Moment No. 1: Moving from Milwaukee to Nashville as a young teen (via PEOPLE).
“When I was in Milwaukee, I was trapped in a world where I could see how dire it was,” she says. “Had I not gotten out of Milwaukee, nothing would have been the same. I do believe I would have been dead at 56. I believe I would have been 437 lbs. I believe I would have had diabetes. I would have had high blood pressure. I would have suffocated knowing that things could have been different.”
Winfrey also noted that “ ‘Nothing is waste.’ There is not a moment that you can have that can’t turn out to be useful later in life, and if you know that, life is like this huge, giant classroom,” she said.
Moment No. 2: Swearing off sensationalist TV in 1989 after two pivotal episodes.
“It was the KKK skinhead show [during which fights broke out repeatedly and one guest was kicked out for profanity] and then the show with a man, his wife . . . and his mistress,” Winfrey recalls. “At the time, the producers thought this was one of the greatest bookings we could ever get. We thought, ‘He’s agreed to come on with his girlfriend? This is unbelievable.’ Then there was a moment when the man says to his wife, ‘You know what? There’s nothing you can do about [the affair], because [my mistress] is pregnant.’ We were live and I didn’t know he was going to tell her, nor did the producers know.”
“It’s one of my greatest shames, but a shameful act that allowed me to make the shift, because I go, ‘Never again will I do that to somebody,’” she says. “If I hadn’t, I would have been out of television much sooner.”
Winfrey also opens up about the childhood dream that haunted her throughout her journey to success.
“I used to have this dream that I was going to be dead at 56, so the year that I turned 56 I was filled with dread,” Winfrey says. “I had only told one other person that I had a number in my head when I was going to die, and that was Gayle [King, her best friend]. Gayle said, ‘What’s the number?’ I said, ‘I’m not going to tell you, because you will drive me crazy and then I will end up dead.’”
She added, “When I got to 57, it was like, ‘Why did all my life I think it was going to be 56?’” she says. “At the time I started having this vision of 56, it was when I was in Milwaukee and I was trapped in a world where I could see how dire it was.”
For the rest of the five moments that changed Winfrey’s life pick up the new issue of PEOPLE!
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