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Home » Oprah Winfrey Says People-Pleasing Led to Her Making a Bad Career Move
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Oprah Winfrey Says People-Pleasing Led to Her Making a Bad Career Move

EditorBy EditorSeptember 18, 2026No Comments3 Mins Read
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Oprah Winfrey, 72, said she made a career decision she knew was wrong, simply because she didn’t want to disappoint others.

Speaking on Thursday’s episode of “The Mel Robbins Podcast,” Winfrey reflected on the difficult early years of OWN: Oprah Winfrey Network.

Winfrey launched OWN in January 2011, months before “The Oprah Winfrey Show” ended its 25-year run in May that year. The network struggled with low ratings and later made highly publicized layoffs, including 30 staff cuts in March 2012.

“2012 was one of the worst years of my life,” Winfrey said. “Every single story headline about me was ‘Oprah and the struggling OW Network. Oprah and the struggling OW Network.’ And it was hurtful and painful to me because it was the truth. I was struggling.”

Winfrey said she was “so angry” for not trusting “the voice inside myself,” which was “so strong” that she would wake up in the middle of the night unable to breathe.

Despite her doubts, Winfrey said she pushed ahead with the venture because she felt bound by the agreement she had signed.

She later realized she hadn’t moved forward because she truly wanted to, but because she was afraid of disappointing the people involved.

“I was keeping my word because I was trying to please the people on the other side. I was thinking, ‘What are they going to think of me for changing my mind?'” Winfrey said.

She compared it to getting ready to walk down the aisle and realizing the marriage is not right. Even if the invitations are out and everyone is waiting, she said, it’s still OK to walk away.

Winfrey said it was the lesson she knew, but failed to follow: “You always have the right to change your mind.”

In a 2024 Today interview with Al Roker, Winfrey reflected on her decision to start a major new venture during the final stretch of her talk-show career.

“I would not have taken on the responsibility of trying to build a network while still ending the show,” she said. “That is my one regret. That is my, ‘I should’ve handled all of that differently.'”

OWN launched as a joint venture between Winfrey’s production company, Harpo, and Discovery.

In 2017, Discovery paid $70 million to acquire an additional 24.5% stake from Harpo, increasing its ownership of the network to more than 70%.

In 2020, The Hollywood Reporter reported that Winfrey exchanged most of Harpo’s remaining stake in OWN for Discovery shares worth more than $35 million. The deal raised Discovery’s ownership to 95%, while Harpo retained a 5% stake.



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