Oprah Winfrey Reveals Her One Regret in Life: ‘I Should Have Handled All of That Differently’

Oprah Winfrey is opening up about the one decision she regrets making in her career.

In a conversation with Al Roker on Today, Winfrey, 70, reflected on her successes and failures throughout her life as they discussed Roker turning 70. Thinking back to when The Oprah Winfrey Show came to an end in 2011, the host admitted she wished she hadn’t jumped into another project right away.

“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.”

She continued, “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.”

Winfrey explained that she felt pressure from those around her to “leverage this moment” to create something new when her show’s ending put so much attention on her. After 29 seasons, she said she wanted “a break.”

“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 confessed. “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.”

Now, Winfrey said she values her downtime and rest more than anything. The simple things, she said, are what bring her the most joy.

“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.”
When Roker asked if she thought she would be the same person if her show had begun now rather than in 1986, Winfrey was quick to say “no.” She explained that she is proud she was able to approach topics that people would not have been free to speak about without her show.

It was a different time,” she said. “I often think about this just even in terms of The Oprah Show and the immense range of subjects that we covered on a daily basis. We were just talking about what was going on in people’s lives in a real and meaningful way. Raising children, overcoming cancer, stepping away from abuse. Every single imaginable dysfunction in our culture, that Oprah Winfrey Show was able to address in a way that allowed people to see the best of themselves and the possibility of what could be.”

“I was just speaking in Grand Rapids and someone said, ‘You changed my life because you allowed me to see what I could be versus what I thought I had to be,’ which is really a great testimony for what a television platform could do,” she added