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When Maya Angelou published 1969’s I Know Why the Caged Bird Sings, the bestselling autobiography that would be adapted into a television movie and make her a household name, she was already in her 40s with a variety of career experiences.

Angelou was an actor, dancer, activist and journalist, to name but a few of the roles on her lengthy resumé. Landing a wide range of professional opportunities during an age when all women, but particularly Black women, had limited career prospects, helped Angelou lead a life on her own terms and ultimately rise to prominence as a poet and writer, according to Del Sandeen, author of the 2019 biography .

“She was independent, especially at a time when a lot of women were not expected to work outside of the home,” Sandeen says. “Even if she didn't have experience doing something, she was never afraid to rise up to a challenge.

A 1955 photo of Maya Angelou during her years as a Calypso singer and dancer.

Teen Streetcar Conductor

When Angelou was a teen on hiatus from high school, she made history in 1943 by becoming San Francisco’s first Black streetcar conductor. Although she had no experience in the position, she visited the railway office and asked to apply for the job. Initially, no one took her seriously but, with her mother’s encouragement, Angelou visited the office repeatedly until she received an application and job offer.

“Sometimes the employees in the office would harass her,” Sandeen says. “Sometimes they would ignore her, but she kept going back until they finally gave her the job. She was clearly very determined.”

Her history-making job was a short-lived one. Angelou eventually decided that she needed to complete high school, earning her diploma from George Washington High School in 1945.

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Cocktail Waitress

Shortly after she graduated, Angelou welcomed her only child, Clyde “Guy” Johnson. A 17-year-old mother, she worked as a cook, later moving to Los Angeles and landing a job as a cocktail waitress.

“She had to figure out a way to support herself and her child,” Sandeen says.

At the nightclub where she waited tables, she met a pair of sex workers, finding customers for them for a cut of their earnings. Uneasy about this illicit arrangement, which made her enough money to buy a car, Angelou decided to put L.A. behind her and returned to Stamps, Arkansas, where she’d lived for much of her childhood.

“She admitted in her book that she wasn't proud of that,” Sandeen says. “I guess she felt like, ‘This is what I'm doing for the time being to make money.’ But when she was able to leave, she did.”

Dancer and Singer, Part in 'Porgy and Bess'

Maya Angelou during her days as a dancer, circa 1950

Having taken dance classes as a youth, she successfully auditioned to be the dance partner of a Chicago visitor named R.L. Poole. When Poole reunited with a girlfriend, he replaced Angelou with her. Always resourceful, Angelou moved back to the San Francisco Bay Area, taking odd jobs in a restaurant, dress shop and real estate office. Eventually, she got a gig at a nightclub called the Purple Onion as a dancer and calypso singer, despite lacking vocal training.

“She loved performing, and I think it gave her a creative outlet before she turned to writing,” Sandeen says.

Her club act led her to win a minor part in the musical Porgy and Bess in 1954, the year she divorced her husband of three years, Tosh Angelos. The opportunity took her all over Europe, but she had to leave her son behind in the United States. When she returned from overseas, she vowed not to leave Guy behind again should she have to travel at length, and she kept her word.

In the United States, Angelou continued singing and dancing and began to experiment with writing song lyrics, sketches and short stories. In 1959, she and Guy moved to New York City, giving her access to the network of writers there. She tried playwriting but continued to work as a performer, including at Harlem’s famous Apollo Theater. In 1960, a Cuban magazine published a short story she’d written, but she was still almost a decade out from crafting her hit memoir.

As the civil rights movement gained momentum, Angelou decided to help the fight for racial equality by organizing a show called Cabaret for Freedom to fundraise for the Rev. Martin Luther King Jr.’s Southern Christian Leadership Conference (SCLC). The show ran for five weeks and garnered praise for Angelou. She followed it up by taking a job as the SCLC regional coordinator in which she wrote letters, managed volunteers and made phone calls to fundraise for the movement. She went on to meet King, whom she found surprisingly open and down-to-earth.

Newspaper Editor

The civil rights movement coincided with Africa’s independence movements from colonial oppression. After meeting and falling in love with a South African activist named Vusumzi Make and co-founding the Cultural Association for Women of African Heritage, Angelou traveled with him to the continent in 1961. In Cairo, Egypt, she became editor of The Arab Observer newspaper, working there for a year.

“She had no journalism experience when she accepted the job,” Sandeen says. “But, again, she was like, ‘Okay, well, I guess I'll learn on the job.’ And just like with all the other jobs that she had, all of that shaped her into who she would become.”

When she and Make split in 1962, she moved to Ghana, where she encountered Malcolm X, who had left the Nation of Islam. She planned to return to the U.S. and work for his new group Organization of Afro-American Unity, but Malcolm X was assassinated in early 1965.

As the 1960s grew increasingly violent, claiming King’s life in 1968, Angelou became depressed. She poured her feelings into writing I Know Why the Caged Bird Sings, which chronicles her childhood of abuse and neglect but also of healing and recovery.

Living an unconventional life contributed to Angelou’s success with Caged Bird and beyond, Sandeen says. “One of the things that made her such a good writer was that she knew how to tell stories, and I think just the fact that she had so many experiences gave her so many stories to tell and helped her to be entertaining as she told them.”