4. Michelle Obama
“Part of why I knew my book had to be done, and done well, is because it’s a rare moment in history that a black woman gets to tell her own story. Success stories look a certain way: They’re male; they’re white; they’re wealthy. That’s what power looks like because we’ve been taught that. And we question stories that are different from the ones we’re used to. How many stories do you know where millions of people are hearing about strong women, told by a woman, and hearing her pain?” —the New York Times, November 2018

5. Justice Sandra Day O’Connor
On becoming the first female Supreme Court Justice: “I was working in my office on the Arizona Court of Appeals. I was at the court in my chambers when the telephone rang. And it was the White House calling for me, and I was told that the president was waiting to speak to me. That was quite a shock, but I accepted the phone call, and it was President Reagan, and he said, ‘Sandra?’ ‘Yes, Mr. President?’ ‘Sandra, I’d like to announce your nomination to the U.S. Supreme Court tomorrow. Is that all right with you?’ Well, now, that’s kind of a shock, wouldn’t you say? … I felt a special responsibility … as the first woman. I could either do an adequate job so it would be possible for other women to be appointed without [people] saying, ‘Oh, see, a woman can’t do it,’ so it became very important that I perform in a way that wouldn’t provide some reason or cause not to have more women in the future. That was very important to me.” —“Fresh Air,” March 2013

6. Amy Sherald
On the moment she was asked to paint Michelle Obama’s portrait: “I’m usually so inappropriately stoic but honestly, I thought, My mom finally has bragging rights now. My mom was born in 1930, so when I told her that I wanted to be an artist, she had no clue what that meant. My friends that I grew up with, they’re all physician’s assistants, and one friend opened up a sleep clinic. We’re 37, 38, and they’re like, “What’s Amy doing?” “Well, she’s a waitress.” So my mom was essentially ashamed! But now she has bragging rights and is really excited about it, and feels like it’s something that she accomplished as well. She was the first person I called.” —the Cut, December 2018

7. Alexandria Ocasio-Cortez
On winning her seat in Congress: “I think about oftentimes that incredible day on June 26, when — despite no attention, despite no media fanfare … we were able to organize everyday people knocking on our neighbor’s door and despite being outspent $4 million … despite the fact that I’m working class … despite all those things, we won … Today is a milestone, but it’s really a beginning … We have to keep organizing. We cannot stop. Electoral politics is just a tool in a larger tool box of this movement.” —her victory speech, November 2018

8. Olivia Wilde
On her directorial debut, Booksmart: “It is remarkable that I am 35 years old and this is the first job I’ve ever had that wasn’t entirely dependent on and connected to my looks. It grosses me out to acknowledge it, but I’ve been thinking a lot about it … [But with Booksmart,] I was there only because of my brain and my heart. And the sense of fulfillment that comes from that is really massive. It’s a profound shift for me.” —the New York Times, May 2019

9. Laverne Cox
“I was discovered on the subway. It sounds more glamorous than it was. It was for a film that I don’t think anybody has seen. The character was called ‘Drag Queen’ … she didn’t even have a name! But by the time I auditioned for Orange Is the New Black, I’d done a couple episodes of Law & Order, I’d done a guest spot on an HBO show, and I’d done several independent films. But nothing that obviously really launched me in the same way OITNB has … Producer, Emmy-nominated actress … this is all new for me. Just a few years ago, I was still struggling to pay my rent. I was thinking of going back to graduate school [for women’s studies] actually because I hadn’t had an acting role for nine months. All the success just reminds me of how far I have come and how much work is still yet to be done.” —Women’s Health, September 2015

10. Sarah Koenig
“I’m a theater nerd at heart; I’m sort of a ham, and I used to do improv comedy. I like putting on a show with a group of people. It never occurred to me that I would host my own thing until Julie sat in on an interview I did. Afterward, she squinted at me, and she was like, ‘I have an idea for you … I think you should host your own show. I think we should make a new show for you.’” —the Cut, January 2019

11. Lupita Nyong’o
On winning an Oscar for Best Supporting Actress for 12 Years a Slave: “This is not about, ‘Is this what I am or am not meant to do?’ It was really about rising to the opportunity that had been given to me and making sure I didn’t sabotage it with the fear that I felt stepping out into this big bad world. The size, the people, the history of cinema and American history — I needed to not psych myself out of it and actually do the thing that I trained for three years to do and I loved to do. The film was a utopic experience, in terms of having an incredible director, an incredible script, an incredible cast and a quite joyous set experience, despite the subject matter.” —AnOther, Spring/Summer 2019

12. Sally Rooney
On Conversations With Friends and Normal People: “It’s just such an absolutely bizarre feeling because obviously in the process of writing those books I had no identity as a writer. I was just a random person writing each sentence as I went along with no sort of structuring identity behind the construction of those stories or those sentences. And I don’t know if I will ever be able to get that feeling back now.” —the Cut, March 2019

13. Elizabeth Banks
On directing Charlie’s Angels: “The main concern I have is that it will never happen again. I feel like I’ve spoiled it for myself going forward, and, frankly, I think that’s fine. That’s my personal best. I have a friend who just ran a marathon and beat the personal best that they did when they were 19, and now they’re 46 and they just bested it by a minute. I feel like that’s how I’m gonna approach everything: I have had my personal best, and I’m going to spend the rest of my career trying to beat it.” —IndieWire, November 2019

14. Ali Wong
On her first Netflix special, Baby Cobra: “It was very much my ‘big break.’ I used to worry that nobody would come to my shows. Now I have anxiety about scalpers snatching up all the tickets because they know they can charge double on the secondary market. I wish I could jump through the internet and kick those motherfuckers in the face … The two most unexpected and exciting things that have happened since were New York Fashion Week and Halloween … I walked the runway for Opening Ceremony with Rashida Jones, Whoopi Goldberg, Natasha Lyonne, Diane Guerrero, models, and all of these other incredible women. And then in October, I was shocked at how many women and men dressed up as me, while I was pregnant and performing Baby Cobra, for Halloween. It really surprised me, and I was so touched.” —Portland Monthly, March 2017

15. Meg Ryan
When a Man Loves a Woman. It was a pretty amazing confluence of events. I was married to Dennis, and he was getting sober and this movie came along. So in real life and in the movies, I was understanding ‘What does co-dependent mean? What is alcoholism?’ I went to Al-Anon meetings. I went to AA meetings. Because I was the alcoholic in the story, it gave me empathy. It was a cathartic role.” —the New York Times, February 2019

16. Constance Wu
“When I moved to L.A. from NYC I had been a theatre actress scraping by with waitressing jobs for ten years. I expected to be doing that for the rest of my life, and I considered even that to be a privilege. Then I booked Fresh Off the Boat. It was my first-ever leading role on a TV show. It was also historic — FOTB was the first network TV show in over 20 years to center [on] an Asian American story. Suddenly, with FOTB’s success, people were talking about the lack of Asian American stories. Why had it taken 20 years? … And now history is about to be made again — in a little over a week, the Warner Bros. film Crazy Rich Asians will be released. It’s a bit of déjà vu for me, because CRA is the first Hollywood Studio film in over 25 years to center [on] an Asian American’s story. Before CRA, I hadn’t even done a tiny part in a studio film … I never dreamed I would get to star in one … because I had never seen that happen to someone who looked like me. CRA is changing that, just like FOTB did.” —Twitter, July 2018

17. Hari Nef
“I did a theater internship, and it was awful, so I tried fashion, first at VFiles and then with Jennifer Venditti, the casting director. She needed me during Fashion Week, but I was helping my friends who were designers with their shows on the side, and she could tell I was distracted, so she fired me. She probably thought I had All About Eve’d her. I also worked for Fabien Baron, the creative director, where I was known as the intern who always fell asleep at her desk. It was right around when I started hormone-replacement therapy, and I was sleepy for the first six months … I felt vulnerable about my body, so I had to kick my coping mechanisms into high gear and ask myself, ‘Are you going to be this sad little trans girl and miss out on all this stuff because you don’t like the way your body looks, or are you going to see where it goes?’ It was just about me having this instinct, not understanding what my role was or why I was put on the planet. I followed the scent of something that smelled sweet until suddenly all these things fell into place.” Time, September 2016

18. Phillipa Soo
On getting cast in Hamilton: “Tommy Kail, the director, and Lin-Manuel Miranda came to the show I was in before, which was my New York theatrical debut. It was called Natasha, Pierre & the Great Comet of 1812. That was how they were introduced to me and my work … Tommy asked me to be part of a table read for [Hamilton] Act II, because they still hadn’t heard it all in one time. So from then on, I was asked to come in and work with Tommy on some stuff, so that was kind of my audition, but it was mostly just a work session. Then they asked me to be part of the first workshop in January, the first time the whole show had been put together. I continued to work with them throughout last year, and here we are.”
Jezebel, May 2015

19. Kerry Washington
“It’s impossible to say that Olivia Pope hasn’t been one of the most transformative roles for me. I’ve never played a character for this long. Olivia Pope also took my anonymity away. Before, I was a character actor: Nobody really knew that the girl from Save the Last Dance was the same girl from The Last King of Scotland. So I could show up and be a person in the public eye when it was useful, then dip out and have my life. Olivia Pope has really changed that.” —Glamour, April 2017

20. Kristen Wiig
“It depends on how you look at it. I guess most people would think it would be Bridesmaids, and some would think it would be SNL. But I think for me I would even go back to the Groundlings Theatre in L.A. and getting into the main company, because it was the first time I had worked so hard to get this one thing and then it happened. I remember getting that phone call when I got into the main company like it was yesterday. It was the biggest, happiest moment. It’s a lot of work, and it’s years of classes and shows and writing and being vulnerable and putting yourself out there and finding characters and improvising and being nervous and it’s a whole life. When I got into the main company, that was really a big deal for me.” —IndieWire, July 2013

21. Diane von Furstenberg
On creating the wrap dress: “It’s so strange: This little dress paid all my bills, paid for my children’s education, made me famous, gave me a voice — I mean that little dress did everything for me — but for the longest time I took it for granted. I never honored it. When people said, ‘Diane von Furstenberg, the wrap dress!’ I’d say, ‘But I do other things, too.’ It was only last year, as I prepared the [“Journey of a Dress”] exhibit, that I realized how important it was.” —Oprah, December 2014

22. Lady Gaga
On her 2017 Super Bowl performance: “It was a milestone performance for me. I felt it really marked the decade of the first ten years of my career and it felt like the fans performed the Super Bowl, not me. It was really for them.” —AXS, September 2018

23. Betty White
“My big break came when a local disc jockey, Al Jarvis, in Los Angeles invited me to be his girl Friday on his talk show ‘Hollywood on Television’ — so would I be his girl Friday? Sure, Friday, that’s great. Well, what he meant and I didn’t realize was Friday, Saturday, Monday, Tuesday, Wednesday, Thursday. Five and a half hours a day, six days a week, live — whatever happened you had to handle it. There was never any rehearsal or script or anything. Whoever came in that door, it was on, and you were interviewing them.” —NPR, November 2014

24. Tig Notaro
On performing stand-up one day after her cancer diagnosis at the L.A. comedy venue Largo: “My life had fallen apart very quickly, and I knew that I was about to have surgery and go into treatment. I didn’t want to be foolish and assume that everything would be okay, so I wanted to do stand-up one last time, in case I died of cancer. I wanted to be honest about where I was and what had happened — and to see whether any of it was funny … I remember thinking when I was onstage, ‘This is maybe a really special moment in my life. This feels good.’ [The comedians watching] were all mouths agape because none of them had known what was going on. They were like, ‘What the hell just happened?!’ And then they all started tweeting.” —the Independent, August 2013

25. Dolly Parton
On receiving the 2016 Willie Nelson Lifetime Achievement Award: “It makes me feel good to feel like I’ve done something to further this business. Of course you never know what you’re gonna become or what you’re gonna achieve when you start out. But the fact that all these young women and all these young stars say I’ve inspired them, it makes me feel real good. Makes me feel like I might have done something right along the way … It makes me feel like I’m still part of things. It makes me proud.” —Rolling Stone, November 2016

25 Famous Women on Their Career Milestones