Oprah Winfrey Reveals Her One Regret After Ending ‘The Oprah Winfrey Show’

Oprah Winfrey said her one regret in life was her decision to move forward with the launch of her basic cable channel the Oprah Winfrey Network (OWN) instead of taking a break.

“I would not have taken on the responsibility of trying to build a network while still ending the show,” the media mogul told Al Roker in a conversation on “Today.” “That is my one regret … 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.”

Winfrey’s award-winning and groundbreaking talk series made its debut on Sept. 8, 1986. After 29 seasons and 4,561 episodes, the show ended on May 25, 2011 — a choice Winfrey still supports.

“I’d made my 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,” she explained.

News of Winfrey starting her own network was reported in early 2008, and OWN officially launched on Jan. 1, 2011. The journalist and TV host said she was told to transfer the attention she was receiving from the show’s departure to a new venture, though she truly just wanted some time to rest.

“Everybody has that natural life force instinct inside yourself that lets you know what’s right or wrong, or that is your emotional GPS system, and any time I’ve ever gone against that, any time, is when I’ve made a mistake,” Winfrey admitted. “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.”

However, life remains great for Winfrey all these years later, rain or shine … but mostly rain.

“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.”

This isn’t the first time Winfrey has spoken up about the doubts she felt about starting OWN. During a 2012 interview with “CBS This Morning,” Winfrey said she probably would have pivoted into a different business venture if she had known it was going to be a hefty challenge.

“The idea of creating a network was something that I wanted to do. Had I known that it was this difficult, I might have done something else,” she said at the time, adding that she wouldn’t give up on her channel in spite of the financial troubles OWN was going through. “Just because you fail doesn’t make you a failure. When you know that in the core of yourself, you can keep trying or you can use whatever is happening in that moment to say, ‘Maybe I need to move in a new direction.’”

While Winfrey sold off most of her stake in OWN in 2020, she remains CEO.

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