No one wants to fail. But as women, we have particular reasons to fear it. Research shows that if we do mess up, we're judged more harshly than our men in our positions would be, which leads us to take fewer risks, put ourselves forward for fewer opportunities, and play it safer when it comes to our lives and careers. According to Linda Kramer Jenning, who has written on this topic, “as a result of [this scrutiny], some women may not seize leadership opportunities, and that worries those committed to achieving gender equity.”
While it’s natural to fear failure—nobody likes screwing up—we have to stop letting it get in the way of taking chances. Take it from the incredibly successful women on this list, who yes, have all failed at one point in their career. Even Oprah, even Beyoncé! But what sets them apart is they didn’t let their mistakes keep them down—instead it fueled them to keep going. Let their stories inspire you to do the same.
Serena Williams
Williams is the GOAT. She's won a record 23 Grand Slam singles titles—including winning the Australian Open while pregnant—and still makes time to be an entrepreneur and fashion designer. But that doesn't mean she's never suffered a loss. Take the 2018 U.S. Open final, which she lost to relative newcomer Naomi Osaka. While it was visibly hard on Williams, she knows that being the best at what you do is not just about the victories. It's also about the failures. Williams once told The National, “I really think a champion is defined not by their wins but by how they can recover when they fall. I have fallen several times. Each time I just get up and dust myself off and I pray, and I’m able to do better or I’m able to get back to the level that I want to be on.”
Blake Lively
In 2015, Lively's lifestyle website, Preserve, closed up shop, a move many viewed as a failure—but the actress rightfully saw it as a learning experience. Lively openly admitted to Vogue that Preserve wasn't as "true and impactful" as she knew it could be. The experience showed that not all experiments need to be pursued at all costs. "I know what it'll look like, what I'm facing publicly, that people are just going to have a heyday with this," Lively said. "But it's so much worse to continue to put something out there—to ask my team to put something out there—that isn't the best we can do. I'm going to take this hit, and the only way I can prove all the negative reactions wrong is to come back with a plan that will rock people.'" And she's doing just that right now. (No, Preserve isn't back, but Lively is a bonafide lifestyle icon all on her own.)
Oprah Winfrey
Winfrey is the undisputed queen of media, but the come-up wasn't without its obstacles. In a 2012 interview with The Baltimore Sun, Winfrey opened up about her grueling first job at Baltimore's WJZ television station, where she experienced routine humiliation and sexual harassment—and was eventually fired. "Not all my memories of Baltimore are fond ones," she told the newspaper. "But I do have fond memories of Baltimore because it grew me into a real woman. I came in naive, unskilled, not really knowing anything about the business—or about life. And Baltimore grew me up."
Amy Poehler
You'd be hard-pressed to find someone funnier than Poehler. She made us laugh for seven season as Leslie Knope on Parks and Recreation, and before that she brought down the house on Saturday Night Live alongside longtime collaborator Tina Fey. But even Poehler has bombed. She told Fast Company, “I’ve failed a million times on stage, just not getting laughs. I’ve listened to notes that I knew weren’t right. I’ve pitched ideas and let other people change them, knowing that it was the wrong choice. The question you have to ask yourself is: How do you want to fail? Do you want to fail in a way that feels like it respects your tastes and value system?”
Vera Wang
Wang is one of the world's most visible designers, but fashion wasn't her original dream. Wang wanted to be a professional figure skater, but she didn't make the U.S. Olympics team in 1986. It was only then that she snagged a retail job at a Yves Saint Laurent boutique in New York City and found herself at Vogue two years later. Failure is at the root of her fashion empire. “When you fall down—which you have to [do] if you want to learn to be a skater—you pick yourself right up and start again," Wang told Business of Fashion in 2013. "You don’t let anything deter you."
Beyoncé
I'm sorry to break it to the Beyhive, but even someone as truly flawless as Queen B has failed. Back when she was just 12 years old, Beyoncé was part of a group called Girls Tyme that performed on a 1993 episode of the talent TV show Star Search, and she≥LOST. (Cue the horror.) But in true Bey fashion, she turned the lemons into lemonade. Of the experience she's said, "At that time, you don’t realize that you could work superhard and give everything you have—and lose.” She added, “You’re never too good to lose; you’re never too big to lose.”
Anna Wintour
The legendary Vogue editor-in-chief is one of the most successful people in the fashion industry, but even she has endured failure. In 1975, Wintour was fired from her junior editor position at Harper's Bazaar because her photo shoots were deemed too edgy—a dismissal that she's grateful for to this day. "Everyone should be sacked at least once in their career because perfection doesn't exist," Wintour said to author Alastair Campbell for his 2015 book, Winners: And How They Succeed. "It's important to have setbacks because that is the reality of life."
Kerry Washington
During a roundtable discussion with The Hollywood Reporter in 2013, Washington revealed that she had been a part of two pilots before Scandal—the shows were picked up but she was replaced. Washington went on to find success as D.C.'s political maestro Olivia Pope, but those two failures caused her a great deal of heartache—and motivation. "When you look back, don't you feel like there is a logic to how things have fallen into place?" Washington said. "Like, if only I could have known then what I know now, I would have cried a lot less!"
Lady Gaga
Gaga is a supremely talented musician and likely soon-to-be EGOT, so it's bizarre to think a record label actually dumped her—but it happened. Yes, Gaga was first signed to Island Def Jam Records in September 2006, but she was dropped after only three months—a move L.A. Reid, who helmed IDJ at the time, regrets to this day. "I made the foolish mistake of letting [Gaga] go," Reid told Larry King in 2016. Gaga persisted and eventually found earth-shattering success at Interscope Records. That early failure served as her motivation. "I remember when I got dropped from my first record label. I just said, 'Mommy, let's go see Grandma,'" Gaga told MTV in 2011. "And I cried on my grandmother's couch. She looked at me, and she goes, 'I'm going to let you cry for the rest of the day, and then you have to stop crying, and you have to go kick some ass.'"
Tina Fey
You may know Tina Fey as the hilariously awkward Liz Lemon on 30 Rock or the nerdy Ms. Norbury in Mean Girls, or from her killer impersonation of Sarah Palin on Saturday Night Live. But before she was slaying these iconic roles, she had some comedy growing pains. Fey opened up about it in Seventeen: "For my first show at SNL, I wrote a Bill Clinton sketch, and during our read-through, it wasn’t getting any laughs. This weight of embarrassment came over me, and I felt like I was sweating from my spine out. But I realized, ‘Okay that happened, and I did not die.’ You’ve got to experience failure to understand that you can survive it." She stayed on SNL for nine years and has made time for the show six times during breaks from starring in blockbuster comedies.
Reese Witherspoon
Witherspoon—and the characters she's famous for—are known for their successes, not their failures. Did Big Little Lies' Madeline Mackenzie back down when the town didn't want her to put on a production of Avenue Q? I don't think so. She fought back and brought that show to the stage. IRL, Witherspoon is just as much of an inspiration. In addition to her acting career, she runs the production company Hello Sunshine, which specializes in telling women's stories. But even with her wildly impressive track record, Witherspoon still knows the importance of failure. She told Marie Claire, “I definitely think failure is important. It’s a big aspect of becoming successful. If you're not failing, you’re really not learning." Take it from Witherspoon, it's all just part of the learning process.
Tiffany Haddish
Haddish kicked off 2019 with a failure. On New Year's Eve she performed a stand-up show in Miami that didn't live up to the standards we hold for the comedy queen. To make matters worse, people actually walked out of the show. News of the lackluster performance then went viral and Haddish issued an apology. She tweeted, "Yes this happened. I wish it was better Miami. I prayed on it and I have a strong feeling this will never happened again." Then something surprising happened—the Internet rallied around her. One Twitter user wrote, "We have to do better. Tiffany Haddish had a bad night in Miami and people are trashing her. How many of us had bad days at work and didn’t get fired? I’ll wait…" Fellow comedian Kathy Griffin posted, "This is the price of fame when you're a comic. I was so lucky that there wasn't a Snapchat/IG when I was starting out on my first big tour. No REAL comic never bombs. You are a hilarious, incredible talent @TiffanyHaddish and I can't wait to see you live! Ignore the haters!"
Remember: A million people have failed before you, and another million will after. All you have to do is keep trying.
