Oprah Winfrey hated this part of her job until she asked herself one life-changing question

This billionaire started with nothing, but she made it anyway
This billionaire started with nothing, but she made it anyway

Over the past 30 years, media mogul and self-made billionaire Oprah Winfrey is best known for redefining the broadcast television talk show and influencing the American media and pop culture landscape with "The Oprah Winfrey Show."

"For 10 years straight [and] every single day, I shook hands with 700 people and I signed 700 autographs," Winfrey said in a recent interview with LinkedIn CEO Jeff Weiner.

At that point, a decade into doing her show, Winfrey said she realized there was one crucial question she was neglecting, a question that had the power to change her career and can change yours as well: "What do I really want?"

Winfrey described one day when she had a doctor's appointment which made her short on time and did not allow her to do her meet-and-greet with guests in between the usual two tapings of her show.

To her surprise, skipping the autographs gave her a boost of energy she did not expect.

"I realized, 'Wow, that's a lot of energy I'm giving out in between shows,'" Winfrey recalled.

"All those years, for 10 years, I had done the autographs because I thought that's what you had to do, because that's what people wanted," she said. "But I never asked, 'What do I want?' I had never said, 'But what do I really want?' I hated it."

Winfrey said that signing all of those autographs felt "vapid" and "meaningless," even thinking to herself about her guests, "By the time you get home you won't even have that piece of paper."

That's when she realized the answer to her life-changing question: "What I really want is to connect."

"What I've found over the years in the multi-thousands of interviews I've done [is] that most people cannot answer that question," she said.

From that point and on, Oprah worked on getting to know her audience by speaking with them every day after her show instead of signing autographs.

"Most people don't know this, but my favorite time of the show was usually after the show," Winfrey said, describing the 30 to 60 minutes she would spend with the audience.

Speaking with her audience, Winfrey said, allowed her to view them as a "compass" that would become a tenet for her iconic self-discovery discussions she would later be known for as a talk show host.

Gretchen Rubin: The key to your happiness depends on these 2 things
Gretchen Rubin: The key to your happiness depends on these 2 things

Winfrey said that around 1992, audience members, especially women, would stand up and say, "I did the thing I was supposed to do, I went to school, I got the degree, I even got my master's degree, I did the work and now what? I feel like there should be something more."

If you find yourself searching for happiness and success, Winfrey suggested that you ask yourself the same question she would repeatedly share with her audience, "What do I really want?"

Though time and time again, the audience members would say they just want to be happy, Weiner added that the more specific you are when you answer that question for yourself, the more likely it is to happen.

"If you know what you really want, what you really love, what really resonates and you have the ability to do that or at least you are in a position where you can learn the skills over time, you can make it happen," Weiner said.

Winfrey said that by reminding others to reflect on their lives, she was putting out a message for people to take better care of themselves.

"I actually know that one of the reasons I am here is to fulfill that for myself but to also help other people to do it," she said.

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