When she was up for The Color Purple (1985), Winfrey was in a contract with ABC that only allowed her two weeks of vacation—AKA not nearly enough time for filming. Since she had three weeks of vacation the following year and four the year after, she suggested a compromise to her superiors. "I begged my bosses, 'If you just let me do this film, I will not take another vacation for the next three years. I will use the next two years’ vacation to compensate for that,'" she told Vulture.
Then her lawyer at the time, Jeffrey Jacobs, spewed some wisdom that forced her to view the situation—and her own self-worth—much differently: He said she shouldn't be in a position where she has to beg. And she shouldn't have to give up her vacation time or sacrifice for something that's really close to her heart. He said she instead should approach her bosses with the idea of ownership.
"I was like, 'How are you going to do that? How am I going to own it?' And he said, 'Well, you have to believe that you’re worth the risk. If it doesn’t work, you lose, but if you actually, really believe that it’s going to work, you win big.'" —Oprah Winfrey
"I was like, 'How are you going to do that? How am I going to own it?'" Winfrey said. "And he said, 'Well, you have to believe that you’re worth the risk. If it doesn’t work, you lose, but if you actually, really believe that it’s going to work, you win big.'"
Ultimately, Winfrey did win big—in the form of an Academy Award nomination for her work on the film. She was able to do something she wanted "more than anything else in my lifetime" because she bet on herself. While taking risks can be absolutely terrifying, so many things in life that are worth the trouble simply are.
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