📖 Oprah Winfrey's origin story

A review of Oprah's early years and the skills she developed before turning 30 that led to her success

Welcome to Origin Stories. In this newsletter, we review the stories of successful people to unpack the skills they cultivated before they turned 30 that prepared them for success.

You’ll learn the what (what skills set them apart), the how (how they developed these skills at a young age) and - most importantly - how you can develop these skills, too.

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Today, we're diving into the story of Oprah Winfrey. Oprah is a media mogul, actress, talk show host and television producer. She is best known for The Oprah Winfrey Show, the record-setting talk show that ran for 25 years. In 2011, Oprah launched her cable channel OWN. Her net worth is estimated by Forbes to be roughly $2.5 billion.

From a heartbreaking childhood to a media executive, we explore the early years of Oprah Winfrey to find out how she developed the skills that led to her enormous success.

Childhood

Born in Mississippi in 1954, Oprah's birth name was Orpah, but it was mispronounced so regularly that she stuck with Oprah. The daughter of an unmarried teenage mother and an uncertain biological father, Oprah spent the first six years of her life living with her grandmother in great poverty, evidenced by the stories of Oprah teased for wearing dresses made of potato sacks.

While with her grandmother, Oprah "was beaten regularly,” she explained during a lecture series. Oprah recalls a time that her grandmother punished her for putting her fingers in a bucket of water she had retrieved from the well. “She whipped me so badly that I had welts on my back and the welts would bleed,” she said, which then stained her good Sunday dress. “So then I got another whipping for getting blood on the dress.”

"It is because I was raised poor, and no running water, and going to the well, and getting whippings that I have such compassion for people who have experienced it. And so it has given me a broader understanding and a deeper appreciation for every little and big thing that I now have"

Oprah in an interview with Gina Vivinetto

It wasn't all bad - her grandmother taught Oprah to read by the age of three, and Oprah showed an impressive ability to memorize. She was so prolific at reciting Bible verses that the local church group nicknamed her The Preacher. The approval and acceptance she felt after speaking to the congregation left a mark.

Two days into Kindergarten, Oprah wrote a note to her teacher that read “I don’t think I belong here ‘cause I know a lot of big words.” Oprah was promptly moved to the first grade. After one year in the first grade, she was promoted to third grade.

Difficult Early Years

Oprah moved often. After her grandmother became ill, the 6 year-old Oprah moved in with her mother Venita in Milwaukee, Wisconsin. Since her mother worked long hours as a maid, the young Oprah was left on her own.

Oprah at 12 and 13 lived in the same two-bedroom apartment as her 14-year-old male cousin. They slept in the same bed, and before long, he began to fondle her and, finally, he raped her. Oprah later said, "I didn't tell anybody about it because I thought I would be blamed for it. I remember blaming myself for it, thinking something must be wrong with me."

Years later, in a 1988 People magazine interview, Oprah said she desperately wanted love from her mother, who was too busy working and tending to her own life. The bonding never took place. She recalled, "Not getting much attention from my mother made me seek it in other places, the wrong places."

Oprah's wildness wasn't confined to home. She started staying out late, remaining away for the entire night and, when she was 14, she ran away from home. Worried and angry, her mother was fed up. After unsuccessfully trying to commit Oprah to a home for troubled teens, Vernita called Oprah’s father Vernon in Nashville, and he agreed to take Oprah in.

THE BIG BREAK

Living with her Father

A few weeks after Oprah arrived to live with her father, her step mother Zelma discovered that Oprah was pregnant. She miscarried. Zelma told Oprah's mother, who came to Nashville immediately. It was then that Oprah began naming all the men she had been with sexually, including her Uncle Trent. That was a shock, but as Oprah said 15 years later, "Everybody in the family sort of shoved it under a rock."

For Oprah this experience would be her greatest, haunting shame, and she would keep the guilt inside her until years later, when her half-sister, Patricia, would humiliate her by revealing it to a tabloid newspaper after Oprah had become famous.

But living with her father Vernon saved her life. With her father, education was a high-priority. Oprah was required to complete weekly book reports, and she went without dinner until she learned five new vocabulary words each day.

“My father turned my life around by insisting that I be more than I was,” Oprah said in an interview. While with her Father, Oprah gave speeches at social gatherings and churches, earning as much as $500 for one speech. It was then when she knew she wanted to be paid to talk.

At 16, Oprah first read the autobiography of Maya Angelou, "I Know Why the Caged Bird Sings." It transformed the teen's outlook, and she later said, "I read it over and over. I had never before read a book that validated my own existence."

"Over the course of my lifetime, books have helped me know that I'm not alone."

This experience changed her outlook, and she began to get her life on track.

Highschool

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Oprah eventually moved back with her mother and began attending a local high school in Milwaukee. Here, she thrived in the Upward Bound program, established to provide disadvantaged youth opportunities for greater education. This success led to her transferring to an affluent suburban high school. Looking to keep up with her new, wealthier peers, Oprah began stealing and rebelling against her mother. Upset, her mother again sent Oprah away to live with Vernon.

With Vernon, Oprah thrived. She was an honours student, voted Most Popular Girl, and joined her high school speech team, placing second in America in dramatic interpretation. Oprah studied public speaking and drama, and was elected school president.

Her success didn't stop there. Oprah was selected to attend the 1971 White House Conference on Youth in Colorado. She was crowned Miss Fire Prevention by WVOL, a local Nashville radio station, and was hired by the station to read afternoon newscasts. She worked at WVOL during her senior year and eventually received a full scholarship to Tennessee State University after winning a public speaking contest.

The job at WVOL would change her life.

Our next newsletter will outline Oprah's superpower - and how you can build this skillset, too. Subscribe to receive it directly in your inbox:

Oprah's Twenties

10,000 hours

During her freshman year at Tennessee State, the Nashville CBS affiliate offered her a job; Winfrey turned it down twice, but finally took the advice of a teacher, who reminded her that job offers from CBS were "the reason people go to college." The show was seen each evening on WTVF-TV, and Winfrey was Nashville's first African American female (and youngest) co-anchor of the evening news. She was nineteen.

When Oprah graduated at 22, WJZ-TV in Baltimore, Maryland, scheduled her to co-anchor the "Six O'Clock News". The job as an anchor presented a challenge. Oprah took the stories to heart, but the anchor role was that of narrator, not sympathetic listener.

“I didn’t like every day having to think of the worst thing that was going to happen that day,” says Winfrey. “I never felt great doing it. I remember being at a funeral and not asking the family of the [deceased] child to comment and getting in trouble for it. The assistant news director was like, ‘You get back out there and ask,’ [but] I couldn’t do it. I was too emotional—I felt things so deeply it was hard for me to let things go. I was worried about the family. It helped lay the groundwork for knowing what I didn’t want to do.”

It didn’t help that the rookie Oprah was paired with the “dean of Baltimore newscasting”, who “had an old-fashioned sense of men and women.”

The pairing was disastrous. Less than eight months after she was hired, Winfrey was dropped from the evening news hours before she was about to go on air.

“I shall never forget April 1, 1977,” said Oprah. “I got called out of the newsroom to meet with the general manager. He said, ‘We think you are so talented, we want you to have your own spot. We are going to move you to morning cut-ins.'” Oprah was devastated and knew it was a "horrible demotion". She was still just 23.

This difficult period was instrumental to her later success. What seemed like a "failure" provided an opportunity that changed her life.

People are Talking

Later that spring, Bill Baker, creator of the highest-rated local program in the country, was hired as general manager of WJZ, and given the task of reinvigorating the ailing station.

Baker met Oprah for the first time at a cocktail party, though it was his wife who identified Oprah's true potential.

“Jeannemarie was a housewife at the time and watched daytime TV,” Baker said. “And she said, ‘You know, if you are going to do a local talk show, that Oprah would be a great host. There is something magical about her—she wears her heart on her sleeve, and she is not at all pretentious.’ I agreed. She had all the right attributes to be a successful talk show host.”

Baker developed his newly named show, People are Talking, and was convinced that Oprah was the perfect person to cohost along with veteran newsman Richard Sher. But Oprah wasn't interested, and felt that she wouldn’t be taken seriously as a journalist.

“It was the last thing in the world she wanted to do,” Baker says. “She said, ‘Bill, I don’t want to do a talk show.’ She had tears in her eyes when she said it.

But from the very first show on August 14, 1978, it was clear that Oprah—with her warmth, natural presence, and ability to extensively ad-lib—had found her calling.

“From that first day, I knew instantly this is what I was supposed to do,” she says. “I felt like I had come home to myself.”

Oprah remained on this show for seven years before a Chicago affiliate saw her audition tape.

Here’s a video clip of Oprah and Richard Sher on People are Talking.

Off-Camera Struggles

Her social life wasn't going so well.

When she was around 27, Oprah reportedly had an affair with a married man who had no intention of leaving his wife. “I'd had a relationship with a man for four years. I wasn't living with him. I'd never lived with anyone—and I thought I was worthless without him. The more he rejected me, the more I wanted him. I felt depleted, powerless. At the end, I was down on the floor on my knees groveling and pleading with him.”

When the affair ended, Oprah became so depressed that in September 1981, at 27 years old, she wrote a suicide note to her best friend.

On Sept. 8, 1981, she wrote to her best friend, Gayle King Bumpas, in which she gave all the details necessary to handle the arrangements after her death, including instructions to water her plants. But as Oprah later told it, "I don't think I was really serious about suicide... I couldn't kill myself. I would be afraid the minute I did it something really good would happen, and I'd miss it."

This emotional devastation took a toll on her body and Oprah began putting on weight.

“The reason I gained so much weight in the first place and the reason I had such a sorry history of abusive relationships with men was I just needed approval so much. I needed everyone to like me, because I didn't like myself much.” A sentiment familiar to many during the tough 20’s.

Chicago

Opportunity Calls

A producer at People Are Talking long admired Oprah. So, while looking for a bigger job, this producer sent a demonstration tape of the show to A.M. Chicago. After the producer was hired to start in January 1984, the host of her new show quit, they immediately thought of Oprah and suggested her to Dennis Swanson, the station manager.

When she turned 29, Oprah moved to Chicago to host A.M. Chicago, a low-rated, half hour talk show.

Oprah signed a four-year deal for $200,000 a year, and said that she had never been more frightened than when she became the host of A.M. Chicago in early 1984.

This chance was all she needed. With Oprah's brassy, lovable attitude and empathetic interviews, the show quickly became the highest rated talk show in Chicago.

You can watch Oprah on AM Chicago in 1984:

After two years, AM Chicago reached its height of popularity and King World (a production company and syndicator of television programming) approached Oprah about taking the show into syndication. Oprah was hesitant at first, but she eventually accepted King World's offer and The Oprah Winfrey Show took flight September 8, 1986.

By 32, Oprah was a millionaire. 

The syndicated show became the number-one daytime talk show in America and ran for 25 years straight. In 2011, Oprah ended her daytime television talk show, leaving behind an amazing legacy.

Skill

In an interview at Stanford, Oprah shared the secret of her success: Empathy. Compassion, a willingness to understand and connect. "The secret to that show, is that people could see themselves in me."

Want to improve your ability to connect with others?

Our next newsletter outlines Oprah's superpower - Empathy - and how you can cultivate this skill, too. Subscribe to receive it directly in your inbox:

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