Grass to Grace Series: The inspiring journey of how Oprah Winfrey transformed her humble beginnings into becoming the world’s wealthiest Black woman.

It is always a source of inspiration how relentlessly the human spirit can transcend barriers and boundaries to emerge stronger and triumph over the impossible. One such inspirational stories is how Oprah Winfrey rose from humble beginnings to become the wealthiest black woman in the world.

Oprah, who has her first name spelt as Orpah on her birth certificate, got stuck with the name Oprah because people constantly mispronounced her name. She was born in  Kosciusko, Mississippi, on January 29, 1954, to a teenage mother, Vernita Lee, a housemaid, and a father, Vernon Winfrey, a coal miner turned barber and city councilman. He was in the Armed Forces when she was born.

Oprah was raised by her maternal grandmother for the first six years of her life, where she experienced extreme poverty. Her grandmother taught her to read before age three and helped her grow spiritually by attending the local church with her. By age six, Winfrey moved to an inner-city neighbourhood with her mother, who worked long hours as a maid. Around this time, Oprah’s younger sister Patricia was born, but she later died of drug abuse-related causes in February 2003 at age 43.

By 1962, Lee could not cope with the financial strain of raising both daughters, so Winfrey went to live with Vernon in Nashville, Tennessee, during which time Lee gave birth to a third daughter, whom she also named Patricia and later put up for adoption. Winfrey was unaware of the existence of her second half-sister until 2010, and by the time Oprah moved back with her mother, Lee had also given birth to Winfrey’s half-brother Jeffrey, who died of AIDS-related causes in 1989.

Oprah experienced abuse while growing up. She was molested by her cousin, uncle, and a family friend at a young age, and when she opened up about the abuse later in her 20s, no one believed her. She also suffered some form of emotional neglect because her mum was not supportive. At 13, Oprah ran away from home, became pregnant at 14, and gave birth to a son who was born prematurely and died shortly after birth.

During her years in high school, Oprah went back to live with her dad in Nashville, who taught her discipline and prioritized her education. She became an honours student, was voted Most Popular Girl, and joined her high school speech team. According to Oprah, living with her dad was a transformative experience because he encouraged her to aspire to greater things and be more. Oprah’s first job as a teenager was working at a local grocery store; at 17, she won the Miss Black Tennessee beauty pageant and attracted the attention of the local black radio station, WVOL, where she was hired to anchor the part-time news. She worked there during her senior year of high school and first two years of college; she also won an oratory contest, which secured her a full scholarship to Tennessee State University, where she studied communication.

Speaking about her career success, Oprah’s grandmother once said that ever since Winfrey could talk, she had always envisioned herself on stage. As a child, she played games interviewing her corncob doll and the crows on her family’s property fence. Winfrey also attributes her success to her grandmother’s influence, saying she encouraged her to speak in public and helped her develop a positive sense of self. In 2006, a genetic test determined that Oprah’s matrilineal line originated among the Kpelle ethnic group of modern-day Liberia. Her genetic makeup was deemed to be 89% Sub-Saharan African, 8% “Native American and 3% East Asian.

Oprah co-authored five books. There are speculations that the advance fee for one of her books has broken the record for the world’s highest book advance fee, which Bill Clinton previously held. By 2000, Oprah, with a net worth of $800 million, was believed to have been the richest African American of the 20th century. She holds several real estate portfolios, which, as of 2022, were estimated at approximately $127 million. At 41 years old, Oprah had a net worth of $340 million and replaced Bill Cosby as the only African American on the Forbes 400 list. She was the highest-paid television entertainer in the United States in 2006, earning an estimated $260 million that year, five times the sum earned by second-place music executive Simon Cowell. By 2008, her yearly income had increased to $275 million. Forbes‘ list of The World’s Billionaires has listed Winfrey as the world’s only black billionaire from 2004 to 2006 and as the first black woman billionaire in the world. In 2014, Winfrey had a net worth of $2.9 billion and had overtaken former eBay CEO Meg Whitman as the wealthiest self-made woman in America. According to Celebrity Net Worth, Oprah’s net worth is estimated at $4 billion as of 2025.

Oprah advocates for women and children, and her foundation, the Oprah Winfrey Foundation, awards grants to nonprofits that support women, children, and families. Speaking to women, she emphasizes that women should surround themselves with only positive people who will lift them higher. She says, “Look inward—the loving begins with you; spending time alone is precious because this is when I distance myself from the voices of the world so I can hear my own”.

Amaka is a creative content writer with a passion for serial entrepreneurship. She is the founder of African Gift Shop and Nubian Queens of Canada.