April 2024

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Your 20’s are generally a time of experimentation and transition. While some may have just graduated from school and are trying to find a job, others may be struggling to figure out their goals in life. The following 12 people prove that there is no one path to success. They all spent their 20s very differently. Many of them struggled, took unconventional paths and turned out to be successful.

1. Warren Buffett

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Buffett is the most famous investor in the world and is consistently one of the world’s wealthiest people. When he was younger, he got rejected from Harvard Business School. That failure did not stop him from pursuing his dream to become a stockbroker. He had an interest in business at a young age and worked his way up in the field. He attended Columbia Business School and then worked as an investment salesman, securities analyst, and stockbroker.  

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2. Oprah Winfrey

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When Winfrey started her career as a news anchor for local Baltimore television station WJZ-TV. Two years later,she was recruited to join Richard Sher as co-host of WJZ’s local talk show People Are Talking, which premiered on August 14, 1978. She was demoted her to work in a failing talk show. In 1983, she moved to Chicago to host WLS-TV’s low-rated half-hour morning talk show, AM Chicago. It was a turning point in her life. The show became popular and was later renamed the Oprah Winfrey Show.

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3. Jay Z

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Rapper Shawn Carter adopted the stage name Jay Z when he was 20. Since he was not signed to any label, he used to sell CDs out of his car. At age 27, Carter founded Roc-a-Fella Records with two friends and released his debut album, Reasonable Doubt. Today, his net worth is estimated at $520 million.

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4. Harrison Ford

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Ford took a drama class during his final year of college to help get over his shyness. He obtained a pilot’s license but ended up working as a carpenter to make ends meet. His big break in Star Wars did not come until his 30s, and it was by complete chance. He was renovating director George Lucas’ office and ran some lines with auditioning actors. Lucas was impressed and decided to cast Ford.  

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5. Tyler Perry

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Actor and playwright Perry escaped a life of poverty and abuse and moved to the city of Atlanta. He barely got by and was living in a tiny apartment working on his writing. After his first play did not perform well, he was broke. At age 28, he was living on the streets. Now he is one of the most successful people in the entertainment industry.  

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6. Martha Stewart

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Stewart tried out a couple of different industries before finding her calling. She worked as a model when she was young and then as a stockbroker on Wall Street for five years – at a time when there were very few women working in Wall Street. She left the banking industry to become a stay at home mom and then she started a catering business a year later.  

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7. Tina Fey

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After graduating from college, Fey moved to Chicago. She worked as childcare registrar at a local YMCA to support herself while she attended acting workshops. The turning point of her career came when she was invited to join the improv troupe The Second City. Her networking landed her a role on the famous show Saturday Night Live. She was hired as a writer at age 27 and began performing in the sketches three years later.

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8. Morgan Freeman

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Freeman is one of the most famous actors in Hollywood, and he worked hard to earn it. He spent his 20s as a starving artist. He moved to Los Angeles when he was 22, worked as a transcript clerk at LA City College and did several minor, uncredited roles so he could join an actor’s union. He did not land his career changing role in Driving Miss Daisy until he was 52 years old.

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9. Ralph Lauren

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Ralph Lauren is an internationally successful brand. The founder and former CEO, Ralph Lauren himself, served in the army until he was 24. He then worked as a sales assistant for Brooks Brothers. His big break came when he designed a wide European-styled tie at age 26, which was picked up by Neiman Marcus. One year later, he was able to launch his brand.

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10. Mark Zuckerberg

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Zuckerberg is famous for launching Facebook from his dorm in Harvard. After it launched, he battled lawsuits from students who claimed he stole their ideas. The case was settled and Zuckerberg dropped out his second year of college to finish his project.

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11. J.K. Rowling

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Rowling came up with the idea for Harry Potter when she was 25 years old. But that was just the beginning. It took years of struggling to get the book published. She was even fired from her job as a secretary for the London office of Amnesty International because she could not focus. She used the severance check to get by while working on her writing. She finished the book five years later, getting divorced and diagnosed with depression along the way. The manuscript was rejected several times before finally getting published two years later. The Harry Potter series have sold more than 400 million copies worldwide.

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12. Jon Hamm

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Before he was famous for playing Don Draper on Mad Men, Hamm struggled to book acting jobs in his 20s because he looked older than he was. To survive, he worked as a waiter and a softcore adult movie set designer. He set an ultimatum for himself – book a job by the time he was 30 years old or quit the business. He finally landed a role in the NBC show, Providence.

SEE ALSO: World’s Wealthiest Women Of All Time.

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