Oprah Winfrey Tells Al Roker Her Biggest Regret Happened In 2011, And Reveals What It Is

In a moment that will forever go down as “Oprah’s Confession Hour,” the queen of talk shows, Oprah Winfrey herself, decided to spill the tea about gasp her one regret in life. Yes, even Oprah—superhuman Oprah—has regrets. And no, it’s not about the time she gave away too many cars or unleashed the nation’s obsession with bread.

It all came out during a cozy birthday chat with Al Roker, who was celebrating his grand entrance into the 7th decade of life. Oprah, who’s also 70 but clearly aging like a fine wine while the rest of us are stuck in the discount vinegar section, revealed the one thing she wishes she’d done differently.

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Picture it: 2011. Oprah’s saying farewell to The Oprah Winfrey Show, a show so beloved that people cried harder at its finale than they did at the ending of Titanic. But, because Oprah doesn’t do anything by halves, she was also juggling the birth of her shiny new brainchild—her OWN network.

And that, my friends, is where Oprah’s tale of woe begins.

When asked if she regrets anything, Oprah didn’t hold back. “I probably shouldn’t have tried to run an entire network while simultaneously wrapping up a show that had been on air since, well, basically the dawn of time,” she admitted. “That’s my one regret. I should’ve just, I don’t know, finished one thing, taken a year to sip tea on a mountain, and then thought about the next project.”

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In classic Oprah fashion, she wasn’t throwing a full-blown pity party. She did clarify that ending The Oprah Winfrey Show was definitely the right move. But trying to become the queen of all media platforms at the same time? Let’s just say, even Oprah has limits. “I should have followed my own advice,” she sighed, probably imagining the tropical vacation she missed out on. “When you don’t know what to do, do absolutely nothing. Just sit there and marinate in it. Like, seriously. Go binge-watch some TV, eat a cupcake, whatever. Just don’t start a whole network.”

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She went on to wax poetic about our internal emotional GPS system (yeah, apparently we all have one—thanks, Oprah) and how every time she ignored it, life gave her a giant slap on the wrist. Oprah’s gut is basically the Yoda of decision-making, and when she’s ignored it, well… let’s just say things haven’t always turned out Oprah-perfect.

In the end, Oprah’s advice to all of us mere mortals? Get quiet, listen to your gut, and don’t try to take over the world and the media industry simultaneously. We’ll leave that to the superheroes. Or, you know, Oprah on a less busy day.

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