Oprah Regrets Not Doing This One Thing After She Decided To End Her Talk Show
"The Oprah Winfrey Show," which transformed Oprah Winfrey into one of the most famous media personalities in the world, ended in 2011 after 29 seasons and over 4000 episodes. Oprah lives an undeniably lavish lifestyle, but that doesn't mean she doesn't work very hard for it. Winfrey launched her basic cable network OWN in January 2011 before her talk show ended, and she told Al Roker on "Today" (via The Wrap) that one of her biggest regrets is that she didn't take a break in between. "I would not have taken on the responsibility of trying to build a network while still ending the show," she said. "That is my one regret ... I should have handled all of that differently, I think. I should have completed one thing, taken a year to do nothing, and then decided what was the next thing for me to do."
On "Today," Winfrey stood by her decision to end "The Oprah Winfrey Show." She admitted that she only regrets not taking the advice that she often gives other people who are at transitional stages in their lives: "When you don't know what to do, do nothing. Get still with yourself and do nothing." Winfrey has overcome some incredibly tragic circumstances in life to become as successful as she is today; she deserves to give herself a real break eventually.
Oprah doesn't take career breaks, but she does take vacations
As a public figure, Oprah Winfrey's career takes her around the world, whether she's in France for Paris Fashion Week or in South Africa visiting the school she founded in 2007 (Oprah Winfrey Leadership Academy for Girls). Celebrities like Winfrey often have such packed schedules and exclusive obligations that it's hard to tell the difference between their work trips and actual vacations. But Winfrey has been on some amazing trips, and one could argue that she earned them based on the false rumors Winfrey's faced in her lifetime.
Vanity Fair reflected on Winfrey's most memorable vacations, including a cross-country road trip with her best friend Gayle King, glamping in Yosemite with Michelle Obama, and a Hawaiian vacation she took with the OWN staff. In a letter to her site subscribers on Oprah Daily in 2024, Winfrey admitted that she loves staycations, but also thinks vacations are important. "When I do venture out, it has to be for a good reason. And exploring the world with the people I want to share the world with is one of the reasons I like to go out into the world," she wrote.