The moment Oprah Winfrey knew it was time to shut down her daily TV talk show 

Paid attention.
Paid attention.
Image: Reuters/Danny Moloshok
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In 2009, media mogul Oprah Winfrey surprised the viewers of her daily TV talk show by announcing that she would do one more season and then call it quits. In the summer of 2011, she would host the finale of The Oprah Winfrey Show, ending a 25-year run. Explaining the decision, she said at that time, “I love this show, this show has been my life, and I love it enough to know when it’s time to say goodbye.”

(Cue the sobbing of 16.4 million viewers.)

In the current issue of Vogue, however, we learn that there was more behind that decision.

Winfrey, now back in the news as she becomes a special contributor to 60 Minutes and launches a line of food products with Kraft (it’s called “O, That’s Good!”), among other ventures, told journalist Jonathan Van Meter that a few lines from a magazine profile of singer Michael Jackson read to her like a warning, convincing her that it was time to wrap up her much beloved show.

To be sure, she was already mulling that possibility by the time she came across the story. According to Van Meter, “Oprah began to read the tea leaves around 2006.” That’s when she realized that people were moving to an on-demand, mobile form of television consumption, making the 4pm TV time slot far less relevant. Although she would later tell the New York Times in 2011 that nothing—including streaming video—would ever compare to broadcast television’s  ”intimate connection” that happens “right there in somebody’s living room, kitchen, bedroom, den, family room, in that space with them,” she must have realized that her daytime platform was not how she’d reach millions in the next decade.

But the tipping point, Van Meter recounts, came one evening when “she got a sign”:

She was in a hotel in London, and there was a copy of Vanity Fair in her room. “I started reading this incredible article about Michael Jackson, and one of Jackson’s friends was quoted as saying, ‘His number-one problem is that he never realized that Thriller was a phenomenon. And he spent the rest of his life trying to chase it.’ And so, when Bad only sold—only sold—20 million albums early on, he was disappointed because it wasn’t Thriller. He thought he was going to top Thriller. I went, Whoa. Pay attention to that. I didn’t want to be the person chasing a phenomenon. And that is what the Oprah show was. All the right elements came together at the right time. That won’t happen again. People would ask me, ‘Who will be the next Oprah?’ And the answer is: ‘There won’t be.’”

Since she cancelled her talk show, Oprah has had tremendous success. She’s credited with turning around the Oprah Winfrey Network, launched in 2011 as a joint venture with Discovery Communication, by taking creative control (paywall) and stepping in as CEO. She has also revived her acting and producing careers, and has received rave reviews for her acting performances in The Butler and The Immortal Life of Henrietta Lacks. And as most print media products struggle, Winfrey’s O Magazine continues to innovate; it holds enough sway that Amazon recently decided to partner with the brand to sell beauty products.

It’d be wrong to attribute all this success to Winfrey’s luck at having come across that Michael Jackson nugget, of course. It’s her arguably unparalleled media savvy and knack for understanding the times that has made Winfrey a legend.

Still, the lesson she pulled from the Jackson anecdote—that a person must know when to completely change direction rather than chase after former glory—is one that the creators and companies behind big-hit products don’t always grasp on time. Look at Blackberry or Yahoo. Consider what’s happening to so many dine-in restaurants being clobbered by the rise of online ordering and delivery. No one wants to be the fashion brand locked in time, or the musical gods who can’t seem to stay retired. Sometimes success belongs to an era.

To quote Winfrey, “Pay attention.” Phenomenons have a finite lifespan.

Correction: A previous version of this story inaccurately stated that Oprah’s food line is with Weight Watchers. In fact, while Oprah is a stakeholder in Weight Watchers, her food line is with Kraft.