1. Jon Hamm
At 27, Hamm couldn’t find any work and was dropped by the William Morris Agency. He vowed to quit acting if he couldn’t get his career rolling by 30. Fortunately, he landed a role on the NBC drama Providence at age 29.
2. Oprah Winfrey
Oprah bounced around various Baltimore news stations, including one that fired her for getting too emotionally invested in stories. Her demotion to daytime TV proved a blessing in disguise, and by 30 she had the highest-rated talk show in Chicago.
4. Tim Allen
In his mid-twenties, Allen spent over two years in federal prison for selling cocaine. The experience forced him to turn his life around and revive his stand-up career.
7. Ang Lee
After earning his master of fine arts, Lee spent six years as a stay-at-home husband while his film career stalled. Ashamed, he briefly considered a career in computer science until his wife, the family’s sole earner, urged him to continue pursuing his dream.
9. Walt Disney
At 24, he had Oswaldo the Rabbit, his first successful cartoon character, stolen from him by Universal Studios. At 25, MGM told him no one would ever like Mickey Mouse. At one point in his twenties, Disney was so poor that he resorted to eating dog food.
10. Suze Orman
Orman spent most of her twenties working as a waitress. After an attempt to open her own restaurant bankrupted her, she became interested in finance and pursued a career as a broker.
11. R.A. Dickey
After a successful college career, Dickey suffered so many arm injuries he couldn’t even turn a doorknob without significant pain. Desperate to stay in the game, he began experimenting with the knuckleball, worked his way back into the major leagues, and won the National League Cy Young Award at age 37.
12. Zach Galifianakis
While trying to jump-start his standup career, Galifianakis spent a large portion of his twenties as a busboy in an upscale Manhattan strip club.
14. Sylvester Stallone
While shopping Rocky around Hollywood, Stallone was so poor he tearfully sold his dog Butkus for $25. Once Rocky was purchased, he bought the bullmastiff back for $3,000 and even gave the buyer a small part in the film.
15. Steve Jobs
Although Jobs was a millionaire by 23, he became so disliked at Apple by the end of his twenties that his own company fired him. Jobs credited this devastating setback with helping him enter “one of the most creative periods” of his life.
16. Lucille Ball
During her twenties, Ball was known as the “Queen of the ‘B’s” thanks to her frequent roles in B-movies. Her agent recommended she find a new career, and it wasn’t until 40 that Ball became a household name on I Love Lucy.
17. James Dyson
Relying heavily on his wife’s income, Dyson spent the majority of his twenties failing to sell his vacuum cleaner designs to major manufacturers. At 39, he sold his first U.S. patent, allowing him to open his own manufacturing company.
19. J.K. Rowling
By the end of her twenties, Rowling was a divorced, unemployed single parent on welfare. After being rejected by eight publishers, Harry Potter and the Philosopher’s Stone was published right before her 32nd birthday and quickly became a best-seller.
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