What 6 of Our Favorite Lady Boss Celebs Were Doing in Their 20s

It's not what you think

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It’s so easy to get caught up in the sparkly success of our idols. Their social media accounts are exploding, they’re overwhelmed with opportunities, and their paychecks aren’t looking too shabby either.

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Why am I not there yet? you might find yourself thinking, and it’s easy to see why. We’re constantly shown the success stories, but we rarely see the before-the-success-stories.

That’s why we’ve rounded up what your favorite boss lady celebs were up to in their 20s, and we bet it looks a lot like your current path.

Here are six amazing pieces of proof why you should keep on truckin’ and chasing those dreams.

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J.K. Rowling

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J.K. Rowling didn’t always hold the title of the first billionaire author. In her 20s, she was mourning the loss of her beloved mother and failed marriage and raising a child singlehandedly, all while living in poverty and battling depression.

But that didn’t stop her from writing. In fact, she channeled the pain of losing her mother into her first novel, Harry Potter. And get this: After a particularly horrible fight with her first then-husband Jorge, angry and frustrated she locked herself away to write for the evening. That writing session was the night she invented Quidditch.

Rowling was 31 when Harry Potter and the Sorcerer’s Stone was published, but her success never stopped her from getting real about her past.

“I have never been remotely ashamed of having been depressed. Never. What’s there to be ashamed of? I went through a really tough time and I am quite proud that I got out of that,” Rowling stated.


Oprah Winfrey

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 Oprah Winfrey is easily one of the most (if not the most) influential women in television and media. It’d be easy to get caught up in the fairytale that Oprah simply started at the top. However, we all know the entertainment business is anything but a fairytale.

Although Oprah was the first female and African American news anchor at Nashville’s WLAC-TV in her early 20s, it wasn’t all smooth sailing. In 1976, at age 22, Oprah moved to Baltimore for a gig as an anchor with WJZ-TV.

But in 1977, she was publicly fired. The Queen of TV is perfect proof that one rejection does anything but define you; she even called her time in Baltimore the “greatest growing period of my adult life.”


Tina Fey

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While Oprah was getting publicly fired at 23, Tina Fey was holding a steady job. Nope, not as a famous comedian but as an employee at the YMCA in Chicago.

“I got a day job at the Evanston YMCA, working at the front desk. I had the worst shift imaginable: 5:30 in the morning till 2 in the afternoon. But I had my nights free to take classes at Second City,” Fey recalled in 2003.


Wendy Davis

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Today, Wendy Davis is probably most well-known for her 11-hour long filibuster in Texas in 2013 (her hope was to block restrictions on abortion). But before Davis represented district 10 in the Texas Senate and before she attended law school, she was just a 20-something with big dreams in an almost-hopeless position.

At 20, Davis was a college dropout (due to financial struggles) and waiting tables at her father’s restaurant all while caring for her daughter as her divorce from her husband was finalized.

It was only up from there, however. Davis would attend Harvard Law School in 1990 and would go on to become a Texas state senator and run for Governor of Texas. Oh yeah… and fight hard for women’s reproductive rights.


Sara Blakely

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We all know the lifesaver undergarment brand Spanx, but do you know the founder’s inspirational story? At 27, Spanx founder Sara Blakely was miserable selling fax machines door-to-door, but it was the misery of that job that propelled her toward her entrepreneurial endeavors.

“I woke up one day and thought, ‘I’m in the wrong movie, call the director! What happened? This is not my life,’” she told New York magazine.

She then decided to write down the things she was good at on a piece of paper. “Sales” did make this list, but it was this journal entry that was truly the catalyst to transforming her life.

“I want to invent a product that I can sell to millions of people that will make them feel good,” she said, And with that, Spanx was soon born.


Barbara Corcoran

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Because of her dyslexia, Barbara Corcoran was labeled “stupid” early on in her life at school.

“I feel like my whole life I’ve been insecure about looking not smart,” Corcoran confessed to Entrepreneur.

But her mother didn’t see it that way; she saw a creative, street-smart woman blooming in front of her, and boy was she right.

By age 23, the Shark Tank star had already had 22 odd jobs, and she was picking up business smarts from all of them.

When she was a pigtailed waitress at 22, she met her first love, Ramon. While the relationship didn’t last, she took a $1,000 loan from her then-boyfriend who thought she’d be great at real estate, and founded her property business, The Corcoran GroupShe sold her real estate business for $70 million in 2001.

Skylar Harrison
Skylar Harrison

Skylar is both word and food obsessed and once cried over spilt guacamole. And no, she doesn't want to talk about it. Follow her at @skylarharrison.