“I should have handled all of that differently.”
With a net worth of $3 billion and a legacy as one of the most notable television trailblazers of all time, the name Oprah Winfrey is synonymous with success. But even someone this powerful makes mistakes, and the media mogul is opening up about the moment when she felt she’d made her biggest wrong turn.
In an interview for The TODAY Show, host Al Roker asked Winfrey about which part of her life she’d most want to “do over” if she had the opportunity — and she knew her answer instantly.
“I would not have taken on the responsibility of trying to build a network while still ending [The Oprah Winfrey Show],” she said. “That is my one regret. I should have handled all of that differently, I think.”
She’s referring, of course, to the Oprah Winfrey Network (OWN), which launched on Jan. 1, 2011. Winfrey’s legendary talk show was still on the air at the time — its 25-year run didn’t come to an end until May 2011. For months, Winfrey was landing the plane on her career-making series while also devoting herself to the even bigger undertaking of staffing, building, and programming an entire cable channel.
And at first, things did not go well. OWN launched to soft ratings, and the low viewership felt especially dire as the press seized on a rare deviation from the conventional wisdom that anything Winfrey touched would turn to gold. As Vulture put it the year after the network’s launch: “Celebrity schadenfreude seems to be reaching an all-time high when it comes to Oprah Winfrey and the seemingly endless troubles of OWN.”
It seems Winfrey understood this pretty immediately. In April 2012, she said that if she were to write a book about OWN’s launch, she would call it 101 Mistakes.
“The idea of creating a network was something that I’d wanted to do. Had I known that it was this difficult, I might have done something else,” Winfrey told her friend Gayle King at the time. She even compared the network’s kickoff to a life event no one hopes to experience: “It’s like having the wedding when you know you are not ready. You are walking down the aisle and saying, ‘I don’t know…maybe we should have postponed it,'” Winfrey said.
In her conversation with Roker, she explained that while she wanted a break after her talk show, she got advice to the contrary. “Other people were saying, ‘Oh no, you’ve just got to leverage this moment and keep moving up.'” In retrospect, though, Winfrey wishes she had “taken a year to do nothing, and then decided what was the next thing for me to do.”
“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,” Winfrey recalled. “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.”
It seems the biggest lesson Winfrey learned from the whole experience was the importance of listening to her gut.
“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. Any time I’ve ever gone against that — any time — is when I’ve made a mistake,” Winfrey shared. “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 have never made a mistake.”
