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57 Famous Failures That Will Motivate You to Keep Going

Winston Churchill once said, “Success is not final, failure is not fatal: is it the courage to continue that counts.” If that’s not encouragement enough to strive for your dreams, what else is?

It just so happens that the wise Winston Churchill appears on my list of famous failures. Though he ended up one of the most successful politicians ever, he pushed through many failures. 

Failure is a part of life, and it is natural to want to quit after failing. However, the following list of famous entrepreneurs, singers, athletes, and other celebrities experienced crushing failures in their lives. 

As you will soon see, and as Churchill famously said, failure is not the end of the line. It matters a great deal what you do following a failure, and those actions could change your life forever. These famous failures were able to pick back up and reach success – and you can, too. 

World’s Most Famous Failures

Some of the world’s most popular celebrities and famous figures experienced some of the most disheartening failures. Many of them saw rejection after rejection, bankruptcy, failed businesses, and even homelessness and poverty. 

Below, you might be surprised to see some very recognizable names, from Jay-Z and Beyonce to Bill Gates and Oprah Winfrey. Even renowned individuals in history, such as Abraham Lincoln and Vincent Vangogh, went through many trials and tribulations, despite their notoriety today. 

Without further ado, let’s get into these famous failures and see how their life was ultimately a success, despite their greatest downfalls. 

1. Bill Gates 

Bill Gates’s first business venture was a hardware device that failed to work when it came time to demonstrate to a potential investor. It wasn’t until after he decided to drop out of Harvard and establish Microsoft that he saw fame, success, and lots of money. 

2. Oprah Winfrey

Oprah Winfrey experienced a rough childhood, including teen pregnancy and a miscarriage, before being told she was unfit for television news. She is now worth about $4 billion, is one of the top 500 wealthiest people globally, and owns her own television network, OWN. 

3. Abraham Lincoln

Before the 16th President of the United States was elected to the highest office in the land, he lost his job, the bid for State Legislature, the bid for Speaker in the Illinois House, and the bid for Commissioner of the General Land Office in D.C. It wasn’t for another 20+ years that he would become President. 

4. Jack London

Jack London had a rough start in life with two estranged parents and several failed attempts at publishing his writing. Even after he began publishing stories in the newspaper, it still took him a few years before he finally published one of his greatest works, “The Call of the Wild.” 

5. Katy Perry

The international pop star struggled to find her place in the music industry early on, having been signed and ultimately dropped by three different labels. It turns out the fourth one was the charm, as she released her hit “I Kissed a Girl,” and her career skyrocketed from there.

6. Albert Einstein

Albert Einstein was a failure all his life: he did not speak until the age of five, he failed his exams for Polytechnic school, and he almost dropped out of university. But we know his work later led to the theory of relativity, quantum theory, and a Nobel Prize. 

7. Milton Hershey

After being fired from his first job at the age of 14, Milton Hershey later experienced his first failed business venture when he was unsuccessful selling candies on the streets of New York City. He later moved back to his family’s farm, learn how to make chocolate, and established his empire Hershey Chocolate Company at the late age of 43. 

8. Michael Jordan

Many fans know the story – Michael Jordan was passed up early on for his high school’s varsity basketball team. He pushed and improved his skills, signing with the NBA at age 21 and becoming one of the sport’s best-ever players. 

9. Steven Spielberg

Not only was Steven Spielberg rejected from film school in California, but he also saw film flops early on in his career. Even after his major failures, he became an American Academy Award-winning director with huge blockbusters such as E.T., Jaws, and Jurassic Park under his belt.   

10. Robert T. Kiyosaki 

Robert T. Kiyosaki saw many setbacks in his career, which eventually led him to bankruptcy – not once, but twice. However, he rose to the occasion, started a financial education company, sold it successfully, and began an impressive investing and writing career. 

11. Winston Churchill

A Prime Minister of the U.K. in the early 1950s, Winston Churchill, is known for his many famous quotes about failure. When applying to the Royal Military College, he failed twice before getting in and lost five total elections throughout his political career before success. 

12. Vincent Vangogh

For most of his life, Vincent Vangogh considered himself a failure since he only sold one painting before sadly committing suicide. It wasn’t until after his death that his life story saw fame and success, and he became one of the most influential painters in modern history. 

13. Jim Carrey

The Canadian-born actor Jim Carrey grew up in poverty and began his career completely failing on stage during standup routines. He continually pursued acting and finally got his big break in “Ace Ventura” at the age of 32. 

14. Dr. Seuss

Dr. Seuss, formally Theodor Suess Geisel, abandoned a Ph.D. to pursue a career in drawing. His first-ever manuscript was rejected 28 times before Random House accepted it, and at the time of his death, he had sold over 600 million copies of his now famously silly books. 

15. Curtis Jackson (50 Cent)

Curtis Jackson, better known by his stage name 50 Cent, had a rough start in life that included losing his parents, jail time, and almost dying after being shot nine times. He was blacklisted by the recording industry before Eminem signed him to his label, and he released his now 6-times platinum album. 

16. Beyonce Knowles

Queen Bee herself was disappointed at a young age when her all-girl group Girl’s Tyme lost on Star Search. The group, which later became Destiny’s Child, saw many member changes and struggles before they ultimately found success, and Beyonce found her solo career. 

17. Colonel Harland Sanders

Colonel Harland Sanders, the founder of Kentucky Fried Chicken, was forced to take care of his family at the young age of 7, left home at 14, struggled to get things started for himself. He saw his motel and restaurant burn down, a failed business, and over 1,000 rejections before selling his franchised chicken model at 65 years old. 

18. Jerry Seinfeld

Jerry Seinfeld may be known as a comedic genius now, but he was booed off the stage for his standup in his career’s early stages. He didn’t give up, though, and eventually gave the world “Seinfeld,” the hit tv series. 

19. JK Rowling

The author of one of the most popular fantasy franchises ever, Harry Potter, was on welfare and was unemployed and divorced when she conceived the idea. She’s now worth about $650 million and has a name that is recognized around the world. 

20. Emily Dickinson

During her lifetime, the great author Emily Dickinson had less than a dozen of her poems published. It wasn’t until after her death that she finally gained international fame when her sister discovered nearly 1,800 poems of hers.

21. Elvis Presley

The king of rock and roll, Elvis Presley, was rejected by Sun Records and was told that he couldn’t sing at an audition. He took up a job as a truck driver before a friend connected him with a band, and Presley earned the attention of a professional D.J. to launch his career.

22. Mark Zuckerberg

Everyone knows Mark Zuckerberg for his founding and ownership of Facebook, but not many know that his career began with a failed website and an expensive lawsuit. However, today we can see the apparent success of his social media platform and his massive fortune.  

23. Stephen King

The master of horror himself was once just a regular English teacher who sold his short stories on the side. After receiving dozens and dozens of rejections, he has now published hundreds of books and is one of the world’s best-selling authors of all time.

24. The Beatles

The Beatles are one of the most famous rock bands of all time, selling over 1.6 billion records worldwide thanks to Paul McCartney, John Lennon, George Harrison, and Ringo Starr. So, it might come as a surprise to learn that an A&R told them they would never succeed. 

25. Walt Disney

The engineer of dreams himself, Walt Disney, was fired from his newspaper job at the age of 22 for lacking imagination and ideas and later went bankrupt with his first animation studio. Today, his company is worth $95.79 billion – and it all started with the creation of a friendly little mouse.  

26. Charles Darwin 

After dropping out of two universities, Charles Darwin was considered by his masters an ordinary boy and by his father a failure in life. But his intensive interest in nature allowed him to become one of today’s most influential scientific minds, resulting in his work with evolution, animal species, and natural selection.

27. Madonna

Madonna is a highly successful singer who is often even referred to as the Queen of Pop. But the star started out with no money, small gigs, and was even once robbed at knifepoint before debuting her single with Sire Records and growing to top the charts. 

28. Keanu Reeves

Although Keanu Reeves is a beloved actor today, his early life was wrought with tons of disappointment that included dropping out of high school and even losing a child, which ultimately led to a divorce from his wife due to grief. After starring in several minor roles, he finally caught his big break in “The Matrix” franchise and has been exceedingly successful since.

29. Mark Cuban

Mark Cuban is an American entrepreneur known for his role on “Shark Tank” and his ownership of the Dallas Mavericks, but he learned the hard way that the lifestyle wasn’t an easy one. He worked various odd jobs, failed at bartending and short-order cooking, and as a salesman before growing his own multi-million-dollar software company. 

30. Richard Branson

Though a billionaire today, Richard Branson made mistakes with his first record shop that caused him to pay a ton in fines and taxes. He gained success by selling his Virgin Records store and eventually creating the Virgin Group across music, telecom, hospitality, and travel.  

31. Thomas Edison

We’ve all learned at one time or another that Thomas Edison is a great American inventor and entrepreneur who invented the phonograph and the electric lightbulb. But did you know that he failed over 10,000 times during the electric bulb process? 

32. Sylvester Stallone

Best known for his role as Rocky Balboa, Sylvester Stallone faced tons of failure and often received negative feedback from the industry, telling him he talked, walked, and acted funny. He received over 1,000 rejections from the film industry and found himself homeless before writing the script for “Rocky” and playing the starring role. 

33. Chris Gardner 

Chris Gardener’s story was made famous when Will Smith portrayed him in the movie “The Pursuit of Happyness.” As a medical-equipment salesman, Gardner saw poverty, homelessness, divorce, and jail time before he met a businessman who helped turn his life around as a stockbroker. 

34. Charlie Chaplin

Charlie Chaplin grew up fatherless, poor, and soon motherless at a young age and was famously snubbed by Hollywood. Despite his hardships and failures, he went on to become the greatest silent-film actor ever.

35. Soichiro Honda

Soichiro Honda began his career working in an auto repair shop and later attempted his own business ventures, which failed. After going back to school, he eventually designed a motorized bicycle and started the Honda motorcycle – which led to the Honda Motor Company. 

36. Steve Jobs

Steve Jobs saw hard times at an early age, having been given up for adoption, dropping out of college, and being fired from a company that he actually created. Now, chances are, you’re reading this article on a device designed by Jobs and his legacy, Apple, which rules the tech industry today.

37. Marilyn Monroe

With her mother suffering from paranoid schizophrenia, Marilyn Monroe became a ward of the state early in her life and moved in and out of foster homes. After modeling on a series of magazine covers, she later lost her contract several times before she started appearing in critically-acclaimed films.

38. John Hamm

Any fan of “Mad Men” knows John Hamm’s name through his role on the hit television series. You might not know that at the beginning of his career, he could not land a single gig and his agency actually cut him before he gained success.

39. Elizabeth Arden

Elizabeth Arden’s first business venture was a partnership with Elizabeth Hubbard that failed after just six months. With great determination, Arden eventually developed her own line of beauty products and created Elizabeth Arden, Inc., which included 150 salons, over 1,000 products, and over $1 billion in annual sales to date.

40. George Lucas

George Lucas’s film franchise “Star Wars” was the highest-grossing film of all time, yet it was turned down by two different studios during his pitch. 20th Century Fox finally picked it up, despite Lucas’s failed films in the past. 

41. Howard Schultz

Howard Schultz is the reason behind the Starbucks that we see on every corner, but he came from nothing as a child. After failing to convince the company to expand as their Director of Marketing, he opened his own successful coffee shop, persuaded investors, and eventually bought Starbucks. 

42. James Dyson

Sir James Dyson invented a vacuum that didn’t require bags, which was revolutionary but widely discredited at the time. While his brand got him to the billionaire list today, many manufacturers constantly rejected his idea before it hit the market.  

43. Fred Astaire

Although Fred Astaire and his sister Adele’s act saw success on the New York City Broadway circuit, Astair didn’t receive the same treatment once his sister married and left the entertainment industry. After being told he couldn’t act, he carried on and made a very successful 76-year run in musicals, television shows, and recordings. 

44. Harrison Ford

Harrison Ford was told he would never make it as an actor after landing his first uncredited, minor role. However, he didn’t quit, and almost a decade later, he landed a role in “American Graffiti” and established a fruitful relationship with George Lucas. 

45. Jack Canfield

Jack Canfield is the literary genius behind the “Chicken Soup for the Soul” series. This internationally-acclaimed brand has sold over 500 million copies in 20 languages after seeing 144 rejections and lots of laughter. 

46. Henry Ford

Henry Ford’s first business venture, Detroit Automobile Company, failed due to inefficiencies in his vehicle design and a great deal of debt. His second-chance venture also failed, but his third try landed him the Ford Motor Company, which is still highly successful today.  

47. Mary Kay Ash

Mary Kay Ash was the genius behind one of the earliest multi-level marketing cosmetics companies that now sees over $3 billion in sales annually. Before her massive success, Ash was passed up for promotions and was stuck in a dead-end job. 

48. Shawn Carter (Jay-Z)

When no labels wanted to sign him early on, Jay-Z started his career by selling C.D.s out of the trunk of his car. He eventually paved his own path in the industry by creating his own record label – plus, he married Beyonce. 

49. Warren Buffet

Even billionaire investor Warren Buffet makes mistakes. Though his life holdings don’t demonstrate it, he deeply regrets purchasing a struggling textile mill just so he could fire the CEO as an act of revenge. 

50. Arianna Huffington

Arianna Huffington, the President and Editor-in-Chief of The Huffington Post, saw 36 rejections for her second book despite her past success. She also saw significant failure when she ran as an independent in the 2003 California governor election – but her accomplishments far outweigh these downfalls. 

51. Tina Fey

Tina Fey is widely known for her comedic genius now, but she had to hustle to get there. Despite the industry’s desire to keep her behind the scenes as a writer, she worked hard to get herself on camera – and it paid off big time.

52. Conan O’Brien

After securing his dream of becoming the Tonight Show host, Conan O-Brien was quickly disappointed when NBC dropped him. However, he went on to host his own late-night talk shows and has seen great on-air success.

53. Sara Blakely

Sara Blakely is the creator of Spanx, the leading manufacturer of shapewear that’s become viral in women’s fashion. Blakely went through a series of rejections before finally securing a deal with a manufacturer and moving onto success. 

54. Jeff Bezos

One of the richest men alive lost billions of dollars through failed companies and products before building the Amazon empire. Now, he embraces failure, uses it to innovate better, and is worth $150 billion.

55. Nick Woodman

Nick Woodman attempted to establish several failed businesses before getting even close to success. As the creator of GoPro, he now has a net worth of $990 million and has sold over 30 million cameras globally. 

56. Vera Wang

Today, women covet dresses made by the famous designer Vera Wang, who frequently works for high-profile celebrities. However, she was rejected for the Editor in Chief position at Vogue several times before venturing out on her own and establishing her fashion empire.

57. Sophia Amoruso 

Sophia Amoruso was actually quite successful with her shop Nasty Gal on eBay and her subsequent online store. While she declared bankruptcy in 2016, she still has an estimated net worth of $10 million, with a comeback underway.

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