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‘Challenges are Gifts…Don’t Fight Them’: Five Success Lessons from Billionaire Media Mogul Oprah Winfrey

Self-made billionaire Oprah Winfrey’s life reads like one of the bestseller novels she promotes in her book club. The media mogul rose from poverty, abuse, teenage pregnancy and being a runaway to become one of the world’s most notable people.

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In this screengrab, Oprah Winfrey speaks during the GCAPP EmPOWER Party & 25th Anniversary Virtual Event on November 12, 2020 in UNSPECIFIED, United States. (Photo by Getty Images/Getty Images for GCAPP)

Up from Poverty

Born Jan. 29, 1954, in Kosciusko, Mississippi, to an unmarried teenage mother, Winfrey’s early life was full of challenges. Growing up with her grandmother, in a poor upbringing, she experienced sexual abuse that caused her to run away from home at age 13. At age 14, she became pregnant but her baby was born prematurely and died shortly after birth. The young Winfrey was sent to live with her biological father in Nashville, Tennessee. There, she seemed to thrive. A 17-year-old Winfrey won a Miss Black Beauty Tennessee pageant, which led to a part-time job at a local Black radio station called WVOL where she worked as a news anchor. Thus, her passion for media was born.

A Media Maven was Born

Winfrey went on to earn a scholarship to Tennessee State University, and she studied communication. But at age 19, she dropped out of school to pursue a career in media full-time. She soon became the first Black female news anchor at WLAC-TV in Nashville. By 22, she was a news co-anchor at Baltimore station WJZ.

Her venture into talk shows dates back to August 1978 when she began co-hosting a talk show called “People Are Talking.” The show was a success and paved the way for a deal with ABC in 1984 for her own 30-minute morning talk show in Chicago, produced by King World Productions. She landed a four-year, $1 million contract. By 1986, the popular show had been rebranded to “The Oprah Winfrey Show.” It was now broadcast nationally through syndication and expanded to a full hour.

But Winfrey was not satisfied with her contract, feeling she was not being paid the value of her show. But King World refused to renegotiate. She and agent Jeffrey Jacobs instead launched HARPO Productions and produced the show.

Winfrey owned 90 percent of HARPO. Jacobs owned 10 percent, Fortune reported. The two worked out a bigger deal with ABC that allowed them to expand her brand into movie productions, a magazine, books and other TV projects. She built HARPO Studios for production purposes.

On top of this, Winfrey and Jacobs negotiated an ownership stake in King World Productions through which Oprah would earn money off every show King World produced, such as Jeopardy and Wheel of Fortune.

CBS acquired King World for $2.5 billion in 1999, and, with this deal, Winfrey wound up owning 1 percent of all of CBS.

By 2000, Winfrey hit billionaire status, earning $300 million annually from her own show as well as Dr. Phil’s and Rachael Ray’s shows. She ended her show in 2011. She has an estimated net worth of $3.5 billion.

Since the end of her show, she has done various successful deals, such as with Weight Watchers, and obtained assets such as real estate, along with given away millions to charity.

Here are five success lessons she learned along the way.

1. Authenticity is a Must

Bt operating in authenticity, genuine connections can happen.

“I had no idea that being your authentic self could make me as rich as I’ve become. If I had, I’d have done it a lot earlier,” Winfrey, 68, once shared.

“I think that moment,” she said on the Dear Sugars podcast in 2017, “and then the rest of the audience relating to that moment, I started to realize that being yourself, allowing yourself to be vulnerable, embracing your faults, that everybody has them, that’s what gives you power.”

She also talked authenticity earlier in 2013 at a Essence Black Women in Hollywood luncheon.

“The truth is, I try not to let other people define for me whether I have power or don’t,” Oprah said. “I ended the show, and then there were a whole bunch of people who said, ‘Oh, you don’t have power anymore.’ But the truth is, I know who I am, and the thing about power for me is that it’s connected to a source that’s obviously greater than myself. Any time you can connect to the source and understand that that’s where all of your energy, your creativity, your joy and your triumph come from, I consider that to be authentic power.”

“People will support you and your business if you’re authentic since they can smell BS from a mile away,” notes Mashable.

2. Risks Can be Worth Taking and Challenges Worth Meeting

According to Winfrey, “I believe that one of life’s greatest risks is never daring to risk.”

She took risks a number of times on her show, such as when in 1988 she had a group of Neo-Nazis on her show. Of course, it was controversial but it got the nation watching.

She also says, “Challenges are gifts that force us to search for a new center of gravity. Don’t fight them. Just find a new way to stand.”

Entrepreneurs are constantly faced with challenges, from how to lure in consumers to how to handle economic shifts. Thus, it makes sense to look at challenges as opportunities for growth, as Winfrey notes.

3. Operate on Your Highest Level

Giving a person’s all to his or her business or career means not taking shortcuts or skirting responsibilities.

“My philosophy is that not only are you responsible for your life but doing the best at this moment puts you in the best place for the next moment,” says Winfrey.

4. Trust Your Instincts

“Your gut is your inner compass. Whenever you have to consult with other people for an answer, you’re headed in the wrong direction,” says Winfrey.

5. Be Willing to Say ‘No’

Winfrey knows some things about how saying “yes” to everything can stretch a person thin, and how every opportunity isn’t necessarily a good fit.

“If a person turns against you because you say ‘no’ to them, you recognize that that wasn’t real love anyway,” Winfrey said during an episode of the “Dear Sugars” podcast. “True love, true friendship, true support comes from people who want you to tell your own truth. They don’t want things given to them that don’t come from a pure place.”

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