doing the most

25 Famous Women on Making Tough Decisions

Photo-Illustration: by Stevie Remsberg; Photos: Getty

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

Having power comes with the responsibility of making high-pressure decisions under the spotlight. Below, 25 famous women, including Ellen Pao, Greta Thunberg, and Shonda Rhimes, discuss the big choices they made to kickstart a movement, take their business to the next level, or figure out the right next step in their careers.

1. Amy Poehler
“I made a decision early on that I would be a plain girl with tons of personality, and accepting it made everything a lot easier. If you are lucky, there is a moment in your life when you have some say as to what your currency is going to be. I decided early on it was not going to be my looks. I have spent a lifetime coming to terms with this idea and I would say I am about 15 to 20 percent there. Which I think is great progress … Decide what your currency is early. Let go of what you will never have. People who do this are happier and sexier.” —Yes Please, 2014

2. Nora Ephron
“Being a wuss is not part of the job description. What you do all day long on a movie set is make decisions. You make millions of decisions. Should the character wear a red shirt or a blue shirt? Should this room be 2 feet wider? Blah blah blah. Almost none of those decisions really matter. But you make all of them as if they did, as if people’s lives depended on them. The biggest surprise is that everyone told me directing was going to be the most arduous, difficult, impossible, ruinous-to-my-health, blah-blah-blah experience that I would ever go through. And nobody told me it was going to be the most fun that I would ever have.” —The Morning Call, 1992

3. Anna Wintour
“I surround myself with a talented group of people that are opinionated and interesting. I try to remain very open to what others have to say. And, obviously, in the end you make a decision, and you’re right or you’re wrong.” —Forbes, August 2011

4. Condoleezza Rice
“I think that you have to have a certain decisiveness about things. People would rather have an answer of ‘no’ than have no answer.” —Stanford Magazine, May/June 1999

5. Shonda Rhimes
“I’m in a position of power where I run this world and handle this situation … If I’m going to make a crazy decision, then I better be damn sure. Because it’s not like anybody’s going to tell me, ‘You can’t do that.’” —New York Times, May 2013

6. Lena Waithe
“Stop giving a shit what other people think of you. We make decisions too often based on that. When we start to live for ourselves, and be a little bit more selfish, I think we’ll lead more fulfilling lives. So I think what we need to do is stare at ourselves in the mirror a little bit longer, and really own who we are and not try to be what we think others want us to be.” —Variety, 2018

7. Suze Orman
“Fifteen years ago I decided that I didn’t want to live a lie anymore. I wanted to stand in my truth. I didn’t want people in my life who did not support me — emotionally, psychologically and spiritually. I only wanted people in my life who were positive influences on others and me. So at the age of 50, I decided to make a clean sweep. I took a hard look at my friends, my employees and a relationship I’d been in for eight years. In just one week, I ended a lot of relationships, cutting off some friendships I’d had for a good 15 years. And I have to tell you, it was one of the best decisions I’ve ever made. Because the true key to success, believe it or not, is to keep good company.” —Success, 2016

8. Janet Yellen
“Sometimes you have to make decisions without knowing all that you would like to know. That’s part of the job … We necessarily operate in an environment in which there’s a great deal of uncertainty. In such an environment, it makes sense to use a risk-management approach to identify and avoid the big mistakes. That’s one reason I favor a cautious approach.” —Time, April 2016

9. Christina Tosi
“The reality of the situation is that sometimes, you have to lay down the law. The way I do it involves a sense of humor! The ‘double tap’ achieves that. All you have to do is tap someone on the shoulder and let them know that what they’re doing is not cool. Sometimes, it’s a wake-up call. Our company is full of 20-, 30-, and 40-somethings that inevitably range in different emotional phases, so people don’t always have the ability to see the bigger picture. If someone is hanging out at family meal in line and there are 50 people behind them, scooping food onto their plate like they’re the last person in line, you’ve got to go up behind them, pull the ‘double tap,’ and be like ‘Bro, you know there is a family of 50 people behind you that also needs to eat today?!’ You can do it with a sense of humor, but also with a sense of authority.” —Vice Munchies, April 2015

10. Justice Sonia Sotomayor
“When the Supreme Court takes a case, it’s because there is a disagreement among the courts below… and every decision we make is final. Every time we decide, even when I’m in the majority and I think we’re right, you know that there’s a loser. There is another side who is going to feel something negative about what has happened. And that makes this job harder. Once we decide, there is no more hope.” —Spiegel, April 2014

11. J.K. Rowling
“If we make decisions in small matters in the awareness that our actions can have [a] huge impact on others, we will begin to make a difference.” —Goodreads, July 2013

12. Emily Weiss
“Just do the next right thing. Like, it’s truly a journey when you’re starting out and you’re an entrepreneur. The next right decision, every time. Just keep thinking, what’s the next right decision? And I think that helps you get somewhere, that really helps you just get some momentum and leads you in the places you’re supposed to go. Because you cannot possibly chart that journey. You just could not map it in your mind.” —Vox, January 2019

13. Ellen Pao
“[When I became the CEO of reddit], I made the executive decision to remove unauthorized nude photos, including revenge porn, and overt harassment. As a result, I received rape threats, death threats, and titles like ‘most hated person on the internet’ and ‘pariah of Silicon Valley.’ To recap: My crime was taking down stolen, vindictively posted photos of naked celebrities and regular people.” —Reset, September 2017

14. Susan Wojcicki
“One way I think about some of the decisions is putting myself in the future and thinking: in five or ten years, what will they say? If someone were to look back on the decisions that we’re making, would they feel we were on the right side of history? Would I feel proud? Will my children feel like I made good decisions?” —The New York Times, April 2019

15. Taylor Swift
“With 1989, I was really putting my neck on the line, because I was the one saying I need to change directions musically. And my label and management were the ones saying ‘Are you sure, are you positive? This is risky.’ And I was the one who had to come back every time and say, ‘No, this is what we’re doing.’ … Every single element of this album has been called into question, and I’ve had to say ‘No, this is how we’re doing it.’ And the fact that we came out and did the kind of numbers we did in the first week — you have no idea how relieved I was, because it was all on me if this didn’t work.” —Time, November 2014

16. Mary Barra 
“I try to create an environment where people feel they could voice their concerns and that we can get the best ideas on the table and then make the right decision. But at the end of the day, when the decision has to be made, if we don’t have complete unanimity, I have no qualms about making it. But I want that tension in a constructive way to make sure we evaluate things from every angle.” — The Los Angeles Times, December 2013

17. Greta Thunberg
“I became a climate activist, started to attend demonstrations and marches and join organizations and contact people within these movements. But I just felt like things were still too slow, and so I decided to try something new. And that’s when I started planning the school strike. And then I just decided to do it … My [Asperger’s] diagnosis helps me see things a bit more clearly sometimes when everyone else seems to just compromise and have this double moral that’s — yeah, that’s very important, but also, I can’t do that right now, and I’m too lazy and so on. But I can’t really do that because I want to walk the talk and to practice as I preach. So that is what I’m trying to do because if I am focused on something and if I know something and if I decide to do something, then I go all-in. And it seems like others are not doing that right now. So yeah, it has definitely helped me.” —NPR, September 2019

18. Oprah Winfrey
“The truth is, I have from the very beginning listened to my instincts. All of my best decisions in life have come because I was attuned to what really felt like the next right move for me… Align your personality with your purpose, and no one can touch you.” —Stanford Graduate School of Business, April 2014

19. Kris Jenner
“I remember when [Kim] said, ‘I want to do a fragrance.’ We made that all happen … We, together, figured out fragrance. When it came time for her to choose her bottle in the development stage, she knew the shape of the bottle, but she was stuck on the color. It was going to be a black bottle with a pink trim, and it was either dark pink or light pink. One day she just puts it up on Twitter and says, ‘Hey, guys. What do you think? This color or that color?’ I said, ‘You are a genius.’ She got such an overwhelming reaction in such a positive way. She chose the color that they wanted, and then she would have a contest and send fragrance bottles to their home because they helped her pick the color. I thought that was so remarkable. That’s really the moment that I learned boundaries about when to jump in with my kids and our businesses. Because we work together on all of the things we do, but there’s a moment when Mom has to step back. Manager has to be there, but let my daughter/client, in some cases, do her thing and not be too overbearing.” —Lenny Letter, August 2017

20. Jessica Alba
On leading The Honest Company: “There needs to be a process for who should be in the room when a decision is made. Every department needs a seat at the table. You have to think about what’s the tail of this decision, not just the head of the decision.” —Inc.

21. Madeleine Albright
On making decisions as Secretary of State: “The minute I was named, I called all my predecessors … we talked on a regular basis and I considered that very important. I had them each individually to the State Department for lunch and we’d go through things. I’d call them before any particular decision was made, which my successors have not always done, by the way.” —Edward M. Kennedy Institute

22. Michelle Obama
“Don’t ever make decisions based on fear. Make decisions based on hope and possibility. Make decisions based on what should happen, not what shouldn’t.” —Campaigning in Phoenix, 2011

23. Sheryl Sandberg
“I truly believe that the single most important career decision that a woman makes is whether she will have a life partner and who that partner is…I don’t know of one woman in a leadership position whose life partner is not fully — and I mean fully — supportive of her career.” —Lean In

24. Arianna Huffington
“The best decision I ever made was committing to getting eight hours of sleep a night. For many years I subscribed to a very flawed definition of success, buying into our collective delusion that burnout is the necessary price we must pay for success. Then in 2007, I had a painful wakeup call: I fainted from sleep-deprivation and exhaustion, hit my head on my desk, and broke my cheekbone. From that point on, I knew I had to make sleep a priority … Now, 95 percent of the time I get eight hours of sleep a night. Once I started giving sleep the respect it deserves, my life improved in pretty much every way. Now, instead of waking up to the sense that I have to trudge through activities, I wake up feeling joyful about the day’s possibilities. I’m also better able to recognize red flags and rebound from setbacks. It’s like being dialed into a different channel that has less static.” —The Sleep Revolution, 2016

25. Senator Kirsten Gillibrand
“I take calculated risks. I measure. I assess risk very intensely. And then I make a judgment. When you play tennis as a kid, you’re going to win sometimes and lose sometimes, and you learn how to behave well under both circumstances. Such a great life lesson because if you’re not afraid of losing, you’ll take a risk — like running for office. Even though it’s a two-to-one Republican district. Even though I might get battered and bruised. I’ll run even if no one thinks I can win except for my mother.” —Vogue, November 2017

25 Famous Women on Making Tough Choices