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Oprah Winfrey reveals the decision she regrets: 'I should have handled that differently'

She also said that she felt pressured to keep going at the time.


Daniel Neira
Daniel Neira - Los Angeles
Senior WriterLos Angeles
AUGUST 21, 2024 9:51 AM EDT

Oprah Winfrey is opening up about one of the decisions she regrets the most during her successful career in the entertainment business. The businesswoman looked back at some of the defining moments of her life as she reflected on turning 70.

During her latest interview with Al Roker on Today, Oprah talked about her multiple projects and businesses, including her popular 'The Oprah Winfrey Show' which came to an end in 2011. Oprah decided to start a new project right after she ended her time on the show, and she admitted she wished she had given herself more time. 

“I would not have taken on the responsibility of trying to build a network [OWN] while still ending the show. That is my one regret,” she said. “I should have handled all of that differently, I think. I should have completed one thing, taken a year to do nothing, and then decided what was the next thing for me to do.”

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Oprah continued to explain; “I’d made a decision that it was time for the show to end, I don’t regret that. What I do regret is trying to do multiple things at the same time. I would have done the thing that I tell everybody else to do: ‘When you don’t know what to do, do nothing. Get still with yourself and do nothing.’ I would have given myself that time.”

Oprah Winfrey speaks onstage during the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024, in Los Angeles, California. © Getty Images

She also said that she felt pressured to keep going at the time. “Every time I’ve just gotten still and listened to what my gut said — what that still small voice that resides inside me and you and everybody else says — I would never have made a mistake.”

After her incredible success, Oprah says she enjoys every moment of her life. “If it's a rainy day, I’m in love with life. You know why? No expectations,” she said. “Nobody expects you to go out on a rainy day. If it’s bright sun everybody’s like, ‘Come on, let’s do that that that.’ I love myself a rainy day. Rainy day, a fireplace, a blanket, and a dog at your foot and a great book? That’s it. That’s it for me.”