Famous Female "Failures"

May 7, 2018

Some of the most inspirational women of our time have experienced failure in one way or another and went on to be huge successes in their chosen fields. 


Many have openly shared their stories to inspire us to never be afraid of failure but to see it as a “stepping stone to success,” as Arianna Huffington’s mother described it. 


We invite you to draw inspiration from some of our favourite, yet very surprising, world-class “failures”.


Oprah Winfrey


Our favourite “Queen O” may be a media icon and super successful businesswoman now, but her journey has been a rollercoaster peppered with failures.


In her first television job on Baltimore’s WJZ, she experienced regular humiliation and sexual harassment before being fired and accused of the show failing because of her involvement rather than her old white male cohost. 


“Not all my memories of Baltimore are fond ones,” she told The Baltimore Sun in a 2012 interview. “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.”


Rather than let the situation get the better of her, she used the experience to hone in on her skills and her passions and went on to become a household name, continually learning along the way. 


Years later when Oprah decided to bid farewell to The Oprah Winfrey Show after sitting in the number 1 spot for 21 years, she launched OWN - the Oprah Winfrey Network. One year after its launch, nearly every source of media proclaimed she had failed. 


In her Harvard University commencement speech, Oprah said, “I can still remember the day I opened up USA Today and read the headline, ‘Oprah: Not Quite Standing On Her OWN’. It really was the worst period in my professional life. I was stressed and I was frustrated, and quite frankly, I was embarrassed…Then the words came to me…This too shall pass. And I thought, I am going to turn this thing around and I will be better for it. And I am here to tell you that I have turned that network around."


J.K. Rowling


One of the best selling authors of our time, J.K. Rowling was rejected left, right and centre before she finally got published. 


Writing the book that essentially made her a household name was no easy journey either. The idea was conceived years before it was finally written, but life took hold and Rowling had no choice but to hold on for the bumpy ride. 


Her mother passed away which plunged Rowling into a deep depression she pulled herself out of by travelling to Portugal and teaching English for a year. Where she was hoping to have the book finished before returning to the U.K. she ended up falling in and out of love very quickly, resulting in a failed marriage and her new role as single mother to her baby daughter. 


She was jobless, “as poor as it was possible to be in modern Britain without being homeless”. “By every usual standard, I was the biggest failure I knew,” Rowling told the audience as part of her Harvard commencement speech. 


So she sought solace in writing until the book she had conceived years before was well on its way to being finished. 


The journey from here wasn’t an easy one either though, Harry Potter was rejected by publisher after publisher - we bet they’re kicking themselves now! 


It wasn’t until the editor at Bloomsbury Publishing and their 8-year old daughter read the manuscript that success seemed possible. 


She became the first female to become a billionaire as an author. 


“It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all - in which case, you fail by default.” 



Anna Wintour


The devil may wear Prada but it certainly didn’t start off wearing it. Anna Wintour was sacked from her position as junior editor for Harper’s Bazaar in 1975 because her photo shoots were too edgy. 


Rather than let that shift her beliefs or passion, she went on to become one of the most successful women in fashion. 


“Everyone should be sacked at least once in their career because perfection doesn’t exist. It’s important to have setbacks because that is the reality of life,” Wintour is quoted as saying in Alastair Campbell’s books Winners: And How They Succeed.




The original “Material Girl” initially headed to New York City to follow her dreams of being a dancer and only turned to music when that dream didn’t work out. 


She faced rejection after rejection including one from the Millennium Records President   Jimmy Ienner who was keen to see some more from the fledgling artist but not ready to commit. Click here for his rejection letter that is now famous. 


Madonna didn’t let rejection stop her and is now a music icon. 


Vera Wang


Renowned fashion designer Vera Wang did not dream of creating dresses that celebrities fawn all over. Her passion was the ice.


She wanted to be a professional figure skater but didn’t make the U.S. Olympic team in 1986 and, as a result, started working at an Yves Saint Laurent boutique in New York City before starting a role at Vogue soon after. 


“When you fall down - which you have to if you want to be a skater - you pick yourself right up and start again. You don’t let anything deter you,” Wang said in an interview with Business of Fashion in 2013. 


Ellen DeGeneres


The woman who spreads a little love and laughter to millions every day through her talk-show, was fired for being gay in 1998.


When she made the decision for herself and her character to come out on her sitcom Ellen, the move sparked much controversy. Companies including JC Penney and Chrysler who were clamouring to advertise before the episode aired, withdrew their support following pressure from the American Family Association. As a result, the comedian found herself out of work and facing rejection after rejection until she landed her daytime television gig in 2003. 


She told the audience of The Ellen Show in 2016, “I lost everything. But look at me now! I could buy that Governor’s mansion, flip it and make a $7-million profit. There’s already so much inequality in the world - women’s rights, gender-pay gap, racism. I think we need to remember that we are more similar than we are different.”


Click here for our 5-steps to help you overcome failure. 


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