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October 1, 2026
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You Get Advice, You Get Advice: All of Oprah Winfrey’s Best Lessons on Career and Life

“The greatest lesson I’ve learned throughout my career came from Maya Angelou, actually, when I was first meeting her,” Oprah recalled backstage at the 2018 Golden Globes. “After I’ve known her for a while, she said, ‘Baby, you need to know that when people show you who they are, you believe them the first time, and your problem is it takes you 29 times to see the same lesson coming in a different skirt or wearing a different pair of pants.'”

She continued, “So I think that has been one of my greatest wisdom teachings, is to asses from people’s behavior, their actions—not just towards me, but towards other people—who they are and how they behave, because if people talk about other people, they’ll talk about you. So I think in business and personal relationships, that’s been my greatest lesson. Also staying grounded, has been really great for me.”

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