7 Famous People Who Failed Countless Times Before Realizing Their Dreams

Even Oprah knows what it feels like to get fired.

By Sharon Lynn Pruitt

Think it's a straight shot to the top? Think again. Oftentimes the road to fulfilling your dreams is filled with plenty of twists and turns, not to mention an abundance of failures both big and small. Oxygen is premiering Quit Your Day Job on Wed., March 30 at 10/9c, and we were inspired by the entrepreneurs on the show who are chasing their dreams to put together this list. Even celebs like Katy Perry and Lady Gaga had to fall a few times before they could get up, stronger than ever. Here are 7 superstars to take inspiration from the next time you feel like giving up on your dreams.

1. . Oprah Winfrey

It may be hard to picture Oprah as anything other than the icon we know her as today, but before she was the queen of daytime television, she was a young broadcast journalist out there trying to make a name for herself. One of Oprah's first jobs was as an evening news anchor in Baltimore, an experience she's described as being full of humiliation, embarrassment, and sexual harassment. As if that wasn't bad enough, she was fired after only a few months for getting "too emotionally invested" in her stories, and was demoted to a daytime talk show position. From there, she moved to another morning show in Illinois, and within months AM Chicago became the highest-rated local talk show in the city. What started out as a setback essentially became the first brick in the building of Oprah's media empire.

2. . Jay Z

Believe it or not, there was a time in Jay Z's life when he did have 99 problems, and getting people to care about his music was all of them. Back when the rapper was still living in the projects of Brooklyn, he couldn't get any record labels to give him a second look, and struggled to get his music out to the people. He sold his first CDs out of the trunk of his friend's car. All that hustling definitely paid off though, big time - the rapper/entrepreneur has a net worth in the hundred millions. He's also married to Beyonce, and if that isn't the epitome of success, I don't know what is.

3. . Vera Wang

How's this for unexpected? Vera Wang was initially poised to be a superstar figure skater. She started skating at the age of 8, and was even featured in Sports Illustrated in the late '60s. It wasn't until she failed to make the US Olympics team that she explored other options. She first entered the fashion world on the editorial side, eventually landing a job as an editor at Vogue. After she lost out on the Editor-in-Chief position, she took a job with Ralph Lauren as design director, and later became one of the most well known fashion designers in the country. Though she's perhaps most well-known for her wedding gowns, in a nod to her athletic roots she's designed costumes for figure skaters like Nancy Carrigan and Michelle Kwan.



4. . Katy Perry

Katy Perry is no stranger to struggle. The daughter of pastors, Katy grew up singing in church and as a teenager, started her career as a gospel singer. Her first album sold only 200 copies, and she switched over to secular music shortly thereafter. She moved to L.A. when she was only 17-years-old, where she signed with and was later dropped by three different labels. It wasn't until she released her hit single "I Kissed A Girl" that her career finally took a positive turn. Today, she continues to be one of the top-earning women in music, having sold over 11 million albums worldwide.

5. . J.K. Rowling

If ever you need proof that magic is real, then look no further than the life story of Harry Potter author J.K. Rowling. Before the world became enraptured by her tales of a courageous boy wizard, Rowling was a divorced single mother, struggling to make ends meet and depending on government support to survive. Throughout it all, she continued to work on the idea for Harry Potter, which she says appeared "fully formed" in her head during a train ride. Once she finished Harry Potter and the Philosopher's Stone, it was rejected by 12 publishers before finally getting accepted by Bloomsbury. Even though only 1000 copies were printed in that first run, it wasn't long before Harry Potter mania swept across the world, making Rowling one of the richest women in the world.

6. . Lady Gaga

Lady Gaga is pretty much a pop icon at this point, but things weren't always so rosy for Stefani Germanotta. She grew up writing music and performing and as an adult, even fronted her own band - the Stefani Germanotta band - while living in NYC. After the group disbanded, Gaga went to work harder on her own music, eventually getting signed by Def Jam but then getting dropped after only 3 months. She was devastated, and began experimenting with drugs while working as a go-go dancer. She was later hired as a songwriter for Sony, and it was during her time there that Akon took an interest in her, helping her sign a joint deal with his label and Interscope. She released her debut album, The Fame, in 2008, and the rest is music history.

7. . Kerry Washington

Most people wouldn't associate Kerry Washington with failure, but even she knows what it's like to get the boot by your boss. "Before Scandal, the only other two pilots I'd ever done were shows that got picked up, but I got fired," Washington told The Hollywood Reporter. "They recast my character on both shows."
Well, the joke's on them: after being cast in the starring role on Scandal, Washington became the first African American woman to star in a network primetime drama since 1974. After debuting in 2012, the show became a commercial and critical success, and made Washington a household name.


Four investors turn big ideas into big business on Oxygen’s new docuseriesQuit Your Day Jobpremiering Wed., March 30 at 10/9c. 

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