"I Was Scared of Everything": Celebs on Their 20s

Updated 05/15/18

Your 20s can be an incredibly daunting time. Whether you're at school or you're in the workforce (or both), there's a lot of pressure to do something incredible with your life. But if you don't become a millionaire before you're 30, don't stress, because if the success stories of some of the world's most talented women are anything to go by, your 20s are when you create those career-changing building blocks.

If there is one thing we've learned, it's that success takes perseverance, grit, and time, so have patience—these wildly successful women will show you how to hustle. Ahead, be inspired by some of our favorite leading ladies who prove that what you do in your 20s matters, but it doesn't always look like you imagined it would. Here are 10 things to do in your 20s, according to some of the most successful women in the world right now.

Kerry Washington

Kerry Washington
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Before she was Olivia Pope, leading lady of the hit Shonda Rhimes political drama Scandal, Kerry Washington was a regular girl from the Bronx. Although she trained in theater in her youth, Washington attended George Washington University in her early 20s studying sociology and anthropology.

Despite earning a degree in social sciences, Washington grew into her career working as a character actor and picking up smaller roles in a variety of films and TV shows during her 20s. You may have spotted her in Save the Last Dance or a few old episodes of Law & Order. Regardless of these humble beginnings, Washington persevered, finding what she calls "one of the most transformative roles" of her life as Olivia Pope at age 35, she tells Glamour.

Now, with Scandal coming to an end and a growing family of her own, Washington is sure that things are only going up from here. "Life is just getting better," she says. "For me, 40 feels like a beginning. I'm in the middle of so much new—with this career, the kids, and I'm still sort of a newlywed. I'm excited to be at this stage in life."

The Takeaway: Take your time. Success isn't always instantaneous. Keep hitting the pavement in your 20s to build your way up to future accomplishments.

Tina Fey

Tina Fey
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Opportunity comes when you least expect it, and in varying forms—just ask Tina Fey. The wildly successful actress, comedian, writer, and producer is one of the greatest of our generation, yet she started out just like us, working part-time jobs to make ends meet. In fact, the actress wrote in her book, Bossypants, that her life-changing moment was getting a job that barely paid anything.

After graduating from the University of Virginia, Fey landed a gig at an improv and sketch comedy theater called The Second City in Chicago. "I moved to Chicago in 1992 to study improv and it was everything I wanted it to be," she writes. "It was like a cult. People ate, slept, and definitely drank improv. They worked at crappy day jobs just to hand over their money for improv classes." Fey toured the country with this company and was paid just $75 a show and $25 per diem, which wasn't always a guarantee either.

"Of course, sometimes you'd have a show in Kansas, so you'd have to ride in the van for two days to get to your seventy-five-dollar gig," she writes. "It wasn't lucrative, but it was show business!" And despite the pay, Fey told NBC News that The Second City was the best job she ever had. By age 27, she was eventually hired at Saturday Night Live and promoted to head writer just two years later, a female first.

The Takeaway: Accept that making good money isn't always possible early on in your career, but if you follow your ambitions, you never know what the future will hold.

Gwyneth Paltrow

Gwyneth Paltrow
Eric Ray Davidson / Trunk Archive

Gwyneth Paltrow is an Academy Award-winning actress, popular author, and CEO of the lifestyle and e-commerce site Goop. But before she hit her stride, Paltrow had to "scrounge quarters to buy Starbucks." Paltrow told her father she was going to quit UC Santa Barbara to "try to be an actress," and he did what most parents would: He supported her decision and then made her do it on her own.

She told Glamour, "My dad was like, 'That's great, but I'm not gonna help you.' I was like, 'Yeah, right.' And he was like, 'No, I'm not.' So I got an apartment with a roommate; I worked as a hostess at a restaurant; I would scrounge quarters to buy Starbucks—and walk there to save gas. I remember once asking my dad for money, like, 'Please, I'm really stuck. Can you help?' And he said, 'You're more than welcome to come over for dinner.' That was it."

Thankfully her career took off by the time she was 26, but despite an Oscar for her role in Shakespeare in Love and major roles such as Pepper Potts in the Iron Man movies, Paltrow's father was there to bring her back down to earth, which she credits for changing her life. "I remember my dad once sat me down when I was 25 or 26," she told Glamour. "I was in the middle of this storm of success, and my dad was like, 'You're getting weird.' [Laughs.] I was like, 'Oh my god, I am. Oh, sh*t.' I mean, I got it. I thought I was so awesome for a minute. He was like, 'Let's stop this bullsh*t now.' I was like, 'Oops.'"

The Takeaway: Follow your gut. Sometimes you take an unexpected path to achieve your dreams.

Mindy Kaling

Mindy Kaling
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Even in her early 20s, Mindy Kaling was a force to be reckoned with. She studied theater and playwriting at the elite Dartmouth College and landed her first major gig as a writer on a little comedy called The Office at the tender age of 24. This, of course, was after a few years of working as a babysitter and production assistant in New York City, practically prerequisites for most people hoping to make it in the entertainment industry. According to Vulture, during this time she applied to the NBC Page Program but didn't land the job. It was a play Kaling wrote called Matt & Ben (which poked fun a Matt Damon and Ben Affleck) that really kick-started the comedian's career and led her to her work on The Office and, later, her own TV show, The Mindy Project.

While she faced some failures early on in her career, it's clear she hustled in her 20s to get where she is today. "I was freakin' Jaws in a community swimming pool. I wrote plays, I acted, I sang, I was the student newspaper cartoonist," she writes in Is Everyone Hanging Out Without Me? Getting involved and pursuing your passion—these are the things to do in your 20s to be successful.

The Takeaway: Start early. If you know you want to do something, get involved in any way you can.

Diane von Furstenberg

Diane von Furstenberg
Jennifer Livingston / Trunk Archive

From the beginning, Diane von Furstenberg was an independent, free, and self-reliant woman, traits she credits to her mother and which steered her course for success early on. But it was when a friend invited her to a party in Gstaad, Switzerland, from boarding school that changed the course of her life. There, she met her future husband, Prince Egon von Fürstenberg, whom she subsequently married in 1969 and gave birth to their first child together just a year later at age 24. They had their second just a year later. During this time, Egon introduced her to Angelo Ferretti, an Italian scarf manufacturer who produced the designer's famous jersey dresses.

Despite being a European princess living in New York and a regular fixture at Studio 54, von Furstenberg says she was still intimidated when she first met iconic Vogue editor Diana Vreeland to present her range of jersey dresses. "What I'm fascinated by is the beginning of your adult life, somewhere between 19 and 25," she told The Daily Beast. "You have all of these doors in front of you, and you don't know which door is going to be the important one. How would I have known that Angelo Ferretti was going to be such an important person in my life? And that's life—that's just it!"

The Takeaway: Be open to anything and everything. You never know when the most important moment of your life is going to happen.

Hilary Swank

Hilary Swank
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It's hard to forget Hilary Swank's powerful and haunting performance in Boys Don't Cry, yet despite winning the Academy Award for Best Actress after this film, she barely had enough money to live on—or health insurance. Of course, her success after this movie has made her a household name, but Swank was an unknown actress before filming began.

"I ended up dropping out of high school. I'm a high school dropout, which I'm not proud to say," she told CBS News. "I had some teachers that I still think of fondly and were amazing to me. But I had other teachers who said, 'You know what? This dream of yours is a hobby. When are you going to give it up?' I had teachers who I could tell didn't want to be there. And I just couldn't get inspired by someone who didn't want to be there."

So when Swank was 15, her mother packed everything and moved to California with $75 and a Mobil card. They shacked up in their car for a couple of weeks before Swank landed her first role in Beverly Hills, 90210 at age 23. She was "fired" from the show soon after, but this turned out to be a significant turning point in her career. Swank was quickly offered the lead in Boys Don't Cry, which paid a mere $75 a day, so just $3000 for the film.

This didn't matter much to Hilary, who was just happy to be working in the craft that she loved. "My mom said to me that I could do anything I wanted in life. As long as I worked hard enough," she adds. "And to this day, it still makes me really emotional, because I just never questioned it, you know? She just always believed in me."

The Takeaway: Focus on your passions, not the money. When it's right, the two will align eventually.

Rashida Jones

Rashida Jones
Pamela Hanson /Trunk Archive

When you have Peggy Lipton and Quincy Jones for parents and grew up playing with Kim Kardashian West and Paris Hilton, you'd be forgiven for thinking that Rashida Jones was fed with a silver spoon, but despite her upbringing, her 20s were spent battling ancient social stereotypes and racism. "When I audition for white roles, I'm told I'm 'too exotic,'" she told Glamour in 2005. "When I go up for black roles, I'm told I'm 'too light.' I've lost a lot of jobs, looking the way I do."

Her experience at Harvard was life-changing because, despite the difficulty she experienced, it helped shape her future confidence and identity. "Harvard was supposed to be the most enlightened place in America, but that's where I encountered something I'd never found in L.A.: segregation," she adds. "I had to choose one thing to be: black or white. I chose black." She credits her older sister Kidada for helping her persist. "Toughing it out when you don't fit in: That was the strength my sister gave me," she said.

The Takeaway: Be yourself, even when it seems like it might be easier to be someone else.

Kristen Wiig

Kristen Wiig
Derek Kettela /Trunk Archive

Before you were crying with laughter at her character Gilly on Saturday Night Live or during her hit comedy Bridesmaids, Kristen Wiig spent her 20s working numerous odd jobs to pay the bills. It was only by chance that she came into acting. She majored in studio arts at the University of Arizona and took an acting class to "fill a requirement" when the teacher told her she should continue acting. "I was like: What? No—I'm … No. It didn't even cross my mind," she told The New York Times.

Wiig eventually dropped out of school in her early 20s and moved to Los Angeles to try it out. That's when she spent the next decade working various part-time jobs, from folding clothes at Anthropologie to selling peaches at a farmer's market, trying her hand at floral design, selling hot dogs at the mall, and even babysitting—which is actually a pretty lucrative side hustle these days. It wasn't until her 30s that she finally scored a full-time role on Saturday Night Live.

The Takeaway: Don't be afraid to give up the career path you thought you wanted for something new. It just might be the best decision you ever make.

Reese Witherspoon

Reese Witherspoon
Thomas Whiteside /Trunk Archive

She is a bright, talented, and successful woman in her early 40s, but Reese Witherspoon told Harper's Bazaar she was "scared of everything" in her 20s. The A-list actor met her first husband, actor Ryan Phillippe, at age 21; had their first daughter at 23; and released her three biggest films during her 20s, but despite her success, she was terrified and unable to enjoy really it. "I'm much more open now," she said. "In my 20s, I was scared of everything. I didn't know what my career was. I didn't know why people liked my movies. I was wary of interacting with people. I was 25 when Legally Blonde came out, 26 for Sweet Home Alabama, and 29 for Walk the Line. And I was scared, really scared. Now I feel like a different person. It's a great thing getting older. You are who you are; you say what you mean. I kind of enjoy that!" Turns out fear was a driving force behind Witherspoon's success, with notable films under her belt; a production company, Type A Films; and a major home and clothing line, Draper James.

The Takeaway: Don't be afraid of success. Enjoy it when you experience it, even early in your career.

Busy Philipps

Busy Philipps
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Busy Philipps has been in the spotlight since she was 20 years old playing the spunky Kim Kelly on Freak and Geeks. Her early 20s were defined by this short-lived series and the teen drama Dawson's Creek in which she played the fun-loving Audrey Liddell. Philipps experienced a lot of success early on in her career, but she wasn't always confident about her work. "I had a lot of anxiety that things weren't going to work out and I didn't trust in myself enough," she tells Huffington Post. She attributes this fear for her determined work ethic. "It took me a long time to understand, especially in the work that I do, that when doors close, windows open… You just have to find your place."

The Takeaway: Trust that you're on the right path, even when doubts start to creep in.

Read up on Success:

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Fooled by Randomness by Nassim Nicholas Taleb
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This post was originally published on November 15, 2016, and has since been updated.

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