Oprah Winfrey: If I had to start over again, here’s what I would do

Oprah Winfrey recently became one of the 500 richest people in the world and has her decades of experience in media and business to thank for her success. But had Winfrey not chosen to pursue Entertainment, the self-made billionaire knows what she would be doing: “I would definitely, definitely, definitely be teaching in a classroom,” Winfrey says in a new interview with British Vogue editor-in-chief Edward Enninful.

“It’s the thing that still brings me the greatest joy.”

Winfrey gets to live her dream in a way by remotely teaching students at the Oprah Winfrey Leadership Academy for Girls, an all-girls boarding school that Winfrey founded in South Africa in 2007. Feeling like she’s gotten through to the students and helped them understand something, she says, is her “favorite moment in the world.”

For example, she tells Enninful, some eighth graders told her that being in boarding school made them miss their parents and feel alone. Winfrey shared one of her favorite Maya Angelou quotes from the poem, “Our Grandmothers”: “I come as one, but I stand as 10,000.” Then Winfrey directed the students to close their eyes and think of their parents. “Now, think of their mother and their father. Now, think of their mother and their father,” she said.

“I did that for a minute until they started giggling and I said, ‘That is your 10,000. So when you walk into a room, you never walk alone. You walk with the 10,000 who have come before you, who are with you and are constantly surrounding you,” she told the students. “And I see when they get it, which is just fantastic. When the light goes on and you realize, ‘Oh, they got it.'”

Here’s how other successful entrepreneurs, including Mark Cuban and Bill Gates, answer the question of what they would do if they had to start over.

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