“Life starts at 44,” Winfrey recently said on the Baby, This is Keke Palmer podcast. “Because you come into yourself in a way that you’re no longer trying to please everybody else.”

At that age, Winfrey was in the middle of her stride; she was in her daytime talk-show heyday, having already amassed a collection of Emmy awards for her work hosting The Oprah Winfrey Show; was named one of Time’s “100 Most Influential People of the 20th Century”; and produced and starred in her movie adaptation of Toni Morrison’s Beloved. Winfrey says she was finally in “full drive,” and purposefully living for herself—a hard-won confidence that can take decades to develop.

“I do have some girls now that I’ve mentored who are in their early 30s, who’ve gotten to it sooner,” Winfrey continued. “But for me it was 44 where I locked in…I could see the rising for myself. I wasn’t just doing things for other people.” And research shows she’s not the only one. 

The average founder is 42 years old, and Fortune 500 CEO is 57

Winfrey’s experience isn’t unique to any one profession or industry; many workers come to know that their wisdom and biggest milestones arrive well after the age society tells them they should have “made it.” 

The average Fortune 500 CEO is 57, while the typical billionaire is 57 years old. 

Plus, the stereotype of hoodie-wearing 20-somethings building unicorn companies is largely a founder myth. 

The average person who starts a business is 42 years old—and among the top 0.1% fastest-growing companies, they’re 45—according to the Center of American Entrepreneurship. 

Workers aren’t all running on the same career clock. For Winfrey, that professional reassurance came from a decade of hard work following her big break in her 30s. 

Winfrey’s big break didn’t come until her 30s—now, she can do what she wants 

The now-72-year-old Winfrey spent decades on the grind to get to a place of genuine fulfillment—and now, she says that working relentlessly is non-negotiable in your 20s. 

“You ain’t gonna have no work-life balance at 22, 23,” Winfrey said on the podcast. “You’re not supposed to have it. You’re supposed to lay it in, lay in the work.”

Her own career took off when she was just 19 years old, after becoming the youngest person and first Black woman to anchor the local news at Nashville’s WTVF-TV. After getting a degree from Tennessee State University, she moved to Maryland to become a reporter and anchor, drumming up buzz as the co-host of the Baltimore talk show People Are Talking. Winfrey was on the career grind, attracting bigger audiences with her charismatic personality. 

Then, at 30, a huge professional opportunity was on the table. Winfrey moved to Chicago in 1984 and took over A.M. Chicago, turning it into the top local talk show within months. Many of her peers viewed it as a risky move, with daytime TV legend Phil Donahue being in direct competition in the Windy City. But fellow entertainment icon and longtime friend Gayle King pushed her to take the leap. A couple of years later, her program went national and was renamed The Oprah Winfrey Show. The entrepreneur also founded Harpo Productions the same year, enabling her to take ownership of her own content.

And her success hasn’t been confined to daytime television. Winfrey has taken her talents to Hollywood, starring in movies including The Color Purple, Selma, and The Immortal Life of Henrietta Lacks. She’s also authored a slew of New York Times bestsellers focused on personal growth and health; led the massively popular Oprah’s Book Club since 1996; and founded top-selling lifestyle publication O. 

With $3.4 billion and decades-worth of accolades to her name, Winfrey says she’s living her best life now that she has the “freedom” to do what comes from “the purest part of myself.” 

“I only do what I want to do, and I’ve earned the right to do that. Because there [were] lots of times I had to do what I had to do,” Winfrey added. “You have to do what you have to do, what you need to do, until you can do what you want to do.”